Westchester, NY Homes

• 

  $1,690,995 Sold Jun 30, 2025

  • 3,335 Sq Ft
  • $507/SF
  • 199 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2024

  18 Dewitt Dr Unit 71, Chappaqua, NY 10514

  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

  Thomas Jacovino Toll Brothers Real Estate Inc.

  18 Dewitt Dr Unit 71, Chappaqua, NY 10514
• 

  Est $1,250,424 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,872 Sq Ft

  619 Quaker Rd, Chappaqua, NY 10514

  619 Quaker Rd, Chappaqua, NY 10514
• 

  

  

  /27

  $739,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,687 Sq Ft

  400 Saw Mill River Rd, Millwood, NY 10546

  Timeless charm, curb appeal, and fantastic location in the Chappaqua School District. This Cape Cod home sits on a level and fenced property on a neighborhood street with a cul-de-sac. Step inside from the inviting covered front porch into the sun-filled living room with a wood-burning fireplace. The adjacent dining room flows seamlessly into the updated kitchen with a heated floor and a door

  Edward Holmes William Raveis-New York, LLC

  400 Saw Mill River Rd, Millwood, NY 10546
• 

  $2,250,000 Sold Jun 27, 2025

  • 4,807 Sq Ft
  • $468/SF
  • 18 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1993

  97 Random Farms Dr, Chappaqua, NY 10514

  Nestled in the prestigious Random Farms community, this beautifully updated 4-bedroom Colonial blends timeless elegance with modern convenience. Designed for effortless living, the open-flow layout seamlessly connects the renovated chef’s kitchen to a sun drenched great room, featuring a sophisticated fireplace as its centerpiece, while formal living and dining spaces add refinement. A dedicated

  Sari Shaw Compass Greater NY, LLC

  97 Random Farms Dr, Chappaqua, NY 10514
• 

  Est $967,917 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,740 Sq Ft

  625 Quaker Rd, Chappaqua, NY 10514

  625 Quaker Rd, Chappaqua, NY 10514
• 

  

  /43

  $1,599,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 3,087 Sq Ft

  90 Prospect Dr, Chappaqua, NY 10514

  Welcome to 90 Prospect Drive, a timeless Dutch Colonial nestled on over an acre of picturesque, park-like land in the heart of Chappaqua’s walkable village center. Just a 7-minute stroll to town, train, restaurants, shops, and parks, and only a 5-minute drive to Whole Foods and Life Time Fitness, this rare in-town gem also sits in one of Westchester’s most sought-after school districts. Set back

  Stacy Levey William Raveis-New York, LLC

  90 Prospect Dr, Chappaqua, NY 10514
• 

  $950,000 Sold Jun 27, 2025

  • Land
  • 26 Acres
  • $35,849 per Acre

  • 96 Days On Market

  249 Croton Dam Rd, Ossining, NY 10562

  DO NOT ACCESS THIS PROPERTY, THERE ARE SURVEILLANCE CAMERAS,OWNERS WILL CALL THE POLICE. Land for sale, zoning for 2 acres SF homes. Set on 26.50 acres, serene private property with original plantings untouched for over 100 years. Hiking trails throughout this property is adjacent to the Ossining Nature preserve. Also available for sale mls #6297365. As per sellers request please submit proof of

  Christina DiMinno Julia B Fee Sothebys Int. Rlty

  249 Croton Dam Rd, Ossining, NY 10562
• 

  Est $1,075,279 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,830 Sq Ft

  1283 Hardscrabble Rd, Chappaqua, NY 10514

  1283 Hardscrabble Rd, Chappaqua, NY 10514
• 

  

  /10

  $1,724,995 Pending

  • 2 Beds
  • 4 Baths
  • 3,432 Sq Ft

  19 Wallace Way Unit 25, Chappaqua, NY 10514

  FULLY DECORATED AND FURNISHED MODEL HOME FOR SALE. 3432’ ‘Square Feet, 2 BR Byram Farmhouse. This model home includes an array of Luxury upgrades, which you can enjoy and move into this school year (Fall 2025). The Byram includes a finished basement with half bath and many more luxurious finishes. The open concept great room and kitchen allow for large family gatherings. The open island with

  Andrea Martone Houlihan Lawrence Inc.

  19 Wallace Way Unit 25, Chappaqua, NY 10514
• 

  $1,320,000 Sold Jun 26, 2025

  • 2,287 Sq Ft
  • $577/SF
  • 29 Days On Market

  • 2 Beds
  • 3.5 Baths
  • Built 1988

  136 Ruxton Rd, Mount Kisco, NY 10549

  Chappaqua school district end unit townhome in the very desired Riverwoods community filled with every amenity you could dream of. Lives like a 3 bedroom!! Primary suite on the first floor as well as another en suite bedroom. En suite Playroom up stairs with a separate office area. Walk out lower level with exceptionally high ceilings, double deck, on gas and sewer. Lower walk out level has an

  Yona Strougo Compass Greater NY, LLC

  136 Ruxton Rd, Mount Kisco, NY 10549
• 

  Est $2,123,735 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 4,141 Sq Ft

  660 Quaker Rd, Chappaqua, NY 10514

  660 Quaker Rd, Chappaqua, NY 10514
• 

  

  /50

  $1,799,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 5,089 Sq Ft

  73 Random Farms Dr, Chappaqua, NY 10514

  Stately and Inviting, with a rocking chair front porch, this beautifully landscaped Post-Modern Colonial sitting on .73 acres is up for sale in the highly sought-after Random Farms Community. On a lush, level property framed with shade trees, this extraordinary house is beautifully designed and laid out. Enter this 5-bedroom 4.5 bath wonder through a light-filled double height foyer featuring

  Alicja Bohmrich Houlihan Lawrence Inc.

  73 Random Farms Dr, Chappaqua, NY 10514
• 

  $956,000 Sold Jun 25, 2025

  • 2,684 Sq Ft
  • $356/SF
  • 17 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1968

  21 Vails Ln, Ossining, NY 10562

  Discover the perfect blend of elegance and comfort in this stunning 5-bed, 3.5-bath colonial home situated on 1 acre with a pool, circular driveway, in the vibrant town of Ossining.Step inside through the formal entry into an oversized living room, bathed in abundant natural light and featuring gleaming hardwood floors. Entertain in the formal dining room, which boasts sliders leading out to an

  Sherry Wiggs Houlihan Lawrence Inc.

  21 Vails Ln, Ossining, NY 10562
• 

  Est $2,573,568 Not Listed For Sale

  • 5 Beds
  • 6 Baths
  • 6,349 Sq Ft

  650 Quaker Rd, Chappaqua, NY 10514

  650 Quaker Rd, Chappaqua, NY 10514
• 

  

  /47

  $1,599,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 5,357 Sq Ft

  43 Random Farms Cir, Chappaqua, NY 10514

  Discover the most private home in the prestigious Random Farms community of Chappaqua, NY. Tucked away amid lush, mature landscaping, this stunning five-bedroom contemporary colonial offers a rare sense of natural seclusion and tranquility. Enjoy the ultimate in privacy without sacrificing convenience—just a short stroll to the neighborhood pool, clubhouse, and tennis courts. This exceptional

  Suzan Zeolla Houlihan Lawrence Inc.

  43 Random Farms Cir, Chappaqua, NY 10514
• 

  $1,450,000 Sold Jun 25, 2025

  • 2,533 Sq Ft
  • $572/SF
  • 5 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1950

  132 Devoe Rd, Chappaqua, NY 10514

  Welcome to this lovely home within the very desirable Hillholme community in Chappaqua. Perfectly maintained and set beautifully on a flat large acre for all to enjoy. The bedrooms are all very spacious, there is a dedicated home office/study that ensures productivity, while the basement adds a great space for a play area. The backyard is a dream - lush green grass, deck and patio for barbecues

  Yona Strougo Compass Greater NY, LLC

  132 Devoe Rd, Chappaqua, NY 10514
• 

  Est $1,657,994 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,307 Sq Ft

  20 Suzanne Ln, Chappaqua, NY 10514

  20 Suzanne Ln, Chappaqua, NY 10514
• 

  

  /28

  $699,222 Pending

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft

  448 Saw Mill River Rd, Millwood, NY 10546

  Charming Updated Cape Cod-Style Home offers the perfect blend of charm and modern convenience. Featuring thoughtful upgrades throughout, this residence is move-in ready and ideal for comfortable living and entertaining. The Modern Kitchen was designed with both style and function in mind, enjoy granite countertops, stainless steel appliances, and double ovens—perfect for everyday cooking and

  Mark Seiden Mark Seiden Real Estate Team

  448 Saw Mill River Rd, Millwood, NY 10546
• 

  $1,495,322 Sold Jun 23, 2025

  • 3,200 Sq Ft
  • $467/SF
  • 14 Days On Market

  • 2 Beds
  • 3.5 Baths
  • Built 1998

  66 Burr Farms Rd, Mount Kisco, NY 10549

  A beautifully maintained Bravo model end-unit tucked away in a private location in the Riverwoods Community in Mount Kisco, NY. This bright, spacious, and versatile layout lives like a 3-bedroom. The open layout on the main level features high ceilings, oversized windows, a formal living room and dining area, an eat-in kitchen with center island and family room with fireplace and custom

  Edward Holmes William Raveis-New York, LLC

  66 Burr Farms Rd, Mount Kisco, NY 10549
• 

  Est $1,248,721 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 4,447 Sq Ft

  1266 Hardscrabble Rd, Chappaqua, NY 10514

  1266 Hardscrabble Rd, Chappaqua, NY 10514
• 

  

  /40

  $1,199,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,880 Sq Ft

  34 Glenside Place, Chappaqua, NY 10514

  Live minutes from the heart of Chappaqua! Commuters dream to live in this charming tudor-style home near all everyday amenities. Nestled on 1.11 acres, with 3-bedrooms and 2 bathrooms, this fully renovated residence offers timeless character and thoughtful updates throughout. The main level features an inviting entry foyer, a chef’s eat-in kitchen equipped with a gas oven/range, microwave, and

  Christine Ricci Keller Williams NY Realty

  34 Glenside Place, Chappaqua, NY 10514
• 

  $3,000,000 Sold Jun 23, 2025

  • 6,333 Sq Ft
  • $474/SF
  • 21 Days On Market

  • 6 Beds
  • 7.5 Baths
  • Built 1994

  66 Kerry Ln, Chappaqua, NY 10514

  Welcome Home to Your Dream Colonial in the Chappaqua School District. Discover luxury and comfort in this sunlit center-hall colonial, boasting over 6,333+ square feet of living space. Set back on 2.25 private, level acres, this home features a fenced-in backyard with a heated saltwater pool, an automatic cover, and expansive patio and deck spaces perfect for entertaining and recreation.

  Stacey Sporn William Raveis Real Estate

  66 Kerry Ln, Chappaqua, NY 10514
• 

  Est $1,293,183 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 3,186 Sq Ft

  24 Hilltop Dr, Chappaqua, NY 10514

  24 Hilltop Dr, Chappaqua, NY 10514
• 

  

  /36

  $1,249,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,420 Sq Ft

  31 Wynnewood Rd, Chappaqua, NY 10514

  Charming & renovated Colonial set on a quiet street just a few minutes from Chappaqua’s town and train station, effortlessly blends character with thoughtful modern updates. Surrounded by mature trees, professional landscaping with specimen plantings, and flowering perennial gardens, this home offers a truly special outdoor setting with a flat yard, tiered deck, stone patio, and fire pit—perfect

  Cindy Glynn Compass Greater NY, LLC

  31 Wynnewood Rd, Chappaqua, NY 10514
• 

  $1,402,970 Sold Jun 23, 2025

  • 2,945 Sq Ft
  • $476/SF
  • 142 Days On Market

  • 2 Beds
  • 3.5 Baths
  • Built 2024

  8 Dewitt Dr Unit 66, Chappaqua, NY 10514

  HOME IS UNDER CONSTRUCTION. MOVE in SUMMER 2025. 2 BR, 3 Full, 1 half primary on main floor, finished basement with full bath and media room. Additional Information: ParkingFeatures:2 Car Attached,

  Thomas Jacovino Toll Brothers Real Estate Inc.

  8 Dewitt Dr Unit 66, Chappaqua, NY 10514
• 

  Est $1,280,555 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,836 Sq Ft

  48 Hilltop Dr, Chappaqua, NY 10514

  48 Hilltop Dr, Chappaqua, NY 10514
• 

  

  /25

  $699,999 Pending

  • 2 Beds
  • 2 Baths
  • 1,775 Sq Ft

  52 Red Oak Ln, Mount Kisco, NY 10549

  This beautifully renovated ranch-style home, located in the desirable Chappaqua School District, offers both charm and practicality. Situated on a peaceful, tree-lined street and within walking distance to Smith Park, it’s the perfect setting for a variety of lifestyles. The extensive renovations completed in 2023 have ensured this home is move-in ready, requiring nothing more than your personal

  Kile Boga-Ibric Houlihan Lawrence Inc.

  52 Red Oak Ln, Mount Kisco, NY 10549
• 

  $1,250,000 Sold Jun 20, 2025

  • 2,144 Sq Ft
  • $583/SF
  • 11 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1973

  64 Stornowaye St, Chappaqua, NY 10514

  Inside & outside blend seamlessly together throughout this sleek, modern 3-bed/2-bath contemporary, wrapped by a massive deck front, side & rear, and privately set back from the road on two peaceful, sylvan acres on a cul-de-sac in the sought-after Whippoorwill neighborhood. Great layout for entertaining. Arts & crafts-inspired living room illuminated by large front-facing windows & topped with a

  Stacy Levey William Raveis-New York, LLC

  64 Stornowaye St, Chappaqua, NY 10514
• 

  Est $1,542,594 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,563 Sq Ft

  7 Hilltop Cir, Chappaqua, NY 10514

  7 Hilltop Cir, Chappaqua, NY 10514
• 

  

  /44

  $2,795,000 Pending

  • 5 Beds
  • 7 Baths
  • 6,673 Sq Ft

  5 Club Way, Mount Kisco, NY 10549

  Experience timeless elegance and modern luxury at 5 Club Way—a custom-built, light filled shingle and stone Young Colonial perfectly sited at the end of a quiet cul-de-sac in the coveted Lawrence Farms East enclave with Chappaqua Schools. Privately set on beautifully landscaped level acre with mature plantings and stone walls, pool and spa; this 5 bedroom, 4 full and 2 half bath residence offers

  Barbara Pagliuca Houlihan Lawrence Inc.

  5 Club Way, Mount Kisco, NY 10549
• 

  $281,250 Sold Jun 18, 2025

  • Land
  • 1.95 Acres
  • $144,231 per Acre

  • 27 Days On Market

  648 Pinesbridge Rd, Ossining, NY 10562

  Discover the perfect blend of privacy and convenience with this 1.95-acre wooded lot on Pinesbridge Road in Southern Yorktown. Nestled in a serene setting, this ready-to-build property offers an approvable space for a 3-bedroom home, with the potential for a 4-bedroom approval pending additional testing. Enjoy the tranquility of nature while remaining just a short drive from town centers,

  Susan Pratt Coldwell Banker Realty

  648 Pinesbridge Rd, Ossining, NY 10562
• 

  Est $1,545,932 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,369 Sq Ft

  2 West Way, Chappaqua, NY 10514

  2 West Way, Chappaqua, NY 10514
• 

  

  /29

  $1,079,000 Pending

  • 2 Beds
  • 1.5 Baths
  • 2,300 Sq Ft

  9 Campfire Rd, Chappaqua, NY 10514

  Welcome to this true storybook home in the heart of Chappaqua. Lives like a 3 bedroom and more. The exquisitely renovated kitchen is expertly crafted with custom cabinetry, quartzite countertops, gas range and herringbone floors. Enter the home through an elegant arched foyer that opens to a sophisticated living room with a gas fireplace, creating a warm and inviting ambience. The dining room

  Therese Herrero Coldwell Banker Realty

  9 Campfire Rd, Chappaqua, NY 10514
• 

  $281,250 Sold Jun 18, 2025

  • Land
  • 1.88 Acres
  • $149,601 per Acre

  • 27 Days On Market

  644 Pinesbridge Rd, Ossining, NY 10562

  This rare 1.88 acre property in Southern Yorktown offers the perfect blend of privacy and convenience and is an approvable 5 bedroom septic lot. Located on Pinesbridge Road you’ll find a peaceful wooded setting yet just a short drive to town centers, Metro-North, and the Taconic Parkway, with easy access to the NYS Empire State Trail and Kitchawan Preserve for outdoor recreation. The adjacent

  Susan Pratt Coldwell Banker Realty

  644 Pinesbridge Rd, Ossining, NY 10562
• 

  Est $2,201,434 Not Listed For Sale

  • 4 Beds
  • 6 Baths
  • 6,444 Sq Ft

  1 Green Ln, Chappaqua, NY 10514

  1 Green Ln, Chappaqua, NY 10514
• 

  

  /47

  $1,950,000 Pending

  • 4 Beds
  • 4.5 Baths
  • 3,531 Sq Ft

  33 North Way, Chappaqua, NY 10514

  Life's a breeze in this elegant, Hamptons-esque Cape Cod set on 2.67 verdant acres with sparkling, heated, gunite, in-ground pool within prestigious Lawrence Farms South. A towering flagpole stands sentry in the impressive stone walled circular drive. The cedar shingle residence exudes charm from the moment you enter and has a great layout for entertaining. A welcoming entry immediately

  Stacy Levey William Raveis-New York, LLC

  33 North Way, Chappaqua, NY 10514
• 

  $1,500,000 Sold Jun 17, 2025

  • 3,230 Sq Ft
  • $464/SF
  • 25 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1964

  23 Round Hill Rd, Chappaqua, NY 10514

  Welcome to 23 Round Hill Road, a picture-perfect, timeless, Center Hall Colonial on a premier street just minutes from Chappaqua schools, train station, & a variety of restaurants, shops & grocery stores (including Whole Foods & Starbucks), a prime location for convenience & lifestyle. Set on a beautifully landscaped property, this home exudes classic appeal. As you step through double front

  Michael Levy eXp Realty

  23 Round Hill Rd, Chappaqua, NY 10514
• 

  Est $1,583,518 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 3,291 Sq Ft

  55 Shadow Brook Pkwy, Chappaqua, NY 10514

  55 Shadow Brook Pkwy, Chappaqua, NY 10514
• 

  

  /32

  $999,000 Pending

  • 3 Beds
  • 3.5 Baths
  • 2,313 Sq Ft

  326 Millwood Rd, Chappaqua, NY 10514

  Welcome to this enchanting, character and light-filled Colonial, nestled on beautiful grounds in the sought-after Chappaqua school district. This gracious home blends timeless character with modern updates, featuring a WOW chef’s kitchen with stainless appliances, a travertine countertops, that has been proudly showcased in Old House Journal magazine. Thoughtfully designed for both everyday

  Cindy Glynn Compass Greater NY, LLC

  326 Millwood Rd, Chappaqua, NY 10514
• 

  $1,382,000 Sold Jun 16, 2025

  • 2,684 Sq Ft
  • $515/SF
  • 11 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1964

  3 Courtmel Rd, Mount Kisco, NY 10549

  This 4-bedroom Colonial sits on 1.4 acres of private property in the Chappaqua school district. Step inside the spacious entry foyer that leads into a bright open floor plan. The living room features a wood-burning fireplace while the dining and family rooms have sliding doors to the deck and backyard. The updated eat-in kitchen, with granite counters and stainless-steel GE Cafe appliances,

  Edward Holmes William Raveis-New York, LLC

  3 Courtmel Rd, Mount Kisco, NY 10549

Showing Results 161 - 200, Page 5 of 18