Explore Chappaqua, NY Homes for Sale Between $1,500,000 to $2,000,000
Chappaqua, NY Homes for Sale Between $1,500,000 to $2,000,000 Map Search

Homes for Sale in Chappaqua, NY Between $1,500,000 to $2,000,000

  Advanced Search   Market Reports   Home Value   Connect

Welcome to your dedicated resource for Homes for Sale Between $1,500,000 to $2,000,000 in Chappaqua, NY. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As a local Chappaqua, NY agent, Jeremy Zucker specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the properties currently available between $1,500,000 to $2,000,000 below, or contact a local agent to discuss the details that matters most to your search.

< Back to all Homes for Sale in Chappaqua, NY

Search Chappaqua, NY by Price

All Chappaqua, NY Homes for Sale Between $1,500,000 to $2,000,000

$1,550,000
3 Beds ⋅ 3 Baths ⋅ 1023910 MLS
1926 Colonial with timeless character on a private and level half-acre, walkable to the train station and village in Chappaqua, NY. Circular driveway and classic curb appeal set the tone; inside, hardwood floors flow through an open, light-filled layout. The kitchen opens to a fireplaced family room with deck access, plus a formal dining room and a living room with its own wood-burning fireplace and screened porch. Upstairs, lives as a four-bedroom layout, the primary suite is a true retreat - en-suite bath with sauna and private balcony overlooking the yard with Koi pond plus an office/den, and a full hall bath. The partially finished lower level adds a playroom, wine closet, and storage. Brand new central air conditioning, plus a gas line on the street, offers possible future conversion.

312 Quaker 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
$1,998,999
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
$1,849,000
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
$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
$1,665,000
931118 MLS
Extremely rare and ultra-private 12.92 acres of waterfront land in the Whippoorwill Lake enclave of Chappaqua. An exceptionally private canvas for a one-of-a-kind secluded getaway compound. Beyond the gate, a long private drive ascends to a concealed building site with sweeping lake and woodland vistas, plus natural water features including a waterfall and bridge. Near Whippoorwill Park, Chappaqua’s largest preserve (169 acres) and adjoining other protected woodlands. Minutes to Chappaqua, Armonk, and Mt. Kisco, express NYC commute and just 15 minutes to Westchester County Airport. Choice of Chappaqua or Armonk schools. The land sits within the Croton Watershed. An optional, stunning modern architectural package designed specifically for the site to maximize bucolic views. Full plan set and renderings available under separate agreement ($250,000). A truly one-of-a-kind and rare offering. Showings by appointment only for discerning, qualified buyers with verified proof of funds. Ideal for those seeking to build a custom private compound or a bespoke retreat.

767 King Street, 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.