Chappaqua Real Estate | Chappaqua Just Listed Properties for Sale

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

11 Kitchel Road, Mount Kisco

$1,150,000

4 Beds ⋅ 3 Baths ⋅ 1024331 MLS

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

49 E Ridge Lane, Mount Kisco

$2,250,000

4 Beds ⋅ 6 Baths ⋅ 1025674 MLS

A rare opportunity to own a private mini-estate on approximately 6.9 acres in Millwood. The main residence offers four bedrooms, three-and-a-half baths and generous living spaces with views of the property’s natural surroundings. Highlights include an eat-in country kitchen with French marble flooring, a living room overlooking the pond and waterfall, multiple fireplaces, radiant heat in the primary bath and extensive closet storage. The property also includes a renovated guest cottage above a three-car garage, plus an additional three-car garage with a private retreat or meditation room featuring pine paneling and a stone fireplace. Outdoor amenities include a heated in-ground concrete pool, pond, waterfall, landscaped gardens, specimen plantings and a three-hole golf course. A distinctive property offering privacy, flexible space and a peaceful setting within the Chappaqua School District. Stay tuned coming soon!

82 Shingle House Road, Millwood

$1,550,000

3 Beds ⋅ 3 Baths ⋅ 1023910 MLS

1926 Colonial with timeless character on a private and level half-acre, walkable to the train station and village in Chappaqua, NY. Circular driveway and classic curb appeal set the tone; inside, hardwood floors flow through an open, light-filled layout. The kitchen opens to a fireplaced family room with deck access, plus a formal dining room and a living room with its own wood-burning fireplace and screened porch. Upstairs, lives as a four-bedroom layout, the primary suite is a true retreat - en-suite bath with sauna and private balcony overlooking the yard with Koi pond plus an office/den, and a full hall bath. The partially finished lower level adds a playroom, wine closet, and storage. Brand new central air conditioning, plus a gas line on the street, offers possible future conversion.

312 Quaker Road, Chappaqua

$1,590,000

3 Beds ⋅ 3 Baths ⋅ 1017997 MLS

Enter into this enduring Colonial blending elegance with today's lifestyle. This home lives like a 4-bedroom and has 4 BR septic. Set on beautifully landscaped property moments away from town, the train and Chappaqua schools. Tastefully expanded and renovated in 2008, this home showcases classic architectural details everywhere. A welcoming foyer opens to a gracious living room and fireplace. A formal dining room with a tray ceiling. Timeless appointed chefs EIK with Wolf appliances, custom cabinetry and marble counter tops, wine refrigerator and breakfast bar. The family room offers a second fireplace and a wall of windows to view the private setting. The sunroom offers custom built-ins and an abundance of natural light. A first floor bonus room and full bathroom works well for guests or an au pair. A mudroom with custom built-ins. Upstairs is the primary bedroom with high ceilings, walk-in custom closet, private study, and en-suite bath with double sinks, marble shower and whirpool bath. Two additional bedrooms, one with custom built-ins, custom closets, and a hall bath. New laundry is located conveniently on the second floor. Outdoors, an expansive deck extending the living space and creating the perfect setting for entertaining, dining and relaxing while overlooking mature landscaping and private grounds that back up to protected green space. Completing the property is a detached two car-garage with generous storage above. The home was extensively renovated and expanded in 2008 offering the finest architectural finishes. An exceptional offering. New roof 2024 and new 4 bedroom septic 2026.

131 Douglas Road, Chappaqua

$1,299,000

4 Beds ⋅ 3 Baths ⋅ 1013321 MLS

Set on a level .64-acre property along one of Chappaqua's most sought-after neighborhood streets, 9 Oak Hill Road is a beautifully updated 4-bedroom, 3-bath Raised Ranch that offers spacious, light-filled living in a peaceful natural setting. A covered front porch welcomes you into an entry foyer, where a short mezzanine staircase leads to the main living level. Here, a gracious living room with a picture window flows effortlessly into the adjoining dining room, creating an inviting space for everyday living and entertaining. Adjacent to the dining room, the eat-in kitchen completes the home's open, functional layout. Oversized windows at both the front and rear fill the living areas with natural light, while the property's exceptional setting—backing to the Saw Mill River Audubon Society's Cameron-Murfeldt Sanctuary—offers privacy, scenic views, and a charming pond that enhances the tranquil landscape. The eat-in kitchen is thoughtfully designed with white cabinetry, stainless steel appliances, a picture window, and a sun-filled breakfast area that enjoys morning light. A door opens directly to the deck, making outdoor dining and weekend barbecues effortless. Three well-proportioned bedrooms are located on the main level, including a spacious primary suite with two closets and a private bath. A corner bedroom enjoys windows on two sides, while the third bedroom features two front-facing windows and a generous double closet. Every bedroom in the home is outfitted with custom California Closets, providing beautifully designed, highly functional storage and organization. The finished walk-out lower level provides exceptional additional living space with a generously sized family room featuring hardwood floors, a decorative electric fireplace, and sliding glass doors that open to the patio. A private, expansive fourth bedroom with hardwood floors and a double closet, a full bath with shower, laundry area, utility room, abundant storage, and direct access to the attached two-car garage complete this versatile level. Set back from the road with a level driveway and expansive front lawn, this inviting home offers the perfect balance of comfortable living, effortless entertaining, and the peaceful beauty of its park-like surroundings.

9 Oak Hill Road, Chappaqua

$1,995,000

4 Beds ⋅ 3 Baths ⋅ 882412 MLS

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

12 Brandon Drive, Mount Kisco

$2,200,000

4 Beds ⋅ 4 Baths ⋅ 1021493 MLS

Welcome to 10 Crestview Drive, a beautifully updated 1990 colonial that perfectly blends classic elegance with updated modern luxury within the highly sought-after Heritage Court neighborhood. This exceptional property offers the rare combination of an intimate community feel and tremendous, serene privacy, all set on nearly an acre of flat, meticulously manicured grounds. Inside, you will find a bright and spacious layout featuring four well-proportioned bedrooms, all on the same level, and designed for ultimate comfort. The main floor features a three-car garage, mudroom, eat-in-kitchen with easy access to the deck, and backyard beyond, open floor plan, living room, dining room, and office. Also of note, this turnkey gem provides an unparalleled and truly unique opportunity for the next lucky buyers: a rare, one-time option to choose between the Chappaqua or the Byram Hills School District at closing. This is turnkey luxury at its finest!

10 Crestview Drive, Pleasantville

$579,000

2 Beds ⋅ 1 Baths ⋅ 1021554 MLS

Welcome to 309 N. Greeley Avenue. This lovely first floor Town House in the sought-after Chestnut Oaks Community is conveniently located to the heart of downtown Chappaqua. With the award-winning Chappaqua School District and proximity to a Metro North station, this property will not last! This Two Bed, 1 Bath unit has a great layout with a front and back patio! There are no stairs (just one step-down to a sunken Living Room)....enter into this unit and all rooms are one the same level! The main living room is both open and airy with a high ceiling, fireplace and two sliding glass doors leading out to lovely patios and open space. The complex features a swimming pool, tennis and a garden. Make your appointment today!

309 N Greeley Avenue Unit #5C, Chappaqua

$549,000

2 Beds ⋅ 1 Baths ⋅ 993303 MLS

Opportunities like this do not come around often in Chappaqua, and when they do, they tend to move quickly. What is being offered at 58 Maple Ave is a flat, level, in-town parcel with an existing 2-bedroom, 1-bath cottage set back from the road among towering pines, in one of Westchester County's most coveted villages. Whether a buyer chooses to develop the land, renovate what is there, or simply occupy the existing structure while planning next steps, the opportunity here is defined first and foremost by the location and the lot. The cottage itself, built in 1930 and totaling 711 square feet, is being sold strictly as-is. It sits on a 0.28-acre lot with driveway parking and includes a front deck, a patio, and a yard with a quiet, private feel that genuinely surprises you given how close you are to the center of town. Inside, the main level includes a great room with cathedral ceilings and built-in features, a kitchen, two bedrooms, and a full bath. A partial basement with Bilco door access houses laundry and mechanicals. The structure has a history as a consistently rentable asset in a market where rental demand is strong and vacancy is rare, which speaks to the enduring appeal of this particular address regardless of what a future owner ultimately decides to do with it. The location is the defining feature and the reason this property commands the attention it does. You are minutes on foot from the Chappaqua Metro-North Station, putting Midtown Manhattan within comfortable commuting distance without the stress of a car or a parking lot. The village's boutique shops, restaurants, and parks are equally walkable, giving this address an everyday livability that most Westchester properties simply cannot replicate. For those who travel frequently for business, Westchester County Airport is also easily accessible. This is a genuinely rare convergence of walkability, transit access, and village character that defines the upper end of what Chappaqua real estate has to offer. The property falls within the Chappaqua Central School District, one of the most highly regarded public school systems in New York State and a consistent driver of demand in this market. Flat lot, set-back privacy, walk-to-train location, and Chappaqua schools.

58 Maple Avenue, Chappaqua

$1,099,000

2 Beds ⋅ 3 Baths ⋅ 1004449 MLS

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

4 Annes Wood Lane, Mount Kisco

$1,594,000

3 Beds ⋅ 3 Baths ⋅ 1013791 MLS

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

676 Hardscrabble Road, Chappaqua

$3,100,000

5 Beds ⋅ 6 Baths ⋅ 990281 MLS

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

2 Heathcote Drive, Mount Kisco

$1,998,999

4 Beds ⋅ 4 Baths ⋅ 1011189 MLS

Nestled on over an acre of beautifully landscaped grounds in the highly sought-after Chappaqua School District, this exceptional residence offers a rare blend of privacy, craftsmanship, and versatility. Behind a gated entrance, mature specimen plantings, expansive lawns, and a tranquil natural setting create a true private retreat just minutes from downtown Chappaqua and Metro-North. Thoughtfully improved throughout the years, the home features cedar siding, Anderson windows and sliding doors, custom hardwood flooring with intricate inlay detail, reinforced structural beams, remote-controlled skylights, and numerous mechanical upgrades. Dramatic ceilings, walls of windows, and sun-drenched living spaces create an inviting atmosphere designed for both everyday living and entertaining. The eat-in kitchen is appointed with custom cabinetry, premium stainless steel appliances, a center island, and seamless access to the outdoor deck. Formal and informal living spaces flow effortlessly throughout the main level, highlighted by a dramatic living room with soaring ceilings, oversized windows, and a marble fireplace. The luxurious primary suite serves as a private retreat featuring custom California Closets and a stunning spa-inspired bath with a freestanding soaking tub, oversized glass-enclosed shower with body jets and bench seating, custom mahogany detailing, designer lighting, and exceptional finishes throughout. Renovated bathrooms throughout the home showcase custom tilework, premium fixtures, and thoughtful spa designs. Additional highlights include California Closets throughout, intercom and surround sound systems, smart gate access, surveillance cameras, irrigation system, renovated garage, and a charming detached storage shed. Outdoor living is equally impressive with expansive decking, a remote-controlled SunSetter awning, and peaceful grounds designed for entertaining and relaxation. A truly special offering combining privacy, quality craftsmanship, modern conveniences, and exceptional flexibility in one of Westchester County's most desirable communities.

4 Old House Lane, Chappaqua

$1,100,000

5 Beds ⋅ 3 Baths ⋅ 991248 MLS

Some homes have good bones. This one has great ones in a private setting. Nestled in Chappaqua's beloved Seven Bridges neighborhood, this 1934 Colonial sits on nearly three-quarters of an acre where tree-lined streets and a true sense of community appeal to buyers who embrace Chappaqua and remain for years. Original hardwood floors, a wood-burning fireplace, crown molding, and a screened porch speak to craftsmanship that simply cannot be replicated. An updated kitchen with granite countertops, wood cabinetry, and a gas range bring real functionality to the floor plan. Main floor offers living room with attached screened in porch, formal dining room, family room / breakfast room, kitchen, huge en-suite bedroom and laundry room. Upstairs holds four more bedrooms, primary ensuite and another full bathroom. Basement has slop sink with laundry hook up and mechanicals. A 2-car garage with a huge walk-up attic, and two additional attics accessed from inside the home give you the space and storage to match your needs. Bring your vision and make it yours in one of Westchester's most sought-after school districts.

2 Turner Drive, Chappaqua

$1,849,000

1005784 MLS ⋅ 21 BLDG.

Investment opportunities like this rarely become available in Downtown Chappaqua. Welcome to 21 King Street, a rare mixed-use commercial property offering exceptional visibility, convenience, and income potential in one of Westchester's most desirable downtown locations. The building features two street-level retail storefronts and a residential apartment above, creating multiple income streams and long-term investment value. A standout feature is the private rear parking lot accommodating approximately 14 vehicles—an increasingly valuable asset in downtown Chappaqua. In addition to serving the property's tenants and customers, the parking area may offer additional income potential through rental opportunities. The rear lot also presents future upside, as it may provide opportunities for expansion or redevelopment, subject to municipal approvals and zoning requirements. Ideally positioned just moments from shops, restaurants, and the Metro-North train station, 21 King Street benefits from excellent foot traffic and a highly sought-after location. Whether you are an investor seeking diversified income streams, an owner-user looking to establish a presence in Chappaqua, or someone searching for a prime long-term asset, this is a unique opportunity to own a landmark property in the heart of town with both immediate cash flow and future potential.

21 King Street, Chappaqua

$879,000

3 Beds ⋅ 3 Baths ⋅ 1006886 MLS

Welcome to Apple Hill Farm, sitting on highly desirable, 37+ Wooded Acres. Where calm meets comfort. This corner Townhome, located in a cul-de-sac for added privacy, features a manicured lawn and a carefully curated garden. Experience modern elegance in this home, with high ceilings, lots of Windows and Skylights that bring abundant natural daylight and sunlight indoors. It has 3 Bedrooms and 2.5 Bathrooms, many updates throughout the home, including the exterior deck. The Living Room has custom built-ins. An inviting Dining Room for memorable meals and an Eat-in-Kitchen with quartz countertops and stainless steel appliances, both rooms have sliding doors onto the deck. It features hardwood floors throughout, many closets and storage spaces. The Primary Bedroom has a Juliet Balcony, En-Suite bathroom with Double sink vanity, Second Bedroom with Skylights, Third Bedroom with Hallway Bathroom. Close to Train, Close to Downtown Dining and Shops, Close to Schools. Property includes 1-Car Attached Garage with Driveway for 1 additional car. Amenities include: Inground Pool and Tennis Courts.

2 Timberland Pass, Chappaqua

$1,025,000

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

$989,000

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

$2,699,000

4 Beds ⋅ 5 Baths ⋅ 998577 MLS

Tucked away on over two exquisitely landscaped acres in one of Chappaqua’s most prestigious enclaves, this exceptional newly constructed modern home redefines luxury living through a masterful blend of architectural sophistication, cutting-edge efficiency, and timeless elegance. Designed with a discerning eye and crafted with uncompromising quality, this magazine-worthy residence offers the ultimate turnkey lifestyle only moments from downtown Chappaqua, Metro North, and top-ranked schools. A dramatic arrival sets the tone as you enter through oversized custom doors into sun-drenched interiors framed by soaring 10-foot ceilings, expansive walls of glass, and wide-plank white oak flooring throughout. The home’s seamless open-concept design was thoughtfully curated for both grand-scale entertaining and intimate everyday living, creating a warm yet elevated atmosphere in every room. At the heart of the home is a spectacular chef’s kitchen worthy of a luxury design showroom, featuring premium professional-grade appliances, bespoke custom cabinetry, oversized quartzite island, designer lighting, and exceptional prep and storage space. Flow effortlessly into the breathtaking great room anchored by a statement fireplace and oversized sliders that open to a covered outdoor lounge, creating a true indoor-outdoor living experience. The primary suite is a private sanctuary rivaling a five-star resort, complete with a boutique-inspired dressing room and a spa-caliber bath featuring radiant heated floors, custom marble steam shower, soaking tub, and designer vanities. Generously sized ensuite bedrooms provide exceptional comfort and privacy for family and guests alike. The fully finished walk-out lower level elevates the home even further, offering an extraordinary extension of living space ideal for a private wellness retreat, gym, media lounge, golf simulator, wine tasting room, or entertainment venue. A striking custom wine display serves as a dramatic focal point and conversation piece. Every inch of this residence reflects a commitment to luxury and modern convenience, including geothermal heating and cooling, smart-home integration, premium fixtures and finishes, oversized heated garage space, and meticulously curated landscaping designed for both beauty and privacy. A rare offering that blends modern elegance, privacy, and convenience just under an hour from Manhattan. Come see a flawless fusion of contemporary design, superior craftsmanship, and effortless luxury set within one of Westchester’s most coveted communities today.

40 Hamilton Drive, Chappaqua

$2,499,000

3 Beds ⋅ 4 Baths ⋅ 973551 MLS

Set on beautifully landscaped grounds in one of Chappaqua’s most coveted neighborhoods, this exceptional 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

$2,895,000

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 Fall 2026. Early buyers will have the rare chance to customize many 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

$1,665,000

931118 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

$809,000

4 Beds ⋅ 3 Baths ⋅ 981423 MLS

Welcome home to this well-maintained residence in the heart of vibrant Chappaqua! This 4 bedroom and 2.5 full bathroom house is located in the award-winning Chappaqua school district. Step inside to discover gleaming hardwood floors throughout, a cozy living room with a wood-burning fireplace, and a bright, charming dining room. The kitchen features ample cabinetry, granite countertops, and brand-new stainless-steel appliances. The spacious primary suite, versatile enough to serve as a large family room, includes a walk-in closet and a newly renovated en-suite bathroom. Upstairs, three generously sized bedrooms await, including a second primary suite with a walk-in closet, and a second full bathroom. Additional highlights include a welcoming front porch, expansive attic storage, a full basement with crawl space, and a circular driveway accommodating up to six cars for effortless access. Enjoy summer days in the fenced backyard—perfect for gatherings, gardening, or basking in the sunshine. This prime location is minutes from the Train Station, library, town hall, post office, shops, restaurants, top-rated schools, and easy access to major parkways. Zoned for versatility, this property offers a potential for conversion back to commercial use, for an attorney’s office, dental practice, or other professional ventures in the bustling heart of Chappaqua. Don’t miss your chance to own this delightful home with endless possibilities! The house is no longer furnished as shown in the photos.

73 S Bedford Road, Chappaqua

$639,000

966226 MLS

A rare opportunity to build mixed use consisting of commercial/professional and multi-family with huge income potential. The 1st floor as commercial and the 2nd and 3rd floors residential apartments. An architect has drawn 4 concept plans ranging from commercial space and lobby with (4) 2-bedroom apartments to commercial space and lobby with (6) 1-bedroom apartments. One example: 1st floor commercial/professional space = 500 sf 1st floor lobby = 562 sf 2nd floor 3 residential units = 2,546 sf 3rd floor 3 residential units = 2,5646 sf Each residential apartment = 760 sf Parking spaces = 10 Land in Chappaqua is indeed a rare commodity, especially one with this amount of upside potential - don't miss this unique opportunity. The concept plans are available upon request.

65 S Bedford Road, Chappaqua

$3,900,000

4 Beds ⋅ 6 Baths ⋅ 966260 MLS

Designed without compromise and executed to perfection, this custom Georgian Colonial by Nasser Nakib Architect sets a new standard for luxury living. Eleven-foot ceilings, an effortless open layout, and walls of windows create a light-filled, airy feel throughout. A front-to-back foyer with floating staircase makes a striking first impression, while wide plank wood floors, a slate roof, and full smart home technology reflect the quality behind every detail. The gourmet kitchen is beautifully appointed with state-of-the-art appliances, double islands, and a hidden walk-in pantry, flowing seamlessly into the breakfast area and family room with fireplace. Doors open to a covered patio overlooking the pool and capturing spectacular sunset views. Upstairs, the primary suite is a true sanctuary with two spa-like baths, each with a soaking tub. One features a refined dressing room with island; the other offers an oversized rain head and steam shower. Every room of the suite opens to a private terrace. Three additional ensuite bedrooms and laundry complete the upper level. The lower level includes a cabana bath with shower and double WCs for pool access, a recreation room, expansive gym, conditioned wine cellar, additional laundry, and a substantial unfinished space. Beautifully landscaped grounds with slate patio, pool, and spa. Located in the Chappaqua School District with easy access to town, train, and major highways. 4+ car attached garage. A must see!

16 Taylor Road, Mount Kisco

$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

$2,990,000

6 Beds ⋅ 6 Baths ⋅ 909816 MLS

Nestled in breathtaking natural surroundings, this modern architectural masterpiece by renowned designer Myron Goldfinger offers three levels of striking contemporary design. The residence features a soaring three-story curved ceiling, a dramatic floating staircase, and expansive open-plan living and entertaining spaces that frame the home’s private setting. The main-level primary suite provides a serene retreat, while the sleek, state-of-the-art kitchen is ideal for both everyday living and entertaining. Additional highlights include a fitness room, Shoreline pool with cabana, and a private tennis court. A 4+ car attached garage and below-ground oil heating add convenience. Located just 45 minutes from New York City, this one-of-a-kind residence blends luxury, privacy, and timeless modern design.

20 Bessel Lane, Chappaqua

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