Westchester Homes with Chappaqua School district

Westchester Homes with Chappaqua School district

Welcome to Westchester County, New York, a vibrant and picturesque region that beautifully blends suburban charm with urban convenience. Nestled just north of New York City, Westchester is renowned for its stunning landscapes, rich history, and thriving communities. With a diverse array of parks, cultural attractions, and dining options, residents enjoy a lifestyle that balances tranquility and excitement.

One of the standout features of Westchester County is its exceptional school districts, particularly the esteemed Chappaqua School District. Known for its commitment to academic excellence and holistic student development, Chappaqua offers a nurturing environment where children thrive. Families are drawn to this district for its dedicated educators, innovative programs, and a strong sense of community. The district's top-tier schools consistently rank among the best in the state, making it a prime choice for those seeking quality education for their children.

When it comes to real estate, Westchester County boasts a diverse selection of homes to suit every lifestyle. From charming historic properties to modern new builds, the housing market in this area is both dynamic and appealing. Many homes are nestled in picturesque neighborhoods, complete with tree-lined streets and easy access to parks and recreational facilities. Living in Westchester means enjoying the best of both worlds: serene suburban living with the bustling energy of New York City just a train ride away.

Explore the beauty and opportunities that Westchester County has to offer, and discover why so many families choose to call this enchanting region home. Whether you’re looking for a cozy family home or a luxurious estate, Westchester is ready to welcome you!

Newest Westchester Homes with Chappaqua School district

$1,399,000
3 Beds ⋅ 3 Baths ⋅ 1046960 MLS
SoHo in Chappaqua! Chappaqua schools! Dramatic, Airy and Light-filled 3 Bedroom Contemporary in immaculate condition located in sought-after neighborhood and Cul-De-Sac. Set on almost an acre of private property with rocking-chair front porch. Elegant living room features a soaring cathedral ceiling, wall of built-in bookshelves and wall of windows opening to dining area with access to deck. Renovated eat-in-kitchen offers granite countertop, pantry closet, stainless steel appliances and breakfast area with access to deck. Large family room with wood stove and custom mantle. Den/Office/Study with closet and renovated new bath completes the first floor. Primary bedroom with walk-in-closet, an additional closet and freshly renovated in-suite full bathroom. Two addditional bedrooms with renovated Jack-and Jill bath. Full semi finished lower level with Library and Recreational/Gym room 281sqft with CO (included in total). This exceptional home with wall of windows, skylights, high/cathedral ceilings, open floor plan, two decks, Living Room, Family Room with Fireplace, Office/Den, Eat-In-Kitchen, hardwood floor with views of lush park property is ideal for indoor and outdoor entertaining. A must see!

10 Deborah Lane, Chappaqua
$749,000
3 Beds ⋅ 2 Baths ⋅ 1043982 MLS
You’ll be hard-pressed to find a turn-key home like this—especially at this price—in the Chappaqua School District, let alone Westchester County! Welcome to this charming 1850s Colonial, ideally situated in the heart of Chappaqua, just 0.3 miles on foot via a convenient sidewalk to Metro-North and close to all that the village has to offer. With an easy walk to the train and convenient access by car, commuting to NYC couldn’t be easier. Filled with natural light and lovingly maintained, this inviting home beautifully blends timeless character with thoughtful updates. The updated kitchen features stainless steel appliances, quartz countertops, and a convenient side entrance. Gather around the fireplace in the cozy living room, or unwind in the quiet sitting room after enjoying a meal in the formal dining room. Beautiful hardwood floors and original millwork add warmth and charm throughout. Upstairs, you’ll find three lovely bedrooms, including one with its own convenient powder room. The walk-up attic and walkout basement offer ample storage and additional flexibility. The home has been thoughtfully updated with young mechanicals, including a 2020 furnace, 2023 hot water heater, 2023 electrical panel, and a 2022 three-bedroom septic system. A rare opportunity to own a move-in-ready Colonial in one of Westchester’s most desirable communities and school districts—close to shops, restaurants, parks, schools, and just a short 0.3-mile walk to Metro-North for an easy NYC Commute.

27 Mill River Road, Chappaqua
$1,575,000
4 Beds ⋅ 3 Baths ⋅ 1047882 MLS
Welcome home to Chappaqua's best kept secret right in town! This classic 1989 center hall colonial has been reimagined for the way we live today, blending sun drenched, open spaces with effortless modern style, all less than a mile to the charming village, convenient train and public library. Step inside to a first floor that flows beautifully from room to room. The open concept living and dining rooms and kitchen bask in natural light all day long, anchored by a striking fireplace that begs for cozy evenings in. Need a smaller spot to unwind? The family room off the kitchen is the perfect retreat for movie nights and quiet mornings. The chef's kitchen is where this home truly shines, with a generous island for gathering and doors that open onto a sprawling deck. From there, steps lead down to a private yard, made for summer barbecues, morning coffee, and everything in between. Indoor outdoor living has never felt so seamless. A well appointed laundry room and stylish half bath round out this level. Upstairs, four bedrooms offer a peaceful escape, headlined by a primary suite with a generous walk in closet and a spa like bath that feels like your own private retreat. The lower level delivers exceptional storage with convenient walk out access, and a two car garage with EV charging plus ample driveway space means there is room for everyone. This home has been loved and is ready for the next owner to enjoy it. Welcome home.

9 Lori Lane, Chappaqua
$1,725,000
4 Beds ⋅ 4 Baths ⋅ 974007 MLS
Welcome to an exceptional move-in ready home located in a highly desirable Chappaqua neighborhood known for its award-winning schools & sought-after lifestyle. Perfectly positioned in a quiet neighborhood, this stunning property offers privacy, space & luxury living at its finest. In addition, easy access to the North County Trail for any outdoor activities of your choice. Step inside & you'll find a bright, open-concept floor plan with natural light & high-end finishes throughout. The eat-in gourmet stylish kitchen is a chef's dream, complete with stainless steel appliances, state-of-the-art cabinetry & a large center island - perfect for entertaining or everyday living. The inviting living room & elegant dining space provide a seamless flow, ideal for gatherings of any size. The upstairs boast 4 spacious bedroom plus an office and bonus space ideal for kids suite or study. The luxurious primary suite includes spa-inspired bathroom, oversized shower, & a generous walk-in closet. Outside, step into your own private oasis designed for ultimate outdoor living with a spacious patio, a 3-season screened in porch & flat backyard. Whether you're a first time home buyer or upgrading, this is a rare opportunity to own a turn-key home in one of Westchester's finest communities. Come visit today!

53 W Orchard Road, Chappaqua
$1,800,000
4 Beds ⋅ 4 Baths ⋅ 1044050 MLS
Welcome to this beautifully maintained almost 3000 sq ft 4 bedroom 4 bath Colonial set on a private, sun-filled one acre property framed by mature trees, a classic stone wall , and meticulously maintained landscaping and plantings. Elegance and craftsmanship are evident throughout with beautiful hardwood floors, generously sized bedrooms and a primary suite with private en-suite bath. At the heart of the home, the kitchen opens to an inviting sitting room with a gorgeous stone fireplace and double doors leading to a seamless indoor-outdoor living experience. The finished walkout lower level offers exceptional additional living and entertaining space, complete with a bathroom and built-in ceiling speakers (with surround sound), plus direct access to the grounds and pool area. Outside, enjoy your own private retreat featuring a 40' X 16' heated in-ground fiberglass pool with sunning deck and full Certificate of Occupancy along with a new patio and fire pit under the deck. The pool is professional maintained weekly, and the propane tanks for the pool heater were recently filled. Additional improvements include a freshly painted exterior and deck (August 2026), new hot water heater and refrigerator (2024), septic cleaning (June 2026)and an EV charging port in the two-car garage. There is an alarm system in place. Thoughtfully maintained and move-in ready, this home combines timeless craftsmanship, modern conveniences, and resort-style indoor-outdoor living in a beautiful and private setting.

406 Bedford Road, Chappaqua
$2,400,000
4 Beds ⋅ 4 Baths ⋅ 1042846 MLS
- ELEVATED LIVING, LIGHT-FILLED DESIGN - This home has been transformed through a combination of new construction and thoughtful remodeling, blending classic Colonial proportions with a fresh, light-filled interior built for gracious living and effortless entertaining. The rebuild includes all-new HVAC, plumbing, and electrical systems and a full-house 25kW Generac generator. This lovely residence features 4 well-proportioned bedrooms and 4 bathrooms (3 full, 1 half) thoughtfully arranged across 3 finished levels, including a full lower-level recreation room. The 1st floor and 2nd floor consist of 3,191sq ft of livable space and the finished lower level is another 649 sq ft which gives you 3,840 total livable space to suit your family’s needs. At the heart of the home is a sprawling, sun-drenched great room where kitchen, dining, and family room flow together beneath soaring vaulted ceilings, a true showpiece for entertaining on any scale. The chef's kitchen commands the space with a grand quartzite island large enough to gather a crowd around, a full Thermador appliance suite, and custom Bilotta designed cabinetry, all opening onto a stone fireplace lounge or out to the rear deck for seamless indoor-outdoor living. A series of solar-powered skylights washes the main and second floors in natural light, lending the home an elevated, airy quality, a kind of California-meets-East-Coast serenity rarely found north of the city. For quieter moments, a separate formal living room with French doors offers refined, intimate gathering space, while an attached two-car garage adds everyday convenience. Upstairs, the primary suite delivers a true retreat, with a private sitting area, an oversized walk-in closet, and a spa-caliber bath with a freestanding soaking tub and oversized large glass shower. Three additional bedrooms and a second-floor laundry room complete the level with equal care. Set on an acre of flat, landscaped grounds, the property offers privacy, space, and room to entertain outdoors with space reserved for your growing needs. Architectural details include a considered blend of modern and traditional materials creating exceptional curb appeal and lasting quality. The coveted Millwood location offers the best of community living, with proximity to local shops and restaurants, the Taconic State Parkway, and Chappaqua schools, Westorchard Elementary, Seven Bridges Middle, and Horace Greeley High. At last, your perfect home awaits, where classic architecture meets modern open-plan living in beautiful Millwood. Note: The neighborhood section on Zillow is showing the incorrect neighborhood, house is located at 230 Pinesbridge Road.

230 Pinesbridge Road, Millwood
$1,359,000
3 Beds ⋅ 3 Baths ⋅ 1041830 MLS
Welcome to this spacious and private Millwood home, ideally located in the award-winning Chappaqua School District. This 3-bedroom, 2.5-bath home lives like a 4-bedroom (currently used as a dedicated home office/den). A charming woodland driveway leads to a light-filled home featuring hardwood floors, oversized windows, and beautiful decorative mouldings. The main level offers an eat-in kitchen with a bright breakfast nook, formal dining room, living room, large sunken entertaining room with a fireplace, powder room, and easy access to the private grounds. The outdoor deck, surrounded by lush woodland, natural rock formations, and mature landscaping, is perfect for relaxing and entertaining. Upstairs are three spacious bedrooms, a flexible home office/den, and two full baths. The primary suite features a separate sink and vanity area. A two-car garage adds convenience. Enjoy the best of the Chappaqua and Millwood lifestyle, with nearby hiking trails, Gedney Park, local shops and restaurants, and convenient access to Metro-North and Taconic Parkway for an easy NYC commute. A peaceful private retreat with the convenience of being close to it all.

180 Somerstown Road, Millwood
$70,000
1034505 MLS
A Rare Land Opportunity in Millwood Bring your vision to this approximately 0.55-acre parcel in the coveted Chappaqua Central School District. Ideally located in the heart of Millwood, this property offers the opportunity to create something of your own in a highly desirable Westchester community. The parcel is being offered as an undeveloped building lot and requires zoning, planning, and Board of Health approvals. Soil type is currently unknown. Buyers should conduct their own due diligence regarding zoning, building potential, septic requirements, setbacks, and all necessary municipal approvals. Adding exceptional appeal to this property are exclusive rights to the private Hidden Hollow Lake Community. A rare amenity, these rights provide access to a private sandy beach where residents can swim, kayak, and canoe. Imagine building a home where weekends can feel like a getaway, with lake recreation just moments from your door. The location offers the best of both worlds, the convenience of Millwood and the beauty of a nature-oriented setting. The property is just minutes from Millwood Shopping Plaza, featuring DeCicco's Gourmet Market, Tazza Cafe, Drug Mart, and the Millwood Post Office. The Taconic State Parkway is easily accessible, while the nearby North County Trailway provides miles of opportunities for walking, running, and biking. Located within the highly regarded Chappaqua Central School District, this is an exciting opportunity for builders, investors, or buyers looking to create a custom home in a sought-after location with a truly special recreational amenity. Rare land. Coveted schools. Hidden Hollow Lake rights. Millwood convenience. Bring your plans and explore the possibilities.

1 Pamela Place, Millwood
$679,000
4 Beds ⋅ 2 Baths ⋅ 1034483 MLS
A Rare Opportunity in the Heart of Millwood. Lake life, privacy, Chappaqua schools, and the convenience of being minutes from the heart of Millwood. This unique property offers an exceptional opportunity to create your own retreat in one of Westchester's most desirable communities. Set back from the road on 0.55 acres of beautiful grounds, this four-bedroom Raised Ranch enjoys a wonderful sense of privacy and connection to nature, while being just minutes from Millwood's shops, restaurants, and everyday conveniences. Mature landscaping and wooded surroundings create a natural buffer from the road and a setting that feels surprisingly removed from the activity of the area. And then there is Hidden Hollow Lake one of the property's most exceptional features. The home enjoys exclusive rights to the private Hidden Hollow Lake Community at no additional charge, a rare benefit enjoyed by very few properties. Residents have access to a private sandy beach where they can swim, kayak, and canoe, creating a true vacation-like lifestyle just steps from home. Built in 1954 and offering approximately 1,200 square feet, the four-bedroom, 2 bath home is being offered strictly as-is and presents an exciting opportunity for buyers looking to renovate, expand, or create a home uniquely suited to their needs. The main level features a welcoming living room with an open red-brick fireplace and wood-burning stove, with sliding doors opening to a charming three-season sunroom overlooking the backyard. The kitchen and dining area, powder room, laundry room, and access to the one-car garage complete this level. Upstairs are four bedrooms and a full bathroom. The primary bedroom offers access to a large covered sunroom and a beautiful wooden deck overlooking the grounds, providing a wonderful place to enjoy the natural setting and envision future possibilities. Outside, mature landscaping, flowering trees, specimen plantings, and wooded surroundings create a beautiful natural backdrop. A walking trail from the property leads toward Hidden Hollow Lake, making it easy to enjoy the lake and its recreational amenities right from home. The location is equally appealing. The property is just minutes from Millwood Shopping Plaza, home to DeCicco's Gourmet Market, Tazza Cafe, Drug Mart, and the Millwood Post Office. The Taconic State Parkway is easily accessible, as is Gedney Park and the North County Trailway, offering miles of opportunities for walking, running, and biking. Located in the highly regarded Chappaqua Central School District, the property combines the convenience of a central Millwood location with the beauty of mature grounds, lake access, and abundant outdoor recreation. Additional Land Available For those seeking even more space, there is an opportunity to purchase the adjoining approximately 0.55-acre residentially zoned lot. Subject to all applicable municipal approvals, the additional parcel could potentially accommodate a separate residence, or it could simply be acquired to create a larger private property with additional land, flexibility, and privacy. A rare Millwood opportunity with deeded Hidden Hollow Lake rights, Chappaqua schools, beautiful grounds, and room to create something truly your own. A property with possibilities and a lifestyle that is increasingly difficult to find.

457 Saw Mill River Road, Millwood
$1,665,000
1038452 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
$2,137,500
4 Beds ⋅ 6 Baths ⋅ 1025674 MLS
A rare opportunity to create a forever home on nearly 7 private acres in the Chappaqua School District. Rich in history, character and natural beauty, 82 Shingle House Road is a distinctive Millwood estate for the buyer who values land, privacy and potential over cookie-cutter perfection. Originally dating to 1762, the property has evolved over time and offers a unique combination of old-world charm, generous space and exceptional flexibility. The main residence features spacious living areas, a large chef’s kitchen, fireplaces, beautiful natural light and peaceful views of the grounds. While the home offers great bones and many modern day appealing features, it is ready for the next owner to bring vision, updates and restoration to make it truly their own. Set on approximately 6.97 acres, the grounds are what make this offering so special: a private pond, mature trees, landscaped stonework, concrete pool, hot tub, cabana, open lawns, wooded surroundings and an extraordinary sense of seclusion. Additional improvements include a detached guest cottage situated above a three-car garage, plus a second three-car garage with a private pine-paneled retreat and a private meditation space with a stone fireplace, offering endless possibilities for guests, extended family, office, creative or recreational use. This is a property for someone who wants more than a house. It is for the buyer who wants a setting, a lifestyle and the chance to restore and personalize a truly special estate in one of Westchester’s most sought-after school districts. Rare, private and impossible to duplicate, 82 Shingle House Road is ready for its next chapter.

82 Shingle House Road, Millwood
$1,590,000
3 Beds ⋅ 4 Baths ⋅ 1017997 MLS
Tastefully Expanded and Renovated Colonial in the Heart of Chappaqua - New 4 bedroom Septic, 2024 Roof and Exceptional Indoor/Outdoor Living. Just moments to Chappaqua village, Metro North and highly regarded Chappaqua schools. A flexible first-floor guest/au pair suite with private bath, chefs kitchen with Wolf appliances, private primary suite, 2 fireplaces, expansive deck and mature grounds backing to protected green space. A welcoming foyer opens to a gracious living room and fireplace. A formal dining room with a tray ceiling. Timeless appointed chefs eat-in-kitchen with Wolf appliances, custom cabinetry and marble counter tops, wine refrigerator and breakfast bar. The family room offers a second fireplace, a coffered ceiling, 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 au pair/guest room and full bath. Upstairs is the primary bedroom with high ceilings, walk-in custom closet, private study with built-ins, and en-suite bath with double sinks, marble shower and whirlpool tub. 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.

131 Douglas Road, 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.