Chappaqua, New York

Chappaqua NY Real Estate & Community Guide

A local guide to Chappaqua homes, New Castle property details, school district considerations, Metro-North access, acreage, luxury pricing, and selling strategy.

Explore what buyers and sellers should understand before making a move in one of northern Westchester’s most recognized residential markets.

View Chappaqua Listings Call or Text Tierra
Advanced Search Market Report Home Value Connect

Chappaqua Local Insight

Understanding the Chappaqua Real Estate Market

Chappaqua is a hamlet within the Town of New Castle, and real estate searches here often overlap with broader New Castle considerations. Buyers may compare Chappaqua for school district, Metro-North access, residential setting, larger homes, land, privacy, and proximity to Mount Kisco, Pleasantville, Armonk, Bedford, and Briarcliff Manor.

For sellers, Chappaqua homes need careful positioning because value can vary by neighborhood, acreage, condition, taxes, school-district details, commute access, renovation level, and whether buyers are comparing the property with nearby northern Westchester markets.

Market Snapshot

A recognized northern Westchester market where property details matter.

Municipality: Chappaqua is part of the Town of New Castle.

Housing: Colonials, renovated homes, larger single-family properties, townhome-style options, and select estate properties.

Transit: Chappaqua station connects to Metro-North’s Harlem Line.

District: Chappaqua Central School District, including Horace Greeley High School.

Best approach: Compare by location, condition, taxes, acreage, commute access, school district, and current competition.

Search Patterns

Chappaqua Is Not One Single Property Type

Chappaqua searches can include renovated homes near town, larger properties with acreage, older homes with architectural character, newer construction, townhome-style options, and homes that buyers compare with nearby northern Westchester communities.

Near Town & Train

Some buyers focus on access to the village center, train station, local shops, and daily convenience.

Acreage & Setting

Larger properties should be reviewed for usable land, privacy, maintenance, driveway access, and long-term care.

Renovated Homes

Updated kitchens, baths, systems, windows, roof, mechanicals, and layout can strongly affect buyer response.

Townhome Options

Some buyers compare lower-maintenance attached options, especially when reviewing monthly costs and community rules.

Price Context

What Can You Buy in Chappaqua?

Chappaqua pricing can vary widely by property type, condition, acreage, taxes, location, school-district details, and current inventory. The categories below are general search lanes, not fixed price promises.

Entry Points

Select Smaller Homes

Entry points may include smaller single-family homes, older homes needing work, or attached options depending on inventory.

Core Single-Family

Condition Drives Value

Most buyers compare updates, room flow, systems, taxes, yard usability, and proximity to town or train.

Renovated Homes

Move-In Appeal

Homes with updated systems, kitchens, baths, layout, and exterior care may command stronger buyer attention.

Acreage

Land & Maintenance

Larger properties should be reviewed for terrain, privacy, drainage, driveway length, and long-term upkeep.

Luxury

Higher-End Properties

Luxury homes may involve larger lots, pools, guest spaces, custom finishes, privacy, and specialized buyer expectations.

School District Overview

Chappaqua Central School District

Chappaqua homes are commonly associated with Chappaqua Central School District. The district lists three elementary schools serving Kindergarten through Grade 4, two middle schools serving Grades 5 through 8, and Horace Greeley High School serving Grades 9 through 12.

School information should always be verified by property address. Buyers should review district resources, transportation, enrollment details, and any program questions before relying on a listing headline or mailing address.

Quick School Notes

District: Chappaqua Central School District

Elementary: Grafflin, Roaring Brook, and Westorchard Elementary Schools

Middle: Bell and Seven Bridges Middle Schools

High school: Horace Greeley High School

Blog note: School culture, academic identity, athletics, alumni, and private-school comparisons can be expanded in supporting blog content.

NorthStone Perspective

In Chappaqua, Details Explain the Value

Buyers may see two homes with similar bedroom counts and very different values. Condition, renovation quality, taxes, lot usability, school district, commute access, neighborhood, and current competition all matter.

Town vs Hamlet

Chappaqua is part of New Castle, so buyers should confirm municipality, property records, services, taxes, and district details.

Lot Usability

Acreage should be reviewed for slope, wetlands, drainage, driveway access, play space, privacy, and maintenance.

Systems & Updates

Roof, windows, mechanicals, septic, well, generator, drainage, and renovation history should be reviewed early.

Commute Fit

Train access, station parking, parkway access, school travel, and daily routines can affect buyer interest.

Commute & Daily Logistics

Train Access, Roadways, and Daily Convenience

Chappaqua station is part of Metro-North’s Harlem Line, and train access is often a major part of the search. Buyers may also compare parkway access, local roads, school travel, shopping, dining, parks, and daily errands.

For sellers, those logistics should be clear. A property near town, close to the station, convenient to schools, or easier to reach from major roads may appeal to different buyers.

Details Buyers Often Review

Train access: Chappaqua station serves Metro-North’s Harlem Line.

Road access: Buyers may compare proximity to the Saw Mill River Parkway, Taconic State Parkway, I-684, and local roads.

Daily errands: Proximity to town, parks, restaurants, shopping, and nearby communities can influence fit.

Property logistics: Driveway access, snow removal, landscaping, and system maintenance can affect day-to-day planning.

Buyer Guidance

What Buyers Usually Compare in Chappaqua

Chappaqua buyers often need to compare more than price. Property condition, acreage, taxes, school-district details, commute access, systems, maintenance, and nearby alternatives can all change the decision.

Location

Near-town, near-train, larger-lot, cul-de-sac, and more private settings may appeal to different buyers.

Acreage

Land should be reviewed for usability, slope, drainage, privacy, driveway access, and maintenance.

Systems

Septic, well, roof, heating, cooling, generator, drainage, and electrical systems can affect confidence.

Taxes

Property taxes are a major part of the full ownership picture and can affect affordability and offer strategy.

Condition

Updates, layout, roof age, major systems, exterior care, and renovation needs can shift value quickly.

Nearby Markets

Buyers may compare Chappaqua with Pleasantville, Mount Kisco, Armonk, Bedford, Briarcliff Manor, and North Castle-area options.

For Chappaqua Homeowners

Selling a Home in Chappaqua

A Chappaqua listing should explain the full value story clearly. Buyers need to understand the home, the land, the updates, the commute options, the tax picture, and how the property compares with other northern Westchester options.

Price With Context

Pricing should reflect recent sales, location, condition, taxes, updates, acreage, systems, and current competition.

Prepare the Details

Floor plans, permits, renovation history, system ages, exterior care, septic, well, and maintenance records can affect buyer confidence.

Launch With Clarity

Strong listing copy should explain setting, updates, layout, commute access, schools, taxes, and practical buyer considerations.

Important Property Detail

Verification Matters in Chappaqua

Chappaqua properties can involve larger lots, older homes, private systems, renovation history, school-district questions, and New Castle property records. Buyers should review the details behind each listing before relying on photos or broad search filters alone.

Before relying on a search result, verify:

Municipality, school district, and property records

Property taxes, assessments, and exemptions

Septic, well, permits, certificate of occupancy, and major systems

Acreage usability, wetlands, drainage, and driveway access

Renovations, exterior maintenance, generators, pools, and outbuildings

Chappaqua Homes for Sale

View Current Chappaqua Listings

Use the Chappaqua listings page to review active homes, compare property styles, and begin narrowing down which options may fit your search criteria.

Because Chappaqua properties can vary by location, acreage, systems, taxes, condition, school-district details, and commute access, it is helpful to review each listing carefully before relying on broad search filters alone.

Search Chappaqua Homes Ask Tierra About a Listing

For Chappaqua Homeowners

Curious What Your Chappaqua Home Could Be Worth?

A home value estimate is a helpful starting point, but the real number depends on location, property type, acreage, condition, updates, taxes, systems, recent comparable sales, competing inventory, and current buyer demand.

Start With Home Value

Chappaqua Real Estate FAQ

These are common questions buyers and sellers ask when comparing Chappaqua homes, acreage, taxes, commute options, school-district details, and nearby communities.

Is Chappaqua a town or a hamlet?

Chappaqua is a hamlet in the Town of New Castle. Buyers should verify municipality, school district, taxes, and property records for each listing.

What ZIP code is associated with Chappaqua?

Chappaqua is commonly associated with ZIP code 10514. ZIP code alone does not confirm school district, taxes, or property-specific details.

Does Chappaqua have Metro-North access?

Yes. Chappaqua station is part of Metro-North’s Harlem Line. Commute convenience depends on property location, station access, parking, schedule, and daily travel needs.

What school district serves Chappaqua homes?

Many Chappaqua homes are associated with Chappaqua Central School District, but buyers should verify school-district assignment by property address before relying on a listing headline or mailing address.

What types of homes are common in Chappaqua?

Chappaqua can include Colonials, renovated homes, older homes, larger single-family properties, estate-style homes, townhome-style options, and select new construction depending on inventory.

What should buyers review when purchasing acreage in Chappaqua?

Buyers should review usable land, slope, wetlands, drainage, driveway access, septic, well, exterior maintenance, surveys, permits, and long-term care needs.

What should sellers know before pricing a Chappaqua home?

Sellers should review recent sales, location, acreage, condition, taxes, systems, renovations, school-district details, buyer demand, and nearby competing listings before setting a price.

What nearby communities do buyers compare with Chappaqua?

Buyers often compare Chappaqua with Pleasantville, Mount Kisco, Armonk, Bedford, Briarcliff Manor, North Castle-area options, and other northern Westchester markets.

How can I find out what my Chappaqua home is worth?

The best starting point is a property-specific value review that considers recent sales, location, acreage, condition, taxes, systems, buyer demand, and competing listings.

Continue Exploring

Related Resources

Use these guides to compare listings, review the market, or start with a property-specific home value review.

Search Chappaqua Homes

Review current Chappaqua listings and compare homes by location, acreage, condition, property type, taxes, and key details.

View Listings →

Chappaqua Market Report

Review current Chappaqua market data, active inventory, recent sales, pricing patterns, and local housing trends.

View Market Report →

Home Value Review

Start with a property-specific value review before relying on automated estimates or broad market averages.

Request Home Value →

Meet Your Realtor

Tierra Stanback

Licensed Real Estate Salesperson • SRES • eXp Realty Luxury

Whether you are comparing Chappaqua homes, preparing to sell, reviewing your home value, or trying to understand how your property fits today’s market, my goal is to help you make a confident next move with clear local guidance.

Call or Text Tierra

Local Knowledge • Practical Guidance • Let’s Make the Move.

$1,100,000
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
$950,000
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
$1,590,000
3 Beds ⋅ 3 Baths ⋅ 1017997 MLS
Enter into this enduring Colonial blending elegance with today's lifestyle. This home lives like a 4-bedroom and has 4 BR septic. Set on beautifully landscaped property moments away from town, the train and Chappaqua schools. Tastefully expanded and renovated in 2008, this home showcases classic architectural details everywhere. A welcoming foyer opens to a gracious living room and fireplace. A formal dining room with a tray ceiling. Timeless appointed chefs EIK with Wolf appliances, custom cabinetry and marble counter tops, wine refrigerator and breakfast bar. The family room offers a second fireplace and a wall of windows to view the private setting. The sunroom offers custom built-ins and an abundance of natural light. A first floor bonus room and full bathroom works well for guests or an au pair. A mudroom with custom built-ins. Upstairs is the primary bedroom with high ceilings, walk-in custom closet, private study, and en-suite bath with double sinks, marble shower and whirpool bath. Two additional bedrooms, one with custom built-ins, custom closets, and a hall bath. New laundry is located conveniently on the second floor. Outdoors, an expansive deck extending the living space and creating the perfect setting for entertaining, dining and relaxing while overlooking mature landscaping and private grounds that back up to protected green space. Completing the property is a detached two car-garage with generous storage above. The home was extensively renovated and expanded in 2008 offering the finest architectural finishes. An exceptional offering. New roof 2024 and new 4 bedroom septic 2026.

131 Douglas Road, Chappaqua
$1,594,000
3 Beds ⋅ 3 Baths ⋅ 1013791 MLS
Renovated and Reimagined Colonial on Spectacular Park-Like Grounds, this exceptional residence includes a separate cottage-style bonus building that offers endless possibilities. Whether envisioned as a private home office, artist’s studio, yoga or fitness center, man cave or an inspiring creative workspace, this detached structure provides exceptional flexibility and privacy. Nestled amid the lush grounds and mature landscaping, it serves as a peaceful extension of the home and creates a rare opportunity for today’s work-from-home lifestyle or entrepreneurial pursuits. At the heart of the home, an original stone wood-burning fireplace serves as a stunning focal point, infusing the living space with warmth, character, and timeless charm. Perfect for cozy winter evenings, holiday celebrations, and memorable gatherings with family and friends, this impressive architectural feature creates an inviting atmosphere that embodies the true spirit of home. The stunning chef’s kitchen features premium stainless-steel Thermador appliances, elegant quartz countertops, a spacious walk-in pantry, and seamless access to an oversized slate patio—ideal for indoor-outdoor entertaining. The captivating primary suite offers soaring beamed ceilings, a generous sized walk-in closet, and a luxurious spa-inspired bath complete with dual vanities and a classic clawfoot soaking tub. Convenient second-floor laundry with storage enhance everyday living. Additional highlights include all-new Anderson windows, all new electrical, all new plumbing, new roof, new c/air, new Navien system, energy-efficient blown-in insulation, solid wide-plank oak flooring, and exquisite custom millwork throughout. The separate cottage building has all new electrical, blown insulation, windows, flooring and roof. Located minutes from the Metro North Train Station and downtown Chappaqua, you'll have quick access to commuter routes and a charming village filled with shopping, restaurants and community events. A rare offering that perfectly blends timeless charm with sophisticated modern updates, all set within a serene and private setting. The outbuilding / studio can be converted back to a garage. Square footage does not include the studio space.

676 Hardscrabble Road, Chappaqua
$869,000
3 Beds ⋅ 3 Baths ⋅ 1006886 MLS
Welcome to Apple Hill Farm, sitting on highly desirable, 37+ Wooded Acres. Where calm meets comfort. This corner Townhome, located in a cul-de-sac for added privacy, features a manicured lawn and a carefully curated garden. Experience modern elegance in this home, with high ceilings, lots of Windows and Skylights that bring abundant natural daylight and sunlight indoors. It has 3 Bedrooms and 2.5 Bathrooms, many updates throughout the home, including the exterior deck. The Living Room has custom built-ins. An inviting Dining Room for memorable meals and an Eat-in-Kitchen with quartz countertops and stainless steel appliances, both rooms have sliding doors onto the deck. It features hardwood floors throughout, many closets and storage spaces. The Primary Bedroom has a Juliet Balcony, En-Suite bathroom with Double sink vanity, Second Bedroom with Skylights, Third Bedroom with Hallway Bathroom. Close to Train, Close to Downtown Dining and Shops, Close to Schools. Property includes 1-Car Attached Garage with Driveway for 1 additional car. Amenities include: Inground Pool and Tennis Courts.

2 Timberland Pass, Chappaqua
$2,649,000
4 Beds ⋅ 5 Baths ⋅ 998577 MLS
Tucked away on over two exquisitely landscaped acres in one of Chappaqua’s most prestigious enclaves, this exceptional newly constructed modern home redefines luxury living through a masterful blend of architectural sophistication, cutting-edge efficiency, and timeless elegance. Designed with a discerning eye and crafted with uncompromising quality, this magazine-worthy residence offers the ultimate turnkey lifestyle only moments from downtown Chappaqua, Metro North, and top-ranked schools. A dramatic arrival sets the tone as you enter through oversized custom doors into sun-drenched interiors framed by soaring 10-foot ceilings, expansive walls of glass, and wide-plank white oak flooring throughout. The home’s seamless open-concept design was thoughtfully curated for both grand-scale entertaining and intimate everyday living, creating a warm yet elevated atmosphere in every room. At the heart of the home is a spectacular chef’s kitchen worthy of a luxury design showroom, featuring premium professional-grade appliances, bespoke custom cabinetry, oversized quartzite island, designer lighting, and exceptional prep and storage space. Flow effortlessly into the breathtaking great room anchored by a statement fireplace and oversized sliders that open to a covered outdoor lounge, creating a true indoor-outdoor living experience. The primary suite is a private sanctuary rivaling a five-star resort, complete with a boutique-inspired dressing room and a spa-caliber bath featuring radiant heated floors, custom marble steam shower, soaking tub, and designer vanities. Generously sized ensuite bedrooms provide exceptional comfort and privacy for family and guests alike. The fully finished walk-out lower level elevates the home even further, offering an extraordinary extension of living space ideal for a private wellness retreat, gym, media lounge, golf simulator, wine tasting room, or entertainment venue. A striking custom wine display serves as a dramatic focal point and conversation piece. Every inch of this residence reflects a commitment to luxury and modern convenience, including geothermal heating and cooling, smart-home integration, premium fixtures and finishes, oversized heated garage space, and meticulously curated landscaping designed for both beauty and privacy. A rare offering that blends modern elegance, privacy, and convenience just under an hour from Manhattan. Come see a flawless fusion of contemporary design, superior craftsmanship, and effortless luxury set within one of Westchester’s most coveted communities today.

40 Hamilton Drive, Chappaqua
$849,999
4 Beds ⋅ 2 Baths ⋅ 996830 MLS
NOW Easy to Show Welcome to this beautifully maintained raised ranch offering the perfect blend of space, comfort, and convenience in a highly desirable Chappaqua P.O. location within the award-winning Pleasantville School District. Situated on a quiet cul-de-sac, this 4-bedroom, 2-bath home features soaring cathedral ceilings, rich red oak hardwood floors, and an inviting open layout designed for both everyday living and entertaining. The spacious living room provides the ideal setting for gatherings and holidays, while multiple freshly stained multi-level decks create seamless indoor-outdoor living perfect for entertaining, summer barbecues, or relaxing evenings overlooking the expansive park-like property. The large yard offers endless possibilities for play, gardening, and recreation, plus three storage sheds for added convenience. Also included is a 11'x54' triangular shaped lot on north side of primary lot. .46 Acre Total Recent updates including a newer roof and boiler provide peace of mind, while the attached garage adds practicality and storage. Commuters will love the easy 5-minute walk to the Chappaqua train station with approximately 45-minute access to Grand Central Terminal. Rarely offered, this home also includes FREE school bus pickup within Pleasantville’s walking district. Ideally located just minutes from the farmers market, shops, restaurants, parks, and Metro-North, this move-in ready home delivers comfort, charm, and an exceptional lifestyle in one of Westchester’s most sought-after communities. Easy to show same day showings are ok now.

249 Mill River Road, Chappaqua
$2,249,000
3 Beds ⋅ 4 Baths ⋅ 973551 MLS
Set on beautifully landscaped grounds in one of Chappaqua’s most coveted neighborhoods, this exceptional luxury Colonial blends timeless architecture, designer finishes, and an unmatched indoor-outdoor lifestyle within the award-winning Chappaqua school district. Privately positioned against acres of preserved land, this premier Westchester County property offers both tranquility and convenience, just minutes to Metro North, downtown Chappaqua, and Chappaqua Crossing featuring Whole Foods Market and Life Time. Living like a 5-bedroom home, this luxury home for sale in Chappaqua showcases exceptional craftsmanship throughout with Juliet balconies, copper-topped cupolas, Belgian block-lined driveways, soaring ceilings, custom millwork, and walls of glass that flood the interiors with natural light. A dramatic curved staircase welcomes you into elegant yet comfortable living spaces designed for both everyday living and sophisticated entertaining. The chef’s kitchen is beautifully appointed with premium Wolf and Sub-Zero appliances, custom cabinetry, and European mosaic tilework, seamlessly connecting to the formal and casual gathering spaces. Highlights include a sophisticated library with gas fireplace, a stunning vaulted family room, and an impressive entertainment lounge with a wood-burning fireplace, wet bar, Viking wine refrigerator, and custom built-ins. The luxurious primary suite offers a gas fireplace, oversized dressing room, and spa-inspired bath, delivering the ultimate private retreat. Outside, the property lives like a private resort with a heated saltwater pool, outdoor fireplace, expansive patios, built-in grill, fire pit, poolside grotto with shower and changing area, gazebos, and a half basketball court with spotlighting. This exceptional Chappaqua estate offers luxury living, privacy, and resort-style amenities in one of Westchester’s most sought-after communities, known for top-rated schools, vibrant downtown, and easy NYC commute. A rare opportunity to experience estate-style living and the quintessential Chappaqua lifestyle at its finest.

33 Greenbriar Drive, Chappaqua
$1,590,000
3 Beds ⋅ 4 Baths ⋅ 984583 MLS
Welcome to this sophisticated carriage home at 17 Lila Lane, offering a rare blend of contemporary luxury and maintenance-free living within the prestigious Chappaqua Crossing community. The thoughtfully designed layout is anchored by a gorgeous chef’s kitchen, featuring a large center island with ample seating and a premium JennAir appliance package. Equally enticing is the coveted first-floor primary suite, providing a serene sanctuary with a spa-inspired ensuite bathroom and an expansive walk-in closet. The second level serves as a versatile retreat, home to a spacious second bedroom, a dedicated home office/bedroom, an inviting sitting area, and a gorgeous private terrace. Additional living space abounds in the fully finished lower level, perfectly suited for a high-end home gym and a cozy media den, while the attached two-car garage comes equipped with an EV charging station for modern convenience. Residents enjoy an unparalleled "village within a village" lifestyle defined by sprawling green space and scenic walking trails, with exclusive access to a luxury clubhouse and sparkling pool. Situated in the heart of Chappaqua, this residence is just steps from Whole Foods, Life Time Fitness, delicious restaurants, and offers the convenience of a private community shuttle to the Metro-North for a seamless commute to Manhattan.

17 Lila Lane, Chappaqua
$809,000
4 Beds ⋅ 3 Baths ⋅ 981423 MLS
Welcome home to this well-maintained residence in the heart of vibrant Chappaqua! This 4 bedroom and 2.5 full bathroom house is located in the award-winning Chappaqua school district. Step inside to discover gleaming hardwood floors throughout, a cozy living room with a wood-burning fireplace, and a bright, charming dining room. The kitchen features ample cabinetry, granite countertops, and brand-new stainless-steel appliances. The spacious primary suite, versatile enough to serve as a large family room, includes a walk-in closet and a newly renovated en-suite bathroom. Upstairs, three generously sized bedrooms await, including a second primary suite with a walk-in closet, and a second full bathroom. Additional highlights include a welcoming front porch, expansive attic storage, a full basement with crawl space, and a circular driveway accommodating up to six cars for effortless access. Enjoy summer days in the fenced backyard—perfect for gatherings, gardening, or basking in the sunshine. This prime location is minutes from the Train Station, library, town hall, post office, shops, restaurants, top-rated schools, and easy access to major parkways. Zoned for versatility, this property offers a potential for conversion back to commercial use, for an attorney’s office, dental practice, or other professional ventures in the bustling heart of Chappaqua. Don’t miss your chance to own this delightful home with endless possibilities! The house is no longer furnished as shown in the photos.

73 S Bedford Road, Chappaqua
$4,500,000
5 Beds ⋅ 7 Baths ⋅ 950756 MLS
1906 Grandeur. 2026 Luxury: The Ultimate Gated Sanctuary. Perched majestically atop a private hilltop, this gated 7,800-square-foot, five-bedroom estate presents a rare convergence of Gilded Age prestige and contemporary luxury. Believed to have been commissioned in 1906 for railroad magnate A.H. Smith, the residence has been masterfully renovated to honor its historic soul, featuring original interior stone walls and soaring ceilings that strike a perfect balance between grand scale and intimate warmth. Anchored by three distinctive hearths, the home is designed for both elegant living and everyday ease. A sun-drenched chef’s kitchen showcases a central island, dramatic overhead skylight, and professional-grade appliances. Unique architectural moments—including a circular-skylit Stargazer’s Nook—add character and charm, while the versatile five-bedroom layout offers both a magnificent two-story primary wing and a coveted first-floor private suite. Set on more than four exceptionally private acres, the grounds unfold as a true outdoor sanctuary, featuring a beautiful pool and spa (32x20), refined pergola terraces ideal for entertaining, and a private tennis court. From its commanding hilltop position, the estate delivers an unparalleled sense of privacy, security, and timeless elegance. Welcome home!

150 Old Farm Road N, Chappaqua
Start Your Search

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.