Buy houses in Chappaqua - Nestoria

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House · for sale

USD 899,000

USD 477/sq.ft

Updated

4 Depew Street

Chappaqua

· 1,884 sq.ft · 3 Bedrooms · 2 Baths · House

· Office room

Chappaqua · 1,884 sq.ft · 3 Bedrooms · 2 Baths · House · Office room

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

USD 899,000

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House · for sale

USD 599,000

USD 452/sq.ft

582 Washington Avenue

Chappaqua

· 1,324 sq.ft · 3 Bedrooms · 1 Bath · House

· Garden · Office room · Gym · Deck · Equipped kitchen · Parking

Chappaqua · 1,324 sq.ft · 3 Bedrooms · 1 Bath · House · Garden · Office room · Gym · Deck · Equipped kitchen · Parking

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

USD 599,000

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House · for sale

USD 1,800,000

USD 621/sq.ft

New

8 Rosehill Drive

Chappaqua

· 2,895 sq.ft · 4 Bedrooms · 3 Baths · House

· Equipped kitchen · Parking · Air conditioning

Chappaqua · 2,895 sq.ft · 4 Bedrooms · 3 Baths · House · Equipped kitchen · Parking · Air conditioning

New Construction 2026! Beautifully designed 4-bedroom, 3.1-bath home set on. 8 level acres on a quiet cul-de-sac. Bright and airy with two luxurious primary suites, including one on the main level, an expansive family room and spacious eat-in kitchen featuring a large stone island, custom cabinetry, top of the line GE Cafe appliances, wine cooler and 6-burner gas range. New Navien heating system, central A/C, spray foam insulation and 200-amp electric. Second-floor laundry, attic and lower-level storage with walk-out. Separate oversized 2-car garage with electric and water. Newly paved driveway, stone wall and front walkway. Private well with new filtration and UV system; town sewer. Minutes to town, shops and award-winning Byram Hills schools and approximately 7 miles to North White Plains Metro-North

USD 1,800,000

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House · for sale

USD 1,525,000

USD 569/sq.ft

11 Fieldstone Knoll 42

Chappaqua

· 2,680 sq.ft · 3 Bedrooms · 2 Baths · House

· Patio · Fireplace

Chappaqua · 2,680 sq.ft · 3 Bedrooms · 2 Baths · House · Patio · Fireplace

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

USD 1,525,000

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House · for sale

USD 7,790,000

USD 6,187/sq.ft

39 Orchard Drive

Chappaqua

· 1,259 sq.ft · 4 Bedrooms · 1 Bath · House

· Garden · Fireplace · Equipped kitchen

Chappaqua · 1,259 sq.ft · 4 Bedrooms · 1 Bath · House · Garden · Fireplace · Equipped kitchen

Set back on a lush, level. 43-acre property and framed by mature trees, this classic 1929 Dutch Colonial offers a wonderful sense of privacy and calm. Quiet and tucked away, yet convenient to the many amenities that make Ossining such a desirable place to call home, the setting is one of this property’s standout features. Inside, the gracious traditional layout reflects the craftsmanship and character of an earlier era, with solid wood doors, wood floors, ample closets, and charming architectural details throughout. A welcoming foyer opens to the formal living room with fireplace and formal dining room. The eat-in kitchen connects to a bright family room addition with vaulted ceiling and direct access to the yard, while a fabulous screened-in porch just off the dining room provides an inviting seasonal space for morning coffee, casual meals, or summer evenings. A convenient half bath completes the first floor. Upstairs are four comfortably sized bedrooms with generous closet space and

USD 7,790,000

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House · for sale

USD 375,000

USD 325/sq.ft

3 Davids Lane

Chappaqua

· 1,152 sq.ft · 1 Bedroom · 1 Bath · House

· Balcony · Equipped kitchen · Swimming pool

Chappaqua · 1,152 sq.ft · 1 Bedroom · 1 Bath · House · Balcony · Equipped kitchen · Swimming pool

Discover an exceptional opportunity within the highly sought-after Liberty Knoll Town Home Community. Whether you are a first-time homebuyer seeking an entry into the Westchester market, a commuter desiring convenience with a walk to the Metro North Train Station or looking to downsize without compromising on quality and community, 3 Davids Lane presents a sophisticated, low-maintenance lifestyle. The main level boasts gleaming stainless-steel appliances in the kitchen updated powder room and built-in cabinetry with beverage center. The open layout extends to a private balcony which is perfect for al fresco dining or enjoying quiet moments. The upper level provides a tranquil retreat, featuring a generous sized bedroom with a large walk-in closet, a well-appointed updated full bathroom and a dedicated laundry area complete with washer and dryer. The home also has exceptional storage in the lower level. Residents enjoy access to an outdoor pool and well-equipped clubhouse. A children's

USD 375,000

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House · for sale

USD 799,500

USD 401/sq.ft

1704 Paine Street

Chappaqua

· 1,991 sq.ft · 4 Bedrooms · 2 Baths · House

· Garden · Deck · Equipped kitchen · Air conditioning

Chappaqua · 1,991 sq.ft · 4 Bedrooms · 2 Baths · House · Garden · Deck · Equipped kitchen · Air conditioning

Welcome to this beautiful well maintained split level home in the center of yorktown heights with a tastefully custom made kitchen, hardwood floors throughout, four well size bedrooms one of them opening to a nice size deck overlooking the spacious backyard, two full bathrooms one in each level with a massive double lot which extends from one street all the way to the other behind. Lower level of home features a full living room which walks out to yard, full bath, bedroom and laundry room. This home is move in ready with major updates already done all you have to pick is your paint colors. Home has central ac unit, massive driveway with space to fit four cars, backyard features a beautiful stone pathway with leads to a nice gazebo sitting area overlooking the playground who's ready to welcome kids. Come and see what this home and yorktown has to offer before its gone, the school bus stops literaly in front of the home to get your kids to school while you watch from the window with your

USD 799,500

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House · for sale

USD 579,000

USD 275/sq.ft

Updated

661 Warren Avenue

Chappaqua

· 2,099 sq.ft · 3 Bedrooms · 1 Bath · House

· Cellar

Chappaqua · 2,099 sq.ft · 3 Bedrooms · 1 Bath · House · Cellar

The price is right and bring your vision to make 661 Warren Avenue your home. It’s BEING SOLD AS IS and needs TLC, but a lot of potential. Large full size walkout basement with plenty of storage and work area. Taxes do not include the star reduction of $1,382. Walking distance to METRO North. 40 minutes to Grand Central. Just minutes away from local shopping, dining and grocery stores, as well as easy access to all major highways and public transit

USD 579,000

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House · for sale

USD 650,000

USD 413/sq.ft

263 Willis Avenue

Chappaqua

· 1,572 sq.ft · 3 Bedrooms · 1 Bath · House

· Garden · Deck · Fireplace · Equipped kitchen

Chappaqua · 1,572 sq.ft · 3 Bedrooms · 1 Bath · House · Garden · Deck · Fireplace · Equipped kitchen

Classic charm meets easy modern living in this Shaker-style ranch tucked into one of Hawthorne’s most desirable neighborhoods. With three bedrooms and one full and an adjacent half bath, this home offers an inviting foundation with plenty of opportunity to make it distinctly your own. Inside, the spacious living room centers around a wood-burning fireplace, while the separate dining room creates an easy setting for everything from weeknight dinners to entertaining. The eat-in kitchen offers direct access to the private wood deck, complete with a retractable awning, the perfect spot for morning coffee, summer dinners, or simply enjoying the backyard. The spacious primary suite features a crisp, modern primary bath, while two additional bedrooms provide flexibility for guests, a home office, creative space, or whatever life calls for. Multiple entries and exits throughout the home create an easy connection between the interior and outdoors. And then there’s the backyard: flat, green, pri

USD 650,000

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House · for sale

USD 899,000

USD 525/sq.ft

20 North Street

Chappaqua

· 1,711 sq.ft · 2 Bedrooms · 2 Baths · House

· Patio · Garden · Office room · Parking · Fireplace · Equipped kitchen · Cellar

Chappaqua · 1,711 sq.ft · 2 Bedrooms · 2 Baths · House · Patio · Garden · Office room · Parking · Fireplace · Equipped kitchen · Cellar

Beautifully updated Cape located in the heart of the charming Village of Katonah! This stunning village gem lives like a 3 bedroom and offers the perfect blend of character and modern updates. A fully fenced front yard welcomes you to a covered front porch. The first floor features a cozy living room with a fireplace, an updated kitchen with an eat-in area, a first-floor bedroom, and a full bathroom. Upstairs, you’ll find the primary bedroom with a walk-in closet, along with a beautifully customized full bath featuring a large shower, double sinks and skylight. Rounding out the second floor is a large bonus space, perfect for an office, guest area or den. The property also boasts a private side and backyard complete with a play set, grilling area, spacious patio perfect for entertaining, and detached, heated one car garage. A partially finished basement adds valuable flex space along with a dedicated laundry area. A rare find in the acclaimed Katonah-Lewisboro School District! This hom

USD 899,000

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House · for sale

USD 1,250,000

USD 416/sq.ft

121 Marietta Avenue

Chappaqua

· 3,003 sq.ft · 5 Bedrooms · 4 Baths · House

· Office room · Fireplace · Equipped kitchen · Parking

Chappaqua · 3,003 sq.ft · 5 Bedrooms · 4 Baths · House · Office room · Fireplace · Equipped kitchen · Parking

Perfectly perched in one of Mount Pleasant's most desirable neighborhoods, this extraordinary 5-bedroom, 4-bath Colonial commands breathtaking western horizon views and offers a rare double-lot setting that delivers the privacy, space, and resort-style lifestyle few homes can match. Every inch has been thoughtfully reimagined with exceptional craftsmanship, designer finishes, and uncompromising attention to detail, creating a residence where luxury and functionality exist in perfect harmony. A charming breezeway/mudroom provides seamless access to both the attached garage and the main home before unveiling an interior that is nothing short of spectacular. The sun-filled living room welcomes you with a classic brick wood-burning fireplace, oversized picture window, and warm, inviting atmosphere. A first-floor bedroom creates the perfect guest suite, au pair quarters, or home office. At the heart of the home is a showstopping chef's kitchen designed to impress. Outfitted with premium sta

USD 1,250,000

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House · for sale

USD 1,250,000

USD 617/sq.ft

62 Hemlock Drive

Chappaqua

· 2,024 sq.ft · 4 Bedrooms · 2 Baths · House

· Garden · Deck · Fireplace · Equipped kitchen · Parking

Chappaqua · 2,024 sq.ft · 4 Bedrooms · 2 Baths · House · Garden · Deck · Fireplace · Equipped kitchen · Parking

Discover timeless Colonial charm at 62 Hemlock Drive, ideally situated in the sought-after village of Sleepy Hollow. Set on a beautifully level 0.38-acre property, this classic 1966 center hall Colonial offers four spacious bedrooms, 2.5 bathrooms, and an attached two-car garage. Beautifully updated for today’s lifestyle, the home showcases a state-of-the-art renovation featuring a stunning newly created kitchen that seamlessly flows into the main living area, creating an ideal space for everyday living and entertaining. The kitchen opens directly to a pristine deck overlooking the private, level backyard, making indoor-outdoor living effortless. Hardwood floors extend throughout the home, while the inviting family room features a wood-burning fireplace. A spacious formal dining room and sun-filled living room complete the main level. The second level boasts an expansive primary suite highlighted by a fully renovated spa-inspired bathroom and redesigned walk-in closet. Three additional

USD 1,250,000

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House · for sale

USD 950,000

USD 318/sq.ft

67 State Street

Chappaqua

· 2,982 sq.ft · 7 Bedrooms · 4 Baths · House

Chappaqua · 2,982 sq.ft · 7 Bedrooms · 4 Baths · House

Perfect for investor or end-user. Located in the heart of the village, the structure sits on a 4,356-square-foot lot and offers a classic architectural style characteristic of the historic downtown Ossining area. This multi-family, 2 family with accessory unit ground floor unit. Property features 7 bedrooms and 4 bathrooms

USD 950,000

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House · for sale

USD 525,000

USD 427/sq.ft

33 Cedar Lane

Chappaqua

· 1,227 sq.ft · 3 Bedrooms · 2 Baths · House

· Patio · Garden · Deck · Balcony · Fireplace · Equipped kitchen

Chappaqua · 1,227 sq.ft · 3 Bedrooms · 2 Baths · House · Patio · Garden · Deck · Balcony · Fireplace · Equipped kitchen

A true brick home in the Village of Ossining, offering beautiful sunset and river views, tremendous character, low taxes, and a location that’s hard to beat — just minutes to the train station, riverfront dining, and Teatown Nature Preserve. This 3-bedroom, 2-bath home features 1,240 sq ft across the main floors, plus a 340 sq ft walk-out lower level and a walk-up attic ideal for an artist loft, studio, or storage. Inside, original exposed beam ceilings and a striking stone-and-brick fireplace with a Jotul wood stove sets an unmistakable tone. Outside, enjoy a rare three-tiered outdoor living setup: a brick patio off the lower level, a large deck off the kitchen, and an upper balcony with year-round views of the Mario Cuomo Bridge and Croton Point Park — expanding to a full 180-degree Hudson River panorama in winter. The lower level includes a convenient kitchenette for guests or extended living. Classic brick architecture, arched window lintels, mature trees, a large rear yard, and a

USD 525,000

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House · for sale

USD 1,290,000

USD 512/sq.ft

5 Hampton Place

Chappaqua

· 2,519 sq.ft · 4 Bedrooms · 2 Baths · House

· Deck · Fireplace · Equipped kitchen

Chappaqua · 2,519 sq.ft · 4 Bedrooms · 2 Baths · House · Deck · Fireplace · Equipped kitchen

Katonah Hamlet: This classic 4 Bedroom Colonial is full of timeless charm and ready for the next owner to bring their personal touches. Featuring beautiful hardwood floors throughout, crown molding, a custom fireplace in the family room and an updated Kitchen with stainless appliances, this home offers a warm and inviting atmosphere with a traditional layout ideal for everyday living and entertaining. Spacious rooms, abundant natural light and solid construction provide the perfect foundation for making this home your own. The oversized trek deck is a perfect place for outdoor dining, entertaining and has direct access to the country kitchen. Located in the sought after Hamlet of Katonah with sidewalks to all including elementary school, you'll enjoy the conveniences of charming shops, fine indoor and outdoor dining, fabulous library, old fashioned hardware store, cafes, Metro-North Station for easy NYC and local commuting and cultural destinations. Award winning Katonah/Lewisboro Scho

USD 1,290,000

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House · for sale

USD 725,000

USD 343/sq.ft

39 Secor Road

Chappaqua

· 2,110 sq.ft · 3 Bedrooms · 2 Baths · House

· Cellar · Parking

Chappaqua · 2,110 sq.ft · 3 Bedrooms · 2 Baths · House · Cellar · Parking

Welcome to 39 Secor Road. Being sold strictly as-is and as a buy one get one with 37 Secor Road (offered @ $85K CASH ONLY). You cannot pass on this deal. Get this rare investment opportunity for this two bedroom over 1-bedroom multi. Family home that offers street parking or with the purchase of municipal parking pass, tenants can park right behind the building in the municipal lot. This home boasts unobstructed windows of the Hudson River views from both units and the windows in the basement. Priced to be sold as a package with the adjoining Single-family home at 37 Secor road. These two homes are on one deed with two separate tax lots, but they are adjoined with ONE furnace and one oil tank. The single-family home is being sold for cash only while a buyer can obtain financing for the two-bedroom multi-family home. This is an amazing opportunity for a first time or veteran investor. Both units are being sold strictly AS IS but boast two new rooves. The unfinished basement extends the

USD 725,000

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House · for sale

USD 875,000

USD 343/sq.ft

New

1059 Hanover Street

Chappaqua

· 2,551 sq.ft · 4 Bedrooms · 2 Baths · House

· Garden · Office room · Fireplace · Equipped kitchen

Chappaqua · 2,551 sq.ft · 4 Bedrooms · 2 Baths · House · Garden · Office room · Fireplace · Equipped kitchen

Nestled in one of Southern Yorktown desirable residential setting, this home on Hanover St, offers the perfect blend of privacy, convenience, and suburban charm. This Historical Colonial Farmhouse sits on 2.35 of level usable land, offers 4 bedrooms, a den/office, 2.1 bathrooms, front and rear staircases, updated kitchen, two fireplaces, including the stone and brick fireplace, a dining room, a mudroom, first. Floor laundry-room. A spacious living with wood flooring, exposed beam. Step outside, you'll find a fenced in vegetable garden, small, detached outbuilding/studio, great for recreation or an office space. The backyard is a close walk to Hilltop Hanover Farm & Environmental Center. Enjoy scenic walking trails, parks, and open green space, just minutes to downtown Yorktown Heights. Located within the highly regarded Yorktown Central School District, this home offers an exceptional lifestyle in the heart of northern Westchester County

USD 875,000

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House · for sale

USD 990,000

USD 90/sq.ft

150 Bedford Road

Chappaqua

· 10,882 sq.ft · 1 Bedroom · 2 Baths · House

· Garden · Equipped kitchen · Parking

Chappaqua · 10,882 sq.ft · 1 Bedroom · 2 Baths · House · Garden · Equipped kitchen · Parking

A Gem in Armonk, centrally located in the center of Armonk. There are two structures on the property. Main Building can be used for commercial space. On the second floor with a separate entrance offers a 1 bedroom, eat. In kitchen, living room, full bath. Accessory cottage located on the property offers: Vaulted ceilings, wood-burning stove, kitchenette, Bedroom, Full Bathroom, Large finished loft for storage, level private yard. Ample storage in both buildings. Parking for about 10 cars

USD 990,000

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House · for sale

USD 499,999

USD 484/sq.ft

2014 Allan Avenue

Chappaqua

· 1,033 sq.ft · 3 Bedrooms · 1 Bath · House

· Deck · Cellar

Chappaqua · 1,033 sq.ft · 3 Bedrooms · 1 Bath · House · Deck · Cellar

Mid-century ranch-style home nestled on a private lot close to town! Arrive to a well-maintained exterior featuring a private deck, mature trees, lovely plantings, a stone wall, and a newer driveway. Inside, enjoy hardwood floors, generous bedrooms, and an unfinished basement offering great potential. With a little updating, make this home your own—a fantastic alternative to condo living with no HOA fees! Located just 2 miles from the Taconic State Parkway, enjoy unbeatable convenience moments from downtown Yorktown Heights, local shopping (Uncle Giuseppe's, TJ Maxx), the community theatre, walking track, and Sportime Pickleball Yorktown. Outdoor enthusiasts will love the proximity to the Empire State Trail and Mohansic Golf Course. Plus, benefit from seamless access to the upcoming Underhill Farms development featuring Bobo's and Wonder!

USD 499,999

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House · for sale

USD 2,400,000

USD 506/sq.ft

1349 Hanover Street

Chappaqua

· 4,736 sq.ft · 4 Bedrooms · 4 Baths · House

· Equipped kitchen

Chappaqua · 4,736 sq.ft · 4 Bedrooms · 4 Baths · House · Equipped kitchen

A Modern Farmhouse Estate Overlooking Protected Farmland at Cat Hill at Hilltop Hanover Farm Welcome to Cat Hill at Hilltop Hanover Farm, an exclusive enclave of just five custom-built modern farmhouse estates set among the rolling landscape and protected farmland of Hilltop Hanover. Offering a rare combination of contemporary luxury, timeless architecture, and peaceful countryside views, this is an extraordinary opportunity to own one of Northern Westchester's most distinctive new residences. Set on two private acres, this exceptional home was designed to embrace its surroundings, with expansive windows, soaring ceilings, and thoughtfully curated living spaces that blur the line between indoor comfort and outdoor beauty. Rich hardwood floors, refined finishes, and an open-concept floor plan create an atmosphere that feels both elegant and effortlessly livable. At the heart of the home, the chef's kitchen is a true showpiece, featuring an oversized center island, premium appliances, de

USD 2,400,000

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House · for sale

USD 789,000

USD 615/sq.ft

356 Marietta Avenue

Chappaqua

· 1,281 sq.ft · 3 Bedrooms · 2 Baths · House

· Garden · Deck · Equipped kitchen · Parking

Chappaqua · 1,281 sq.ft · 3 Bedrooms · 2 Baths · House · Garden · Deck · Equipped kitchen · Parking

Welcome to 356 Marietta Ave, a beautifully updated 3-bedroom, 2-bathroom home in the heart of Hawthorne that perfectly blends style, comfort, and functionality. The open-concept floor plan creates a bright, inviting living space that's ideal for both everyday living and entertaining. The updated kitchen features granite countertops, a breakfast bar, and modern appliances, offering plenty of space for cooking and gathering with family and friends. Thoughtful updates throughout the home make this property truly move-in ready. Step outside to an expansive deck overlooking a level backyard—perfect for entertaining. Parking is a breeze with an attached 2-car garage and a spacious driveway that accommodates up to four additional vehicles, providing ample space for family and guests. Ideally located just minutes from the Metro-North station, this home is perfect for commuters while also offering convenient access to shopping, dining, parks, and everyday amenities. Don't miss this opportunity

USD 789,000

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House · for sale

USD 1,225,000

USD 451/sq.ft

1 Grandview Circle

Chappaqua

· 2,713 sq.ft · 4 Bedrooms · 2 Baths · House

Chappaqua · 2,713 sq.ft · 4 Bedrooms · 2 Baths · House

Welcome to this beautifully situated 4-bedroom, 2-full-bath home in the heart of Pleasantville! Featuring a spacious primary bedroom, a large formal living room, and plenty of room to live, work, and entertain, this home offers both comfort and convenience. Enjoy the best of Pleasantville living with a truly walkable location close to schools, the train station, local farmers markets, and the popular Jacob Burns Film Center. A wonderful selection of restaurants, shops, and community amenities are all just moments away. With its inviting living spaces and unbeatable location, this home is a fantastic opportunity to enjoy all that Pleasantville has to offer!

USD 1,225,000

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House · for sale

USD 769,999

USD 483/sq.ft

179 Serrano Avenue

Chappaqua

· 1,593 sq.ft · 4 Bedrooms · 2 Baths · House

· Garden · Fireplace · Equipped kitchen

Chappaqua · 1,593 sq.ft · 4 Bedrooms · 2 Baths · House · Garden · Fireplace · Equipped kitchen

Welcome to 179 Serrano Avenue, Hawthorne, NY, where timeless charm meets everyday comfort in this inviting Cape Cod home nestled on a quiet, tree-lined street. Thoughtfully designed for flexible living, this home offers a highly desirable first-floor primary bedroom, an additional first-floor bedroom, and a full bath on the main level—perfect for guests, multi-generational living, or convenient one-level living. Step inside through the welcoming entrance foyer into a warm and inviting living room highlighted by a cozy wood-burning fireplace, creating the perfect setting for relaxing evenings. The bright eat-in kitchen features granite countertops, a breakfast bar, ample cabinetry, and plenty of space for casual dining and entertaining. Ceiling fans throughout add year-round comfort, while washer/dryer hookups and abundant storage provide everyday convenience. Enjoy outdoor living with a screened porch overlooking the backyard, offering the perfect place to unwind, entertain, or enjoy y

USD 769,999

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House · for sale

USD 699,000

USD 352/sq.ft

34 Cedar Street

Chappaqua

· 1,981 sq.ft · 5 Bedrooms · 2 Baths · House

· Garden · Office room · Equipped kitchen

Chappaqua · 1,981 sq.ft · 5 Bedrooms · 2 Baths · House · Garden · Office room · Equipped kitchen

Location, Location, Location. Own a Piece of New York's Halloween Capital. Sleepy Hollow! Located a few blocks from the Hudson River & all the Awesome sight's that make this Village Special: Historic Sleepy Hollow Cemetery & Old Dutch tours, Headless Horseman Bridge, Washington's Headless Horseman Statue & Haunted Orchards. Live here. A great investment & rent out the other unit, This desirable Multi-family home is the best place to Live. Imagine the possibilities. Was updated in past 20 years. Being sold As-is as. It needs some TLC! Unit#2. Upper floor 2 Bedroom unit has partial River/Bridge views, Pull down Attic that is excellent storage: partial standup with Plywood board flooring & 2 windows. Unit#1 is the Main Unit with Hard-Wood Floors Main floor entry into Living Room, Den/Home Office, Primary Bedroom w/stairs to back yard & Full Bathroom. Then 1 flight down to Bedroom 2 & 3, with lots of closets (including Hall Cedar closet), Large Eat in Kitchen, Mud room with exit to Back Ya

USD 699,000

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House · for sale

USD 449,000

USD 521/sq.ft

2070 Hamblyn Street

Chappaqua

· 861 sq.ft · 2 Bedrooms · 1 Bath · House

· Garden

Chappaqua · 861 sq.ft · 2 Bedrooms · 1 Bath · House · Garden

Ideally located in a prime location with easy access to shopping centers, restaurants, and everyday conveniences. This property features a flat, usable yard and is connected to municipal water and sewer. Enjoy direct access to a nearby walking and biking path that leads right into the heart of town. A short stroll to public transportation makes commuting a breeze, offering the perfect combination of convenience and lifestyle. The flexible floor plan offers endless possibilities, easily adapting to a variety of living needs and lifestyles

USD 449,000

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House · for sale

USD 975,000

USD 413/sq.ft

39 Park Drive

Chappaqua

· 2,357 sq.ft · 4 Bedrooms · 2 Baths · House

· Office room · Fireplace · Equipped kitchen · Air conditioning

Chappaqua · 2,357 sq.ft · 4 Bedrooms · 2 Baths · House · Office room · Fireplace · Equipped kitchen · Air conditioning

Welcome to 39 Park Drive, a beautifully updated Colonial nestled on a quiet cul-de-sac. Set on. 74 private acres, this move-in ready 4-bedroom, 2.5-bath home offers 2,363 square feet of thoughtfully designed living space, including a main-level office that can easily serve as a fifth bedroom, convenient main-floor laundry, a finished lower-level ideal for recreation, a home office, or additional living space, and abundant storage throughout. The renovated 2022 kitchen features an electric double oven, pot filler, recessed lighting, and opens to inviting living areas highlighted by both a wood-burning fireplace and gas stove. The spacious primary suite includes a his-and-her walk-in closet with a custom Closets by Design system, a dedicated vanity area, and an updated bath with a new sink and vanity (2022). Recent improvements include a new roof (2025), wood siding re-stained (2025), front and rear walkways and steps (2026), new three-zone boiler (2021), central air conditioning (2016),

USD 975,000

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House · for sale

USD 849,000

USD 415/sq.ft

239 Carolina Road

Chappaqua

· 2,045 sq.ft · 3 Bedrooms · 2 Baths · House

· Patio · Garden · Fireplace · Equipped kitchen · Air conditioning · Swimming pool

Chappaqua · 2,045 sq.ft · 3 Bedrooms · 2 Baths · House · Patio · Garden · Fireplace · Equipped kitchen · Air conditioning · Swimming pool

Move right into this spacious, sun-filled contemporary featuring an open floor plan and stylish updates throughout. The beautifully renovated kitchen offers premium cabinetry, quartz countertops, stainless steel appliances, and easy access to the private backyard with a fiberglass saltwater pool and a stone patio. Perfect for entertaining. The inviting living room boasts vaulted ceilings, a fireplace, oversized windows, and hardwood floors, while the spacious family room provides flexible living and recreation space. Updated baths, energy-efficient LED lighting, central air, vinyl siding, generator, pool equipment and lighting, town water, and natural gas complete this exceptional home. Ideally located in southern Yorktown, close to parks, bike and walking trails, schools, shopping, restaurants, the train, and major parkways

USD 849,000

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House · for sale

USD 1,699,000

USD 474/sq.ft

53 Windmill Road

Chappaqua

· 3,584 sq.ft · 4 Bedrooms · 3 Baths · House

· Garden · Sauna · Equipped kitchen · Parking

Chappaqua · 3,584 sq.ft · 4 Bedrooms · 3 Baths · House · Garden · Sauna · Equipped kitchen · Parking

Welcome home to Windmill Farm in the heart of Armonk. This four-bedroom raised ranch is the perfect combination of comfort and elegance, where a beautiful circular driveway and extensive landscaping set the tone from the moment you arrive. Inside, the home features a light-filled family room off the kitchen with cathedral ceilings, creating a bright and inviting atmosphere. The kitchen flows seamlessly into a formal dining room detailed with a great inset ceiling and custom lighting, leading into a fabulous, highly decorated living room framed by a wall of windows. The lower level offers an amazing bar and private sauna, and a mudroom that walks out to the side driveway area where there is plenty of parking for your guests. Set on a private, fenced-in bi level acre, the backyard is an ideal space for sports or large parties, accented by custom exterior lighting. Experience the ultimate in style and privacy, all just a short distance from the The Windmill Club

USD 1,699,000

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House · for sale

USD 749,000

USD 347/sq.ft

23 Howard Avenue

Chappaqua

· 2,153 sq.ft · 3 Bedrooms · 1 Bath · House

Chappaqua · 2,153 sq.ft · 3 Bedrooms · 1 Bath · House

Lives large with approximately 720 square feet of finished playroom with versatility. Great convenient location with a short stroll to Valhalla Metro North, Valhalla Crossing, Village Restaurants, Local Stores and Kensico Dam. Minutes to the Taconic/Bronx River, Sprain Brook Parkway and Shopping. Close to Westchester Community College, Westchester Medical Center, Maria Fareri Children's Hospital, Regeneron and a number of corporate parks. Small town living with big city access. New Roof 2024

USD 749,000

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House · for sale

USD 899,000

USD 338/sq.ft

20 Waller Avenue

Chappaqua

· 2,659 sq.ft · 4 Bedrooms · 3 Baths · House

· Garden · Parking · Equipped kitchen · Cellar

Chappaqua · 2,659 sq.ft · 4 Bedrooms · 3 Baths · House · Garden · Parking · Equipped kitchen · Cellar

Don't miss this opportunity to own a charming owner occupied only two family home full of character, situated on a beautiful corner lot with a welcoming front porch, great curb appeal, and a detached 2 car garage. This sun filled home features oversized windows, high ceilings, hardwood floors, original wood doors, thick floor moldings, and high hats throughout both units, blending timeless character with modern updates. The main level offers an updated kitchen with granite countertops, stainless steel appliances, a gas Viking stove, laundry, and access to a private backyard. The oversized primary bedroom features elegant arch and tray ceilings. The walk out basement includes a finished recreation room and plenty of storage. The second floor apartment features an updated kitchen, three bedrooms, two full bathrooms, and access to a finished attic with a wainscoted ceiling, providing excellent income potential or additional living space. Conveniently located just 0.5 miles from the Ossini

USD 899,000

2,878 houses for sale in Chappaqua

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