2,842 houses for sale in Chappaqua

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

Welcome to 24 Half Mile Road, a beautiful and renovated turn-key ready three-bedroom home located in sought-after Armonk. This impeccably well-maintained Mid-Century Modern property leaves nothing to be desired - move in and unpack! Enjoy care free Ranch-style single floor living - all three bedrooms including primary on main floor, with full lower level with endless potential for recreation, entertainment and storage. Soaring vaulted ceiling in the living room with tongue-and-groove pitches. Spacious, light and bright renovated chef's kitchen with adjacent dining area - perfect for entertaining. Primary bedroom has en-suite primary bathroom with walk-in closet and expanded storage. Custom outfitted closets. Unwind after a long day at one of three fireplaces, cozied up with a book or tablet! Enjoy nature from your deck, easily accessed from three separate rooms. Spray foam insulation in lower level. Humidifier added to heating system in lower level. All interior and exterior lighting r

Welcome to 24 Half Mile Road, a beautiful and renovated turn-key ready three-bedroom home located in sought-after Armonk. This impeccably well-maintained Mid-Century Modern property leaves nothing to be desired - move in and unpack! Enjoy care free Ranch-style single floor living - all three bedrooms including primary on main floor, with full lower level with endless potential for recreation, entertainment and storage. Soaring vaulted ceiling in the living room with tongue-and-groove pitches. Spacious, light and bright renovated chef's kitchen with adjacent dining area - perfect for entertaining. Primary bedroom has en-suite primary bathroom with walk-in closet and expanded storage. Custom outfitted closets. Unwind after a long day at one of three fireplaces, cozied up with a book or tablet! Enjoy nature from your deck, easily accessed from three separate rooms. Spray foam insulation in lower level. Humidifier added to heating system in lower level. All interior and exterior lighting r

An incredible opportunity to enjoy life on spectacular, private and very desirable North Lake in the highly sought-after Windmill Farm community. Complete with your own waterfront dock, this home offers swimming, boating, fishing and effortless indoor-outdoor entertaining in a truly serene setting.This gorgeous 4-bedroom home features an open floor plan, a beautiful updated kitchen, two spacious family rooms, and hardwood floors throughout. Recent improvements include a new roof and new exterior siding, among many other thoughtful updates. North Lake is truly something you have to experience in personphotos dont do it justice. The setting evokes the feeling of the Adirondacks, yet its located within the award-winning Byram Hills School District. The home also offers MEC membership eligibility, providing access not only to your private lake lifestyle, but also the amenities of the Windmill Club.Easy commute to Manhattan via 40-minute express train from North White Plains into GranRefere

An incredible opportunity to enjoy life on spectacular, private and very desirable North Lake in the highly sought-after Windmill Farm community. Complete with your own waterfront dock, this home offers swimming, boating, fishing and effortless indoor-outdoor entertaining in a truly serene setting.This gorgeous 4-bedroom home features an open floor plan, a beautiful updated kitchen, two spacious family rooms, and hardwood floors throughout. Recent improvements include a new roof and new exterior siding, among many other thoughtful updates. North Lake is truly something you have to experience in personphotos dont do it justice. The setting evokes the feeling of the Adirondacks, yet its located within the award-winning Byram Hills School District. The home also offers MEC membership eligibility, providing access not only to your private lake lifestyle, but also the amenities of the Windmill Club.Easy commute to Manhattan via 40-minute express train from North White Plains into GranRefere

An incredible opportunity to enjoy life on spectacular, private and very desirable North Lake in the highly sought-after Windmill Farm community. Complete with your own waterfront dock, this home offers swimming, boating, fishing and effortless indoor-outdoor entertaining in a truly serene setting.This gorgeous 4-bedroom home features an open floor plan, a beautiful updated kitchen, two spacious family rooms, and hardwood floors throughout. Recent improvements include a new roof and new exterior siding, among many other thoughtful updates. North Lake is truly something you have to experience in personphotos dont do it justice. The setting evokes the feeling of the Adirondacks, yet its located within the award-winning Byram Hills School District. The home also offers MEC membership eligibility, providing access not only to your private lake lifestyle, but also the amenities of the Windmill Club.Easy commute to Manhattan via 40-minute express train from North White Plains into GranRefere

Welcome to 24 Half Mile Road, a beautiful and renovated turn-key ready three-bedroom home located in sought-after Armonk. This impeccably well-maintained Mid-Century Modern property leaves nothing to be desired - move in and unpack! Enjoy care free Ranch-style single floor living - all three bedrooms including primary on main floor, with full lower level with endless potential for recreation, entertainment and storage. Soaring vaulted ceiling in the living room with tongue-and-groove pitches. Spacious, light and bright renovated chef's kitchen with adjacent dining area - perfect for entertaining. Primary bedroom has en-suite primary bathroom with walk-in closet and expanded storage. Custom outfitted closets. Unwind after a long day at one of three fireplaces, cozied up with a book or tablet! Enjoy nature from your deck, easily accessed from three separate rooms. Spray foam insulation in lower level. Humidifier added to heating system in lower level. All interior and exterior lighting r

Charming on the outside but updated and modern on the inside! Spacious living room has large bay window and also boasts a fireplace for those cold winter nights. Through the oversized doorway is the dining room which is large enough to host friends and family for both informal occasions and the holidays. The updated kitchen (2024) with heated flooring will make any chef happy. From the kitchen you can access the idyllic back yard. Recently fenced in and landscaped. Beautiful original hardwood flooring throughout. Upstairs you will find three bedrooms and updated hall bath with dual sinks and heated flooring. Stairs up to large usuable attic. Full unfinished basement will solve all your storage needs. Central air and a detached two car garage are the finishing touches for this great home! Minutes to Metro North which gets you into Grand Central Station in under an hour, close to highways, shopping and downtown Ossining. A perfect blend of privacy and a prime location

Welcome to this charming four-bedroom, two-bath Cape Cod style home in the desirable hamlet of Hawthorne, within the Town of Mount Pleasant. Lovingly maintained by the same family for decades, this inviting home is ready for its next chapter. Move in comfortably and personalize the home over time—its well-kept interior offers wonderful potential for thoughtful updates that reflect your own taste and style. The convenient location is a commuter’s delight, with the Hawthorne Metro-North station within walking distance and direct service to Grand Central Terminal. Residents enjoy excellent town recreation, a community pool, nearby shopping, and easy access to surrounding communities. Just minutes away, the Village of Pleasantville offers wonderful dining, shops, and its popular farmers market—one of the largest in Westchester County. A special opportunity to create the home you have been dreaming of in a convenient and welcoming Westchester community!

Wonderfully updated and beautifully maintained, this charming Village Colonial offers the perfect combination of character, comfort, and convenience. Located within a 10 minute walk to Metro North and the Hudson River, this home is ideal for commuters! Enter through the front porch to find inside, hardwood floors flowing throughout the home. The open living and dining area features elegant crown molding, built in shelving and cabinetry, and a welcoming layout that’s perfect for entertaining. A convenient first-floor bedroom and updated full bath provide flexibility for guests, a home office, or one-level living. The updated kitchen features a new floor, stainless steel appliances, and a stainless steel sink, with a door leading directly to an expansive, low-to-the-ground deck. Enjoy the private, level property—ideal for outdoor dining, entertaining, or simply relaxing. A 2006 addition included framing, siding windows, electrical and plumbing. Upstairs you'll find three generously sized

Offered for the first time ever, 21 Hawkes Avenue is a one of a kind contemporary residence in the Town of Ossining custom built by its current owner, an accomplished contractor, and designed by architect Jim Picone. Completed in 1983 and thoughtfully improved over the years, the home sits on a private, wooded 1.5-acre parcel originally acquired in 1980. A winding, tree-lined driveway leads to the residence, which is perfectly positioned atop a gentle rise overlooking beautifully maintained grounds. Defined by dramatic rooflines, soaring ceilings, expansive windows, and striking geometric forms, the home was designed to blur the line between indoors and out while embracing its natural surroundings. Surrounded by mature specimen trees, stone edged gardens, broad lawns, and woodland, the property offers exceptional privacy. A historic stone wall borders a gently flowing creek at the edge of the property, creating a peaceful setting rich with wildlife and seasonal beauty. Stone and timber

Bring your vision and restore the charm of this classic 1938 Yorktown Heights Farmhouse Cape Home. Full of character and timeless details, this 3-bedroom, 1-bath residence features high ceilings, graceful archways, and original moldings throughout. A welcoming front sunroom greets you upon entry, while a second sunroom at the rear of the home provides additional living space filled with natural light. A full staircase leads to a un-finished attic, offering flexible space for a home office, playroom, guest area, or additional storage. Situated on a generous 0.34-acre lot, the property offers plenty of outdoor space and endless potential. Rich with original charm, this home presents a wonderful opportunity to update and customize it to your own style while preserving its unique architectural character. Ideally located in close proximity to the Yorktown Town Pool, as well as shopping, restaurants, parks, schools, and major roadways. Don’t miss the opportunity to make this charming home yo

Centrally located in the historic Village of Sleepy Hollow, just one block from vibrant Beekman Avenue, this turnkey Two-Family home with numerous improvements and updates in recent years, offers an exceptional opportunity for owner-occupants and investors alike. Both units are uniquely large duplexes. 1,745 SF (4 bed, 2 full baths) and 1,650 SF (3 bed, 2 full baths). Each featuring a private deck, an eat-in kitchen, in-unit laundry, high ceilings, tall windows, and on-site parking. This property is ideally suited for those looking to live in one unit while offsetting their mortgage and property taxes with rental income, or investors looking to add to their rental portfolio. Within one mile you’ll find the Metro-North Tarrytown Station (36 minutes from NYC), the scenic Hudson River waterfront, marinas, restaurants, and the transformative Edge-on-Hudson development, DeCicco & Sons gourmet supermarket, and more. If you enjoy street fairs, cultural festivals, live jazz, rich history, loca

Pre-construction. Model will be complete late spring 2026! Discover luxury living at Enclave at Armonk by Toll Brothers in esteemed Westchester County. This community is an intimate enclave of two-story townhomes offering luxury features from top brand-name manufacturers such as Kohler fixtures, Century cabinets, stainless steel appliances, and much more. This quick move-in home is a Wilkerson model with the primary bedroom on the first floor. Enjoy open living with a wood-burning fireplace in great room. You can walkout from your great room to a deck and enjoy the views. Enjoy entertain in the finished lower level with a full bath and slider out to yard. This home site is situated close to amenities and the entrance. Will be ready for Fall 2026 occupancy. Homeowners will enjoy low-maintenance living with lawn care and snow removal provided. Enclave at Armonk by Toll Brothers is ideally located close to major commuter routes, including 684, I-95, I-287, Merritt Parkway, and Bronx River

Nestled at the end of a quiet, tree-lined cul-de-sac in Armonk's coveted Yale Farms neighborhood, this beautifully updated cedar shingle home seamlessly blends timeless architecture with modern comfort. Set on just over three exceptionally private, level acres, the property offers a peaceful retreat just minutes from downtown Armonk, Byram Hills schools, restaurants, and parks. Thoughtfully designed for today’s lifestyle, the home offers an effortless flow, graciously proportioned living spaces, and abundant natural light throughout. At the heart of the home, the spacious eat-in kitchen is anchored by a charming fireplace and opens directly to the expansive deck, creating an ideal setting for everyday living and indoor-outdoor entertaining. The spectacular family room showcases soaring vaulted ceilings, walls of windows, a wood burning fireplace, and direct access to the deck, offering an inviting space to gather year-round. Upstairs, you will find three generously sized bedrooms, incl

Nestled in the highly desirable Rolling Hills neighborhood, this ranch home offers exceptional potential. The main level features 2 bedrooms, a full bath, home office/den, a spacious living room with a cozy wood-burning stove, a formal dining room and an eat-in kitchen with door to the patio. Ideal for everyday living and entertaining. The lower level adds approximately 963 square feet of finished space, complete with storage, laundry, utilities and walk-out access. Whether you're looking for a home office, recreation room, guest space or flexible bonus area, this level offers endless possibilities. Additional highlights include a 2-car garage, a quiet setting and a beautiful private level yard offering plenty of space for relaxation, gardening or outdoor activities. Conveniently located close to shopping, dining, parks, school, and major transportation routes, this home presents a wonderful opportunity in one of the area's most sought-after neighborhoods

Attention work-at. Home professionals and those seeking mother daughter set up! Discover a true Pleasantville unicorn — a charming 1930’s single family home with legal commercial ground floor space offering rare flexibility, unbeatable walkability, and the kind of village convenience buyers dream about. Perfectly situated just 0.2 miles to the Pleasantville Metro-North Station, 0.4 miles to Bedford Road School, and 0.3 miles to both the Middle and High Schools, this home delivers effortless access to every part of town. Shops, dining, parks, the Farmers Market, and the Jacob Burns Film Center are all moments away, with easy ON/OFF access to the Saw Mill River Parkway for seamless commuting. County Tax classification code is R-02, the ground-floor unit is a standout feature — ideal as a professional home office (light business permitted) or as a 750 sq ft above ground living space. Previously used as a real estate office, it now functions as a comfortable residential space with endless

First time on the market in over 50 years—an exciting opportunity to create something truly your own in an exceptional location! Ideally situated between the vibrant Villages of Pleasantville and Chappaqua, this split-level home offers a wonderful canvas for its next owner to renovate, reimagine, and make their own. Inside, hardwood floors and abundant natural light set the stage for a fresh transformation. The main level offers excellent potential to create the open-concept kitchen, living, and dining space, so desirable for today’s lifestyle, with convenient access to the deck and backyard—perfect for entertaining, dining outdoors, or simply enjoying your own private outdoor space. Upstairs, three comfortable bedrooms and a full bath provide a traditional bedroom level, while the lower level offers valuable additional space with endless possibilities for a recreation room, home office, gym, or den, along with laundry, utilities, and garage access. And then there’s the location! Enjoy

PRE-CONSTRUCTION / available for summer 2026 move-in. Discover luxury living at Enclave at Armonk by Toll Brothers in esteemed Westchester County. This community is an intimate enclave of two-story townhomes offering luxury features from top brand-name manufacturers such as Kohler fixtures, Century cabinets, stainless steel appliances, and much more. This quick move-in home is a Saunders Farmhouse model in completely designed with the primary bedroom on the first floor. Enjoy open living with a wood-burning fireplace in great room and upper loft. You can walkout from your great room to a patio and enjoy the serene views of conservation land. Home site is situated on cul de sac street. This home has been thoughtfully designed by our Design Center. Home will be ready for Summer 2026 occupancy. Homeowners will enjoy low-maintenance living with lawn care and snow removal provided. Enclave at Armonk by Toll Brothers is ideally located close to major commuter routes, including 684, I-95, I-2