Chappaqua Homes with Garage Parking features

Welcome to the picturesque town of Chappaqua, nestled in the heart of Westchester County, New York. Renowned for its exceptional school district, Chappaqua Central School District consistently ranks among the top in the state, making it a sought-after location for families. With a strong emphasis on academic excellence, innovative programs, and a supportive community, students here thrive in an environment that fosters both intellectual and personal growth. The schools are equipped with state-of-the-art facilities and offer a rich array of extracurricular activities, ensuring that every child can explore their passions and develop their talents.

Beyond its educational offerings, Chappaqua is a charming town that blends suburban tranquility with vibrant community life. The local parks, quaint shops, and delightful eateries create a warm atmosphere where neighbors become friends. Whether you’re enjoying a weekend at the farmer's market or taking a leisurely stroll through the scenic trails, Chappaqua's community spirit is palpable.

For those considering a move to this idyllic town, you’ll find a variety of homes that cater to modern living, many of which boast garage parking features. Imagine the convenience of having a dedicated space for your vehicle, especially during the snowy winter months. These homes not only provide practical amenities but also offer the perfect backdrop for family gatherings and entertaining friends.

With its top-tier schools, welcoming community, and beautiful homes with garage parking, Chappaqua is more than just a place to live—it's a place to thrive. Discover your dream home in this enchanting town, where every day feels like a breath of fresh air.

Newest Chappaqua Homes with Garage Parking features

$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

$1,725,000

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

$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

$995,000

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

$999,000

3 Beds ⋅ 3 Baths ⋅ 997307 MLS

Private access to the scenic North County Trailway, offering miles of paved trails for walking, running, and biking, is just one of the many highlights of this beautifully maintained home. Not to be missed, this sun-filled 3-bedroom, 3-bath raised ranch offers a comfortable layout ideal for both everyday living and entertaining. Set privately on over 1.3 level acres and screened from the road by a row of mature trees, the property provides exceptional privacy and a peaceful setting. Enjoy summers by the in-ground pool, a spacious backyard perfect for play and gatherings, and the convenience of a 2-car garage. Ideally located in the heart of Millwood, close to shopping, restaurants, and major parkways and in Chappaqua Schools, this home offers the perfect balance of privacy, recreation, and convenience. New AC!

568 Saw Mill River Road, Millwood

$949,000

3 Beds ⋅ 2 Baths ⋅ 1004970 MLS

Best value in the Award Winning Chappaqua School District! Set on an acre in the desirable Rolling Fields neighborhood, this well maintained home offers comfortable living with a flexible layout that lives larger than its 3-bedroom configuration. Updated in 2013 with, new roof, new windows, new mechanicals, kitchen and bath renovations. The main level features an inviting kitchen with stainless steel appliances and granite countertops, open to the dining area for easy everyday living and entertaining. Hardwood floors run throughout the main floor of the home, and the spacious living room has a wood-burning fireplace. The primary bedroom includes an en-suite bath, while the layout offers the convenience of no stairs from the front entry to the main living areas and bedrooms. Additional space in both the lower level and attic provides exceptional flexibility for future expansion. The home also includes both a detached two-car garage and an attached one-car garage for a total of three garage spaces. Enjoy a wonderful combination of location, functionality, and future potential, ideally situated close to Chappaqua and Mount Kisco town centers, Metro-North train service to NYC, shopping, dining, schools, and everyday conveniences, with additional room for future expansion.

10 Horseshoe Road, Mount Kisco

$3,499,000

5 Beds ⋅ 7 Baths ⋅ 999575 MLS

Located in the highly desirable Petersville Farm neighborhood and within the coveted Chappaqua School District, this exceptional 5-bedroom, 5.2-bath Craftsman-inspired Colonial enjoys sweeping panoramic views overlooking the pristine fairways of the Mount Kisco Country Club. Perfectly sited on over 3 completely flat, park-like acres on a private estate street, this extraordinary residence seamlessly blends timeless architecture, exceptional craftsmanship, and an effortless sense of warmth and sophistication in a serene and picturesque setting. An impressive architecturally striking entry foyer makes a stunning first impression, introducing the home’s sophisticated design, expansive scale, and beautifully crafted interiors. Sophisticated yet inviting, the home is enriched by exquisite architectural details, exceptional millwork, custom built-ins, gleaming hardwood floors, and an open, flowing layout thoughtfully designed for both elegant entertaining and comfortable everyday living. A perfect first-floor layout features expansive, light-filled living and family rooms, each highlighted by dramatic walls of windows, wood burning fireplaces, and direct access to the wraparound deck, creating seamless indoor-outdoor living. The renovated sun-drenched eat-in Chef’s kitchen also opens directly to the deck, while the formal dining room is complemented by an adjacent butler's pantry for effortless entertaining. A private office or library off the living room offers an ideal work-from-home setting. The second floor encompasses a luxurious primary suite featuring an exceptionally renovated spa-inspired bath, along with three additional bedrooms — two sharing a bath and one with its own ensuite bath. Just off the second floor, down a mezzanine staircase, is a spacious bonus/recreation room accompanied by a guest bedroom with an ensuite bath, offering exceptional flexibility for guests, recreation, or extended family living. Walls of windows throughout the home bathe the interiors in natural light while framing breathtaking views of the surrounding landscape and golf course beyond. Rich in character and timeless appeal, every space has been thoughtfully designed with refined style, warmth, and comfort in mind. A wraparound deck and expansive stone patio capture sweeping golf course vistas and provide exceptional outdoor entertaining spaces surrounded by the beauty of the natural landscape. The finished walkout lower level offers outstanding storage space and additional living space, including an expansive recreation room, summer kitchen, full bath, and gym/guest suite with direct access to the spectacular property. Additional highlights include an expansive mudroom, 3-car garage, exterior sprinkler system, and whole-house generator for ultimate convenience and peace of mind. Beautifully embraced by 3.03 acres of professionally landscaped grounds with manicured lawns, specimen trees, and vibrant perennial gardens, the property offers rare privacy, breathtaking scenery, and a setting that lives in perfect harmony with its surroundings. A truly remarkable offering combining sophisticated country living with timeless elegance, sure to captivate the most discerning buyer.

22 Petersville Road, Mount Kisco

$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

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.