Chappaqua, NY Homes for Sale: Your Guide to Exceptional Westchester Living

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Discover an exquisite selection of homes for sale in Chappaqua, NY, a highly sought-after hamlet in Westchester County known for its prestigious schools, picturesque landscapes, and vibrant community. Tierra Stanback presents a diverse portfolio ranging from charming historic residences to modern luxury estates, catering to discerning buyers seeking a tranquil yet connected lifestyle. Explore available properties, understand local market trends, and find your ideal Chappaqua home, whether you desire a spacious family abode near top-rated schools or a secluded retreat amidst nature's beauty. Chappaqua's unique blend of suburban tranquility and convenient access to NYC makes it a premier destination for those seeking exceptional living.

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Exploring Chappaqua's Diverse Real Estate Market

The array of homes for sale in Chappaqua, NY, presents an incredible opportunity for discerning buyers seeking a blend of sophistication and suburban comfort. This picturesque hamlet, nestled within New Castle in Westchester County, boasts a dynamic real estate landscape.

Luxury Homes and Estates in Chappaqua

For those seeking unparalleled elegance, Chappaqua offers a remarkable selection of luxury homes and expansive estates. These properties often feature sprawling acreage, custom architectural designs, and high-end amenities, providing privacy and opulence. Many luxury listings showcase gourmet kitchens, home theaters, and private pools, reflecting the affluent lifestyle synonymous with this area.

Family-Friendly Homes Near Top Chappaqua Schools

A significant draw for families exploring homes for sale in Chappaqua is the highly-regarded Chappaqua Central School District, including the prestigious Horace Greeley High School. Buyers frequently seek single-family homes situated in close proximity to schools, offering convenience and a strong sense of community. These properties often feature spacious yards, multiple bedrooms, and family-oriented layouts, ideal for raising children.

Historic Charm and Modern Residences

Beyond contemporary luxury, the Chappaqua real estate market also includes charming historic homes, many meticulously maintained and updated. These residences often tell a story, featuring unique architectural details from bygone eras. Conversely, new construction homes are also available, offering modern design, energy efficiency, and the latest smart home technology to suit contemporary tastes.

Chappaqua Neighborhoods: Finding Your Perfect Place

Understanding Chappaqua's distinct neighborhoods is key when searching for the ideal home. Each area offers a unique ambiance and property style.

Whippoorwill: Secluded Estates and Privacy

The Whippoorwill section is renowned for its larger properties and a heightened sense of seclusion. Here, residents find magnificent estates set on generous parcels of land, often bordered by natural woodlands. These homes for sale appeal to those prioritizing privacy and expansive outdoor living.

Quaker Street Area: Classic Homes and Community Feel

The Quaker Street area is cherished for its classic Chappaqua homes, often Colonials or Victorians, situated on well-manicured lots. This neighborhood fosters a strong community feel, with many properties offering easy access to the town center and local amenities.

Lawrence Farms East: Prestigious Living

Lawrence Farms East is another highly sought-after enclave, characterized by its prestigious homes and well-established streetscapes. Properties here represent a blend of classic architecture and modern upgrades, appealing to buyers looking for elegance and a prime location.

The Chappaqua Lifestyle: More Than Just a Home

Living in Chappaqua extends beyond the four walls of your home; it's about embracing a superior quality of life.

Exceptional Education: Horace Greeley High School and Beyond

The Chappaqua Central School District consistently ranks among the top in New York State. This commitment to educational excellence is a primary driver for many families looking at homes for sale in Chappaqua, ensuring access to outstanding public schools from elementary through high school.

Outdoor Recreation and Green Spaces

Nature enthusiasts will appreciate Chappaqua's abundance of parks and green spaces. Gedney Park offers walking trails and recreational facilities, while the nearby Rockefeller State Park Preserve provides miles of picturesque trails for hiking, horseback riding, and enjoying the tranquility of nature. Finding a home for sale close to these amenities enhances the Chappaqua living experience.

Commuting from Chappaqua: Convenience to NYC

Chappaqua's strategic location in Westchester County provides convenient access to New York City. The Chappaqua Metro-North station offers frequent express service to Grand Central Terminal, making it an ideal location for commuters seeking a peaceful suburban retreat without sacrificing urban accessibility. Many homes for sale are attractive due to their proximity to the train station.

Navigating the Chappaqua Real Estate Market with Tierra Stanback

Identifying the perfect home among the many desirable homes for sale in Chappaqua, NY, requires local expertise. Tierra Stanback is dedicated to providing comprehensive guidance, helping buyers understand market nuances, explore off-market opportunities, and navigate the purchasing process with confidence. Whether you are searching for a starter home, a sprawling estate, or an investment property, Chappaqua offers diverse options waiting to be discovered.

Newest Homes for Sale in Chappaqua, NY

$1,849,000

1005784 MLS ⋅ 21 BLDG.

Investment opportunities like this rarely become available in Downtown Chappaqua. Welcome to 21 King Street, a rare mixed-use commercial property offering exceptional visibility, convenience, and income potential in one of Westchester's most desirable downtown locations. The building features two street-level retail storefronts and a residential apartment above, creating multiple income streams and long-term investment value. A standout feature is the private rear parking lot accommodating approximately 14 vehicles—an increasingly valuable asset in downtown Chappaqua. In addition to serving the property's tenants and customers, the parking area may offer additional income potential through rental opportunities. The rear lot also presents future upside, as it may provide opportunities for expansion or redevelopment, subject to municipal approvals and zoning requirements. Ideally positioned just moments from shops, restaurants, and the Metro-North train station, 21 King Street benefits from excellent foot traffic and a highly sought-after location. Whether you are an investor seeking diversified income streams, an owner-user looking to establish a presence in Chappaqua, or someone searching for a prime long-term asset, this is a unique opportunity to own a landmark property in the heart of town with both immediate cash flow and future potential.

21 King Street, Chappaqua

$785,000

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 David Graham-designed 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

$2,995,000

4 Beds ⋅ 6 Baths ⋅ 992104 MLS

Exceptional new construction opportunity in the highly sought-after Chappaqua School District, currently being built with anticipated completion this November 2026. Early buyers will have the rare chance to customize some of the final finishes and tailor the home to their personal style. This thoughtfully designed home offers 4 bedrooms and 5.1 bathrooms, with a highly desirable layout that lives like a larger home thanks to additional flexible living spaces. The main level features an open-concept design with seamless flow between the kitchen, dining area, and informal living room with fireplace. The kitchen is equipped with a premium Thermador appliance package and includes sliding glass doors leading to the back patio, while the family room also features sliders to the covered patio—creating a seamless connection and the perfect setting for indoor-outdoor entertaining. In addition to the formal dining room, formal living room, and powder room, the main level also includes a versatile room adjacent to a full bathroom, ideal for use as a private office, den, or guest accommodations. The fully finished walk-out lower level adds substantial additional living space, including an additional room with sliding glass doors and access to a full bathroom—well-suited for a variety of uses including extended living, recreation, or work-from-home needs. The primary suite is a true retreat, showcasing a tray ceiling, two oversized walk-in closets, and a luxurious bathroom with double vanity, soaking tub, separate shower, and private toilet room. A second-floor laundry room adds everyday convenience. Just a few additional highlights include 9-foot ceilings throughout, 4" oak hardwood floors, high-end finishes across all levels, an oversized two-car garage leading to a mudroom with custom cubbies and closet, a high-efficiency heat pump and cooling system, pre-wiring for a future electric vehicle charging station, and a security system. Privately set on over an acre of land on a cul-de-sac street and surrounded by mature trees, this home offers a peaceful setting while remaining close to parks, town, schools, and transportation. A rare opportunity to own a brand-new, thoughtfully designed home with exceptional flexibility in an ideal Chappaqua location.

39 Barnes Lane, Chappaqua

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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.