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17 Byram Meadows Road, Chappaqua
$2,486,000
4 Beds ⋅ 5 Baths ⋅ 953370 MLS
Beautifully appointed and meticulously maintained 4 bedroom, 4 1/2 bath Colonial set on a level acre at the end of a quiet cul-de-sac in prestigious Inglenook Farm in the coveted Byram Hills Schools. A grand and light-filled two-story entry welcomes you into this refined open layout home featuring 9-foot ceilings on 1st and 2nd levels, oak flooring, and custom moldings and trim throughout. Formal living and dining rooms lead to a Chef's eat-in kitchen with granite countertops, oversized island, stainless appliances and dining area. The kitchen opens to a spacious family room with wood burning fireplace and doors to an expansive deck overlooking the serene, park-like level backyard. A mudroom off the kitchen provides everyday convenience, and a separate back bonus/recreation room adds flexible space for work, play, or relaxation. Upstairs, the primary suite features a spa-like bath, dressing area, and oversized custom-outfitted closet. The finished legal walkout lower level includes a large recreation room, gym, full bath, and ample storage. Other highlights include a large laundry room, large walk-in pantry and a 3-car attached garage. Whole house generator. Located just minutes to the towns of Chappaqua and Armonk, in the Byram Hills School District and just 45 minutes from NYC, this home is not to be missed. TAXES BEING GRIEVED.

17 Byram Meadows Road, Chappaqua

2 Dewitt Drive, Chappaqua
$1,745,000
2 Beds ⋅ 4 Baths ⋅ 986167 MLS
Welcome to 2 DeWitt Drive — a stunning 2025-built carriage home offering refined luxury and effortless living in one of Chappaqua’s most desirable communities. This light-filled corner residence spans 3,574 square feet with 2 spacious bedrooms (lives like a 3BR) and 3.5 baths, thoughtfully designed with high-end finishes and sophisticated upgrades throughout. Expansive windows flood the home with natural light and showcase the beautiful grassy expanse bordering the front and side of the property, creating an airy, open feel rarely found in attached living. The main living spaces blend elegance and comfort with designer details, premium materials, and a seamless flow. The generous primary suite offers a true retreat, while flexible bonus spaces provide room for multiple home offices, media room, or guest accommodation. Enjoy warm-weather living on the expansive second-floor terrace with beautiful open views, or relax on the inviting front porch overlooking the generous grassy lawn right at your feet. This home delivers the best of new construction without the wait. Residents enjoy exclusive access to a private clubhouse featuring a beautifully appointed common area, fitness center, and pool. Located within the Chappaqua School District and set in a vibrant mixed-use community with Whole Foods, Starbucks, Restaurants and Shopping just moments away, this property offers a rare combination of luxury, convenience, and lifestyle. A sophisticated, low-maintenance opportunity in the heart of Chappaqua.

2 Dewitt Drive, Chappaqua

26 Wallace Way, Chappaqua
$1,780,000
2 Beds ⋅ 4 Baths ⋅ 951859 MLS
Welcome to 26 Wallace Way — a standout residence in the coveted, sold-out Chappaqua Crossings Carriages community. Thoughtfully designed and impeccably finished, this first-floor primary bedroom home elevates townhouse living with refined interiors, dramatic architecture, and a setting that is both private and connected. The main level makes an immediate impression with a dramatic double-height living room, where oversized windows flood the space with natural light and tranquil views of the open grass courtyard placing the home at the heart of one of the community’s most desirable locations. The chef’s kitchen flows seamlessly into the living and dining areas, anchored by a generous center island, custom cabinetry, and premium appliances, creating an ideal layout for both everyday living and entertaining. The primary suite offers effortless main-level living, complete with a spa-inspired bath and an expansive walk-in closet. A stylish powder room, along with thoughtful storage, laundry, and garage access, completes the level. Upstairs, a sunlit loft serves as a versatile lounge or gathering space with western exposure showcasing beautiful sunsets beyond. From here, step out to the private outdoor terrace overlooking landscaped grounds and treetops—a peaceful retreat perfect for morning coffee or evening unwinding. This level also features a well-appointed second bedroom, a full bath, and a dedicated home office, along with large walk-in closets that enhance both comfort and functionality. The living space extends even further with a finished basement, ideal for an additional bedroom, media room, or gym, and is complemented by a third full bathroom. The home also includes dedicated areas on all three levels for a future elevator, offering long-term flexibility and ease of living. Just a short walk from the clubhouse and pool, the amenities feel like a natural extension of your home. Residents enjoy walkable access to the fitness center, Whole Foods, Life Time, shops, and restaurants, along with a dedicated shuttle to the train for effortless commuting. Built by Toll Brothers, known for exceptional quality and craftsmanship, 26 Wallace Way offers a rare blend of first-floor primary living, dramatic architectural design, privacy, and resort-style amenities in one of Chappaqua’s most sought-after communities.

26 Wallace Way, Chappaqua

21 Hemlock Hills, Chappaqua
$2,725,033
4 Beds ⋅ 4 Baths ⋅ 981974 MLS
Experience modern luxury at 21 Hemlock Hills, a stunning home set on 1.8 acres of meticulously landscaped grounds. This residence features 4 spacious bedrooms and 3.5 bathrooms, including a gorgeous, luxurious master bathroom that serves as a private retreat. The heart of the home is the Carol Kurth-designed Leicht kitchen, a masterpiece featured in a magazine, seamlessly flowing into the open great room—perfect for entertaining or everyday living. A dedicated home office provides a quiet and functional space, while the finished basement offers endless possibilities for recreation or additional living areas. The extensive landscaping creates a serene outdoor sanctuary, ideal for relaxation or hosting gatherings. Practicality meets elegance with the inclusion of a full-house generator, ensuring uninterrupted comfort and convenience. Every detail of this home has been thoughtfully curated, from its modern finishes to its functional layout, offering a harmonious blend of sophistication and practicality. Discover the perfect balance of style and comfort at 21 Hemlock Hills. Schedule your private tour today to explore this exceptional property.

21 Hemlock Hills, Chappaqua

7 Quaker Lane, Chappaqua
$3,031,000
6 Beds ⋅ 5 Baths ⋅ 989064 MLS
Welcome to this timeless and stunning Colonial, sited on 1.3 beautifully landscaped, private acres. This gracious 4-Bedroom Colonial blends classic architectural details with modern amenities -- open renovated kitchen with large island w/seating, spa-like bathrooms, new windows, solar paneling, Sonos throughout, a 2-bedroom cottage over the garage for long term guests, and a stunning Shoreline pool with new pool filter and heater. Hardwood floors, walls of new windows, stunning millwork create a warm and inviting setting -- and the renovated chef's Kitchen is a showstopper. The main floor features formal and informal gathering areas with wood-burning or gas fireplaces, a newly renovated eat-in Kitchen, spacious Mudroom with Laundry area and storage, Den/Sitting area with access to the pool + back yard, a delightfully bright Home Office with custom built-in cabinetry, a wonderful Great Room with wood burning fireplace that accesses the pool and back yard and a generous-sized Dining Room with wood-burning fireplace for friends to gather. Upstairs, the Primary Suite has a newly renovated spa-like Bathroom with two vanities, steam shower and soaking tub. Three additional bedrooms and two renovated Baths complete the upstairs. Above the two-car garage (with electric car charger) is another living space -- including 2-bedrooms, sitting area, Kitchenette and a screened-in porch. The property is sublime. Flat, manicured lawns, landscaped flowering trees + shrubs and a beautiful outdoor patio all center around the Shoreline pool. A true focal point for this incredible home.

7 Quaker Lane, Chappaqua

86 Seven Bridges Road, Chappaqua
$1,375,000
3 Beds ⋅ 3 Baths ⋅ 953563 MLS
Nestled privately back from the street, this stunning residence offers a seamless blend of indoor elegance and outdoor serenity. The heart of the home is an airy, open-concept first floor anchored by a cozy wood-burning fireplace and a renovated chef’s kitchen. This level flows naturally into a bright family room with exposures on three sides. This level also opens through sliders to an expansive entertaining deck. For quieter moments, a secluded bluestone side patio provides a peaceful escape. The unique side split-level design is tailored for modern lifestyles. Just a half-flight up, you’ll find a restful primary suite and a second bedroom. One more short set of stairs leads to a massive third bedroom with a private bath—a versatile "mega-suite" that easily doubles as a quiet professional workspace or guest wing. Completing the home is a finished walk-out lower level, offering the perfect flexible space for a home gym, media room, or play area, with direct access to the two-car garage. With its blend of private outdoor extensions and dedicated living areas, this home perfectly adapts to your every need. Did we mention the automatic generator? Welcome home!

86 Seven Bridges Road, Chappaqua

14 Aldridge Road, Chappaqua
$1,345,014
4 Beds ⋅ 3 Baths ⋅ 985505 MLS
Classic 1920 Colonial brimming with vintage charm and modern updates, ideally located on a desirable cul-de-sac just a short walk to town. This beautifully maintained 4/5-bedroom home features 2 renovated full baths plus a new powder room, a sparkling white renovated kitchen with floor to ceiling cabinetry, stainless steel appliances-Sub Zero, Miele, & Viking and a generous eat-in area with door to an expansive slate patio. renovated baths throughout. Gleaming hardwood floors, graceful architectural details, a cozy fireplace add timeless appeal. The light-filled formal living room and dining room offer gleaming oak hardwood floors, crown molding and many windows. The adjacent family room or home office has windows on three exposures. The second floor features a primary suite with renovated full bath and walk-in closet plus two additional bedrooms and a renovated hall bath. The third floor offers a large bedroom, and an additional playroom/guest/office, and oak floors throughout. Set on nearly an acre (.89) of landscaped grounds with a turfed play area and flat yard, this home offers comfort and convenience inside and out. New Marvin windows, updated mechanicals, gas heat, sewer, and 3-zone heating with central air ensure year-round efficiency. Ample storage in both basement and attic, plus excellent curb appeal, a freshly painted interior & exterior, low taxes, and a prime walk-to-town location make this property an exceptional find.

14 Aldridge Road, Chappaqua

368 N Greeley Avenue, Chappaqua
$510,000
1 Beds ⋅ 2 Baths ⋅ 991421 MLS
Welcome to Chestnut Oaks, a sought-after condominium community just moments from downtown Chappaqua. This sun-filled 1-bedroom plus loft and den residence offers 5 well-designed rooms, 1.1 updated baths, and a flexible layout ideal for today’s living. The inviting entry hall features tile flooring and a generous closet, leading to an updated powder room accented by a charming octagonal window and Carrera marble floor. The renovated kitchen showcases stainless steel appliances, crisp white cabinetry, black granite countertops, and a Carrera marble subway tile backsplash, with a convenient pass-through to the dining area. The expansive living/dining room is highlighted by laminate wood flooring, recessed lighting, oversized windows, and a dramatic partial cathedral ceiling—perfect for entertaining or relaxing. Upstairs, the spacious primary bedroom includes wall-to-wall carpeting, recessed lighting, crown molding, and two double closets. An updated dual entry bath, from the hallway and primary bedroom, features gray tile flooring and a white tile tub surround. The open loft, with sliding glass doors to a private balcony, provides an ideal home office or reading nook. Additional features include a versatile den or guest space with crown molding and clerestory windows, and a convenient laundry closet with stackable washer and dryer. Enjoy complex amenities including an outdoor pool and tennis court. Ideally located close to shops, restaurants, library, park, farmer’s market, and train to NYC, this residence offers comfort, convenience, and a true Chappaqua lifestyle.

368 N Greeley Avenue, Chappaqua

65 Douglas Road, Chappaqua
$1,376,000
3 Beds ⋅ 2 Baths ⋅ 996072 MLS
The truly enchanting waterfront setting of this exceptional in-town 1930 Dutch Colonial is defined by sweeping views, lush landscaping, expansive flat yards and a pristine spring-fed duck pond. Meandering stone pathways guide you through beautifully curated grounds, revealing peaceful gathering spaces and quiet corners perfect for enjoying the storybook scenery. Just off the kitchen, a generous stone patio creates an ideal backdrop for seamless indoor-outdoor entertaining; the front porch is a classic for your rocking chairs and morning coffee. The home blends timeless craftsmanship with modern comfort, featuring a stunning gourmet kitchen, elegant French doors, central air and so much more, thoughtfully designed for effortless everyday living. Perfectly positioned in the heart of the village of Chappaqua, with no need for a car to get to everything, you’re just moments from town, shops, restaurants, and the Metro-North train station, approximately 45 minutes express train to New York City. Located in one of Westchester’s most sought-after communities, Chappaqua is known for its fabulous schools, charming downtown, scenic wooded landscapes, and outstanding quality of life. Taxes with STAR approximately $20,556. A magical home in a setting like this is a rare find, and the ability to enjoy this spectacular quality of life within steps to farmers market, gourmet food shops and restaurants, stores, train and everything you need is a dream come true.

65 Douglas Road, Chappaqua

335 Roaring Brook Road, Chappaqua
$1,080,000
3 Beds ⋅ 3 Baths ⋅ 952714 MLS
"VICTORIAN SPLENDOR" - A unique opportunity to own an early Grand Victorian home on park-like property with 3 fireplaces, a pool and a barn. Designated a New Castle George Carpenter Historic Landmark dating back to 1780. As you enter the main entrance a flood of natural light welcome you. The two-story projection of the façade’s central section, rising to a peak at the roofline, along with the hand-carved wooden banister, creates a beautifully dramatic entrance. The home possesses a special character of historic and aesthetic interest and value as part of the cultural and social history of the town. Among the most prominent features are the curved corbels or brackets under the eaves, seamlessly blending the character of its 1780 origins. Extra-tall Victorian windows still contain the original hand-blown glass, distinguished by a rippled effect in the living room, parlor and dining room adding a beautiful charm, character and workmanship that can no longer be replicated. The second floor has breathtaking library with at least 12 feet high ceilings, custom built-in bookshelves, 3 bedrooms, 2 baths and an office. Set on an acre level lot, the rear terrace overlooks a garden and pool. Do not miss this special offering.

335 Roaring Brook Road, Chappaqua

28 Valley View Road, Chappaqua
$1,455,000
3 Beds ⋅ 2 Baths ⋅ 978259 MLS
Some homes offer space. Others offer a feeling. Tucked along a picturesque tree lined street in the sought after Dodge Farm section of Chappaqua, 28 Valley View Road is a place where privacy, comfort and timeless charm come together beautifully. Privately sited on approximately 1.2 acres, framed by beautiful landscaping, mature plantings and striking stone walls, this thoughtfully designed 3 bedroom, 2 bath home offers a wonderful layout designed for everyday living and effortless entertaining. Step inside to a warm and inviting living room anchored by a wood burning fireplace, flowing seamlessly into the dining area to create comfortable gathering spaces filled with natural light and connection. One of the home's standout features is the expansive screened porch offering nearly 300 square feet of additional enjoyment, creating a seamless extension of the interior living experience. Rainy evening dinners, game nights with friends, quiet mornings with coffee or simply unwinding with a good book become moments to savor while surrounded by peaceful outdoor views. Designed for enjoyment through multiple seasons, this exceptional space brings the beauty of the outdoors closer to home. The kitchen offers timeless appeal with freshly painted solid wood cabinetry, granite countertops and a comfortable eat in area overlooking the backyard. Just outside, a private deck creates the perfect setting to enjoy morning coffee surrounded by mature landscaping and serene property views. The primary bedroom offers an ensuite bath and walk in closet, while two additional bedrooms provide flexibility for a variety of lifestyle needs. The finished walk out lower level adds over 400 square feet of versatile space featuring remarkable wide plank pine flooring reminiscent of craftsmanship rarely found today. Rich in character and warmth, the space lends itself beautifully to recreation, hobbies, workspace, fitness or gathering areas. An oversized attached two car garage offers excellent storage, while the walk up attic presents exciting possibilities for future expansion potential, offering flexibility for evolving needs. Located in the desirable Dogwood Farm area of Chappaqua, known for its peaceful setting while offering convenient access to local shopping, dining, parks, recreation and transportation options, this home presents a wonderful opportunity to enjoy space, privacy and timeless appeal in one of Northern Westchester's most sought after communities. A home designed not simply for living, but for enjoying life's quieter moments beautifully.

28 Valley View Road, Chappaqua

40 Kings Court, Chappaqua
$2,025,000
3 Beds ⋅ 3 Baths ⋅ 978528 MLS
A truly exceptional offering, this picture-perfect 1930s Colonial blends timeless elegance with modern luxury. Set on beautifully landscaped property in a serene setting yet just a moment away from town. Impeccably maintained, tastefully expanded & renovated, the home showcases refined design, effortless flow, and enduring architectural charm. The main level is thoughtfully designed with a spacious, open layout—ideal for both everyday living and entertaining. A welcoming foyer opens to a gracious living room with a fireplace and the oversized window frames the view to the back yard. The dining room flows seamlessly into the beautifully appointed chef’s kitchen, complete with a 48-inch Wolf range, Sub-Zero refrigerator, quartzite countertops, custom cabinetry, and a generous center island. Just off the kitchen, the family room offers a warm and comfortable setting for relaxing or casual gatherings. The versatile sunroom, with walls of windows and a slider to the patio is well suited for a sitting room, an office, or a play room. A mudroom with custom built-in storage, a separate laundry room, and a stylish powder room enhance the home’s effortless, well-curated lifestyle. Upstairs, this 3-bedroom home lives like a 4-bedroom, offering exceptional flexibility. The expansive primary suite is a private sanctuary with abundant natural light, a spa like bath with soaking tub, separate shower, private water closet, dual vanities, and a dressing area with two walk-in closets. Two additional bedrooms, a full bath, and an office complete the second floor. Outside the property it truly magnificent—lush, level lawn framed by mature landscaping and specimen plantings create a rare sense of privacy and tranquility . A spacious patio extends the living space outdoors, perfect for dining, entertaining, or simply unwinding while enjoying the peaceful surroundings. Ideally located just moments from town, the train and schools, this home offers an exceptional blend of timeless elegance, modern comfort, and unmatched convenience.

40 Kings Court, Chappaqua

3 Elm Street, Chappaqua
$1,175,000
4 Beds ⋅ 4 Baths ⋅ 991897 MLS
Discover this 4-bed two-family home in Chappaqua, NY, offering strong income potential, a prime village location, and excellent commuter convenience just one mile from the train. Ideal for investors or owner-occupants, this updated colonial duplex features two fully leased 2-bedroom, 2-bath units, each with approximately 1,054 square feet, private in-unit laundry, hardwood floors, covered front porches, and access to outdoor space and a shared yard. Located on a level lot on a cul-de-sac near downtown shopping, schools, and local amenities. Each unit includes separate gas and electric meters, separate gas burners for heat, separate water heaters, and tenants paying for all utilities for efficient ownership. Additional features include a private driveway with off-street parking, an unfinished walk-out basement, public sewer, public water, and natural gas service. Currently generating $6,700 per month in rental income with no vacancies, this two-family home presents a rare opportunity to own a turn-key residential income property in the Chappaqua School District.

3 Elm Street, Chappaqua

350 Wooded Hill Court, Chappaqua
$2,260,100
4 Beds ⋅ 5 Baths ⋅ 973339 MLS
Welcome to 350 Wooded Hill Court. A grand, young Colonial offering resort-style living in Chappaqua, sited on 2.9 acres. Discover the perfect blend of luxury, lifestyle, and location in this exceptional 4-bedroom, 4.5-bath set on a private cul-de-sac just minutes from town, schools, shopping, and Metro-North. Built with exquisite craftsmanship by one of Chappaqua’s most reputable builders, this home showcases superior quality, timeless detailing, and an open floor plan ideal for modern living. A striking two-story entry foyer sets the tone for the sun-filled interior, featuring Brazilian Cherry floors throughout, elegant millwork, and expansive windows framing views of the meticulously landscaped grounds. The gourmet chef’s kitchen offers top-of-the-line appliances, custom cabinetry, and seamless flow into the family room and sunroom, perfect for everyday living and entertaining. Upstairs, the luxury primary suite feels like a private retreat with a massive custom walk-in closet/dressing room complete with office space and a spa-inspired bath. Three additional spacious bedrooms and beautifully appointed baths complete the second floor. The lower level is an entertainer’s dream, featuring a state-of-the-art home theater, full wet bar, recreation space, and direct access to the yard. Step outside to your own private oasis. A breathtaking Gunite infinity-edge pool, charming gazebo, stone patios, stone walls, and specimen trees create a resort-like setting. Whether hosting summer gatherings or enjoying peaceful mornings outdoors, this property delivers unmatched indoor-outdoor living. Additional highlights in • Full-house generator • 3-car attached garage with 2 charging stations• Newer roof. Award winning Yorktown Schools.

350 Wooded Hill Court, Chappaqua

34 Turner Drive, Chappaqua
$1,955,000
4 Beds ⋅ 3 Baths ⋅ 979120 MLS
Welcome to 34 Turner Drive South -- an expanded and gracious 4-bedroom, 2-1/2 Bath, Farmhouse Colonial nestled at the end of a private drive. This special home is set on over an acre of flat, private property, surrounded by towering trees and tranquil woods. The interior features 3 fireplaces, custom millwork, hardwood floors and classic architectural details. The main level has a gracious Living Room w/wood-burning fplc, Dining Area that opens to large Family Room w/built-ins, gas fplc and French doors out to a wonderful, expansive screened-in porch; Kitchen w/large eat-in area, a third fplc and doors out to screened-in porch; Office and Powder Room. Upstairs you will find a generous-sized Primary Bedroom Suite w/large Bath and walk-in closets, three additional Bedrooms, recently renovated Hall Bath and Laundry. New Roof (2023), New Furnace (2022) and new Marvin windows throughout. A truly exceptional home.

34 Turner Drive, Chappaqua

15 Haights Cross Road, Chappaqua
$2,500,000
4 Beds ⋅ 5 Baths ⋅ 972055 MLS
A serene, light-filled retreat where modern design meets timeless comfort, this exceptional four bedroom four and one half bath contemporary residence offers an elevated lifestyle in one of Chappaqua’s most coveted settings. Set along a premier Chappaqua road on nearly three acres, the home is defined by its airy interiors, soaring ceilings, light hardwood floors throughout, and walls of windows that invite the outdoors in, framing tranquil, park-like views from nearly every vantage point. At the heart of the home, a beautifully renovated, oversized white Chef's kitchen with center island and sunlit breakfast area opens seamlessly to a dramatic family room with fireplace and multiple exposures. The main living spaces are gracious and interconnected, each oriented toward the lush, verdant grounds, offering a true indoor-outdoor lifestyle. A separate lower-level recreation or media room with direct access outside provides additional flexibility and ease. Sliding glass doors throughout lead to the yard creating an effortless flow for everyday living and elegant entertaining. The second level reveals a sophisticated primary suite with vaulted ceilings, custom built-ins, dual walk-in closets, and a spa-inspired bath. Additional bedrooms are generously scaled, complemented by a dedicated home office and versatile bonus spaces suited to today’s needs. A sweeping driveway and beautifully landscaped property enhance the home’s sense of privacy, while its location offers exceptional convenience—just moments to town, train, and top-rated schools. A rare offering that captures the essence of refined suburban living with all that Chappaqua has to offer.

15 Haights Cross Road, Chappaqua

276 Quaker Road, Chappaqua
$2,875,000
6 Beds ⋅ 4 Baths ⋅ 944162 MLS
A truly rare Chappaqua mini-estate with pool and tennis, offering resort-style living just a short walk from the town and train. Privately perched atop a hill and approached by a sweeping stone-lined driveway, this property delivers an exceptional blend of privacy, presence, and convenience—moments from shops, dining, and Metro-North. The expansive grounds are designed for all-season enjoyment, featuring a heated pool, tennis court, playground, and putting green, creating a true at-home retreat rarely available so close to town. A classic wraparound porch sets the tone for relaxed indoor-outdoor living, perfect for morning coffee, sunset cocktails, and effortless entertaining overlooking the beautifully landscaped property. The home balances estate-style scale with a warm, welcoming feel, making it equally suited to large gatherings and everyday living. An irreplaceable , country-chic Chappaqua offering where land, privacy, and best-in-class amenities meet true walk-to-all convenience—an ideal opportunity for buyers seeking a mini-estate lifestyle in a prime, in-town location.

276 Quaker Road, Chappaqua

148 Devoe Road, Chappaqua
$1,585,000
3 Beds ⋅ 3 Baths ⋅ 901089 MLS
Classic Devoe Road colonial! A covered front portico welcomes you to this timeless traditional 3-bedroom, 2.5-bath colonial-style home. The spacious living room, anchored by a wood burning fireplace and lined with custom bookshelves enjoys radiant sunshine from the oversized true divided light picture window overlooking the front of the residence. The living room adjoins the formal dining room, lined with chair rail moldings and enhanced with crown and base moldings, gleaming hard wood floors and double French doors opening to a rear deck to make alfresco entertaining effortless. The gourmet eat-in kitchen is heartily equipped with a Bosch cooktop, double in-wall ovens and dishwasher, plus a Sub-Zero refrigerator, set along natural stone countertops and complemented by a built-in buffet with glass-front display cabinets, all topped with a tin ceiling. The inviting den features high ceilings, large picture windows, built-in display cases, a flagstone floor and a sliding glass door accessing the rear deck. A neat home office with loft supports work from home or sleep/study. A powder room is discreetly tucked in the entryway. A tidy mudroom with covered exterior entry and interior garage access finishes the main level. Upstairs reside three generously proportioned bedrooms and two full bathrooms, including a front-facing bedroom with ceiling fan and hardwood flooring, and a front-corner bedroom with two exposures, ceiling fan, and wall-to-wall carpeting with hardwood flooring beneath, both of which share a rear-corner bathroom endowed with both a bathtub and a separate shower stall. The opposite corner hosts the primary suite outfitted with a wall of closets and built-ins, including a cozy window bench and a private ensuite bath. The lower level provides lots of room for recreation and utility. A rear-facing divided light picture window brings natural light into two large adjoining recreation rooms with egress from a door to the flat rear yard. A laundry closet and a utility room with a bunker-like storage closet complete the lower level. This classic 1950s home has a flat easy driveway and rare, flat-as-a-pancake yards surrounded with lush and mature landscaping. A new roof was added in 2025, as was a new Roth above-ground oil tank. The neighborhood is one of the most sought-after locations in Chappaqua with close proximity to schools and access to a sidewalk to shops, town and train. A prime offering.

148 Devoe Road, Chappaqua

33 Aldridge Road, Chappaqua
$2,621,000
5 Beds ⋅ 4 Baths ⋅ 980420 MLS
REHOBETH. A New Castle Landmark and on the National Register of Historic Places. Horace Greeley’s original stone barn, circa 1857. The first stone and cement structure built in the states converted to a residence in 1892 by one of Greeley’s daughters. They commissioned architect Ralph Adams Cram to remodel it into their house, which they named Rehoboth. Dramatic and impressive spaces with high ceilings, beams, antique wainscoting, aged and reclaimed wood floors. With over 5200 square feet of beautifully updated living space offering the perfect blend of history and today’s amenities. Original front Parlor now a Family Room. Formal Dining Room with high ceiling, original windows and fireplace. Kitchen with exposed beams, original wainscoting, aged brick walls, working island and top-of-the-line stainless appliances. Separate Breakfast Room. Remarkable Living Room with fireplace, coffered ceiling and soothing soffit lighting. Private Primary Suite with Office and Bath. Third Floor with great exposed beams and sliding barn doors housing Three additional Bedrooms. Screened Porch perfect for summer evenings. Two stone terraces set amidst beautifully landscaped grounds with wildflower meadow, rolling lawns, incredible old stone walls and established plantings. Flowering Cherry, Dogwood, Viburnum, Peonies, Hydrangeas and Rhododendrons. Very close to Chappaqua shops, restaurants, middle school and train station. A rare offering!

33 Aldridge Road, Chappaqua

12 Suzanne Lane, Chappaqua
$2,215,000
4 Beds ⋅ 3 Baths ⋅ 981166 MLS
Perfectly positioned at the end of a quiet cul-de-sac, this beautifully maintained 4-bedroom, 2.5-bath Colonial offers the ideal blend of space, comfort, and effortless living—set on expansive, level property designed for both everyday enjoyment and memorable entertaining. A gracious foyer welcomes you, seamlessly opening to the living and dining rooms and creating a natural flow for gatherings. The living room features a stunning fireplace with custom built-ins, adding warmth and character, while the generously sized dining room is perfectly situated for easy access to the kitchen. The spacious eat-in kitchen serves as the heart of the home, offering room for an office or homework station and sliders that open to a large flagstone deck with awning—perfect for outdoor dining and relaxation. The inviting family room, complete with custom built-ins and direct deck access, enhances the home’s seamless indoor-outdoor lifestyle. A powder room and first-floor laundry add everyday convenience. Upstairs, the expansive primary suite is a serene retreat, featuring a well-appointed en-suite bath, a walk-in closet, and thoughtfully designed custom built-ins. Three additional generously sized bedrooms and a hall bath complete the second level. The walk-out lower level offers a recreation area, flexible space for a gym or office, a mudroom area with cubbies, abundant storage, and access to the three-car garage. The flat, expansive backyard—easily accessed from the deck, lower level, and a charming path from the driveway—provides exceptional space for recreation, entertaining, and relaxing in complete privacy. Enjoy the ease of cul-de-sac living with close proximity to schools, shops, and the train—an exceptional opportunity to call this special home your own.

12 Suzanne Lane, Chappaqua

88 Farm Lake Crescent Road, Chappaqua
$900,000
3 Beds ⋅ 3 Baths ⋅ 978596 MLS
Welcome to 88 Farm Lake Crescent, a beautifully maintained three-bedroom, two-and-a-half-bath residence in the highly desirable Old Farm Lake community in Chappaqua. Bathed in natural light, this inviting home offers a thoughtfully designed floor plan ideal for both comfortable living and effortless entertaining. Sliding glass doors open to a private deck overlooking Farm Lake, creating a seamless indoor-outdoor lifestyle. Perfectly positioned within the community, the home enjoys both privacy and convenient access to Old Farm Lake’s exceptional amenities. The main level features a eat-in kitchen with an in-unit washer and dryer, and an open dining and living area anchored by a wood-burning fireplace—offering a warm yet modern feel. A powder room and direct access to the attached one-car garage complete this level. Upstairs, two bedrooms share a hall bath, while the primary suite features a spacious walk-in closet and full bath. Peaceful lake views make this a truly special retreat. The finished lower level provides valuable additional living space—ideal for a family room, home office, gym, or guest area—with sliding glass doors leading to a private outdoor setting, offering exceptional flexibility for today’s lifestyle. Located less than one mile from Chappaqua’s vibrant village and the Metro-North Railroad train station, this home offers the perfect blend of privacy, convenience, and lifestyle.

88 Farm Lake Crescent Road, Chappaqua

6 Killington Street, Chappaqua
$1,609,031
4 Beds ⋅ 3 Baths ⋅ 952785 MLS
Dreamy modern ranch nestled on a private landscaped acre on a cul-de-sac in sought-after Whippoorwill. A flagstone walkway leads to a covered entry. The contemporary-styled front door with cross-reed glass panels and sidelight sets a refined first impression. Designed for effortless indoor/outdoor living, the rear-facing living room anchors the home with a wood-burning fireplace and two sets of French doors opening to a wrap-around Trex deck. Designer Runtal vertical panel hydronic radiators add comfort and style to the space. The sleek kitchen is outfitted with electric Thermador double wall ovens, a built-in Thermador microwave, Jenn-Air cooktop, panel-finished Sub-Zero refrigerator and freezer, Bosch dishwasher, custom cabinetry with under-cabinet lighting, narrow glass subway tile backsplash, and granite countertops. A dining area adjoins the kitchen and living room. A private corner office with built-ins enjoys sweeping views from walls of windows and a French door to the deck. Private quarters are composed of four comfortably sized bedrooms, including a primary with ensuite bath and a hall bath with shower over bathtub. The finished walk-out lower level delivers a generous family room with custom built-ins and a sliding glass door to a covered patio; a large, finished laundry room with built-ins, sink and space for arts and crafts; a powder room plus access to the oversized two car garage. Natural gas fuels the heat, hot water and the Generac 22kW automatic backup generator. Finishing touches include blown-in insulation, modern metal cable railing surrounding the deck, and a Trex RainEscape system underneath to keep the covered patio dry. Nice sized lawns for play or relaxation front and rear with a fenced rear yard. Mature and established landscaping highlighted with andromeda, holly, blue spruce, and arbor vitae. Near Horace Greeley High School, the shops and amusements at Chappaqua Crossing, the Town of New Castle’s Whippoorwill Park, and the noted, private Whippoorwill Club.

6 Killington Street, Chappaqua

39 Mayberry Road, Chappaqua
$1,550,000
4 Beds ⋅ 3 Baths ⋅ 973483 MLS
Set privately on 2+ acres at the end of a quiet cul-de-sac, this beautifully updated 4-bedroom ranch lives like a 5-bedroom home and offers the perfect blend of comfort, flexibility, and style. Enjoy distant western sunset views and direct access to the adjacent Pruyn Sanctuary, creating a serene, nature-connected setting while still being part of a neighborhood. The heart of the home is the renovated eat-in kitchen, featuring stainless steel appliances, inset cabinetry, and striking quartzite countertops. It opens seamlessly to a generous breakfast room with vaulted ceilings, walls of windows, and access to the deck—ideal for everyday living and entertaining. The adjacent family room with fireplace provides a warm and inviting gathering space, while the formal many -windowed living and dining rooms offer timeless appeal. The expansive primary suite is a true retreat, complete with vaulted ceiling, a fireplace with custom concrete floor to ceiling beach-wave surround, full-light glass doors to a private patio, a walk-in closet plus 2 additional double closets, and a dressing area with custom built-ins. The spa-like en-suite bath features a steam shower and double sinks with storage vanity and Kohler fixtures. Three additional bedrooms, a home office, and two renovated hall baths complete the main level. The walk-out lower level offers exceptional additional living space with sliding glass doors, including areas for play, media, and a gym, a summer kitchen with granite counters and wood cabinetry, along with abundant closets, a separate laundry room, utility room, and a large storage room. There is a mud room area with built-ins and direct access to a large 2-car garage. Additional highlights include oak floors, 5-zone HVAC, whole house generator, 12-zone sprinkler system, and a flat, fenced yard area. Ideally located close to schools, train, and shops, this home offers a flexible layout, excellent condition, and a truly special setting with patio and bilevel deck, areas for play, gardens and dramatic rock outcroppings.

39 Mayberry Road, Chappaqua

52 Whippoorwill Lake Road, Chappaqua
$2,215,000
4 Beds ⋅ 3 Baths ⋅ 983438 MLS
Welcome to this fabulous 4-bedroom, 2.5-bath contemporary Colonial home, perfectly designed for today’s lifestyle with a seamless blend of style and comfort. Set on 2.26 private acres with vast views of the private community lake, this home offers open, luminous living spaces flooded with natural light and thoughtful architectural detail throughout. As you enter the home, you step into the formal living room featuring sliding glass doors to deck, a wood-burning fireplace and floor to ceiling windows that frame the surrounding landscape and bathe the room in sunlight. The formal dining room with balcony provides a large space for entertaining, while the flowing layout ensures effortless movement between spaces. The gourmet eat-in kitchen with center island is steps away from the family room, fireplace, and screened in porch. The primary bedroom suite offers privacy and separate home office with three walls of windows looking over the backyard and lake. Three additional bedrooms and full bathroom complete the second floor. The large private property is ideal for fun outdoor activities, stroll to the lake to kayak or quiet evenings at home. There is more to enjoy when you live in Chappaqua, from the award winning school district, dining in town, convenient metro-north trains, and preserve hiking trails. We have it all for you!

52 Whippoorwill Lake Road, Chappaqua

25 Longview Lane, Chappaqua
$1,620,000
4 Beds ⋅ 4 Baths ⋅ 976221 MLS
Tastefully updated and well maintained, this sophisticated yet traditional Contemporary home offers the perfect balance of elegance and comfort in the highly sought-after Chappaqua school district. The light-filled, open floor plan welcomes you with spacious rooms, soaring ceilings, and a floor-to-ceiling stone fireplace anchoring the dramatic great room. The expansive eat-in kitchen is a chef’s delight, featuring SubZero and Thermador stainless appliances, granite counters, and sliders that open to a wraparound IPE deck, ideal for seamless indoor-outdoor living and entertaining. Enjoy the outdoor stone grill and take in the tranquil natural surroundings that define this special property. Beautiful Brazilian cherry floors and thoughtful architectural details highlight the home’s craftsmanship. The second level of the home has four big bedrooms, two full baths (one en-suite) and a large walk-in cedar closet. The expansive walkout lower level has a large playroom, office, full bath and huge storage area. Situated on a private cul-de-sac, this residence blends the serenity of a bucolic, wooded setting with the convenience of a neighborhood location close to schools, town, and train. Freshly painted inside and out in 2026, with underground utilities and above-ground oil tank, this turn-key home is ready to move in and enjoy. A wonderful Chappaqua offering—private, refined, and welcoming.

25 Longview Lane, Chappaqua

5 Grove Mews, Chappaqua
$799,000
2 Beds ⋅ 3 Baths ⋅ 969052 MLS
All the space and privacy of a single-family home with the ease of condo living! One of the few completely stand-alone and private townhouses in Apple Hill Farm, this spacious 2-bedroom, 2.5-bath home offers a rare blend of comfort, style, and convenience. Enjoy the serene setting from a large wrap-around wood deck overlooking lush, wooded views—perfect for morning coffee or evening entertaining. Inside, the sunny living room features a cozy wood-burning fireplace, oversized windows, and flows seamlessly into the formal dining area with sliding glass doors to the deck. The updated kitchen boasts custom cabinetry, brand-new stainless steel appliances, and its own access to the deck ideal for grilling or gatherings. All bathrooms have been newly and tastefully renovated with quartz vanities and striking tile flooring, bringing a luxurious feel throughout. Additional highlights include wood floors throughout, many new windows, a new roof and skylights (2019), and a new driveway and cul-de-sac (2019). Storage is plentiful with large closets, a pull-down attic, crawl space, and an attached garage. Apple Hill Farm is a private, tranquil community offering a pool and tennis courts, all just minutes from town, train, and top-rated Chappaqua schools. This move-in-ready home offers it all—privacy, space, and low-maintenance living in a coveted location.

5 Grove Mews, Chappaqua

4 Wright Drive, Chappaqua
$1,750,000
3 Beds ⋅ 3 Baths ⋅ 966982 MLS
A rare opportunity to own one of the few true 3-bedroom townhomes in Chappaqua Crossing Carriages, a sold-out luxury community within the highly sought-after Chappaqua School District. With all three bedrooms ideally situated on the second floor — a layout rarely available here — this exceptional end unit combines smart design with high-end finishes and extensive upgrades throughout. The main level offers a welcoming entry foyer with a versatile formal living room and powder room near the entrance, ideal as a sitting room, second office, or flex space. The heart of the home is the chef’s kitchen with custom cabinetry, premium appliances, waterfall quartz island, and pantry, open to the dining area and family room with gas fireplace. A two-car garage connects to a custom mudroom with built-in cubbies, bench, and closet. Upstairs includes three bedrooms, a dedicated home office, and a second family room with wet bar and wine refrigerator with large sliding glass doors to a large covered private terrace. The primary suite features a modern tray ceiling, a walk-in closet and spa-like bathroom with a double-sink vanity, oversized shower, and private toilet room. A hall bath with double sinks and a second-floor laundry room complete the level. Additional highlights include 12-foot ceilings, oversized windows, quartz countertops throughout, abundant storage, whole-house air filtration, and a full unfinished basement with plumbing and egress for future expansion. Community amenities include a clubhouse with gym, entertaining spaces, outdoor pool, shuttle to the Chappaqua train station, and walkable access to shopping, dining, Whole Foods and Life Time Fitness.

4 Wright Drive, Chappaqua

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

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