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 on over 5 private, professionally landscaped acres in the exclusive cul-de-sac of Sutton Farm within Chappaqua’s esteemed Whippoorwill area, this custom-designed and custom-built Shingle Style home is a rare and refined first opportunity. Completed in 2008 by a renowned builder and architect, the 4+ bedroom home (lives like a 5/6) has been meticulously detailed with luxurious, high-end finishes that elevate every detail. A gracious covered front entry welcomes you to a dramatic two-story foyer with soaring ceilings, a sweeping curved staircase, and exquisite architectural detailing throughout. The shingle and stone facade exudes timeless curb appeal, while inside, craftsmanship and quality reign supreme. The thoughtfully designed open layout showcases wide-plank white oak floors and designer light fixtures from Holly Hunt, Visual Comfort, Jonathan Adler, and Boyd, imbuing each space with modern sophistication. At the heart of the home is a professionally appointed chef’s kitchen. A dual oven 6-burner range with grill by Wolf is accented by a custom-designed stainless steel hood. Built-in Subzero refrigeration features dual 36’ refrigerator freezers. Quartz and marble countertops, two dishwashers, and two sinks complete this exquisite space. Ideal for both entertaining and everyday living, the inviting breakfast area flows seamlessly into the sun-drenched family room with a custom masonry stone fireplace. The main level also includes a formal dining room with butler’s pantry, a gracious living room with a second masonry fireplace, a sunlit private office, and a well-equipped mudroom with back staircase. The second level includes a separate guest suite/bonus room and additional office space—ideal for multigenerational living or working from home. The luxurious primary suite offers a peaceful retreat with a tray ceiling, a dressing area, generous walk-in closets, and a spa-like bath. Three additional spacious bedrooms each feature en-suite baths. The finished walk-out lower level adds remarkable versatility with a large recreation room, game room, gym, full bath, guest/office suite, and abundant storage.The exterior grounds are truly an outdoor oasis: sweeping lawns, specimen trees, perennial gardens, and complete privacy. A newly paved Belgian block-lined driveway provides a grand entrance, while the expansive backyard features an oversized deck, perfect for entertaining, recreation, or serene relaxation. Additional highlights include a three-car, double-height garage, radiant heat, and whole-house generator—offering ultimate comfort, efficiency, and peace of mind. Located on once historic Sutton Farm, this one-of-a-kind home offers the best of both worlds: seclusion and serenity just minutes from Chappaqua, Armonk, schools, and train. Nature preserves are nearby for peaceful hikes. A rare and refined opportunity—perfection in every detail.

$3,499,000 Pending

5 Sutton Farm Drive Chappaqua, New York

4 Beds 7 Baths 7,708 SqFt 5.05 Acres

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

$2,299,000 Pending

22 Carriage Lane Chappaqua, New York

2 Beds 4 Baths 3,269 SqFt 0.08 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

Experience modern luxury and timeless sophistication in this stunning contemporary, beautifully sited on over an acre of park-like property in Chappaqua’s sought-after Whippoorwill neighborhood. Set on a quiet cul-de-sac with a majestic approach, this home is surrounded by mature trees and lush landscaping, creating a private oasis with level play areas and serene natural views backing to a protected nature preserve. This dramatic residence features soaring ceilings, expansive windows, gorgeous hardwood floors and sophisticated modern design throughout. A bold double-door entry opens to a sun-drenched foyer and gallery-like living spaces. The vaulted dining room with floor-to-ceiling windows flows seamlessly into an oversized living room with a fireplace and sliders to expansive wraparound decks—perfect for indoor/outdoor entertaining. The beautiful chef’s kitchen showcases stainless steel appliances, custom cabinetry, and a breakfast area with sliders for effortless alfresco dining. The main level also includes a spacious home office (or playroom) with a second fireplace, a guest bedroom/office, full bath, laundry area, and an attached two-car garage. Upstairs, the primary suite offers a fireplace, private balcony, dual walk-in closets, and an ensuite bath. Three additional bedrooms include one with an en-suite bath and two sharing a stylishly updated hall bath. The walk-out lower level provides great space for recreationa and storage. Offering a rare combination of architectural drama, flexible living space, and resort-like grounds, this exceptional home delivers the best of modern living in a peaceful Whippoorwill setting within the award-winning Chappaqua School District. AO 11/1/25

$1,999,000 Pending

73 Whippoorwill Lake Road Chappaqua, New York

5 Beds 5 Baths 3,849 SqFt 1.16 Acres

Modern Masterpiece! Soaring contemporary on a serene cul-de-sac, this 4-bedroom, 5216 sq ft home is defined by walls of glass and dramatic, oversized rooms. Set amidst rock outcroppings on 2.39 wooded acres with towering pines and babbling brook, this one-of-a-kind home in the acclaimed Chappaqua School District is situated in one of the most desirable neighborhoods offering both privacy and proximity. Welcome to your dream oasis, a stunning architectural-design home nested in a peaceful cul-de-sac neighborhood with a remotely controlled gated driveway. Gas and sewer, conveniently located near schools/shops, and express commuter train just minutes away. Curvilinear and geometric architectural elements uniquely define this house. This beautifully maintained property boasts an open-concept layout perfect for modern living and entertaining. The spacious living room that opens to a private deck enjoys ample natural light with walls of glass, cathedral ceiling, and a cozy fireplace, seamlessly connected to the dining and kitchen areas. The dining room provides dual access to decks. The chef’s kitchen features stainless steel appliances (new Sub Zero and Bosch), expansive countertops, a large center island, an adjacent breakfast area with dual access to decks, and plenty of cabinet space, making cooking a pleasure. The EIK opens directly onto a cathedral-ceiling family room with walls of glass, a raised hearth floor-to-ceiling stone fireplace, and built-in-bookcases. Gleaming hardwood floors and recessed lighting abound. A main-floor full bath with shower flows from an adjacent, separate laundry room with entry from the connected two-car garage. A dramatic, curvilinear staircase leads to the second level with wrap-around oak railings and breathtaking vistas of the private forest and brook in all seasons. Retreat to the primary bedroom suite that offers dual walk-in closets, an additional wall of closets, a separate windowed home office, a king-size bedroom, and an ensuite spa-style bath equipped with double sinks, a large storage vanity, a jetted tub, and a separate shower. Three more light-filled bedrooms and a hall bath complete the second floor. The gracious finished lower level provides nearly 1176 sq ft of included living space for play with a large recreation room and hobby area, a fully-stocked gym, as well as ample storage space and mechanicals. Step outside to a beautifully landscaped backyard, complete with five decks for dining al fresco or sitting privately in meditation, ideal for summer barbecues and gatherings. The property encompasses an extensive perennial garden teeming with pollinators every blooming season. Too many upgrades to mention include an electrified, remotely controlled, custom designed, galvanized wrought-iron driveway gate; digitized HVAC; generator; new roof (2017); newly painted decks and retaining walls; and resealed driveway. Impeccably maintained, in move-in condition. A one-of-a-kind architectural feat, a lifestyle of tranquility and privacy, a gem of a property that won’t last.

$1,995,000 Active

35 Neustadt Lane Chappaqua, New York

4 Beds 3 Baths 5,216 SqFt 2.39 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 Coming Soon

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

Stunning and elegant 5 bedroom/5.5 baths ranch style home plus detached garage Studio with full Bath and Kitchenette. Set back from the road with a fenced yard. Luxuriously appointed. Custom millwork featured in every room. Open floor plan, living room with marble floors, fireplace surrounded by built-in shelving with adjacent dining room with built-in cabinetry and buffet. Custom kitchen with oversized marble island, custom cabinetry and new appliances. Large eat-in area. Separate pantry /mudroom with abundant storage. Library with pocket french doors, and built-in book cases. Primary suite with a wall of custom cabinetry, walk-in closet, marble bath plus private balcony. Each bedroom features custom built-ins. Two additional ensuite bedrooms. Large family room with entertainment center and full bath. Sought after detached garage with beautifully appointed studio featuring large work area, kitchenette and a full bath with storage and built in cabinetry. Centrally located in Chappaqua, close to the train and all highways.

$1,725,000 Pending

675 Quaker Road Chappaqua, New York

5 Beds 6 Baths 4,616 SqFt 1.04 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

Welcome to this sophisticated 4-bedroom, 3.5-bath contemporary residence, perfectly designed for today’s lifestyle with a seamless blend of modern style and functional comfort. Set on a gracious property, this home offers open, luminous living spaces flooded with natural light and thoughtful architectural detail throughout. At the heart of the home, a beautifully appointed kitchen opens to a spacious family room—ideal for relaxed gatherings and everyday living. The formal living room is a true standout, featuring near wall-to-wall windows that frame the surrounding landscape and bathe the room in sunlight. A formal dining room provides a refined setting for entertaining, while the flowing layout ensures effortless movement between spaces. The coveted main-floor primary suite offers privacy and ease, with serene views and a spa-like en-suite bath. Upstairs, three additional bedrooms provide comfort and flexibility for guests, family, or work-from-home needs. Beyond the home’s design, the location truly shines—just minutes from town, Metro-North train service, top-rated local schools, and the convenience of Whole Foods Market. Whether you're commuting, shopping, dining, or enjoying the community, everything you need is close at hand. With expansive windows, sunlit interiors, multiple living and dining areas, and a prime layout designed for both entertaining and retreat, this home offers the best of contemporary living in a timeless and highly convenient setting.

$1,650,000 Pending

6 Whippoorwill Lake Road Chappaqua, New York

4 Beds 4 Baths 3,244 SqFt 1.47 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

Perfectly positioned on a serene and private 1.72 parcel in the sought-after, coveted Commodore Road neighborhood, this classic ranch-style home offers incredible potential just minutes from Chappaqua village, train, shops, and schools. Surrounded by mature trees, natural rock outcroppings, and a level backyard, this beautifully sited property with a majestic long driveway, is a rare find—offering both privacy and convenience. This meticulously maintained and solidly built home originally owned by its builder, offers an exceptional combination of privacy, natural beauty, and convenience to every amenity. This nearly 2,000 sq ft home with additional living area not included in the sq ft, provides the perfect structure for a forever home and your personal vision. The spacious first floor features a wide welcoming entry hall, leading to an oversized living room with a mantled fireplace and walls of windows bathing the room in natural light framing unforgettable woodland views. The formal dining room adjoins the kitchen and an enclosed 500 sq ft (not included in the home's sq ft) three season glass-enclosed screened porch with high soaring ceilings which brings the outdoors in and fills the home with natural light. The spacious deck is accessible from both the enclosed porch and kitchen which provides effortless modern indoor outdoor entertaining amid natural beauty. Gleaming hardwood floors found throughout the home, further enhance the home's space. Two steps up to the charming bedroom mezzanine which features three large bedrooms, including a primary suite with en-suite bath and two additional oversized bedrooms share a hall bath, offering flexibility for family, guests, or home office space. The lower level includes a large unfinished basement with a wonderful walk-out room (370 sq ft) with a wood burning fireplace, large picture windows and door out—ideal for a media room, playroom, gym, or home office. The utility room with a NEW Burnham boiler and hot water heater also has ample room for a modern laundry room. The basement also has a third large storage room with above-ground oil tanks and plenty of room for a workshop. The house enjoys radiant ceiling heat via copper piping. There is a walk-up attic in the home which offers more storage space and additional expansion opportunities. 2 car garage with two entry doors and separate attic storage. This home is an exceptional opportunity with endless possibilities in a prime Chappaqua location—not to be missed!!

$1,425,000 Pending

71 Commodore Road Chappaqua, New York

3 Beds 2 Baths 1,957 SqFt 1.72 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

Discover the perfect balance of modern design and peaceful living at 341 Millwood Road. Set on nearly 2 acres of wooded privacy within the Chappaqua School District, this completely renovated 4-bedroom, 2.5-bath Raised Ranch has been transformed from top to bottom. Every detail shines - from new flooring, doors, moldings, lighting, and baths to a stunning eat-in kitchen with GE Cafe WiFi-connected stainless-steel appliances, quartz counters, marble backsplash and a picture window overlooking the scenic backyard. The lower level features a custom mudroom, laundry center with new washer and dryer, family room with wood-burning fireplace, a large guest room , cedar closet and half bath. Outdoors, enjoy a turnaround driveway, new landscaping, a large deck, and a tiered yard ideal for a fire pit and playset. With new HVAC, above-ground oil tank, and full-house generator, this move-in-ready home blends modern luxury with timeless tranquility.

$1,375,000 Pending

341 Millwood Road Chappaqua, New York

4 Beds 3 Baths 2,541 SqFt 1.93 Acres

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

Chappaqua Schools! This immaculately maintained 3-bedroom stone and shingle Colonial is gracefully sited on nearly an acre of professionally landscaped grounds, offering exceptional privacy and tranquility.

A charming stone portico welcomes you at the front entry, setting the tone for the elegant interiors that follow. Sun-drenched spaces and an open-concept layout create an inviting and seamless flow throughout. The spacious first-floor primary suite features doors leading to a large, private deck—perfect for morning coffee or evening relaxation.

The beautifully renovated kitchen boasts stainless steel appliances, a center island, and breakfast bar, opening to a light-filled dining area and an all-season sunroom with direct access to the deck. The dramatic living room impresses with soaring ceilings, a striking stone fireplace, and ample space for a grand piano—truly a showstopper. Ideal for effortless entertaining.

Upstairs, a generous sitting area offers flexible use as a home office, playroom, or media space, along with two well-appointed bedrooms and a stylish hall bath with double vanity and stall shower.

The expansive, full unfinished basement provides endless possibilities for additional living space, gym, or recreation room.

A rare opportunity to enjoy refined living in a peaceful setting—minutes to town, train, and award-winning Chappaqua schools.

$1,300,000 Pending

100 Old Farm Road N Chappaqua, New York

3 Beds 3 Baths 2,971 SqFt 0.9 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 Active

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

Please Note: Best and final offers due by Tuesday, 1/20 at 5PM. This charming 1915 traditional home welcomes you with generous living spaces, rich in character, and thoughtful updates designed for comfortable everyday living and special gatherings alike. This home opens to a spacious patio perfect for relaxation and entertaining. The seasonal Carriage Barn adds a touch of magic offering a wonderful space for play, hobbies, a cozy art or work studio. Set on one beautifully landscaped acre, this lovingly maintained home is ideally located just minutes from town, the train, schools and all of the conveniences that make daily life easy and enjoyable.

$1,149,000 Active

35 Hamilton Road Chappaqua, New York

4 Beds 2 Baths 2,139 SqFt 1 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 Active

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 Active

105 Douglas Road Chappaqua, New York

3 Beds 3 Baths 2,220 SqFt 0.69 Acres

$839,000 Active

11 Pondview Close Chappaqua, New York

3 Beds 3 Baths 1,648 SqFt 0.11 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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