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

$2,299,000

5 Beds ⋅ 5 Baths ⋅ 1036792 MLS

Welcome to 20 Hitching Post Lane in Chappaqua, New York. This five-bedroom, 4.1 bath Colonial is set on over 2 bucolic acres on a beautiful tree-lined street. An impressive oak floored entry foyer with cherry inlay opens to a spacious formal living room with crown moldings and new windows (2023), warmed by a wood burning fireplace with decorative mantle. The adjacent family room has a second wood burning fireplace, this one brick, spanning floor-to-ceiling with raised hearth. Sliding glass doors lead from the Family Room to an Azek deck installed in 2016. Walk through the formal dining room accented with chair rail and crown molding, into a chef's kitchen with Richmaid cabinetry and tumbled marble backsplash with hand painted accents, a center island, and GE Monogram 6 burner gas stove with convection oven, farm sink, GE Monogram side/side refrigerator, microwave and dishwasher. Sliding glass doors open from the kitchen to deck with internal shades. The second floor Primary bedroom has a private bath with steam shower, double vanity and a Crema Marfil counter, whirlpool tub and radiant heated stone floors. The walk out lower level is included in the square footage and has a laundry room, playroom and a full bath. The mechanicals include: 4 zone heat, 3 zone AC, sophisticated sound system and CAT 5 wiring, full house generator (2014) Azek deck with an automated awning, fenced in yard, above ground oil tank (2024) and irrigation system. Enjoy this professionally landscaped retreat, minutes from downtown with easy Metro-North railroad service to New York City.

20 Hitching Post Lane, Chappaqua

$679,000

4 Beds ⋅ 2 Baths ⋅ 1046287 MLS

A unique opportunity to create your dream home on 3+ wooded acres in the highly sought-after Chappaqua School District. Tucked away at the end of a cul-de-sac, this exceptional property offers privacy, natural beauty, and tremendous potential for a builder, investor or end user. The existing home is in need of removal, presenting an opportunity to bring your vision to life and build a new custom residence on this beautiful parcel. The expansive wooded setting provides a wonderful sense of seclusion while being conveniently located near Chappaqua shops, schools, restaurants and train station. A rare chance to build in an established highly desirable neighborhood surrounded by gracious homes and natural landscape. Bring your architect and builder and explore the possibilities.

10 Paula Place, Chappaqua

$5,750,000

6 Beds ⋅ 8 Baths ⋅ 1017994 MLS

Welcome to 24 Trails End, an unparalleled private resort estate redefining luxury living on over 9 pristine, park-like acres. This majestic brick Colonial, quietly positioned at the end of a prestigious cul-de-sac, overlooks its scenic, spring-fed pond. Inside, classic architectural sophistication meets modern design, highlighted by a soaring double-height great room, dual home offices, and a rich mahogany billiard room with a wet bar and fireplace. The heart of the home is an expansive chef's kitchen, with an oversized marble island, and a sunny breakfast area. The lower level is an extraordinary recreation destination, boasting a 2600 sqft indoor sports court lined for basketball and pickleball, alongside a full home gym. Step outside to your private backyard paradise with an inviting heated Gunite pool, integrated spa, and a pool house/cabana surrounded by sprawling bluestone terraces and meandering walking trails. Two firepits located around the property and a serene pond with an island, an additional firepit and two docks for unmotorized boat usage complete this spectacular picture. An ultra-private lifestyle compound in the award winning Chappaqua schools, just under an hour from Manhattan.

24 Trails End, Chappaqua

$1,299,000

4 Beds ⋅ 3 Baths ⋅ 1029575 MLS

Welcome home to a meticulously maintained center hall colonial home set on two plus sensational & picture perfect flat acres at the end of a quiet cul de sac street in the Chappaqua school district. Located in a highly desirable neighborhood, this four bedroom home offers comfortable living spaces and the timeless qualities that make it an ideal place to call home for years to come. The expansive backyard boasts a wood deck that was re built a decade ago and overlooks a piece of property that is simply perfect for recreation, gatherings, and play. A classic center hall layout anchors the home with a gracious entry foyer and a light filled living room with oversized windows on opposite ends on one side of the home and a formal dining room with crown molding on the other side. The kitchen is outfitted with a new cooktop, backsplash, sink & granite countertops and has outdoor access. Adjacent to the kitchen up a few steps is a flexible bonus room with a wood burning fireplace and recessed lighting that adds additional living space with endless possibilities to suit today’s lifestyle. A powder room & convenient main level laundry room complete the first floor. Upstairs, a generous primary suite features an updated bath (2021) and two walk in closets. The upper level also boasts three spacious bedrooms (all with hardwood flooring below carpet), and a full hall bathroom (also renovated in 2021). The unfinished walk out lower level (approx 990 q feet not included in total) provides a blank canvas for future expansion and can be finished to create additional space for entertaining, recreation and fitness. Major improvements to the home that will provide peace of mind include - roof/siding/re paved driveway/garage doors and above ground oil tank (2014), hot water heater (2018), furnace (2019), gutters (2024). Additional highlights include new interior wood doors, crown molding, central air, a portable generator hook up, and Marvin windows. A quality built home situated in a neighborhood ideal for biking/walking/play and a piece of property to be envied - a combination not to be missed!

55 Brandon Drive, Mount Kisco

$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

$2,200,000

4 Beds ⋅ 4 Baths ⋅ 1042846 MLS

Note: The neighborhood section on Zillow is showing the incorrect neighborhood, house is located at 230 Pinesbridge Road. - 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.

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

Start Your Search

© 2026 TReND. All Rights Reserved.
The data relating to real estate for sale on this website appears in part through the TReND Internet Data Exchange (IDX) program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Real Broker NY LLC participates, and is provided by TReND through a licensing agreement. Real estate listings held by brokerage firms other than Real Broker NY LLC are marked with the IDX icon and detailed information about each listing includes the name of the listing broker.
All information provided is deemed reliable but is not guaranteed. Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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.