Chappaqua, N.Y.

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The name Chappaqua is derived from an Algonquin word which translates as “running water”. Lakes, ponds and streams are abundant among the rolling wooded hills of Chappaqua. A large portion of the land has been preserved as undeveloped, open space, which helps to create Chappaqua’s rural feeling. With faithful adherence to environmental and architectural review, the town has managed to retain a country feeling with a great deal of privacy for individual homes. Architectural styles range from antique colonials to exquisite contemporaries.

From the Chappaqua train station, New York City’s Grand Central Station is a 50-minute ride. White Plains is only ten minutes away and the Saw Mill River Parkway runs right by town. The great combination of privacy and accessibility makes Chappaqua very attractive for New York City commuters. In 1864, Horace Greeley took up residence in Chappaqua and more recently, former President Bill Clinton and Senator Hillary Clinton made Chappaqua their home. Residents place a high priority on education and the Chappaqua Central School District ranks consistently among New York State’s best schools with Scholastic Aptitude Test scores well exceeding the average.

ACTIVE LISTINGS:

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.

$3,450,000 Active

20 Bessel Lane Chappaqua, New York

6 Beds 6 Baths 8,200 SqFt 4.11 Acres

Exciting and new state-of-the-art expansion and renovation by highly recognized local developer, Tavo Development teaming with noted architect Teo Seguenza. Ready for occupancy in Spring 2026. Meticulous attention to detail, years of experience and master craftsmanship are combined in this new offering, encompassing 5,536 sq ft, 4 bedrooms, 5 full and 2 half baths, a finished walk-out lower level and all the modern amenities for today’s discerning buyer. The light-filled main level highlights a chef’s kitchen with island and breakfast room, formal living room and dining room, family room, large mudroom and a screened in porch. Upstairs, the primary suite is enhanced with a spa-like bath and oversized walk-in closet. Two additional ensuite bedrooms, bonus room with access to a large balcony and laundry complete the upper level. The lower-level with an exercise room, lounge, laundry and full bath segues to the outdoors with almost an acre of flat usable grounds and site plan approval for a pool. Interior pictures displayed are samples of previous Tavo built homes. A perfect combination of style, space, and comfort. Close to town, highways and 50 minutes to NYC.

$2,850,000 Pending

211 Bedford Road Chappaqua, New York

4 Beds 7 Baths 5,536 SqFt 0.95 Acres

A truly rare Chappaqua mini-estate with pool and tennis, offering resort-style living just a short walk from the town and train. Privately perched atop a hill and approached by a sweeping stone-lined driveway, this property delivers an exceptional blend of privacy, presence, and convenience—moments from shops, dining, and Metro-North. The expansive grounds are designed for all-season enjoyment, featuring a heated pool, tennis court, playground, and putting green, creating a true at-home retreat rarely available so close to town. A classic wraparound porch sets the tone for relaxed indoor-outdoor living, perfect for morning coffee, sunset cocktails, and effortless entertaining overlooking the beautifully landscaped property. The home balances estate-style scale with a warm, welcoming feel, making it equally suited to large gatherings and everyday living.An irreplaceable , country-chic Chappaqua offering where land, privacy, and best-in-class amenities meet true walk-to-all convenience—an ideal opportunity for buyers seeking a mini-estate lifestyle in a prime, in-town location.

$2,750,000 Active

276 Quaker Road Chappaqua, New York

6 Beds 4 Baths 6,532 SqFt 2.68 Acres

Meticulously maintained, beautifully appointed 4-bedroom, 4 full and 1 half-bath Colonial set on a level acre at the end of a quiet cul-de-sac in prestigious Inglenook Farm in the coveted Byram Hills Schools. A grand and light-filled two-story entry welcomes you into this refined home featuring 9-foot ceilings on 1st and 2nd levels, oak flooring, and custom moldings and trim throughout. Formal living and dining rooms lead to a Chef's eat-in kitchen with granite countertops, oversized island, stainless appliances and dining area. The kitchen opens to a spacious family room with wood burning fireplace and doors to an expansive deck overlooking the serene, park-like backyard. A mudroom off the kitchen provides everyday convenience, and a separate back bonus/recreation room adds flexible space for work, play, or relaxation. Upstairs, the primary suite features a spa-like bath, dressing area, and oversized custom-outfitted closet. The finished legal walkout lower level includes a large recreation room, gym, full bath, and ample storage. Other highlights include a large laundry room, large walk-in pantry and a 3-car attached garage. Located just minutes to the towns of Chappaqua and Armonk, in the Byram Hills School District and just 45 minutes from NYC, this home is not to be missed.

$2,599,000 Active

17 Byram Meadows Road Chappaqua, New York

4 Beds 5 Baths 6,640 SqFt 1.02 Acres

Custom design your dream home in a seamless process with ZappiCo, Westchester County's premier Real Estate Developer! This luxurious home is to-be-built in the highly desirable Chappaqua school district. With 4 spacious bedrooms and 2.5 beautifully appointed bathrooms, this home will be meticulously crafted with the finest materials and attention to detail. As you enter, you will be greeted by an open concept living and dining area, perfect for entertaining guests or relaxing with loved ones. The gourmet kitchen will feature an open layout with quartz countertops and semi-custom cabinetry. The open concept main level will also offer a family room & living room - perfect for those who work from home or need a quiet space to study. Upstairs, you will find a spacious primary suite complete with a spa-like en suite bathroom and walk-in closet, as well as three additional bedrooms with ample closet space. Other features of this home will include hardwood flooring throughout, energy efficient windows, 2-zone central air, and a full finished basement (1,000 sf. incl. in total sf) ready for your personal touch. Outside, landscaping is included to create your own oasis. Located just a short distance from local restaurants, shops, and parks, this home offers the perfect blend of luxury living and convenience. With the ability to customize your finishes and personal touches, this to-be-built home is the perfect opportunity to create your dream home in Chappaqua. Photos are representative of previously built/sample home and may show options not included in the Supreme Spec package.

$2,000,000 Active

00 Gray Rock Lane Chappaqua, New York

4 Beds 3 Baths 4,500 SqFt 0.97 Acres

Living like a four-bedroom, this gracious and spacious three-bedroom plus bonus room modern Colonial shines from top to bottom from the meticulous maintenance and updates by the original owners. A welcoming, grand two-story entry introduces a large formal living room brightly illuminated by large front- and side-facing windows, recessed lighting and a wood-burning fireplace. French doors add light from the adjoining sun room, which can easily serve as a home office. Host feasts or fests in the traditional front-facing formal dining room. The kitchen is a cornucopia of delights: custom white wood cabinetry, natural stone countertops, subway tile backsplash, massive center island with plenty of prep space and a breakfast bar for quick dining, and high-end stainless-steel appliances including two Wolf electric convection ovens, a Wolf induction cooktop, large Sub-Zero refrigerator/freezer, built-in Sharp microwave, Miele dishwasher and Sub-Zero wine fridge. Open to the family room is the adjoining breakfast area with built-ins and sliding glass door to the deck for easy BBQ or dining alfresco. Large, rear, south-facing windows and a sliding glass door to the deck beam natural light throughout the spacious family room with its skylit cathedral ceiling, built-in cabinetry and back staircase ascending to the upper level. A powder room and a well-organized laundry/mud room with access to the three-car garage complete the main level. A sweeping staircase ascends to the upper level, home to three bedrooms, three bathrooms and a bonus room, which include the luxurious front-to-back primary suite endowed with a king-sized bedroom, an adjoining sitting or exercise area, walk-in closet, and an elegant, private, skylit, spa-like ensuite bath with wide, two-sink vanity, spa tub, separate shower stall, and radiant heat; two comfortably-sized bedrooms include a front-facing bedroom with two closets and private ensuite bath with shower over bathtub, and a rear-facing bedroom with door to hall bath with two-sink vanity and shower over bathtub; and an extra-large bonus room with closet, which can serve as a den, guest quarters, lounge, office, study, etc. All upper-level rooms have hardwood flooring beneath wall-to-wall carpeting. Designed for entertainment, the finished walk-out lower level showcases two large recreation spaces with a sliding glass door to a large deck, an exercise area (possible in-law or au pair space) and a full bath with shower. Solid, poured concrete foundation, recently updated mechanicals, an automatic backup generator and a newer roof to top it off. Lovely landscaping envelopes the residence. A velvety green lawn rolls out in the back yard, ideal for a catch or lounging about. Sited on a private cul-de-sac just a short drive to schools, shops, town and train. A gem!

$1,999,999 Pending

19 Stony Hollow Chappaqua, New York

3 Beds 5 Baths 3,880 SqFt 1.182 Acres

Welcome to 26 Wallace Way — a standout residence in the coveted, sold-out Chappaqua Crossings Carriages community. Thoughtfully designed and impeccably finished, this first-floor primary bedroom home elevates townhouse living with refined interiors, dramatic architecture, and a setting that is both private and connected.The main level makes an immediate impression with a dramatic double-height living room, where oversized windows flood the space with natural light and tranquil views of the open grass courtyard placing the home at the heart of one of the community’s most desirable locations. The chef’s kitchen flows seamlessly into the living and dining areas, anchored by a generous center island, custom cabinetry, and premium appliances, creating an ideal layout for both everyday living and entertaining. The primary suite offers effortless main-level living, complete with a spa-inspired bath and an expansive walk-in closet. A stylish powder room, along with thoughtful storage, laundry, and garage access, completes the level.Upstairs, a sunlit loft serves as a versatile lounge or gathering space with western exposure showcasing beautiful sunsets beyond. From here, step out to the private outdoor terrace overlooking landscaped grounds and treetops—a peaceful retreat perfect for morning coffee or evening unwinding. This level also features a well-appointed second bedroom, a full bath, and a dedicated home office, along with large walk-in closets that enhance both comfort and functionality.The living space extends even further with a finished basement, ideal for an additional bedroom, media room, or gym, and is complemented by a third full bathroom. The home also includes dedicated areas on all three levels for a future elevator, offering long-term flexibility and ease of living.Just a short walk from the clubhouse and pool, the amenities feel like a natural extension of your home. Residents enjoy walkable access to the fitness center, Whole Foods, Life Time, shops, and restaurants, along with a dedicated shuttle to the train for effortless commuting.Built by Toll Brothers, known for exceptional quality and craftsmanship, 26 Wallace Way offers a rare blend of first-floor primary living, dramatic architectural design, privacy, and resort-style amenities in one of Chappaqua’s most sought-after communities.

$1,780,000 Active

26 Wallace Way Chappaqua, New York

2 Beds 4 Baths 2,945 SqFt 0.06 Acres

Exceptionally renovated and truly turnkey, this striking Whippoorwill cul-de-sac Contemporary is located in the highly acclaimed Chappaqua School District. Dramatic, airy, and light-filled, the 4-bedroom home is set in a serene and sought-after neighborhood, offering both privacy and convenience. A wall of windows, skylights, soaring ceilings, and an open floor plan flood the interiors with natural light. The living and family rooms—each featuring a fireplace—flow seamlessly for effortless everyday living and entertaining. Hardwood floors extend throughout, while outdoor spaces include a stone patio and wraparound deck overlooking lush, park-like grounds. Extensive upgrades include new above-ground oil tanks, new windows, a new roof, new mechanicals, and more. Enjoy lake rights to Whippoorwill Lake and easy walking access to the Whippoorwill trails. This exceptional home is a rare offering and sure to delight the most discerning buyer.

$1,749,000 Pending

2 Whippoorwill Close Chappaqua, New York

4 Beds 4 Baths 3,022 SqFt 1.59 Acres

To be Built! Spring 2025 move-in. 3485 square feet ! Still time to personalize interior finishes at our luxury Design Studio. Final building for sale at Chappaqua Crossing! A roaring fireplace will warm the entire home. A private rooftop terrace with included outdoor gas fireplace, 2- car garage and the highest quality interior appointments you've come to expect from Toll Brothers round out this spectacular residence! The exquisite foyer presents sweeping views of this home's open-concept floor plan and luxurious finishes. Overlooking the great room and accompanied by a casual dining area, the gorgeous kitchen is the perfect environment for entertaining guests with wraparound counter space and a sprawling central island. The spacious primary bedroom suite offers a luxurious bath and impressive closet space. The private workspace on the second floor is the perfect spot to work from home. Once completed this 91- Townhome community will surround it's owners with a delightful and eminently walkable village full of the niceties that make Westchester living so extraordinary; such as charming cafes, fitness center, golf, shuttle to train into Manhattan, walking trails, outdoor pool, clubhouse which will open this Spring, and much more.

$1,658,995 Pending

11 Wallace Way 18 Chappaqua, New York

2 Beds 4 Baths 3,353 SqFt 0.08 Acres

TO BE BUILT. Move-in Spring 2026. Spacious 3485 square feet ! Still time to personalize interior finishes by visiting our luxurious Design Studio. As you enter the Millwood Elite, the exquisite foyer presents sweeping views of this home's open-concept floor plan and luxurious finishes. A large center island in the kitchen overlooks the casual dining area. The great room is the perfect setting for relaxation with its cozy fireplace and ample natural light. The appealing primary bedroom suite boasts a lavish bath and ample closet space. The second-floor loft offers endless opportunities for a flexible space. The community is situated just minutes away from shopping, dining, and entertainment. Expand your living space onto the outdoor terrace, complete with an outdoor kitchen and built-in grill.

$1,599,995 Pending

15 Wallace Way 20 Chappaqua, New York

3 Beds 4 Baths 3,353 SqFt 0.08 Acres

Timeless elegance meets modern comfort in this beautifully updated Colonial home. Double entry front doors open to a gracious foyer, setting the stage for the home’s expansive and light-filled layout. At its center, the renovated chef’s kitchen impresses with gleaming Caesarstone countertops, professional-grade stainless steel appliances, dual dishwashers, an oversized island with prep sink, ample counter seating, and abundant pantry and cabinet storage. Designed as the true heart of the home, the kitchen flows into a sun-drenched four-season sunroom—an inviting space for casual dining, quiet reading, or relaxed evenings. Off the kitchen is an elegant dining room and spacious living room perfect for grand entertaining and everyday comfort. An elegant powder room and home office add refinement and functionality. Thoughtfully connected to the main living areas, a bedroom with full bath, family room, and sitting room provide flexible space for everyday living, while a separate entrance offers the option of a private guest or in-law suite. Upstairs, the large primary suite is a luxurious sanctuary, featuring an expansive walk-in closet and a spa-like full bathroom with large glass shower. Two additional bedrooms share a well-appointed full bath with bathtub. An upstairs laundry area provides convenience at your fingertips.
The lower level offers exceptional versatility, with generous storage, a secondary laundry room, and access to the oversized garage—large enough to accommodate three vehicles. Two attics provide additional storage solutions.
Outdoors, a spacious deck with an electric awning overlooks the level, fenced-in backyard. The entire house is framed by mature trees, professional landscaping, and vibrant plantings. Additional amenities include a full-house generator, basketball hoop and an enviable location close to schools, train, shops, parks, and with direct access to the North County Trailway.
This turnkey Colonial combines classic sophistication, modern amenities, and a welcoming floor plan—perfectly suited for today’s lifestyle and ready to be cherished by its next owners.

$1,599,000 Pending

35 Whitlaw Lane Chappaqua, New York

4 Beds 4 Baths 3,732 SqFt 1.13 Acres

Move right into this sun-drenched, turnkey four-bedroom, four-bath home by Tom O’Brien Architecture, where classic design meets easy, comfortable living. Enter through cedar gates to a welcoming front portico with double columns and a barrel roof, setting the stage for what’s inside.The interior is bright and inviting, with newly refinished floors, custom millwork, recessed lighting, and oversized windows that fill the home with natural light. The layout flows beautifully from room to room, starting with a dramatic two-story foyer and continuing into a spacious living room with a slate fireplace and cozy bay-window seating. A formal dining room sits just off the main living space, making entertaining feel effortless.At the center of the home, the eat-in kitchen offers granite countertops, a built-in desk, and direct access to a flagstone patio—perfect for everyday living and casual gatherings. The adjoining family room features a vaulted ceiling and French doors that open to the backyard, creating a seamless indoor-outdoor feel.Upstairs, the primary suite is a peaceful retreat with custom closets and a spa-like marble bath. The finished lower level adds great flexibility with a playroom, office or guest space, full bath, laundry room, and a mudroom with direct entry to the attached two-car garage.Outside, the landscaped property is both private and inviting, with hydrangeas, mature plantings, and a nearby path leading to a quiet cul-de-sac. Conveniently located close to the school, with a bus stop right at the end of the driveway, this special Chappaqua home offers comfort, style, and a layout that truly works for today’s lifestyle.

$1,550,000 Pending

636 Quaker Road Chappaqua, New York

4 Beds 4 Baths 3,029 SqFt 0.6 Acres

Welcome home to this beautifully maintained, move-in ready classic Center Hall Colonial, perfectly tucked away on a peaceful cul-de-sac just moments from schools, shopping, and town conveniences. Enjoy direct on-street access to the North County Trailway — ideal for biking, walking, or running right from your neighborhood.Offering approximately 2,900+ square feet of comfortable living space, this inviting 4-bedroom home includes 2 full baths and a powder room. Thoughtful updates and timeless details are found throughout, including a new deck; hardwood, slate, and ceramic tile flooring, crown molding, and recessed lighting. A sun-filled Great Room with skylights — located just a half-flight up — provides a wonderful additional gathering space alongside the main-level Family Room.The warm and welcoming Family Room, complete with a wood-burning fireplace, flows seamlessly into the updated Eat-in Kitchen featuring cherry shaker-style cabinetry, granite countertops, stainless steel appliances, and a spacious breakfast area — perfect for everyday living and entertaining.The Formal Living Room and Dining Room provide gracious spaces for quiet enjoyment and large gatherings and flow easily to the more casual Family Room, Great Room, deck and yard.The bright and sunny second floor offers a Primary Bedroom with En-suite Full Bath, and three additional bedrooms and a hall bath.Additional highlights include main-level laundry, a 2-car garage, and a full basement with high ceilings and steel beam construction offering excellent finishing potential. Comfort is enhanced with a 3-zone HVAC system. Practical upgrades such as an above-ground oil tank, buried electrical lines, and a portable generator with battery backup provide added peace of mind.

$1,475,000 Active

9 Whitlaw Lane Chappaqua, New York

4 Beds 3 Baths 2,932 SqFt 1.05 Acres

Picturesque and spectacular center hall Colonial, beautifully situated on a cul de sac in the highly sought-after Dodge Farms neighborhood of Chappaqua. This sun-filled home blends suburban convenience with timeless warmth and character, offering generous-sized rooms and remarkable versatility throughout. The thoughtfully renovated chef's kitchen and baths complement a seamless flow ideal for both everyday living and indoor-outdoor entertaining. Featuring four bedrooms, two and a half baths, and a flexible main-level room perfect for a home office, playroom, or den. Additional highlights include a Tesla charger in the garage, walk-out basement, a robust walkable neighborhood setting, close to local amenities and an inviting layout designed for modern living.

$1,425,000 Active

110 Marcourt Drive Chappaqua, New York

4 Beds 3 Baths 2,921 SqFt 0.69 Acres

2 BR Primary on first floor home. Large Eat in kitchen with island, open to great room and dining room. Second floor office and wet bar makes entertaining easy on rooftop terrace with built-in kitchen BBQ. Lower level is finished with media room and full bath.

$1,399,995 Pending

13 Wallace Way 19 Chappaqua, New York

2 Beds 4 Baths 2,945 SqFt

Welcome to this beautifully maintained home featuring a spacious 476 sq ft sunroom with direct access from both the living room and family room—ideal for year-round enjoyment. Recent updates include new central air unit (2022) and all new water systems in the basement. The family room boasts a classic wood-burning fireplace, perfect for cozy evenings. Enjoy a formal dining room and an eat-in kitchen, great for everyday living and entertaining. A generous deck overlooks a large backyard, providing ample space for outdoor relaxation. Conveniently located near Metro-North and the towns of Chappaqua and Armonk, this home blends comfort, convenience, and charm.

$1,375,000 Pending

7 Byram Meadows Road Chappaqua, New York

4 Beds 3 Baths 2,891 SqFt 0.92 Acres

Classic Devoe Road colonial! A covered front portico welcomes you to this timeless traditional 3-bedroom, 2.5-bath colonial-style home. The spacious living room, anchored by a wood burning fireplace and lined with custom bookshelves enjoys radiant sunshine from the oversized true divided light picture window overlooking the front of the residence. The living room adjoins the formal dining room, lined with chair rail moldings and enhanced with crown and base moldings, gleaming hard wood floors and double French doors opening to a rear deck to make alfresco entertaining effortless. The gourmet eat-in kitchen is heartily equipped with a Bosch cooktop, double in-wall ovens and dishwasher, plus a Sub-Zero refrigerator, set along natural stone countertops and complemented by a built-in buffet with glass-front display cabinets, all topped with a tin ceiling. The inviting den features high ceilings, large picture windows, built-in display cases, a flagstone floor and a sliding glass door accessing the rear deck. A neat home office with loft supports work from home or sleep/study. A powder room is discreetly tucked in the entryway. A tidy mudroom with covered exterior entry and interior garage access finishes the main level. Upstairs reside three generously proportioned bedrooms and two full bathrooms, including a front-facing bedroom with ceiling fan and hardwood flooring, and a front-corner bedroom with two exposures, ceiling fan, and wall-to-wall carpeting with hardwood flooring beneath, both of which share a rear-corner bathroom endowed with both a bathtub and a separate shower stall. The opposite corner hosts the primary suite outfitted with a wall of closets and built-ins, including a cozy window bench and a private ensuite bath. The lower level provides lots of room for recreation and utility. A rear-facing divided light picture window brings natural light into two large adjoining recreation rooms with egress from a door to the flat rear yard. A laundry closet and a utility room with a bunker-like storage closet complete the lower level. This classic 1950s home has a flat easy driveway and rare, flat-as-a-pancake yards surrounded with lush and mature landscaping. A new roof was added in 2025, as was a new Roth above-ground oil tank. The neighborhood is one of the most sought-after locations in Chappaqua with close proximity to schools and access to a sidewalk to shops, town and train. A prime offering.

$1,336,000 Active

148 Devoe Road Chappaqua, New York

3 Beds 3 Baths 2,417 SqFt 1.001 Acres

Set on a quiet cul-de-sac, this charming 3-bedroom Cape, which could live like a 4-bedroom, offers the perfect blend of comfort, convenience, and style. The home has been impeccably maintained and thoughtfully renovated, with updates that make it truly move-in ready.
From the moment you arrive, the curb appeal stands out, enhanced by updated landscaping and a freshly painted exterior. Inside, natural light fills every room. The main level offers a primary bedroom and a flexible office/den, while upstairs provides spacious additional bedrooms and beautifully renovated full bath.
Enjoy entertaining or relaxing outdoors with a slate patio and a stunning pool, ideal for summer gatherings. A whole-house generator, newer roof, and central air provide ease of living, while the finished basement with full bathroom offers space for recreation, work, or guests.
Perfectly situated within walking distance to town, schools, shops, parks, and train, this home offers both privacy and community — a rare find in such a convenient location.

$1,299,500 Pending

36 Pond Hill Road Chappaqua, New York

3 Beds 4 Baths 2,866 SqFt 1.43 Acres

Experience timeless design and modern comfort in this stunning mid-century modern home, perfectly situated on 2.3 flat, open acres in the heart of Chappaqua. With three bedrooms, an office, and a spacious loft that lives like a four-bedroom, this property offers versatility and style for today’s lifestyle.Step inside and be captivated by walls of glass and abundant natural light framing breathtaking property views. The chef’s kitchen opens seamlessly to inviting living spaces, including a fireplace-warmed first-floor family room and a screened porch and deck for year-round enjoyment.The private primary suite features a wood-burning fireplace and serene outlooks, creating a true retreat. Upstairs, 2 more bedrooms, and office, a loft and additional family room offer flexible space for work, play, or relaxation.Enjoy outdoor living with a flat, usable yard, circular driveway, and tranquil setting on a quiet street, all just minutes from town and train. With 4-zone heating, hardwood floors, and classic mid-century lines, this home combines architectural character with modern livability.Discover the best of Chappaqua living—style, space, and serenity, all in one exceptional home.

$1,250,000 Pending

14 Valley Lane Chappaqua, New York

3 Beds 4 Baths 2,900 SqFt 2.3 Acres

Welcome to this sparkling sun-filled ranch, this beautifully updated 4 bedroom/2.1 bath home offers an easy living floorplan, lovely landscaped property and easy access to top rated schools, shops and commuter train. Over 2000 sq ft, on an acre, offering privacy amidst a neighborhood feel. Newly renovated bathrooms, updated kitchen, freshly painted interior, and gleaming newly refinished white oak floors throughout beckon. The many windows allow natural light to flow into an impeccably maintained interior in move-in condition. Enjoy morning coffee on the slate patio overlooking the landscaped backyard. The updated white kitchen features quartzite counters, glass tile backsplash, a peninsula and opens onto an appealing breakfast room. The Formal Living Room features a cozy fireplace, crown molding and wall of windows. The Formal Dining Room is gracious in size and offers a built-in corner cupboard and wall of windows. The King size primary bedroom has a newly renovated en-suite full bath, walk-in closet and door to the backyard. additional bedrooms offer flexibility for den, home office, playroom. There is a newly renovated hall bath and powder room. The main level laundry/mud room provides an easy transition from the 2 car garage into the living space and backyard. The finished basement with high ceilings and door out is ready to be finished as a playroom or additional living space. Many additional improvements such as a new roof, recessed LED lighting, updated electrical, combined with low taxes make this a compelling offering. Won't last, schedule your appointment to view today!

$1,199,900 Pending

111 Seven Bridges Road Chappaqua, New York

4 Beds 3 Baths 2,069 SqFt 1 Acres

Completely updated and remodeled residence in the heart of Chappaqua, offering a highly versatile layout ideal for in-law suite, professional office, and/or apartment use. The home features two bedrooms plus an office in the main residence, plus a private, 1-bedroom legal accessory apartment currently generating $2,500 per month in rental income. The property also offers the flexibility to live as a single-family home, as the dividing door between the main residence and accessory apartment can be easily removed, creating a seamless and naturally flowing one-family layout. Thoughtfully designed with two washer/dryer sets, radiant heat in select areas, and tray ceilings with custom lighting, the home blends modern upgrades with everyday comfort. Additional highlights include an oversized one-car garage, abundant off-street parking, and a Kohler whole-house generator for year-round peace of mind. Fully wired for multiple smart home and automation systems, the home is well-suited for today’s connected lifestyle. Ideally located just a short walk to Metro-North and within the award-winning Chappaqua School District, with easy access to shopping, dining, and commuter routes—this turnkey property offers exceptional flexibility, income potential, and an unbeatable location.

$1,150,000 Active

200 S Bedford Road Chappaqua, New York

3 Beds 3 Baths 2,364 SqFt 0.6 Acres

$1,149,000 Pending

35 Hamilton Road Chappaqua, New York

4 Beds 2 Baths 2,139 SqFt 1 Acres

Welcome to 29 Meadow Lane, ideally tucked away on a quiet, picturesque cul-de-sac in the heart of Chappaqua. Set on over half an acre of beautifully landscaped, private property, this fully updated ranch offers flexible living, modern comfort, and an exceptional location. Sidewalk-lined streets lead from the neighborhood into bucolic downtown Chappaqua, just minutes from shops, dining, and the Metro-North train. The property features a level, usable yard that offers the perfect balance of privacy and open green space for outdoor enjoyment. The sun-filled main level features a spacious living room, dining area, and updated kitchen with stainless steel appliances, flowing seamlessly into a three-season sunroom and out to an open deck perfect for relaxing or entertaining. Four bedrooms, including a primary suite with en-suite bath and a full hall bathroom, complete the main level. The lower level offers incredible versatility with an expansive family room with patio access, a den, half bath, laundry room, and a private office or guest bedroom, allowing the home to easily live as five bedrooms. Freshly painted throughout, major upgrades within the past four years include the kitchen, baths, recessed lighting, roof, HVAC system, and repaved Belgium block-lined driveway. The lower level and sunroom were renovated in 2026. An attached two-car garage completes this move-in-ready home. Sunday open house CANCELED due to weather.

$1,100,000 Pending

29 Meadow Lane Chappaqua, New York

4 Beds 3 Baths 2,445 SqFt 0.56 Acres

Set on 3.25 private acres of lush formal gardens and mature woodlands, this one-of-a-kind Chappaqua residence is a rare architectural treasure. Designed in the 1930s by renowned Westchester architect James Renwick Thomson, the home blends refined sophistication with warm, inviting charm—offering an unparalleled living experience just minutes from the heart of town. From Palladian windows and vaulted ceilings to Dutch doors, rough-hewn beams, copper gutters and exquisite custom woodwork, every detail speaks to the home's timeless character. Light floods the interiors through bay windows, while a second-floor terrace invites al fresco dining overlooking the serene landscape. Outdoors, the grounds are truly spectacular: meandering pebbled pathways wind through formal gardens with multiple sitting areas, two tranquil koi ponds, and a meandering stream. A red clay tennis court (easily restored) adds a resort-like touch, and the long, private driveway ensures a secluded retreat. Located within the award-winning Chappaqua School District and close to town, train, schools and swim and tennis clubs, this property offers both privacy and practicality. Commuting to NYC is a breeze—just a short drive or train ride away. Low taxes. DRIVEWAY ON TURNER DRIVE. Timeless Elegance Meets Tranquil Living - Don't miss this unique offering!

$1,099,000 Pending

124 Seven Bridges Road Chappaqua, New York

3 Beds 2 Baths 1,918 SqFt 3.25 Acres

Move right into this beautifully updated three bedroom, two bathroom ranch, perfectly situated within the award-winning Chappaqua school district. Thoughtfully renovated from top to bottom, this home offers modern comfort and timeless charm. The heart of the home is the stylish kitchen featuring classic oak cabinetry, sleek quartz countertops, and ample space for cooking and entertaining. Both bathrooms have been fully renovated with fresh, contemporary finishes. Enjoy cozy evenings by the fireplace in the spacious living room, and retreat to one of the generously sized bedrooms for quiet relaxation. Step outside to a flat, private yard—ideal for play, gardening, or hosting gatherings on the patio. This turn-key home offers the perfect blend of convenience, comfort, and location. Don’t miss this exceptional opportunity to live in a move-in ready home with top-tier schools and suburban tranquility.

$1,099,000 Pending

10 Barnes Lane Chappaqua, New York

3 Beds 2 Baths 1,776 SqFt 0.8 Acres

.Welcome to this unique and charming carriage home nestled in the heart of Chappaqua. Legally 2BR but lives as 3 BR with permitted additions. Bright and sunny, set on a private 0.69-acre lot. This well-maintained residence blends timeless character with modern updates. Step inside to a welcoming entry foyer that leads to a spacious living room, complete with a cozy fireplace and French doors opening to a secluded patio — perfect for entertaining or quiet relaxation. The country-sized kitchen has been thoughtfully updated, featuring an informal seating island and space for a full dining table, making it the true heart of the home. Off the kitchen, a lovely pergola extends your living space outdoors. The main floor offers a primary bedroom along with two additional versatile rooms — currently used as a family room and office but true bedrooms— plus an updated full bath and half bath . Upstairs, discover a loft-style master suite with its own private bath and French doors leading to a private balcony, creating a serene retreat. Additional highlights include parking for up to four cars, mature landscaping, and the privacy of a wooded setting, all while being minutes from Chappaqua’s schools, train station ( 1.2 miles), and town center.

$999,999 Pending

105 Douglas Road Chappaqua, New York

3 Beds 3 Baths 2,220 SqFt 0.69 Acres

Welcome to 23 Waters Edge, a delightful three-bedroom, two-and-a-half-bath home in the sought-after Old Farm Lake community in Chappaqua. This natural light-filled residence features an open floor plan with sliding doors that lead to a private patio—perfect for relaxed, easy living. Ideally located in the complex, this home enjoys privacy along with proximity to the community amenities.The open kitchen, dining, and living areas create a cozy yet modern atmosphere, ideal for both everyday living and entertaining. This level also offers excellent storage and a convenient powder room and access to the one car garage.Upstairs, you’ll find two well-proportioned bedrooms sharing a hall bath, along with a serene primary suite complete with a spacious walk-in closet and a beautifully renovated bathroom. Recent updates include windows, enhancing both comfort and efficiency, washer/dryer, dishwasher and AC condenser.Ideally located less than a mile from Chappaqua’s vibrant village and Metro-North train station, this home offers the perfect blend of privacy, convenience, and lifestyle. Welcome home.

$849,000 Pending

23 Waters Edge Chappaqua, New York

3 Beds 3 Baths 1,569 SqFt

$839,000 Active

11 Pondview Close Chappaqua, New York

3 Beds 3 Baths 1,648 SqFt 0.11 Acres

This classic center hall Colonial sits across the street, just steps from Gedney Park - one of the area’s most beloved parks, offering direct access to trails, fields, a playground, a sledding hill, a fishing pond, and year-round recreation. Inside, enjoy a sunlit living room with a wood-burning fireplace, French doors to a 3-season porch with new vinyl flooring, and refinished wood floors throughout. The renovated kitchen features quartz countertops, stainless-steel appliances, a tile backsplash, and direct access to the backyard deck. A traditional dining room and updated powder room complete the main level. Upstairs, there are three freshly painted bedrooms, all with new ceiling fans, and a full bath with access to a full attic. The basement includes laundry and ample storage. Notable upgrades include a new above-ground oil tank, all new lighting, and a freshly painted interior and exterior. This home location offers quick access to commuter routes, schools, and shopping. A great fit for buyers looking for charm, convenience, and community.

$778,000 Active

158 Millwood Road Chappaqua, New York

3 Beds 2 Baths 1,408 SqFt 0.3 Acres

$669,000 Pending

10 Grove Mews Chappaqua, New York

2 Beds 3 Baths 1,479 SqFt

Fantastic opportunity just steps from downtown Chappaqua. Only a short three minute walk to the heart of town, this property sits on a generous lot with great outdoor space and endless potential. Currently used as a single family home, the Business Retail zoning allows for a variety of uses whether you are an investor, looking for a live work setup, or considering a residential conversion. An unbeatable location close to shops, restaurants, and the Metro North. Bring your ideas and make it your own.

$649,000 Pending

221 N Greeley Avenue Chappaqua, New York

3 Beds 2 Baths 1,292 SqFt 0.335 Acres

$599,000 Active

150 Bedford Road 12A Chappaqua, New York

2 Beds 2 Baths 924 SqFt 0.001 Acres

Location, Location, Location! Chestnut Oak Complex. Dramatic and bright townhouse with natural lighting. This 1 bedroom 1.1 bath plus huge Loft/Den is in mint condition. Updated kitchen with stainless-steel appliances. Living room with high ceilings, fireplace and wall of windows is combined with spacious dining area. Updated powder room on the first level. Huge primary bedroom with with two clothes closets and private updated full bath. Loft/Den/Office off primary bedroom with sliding glass door to balcony. This unit comes with one-car garage, newer furnace, hot water heater, refrigerator. Washer and dryer in the unit. Entire interior of the unit was just painted (September 2025). Complex offers, pool, tennis and community garden. Conviently located to Chappaqua train station, shopping, schools, parkways and bus.

$475,000 Active

356 North Greeley Avenue Chappaqua, New York

1 Beds 2 Baths 1,207 SqFt 0.15 Acres

Chappaqua, N.Y.

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