Chappaqua NY Real Estate & Homes for Sale

Exceptional and turnkey, this sun-filled 3 (could live like a 4) -bedroom home, nestled on nearly an acre of completely level, private property in the coveted Algonquin neighborhood in the Chappaqua School District, is exactly what you've been waiting for! The expansive sun drenched first floor features an expansive chef's gourmet kitchen open to an oversized family/great room. The spectacular kitchen boasts top-of-the-line stainless appliances, a huge center island with counter seating, a large eating area with a door to the patio and the tranquil backyard, creating a picturesque setting for meals, several counter prep areas, a desk area, and a door the mudroom/garage. The large inviting family room with walls of windows and vaulted ceiling is perfect for entertaining and comfortable living. The first floor also features an expansive dining room with a fireplace, an office, full bath and a cozy living room. The second floor has an expansive, serene primary bedroom suite with beautiful views, two walk-in closets, and a spa-like ensuite bathroom with tub, oversized shower, double sinks and a toilet room. Two charming well-proportioned bedrooms with in-wall custom dressers, window seats, closets and delightful finishes, and a hall bathroom with tub/shower and two sinks complete this level. Meticulously maintained and tastefully updated, with freshly painted interiors, whole house generator, Nest and more! Private completely level property offers wonderful space for entertaining and enjoyment. This home is one of Chappaqua's finest!

At the end of a beautiful Chappaqua cul de sac street behind gates sits this picturesque estate nestled in lush surroundings, boasting intricate millwork and timeless elegance.Its architecture seamlessly blends classic charm with modern comforts, flooded with natural light and adorned with exquisite detail. As you step outside, you're greeted by a custom pool and spa surrounded by manicured gardens, offering a perfect retreat for relaxation, fun and leisure. This privately set home has 4 bedrooms (lives like 6), spacious living areas, gym, plus office with a first floor primary suite, as well as a 3 car garage in one of Chappaqua's most coveted neighborhoods. A stunning and sophisticated family home showcasing timeless elegance is perched on nearly 2 acres of beautifully landscaped grounds with spectacular views of Turkey Mountain. Thoughtfully executed three finished levels with chic and designer finishes, this rare Northern Westchester retreat is an opportunity for only the most discerning buyer.

Spectacular custom designed contemporary is located in a coveted Whippoorwill neighborhood in the heart of Chappaqua! This dramatic 5 bdrm home (lives like a 6) is sited on over 2 level acres with soaring cathedral ceilings and expanses of glass infusing the home with natural light & tranquil views from every room. Thoughtfully renovated and upgraded over the years. The Gourmet Eat-in Kitchen is a chef's delight with top of the line stainless steel appliances, granite countertops and a fireplace opening to a grand family room with soaring ceilings and walls of windows. A formal living room, dining room, sunroom, powder room and first floor bedroom (currently used as an office) with en suite bath and mudroom complete the first floor. Primary bedroom suite on its own level boasts an oversized luxurious spa bathroom, the perfect retreat! A few steps up lead to 3 additional large bedrooms, 2 full baths, one en suite and all with large walk in closets . The finished walkout lower level includes a recreation room with full bath, summer kitchen and bonus room, perfect for a home office, gym or guest room! Relax on the oversized deck and enjoy the exquisite park-like property with lush lawns and your own pool!! Only minutes to town, schools, parks, train and Whole Foods + Lifetime Fitness at Chappaqua Crossing. A special home not to be missed!

2 BR Byram Farmhouse This is the model home which includes an array of upgrades, you can close on this home in June 2024 and lease back until December 2024 at the latest. Home includes a finished basement with half bath and may more upgrades. The open concept great room and kitchen allow for large family gatherings. The open island with ample seating beckons your inner chief to come alive. A roaring fireplace will warm the entire home. A private rooftop terrace with included outdoor kitchen, 2- car garage and the highest quality interior appointments you've come to expect from Toll Brothers round out this spectacular residence! 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, pool opening Summer 2025, clubhouse which will open this Fall, and much more!

Mid-century modern home lovers will appreciate this 1979 contemporary, designed by Chappaqua architect, Charles Napoli as an homage to Frank Lloyd Wright. Set on 1.35 acres, this 5 BR, 5.1 BA home has walls of windows showcasing the lush property and mature trees. The open plan of the house flows naturally with a grand, open living rm to dining and eat-in kitchen w/ sliders to patio. The great room leads down to the den and additional lower level. A playroom with custom built-ins, guest suite w/ bathroom, gym w/ door to garage and plentiful storage, complete this level . The 2nd floor includes a large primary suite w/ office, dressing area, walk-in closet and beautifully updated bathroom. There are 3 more generously sized bedrooms and 2 bathrooms plus a sitting room. Outside, enjoy a large patio overlooking the terraced gardens and private backyard adjacent to over 20+ acres of town-owned land.

Come experience not only an extraordinarily designed residence, additionally enjoy a home set atop quite possibly one of the highest viewpoints in Chappaqua. Commissioned by the Mechner family in 1969, architect John Koster worked closely with present owners to develop a property like no other. Sited on 8.86 wooded acres with vintage log cabin and sculptural stone outcroppings inspired a multifaceted built home which now offers an incredible opportunity to renew an envisioned masterpiece. An architectural smooth curved arc ceiling immediately excites the senses and draws you into an inviting, flowing living space complimented by a bank of windows arranged to capture the surrounding dynamic landscape. Juxtaposed to this stunning view is a rising wall of glass looking into a one-of-a-kind resplendent domed indoor pool oasis anchoring the home and presenting an exceptionally private retreat. The original open living concept is immediately present with the kitchen, awaiting its reawakening, flowing with ease to a generous gathering room with deck for memorable family and friends indoor-outdoor entertaining. The upstairs of the two-level bedroom wing incorporates a primary bedroom suite with dressing room, its own office and a plumbed bath waiting a new owner's vision. Additionally, there are two bedrooms which share a bath. Stepping into the lower level, with open living space for media and play, smartly complimenting the additional bedrooms and baths. Design. Structure. Nature. Let one's creative spirit soar

Welcome to 5 Longview Lane, a thoughtfully updated, sun-filled home on a level acre in Chappaqua. This 4-bedroom, 3-bath home offers flexible living spaces, making it ideal for the modern buyer. Upon entry, you'll be captivated by the grand two-story entry and staircase, creating the perfect introduction to the light and airy rooms. The elevated main floor, features living spaces and 3 bedrooms, including the primary suite, providing convenience and privacy. An open flow connects the living room to the dining room and kitchen, creating the perfect space for relaxing and entertaining. Enter the sunroom with its private views and sliding doors that lead to the spacious Azec deck, revealing a serene landscape of the secluded backyard featuring custom stonework and a blue stone patio. The entry level presents a spacious family room with a floor-to-ceiling fireplace, picture window, fourth bedroom, full bath, and laundry room. This home offers a usable flat yard, creating a safe and inviting environment for outdoor activities. Ample storage in garage, attic, under deck and shed. Two car garage, plus multiple parking spaces in driveway. School bus stop in front of house. Easy commute via Chappaqua Metro North station and quick access to major highways. Enjoy the award-winning schools, weekend farmers market, shops and the new Whole Foods complex at Chappaqua Crossing just minutes away. Recent updates include: windows, hall bath, Azec deck, landscape lighting, stone wall, AC units, interior and exterior paint and more. Showings begin 5/1.

Each elegant detail has been thoughtfully designed in this gracious four bedroom center hall colonial expanded and renovated in 2012. Beautifully sited on a quiet cul de sac street with close proximity to town, train and schools, this home has a lovely park-like backyard and spacious two level deck overlooking the entire picturesque and serene property. The front foyer opens to a formal living room spanning front to back with windows on both ends and fireplace with slate surround on one side and dining room on the other. The light and very bright renovated kitchen includes breakfast bar seating, custom cabinetry, high end stainless steel appliance and honed jet mist granite countertops. The kitchen opens to a sensational family room enhanced by soaring ceilings, raised bluestone hearth fireplace and sliders to deck. The first floor office with door and 12 windows around the perimeter is the ultimate private retreat. The second floor boasts an impressive primary suite with two custom designed walk in closets and luxurious en suite full bath with deep soaking whirlpool bathtub, honed marble floor and honed marble topped double vanity with storage and oversized steam shower. Three bedrooms, one with an en suite full bath and hallway full bathroom complete the 2nd level. Additionally, the home has white oak flooring, a whole house generator, Thermopane windows and crown molding. The 666 sq foot finished lower level (included in total) has garage access, mudroom with laundry and a large recreation area. The impeccable high end renovations will surely impress the most discerning buyer.

Welcome to the original Royal Barry Will's designed Cape. Enter into the most charming, cozy and relaxing sanctuary home Chappaqua has to offer. The main floor features, living room, den, sun filled kitchen with patio, mudroom, private primary suite with full bathroom and powder room. The second floor has 2 bedrooms, bathroom and office. Just minutes away from Seven Bridges swim club, shops, dining, metro north train station and award-winning school district.

NOTED ARCHITECT DAVID HENKEN DESIGNED THIS HOME in 1957 EMBRACING THE UNION OF LANDSCAPE & ARCHITECTURE. Nested atop a private zen-like oasis you immediately understand Henken's genius of using the natural topography while conceptualizing the modernist lifestyle. Architectural design inclusive of cantilevered rooms, mitered corner glass, and indoor-outdoor flow all take advantage of the surrounding lush landscape of boulder outcroppings, views and a very special organic pool setting. This treasured home, meticulously updated by the current owners, kept exciting original elements including the loft like open space, entertaining areas and even a workshop-office. Mahogany finishes, along with exceptional masonry work add warmth while walls of glass enrich the soul. Bonus property across Laurel Lane gains access to the Laurel Lane pond. WELCOME HOME.

Presenting this meticulously maintained bi-level home, curated with luxury in mind. Enjoy comfort and sophistication with red oak hardwood flooring, recent upgrades like a new roof, boiler, and sanitary system. With 4 bedrooms and 2 baths, there's ample space for the whole family. Entertain effortlessly with three freshly stained multi-level decks, perfect for gatherings. Large yard, with three sheds, offers plenty of outdoor storage and enjoyment. Nestled in Chappaqua P.O. within the prestigious Pleasantville School system, enjoy convenience with Rare FREE SCHOOL BUS PICK UP in a walking school district of Pleasantville!!! on this tranquil cul-de-sac location. A short 5-minute walk to the Chappaqua Train station just 45 minutes to Grand Central Station. Park-like grounds, fostering freedom and adventure. Inside, cathedral ceilings and Red Oak hardwood floors elegance, comfort and style in a coveted Chappaqua location, minutes to Farmers market shops train and restaurants.

HOME NOT COMPLETED YET- 3 BR Millwood Elite home. This outstanding home is located in the heart of the neighborhood where you can walk to shopping, cafe, gym, pool and more. Includes 3 BR + 2 offices, loft and outdoor terrace w built in grill and linear fireplace and interior wet bar in loft. The open concept great room and kitchen allow for large family gatherings. The open island with ample seating beckons your inner chief to come alive. A roaring fireplace will warm the entire home. A private rooftop terrace, 2- car garage and the highest quality interior appointments you've come to expect from Toll Brothers round out this spectacular residence! 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, pool, clubhouse, and much more!

HOME IS UNDER CONSTRUCTION!! 2 BR Briarcliff Floorplan with primary on first floor plus finished basement with half bath. This outstanding home is located in the heart of the neighborhood where you can walk to shopping, cafe, gym and more. It is ideally sized at 2,945 sq. ft. and includes 2 BR + office, loft giving you plenty of space for your entire family to enjoy. The open concept 2 story great room and kitchen allow for large family gatherings. The open island with ample seating beckons your inner chief to come alive. A finished basement and powder room give the homeowners more room to enjoy. A roaring fireplace will warm the entire home. A private rooftop terrace, 2- car garage and the highest quality interior appointments you've come to expect from Toll Brothers round out this spectacular residence! 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, pool, clubhouse, and much more! Still time to select your design features. MOVE IN FALL 2024

HOME IS TO BE BUILT. 2 BR very popular Greeley Floorplan with primary on first floor. We have a model of this home to walk through. It is ideally sized at 3,269 sq. ft. and includes 2 BR + office, huge loft, finished basement with media room and full bath. The 2-story open concept great room and kitchen allow for large family gatherings. The open island with ample seating beckons your inner chief to come alive. A private rooftop terrace with outdoor kitchen and grill, 2- car garage and the highest quality interior appointments you've come to expect from Toll Brothers! 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, pool, clubhouse, and much more! Still time to add your own personal touches in both structural and design.

HOME NOT COMPLETED YET- NEW CONSTRUCTION HOME FOR SALE!! 2 BR Byram Farmhouse under construction. Byram model home available to tour. This home can close in Spring 2025. Home includes a finished basement with full bath, media room and may more upgrades. The open concept great room and kitchen allow for large family gatherings. The open island with ample seating beckons your inner chief to come alive. A roaring fireplace will warm the entire home. A private rooftop terrace with included outdoor kitchen, 2- car garage and the highest quality interior appointments you've come to expect from Toll Brothers round out this spectacular residence! 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, pool, clubhouse, and much more!

Welcome to 70 Cowdin Lane! Nestled at the end of a highly sought after private lane in the idyllic town of Chappaqua, this stunning 4-bedroom, 4-bath modern barn-style house is not to be missed! Situated on 2.3 beautiful acres, the residence offers a perfect blend of seclusion and convenience, mere moments from shopping, dining, the train station, and schools. Step through the double front doors into the two story foyer to discover a sun drenched sunken living room with a floor to ceiling stone fireplace along with a wall of french doors with transom windows and newly refinished wide plank white pine floors. The adjacent dining room has plenty of space to host holidays or enjoy long weekend brunches. Continue into the newly renovated chefs kitchen to find the heart of the home. The kitchen boasts all high end appliances including double Wolf ovens , Wolf refrigerator, microwave drawer and double Bosch dishwashers. The open concept kitchen flows seamlessly into the family room complete with a fireplace and vaulted ceilings. Off of the family room you will find a powder room, mudroom, pantry and access to the two car garage. Follow the stairs up into two rooms perfect for a home office, playroom, and/or gym. Step outside onto the beautiful screened-in sun porch made for warm summer nights or chilly fall days. On the second floor you will find the privately situated primary suite with a newly renovated bathroom with heated floors, large shower and a soaking jacuzzi tub. The second floor also has a library/den with a classic sliding barn door and two more bedrooms with extra large closets, one with a loft space perfect for a desk or extra play area. The newly renovated bathroom has a separate vanity. The laundry room is also on the second floor situated for convenience. The lower level recreation room has ample space for a home gym and plenty of space for entertaining. You will also find the state of the art 12 seat theater and a custom designed wine cellar. Beyond its exquisite design and premier location this home represents the epitome of contemporary country living, where every detail has been meticulously curated for the discerning homeowner. Reach out to schedule a private showing!

Indulge in the ultimate luxury living experience in this exquisite dream home, nestled within a private 4-acre botanical garden. This exceptional property is designed for entertainment and outdoor living, featuring resort-like amenities including an inground gunite pool with a spa, a hard-court tennis/pickleball/basketball court, and a personal 140+ yard par 3 golf hole complete with bunkers and multiple tee boxes for various shot perspectives. A country club experience, without leaving home. Step into luxury as you enter the main residence, spanning over 6,000 square feet across three levels, with 5 bedrooms, 4 full bathrooms, and a powder room. The first floor sets the stage for indoor entertainment with a massive, sun-filled great room, a large formal dining room, and a den set off the eat-in, chef's kitchen. The massive deck running the full length of the house seamlessly blends indoor and outdoor living, connecting you from the first level to the pool area down below. The finished lower level features a nice recreation area, an au Pair Suite with a full bath & shower, and is highlighted by a 4500-bottle wine cellar. The property also boasts a remarkable 1362-square-foot freestanding office, perfect for those who desire a dedicated workspace separate from the main house, above the detached 3-car garage. A perfect space for an office/game room/guest suite, equipped with a summer kitchen and full bath - ideal for work, play, entertaining, or hosting guests. A whole house generator ensures uninterrupted power supply, and every corner of this sanctuary exudes thoughtful sophistication, from the manicured grounds to the breathtaking vistas. This unparalleled estate offers a harmonious blend of work and leisure, making it truly one of a kind. Approx. FULL square footage = 7,388 including Studio above the garage Main House = 6,026sf Studio above Garage = 1,362sf

Incredible opportunity in Chappaqua for a refreshing new build with the convenience of in-town living, where you can walk to town and train. This state of the art offering is under construction by esteemed builder Steven Tavolacci of Tavo Development, collaborating with highly regarded architect Teo Siguenza. A serene setting, overlooking Duck Pond, offers open concept living with highlights that include a pass-through fireplace between the Living Room and Family Room, an office/library with access to the screened porch and large gourmet Kitchen with Dining Area. The second floor provides a private spacious primary suite with a sitting room, dressing room and a large bath. Two additional ensuite bedrooms, laundry and bonus room complete this level. The finished lower level offers additional space for recreational enjoyment. This three bedroom home, which lives like a four bedroom, has a projected hookup to sewer within the year. Minutes to Chappaqua, highways and a 50-minute drive to NYC. Convenient to all. Projected completion date is Aug-Sept 2024. Be in for the new school year!

Wonderful Westchester estate on almost 6 beautiful acres. Supremely private, the property is gated and accessed by a winding and circular drive. The homesite is elevated and open-a perfect blend of rolling lawn, curated gardens and towering trees. The house, comprising five bedrooms and five full baths, combines traditional colonial architecture with modern elements. Floor to ceiling Palladian windows flood the living and family rooms with natural light. Triple French doors access a handsome brick terrace, A large open kitchen centers on an island and is adjacent to a lovely screen porch. The tennis and pool complexes are separate from the house and include a newly renovated cabana and an oversized saltwater pool. Located one mile from town and train, the house and property offer all the amenities of a cherished vacation destination with the convenience of village life. A very special offering within The Chappaqua School District.

Welcome to an architectural masterpiece on coveted Algonquin Drive. This custom home is perfect for the discerning buyer who wants sophisticated, luxury living. Walls of glass and French doors flood the home with light. Enjoy custom millwork, double-height foyer, 10' ceilings, and oak floors. The Deane kitchen is the home's heart, with a large island, brick fireplace, stainless appliances, and gracious eating area. A 20' high stone fireplace anchors the adjoining family room. Multiple mahogany decks and sunporch indulge indoor/outdoor living or entertaining. Flex rooms can be home offices, nanny room, or gym. Upstairs, the primary suite boasts soaring ceilings, deck, fireplace, and sitting area. Four more bedrooms have bespoke features, including vaulted ceilings and ensuite bathrooms. The upstairs gathering area and bonus room can be used for study, work and play. Outside, enjoy privacy with flowering trees, flagstone patio, hot tub, a potential pool site. Elevator/Generator. Moments to town, train, schools.

Unique opportunity to own this convenient, in town, multi-use, four-floor building, zoned BR for business and residential use. The current configuration is a 3-story residential unit with a legal accessory apartment and 2 attached income producing retail/office spaces. A two-car attached garage and plenty of space in the rear provides ample parking. Town sewer hookup is accessible from street. Possibly the perfect mother-daughter home. Located within walking distance to downtown Chappaqua, close to town, trains and shopping. 50 minutes to NYC.

A magnificent, move-in-ready modern classic that feels grand yet warm, welcoming and young. With Ritz-Carlton-caliber luxury details throughout, this newly-constructed Jeff Taylor-designed compound is sited on 7.29 private acres in the acclaimed Chappaqua school district. Its ideal location is minutes from Bedford, the Saw Mill River Parkway and MetroNorth to NYC. Each space is a sanctuary of serenity, taste and quality, epitomized by 10-foot coffered ceilings, paneled walls, mahogany doors and oak floors. The grandeur of the residence extends to five ensuite bedrooms and four additional half baths boasting Carrera marble and Dornbracht fixtures. The residence optimizes flexibility, offering multiple offices and family rooms, a Peloton workout space, billiards/games room, and even a lushly appointed garage-lounge for 3 cars. A culinary haven awaits in the Top Chef-worthy kitchen, adorned with luxe Leicht cabinetry and top-of-the-line Miele and Wolf appliances. Smart lighting, radiant heat, Sonos sound inside and out, and a full camera security system seamlessly integrate modern technology with the timeless charm of the home. French doors beckon to the stunning bluestone terrace, lush level lawns, and specimen plantings. A heated LED-lit swimming pool and Grand Effects fire bowls create an enchanting ambiance for resort-style entertaining day and night. A separate Greek Revival-style guesthouse/office is accessed by an elegant, sun-drenched breezeway: a lovely walk on a radiant heat. This Chappaqua masterpiece is a testament to modern luxe living that transcends time. An historic, walkable town, exceptional schools, multiple country and swim clubs, chic boutiques and renowned restaurants like the 200-year-old Crabtree's Kittle House, with its acclaimed farm-to-table cuisine. A truly unique opportunity.

This stunning sun-drenched contemporary home offers the perfect blend of style, comfort and seamless connection to the outdoors. Situated on one of Chappaqua's most sought-after streets, this 4-bed 4-bath home boasts unique design elements and a host of impressive features. The primary bedroom is an oasis with sliders to the outside, a balcony overlooking the yard, a separate changing area, 2 walk-in closets and large bathroom with copper soaking tub. Two spacious home offices provide a perfect environment for hybrid work. Enjoy large south-facing picture windows and high ceilings in this entertainer's delight featuring two fireplaces, 9-zone Sonos sound system, open concept and easy flow inside and out. The recently updated gunite pool is surrounded by impressive stonework, beautiful plantings and built-in propane grill. Multiple balconies and patios overlook this picturesque, level fenced-in yard filled with specimen trees and perennials, complete with swingset and playhouse.

Recently renovated in 2023, this Split level home with large living room, dining area, gorgeous kitchen with access to patio and back yard. 3 bedrooms and 3 full bathrooms. Finished lower level. Lots of storage and access to an unfinished crawl space. Private lot located in great location to shops, major parkway, and schools. Fully renovated home with nothing to do but move in and add your personal touches. Call today!

BACK ON THE MARKET! Set on a sprawling 4.11-acre parcel in the esteemed Chappaqua enclave, 20 Bessel Lane offers an unparalleled blend of sophisticated living and natural tranquility. Every aspect of this residence and its grounds has been thoughtfully curated to fuse the home's refined design with the property's lush surroundings. The residence, boasting an expansive 7,978 sqft of living space, is designed with attention to detail and functionality. Expansive windows throughout the home frame views of the meticulously landscaped grounds, ensuring a continual connection to nature. Comprising 6 generously proportioned bedrooms and 5.5 bathrooms, this home meets both luxury and daily living needs with finesse. The dedicated home office and a bespoke home gym are significant additions, recognizing contemporary lifestyle requisites. Outdoors, the Shoreline pool is the centerpiece, designed to harmonize with the property's lush backdrop. Adjacent to the pool, a fully-equipped cabana with a kitchen is perfect for effortless entertaining. Tennis aficionados will find the private court, nestled among mature trees and rock formations, an exceptional addition. A unique feature of this estate is its dedicated orchard and vegetable garden area-a nod to sustainable living and a source of organic produce right in your backyard. Comprehensive amenities like a full irrigation system and thoughtful outdoor lighting ensure the grounds remain both functional and picturesque. Chappaqua's reputation for distinguished schools and a vibrant, tight-knit community make it a coveted location. Further enhancing this property's appeal is its proximity to New York City-just a 45-minute train journey, ensuring urban amenities are within easy reach.