21,852

Westchester, NY Homes

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  • 50 Overlook Dr, Chappaqua, NY 10514
    50 Overlook Dr, Chappaqua, NY 10514
    50 Overlook Dr, Chappaqua, NY 10514
    /43

    $2,000,000 Pending

    • 6 Beds
    • 6 Baths
    • 5,234 Sq Ft

    50 Overlook Dr, Chappaqua, NY 10514

    50 Overlook Drive, an elegant 6-bedroom colonial Tudor set in a quiet, tree-lined neighborhood. With fresh upgrades completed this month, including interior repainting, carpet-removal to expose wood floors. This one-of-a-kind home is a must see. Meticulously maintained heating and cooling systems, brick exterior, and a classic-tile roof are some of the exceptional features this home can

    Wendy Nolan Houlihan Lawrence Inc.

    50 Overlook Dr, Chappaqua, NY 10514
  • 471 Chappaqua Rd, Briarcliff Manor, NY 10510

    $1,810,000 Sold Jun 23, 2025

    • 4,010 Sq Ft
    • $451/SF
    • 7 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1985

    471 Chappaqua Rd, Briarcliff Manor, NY 10510

    Welcome to this spectacular contemporary home in Briarcliff Manor, offering over 4,000 sq. ft. of thoughtfully designed living space on a beautiful private property, set back from the road. With low Mount Pleasant taxes and access to top-rated Briarcliff Manor schools and recreation, this home is the perfect blend of luxury, modern amenities, and tranquility.The main level features a

    Hillary Landau Compass Greater NY, LLC

    471 Chappaqua Rd, Briarcliff Manor, NY 10510
  • 21 Kipp St, Chappaqua, NY 10514
    21 Kipp St, Chappaqua, NY 10514
    21 Kipp St, Chappaqua, NY 10514
    /36

    $1,200,000 Pending

    • 4 Beds
    • 2.5 Baths
    • 2,447 Sq Ft

    21 Kipp St, Chappaqua, NY 10514

    Step into this beautifully updated 4-bedroom, 2.5-bathroom home, just a short stroll from the vibrant shops, dining, and charm of downtown Chappaqua. Perfectly situated for an easy city commute, this home offers the ideal blend of convenience and tranquility. Inside, you'll find generously sized rooms filled with natural light. The serene primary suite provides a peaceful retreat at the end of

    Vanessa Catalano Julia B Fee Sothebys Int. Rlty

    21 Kipp St, Chappaqua, NY 10514
  • 66 Kerry Ln, 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
  • 37 Hollow Oak Rd, Chappaqua, NY 10514
    37 Hollow Oak Rd, Chappaqua, NY 10514
    37 Hollow Oak Rd, Chappaqua, NY 10514
    /31

    $799,000 Pending

    • 4 Beds
    • 2 Baths
    • 1,420 Sq Ft

    37 Hollow Oak Rd, Chappaqua, NY 10514

    Charming and lovingly maintained cape cod home on beautiful private property. Located in the sought after Chappaqua Ridge neighborhood ,this home offers town water, sewer and natural gas, and is minutes to town, train and schools. The first floor features an open kitchen/dining/ living room plus 2 bedrooms and a bath. One of the bedrooms could also be used as a home office. There are sliders out

    Lauren Goldenberg William Raveis Real Estate

    37 Hollow Oak Rd, Chappaqua, NY 10514
  • 6 Seymour Place E, Armonk, NY 10504

    $3,600,000 Sold Jun 23, 2025

    • 6,074 Sq Ft
    • $593/SF
    • 17 Days On Market
    • 6 Beds
    • 6.5 Baths
    • Built 2016

    6 Seymour Place E, Armonk, NY 10504

    Discover this exceptional, better-than-new custom-built young colonial in the sought-after Yale Farms neighborhood of Armonk. Nestled on a serene cul-de-sac, this stunning residence sits on two flat, fenced acres, featuring a custom-built grilling center and bluestone patio. Truly, the perfect outdoor living space. This sophisticated 6-bedroom home showcases the finest materials, custom finishes,

    Amy Singer Houlihan Lawrence Inc.

    6 Seymour Place E, Armonk, NY 10504
  • 8 Alder Way, Armonk, NY 10504
    8 Alder Way, Armonk, NY 10504
    8 Alder Way, Armonk, NY 10504
    /34

    $1,150,000 Pending

    • 3 Beds
    • 2.5 Baths
    • 2,022 Sq Ft

    8 Alder Way, Armonk, NY 10504

    Welcome to 8 Alder Way – Turn-Key Townhouse Living in Whippoorwill RidgeThis beautifully maintained 3-bedroom, 2.5-bath Dover model is located in the sought-after gated community of Whippoorwill Ridge, just moments from downtown Armonk’s shops, dining, parks, and library. Enjoy a low-maintenance lifestyle with resort-style amenities including a community pool, tennis and pickleball

    James Schunk Schunk Realty Group

    8 Alder Way, Armonk, NY 10504
  • 8 Dewitt Dr Unit 66, 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
  • 4 Oak Hill Rd, Chappaqua, NY 10514
    4 Oak Hill Rd, Chappaqua, NY 10514
    4 Oak Hill Rd, Chappaqua, NY 10514
    /33

    $1,099,000 Pending

    • 3 Beds
    • 2.5 Baths
    • 2,195 Sq Ft

    4 Oak Hill Rd, Chappaqua, NY 10514

    Enjoy easy living in this fully renovated Cape Cod style home situated on a park-like, flat property. Located walking distance to town and train, this 3 bedroom/2.5 bathroom residence offers modern luxuries in a classic country-feeling home. Enter this home through an inviting foyer flanked by a front-to-back living room, featuring a wood-burning fireplace and a formal dining

    Allison Tintenfass Compass Greater NY, LLC

    4 Oak Hill Rd, Chappaqua, NY 10514
  • 12 Hillcrest Ave, Pleasantville, NY 10570

    $850,000 Sold Jun 20, 2025

    • 1,850 Sq Ft
    • $459/SF
    • 14 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 2002

    12 Hillcrest Ave, Pleasantville, NY 10570

    You will wake up every morning to the tree top views of the Village of Pleasantville and beyond. The morning sun will reflect breathtaking panoramic views of everything this village has to offer! The western sky lights up with hypnotic shades of purple and orange above the deck. This special Townhouse offers the lifestyle you have been searching for...privacy, stunning views, the walkability

    Loretta Fleming Chiavetta Coldwell Banker Realty

    12 Hillcrest Ave, Pleasantville, NY 10570
  • 7 Lakeside Dr, Valhalla, NY 10595
    7 Lakeside Dr, Valhalla, NY 10595
    7 Lakeside Dr, Valhalla, NY 10595
    /49

    $799,001 Pending

    • 3 Beds
    • 2.5 Baths
    • 1,850 Sq Ft

    7 Lakeside Dr, Valhalla, NY 10595

    Commuter’s Dream in the Heart of Valhalla!Beautifully maintained 3-bedroom, 2.5-bath single-family home offering the perfect blend of suburban charm and exceptional convenience. Located just blocks from the Kensico Dam and Valhalla train station, this home is ideal for commuters seeking a vibrant community lifestyle. The main level features an inviting living room, dining area, powder room,

    Cynthia Leite ERA Insite Realty Services

    7 Lakeside Dr, Valhalla, NY 10595
  • 64 Stornowaye St, Chappaqua, NY 10514

    $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
  • 21 Sterling Rd S, Armonk, NY 10504
    21 Sterling Rd S, Armonk, NY 10504
    21 Sterling Rd S, Armonk, NY 10504
    /37

    $6,950,000 Pending

    • 6 Beds
    • 9 Baths
    • 11,615 Sq Ft

    21 Sterling Rd S, Armonk, NY 10504

    Where design meets purpose—this award-winning home brings together architectural innovation and serene luxury. Created by Carol Kurth Architecture and built by Legacy Construction NE, exceptional craftsmanship is seen throughout the home, showcased by a mix of natural materials and bold structural details. A cantilevered fireplace, floating staircases and cathedral ceilings are some of the

    Brian Milton Compass Greater NY, LLC

    21 Sterling Rd S, Armonk, NY 10504
  • 24 Spring St, Pleasantville, NY 10570

    $975,000 Sold Jun 20, 2025

    • 2,019 Sq Ft
    • $483/SF
    • 18 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1932

    24 Spring St, Pleasantville, NY 10570

    Welcome to Pleasantville! This delightful Village Colonial offers a perfect blend of comfort and convenience. With its inviting front porch and beautiful perennial gardens, and curb appeal from the moment you arrive. Inside, you will find bright, airy spaces with hardwood floors throughout and a seamless flow between rooms.The kitchen with ample storage and counter space, making meal prep a

    SONIA FORCHETTI Julia B Fee Sothebys Int. Rlty

    24 Spring St, Pleasantville, NY 10570
  • 98 Westlake Dr, Valhalla, NY 10595
    98 Westlake Dr, Valhalla, NY 10595
    98 Westlake Dr, Valhalla, NY 10595
    /49

    $579,000 Pending

    • 4 Beds
    • 2 Baths
    • 1,688 Sq Ft

    98 Westlake Dr, Valhalla, NY 10595

    Welcome to this charming Valhalla home, set on a scenic and tranquil lot that offers both character and comfort. From the moment you step into the enclosed front porch, you’ll feel the warmth and timeless charm this property exudes. The inviting living room is filled with natural light thanks to an abundance of windows, creating a bright and airy space to relax or entertain. A generous dining

    Matthew Valvano Berkshire Hathaway HS NY Prop

    98 Westlake Dr, Valhalla, NY 10595
  • 11 Boulder Trail, Chappaqua, NY 10514

    $2,450,000 Sold Jun 20, 2025

    • 6,495 Sq Ft
    • $377/SF
    • 46 Days On Market
    • 5 Beds
    • 4.5 Baths
    • Built 1995

    11 Boulder Trail, Chappaqua, NY 10514

    Spectacular 5-bedroom, 4 1/2 bath, 6,495 sq ft Colonial, located in the sought after Hardscrabble Lake neighborhood within the renowned Chappaqua School District. This home features a spacious, sun drenched open floor plan accented by large rooms, high ceilings, refined hardwood floors, walls of windows, and exquisite detailing throughout. As one enters, the expansive cathedral ceiling front

    Cindy Glynn Compass Greater NY, LLC

    11 Boulder Trail, Chappaqua, NY 10514
  • 70 Manville Rd Unit 1, Pleasantville, NY 10570
    70 Manville Rd Unit 1, Pleasantville, NY 10570
    70 Manville Rd Unit 1, Pleasantville, NY 10570
    /19

    $245,000 Pending

    • 1 Bed
    • 1 Bath
    • 720 Sq Ft

    70 Manville Rd Unit 1, Pleasantville, NY 10570

    Welcome to this beautifully updated first-floor 1-bedroom, 1-bathroom unit in the sought-after Ledgerock Gardens co-op community. Featuring a modern open floor plan with a seamless flow between living, dining, and kitchen areas, this home offers both comfort and style. Enjoy the convenience of being just a short distance from Pleasantville Village’s charming restaurants, shops, public library,

    Rita Longo Howard Hanna Rand Realty

    70 Manville Rd Unit 1, Pleasantville, NY 10570
  • 385 Lake Shore Dr, Pleasantville, NY 10570

    $950,000 Sold Jun 19, 2025

    • 2,048 Sq Ft
    • $464/SF
    • 2 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1960

    385 Lake Shore Dr, Pleasantville, NY 10570

    Welcome to your serene retreat at 385 Lake Shore Drive in Pleasantville.Tucked away on a quiet cul-de-sac in a peaceful neighborhood with a scenic all-seasons lake, this beautifully maintained 4-bedroom, 2-bathroom ranch, surrounded by woods, offers comfortable, one-level living in a stunning natural setting. The open-concept layout features a spacious eat-in kitchen, dining, and living area that

    Natalia Wixom Compass Greater NY, LLC

    385 Lake Shore Dr, Pleasantville, NY 10570
  • 24 Burnsdale Ave, Valhalla, NY 10595
    24 Burnsdale Ave, Valhalla, NY 10595
    24 Burnsdale Ave, Valhalla, NY 10595
    /26

    $649,000 Pending

    • 3 Beds
    • 2 Baths
    • 2,154 Sq Ft

    24 Burnsdale Ave, Valhalla, NY 10595

    Charming and unique Colonial home featuring a welcoming living room, a spacious country kitchen perfect for gatherings and a convenient first-floor bedroom and full bathroom. The second floor offers two additional bedrooms and a full hall bathroom. The lower level boasts a large great room with a woodburning stone fireplace, full bathroom and direct outdoor access, along with a laundry area and

    Rita Longo Howard Hanna Rand Realty

    24 Burnsdale Ave, Valhalla, NY 10595
  • 353 Lake Shore Dr, Pleasantville, NY 10570

    $900,000 Sold Jun 19, 2025

    • 1,618 Sq Ft
    • $556/SF
    • 15 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1964

    353 Lake Shore Dr, Pleasantville, NY 10570

    Discover picturesque, all-season views living in this contemporary raised ranch home on a quiet cul-de-sac street. With high cathedral ceilings and large windows opening to a wraparound deck, the connection to nature is seamless, offering an ideal setting for relaxation, entertaining, and work.Enter just a few steps to the spacious open eat-in kitchen and living room with panoramic lake views.

    Natalia Wixom Compass Greater NY, LLC

    353 Lake Shore Dr, Pleasantville, NY 10570
  • 43 Whippoorwill Rd E, Armonk, NY 10504
    43 Whippoorwill Rd E, Armonk, NY 10504
    43 Whippoorwill Rd E, Armonk, NY 10504
    /29

    $1,225,000 Pending

    • 3 Beds
    • 2.5 Baths
    • 2,223 Sq Ft

    43 Whippoorwill Rd E, Armonk, NY 10504

    Beautifully remodeled Ranch-style home on a private, level property just a short walk to downtown Armonk, NY. A covered front porch with durable Trex decking welcomes you into a bright open layout, thoughtfully designed with hardwood floors, crown molding, custom trim, and recessed lighting throughout. The main living area includes a dining and living room with an electric fireplace and opens to

    Edward Holmes William Raveis-New York, LLC

    43 Whippoorwill Rd E, Armonk, NY 10504
  • 24 Manville Ln Unit 4, Pleasantville, NY 10570

    $888,888 Sold Jun 19, 2025

    • 1,627 Sq Ft
    • $546/SF
    • 13 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1977

    24 Manville Ln Unit 4, Pleasantville, NY 10570

    Beautiful Foxwood Condominium.. Picturesque Country Setting with Meticulously Kept Grounds.. Absolutely Stunning Renovation of a Rarely Offered " Westminster " Model Townhome in a Great Location at the Highest Elevation in Foxwood.. Fabulous Kitchen with an Abundance of Cabinetry and Island Accommodating Stool Seating, Storage Built in's and Pantry, Quartzite Counters, Tile Backsplash, Stainless

    Vincent Vetrano Douglas Elliman Real Estate

    24 Manville Ln Unit 4, Pleasantville, NY 10570
  • 13 Colonial Ln, Valhalla, NY 10595
    13 Colonial Ln, Valhalla, NY 10595
    13 Colonial Ln, Valhalla, NY 10595
    /20

    $975,000 Pending

    • 4 Beds
    • 2.5 Baths
    • 2,028 Sq Ft

    13 Colonial Ln, Valhalla, NY 10595

    Welcome to 13 Colonial Lane...A charming and meticulously maintained Colonial on a picturesque cul-de-sac in Valhalla. This prime lot on sought-after street has a beautifully manicured property which offers serene surroundings. This 4 Bedroom-2.5 Bath home boasts modern finishes throughout which includes hardwood floors on both levels and central air. Spacious living room, formal dining room,

    Gregory McCarthy Houlihan Lawrence Inc.

    13 Colonial Ln, Valhalla, NY 10595
  • 105 Lake St, Pleasantville, NY 10570

    $881,230 Sold Jun 19, 2025

    • 1,762 Sq Ft
    • $500/SF
    • 34 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1920

    105 Lake St, Pleasantville, NY 10570

    A/O continue to showWelcome to CLUB 105 A Home Like No Other!Nestled in the heart of Pleasantville, "CLUB 105" is more than just a home, it's a lifestyle. This charming Cape-style residence at 105 Lake Street offers a covered front porch, oversized driveway, formal living and dining rooms, chef's kitchen with breakfast bar, four bedrooms, two full bathrooms, and a two-car garage, perfectly

    Clayton Livingston McGrath Realty Inc

    105 Lake St, Pleasantville, NY 10570
  • 31 Lawrence Dr Unit D, White Plains, NY 10603
    31 Lawrence Dr Unit D, White Plains, NY 10603
    31 Lawrence Dr Unit D, White Plains, NY 10603
    /38

    $260,000 Pending

    • 2 Beds
    • 1 Bath
    • 830 Sq Ft

    31 Lawrence Dr Unit D, White Plains, NY 10603

    Turnkey & Stylish 2-Bedroom Co-op!A fully renovated 830 sq. ft. 2-bedroom co-op that checks every box. This sun-drenched home features brand new hardwood floors, sleek recessed lighting, and an updated modern bathroom. The kitchen is a chef’s dream, outfitted with brand new stainless steel appliances, ample cabinet space, and a clean, contemporary aesthetic.Perfectly positioned

    Natasha Owens Keller Williams NY Realty

    31 Lawrence Dr Unit D, White Plains, NY 10603
  • 20 Lochland Rd, Valhalla, NY 10595

    $850,000 Sold Jun 18, 2025

    • 2,033 Sq Ft
    • $418/SF
    • 13 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1942

    20 Lochland Rd, Valhalla, NY 10595

    Early AO, 4/16, CTS.Welcome to this beautifully expanded Cape, where warmth and charm greet you at every turn. Nestled in the highly sought-after Westlake area, this move-in-ready home offers both privacy and convenience, with a level yard surrounded by lush ever-green trees and hedges.As you step inside, the original hardwood floors guide you through the welcoming living spaces. Archways lead

    Jeanne Beckley Howard Hanna Rand Realty

    20 Lochland Rd, Valhalla, NY 10595
  • 263 Memorial Dr, Hawthorne, NY 10532
    263 Memorial Dr, Hawthorne, NY 10532
    263 Memorial Dr, Hawthorne, NY 10532
    /34

    $699,999 Pending

    • 4 Beds
    • 2 Baths
    • 1,776 Sq Ft

    263 Memorial Dr, Hawthorne, NY 10532

    Welcome home to 263 Memorial Drive, a delightful 4-bedroom, 2-bathroom ranch nestled on a generous quarter-acre lot in the heart of Hawthorne. This inviting residence offers comfortable single-level living with hardwood floors throughout the main level leading you to spacious bedrooms bathed in natural light. The home features a private primary bathroom, offering convenience and comfort, central

    Christine Ricci Keller Williams NY Realty

    263 Memorial Dr, Hawthorne, NY 10532

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