Chappaqua Real Estate | Chappaqua Properties for Sale

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

$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

$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

$1,594,000

3 Beds ⋅ 3 Baths ⋅ 1013791 MLS

Renovated and Reimagined Colonial on Spectacular Park-Like Grounds, this exceptional residence includes a separate cottage-style bonus building that offers endless possibilities. Whether envisioned as a private home office, artist’s studio, yoga or fitness center, man cave or an inspiring creative workspace, this detached structure provides exceptional flexibility and privacy. Nestled amid the lush grounds and mature landscaping, it serves as a peaceful extension of the home and creates a rare opportunity for today’s work-from-home lifestyle or entrepreneurial pursuits. At the heart of the home, an original stone wood-burning fireplace serves as a stunning focal point, infusing the living space with warmth, character, and timeless charm. Perfect for cozy winter evenings, holiday celebrations, and memorable gatherings with family and friends, this impressive architectural feature creates an inviting atmosphere that embodies the true spirit of home. The stunning chef’s kitchen features premium stainless-steel Thermador appliances, elegant quartz countertops, a spacious walk-in pantry, and seamless access to an oversized slate patio—ideal for indoor-outdoor entertaining. The captivating primary suite offers soaring beamed ceilings, a generous sized walk-in closet, and a luxurious spa-inspired bath complete with dual vanities and a classic clawfoot soaking tub. Convenient second-floor laundry with storage enhance everyday living. Additional highlights include all-new Anderson windows, all new electrical, all new plumbing, new roof, new c/air, new Navien system, energy-efficient blown-in insulation, solid wide-plank oak flooring, and exquisite custom millwork throughout. The separate cottage building has all new electrical, blown insulation, windows, flooring and roof. Located minutes from the Metro North Train Station and downtown Chappaqua, you'll have quick access to commuter routes and a charming village filled with shopping, restaurants and community events. A rare offering that perfectly blends timeless charm with sophisticated modern updates, all set within a serene and private setting. The outbuilding / studio can be converted back to a garage. Square footage does not include the studio space.

676 Hardscrabble Road, Chappaqua

$1,849,000

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

$839,999

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

$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

$2,995,000

4 Beds ⋅ 6 Baths ⋅ 992104 MLS

Exceptional new construction opportunity in the highly sought-after Chappaqua School District, currently being built with anticipated completion this November 2026. Early buyers will have the rare chance to customize some of the final finishes and tailor the home to their personal style. This thoughtfully designed home offers 4 bedrooms and 5.1 bathrooms, with a highly desirable layout that lives like a larger home thanks to additional flexible living spaces. The main level features an open-concept design with seamless flow between the kitchen, dining area, and informal living room with fireplace. The kitchen is equipped with a premium Thermador appliance package and includes sliding glass doors leading to the back patio, while the family room also features sliders to the covered patio—creating a seamless connection and the perfect setting for indoor-outdoor entertaining. In addition to the formal dining room, formal living room, and powder room, the main level also includes a versatile room adjacent to a full bathroom, ideal for use as a private office, den, or guest accommodations. The fully finished walk-out lower level adds substantial additional living space, including an additional room with sliding glass doors and access to a full bathroom—well-suited for a variety of uses including extended living, recreation, or work-from-home needs. The primary suite is a true retreat, showcasing a tray ceiling, two oversized walk-in closets, and a luxurious bathroom with double vanity, soaking tub, separate shower, and private toilet room. A second-floor laundry room adds everyday convenience. Just a few additional highlights include 9-foot ceilings throughout, 4" oak hardwood floors, high-end finishes across all levels, an oversized two-car garage leading to a mudroom with custom cubbies and closet, a high-efficiency heat pump and cooling system, pre-wiring for a future electric vehicle charging station, and a security system. Privately set on over an acre of land on a cul-de-sac street and surrounded by mature trees, this home offers a peaceful setting while remaining close to parks, town, schools, and transportation. A rare opportunity to own a brand-new, thoughtfully designed home with exceptional flexibility in an ideal Chappaqua location.

39 Barnes Lane, Chappaqua

$1,590,000

3 Beds ⋅ 4 Baths ⋅ 984583 MLS

Welcome to this sophisticated carriage home at 17 Lila Lane, offering a rare blend of contemporary luxury and maintenance-free living within the prestigious Chappaqua Crossing community. The thoughtfully designed layout is anchored by a gorgeous chef’s kitchen, featuring a large center island with ample seating and a premium JennAir appliance package. Equally enticing is the coveted first-floor primary suite, providing a serene sanctuary with a spa-inspired ensuite bathroom and an expansive walk-in closet. The second level serves as a versatile retreat, home to a spacious second bedroom, a dedicated home office/bedroom, an inviting sitting area, and a gorgeous private terrace. Additional living space abounds in the fully finished lower level, perfectly suited for a high-end home gym and a cozy media den, while the attached two-car garage comes equipped with an EV charging station for modern convenience. Residents enjoy an unparalleled "village within a village" lifestyle defined by sprawling green space and scenic walking trails, with exclusive access to a luxury clubhouse and sparkling pool. Situated in the heart of Chappaqua, this residence is just steps from Whole Foods, Life Time Fitness, delicious restaurants, and offers the convenience of a private community shuttle to the Metro-North for a seamless commute to Manhattan.

17 Lila Lane, Chappaqua

$4,500,000

5 Beds ⋅ 7 Baths ⋅ 950756 MLS

1906 Grandeur. 2026 Luxury: The Ultimate Gated Sanctuary. Perched majestically atop a private hilltop, this gated 7,800-square-foot, five-bedroom estate presents a rare convergence of Gilded Age prestige and contemporary luxury. Believed to have been commissioned in 1906 for railroad magnate A.H. Smith, the residence has been masterfully renovated to honor its historic soul, featuring original interior stone walls and soaring ceilings that strike a perfect balance between grand scale and intimate warmth. Anchored by three distinctive hearths, the home is designed for both elegant living and everyday ease. A sun-drenched chef’s kitchen showcases a central island, dramatic overhead skylight, and professional-grade appliances. Unique architectural moments—including a circular-skylit Stargazer’s Nook—add character and charm, while the versatile five-bedroom layout offers both a magnificent two-story primary wing and a coveted first-floor private suite. Set on more than four exceptionally private acres, the grounds unfold as a true outdoor sanctuary, featuring a beautiful pool and spa (32x20), refined pergola terraces ideal for entertaining, and a private tennis court. From its commanding hilltop position, the estate delivers an unparalleled sense of privacy, security, and timeless elegance. Welcome home!

150 Old Farm Road N, Chappaqua

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