Westchester Homes with Chappaqua School district

Welcome to Westchester County, New York—an idyllic blend of suburban charm and urban convenience, making it one of the most sought-after places to call home in the United States. Nestled just north of New York City, Westchester boasts picturesque landscapes, vibrant communities, and an abundance of recreational opportunities. Whether you're exploring the scenic trails of the Hudson River Valley or indulging in the rich cultural offerings of towns like White Plains and Yonkers, Westchester has something for everyone.

One of the standout features of this county is the esteemed Chappaqua School District, renowned for its commitment to academic excellence and holistic student development. Families flock to this area for its top-ranking public schools, which offer a nurturing environment and a wide array of extracurricular activities. The district's dedication to fostering creativity and critical thinking ensures that children are well-prepared for future success.

As you explore the real estate options within the Chappaqua School District, you'll find a diverse selection of homes that cater to various lifestyles and preferences. From charming historic houses with character to modern, spacious family homes, the properties here are as unique as the families that inhabit them. The close-knit community ambiance, coupled with outstanding educational opportunities, creates an inviting atmosphere for families looking for their forever home.

Westchester County is not just a place to live; it's a place to thrive. With its beautiful neighborhoods, excellent schools, and easy access to the bustling energy of New York City, it’s no wonder that so many choose to call Westchester home. Discover your dream home in this remarkable region today!

Newest Westchester Homes with Chappaqua School district

$1,188,000

4 Beds ⋅ 3 Baths ⋅ 1026394 MLS

Smartly updated, multi-level home offers room for everyone. Living room with wood-burning fireplace. Transom windows frame the entries to the thoughtfully designed eat-in kitchen with wood cabinetry, Miele induction cooktop and in-wall convection oven, Bosch refrigerator/freezer and dishwasher, GE microwave and granite counter tops, which adjoins the family room with slider to the deck on one side and the formal dining room with French doors to deck for dining alfresco on the other. Private home office. Spacious bedrooms with recessed lighting and hardwood flooring, including primary bedroom with walk-in closet. Jack-n-Jill bath with shower over bathtub. Hall bath with shower over jetted tub. Large walkout lower-level recreation room with slider to deck. Sitting/media room. Laundry/mud room outfitted with Samsung washer and dryer, slop sink, closet and side entry adjoins attached, 2-car garage with Tesla charger. Mostly new windows. Septic system upgraded 2022. New Fujitsu mini split AC system (10 indoor units and 3 outdoor units) 2023. Hybrid electric water heater 2024. Upgraded 400 AMP electrical service 2025. New Stiebel Eltron wall-mounted electric heaters (4) 2025. New roof and new leased 12.6kW Tesla PV solar system with battery backup 2026. Privately nestled in Lawrence Farms East, a highly sought-after enclave in the Town of New Castle featuring Chappaqua schools and easily commutable from Chappaqua or Mount Kisco via Metro-North and/or the Saw Mill River Parkway.

11 Kitchel Road, Mount Kisco

$1,150,000

4 Beds ⋅ 3 Baths ⋅ 1024331 MLS

***CHAPPAQUA SCHOOL DISTRICT*** Tucked away on a quiet cul-de-sac and set on nearly half an acre of beautifully landscaped property, this sun-filled Colonial offers the perfect combination of space, comfort, and convenience. Thoughtfully maintained and move-in ready, the home features almost 3,000 square feet of inviting living space for everyday living and effortless entertaining. A welcoming foyer leads to the spacious eat-in kitchen appointed with granite countertops, stainless steel appliances, and generous prep space with an adjoining dining room ideal for hosting gatherings. The fully enclosed family room anchored by a wood-burning fireplace and framed by oversized windows can be used as a bright, spacious office or a fifth room. A versatile office/mudroom, powder room, and access to the attached two-car garage complete this level. Just a few steps up, the expansive living room offers a bright, airy retreat with hardwood floors and large windows overlooking the surrounding property—creating the perfect space to relax or entertain. A few more steps lead to the private bedroom level, where the spacious primary suite features an en-suite bath and generous closet space. Three additional well-proportioned bedrooms share a full hall bath, offering comfortable accommodations for guests or flexible work-from-home needs. The finished walk-out lower level provides exceptional bonus space ideal for a recreation room, playroom, fitness area, or media room, along with laundry and abundant storage. Outside, a spacious recently refinished deck overlooks the private, tree-lined backyard, creating a peaceful setting for outdoor dining, entertaining, or simply enjoying the tranquil surroundings. Ideally located 7 minutes from downtown Mount Kisco and the Metro North station and 5 minutes from Chappaqua Crossing, Whole Foods, and Lifetime Fitness. You’ll enjoy easy access to acclaimed restaurants, shopping, parks, all within the highly regarded Chappaqua School District. Offering an ideal blend of space, location, and lifestyle, this is a home you’ll enjoy for years to come.

49 E Ridge Lane, Mount Kisco

$2,250,000

4 Beds ⋅ 6 Baths ⋅ 1025674 MLS

82 Shingle House Road, Millwood A colonial-era Millwood estate, thoughtfully evolved for modern living. Originally dating to 1762, 82 Shingle House Road offers a rare opportunity to own a distinctive private estate set on approximately 6.9 acres within the Chappaqua School District. Located along one of Millwood’s historic roads, the property combines centuries-old character with exceptional space, privacy and resort-style amenities. The main residence offers four bedrooms, three-and-a-half baths and generous living spaces designed to take full advantage of the property’s peaceful natural surroundings. An inviting eat-in country kitchen features character-rich wood plank floors, while the living room overlooks the pond and waterfall. Additional highlights include multiple fireplaces, radiant heat in the primary bathroom and extensive closet and storage space. Beyond the main residence, the property includes a renovated guest cottage situated above a three-car garage, providing flexible accommodations for guests, extended family, a home office or studio. A second three-car garage includes a private pine-paneled retreat or meditation room with a dramatic stone fireplace. The grounds create a setting that is increasingly difficult to find. A heated in-ground concrete pool, private pond, waterfall, landscaped gardens, mature specimen plantings and a three-hole golf course are all surrounded by nearly seven acres of privacy. More than simply an older home, 82 Shingle House Road is a property shaped over generations - offering history, character and a sense of place that cannot be replicated by new construction. A rare opportunity to become the next steward of one of Millwood’s most distinctive private estates.

82 Shingle House Road, Millwood

$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

$1,995,000

4 Beds ⋅ 3 Baths ⋅ 882412 MLS

Nestled on a picturesque tree-lined street in the highly sought-after Chappaqua School District, this beautifully renovated 4-bedroom Colonial combines timeless charm with thoughtfully updated living spaces. A welcoming front porch offers the perfect place to enjoy a quiet morning coffee or relax on a summer evening. A gracious entry foyer introduces the home's warm and inviting interior. The sun-filled living room features oversized windows, custom built-ins, and elegant proportions, creating a comfortable space for everyday living and entertaining. At the heart of the home is the beautifully renovated chef's kitchen with top of the line stainless appliances, designed for both function and style, with a spacious center island with seating, a sunny dining area, built-in desk, generous walk-in pantry, and access to the deck for seamless indoor-outdoor living. Just beyond the kitchen, the inviting family room is anchored by a raised-hearth wood-burning fireplace, offering a warm and comfortable gathering space. The first floor also includes a formal dining room and a versatile room with walls of windows, ideal as a second family room, home office, playroom, or sunroom, a full bath and laundry room. Upstairs, the primary suite has a renovated bath and large walk-in closets. Three additional bedrooms share a well-appointed hall bath, providing ample space for family and guests. The expansive lower level offers exceptional storage and outstanding potential for future finished recreation, fitness, or media space. Throughout the home, rich hardwood floors, custom millwork, abundant natural light, and a thoughtfully designed open floor plan create an atmosphere that is both elegant and welcoming. Ideally located in one of Chappaqua's most desirable neighborhoods, this is a home that offers timeless appeal, exceptional comfort, and a setting you'll enjoy for years to come. A must see home!!

12 Brandon Drive, Mount Kisco

$1,099,000

2 Beds ⋅ 3 Baths ⋅ 1004449 MLS

Welcome to this beautifully situated townhouse in the highly desirable Riverwoods community, where tranquil woodland views and thoughtfully designed living spaces create the perfect retreat. Nestled against a picturesque backdrop of mature trees and a gently flowing stream, this home offers both privacy and natural beauty in an exceptional setting. The sun-filled eat-in kitchen is as inviting as it is functional, featuring granite countertops, a gas stove, abundant cabinetry, and plenty of space for casual dining. Just beyond, the elegant formal dining room is framed by stunning triple floor-to-ceiling windows that bring the outdoors in and fill the space with natural light. The gracious living room is equally impressive, highlighted by detailed dentil moldings, a classic wood-burning fireplace with a handsome wood mantel, and sliding doors that open to a spacious deck overlooking the serene wooded landscape—an ideal spot for morning coffee, outdoor dining, or simply unwinding in nature. As you ascend to the second floor, a sunlit hallway lined with three oversized windows creates a bright and airy ambiance throughout the home. The expansive primary suite is a true sanctuary, featuring soaring cathedral ceilings, a generous walk-in closet, and a charming Juliet balcony with peaceful views of the private woods below. The luxurious primary bath offers a double vanity, a relaxing soaking tub, and a separate stall shower for a spa-like experience. A second spacious bedroom with its own ensuite bath provides comfort and privacy for family or guests, while the conveniently located laundry area on the upper landing adds everyday ease. The walk-out lower level offers exceptional flexibility, with a large family room perfect for gatherings, movie nights, or recreation. An additional versatile room can easily serve as a home office, gym, or guest space, complemented by a convenient half bath. A dedicated storage room and utility area complete this well-designed lower level. Combining elegant architectural details, generous living spaces, and a spectacular natural setting, this exceptional Riverwoods home offers comfort, charm, and a lifestyle of relaxed sophistication.

4 Annes Wood Lane, Mount Kisco

$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

$3,100,000

5 Beds ⋅ 6 Baths ⋅ 990281 MLS

Privately gated and masterfully crafted, this exceptional custom brick estate is a showcase of timeless elegance and grand-scale living, nestled on over two acres in the heart of Chappaqua. Beyond the cobblestone apron and curbing, a sweeping driveway leads to a residence designed for both luxury and comfort, boasting soaring 10-foot ceilings, four stately fireplaces, exquisite architectural detail, and refined finishes throughout. Enter through a breathtaking grand foyer, where gleaming hardwood floors with intricate wood inlay medallion set the tone, and a dramatic three-story suspended spiral staircase anchors the home in architectural splendor. The main level is ideal for entertaining, offering a formal living room, formal dining room, an expansive family room with a custom bar, and seamless access to a private bluestone patio, perfect for indoor-outdoor gatherings. The chef’s kitchen is a culinary masterpiece, featuring high-end appliances, breakfast area, butler’s pantry, and dual access points to the patio. A main-floor guest/au pair suite, private office or den, and powder room complete the level. Upstairs, the serene Master Suite is a retreat unto itself, complete with a sitting area, dual walk-in closets, and a spa-like marble bath with heated towel racks, dual vanities, clawfoot soaking tub, and an oversized glass shower. Three additional generously-sized bedrooms, one with an ensuite, and a full hall bath, along with a dedicated laundry room, offer both comfort and convenience. The third floor adds a spacious game and media room, while the walk-out lower level features a gym, mudroom, recreation space, sitting area, and access to the beautifully landscaped backyard. Outside, enjoy artisan stonework, multiple patios, a gazebo, hot tub, built-in BBQ station, and lush, level grounds ideal for entertaining and play. Three heated garages, including an electric vehicle charging station, complete this extraordinary masterpiece with modern convenience and sophistication. Located just minutes from Chappaqua’s charming village center, award-winning schools, fine dining, shopping, Mt. Kisco Country Club, Metro North, and major highways. This is a a rare opportunity to own one of Chappaqua’s most distinguished estates, an architectural triumph of timeless sophistication and commanding presence, set within one of Westchester’s most coveted communities.

2 Heathcote Drive, Mount Kisco

$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

$879,000

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

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