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309 N Greeley Avenue Unit #5C, Chappaqua

Welcome to 309 N. Greeley Avenue. This lovely first floor Town House in the sought-after Chestnut Oaks Community is conveniently located to the heart of downtown Chappaqua. With the award-winning Chappaqua School District and proximity to a Metro North station, this property will not last! This Two Bed, 1 Bath unit has a great layout with a front and back patio! There are no stairs (just one step-down to a sunken Living Room)....enter into this unit and all rooms are one the same level! The main living room is both open and airy with a high ceiling, fireplace and two sliding glass doors leading out to lovely patios and open space. The complex features a swimming pool, tennis and a garden. Make your appointment today!

2 Beds ⋅ 1 Baths ⋅ 1021554 MLS

Welcome to 309 N. Greeley Avenue. This lovely first floor Town House in the sought-after Chestnut Oaks Community is conveniently located to the heart of downtown Chappaqua. With the award-winning Chappaqua School District and proximity to a Metro North station, this property will not last! This Two Bed, 1 Bath unit has a great layout with a front and back patio! There are no stairs (just one step-down to a sunken Living Room)....enter into this unit and all rooms are one the same level! The main living room is both open and airy with a high ceiling, fireplace and two sliding glass doors leading out to lovely patios and open space. The complex features a swimming pool, tennis and a garden. Make your appointment today!

309 N Greeley Avenue Unit #5C, Chappaqua

$1,820,000

Perched on a lushly landscaped acre and thoughtfully expanded, offering a comforting blend of function, space, and versatility for today’s lifestyle, whether working from home (the main-level office opens to a private deck, creating a delightful setting for morning coffee or an inspiring workday), entertaining (the spacious living room with fireplace adjoins the formal dining room with sliding glass door to the patio for easy alfresco dining; the bright eat-in kitchen is smartly designed with custom cabinetry and granite countertops, and a breakfast area with a big bay window and a French door to the patio for immediate access to outdoor cooking and entertaining), or simply enjoying room to spread out (an expanded family room, den/study/playroom/home office x 3, 3 spacious bedrooms, 4 full bathrooms [including 2 ensuite]), there’s a place for everyone to live, work and play. Versatility abounds in the expanded family room with its built-ins and spaces to recreate, work or relax. The luxurious primary suite features a soaring ceiling, oversized windows, boutique-like walk-in closet, and a spa-like bath with double vanity, soaking tub, and separate shower. The second bedroom also features a walk-in closet and an upscale, private ensuite bath with shower. The shared hall bath has been recently refreshed with a double vanity, sconces and mirrors, plus new tile and glass surrounding a bathtub with shower and handheld. The lower-level playroom enjoys easy indoor/outdoor access with a French door to the yard. Commandingly set on a pretty, landscaped acre with a large patio and terraced lawns adding to the scenic surroundings. Welcoming, comforting, spacious and versatile inside and out.

3 Beds ⋅ 4 Baths ⋅ 1020797 MLS

Perched on a lushly landscaped acre and thoughtfully expanded, offering a comforting blend of function, space, and versatility for today’s lifestyle, whether working from home (the main-level office opens to a private deck, creating a delightful setting for morning coffee or an inspiring workday), entertaining (the spacious living room with fireplace adjoins the formal dining room with sliding glass door to the patio for easy alfresco dining; the bright eat-in kitchen is smartly designed with custom cabinetry and granite countertops, and a breakfast area with a big bay window and a French door to the patio for immediate access to outdoor cooking and entertaining), or simply enjoying room to spread out (an expanded family room, den/study/playroom/home office x 3, 3 spacious bedrooms, 4 full bathrooms [including 2 ensuite]), there’s a place for everyone to live, work and play. Versatility abounds in the expanded family room with its built-ins and spaces to recreate, work or relax. The luxurious primary suite features a soaring ceiling, oversized windows, boutique-like walk-in closet, and a spa-like bath with double vanity, soaking tub, and separate shower. The second bedroom also features a walk-in closet and an upscale, private ensuite bath with shower. The shared hall bath has been recently refreshed with a double vanity, sconces and mirrors, plus new tile and glass surrounding a bathtub with shower and handheld. The lower-level playroom enjoys easy indoor/outdoor access with a French door to the yard. Commandingly set on a pretty, landscaped acre with a large patio and terraced lawns adding to the scenic surroundings. Welcoming, comforting, spacious and versatile inside and out.

22 Garey Drive, Chappaqua

$1,100,000

Some homes have good bones. This one has great ones in a private setting. Nestled in Chappaqua's beloved Seven Bridges neighborhood, this 1934 Colonial sits on nearly three-quarters of an acre where tree-lined streets and a true sense of community appeal to buyers who embrace Chappaqua and remain for years. Original hardwood floors, a wood-burning fireplace, crown molding, and a screened porch speak to craftsmanship that simply cannot be replicated. An updated kitchen with granite countertops, wood cabinetry, and a gas range bring real functionality to the floor plan. Main floor offers living room with attached screened in porch, formal dining room, family room / breakfast room, kitchen, huge en-suite bedroom and laundry room. Upstairs holds four more bedrooms, primary ensuite and another full bathroom. Basement has slop sink with laundry hook up and mechanicals. A 2-car garage with a huge walk-up attic, and two additional attics accessed from inside the home give you the space and storage to match your needs. Bring your vision and make it yours in one of Westchester's most sought-after school districts.

5 Beds ⋅ 3 Baths ⋅ 991248 MLS

Some homes have good bones. This one has great ones in a private setting. Nestled in Chappaqua's beloved Seven Bridges neighborhood, this 1934 Colonial sits on nearly three-quarters of an acre where tree-lined streets and a true sense of community appeal to buyers who embrace Chappaqua and remain for years. Original hardwood floors, a wood-burning fireplace, crown molding, and a screened porch speak to craftsmanship that simply cannot be replicated. An updated kitchen with granite countertops, wood cabinetry, and a gas range bring real functionality to the floor plan. Main floor offers living room with attached screened in porch, formal dining room, family room / breakfast room, kitchen, huge en-suite bedroom and laundry room. Upstairs holds four more bedrooms, primary ensuite and another full bathroom. Basement has slop sink with laundry hook up and mechanicals. A 2-car garage with a huge walk-up attic, and two additional attics accessed from inside the home give you the space and storage to match your needs. Bring your vision and make it yours in one of Westchester's most sought-after school districts.

2 Turner Drive, Chappaqua

353 N Greeley Avenue Unit #353, Chappaqua

$650,000

Welcome to Chestnut Oaks. Corner unit Townhome located in building 5 featuring 2 bedrooms, 2 full baths, fireplace, attached garage and balcony. Located in the heart of Chappaqua and close to train, town and schools. Renovated in 2010 with new dine-in kitchen, granite counter tops, stainless steel appliances, hardwood floors, renovated primary bathroom, custom walk-in closet, new washer/dryer and Bose speakers. Community outdoor pool and tennis.

2 Beds ⋅ 2 Baths ⋅ 1017345 MLS

Welcome to Chestnut Oaks. Corner unit Townhome located in building 5 featuring 2 bedrooms, 2 full baths, fireplace, attached garage and balcony. Located in the heart of Chappaqua and close to train, town and schools. Renovated in 2010 with new dine-in kitchen, granite counter tops, stainless steel appliances, hardwood floors, renovated primary bathroom, custom walk-in closet, new washer/dryer and Bose speakers. Community outdoor pool and tennis.

353 N Greeley Avenue Unit #353, Chappaqua

$1,275,000

Welcome to a charming storybook Cape in the award-winning Chappaqua school district. This 3-bedroom, 2-bathroom home is sited on a beautiful, level property and features a 2-car garage attached by breezeway. Freshly painted and move-in ready, this inviting home offers comfortable living in one of Westchester's most sought-after communities. Enjoy the convenience of being just minutes to downtown Chappaqua, the Metro-North train station,restaurants, shopping, parks, and schools, making commuting to New York City and everyday living effortless. The picturesque & yard provides plenty of space for outdoor entertaining, gardening, or simply relaxing. Whether you're looking for your first home, downsizing, or seeking a wonderful opportunity in Chappaqua, this special home combines location, lifestyle, and value. *Electric car charger near garage.

3 Beds ⋅ 2 Baths ⋅ 1034276 MLS

Welcome to a charming storybook Cape in the award-winning Chappaqua school district. This 3-bedroom, 2-bathroom home is sited on a beautiful, level property and features a 2-car garage attached by breezeway. Freshly painted and move-in ready, this inviting home offers comfortable living in one of Westchester's most sought-after communities. Enjoy the convenience of being just minutes to downtown Chappaqua, the Metro-North train station,restaurants, shopping, parks, and schools, making commuting to New York City and everyday living effortless. The picturesque & yard provides plenty of space for outdoor entertaining, gardening, or simply relaxing. Whether you're looking for your first home, downsizing, or seeking a wonderful opportunity in Chappaqua, this special home combines location, lifestyle, and value. *Electric car charger near garage.

1 Commodore Road, Chappaqua

$980,000

Welcome to 42 Hollow Oak Road, a captivating 3-bedroom, 2-bathroom sanctuary nestled in the heart of Chappaqua. Spanning 2,380 square feet, this home perfectly balances suburban tranquility with modern convenience. Step inside to discover a bright, airy layout flooded with natural light. The spacious living areas feature warm hardwood floors, fireplace and a seamless flow, ideal for daily living and entertaining. The heart of the home is a well-appointed kitchen with granite counters. Retreat to the comfortable primary suite, while two additional bedrooms and a hall bath offer versatility for everyone. Lower-level family room, laundry and a home office compliment the flexibility of this home. Outside, the property boasts a serene, wooded backdrop, offering a private oasis for outdoor dining and relaxation on the deck. Well maintained with newer windows, baths, HVAC systems, walkways, lower-level flooring, improved attic insulation and many more updates. Located in the highly acclaimed Chappaqua School District, this home is just minutes from the charming town center, local dining, and the Metro-North station for an easy NYC commute. Your dream home awaits!

3 Beds ⋅ 2 Baths ⋅ 1035131 MLS

Welcome to 42 Hollow Oak Road, a captivating 3-bedroom, 2-bathroom sanctuary nestled in the heart of Chappaqua. Spanning 2,380 square feet, this home perfectly balances suburban tranquility with modern convenience. Step inside to discover a bright, airy layout flooded with natural light. The spacious living areas feature warm hardwood floors, fireplace and a seamless flow, ideal for daily living and entertaining. The heart of the home is a well-appointed kitchen with granite counters. Retreat to the comfortable primary suite, while two additional bedrooms and a hall bath offer versatility for everyone. Lower-level family room, laundry and a home office compliment the flexibility of this home. Outside, the property boasts a serene, wooded backdrop, offering a private oasis for outdoor dining and relaxation on the deck. Well maintained with newer windows, baths, HVAC systems, walkways, lower-level flooring, improved attic insulation and many more updates. Located in the highly acclaimed Chappaqua School District, this home is just minutes from the charming town center, local dining, and the Metro-North station for an easy NYC commute. Your dream home awaits!

42 Hollow Oak Road, Chappaqua

$549,000

Opportunities like this do not come around often in Chappaqua, and when they do, they tend to move quickly. What is being offered at 58 Maple Ave is a flat, level, in-town parcel with an existing 2-bedroom, 1-bath cottage set back from the road among towering pines, in one of Westchester County's most coveted villages. Whether a buyer chooses to develop the land, renovate what is there, or simply occupy the existing structure while planning next steps, the opportunity here is defined first and foremost by the location and the lot. The cottage itself, built in 1930 and totaling 711 square feet, is being sold strictly as-is. It sits on a 0.28-acre lot with driveway parking and includes a front deck, a patio, and a yard with a quiet, private feel that genuinely surprises you given how close you are to the center of town. Inside, the main level includes a great room with cathedral ceilings and built-in features, a kitchen, two bedrooms, and a full bath. A partial basement with Bilco door access houses laundry and mechanicals. The structure has a history as a consistently rentable asset in a market where rental demand is strong and vacancy is rare, which speaks to the enduring appeal of this particular address regardless of what a future owner ultimately decides to do with it. The location is the defining feature and the reason this property commands the attention it does. You are minutes on foot from the Chappaqua Metro-North Station, putting Midtown Manhattan within comfortable commuting distance without the stress of a car or a parking lot. The village's boutique shops, restaurants, and parks are equally walkable, giving this address an everyday livability that most Westchester properties simply cannot replicate. For those who travel frequently for business, Westchester County Airport is also easily accessible. This is a genuinely rare convergence of walkability, transit access, and village character that defines the upper end of what Chappaqua real estate has to offer. The property falls within the Chappaqua Central School District, one of the most highly regarded public school systems in New York State and a consistent driver of demand in this market. Flat lot, set-back privacy, walk-to-train location, and Chappaqua schools.

2 Beds ⋅ 1 Baths ⋅ 993303 MLS

Opportunities like this do not come around often in Chappaqua, and when they do, they tend to move quickly. What is being offered at 58 Maple Ave is a flat, level, in-town parcel with an existing 2-bedroom, 1-bath cottage set back from the road among towering pines, in one of Westchester County's most coveted villages. Whether a buyer chooses to develop the land, renovate what is there, or simply occupy the existing structure while planning next steps, the opportunity here is defined first and foremost by the location and the lot. The cottage itself, built in 1930 and totaling 711 square feet, is being sold strictly as-is. It sits on a 0.28-acre lot with driveway parking and includes a front deck, a patio, and a yard with a quiet, private feel that genuinely surprises you given how close you are to the center of town. Inside, the main level includes a great room with cathedral ceilings and built-in features, a kitchen, two bedrooms, and a full bath. A partial basement with Bilco door access houses laundry and mechanicals. The structure has a history as a consistently rentable asset in a market where rental demand is strong and vacancy is rare, which speaks to the enduring appeal of this particular address regardless of what a future owner ultimately decides to do with it. The location is the defining feature and the reason this property commands the attention it does. You are minutes on foot from the Chappaqua Metro-North Station, putting Midtown Manhattan within comfortable commuting distance without the stress of a car or a parking lot. The village's boutique shops, restaurants, and parks are equally walkable, giving this address an everyday livability that most Westchester properties simply cannot replicate. For those who travel frequently for business, Westchester County Airport is also easily accessible. This is a genuinely rare convergence of walkability, transit access, and village character that defines the upper end of what Chappaqua real estate has to offer. The property falls within the Chappaqua Central School District, one of the most highly regarded public school systems in New York State and a consistent driver of demand in this market. Flat lot, set-back privacy, walk-to-train location, and Chappaqua schools.

58 Maple Avenue, Chappaqua

$1,551,000

Set on a sought-after cul-de-sac lined with charming classic homes, this 1938 Colonial masterfully blends period charm with today’s lifestyle needs. Set on a lovely private acre with flat lawns surrounded by towering trees yet nestled in a neighborhood setting, this 2,715 square foot center hall Colonial home offers 4 bedrooms, 2 full and 2 half baths. The heart of the home is the family room open to the kitchen, featuring a raised hearth stacked stone fireplace, custom built-ins, and a door to the deck and patio. The eat-in kitchen is a chef’s dream, with tile flooring, a large center island, wood cabinetry, glass tile backsplash, and premium stainless steel appliances including a 6-burner Wolf gas range with addt'l griddle and grill, double ovens, and a Sub-Zero refrigerator — plus its own door to the deck. A screened porch offers additional space for indoor-outdoor living. Elegant formal spaces include a living room with fireplace and built-ins, and a dining room with built-in corner cupboards, both showcasing beautiful oak hardwood floors throughout. The primary bedroom suite is a true retreat, with an adjacent sunroom/home office, walk-in closet, and en-suite full bath. Three additional bedrooms and a hall bath complete the upper level. Additional highlights include main floor laundry, a side door entry, ample basement storage, and expansion potential over the garage. Recent updates include a roof just 8 years new, boiler (2015), new windows in the kitchen, family room, sunroom, and 2 bathrooms, 4-zone heat, 2-zone central air, and a portable generator hookup for peace of mind. Cedar shake exterior adds to the timeless curb appeal. Located in the award-winning Chappaqua school district, close to shops, schools and metro North commuter train, this is a rare opportunity to own a piece of classic Chappaqua charm with all the modern comforts today’s buyers demand.

4 Beds ⋅ 4 Baths ⋅ 1020963 MLS

Set on a sought-after cul-de-sac lined with charming classic homes, this 1938 Colonial masterfully blends period charm with today’s lifestyle needs. Set on a lovely private acre with flat lawns surrounded by towering trees yet nestled in a neighborhood setting, this 2,715 square foot center hall Colonial home offers 4 bedrooms, 2 full and 2 half baths. The heart of the home is the family room open to the kitchen, featuring a raised hearth stacked stone fireplace, custom built-ins, and a door to the deck and patio. The eat-in kitchen is a chef’s dream, with tile flooring, a large center island, wood cabinetry, glass tile backsplash, and premium stainless steel appliances including a 6-burner Wolf gas range with addt'l griddle and grill, double ovens, and a Sub-Zero refrigerator — plus its own door to the deck. A screened porch offers additional space for indoor-outdoor living. Elegant formal spaces include a living room with fireplace and built-ins, and a dining room with built-in corner cupboards, both showcasing beautiful oak hardwood floors throughout. The primary bedroom suite is a true retreat, with an adjacent sunroom/home office, walk-in closet, and en-suite full bath. Three additional bedrooms and a hall bath complete the upper level. Additional highlights include main floor laundry, a side door entry, ample basement storage, and expansion potential over the garage. Recent updates include a roof just 8 years new, boiler (2015), new windows in the kitchen, family room, sunroom, and 2 bathrooms, 4-zone heat, 2-zone central air, and a portable generator hookup for peace of mind. Cedar shake exterior adds to the timeless curb appeal. Located in the award-winning Chappaqua school district, close to shops, schools and metro North commuter train, this is a rare opportunity to own a piece of classic Chappaqua charm with all the modern comforts today’s buyers demand.

50 Ludlow Drive, Chappaqua

$2,020,000

Nestled on over an acre of beautifully landscaped grounds in the highly sought-after Chappaqua School District, this exceptional residence offers a rare blend of privacy, craftsmanship, and versatility. Behind a gated entrance, mature specimen plantings, expansive lawns, and a tranquil natural setting create a true private retreat just minutes from downtown Chappaqua and Metro-North. Thoughtfully improved throughout the years, the home features cedar siding, Anderson windows and sliding doors, custom hardwood flooring with intricate inlay detail, reinforced structural beams, remote-controlled skylights, and numerous mechanical upgrades. Dramatic ceilings, walls of windows, and sun-drenched living spaces create an inviting atmosphere designed for both everyday living and entertaining. The eat-in kitchen is appointed with custom cabinetry, premium stainless steel appliances, a center island, and seamless access to the outdoor deck. Formal and informal living spaces flow effortlessly throughout the main level, highlighted by a dramatic living room with soaring ceilings, oversized windows, and a marble fireplace. The luxurious primary suite serves as a private retreat featuring custom California Closets and a stunning spa-inspired bath with a freestanding soaking tub, oversized glass-enclosed shower with body jets and bench seating, custom mahogany detailing, designer lighting, and exceptional finishes throughout. Renovated bathrooms throughout the home showcase custom tilework, premium fixtures, and thoughtful spa designs. Additional highlights include California Closets throughout, intercom and surround sound systems, smart gate access, surveillance cameras, irrigation system, renovated garage, and a charming detached storage shed. Outdoor living is equally impressive with expansive decking, a remote-controlled SunSetter awning, and peaceful grounds designed for entertaining and relaxation. A truly special offering combining privacy, quality craftsmanship, modern conveniences, and exceptional flexibility in one of Westchester County's most desirable communities.

4 Beds ⋅ 4 Baths ⋅ 1011189 MLS

Nestled on over an acre of beautifully landscaped grounds in the highly sought-after Chappaqua School District, this exceptional residence offers a rare blend of privacy, craftsmanship, and versatility. Behind a gated entrance, mature specimen plantings, expansive lawns, and a tranquil natural setting create a true private retreat just minutes from downtown Chappaqua and Metro-North. Thoughtfully improved throughout the years, the home features cedar siding, Anderson windows and sliding doors, custom hardwood flooring with intricate inlay detail, reinforced structural beams, remote-controlled skylights, and numerous mechanical upgrades. Dramatic ceilings, walls of windows, and sun-drenched living spaces create an inviting atmosphere designed for both everyday living and entertaining. The eat-in kitchen is appointed with custom cabinetry, premium stainless steel appliances, a center island, and seamless access to the outdoor deck. Formal and informal living spaces flow effortlessly throughout the main level, highlighted by a dramatic living room with soaring ceilings, oversized windows, and a marble fireplace. The luxurious primary suite serves as a private retreat featuring custom California Closets and a stunning spa-inspired bath with a freestanding soaking tub, oversized glass-enclosed shower with body jets and bench seating, custom mahogany detailing, designer lighting, and exceptional finishes throughout. Renovated bathrooms throughout the home showcase custom tilework, premium fixtures, and thoughtful spa designs. Additional highlights include California Closets throughout, intercom and surround sound systems, smart gate access, surveillance cameras, irrigation system, renovated garage, and a charming detached storage shed. Outdoor living is equally impressive with expansive decking, a remote-controlled SunSetter awning, and peaceful grounds designed for entertaining and relaxation. A truly special offering combining privacy, quality craftsmanship, modern conveniences, and exceptional flexibility in one of Westchester County's most desirable communities.

4 Old House Lane, Chappaqua

$1,595,000

Rare opportunity to own two side-by-side residences on a beautifully landscaped 0.45-acre property in the highly sought-after Chappaqua School District. 52 Orchard Ridge features a renovated 3-bedroom, 1.5-bath home with hardwood floors, stainless steel appliances, updated cabinetry and countertops, and in-unit laundry. This residence will be delivered vacant at closing, offering immediate occupancy for an owner-user. 54 Orchard Ridge offers 4 bedrooms, 1 bath, in-unit laundry, ample basement storage, and is currently leased, providing immediate rental income. The property also features attractive landscaping, a large driveway, generous outdoor space, and an approximately 800-square-foot accessory cottage attached to the main residence, offering flexibility for a home office, studio, recreation space, or other permitted uses. Ideally located within walking distance to downtown Chappaqua, shops, restaurants, parks, and everyday amenities, this property combines convenience, charm, and exceptional lifestyle appeal. Whether you're seeking a multigenerational living arrangement, an investment opportunity, or the ability to live in one residence while generating rental income from the other, this unique property offers versatility, strong income potential, and long-term value in one of Westchester County's most desirable communities and top-rated school districts.

7 Beds ⋅ 3 Baths ⋅ 1012149 MLS

Rare opportunity to own two side-by-side residences on a beautifully landscaped 0.45-acre property in the highly sought-after Chappaqua School District. 52 Orchard Ridge features a renovated 3-bedroom, 1.5-bath home with hardwood floors, stainless steel appliances, updated cabinetry and countertops, and in-unit laundry. This residence will be delivered vacant at closing, offering immediate occupancy for an owner-user. 54 Orchard Ridge offers 4 bedrooms, 1 bath, in-unit laundry, ample basement storage, and is currently leased, providing immediate rental income. The property also features attractive landscaping, a large driveway, generous outdoor space, and an approximately 800-square-foot accessory cottage attached to the main residence, offering flexibility for a home office, studio, recreation space, or other permitted uses. Ideally located within walking distance to downtown Chappaqua, shops, restaurants, parks, and everyday amenities, this property combines convenience, charm, and exceptional lifestyle appeal. Whether you're seeking a multigenerational living arrangement, an investment opportunity, or the ability to live in one residence while generating rental income from the other, this unique property offers versatility, strong income potential, and long-term value in one of Westchester County's most desirable communities and top-rated school districts.

52-54 Orchard Ridge Road, Chappaqua

$870,000

Straight from the pages of a storybook, this enchanting French Revival Tudor-inspired home is tucked amongst a canopy of mature trees and natural stone walls which create an unforgettable first impression. A winding stone walkway leads to a charming covered entry highlighted by a stained glass front door, hinting at the warmth and character that await inside. Living room with fireplace, eat-in kitchen with farm sink, beamed ceilings, and updated appliances with access out to a large terraced patio. Offering three Bedrooms, the primary bedroom/bath provide access to third floor flexible space as office/studio with additional storage. Finished lower level designed for versatility as recreation/media/playroom, complete with powder room, laundry, utilities and garage. Rich in architectural detail and overflowing with charm, this is the kind of home that instantly captures your heart. Award winning Chappaqua school district; 4 minutes to the Chappaqua metro north train station, 46 Min. express to Grand Central, 0.9 miles to town.

3 Beds ⋅ 2 Baths ⋅ 1020907 MLS

Straight from the pages of a storybook, this enchanting French Revival Tudor-inspired home is tucked amongst a canopy of mature trees and natural stone walls which create an unforgettable first impression. A winding stone walkway leads to a charming covered entry highlighted by a stained glass front door, hinting at the warmth and character that await inside. Living room with fireplace, eat-in kitchen with farm sink, beamed ceilings, and updated appliances with access out to a large terraced patio. Offering three Bedrooms, the primary bedroom/bath provide access to third floor flexible space as office/studio with additional storage. Finished lower level designed for versatility as recreation/media/playroom, complete with powder room, laundry, utilities and garage. Rich in architectural detail and overflowing with charm, this is the kind of home that instantly captures your heart. Award winning Chappaqua school district; 4 minutes to the Chappaqua metro north train station, 46 Min. express to Grand Central, 0.9 miles to town.

220 Mill River Road, Chappaqua

$905,000

Welcome to Old Farm Lake - one of Chappaqua's most desirable condominium communities, offering low-maintenance living with resort-style amenities. This 3-bedroom, 2.5-bath townhome is set in a private setting and lives beautifully with natural light across three levels. The main level features an open living and dining area with cathedral ceilings, a skylight, and a wood-burning fireplace. The eat-in kitchen offers granite countertops, custom Rutt cherry cabinetry, stainless steel appliances, and a Sub-Zero refrigerator with direct access to a private patio overlooking the woods. Hardwood floors, a half bath, and one-car garage access complete the main level. Upstairs, the primary suite includes an en-suite bath and walk-in closet, with two additional bedrooms and a full hall bath. The lower level offers finished storage or a dedicated workspace. Community amenities include a pool, tennis courts, sport court, fitness center, clubhouse, and playground - all maintained for you. Just 1 mile to the Chappaqua train station and village.

3 Beds ⋅ 3 Baths ⋅ 1008622 MLS

Welcome to Old Farm Lake - one of Chappaqua's most desirable condominium communities, offering low-maintenance living with resort-style amenities. This 3-bedroom, 2.5-bath townhome is set in a private setting and lives beautifully with natural light across three levels. The main level features an open living and dining area with cathedral ceilings, a skylight, and a wood-burning fireplace. The eat-in kitchen offers granite countertops, custom Rutt cherry cabinetry, stainless steel appliances, and a Sub-Zero refrigerator with direct access to a private patio overlooking the woods. Hardwood floors, a half bath, and one-car garage access complete the main level. Upstairs, the primary suite includes an en-suite bath and walk-in closet, with two additional bedrooms and a full hall bath. The lower level offers finished storage or a dedicated workspace. Community amenities include a pool, tennis courts, sport court, fitness center, clubhouse, and playground - all maintained for you. Just 1 mile to the Chappaqua train station and village.

20 Waters Edge, Chappaqua

$1,475,000

Welcome to 26 Meadow Lane, a pristine 2,178-square-foot ranch set on over half an acre of flat, beautifully landscaped property in one of Chappaqua’s most coveted residential neighborhoods. A rocking chair front porch and Belgian block-lined driveway offer an immediate sense of arrival, while sidewalk-lined streets connect the neighborhood to the acclaimed village of Chappaqua, minutes from restaurants, shopping, playgrounds, the library, Metro-North rail service, and more. Situated within the highly sought-after Chappaqua Central School District, including Roaring Brook Elementary and Robert E. Bell Middle School. The sun-drenched main level features a cathedral-ceiling living room anchored by a dramatic stone fireplace that adds immediate texture, warmth, and luxury to the space. The formal dining room overlooks a stunning yard, while the expansive skylit eat-in kitchen with cathedral ceiling offers an abundance of counter space, a center island, and a built-in entertaining hutch with glass-front cabinetry. A screened porch flows to an expanded stone patio below that lives like a true outdoor living room, seamlessly extending your entertaining space into the beautifully level yard. The primary suite with renovated en-suite bath, two additional bedrooms, a full hall bathroom, and a home office complete the main level. The lower level is anchored by an expansive family room with slider to the patio, complemented by a mudroom, laundry room, half bath, and generous storage throughout. Additional highlights include wood floors, custom closet organizers, extensive crown molding throughout, whole-house generator hookup, dual-zone heating and central air, two-car attached garage, and fresh paint throughout. Legal three-bedroom with flexible four-bedroom living, 2.5 baths, septic, public water, and natural gas. Immaculate, versatile, and perfectly positioned for future expansion.

3 Beds ⋅ 3 Baths ⋅ 978589 MLS

Welcome to 26 Meadow Lane, a pristine 2,178-square-foot ranch set on over half an acre of flat, beautifully landscaped property in one of Chappaqua’s most coveted residential neighborhoods. A rocking chair front porch and Belgian block-lined driveway offer an immediate sense of arrival, while sidewalk-lined streets connect the neighborhood to the acclaimed village of Chappaqua, minutes from restaurants, shopping, playgrounds, the library, Metro-North rail service, and more. Situated within the highly sought-after Chappaqua Central School District, including Roaring Brook Elementary and Robert E. Bell Middle School. The sun-drenched main level features a cathedral-ceiling living room anchored by a dramatic stone fireplace that adds immediate texture, warmth, and luxury to the space. The formal dining room overlooks a stunning yard, while the expansive skylit eat-in kitchen with cathedral ceiling offers an abundance of counter space, a center island, and a built-in entertaining hutch with glass-front cabinetry. A screened porch flows to an expanded stone patio below that lives like a true outdoor living room, seamlessly extending your entertaining space into the beautifully level yard. The primary suite with renovated en-suite bath, two additional bedrooms, a full hall bathroom, and a home office complete the main level. The lower level is anchored by an expansive family room with slider to the patio, complemented by a mudroom, laundry room, half bath, and generous storage throughout. Additional highlights include wood floors, custom closet organizers, extensive crown molding throughout, whole-house generator hookup, dual-zone heating and central air, two-car attached garage, and fresh paint throughout. Legal three-bedroom with flexible four-bedroom living, 2.5 baths, septic, public water, and natural gas. Immaculate, versatile, and perfectly positioned for future expansion.

26 Meadow Lane, Chappaqua

$715,000

Experience the best of convenient living in this stylishly updated 3-bedroom home, perfectly situated in a walk-to-all neighborhood near the train, schools, shopping, and library. This meticulously maintained property boasts significant modern upgrades, including double pane windows, Hardiplank siding, and a spacious Trex deck overlooking a private, flat, grassy backyard. Inside, enjoy hardwood floors and LED lighting throughout, leading you into a bright living room with crown molding and large windows that frame the deep front yard. The kitchen is a chef's delight, featuring quartz countertops, a deep stainless steel sink, and stainless steel appliances, including a gas range and French door refrigerator. The king-size primary bedroom has an en suite bathroom and offers direct access to the deck, while the walk-out lower level adds versatile living space, complete with a private office, a third bedroom with an en-suite bath, and laundry. This home is ready for you to move in and enjoy!

3 Beds ⋅ 3 Baths ⋅ 1011499 MLS

Experience the best of convenient living in this stylishly updated 3-bedroom home, perfectly situated in a walk-to-all neighborhood near the train, schools, shopping, and library. This meticulously maintained property boasts significant modern upgrades, including double pane windows, Hardiplank siding, and a spacious Trex deck overlooking a private, flat, grassy backyard. Inside, enjoy hardwood floors and LED lighting throughout, leading you into a bright living room with crown molding and large windows that frame the deep front yard. The kitchen is a chef's delight, featuring quartz countertops, a deep stainless steel sink, and stainless steel appliances, including a gas range and French door refrigerator. The king-size primary bedroom has an en suite bathroom and offers direct access to the deck, while the walk-out lower level adds versatile living space, complete with a private office, a third bedroom with an en-suite bath, and laundry. This home is ready for you to move in and enjoy!

80 Bischoff Avenue, Chappaqua

$1,250,000

Move right into this sparkling, beautifully updated 4-bedroom Colonial, ideally located in the highly sought-after Chappaqua School District. Blending timeless pre-war charm with modern amenities, this home offers exceptional comfort and style. Freshly painted inside and out, the home features beautiful hardwood floors, recessed lighting, a renovated kitchen, updated bathrooms, a wood burning stove and more . A walk-up attic provides excellent storage or future expansion possibilities. Outside, enjoy a large, private property with mature landscaping and perennial gardens, a usable yard, and an expanded driveway accented by elegant Belgian block edging. Additional highlights include an above-ground oil tank and a convenient location close to schools, shopping, dining, transportation, and all that the area has to offer. A truly turnkey opportunity combining character, updates, and convenience.

4 Beds ⋅ 3 Baths ⋅ 977211 MLS

Move right into this sparkling, beautifully updated 4-bedroom Colonial, ideally located in the highly sought-after Chappaqua School District. Blending timeless pre-war charm with modern amenities, this home offers exceptional comfort and style. Freshly painted inside and out, the home features beautiful hardwood floors, recessed lighting, a renovated kitchen, updated bathrooms, a wood burning stove and more . A walk-up attic provides excellent storage or future expansion possibilities. Outside, enjoy a large, private property with mature landscaping and perennial gardens, a usable yard, and an expanded driveway accented by elegant Belgian block edging. Additional highlights include an above-ground oil tank and a convenient location close to schools, shopping, dining, transportation, and all that the area has to offer. A truly turnkey opportunity combining character, updates, and convenience.

21 Campfire Road, Chappaqua

$826,000

Welcome to 134 Bayberry Close in the sought-after Old Farm Lake community, in the heart of Chappaqua. This spacious 2-bedroom, 2.5-bathroom townhouse offers over 1,800 sq ft of living space across three levels, including a finished walk-out lower level. The main level features an eat-in kitchen, a dining area with sliding glass doors to the deck, and a sun-filled living room with cathedral ceilings and a fireplace. Upstairs, the nicely sized primary suite offers a walk-in closet and en-suite bath, while the second bedroom features its own full bath. Laundry is conveniently located on the upper level. The lower level provides valuable flexible living space, featuring a family room and a separate area ideal for a home office, gym, or guest space. Residents enjoy exceptional community amenities including pool, tennis courts, clubhouse, playground, and basketball court, all just minutes to town, train, shopping, and top-rated Chappaqua schools. A rare opportunity to own in one of Chappaqua’s most desirable condominium communities. Additional highlights include a new water heater, central air, natural gas heat, attached 1-car garage, and excellent storage.

2 Beds ⋅ 3 Baths ⋅ 995272 MLS

Welcome to 134 Bayberry Close in the sought-after Old Farm Lake community, in the heart of Chappaqua. This spacious 2-bedroom, 2.5-bathroom townhouse offers over 1,800 sq ft of living space across three levels, including a finished walk-out lower level. The main level features an eat-in kitchen, a dining area with sliding glass doors to the deck, and a sun-filled living room with cathedral ceilings and a fireplace. Upstairs, the nicely sized primary suite offers a walk-in closet and en-suite bath, while the second bedroom features its own full bath. Laundry is conveniently located on the upper level. The lower level provides valuable flexible living space, featuring a family room and a separate area ideal for a home office, gym, or guest space. Residents enjoy exceptional community amenities including pool, tennis courts, clubhouse, playground, and basketball court, all just minutes to town, train, shopping, and top-rated Chappaqua schools. A rare opportunity to own in one of Chappaqua’s most desirable condominium communities. Additional highlights include a new water heater, central air, natural gas heat, attached 1-car garage, and excellent storage.

134 Bayberry Close, Chappaqua

$2,310,018

Welcome to this warm, inviting 5-bedroom home nestled on a tree-lined beautiful Chappaqua street. It has a lovely front porch with plenty of room for cozy chairs, perfect for sipping coffee in the morning. Inside, there is a spacious living room with a wood burning fireplace, a bright kitchen and a large island. First floor features a Primary Suite, 4 additional bedrooms with 2 full baths upstairs as well as two offices.There is a large finished basement that runs the length of the house with an additional full bath. The charm really comes through in the details- wood floors, perfect layout, wood built -ins and big windows letting in lots of light. It’s the kind of home and neighborhood you just fall in love with.

5 Beds ⋅ 5 Baths ⋅ 978706 MLS

Welcome to this warm, inviting 5-bedroom home nestled on a tree-lined beautiful Chappaqua street. It has a lovely front porch with plenty of room for cozy chairs, perfect for sipping coffee in the morning. Inside, there is a spacious living room with a wood burning fireplace, a bright kitchen and a large island. First floor features a Primary Suite, 4 additional bedrooms with 2 full baths upstairs as well as two offices.There is a large finished basement that runs the length of the house with an additional full bath. The charm really comes through in the details- wood floors, perfect layout, wood built -ins and big windows letting in lots of light. It’s the kind of home and neighborhood you just fall in love with.

1 Hitching Post Lane, Chappaqua

$1,299,000

Just north of NYC, this move-in ready CHAPPAQUA home delivers effortless, elevated living—done RIGHT. 3 min drive to Metro North station - 48 min ride to Grand Central Station * Set behind a long private driveway with an attached 2-car garage and expansive front yard, the property captures stunning sunset views, with golden hour pouring in the best way. Inside captures a calm, grounded palette with clean, high-end finishes that deliver a serene feel. The layout is open, airy and flows naturally, anchored by a striking limewashed fireplace. At the center a 10-FT ISLAND defines the kitchen with an extended space for additional storage and coffee bar. Trifold door opens wide to create SEAMLESS INDOOR-OUTDOOR LIVING, leading to a multi-patio backyard designed for easy entertaining and memorable gatherings. The dining area is finished with a custom board and batten accent wall for added depth and character. Thoughtful details carry throughout—like the HIDDEN BOOKSHELF DOOR leading to a main-level laundry room, a SECOND laundry room in the basement and a custom entry bench with built-in Storage. The Bathrooms are designed with a spa-level feel, featuring heated floors, a soaking tub, and LED-lit mirrors. LED Recessed lighting runs all throughout the home * SMART HOME features include lights, appliances, heated bathroom floors, hot water system, thermostat and home surveillance system. < Motorized security camera system included The FINISHED BASEMENT offers flexible BONUS ROOM with an additional fireplace. Even the garage is upgraded with LED lighting and garage flooring for a clean, functional setup. Located in a prime Chappaqua setting within a highly sought-after school district. Turn-key, well-designed, and ready to be lived in. Buyer agent to verify all info * note ; With so many options available Buyer has the opportunity to choose the shower glass they desire for Primary & basement bathrooms Brand new Hot water tank and Pressure Tank AO

3 Beds ⋅ 3 Baths ⋅ 989797 MLS

Just north of NYC, this move-in ready CHAPPAQUA home delivers effortless, elevated living—done RIGHT. 3 min drive to Metro North station - 48 min ride to Grand Central Station * Set behind a long private driveway with an attached 2-car garage and expansive front yard, the property captures stunning sunset views, with golden hour pouring in the best way. Inside captures a calm, grounded palette with clean, high-end finishes that deliver a serene feel. The layout is open, airy and flows naturally, anchored by a striking limewashed fireplace. At the center a 10-FT ISLAND defines the kitchen with an extended space for additional storage and coffee bar. Trifold door opens wide to create SEAMLESS INDOOR-OUTDOOR LIVING, leading to a multi-patio backyard designed for easy entertaining and memorable gatherings. The dining area is finished with a custom board and batten accent wall for added depth and character. Thoughtful details carry throughout—like the HIDDEN BOOKSHELF DOOR leading to a main-level laundry room, a SECOND laundry room in the basement and a custom entry bench with built-in Storage. The Bathrooms are designed with a spa-level feel, featuring heated floors, a soaking tub, and LED-lit mirrors. LED Recessed lighting runs all throughout the home * SMART HOME features include lights, appliances, heated bathroom floors, hot water system, thermostat and home surveillance system. < Motorized security camera system included The FINISHED BASEMENT offers flexible BONUS ROOM with an additional fireplace. Even the garage is upgraded with LED lighting and garage flooring for a clean, functional setup. Located in a prime Chappaqua setting within a highly sought-after school district. Turn-key, well-designed, and ready to be lived in. Buyer agent to verify all info * note ; With so many options available Buyer has the opportunity to choose the shower glass they desire for Primary & basement bathrooms Brand new Hot water tank and Pressure Tank AO

816 Hardscrabble Road, Chappaqua

$750,000

Offering over 1650SF of living space, this spacious townhouse in the sought-after Old Farm Lake community has private wooded views and an open, light-filled floor plan. The living room which is open to the dining area, features cathedral ceilings, a wood-burning fireplace, and sliding glass doors to a private deck. A renovated eat-in kitchen is well- appointed with granite countertops and stainless-steel appliances. Additional on this level is a den/office and powder room. The second floor offers a spacious primary suite with cathedral ceiling, a custom organized walk-in closet and ensuite bathroom. The second bedroom also has an ensuite bathroom. Basement provides a great place for all of your storage. Enjoy resort-style amenities including a pool, tennis courts, clubhouse, paddle and basketball courts, and playground. Conveniently located in the Chappaqua School District, just minutes from shopping, parks, Metro-North, and an easy commute to New York City.

2 Beds ⋅ 3 Baths ⋅ 1015610 MLS

Offering over 1650SF of living space, this spacious townhouse in the sought-after Old Farm Lake community has private wooded views and an open, light-filled floor plan. The living room which is open to the dining area, features cathedral ceilings, a wood-burning fireplace, and sliding glass doors to a private deck. A renovated eat-in kitchen is well- appointed with granite countertops and stainless-steel appliances. Additional on this level is a den/office and powder room. The second floor offers a spacious primary suite with cathedral ceiling, a custom organized walk-in closet and ensuite bathroom. The second bedroom also has an ensuite bathroom. Basement provides a great place for all of your storage. Enjoy resort-style amenities including a pool, tennis courts, clubhouse, paddle and basketball courts, and playground. Conveniently located in the Chappaqua School District, just minutes from shopping, parks, Metro-North, and an easy commute to New York City.

110 Woods End Road, Chappaqua

$1,510,000

Location, location, location! Traditional 3-bedroom, 2.1-bath colonial-style home serenely set on a prime, flat 1.14-acre parcel. Covered front portico. Spacious living room with wood burning fireplace and hardwood flooring. Formal dining room with bay window, hardwood flooring and door to sunroom (additional 150sqft not included in total) with garden sink and slider to deck with steps to backyard. Eat-in kitchen with picture window to backyard and GE appliances including 4-burner electric cooktop, double in-wall ovens, refrigerator/freezer and dishwasher. Private home office. Rear entryway with powder room and main-level garage access. Rear-corner primary bedroom with two closets and private ensuite bath. Front-corner bedroom and front-facing bedroom with closet access to walk-up, unfinished attic share hall bath with shower over bathtub. Walk-out basement offers recreation room with wood-burning fireplace (additional 400+/-sqft not included in total), large unfinished storage or workshop and utility/laundry room with Whirlpool washer, Maytag dryer, slop sink and door to side yard. New indoor above-ground oil tank. Flat, easy driveway. Rare, flat-as-a-pancake backyard surrounded with lush and mature landscaping. One of the most sought-after neighborhoods in Chappaqua within walking distance to school and close proximity to shops, town and train. A prime opportunity.

3 Beds ⋅ 3 Baths ⋅ 1003079 MLS

Location, location, location! Traditional 3-bedroom, 2.1-bath colonial-style home serenely set on a prime, flat 1.14-acre parcel. Covered front portico. Spacious living room with wood burning fireplace and hardwood flooring. Formal dining room with bay window, hardwood flooring and door to sunroom (additional 150sqft not included in total) with garden sink and slider to deck with steps to backyard. Eat-in kitchen with picture window to backyard and GE appliances including 4-burner electric cooktop, double in-wall ovens, refrigerator/freezer and dishwasher. Private home office. Rear entryway with powder room and main-level garage access. Rear-corner primary bedroom with two closets and private ensuite bath. Front-corner bedroom and front-facing bedroom with closet access to walk-up, unfinished attic share hall bath with shower over bathtub. Walk-out basement offers recreation room with wood-burning fireplace (additional 400+/-sqft not included in total), large unfinished storage or workshop and utility/laundry room with Whirlpool washer, Maytag dryer, slop sink and door to side yard. New indoor above-ground oil tank. Flat, easy driveway. Rare, flat-as-a-pancake backyard surrounded with lush and mature landscaping. One of the most sought-after neighborhoods in Chappaqua within walking distance to school and close proximity to shops, town and train. A prime opportunity.

100 Devoe Road, Chappaqua

$1,370,000

Escape to your own private retreat on 3.44 acres of wooded land, where rustic charm meets modern comfort. This unique residence was thoughtfully expanded in 2005 and refined with modern luxuries while preserving its timeless character. The beautifully crafted, freshly painted 2,708-square-foot home offers 3 bedrooms and 4 bathrooms in a serene, nature-filled setting. Inside, you'll find a thoughtfully designed open-concept layout featuring a modern kitchen that flows seamlessly into a stunning log cabin-style living room. In addition, a sun-filled family room provides exceptional flexibility and can easily serve as a fourth bedroom, home office, or guest suite. The first-floor bedroom adds convenience and accessibility for family members and visitors alike. Step outside and discover an extraordinary outdoor lifestyle. Explore your own private forest hiking trails and designated picnic area, enjoy the playground, relax on the inviting front porch, or entertain guests on the expansive stone patio. The property also features a stone-rimmed natural pool, a charming gazebo, and a unique stone pizza oven—perfect for outdoor gatherings, dining, and creating lasting memories. Offering the rare combination of privacy and convenience, this peaceful sanctuary is just minutes from shopping, restaurants, and schools. Located only 35 miles from New York City, it provides the perfect balance of tranquil country living and easy access to world-class amenities. Whether you're searching for a forever home, a weekend getaway, or a vacation retreat, this one-of-a-kind property offers an exceptional lifestyle in a truly picturesque setting.

3 Beds ⋅ 4 Baths ⋅ 1006943 MLS

Escape to your own private retreat on 3.44 acres of wooded land, where rustic charm meets modern comfort. This unique residence was thoughtfully expanded in 2005 and refined with modern luxuries while preserving its timeless character. The beautifully crafted, freshly painted 2,708-square-foot home offers 3 bedrooms and 4 bathrooms in a serene, nature-filled setting. Inside, you'll find a thoughtfully designed open-concept layout featuring a modern kitchen that flows seamlessly into a stunning log cabin-style living room. In addition, a sun-filled family room provides exceptional flexibility and can easily serve as a fourth bedroom, home office, or guest suite. The first-floor bedroom adds convenience and accessibility for family members and visitors alike. Step outside and discover an extraordinary outdoor lifestyle. Explore your own private forest hiking trails and designated picnic area, enjoy the playground, relax on the inviting front porch, or entertain guests on the expansive stone patio. The property also features a stone-rimmed natural pool, a charming gazebo, and a unique stone pizza oven—perfect for outdoor gatherings, dining, and creating lasting memories. Offering the rare combination of privacy and convenience, this peaceful sanctuary is just minutes from shopping, restaurants, and schools. Located only 35 miles from New York City, it provides the perfect balance of tranquil country living and easy access to world-class amenities. Whether you're searching for a forever home, a weekend getaway, or a vacation retreat, this one-of-a-kind property offers an exceptional lifestyle in a truly picturesque setting.

25 Cabin Ridge Road, Chappaqua

$1,925,000

Perfectly situated on over three picturesque acres, this timeless 5 bedroom Federal Colonial effortlessly blends historical charm with modern convenience. Thoughtfully updated while maintaining its classic character, the home offers expansive living spaces, refined finishes, and an exceptional layout designed for today’s lifestyle. At the heart of the home is the stunning chef’s kitchen featuring a Wolf 6-burner range with grill and double ovens, Sub-Zero refrigerator, custom maple cabinetry, large banquette and oversized island — all seamlessly opening to the dining room and dramatic great room, ideal for both everyday living and entertaining. A charming screened-in “lemonade porch” invites peaceful mornings and relaxed summer evenings overlooking the beautiful property. The home offers a flexible and functional floor plan featuring a private first-floor guest suite, separate office spaces, and, upstairs, a quaint secondary bedroom wing accented with irreplaceable wide plank floors. For added privacy, the expansive primary suite can be accessed via a secondary staircase. The luxurious primary retreat features a spa-like bath and oversized his and hers walk-in closets, creating a true sanctuary. Outside, enjoy resort-style living with a heated Gunite pool, expansive upper and lower patios, sweeping lawns, a very special Williamsburg style potager, and mature landscaping — all offering incredible usable outdoor space rarely found in the area. There’s even room for a future tennis or pickleball court. Located in the highly sought-after Byram Hills School District with convenient access to Chappaqua train parking, downtown shops, restaurants, and local favorites, this exceptional property offers the perfect balance of privacy, charm, and everyday convenience — all with low taxes.

5 Beds ⋅ 5 Baths ⋅ 995576 MLS

Perfectly situated on over three picturesque acres, this timeless 5 bedroom Federal Colonial effortlessly blends historical charm with modern convenience. Thoughtfully updated while maintaining its classic character, the home offers expansive living spaces, refined finishes, and an exceptional layout designed for today’s lifestyle. At the heart of the home is the stunning chef’s kitchen featuring a Wolf 6-burner range with grill and double ovens, Sub-Zero refrigerator, custom maple cabinetry, large banquette and oversized island — all seamlessly opening to the dining room and dramatic great room, ideal for both everyday living and entertaining. A charming screened-in “lemonade porch” invites peaceful mornings and relaxed summer evenings overlooking the beautiful property. The home offers a flexible and functional floor plan featuring a private first-floor guest suite, separate office spaces, and, upstairs, a quaint secondary bedroom wing accented with irreplaceable wide plank floors. For added privacy, the expansive primary suite can be accessed via a secondary staircase. The luxurious primary retreat features a spa-like bath and oversized his and hers walk-in closets, creating a true sanctuary. Outside, enjoy resort-style living with a heated Gunite pool, expansive upper and lower patios, sweeping lawns, a very special Williamsburg style potager, and mature landscaping — all offering incredible usable outdoor space rarely found in the area. There’s even room for a future tennis or pickleball court. Located in the highly sought-after Byram Hills School District with convenient access to Chappaqua train parking, downtown shops, restaurants, and local favorites, this exceptional property offers the perfect balance of privacy, charm, and everyday convenience — all with low taxes.

765 King Street, Chappaqua

$1,830,000

Thoughtfully reimagined farmhouse with barn, this distinctive 4-bedroom, 3-bath home blends historic charm with striking modern design. Set on close to 2 private acres surrounded by mature trees, the property offers exceptional privacy and a peaceful natural setting. Inside, soaring ceilings, oversized windows, and multiple skylights flood the home with natural light. The open-concept living space flows seamlessly into a sleek contemporary kitchen featuring custom cabinetry, a large center island, premium appliances, and walls of glass that connect the interior to the surrounding landscape—ideal for both everyday living and entertaining. Solar panels enhance the home’s efficiency, adding a thoughtful, sustainable element to its modern design. The home offers four well-proportioned bedrooms and three beautifully designed full baths, including a serene primary suite with a spa-like bath featuring a soaking tub and double vanity. A versatile loft area provides flexible space for a home office, guest quarters, and more.The sun-filled lower level with expansive picture windows creates an inviting lounge or media space and includes a lovely, newly renovated laundry room with a hot stone sauna. A rare blend of modern architecture, farmhouse warmth, sustainability, and privacy on close to two acres in Chappaqua.

4 Beds ⋅ 3 Baths ⋅ 968769 MLS

Thoughtfully reimagined farmhouse with barn, this distinctive 4-bedroom, 3-bath home blends historic charm with striking modern design. Set on close to 2 private acres surrounded by mature trees, the property offers exceptional privacy and a peaceful natural setting. Inside, soaring ceilings, oversized windows, and multiple skylights flood the home with natural light. The open-concept living space flows seamlessly into a sleek contemporary kitchen featuring custom cabinetry, a large center island, premium appliances, and walls of glass that connect the interior to the surrounding landscape—ideal for both everyday living and entertaining. Solar panels enhance the home’s efficiency, adding a thoughtful, sustainable element to its modern design. The home offers four well-proportioned bedrooms and three beautifully designed full baths, including a serene primary suite with a spa-like bath featuring a soaking tub and double vanity. A versatile loft area provides flexible space for a home office, guest quarters, and more.The sun-filled lower level with expansive picture windows creates an inviting lounge or media space and includes a lovely, newly renovated laundry room with a hot stone sauna. A rare blend of modern architecture, farmhouse warmth, sustainability, and privacy on close to two acres in Chappaqua.

734 King Street, Chappaqua

$2,555,000

Exquisite architectural design, timeless charm & luxurious modern amenities merge effortlessly in this elegant Colonial in the heart of Chappaqua. C.1902 & superbly upgraded and meticulously maintained, the home offers an open, sun-bathed interior w/hardwood floors, high ceilings, abundant built-ins, extensive millwork and a quintessential porch - sure to please the most discerning buyers! The gracious foyer leads to a classic dining room with fine millwork, a fireplace and boasts a lovely historical handpainted mural of the Hudson Valley at the turn of the century. The formal living room with concealed pocket doors has a second fireplace and French doors opening to the covered porch. The sunny and bright eat-in kitchen is a chef’s dream featuring a Wolf double oven, Sub Zero fridge, ample storage and opens to the casual living room/ leisure room. 2nd floor features a primary bedroom suite with a sparkling spa bath, walk-in closet and and adjoining office. An additional 3 bedrooms and a tastefully renovated hall bath complete the second floor. Finished 3rd level includes a bedroom and Bonus room perfect for studio/office/playroom w/ full hall bath. The large unfinished basement offers additional space and Bilco doors to the exterior. A 2 car detached garage originally used as stables has 2 levels and offers many possibilities. The park-like, level property is professionally landscaped and is an oasis of tranquility w/ lush lawns, a dazzling variety of specimen trees & plantings with ample parking. Ideally located close to town, train, schools and more!

5 Beds ⋅ 4 Baths ⋅ 974885 MLS

Exquisite architectural design, timeless charm & luxurious modern amenities merge effortlessly in this elegant Colonial in the heart of Chappaqua. C.1902 & superbly upgraded and meticulously maintained, the home offers an open, sun-bathed interior w/hardwood floors, high ceilings, abundant built-ins, extensive millwork and a quintessential porch - sure to please the most discerning buyers! The gracious foyer leads to a classic dining room with fine millwork, a fireplace and boasts a lovely historical handpainted mural of the Hudson Valley at the turn of the century. The formal living room with concealed pocket doors has a second fireplace and French doors opening to the covered porch. The sunny and bright eat-in kitchen is a chef’s dream featuring a Wolf double oven, Sub Zero fridge, ample storage and opens to the casual living room/ leisure room. 2nd floor features a primary bedroom suite with a sparkling spa bath, walk-in closet and and adjoining office. An additional 3 bedrooms and a tastefully renovated hall bath complete the second floor. Finished 3rd level includes a bedroom and Bonus room perfect for studio/office/playroom w/ full hall bath. The large unfinished basement offers additional space and Bilco doors to the exterior. A 2 car detached garage originally used as stables has 2 levels and offers many possibilities. The park-like, level property is professionally landscaped and is an oasis of tranquility w/ lush lawns, a dazzling variety of specimen trees & plantings with ample parking. Ideally located close to town, train, schools and more!

111 Prospect Drive, Chappaqua

$2,250,000

Set on a picturesque property in sought-after Random Farms, this stunning 6-bedroom residence offers dramatic views, soaring ceilings, and exceptional living spaces designed for both everyday comfort and elegant entertaining. A breathtaking double-height entry welcomes you into sun-drenched interiors featuring walls of windows, rich hardwood floors, and seamless open-concept flow throughout. The spectacular great room is the heart of the home, highlighted by oversized architectural windows, a striking fireplace, and direct access to outdoor living spaces overlooking the serene landscape. The spacious chef’s kitchen features extensive custom cabinetry, premium appliances, large center island, and sunny breakfast area perfect for gathering. Designed with flexibility in mind, the home includes a full first-floor guest suite and a private first-floor office with custom built-ins — ideal for today’s work-from-home lifestyle. Additional highlights include elegant formal living and dining rooms, generous secondary bedrooms, and beautifully scaled entertaining spaces throughout. Located within the prestigious Random Farms community offering clubhouse, pool, tennis, and lifestyle amenities, this exceptional home combines privacy, luxury, and convenience just minutes to town, train, and top-rated Chappaqua schools.

6 Beds ⋅ 6 Baths ⋅ 1002982 MLS

Set on a picturesque property in sought-after Random Farms, this stunning 6-bedroom residence offers dramatic views, soaring ceilings, and exceptional living spaces designed for both everyday comfort and elegant entertaining. A breathtaking double-height entry welcomes you into sun-drenched interiors featuring walls of windows, rich hardwood floors, and seamless open-concept flow throughout. The spectacular great room is the heart of the home, highlighted by oversized architectural windows, a striking fireplace, and direct access to outdoor living spaces overlooking the serene landscape. The spacious chef’s kitchen features extensive custom cabinetry, premium appliances, large center island, and sunny breakfast area perfect for gathering. Designed with flexibility in mind, the home includes a full first-floor guest suite and a private first-floor office with custom built-ins — ideal for today’s work-from-home lifestyle. Additional highlights include elegant formal living and dining rooms, generous secondary bedrooms, and beautifully scaled entertaining spaces throughout. Located within the prestigious Random Farms community offering clubhouse, pool, tennis, and lifestyle amenities, this exceptional home combines privacy, luxury, and convenience just minutes to town, train, and top-rated Chappaqua schools.

22 Random Farms Circle, Chappaqua

$2,915,000

Welcome to an exceptional move-in ready home located in a highly desirable Chappaqua neighborhood known for its award-winning schools & sought-after lifestyle. Perfectly positioned at the end of a quiet cul-de-sac, this stunning & chic property offers privacy, space & luxury living at its finest. Step inside & you'll find a bright, open-concept floor plan with natural light & high-end finishes throughout. The eat-in gourmet stylish kitchen is a chef's dream, complete with stainless steel appliances, custom cabinetry & a large center island - perfect for entertaining or everyday living. The inviting living room & elegant dining space provide a seamless flow, ideal for gatherings of any size. The upstairs boast 5 spacious bedrooms, including a luxurious primary suite compete with spa-inspired bathroom, oversized shower, & two generous walk-in closets. Four additional bedrooms provide flexible living, including a convenient jack & jill bathroom - optimal for family or guests. The noteworthy fully finished lower level offers additional living space with a large family room, private office & home gym - perfect for the current style of living. Outside, step into your own private resort-style oasis designed for ultimate outdoor living, featuring an in-ground gunite saltwater pool with an electric cover, a spacious patio with fire pit and built-in grill w/refrigerator. You will also enjoy a large flat yard with and existing vegetable garden. Additional highlights include fully owned energy-efficient solar panels & thoughtful upgrades throughout, including a convienent doggy door making this home as practical as it is luxurious. Whether you're a first time home buyer or upgrading, this is a rare opportunity to own a turn-key home in one of Westchester's finest communities. Come visit today!

5 Beds ⋅ 5 Baths ⋅ 967996 MLS

Welcome to an exceptional move-in ready home located in a highly desirable Chappaqua neighborhood known for its award-winning schools & sought-after lifestyle. Perfectly positioned at the end of a quiet cul-de-sac, this stunning & chic property offers privacy, space & luxury living at its finest. Step inside & you'll find a bright, open-concept floor plan with natural light & high-end finishes throughout. The eat-in gourmet stylish kitchen is a chef's dream, complete with stainless steel appliances, custom cabinetry & a large center island - perfect for entertaining or everyday living. The inviting living room & elegant dining space provide a seamless flow, ideal for gatherings of any size. The upstairs boast 5 spacious bedrooms, including a luxurious primary suite compete with spa-inspired bathroom, oversized shower, & two generous walk-in closets. Four additional bedrooms provide flexible living, including a convenient jack & jill bathroom - optimal for family or guests. The noteworthy fully finished lower level offers additional living space with a large family room, private office & home gym - perfect for the current style of living. Outside, step into your own private resort-style oasis designed for ultimate outdoor living, featuring an in-ground gunite saltwater pool with an electric cover, a spacious patio with fire pit and built-in grill w/refrigerator. You will also enjoy a large flat yard with and existing vegetable garden. Additional highlights include fully owned energy-efficient solar panels & thoughtful upgrades throughout, including a convienent doggy door making this home as practical as it is luxurious. Whether you're a first time home buyer or upgrading, this is a rare opportunity to own a turn-key home in one of Westchester's finest communities. Come visit today!

3 Pondfield Drive S, Chappaqua

$1,625,000

Completely reimagined and move-in ready, this sun-filled 3-bedroom plus home office, 2.5-bath home sits on over one acre of rare, level property in one of Chappaqua’s most sought-after neighborhoods. Blending modern updates with timeless design, the home offers a bright, open flow ideal for today’s lifestyle, with expansive windows that flood every room with natural light. The main level showcases an expansive living room with a newly added gas fireplace and dual picture windows, a dedicated home office ideal for remote work, and a beautifully updated eat-in kitchen that flows seamlessly into an open-concept dining room —perfect for everyday living and entertaining. Step outside to a large deck overlooking the private, flat backyard, offering exceptional indoor-outdoor living. Just off the kitchen, a half-flight of stairs leads to a versatile ground level bonus room with picture windows, windowed powder room, and conveniently located mudroom with direct access to the attached two-car garage—ideal for everyday convenience. The second level, features a generous primary suite with a walk-in closet and en-suite bath, along with two additional spacious bedrooms and a full hall bathroom. The expansive lower level provides additional flexible living space, including a recreation room a windowed laundry room along with ample storage space. Set on meticulously maintained, park-like grounds with mature plantings, this property offers the perfect combination of tranquility and convenience. Just minutes to downtown Chappaqua, schools, train, Gedney Park, shopping, and dining!

3 Beds ⋅ 3 Baths ⋅ 987916 MLS

Completely reimagined and move-in ready, this sun-filled 3-bedroom plus home office, 2.5-bath home sits on over one acre of rare, level property in one of Chappaqua’s most sought-after neighborhoods. Blending modern updates with timeless design, the home offers a bright, open flow ideal for today’s lifestyle, with expansive windows that flood every room with natural light. The main level showcases an expansive living room with a newly added gas fireplace and dual picture windows, a dedicated home office ideal for remote work, and a beautifully updated eat-in kitchen that flows seamlessly into an open-concept dining room —perfect for everyday living and entertaining. Step outside to a large deck overlooking the private, flat backyard, offering exceptional indoor-outdoor living. Just off the kitchen, a half-flight of stairs leads to a versatile ground level bonus room with picture windows, windowed powder room, and conveniently located mudroom with direct access to the attached two-car garage—ideal for everyday convenience. The second level, features a generous primary suite with a walk-in closet and en-suite bath, along with two additional spacious bedrooms and a full hall bathroom. The expansive lower level provides additional flexible living space, including a recreation room a windowed laundry room along with ample storage space. Set on meticulously maintained, park-like grounds with mature plantings, this property offers the perfect combination of tranquility and convenience. Just minutes to downtown Chappaqua, schools, train, Gedney Park, shopping, and dining!

14 Garey Drive, Chappaqua

$1,950,000

Beautifully updated split ranch set on 1.02 park-like acres in a sought-after Chappaqua location near school, train and walkable to village center train and shops. The heart of this home is a spectacular high-end renovated eat-in kitchen featuring white cabinetry, Wolf, Miele, and Sub-Zero appliances, honed marble and granite counters, a center island with pendant lighting, a peninsula with seating, a walk-in pantry, bay window and a door to the patio-all flowing seamlessly into the living room with stacked stone fireplace, family room, and large dining area with bay window and crown molding. Wide-board pegged oak hardwood floors, crown molding and an abundance of natural light enhance the warm, inviting ambiance throughout. The living room showcases a dramatic floor-to-ceiling stacked stone raised hearth fireplace and custom built-ins. The light-filled family room impresses with soaring ceilings, a skylight, windows on three exposures, and French doors opening to a slate patio- perfect for indoor-outdoor living. A windowed main-level laundry room with built-ins and a renovated powder room add everyday convenience. Upstairs, are four bedrooms-three generous bedrooms with wide-board pegged oak floors and double closets share a newly renovated hall bath with double-sink vanity and full tub. A privacy door leads to the primary suite with king-size bedroom, oversized windowed walk-in closet, and an updated en-suite spa style bath with skylight, jetted tub, large storage vanity and frameless glass shower. The expansive lower level offers exceptional flexibility and has a playroom with sliding glass doors to a lower patio, home office, powder room, large mudroom, and an oversized two-car garage with storage alcove. The fenced backyard with multi-level patios and flat lawn presents a potential pool site. Additional features include new windows, professional landscaping, wired-for-generator, EV charger, closet organizers, 10-year new roof, 4 zone HVAC, and low taxes. Truly move-in condition, a gem, won’t last.

4 Beds ⋅ 4 Baths ⋅ 1008366 MLS

Beautifully updated split ranch set on 1.02 park-like acres in a sought-after Chappaqua location near school, train and walkable to village center train and shops. The heart of this home is a spectacular high-end renovated eat-in kitchen featuring white cabinetry, Wolf, Miele, and Sub-Zero appliances, honed marble and granite counters, a center island with pendant lighting, a peninsula with seating, a walk-in pantry, bay window and a door to the patio-all flowing seamlessly into the living room with stacked stone fireplace, family room, and large dining area with bay window and crown molding. Wide-board pegged oak hardwood floors, crown molding and an abundance of natural light enhance the warm, inviting ambiance throughout. The living room showcases a dramatic floor-to-ceiling stacked stone raised hearth fireplace and custom built-ins. The light-filled family room impresses with soaring ceilings, a skylight, windows on three exposures, and French doors opening to a slate patio- perfect for indoor-outdoor living. A windowed main-level laundry room with built-ins and a renovated powder room add everyday convenience. Upstairs, are four bedrooms-three generous bedrooms with wide-board pegged oak floors and double closets share a newly renovated hall bath with double-sink vanity and full tub. A privacy door leads to the primary suite with king-size bedroom, oversized windowed walk-in closet, and an updated en-suite spa style bath with skylight, jetted tub, large storage vanity and frameless glass shower. The expansive lower level offers exceptional flexibility and has a playroom with sliding glass doors to a lower patio, home office, powder room, large mudroom, and an oversized two-car garage with storage alcove. The fenced backyard with multi-level patios and flat lawn presents a potential pool site. Additional features include new windows, professional landscaping, wired-for-generator, EV charger, closet organizers, 10-year new roof, 4 zone HVAC, and low taxes. Truly move-in condition, a gem, won’t last.

105 Cross Ridge, Chappaqua

$1,731,000

Most “walk-to-town” homes ask you to compromise on space, privacy, or both. At 14 Crossways, you get all three. Set less than a mile from the Chappaqua station, it combines true walkability with more than 3,100 square feet of well-organized living space on a private, level half-acre. Carefully maintained and thoughtfully improved, it is also a house designed for entertaining. At its center, the kitchen acts as the engine room of the home, anchored by a substantial island and flowing directly into the family room, dining room, and screened porch. Because the porch is accessed from the kitchen, the connection between indoor and outdoor living feels particularly natural and highly practical. From the family room, the house also connects directly to the lower level, allowing the living spaces to expand easily when people spread out. The first floor also includes a dedicated office and a separate guest bedroom with a full bath, positioned to function independently from the main living areas. Upstairs, the nearly 600 square foot primary wing is set apart, offering a true sense of scale and separation, along with a walk-in closet and primary bath. Two additional bedrooms and a full bath are located on the opposite side, creating a balanced and practical second floor. The lower level adds a large recreation room, a powder room, and a custom wine cellar, giving the house a valuable secondary entertaining space that is fully integrated into the overall layout. A rare combination of scale, function, and convenience in the heart of Chappaqua.

4 Beds ⋅ 4 Baths ⋅ 985955 MLS

Most “walk-to-town” homes ask you to compromise on space, privacy, or both. At 14 Crossways, you get all three. Set less than a mile from the Chappaqua station, it combines true walkability with more than 3,100 square feet of well-organized living space on a private, level half-acre. Carefully maintained and thoughtfully improved, it is also a house designed for entertaining. At its center, the kitchen acts as the engine room of the home, anchored by a substantial island and flowing directly into the family room, dining room, and screened porch. Because the porch is accessed from the kitchen, the connection between indoor and outdoor living feels particularly natural and highly practical. From the family room, the house also connects directly to the lower level, allowing the living spaces to expand easily when people spread out. The first floor also includes a dedicated office and a separate guest bedroom with a full bath, positioned to function independently from the main living areas. Upstairs, the nearly 600 square foot primary wing is set apart, offering a true sense of scale and separation, along with a walk-in closet and primary bath. Two additional bedrooms and a full bath are located on the opposite side, creating a balanced and practical second floor. The lower level adds a large recreation room, a powder room, and a custom wine cellar, giving the house a valuable secondary entertaining space that is fully integrated into the overall layout. A rare combination of scale, function, and convenience in the heart of Chappaqua.

14 Crossways, Chappaqua

$799,000

TURNKEY in every way! Beautiful End Unit Townhouse in Old Farm Lake with private wooded views. Spacious Living Room with Wood Burning Fireplace and Cathedral Ceilings. Open Floor Plan with Living Room/Dining Room combination and sliding glass doors out to Deck. Renovated Eat in Kitchen with Carrera Marble counters and Stainless Steel Appliances -- including Bosch Dishwasher, Fisher & Paykel Refrigerator, GE Gas Range and Oven. Entry Foyer with Coat Closet, Powder Room & Door to Garage. Second Floor includes a spacious Primary Bedroom Suite with Walk-in Closet & Updated Primary Bathroom. An Additional Bedroom Ensuite with Full Bath, Laundry Area with New GE Washer/Dryer and Pull Down Stairs to Attic. Complex has Pool, Tennis, Clubhouse, Paddle/Basketball Court and Playground. Convenient to Chappaqua Schools, Library, Shopping, Train Station, Parks & Recreation. Easy NYC Commute. THIS HOME IS NOT TO BE MISSED!

2 Beds ⋅ 3 Baths ⋅ 1006449 MLS

TURNKEY in every way! Beautiful End Unit Townhouse in Old Farm Lake with private wooded views. Spacious Living Room with Wood Burning Fireplace and Cathedral Ceilings. Open Floor Plan with Living Room/Dining Room combination and sliding glass doors out to Deck. Renovated Eat in Kitchen with Carrera Marble counters and Stainless Steel Appliances -- including Bosch Dishwasher, Fisher & Paykel Refrigerator, GE Gas Range and Oven. Entry Foyer with Coat Closet, Powder Room & Door to Garage. Second Floor includes a spacious Primary Bedroom Suite with Walk-in Closet & Updated Primary Bathroom. An Additional Bedroom Ensuite with Full Bath, Laundry Area with New GE Washer/Dryer and Pull Down Stairs to Attic. Complex has Pool, Tennis, Clubhouse, Paddle/Basketball Court and Playground. Convenient to Chappaqua Schools, Library, Shopping, Train Station, Parks & Recreation. Easy NYC Commute. THIS HOME IS NOT TO BE MISSED!

127 Stone Bridge Square, Chappaqua

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Tierra Stanback