6,508

Westchester, NY Homes

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  • /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
  • 2 South Place, Chappaqua, NY 10514

    $1,450,000 Sold May 22, 2025

    • 2,233 Sq Ft
    • $649/SF
    • 9 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1936

    2 South Place, Chappaqua, NY 10514

    Welcome to 2 South Place - A stylish family home in the desirable Hillholme Community of Chappaqua, within the Chappaqua School District. This residence blends an integration of classic traditional and modern design offering elegant living spaces and a prime location. First level includes a Classic living room with fireplace, recess lighting, formal dinning room, recess lighting. Gourmet

    Toni DiMichelo Houlihan Lawrence Inc.

    2 South Place, 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
  • 2 Highview Rd, Ossining, NY 10562

    $902,500 Sold May 19, 2025

    • 2,719 Sq Ft
    • $332/SF
    • 12 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1956

    2 Highview Rd, Ossining, NY 10562

    Nestled on a picturesque 1-acre corner lot in New Castle, this exquisite sprawling split ranch seamlessly blends comfort with sophistication. Designed for effortless entertaining, it boasts an expansive great room with soaring ceilings, skylights, and a charming wood-burning fireplace. The gourmet eat-in kitchen showcases newly installed quartzite countertops, a sleek cooktop, a wall oven with a

    Lisa Cozzi Westchester Dream Home Realty

    2 Highview Rd, Ossining, NY 10562
  • /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
  • 16 Glenwood Rd, Millwood, NY 10546

    $960,000 Sold May 16, 2025

    • 2,014 Sq Ft
    • $477/SF
    • 13 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1957

    16 Glenwood Rd, Millwood, NY 10546

    Located on a bucolic, tree-lined street in Millwood, NY is this exquisite split-level 3 bedroom, 3 full bath home on level property. Situated in the highly regarded Chappaqua school district, it combines comfort, style, and the luxuries often found in larger homes. It is in a prime location, steps from the North County Trailway and conveniently located near Millwood’s DeCicco’s supermarket,

    Wendy Nolan Houlihan Lawrence Inc.

    16 Glenwood Rd, Millwood, NY 10546
  • /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
  • 3 Dewitt Dr Unit 77, Chappaqua, NY 10514

    $1,715,408 Sold May 16, 2025

    • 3,269 Sq Ft
    • $525/SF
    • 39 Days On Market
    • 2 Beds
    • 3.5 Baths
    • Built 2024

    3 Dewitt Dr Unit 77, Chappaqua, NY 10514

    HOME IS TO BE BUILT. 2 BR very popular Greeley Floorplan with primary on first floor. We have a model of this home to walk through. It is ideally sized at 3,269 sq. ft. and includes 2 BR + office, huge loft, finished basement with media room and full bath. The 2-story open concept great room and kitchen allow for large family gatherings. The open island with ample seating beckons your inner

    Thomas Jacovino Toll Brothers Real Estate Inc.

    3 Dewitt Dr Unit 77, 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
  • 7 Dewitt Dr Unit 79, Chappaqua, NY 10514

    $1,519,995 Sold May 16, 2025

    • 3,614 Sq Ft
    • $421/SF
    • 354 Days On Market
    • 2 Beds
    • 3.5 Baths
    • Built 2025

    7 Dewitt Dr Unit 79, Chappaqua, NY 10514

    HOME ALMOST COMPLETED- SPRING 2025 CLOSE! Byram Farmhouse. Designer features already selected.Home includes a finished basement with full bath, media room and may more upgrades. The open concept great room and kitchen allow for large family gatherings. The open island with ample seating beckons your inner chief to come alive. A roaring fireplace will warm the entire home. A private rooftop

    Thomas Jacovino Toll Brothers Real Estate Inc.

    7 Dewitt Dr Unit 79, 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
  • 6 Carriage Hill Rd, Ossining, NY 10562

    $720,000 Sold May 15, 2025

    • 2,518 Sq Ft
    • $286/SF
    • 40 Days On Market
    • 5 Beds
    • 2.5 Baths
    • Built 1967

    6 Carriage Hill Rd, Ossining, NY 10562

    Spacious Colonial Home on Over 1 Acre of Flat, Private LandNestled on a serene, quiet lot of over an acre, this expansive colonial offers over 2,500 square feet of living space, featuring 5 generously sized bedrooms and 2.5 baths. Enjoy peace of mind with well-maintained mechanicals, including a brand-new oil burner, recently updated central AC, and upgraded electrical panel. The home boasts a

    Louis Bove HomeSmart Premier Living Rlty

    6 Carriage Hill Rd, Ossining, NY 10562
  • /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
  • 109 Cross River Rd Unit 109, Mount Kisco, NY 10549

    $1,435,000 Sold May 14, 2025

    • 3,346 Sq Ft
    • $429/SF
    • 12 Days On Market
    • 2 Beds
    • 3.5 Baths
    • Built 1996

    109 Cross River Rd Unit 109, Mount Kisco, NY 10549

    Beauty abounds in and around this pristine, airy sun-filled Hudson model in sought-after Riverwoods. Oversized windows offerpicturesque views from front to back and give one a feeling of being outside while inside. A floating center staircase reaches anopen loft area overlooking the foyer affording an open feel. Lower level offers a guest suite, full bath and entertainment areawith French doors

    Catherine O'Connor Houlihan Lawrence Inc.

    109 Cross River Rd Unit 109, Mount Kisco, NY 10549
  • /9

    $1,699,000 Pending

    • 2 Beds
    • 3.5 Baths
    • 3,269 Sq Ft

    8 Carriage Ln Unit 84, Chappaqua, NY 10514

    Home Under construction a spacious 3269’ ! Move-in by Summer 2025' As you enter the Greeley Newhaven, the exquisite foyer presents sweeping views of this home's open-concept floor plan and luxurious finishes. The spacious kitchen and great room provide the ideal space for entertaining. The casual dining area provides the perfect space for entertaining guests with easy access to the kitchen. The

    Andrea Martone Houlihan Lawrence Inc.

    8 Carriage Ln Unit 84, Chappaqua, NY 10514
  • 7 High Meadows Rd, Mount Kisco, NY 10549

    $1,820,000 Sold May 14, 2025

    • 4,776 Sq Ft
    • $381/SF
    • 11 Days On Market
    • 4 Beds
    • 4.5 Baths
    • Built 1987

    7 High Meadows Rd, Mount Kisco, NY 10549

    Dramatic contemporary residence with modern styling, soaring ceilings, gallery-like spaces, and spacious accommodations all set on a verdant, landscaped acre within the Chappaqua school district. A strikingly bold double door leads to an open entry foyer. Living room with vaulted ceiling, wood-burning fireplace & hardwood flooring. Elegant, banquet-sized dining room with built-ins, accent

    Stacy Levey William Raveis-New York, LLC

    7 High Meadows Rd, Mount Kisco, NY 10549
  • /31

    $1,200,000 Pending

    • 3 Beds
    • 2.5 Baths
    • 2,000 Sq Ft

    29 Begg Dr, Chappaqua, NY 10514

    Welcome to 29 Begg Drive, a meticulously-maintained gem in Chappaqua! This serene property features an open floor plan with hardwood floors, charming traditional architectural features, and numerous upgrades. The sunlit first floor features a kitchen with a large picture window, a living room area, and a dining area. An attached screened-in porch, which overlooks the yard and connects to a large

    Wendy Nolan Houlihan Lawrence Inc.

    29 Begg Dr, Chappaqua, NY 10514
  • 72 Carolyn Place, Chappaqua, NY 10514

    $3,375,000 Sold May 14, 2025

    • 8,291 Sq Ft
    • $407/SF
    • 140 Days On Market
    • 4 Beds
    • 8 Baths
    • Built 2000

    72 Carolyn Place, Chappaqua, NY 10514

    Elegant and sophisticated, shingle style Colonial sited on 3.46 acres of level, idyllic, private property in one of Chappaqua's most coveted neighborhoods. A private, gated drive introduces this 5 bedroom, 8,000+sq ft home, built by the renowned McKenna Associates, known for quality construction and meticulous workmanship. Designed with luxury finishes and amenities, this home combines both

    Cindy Glynn Compass Greater NY, LLC

    72 Carolyn Place, Chappaqua, NY 10514
  • /42

    $2,588,000 Pending

    • 4 Beds
    • 4.5 Baths
    • 6,612 Sq Ft

    177 Somerstown Rd, Millwood, NY 10546

    California dreaming’ but East Coast leaning? You can catch the bi-coastal wave in this masterfully built & deliciously designed modern home which at once combines Santa Monica & Scandinavia. Glass, steel, cement & brick both gird & grace this built to stand for centuries place. Why settle for a house that settles? Wood-Free construction provides worry-free living & that peace of mind is

    Owen Berkowitz Christie's Int. Real Estate

    177 Somerstown Rd, Millwood, NY 10546
  • 3 Bradley Farms, Chappaqua, NY 10514

    $2,700,000 Sold May 09, 2025

    • 5,947 Sq Ft
    • $454/SF
    • 15 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1947

    3 Bradley Farms, Chappaqua, NY 10514

    Exquisite Bradley Farms Colonial: A Perfect Blend of Timeless Elegance and Modern Comfort. Discover the charm of this beautifully updated home, perfectly positioned on a coveted cul-de-sac. This exceptional residence masterfully combines timeless style with modern amenities, creating an inviting sanctuary for discerning buyers.Step inside to find a thoughtfully designed interior, featuring

    Amrita Singh William Raveis-New York, LLC

    3 Bradley Farms, Chappaqua, NY 10514
  • /48

    $1,459,000 Pending

    • 2 Beds
    • 3.5 Baths
    • 3,914 Sq Ft

    144 Burr Farms Rd, Mount Kisco, NY 10549

    Welcome to 144 Burr Farms Road! Nestled at the end of one of Riverwoods’ most expansive driveways and framed by a beautifully manicured front lawn with specimen plantings, this home is a rare find. Privately tucked into one of the most serene corners of this sought-after community—and bordering striking rock outcroppings and a protected nature preserve—this location offers the perfect blend of

    Catherine O'Connor Houlihan Lawrence Inc.

    144 Burr Farms Rd, Mount Kisco, NY 10549
  • 13 Main St, Mount Kisco, NY 10549

    $650,000 Sold May 09, 2025

    • 1,058 Sq Ft
    • $614/SF
    • 27 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1925

    13 Main St, Mount Kisco, NY 10549

    Prime location!! Nestled in the wonderful Kisco Park neighborhood within the highly-rated Chappaqua school district, this classic Tudor home exudes charm and character, just waiting for your personal touch! With its beautiful architecture and abundant natural light, this home offers a warm and inviting atmosphere throughout. The spacious bedrooms boast large closets, providing plenty of storage,

    Valerie Codino Keller Williams Realty Group

    13 Main St, Mount Kisco, NY 10549
  • /49

    $1,200,000 Pending

    • 4 Beds
    • 2 Baths
    • 1,874 Sq Ft

    83 Inningwood Rd, Millwood, NY 10546

    Newly staged and a pleasure to show! Perched gracefully on a hill, this striking mid-century modern home is a testament to architect Aaron Resnick’s creative vision, shaped under the mentorship of Frank Lloyd Wright. Embracing the philosophy that architecture should harmonize with its surroundings, the design flows seamlessly with the natural topography rather than imposing upon it.With all

    Amy Via Houlihan Lawrence Inc.

    83 Inningwood Rd, Millwood, NY 10546
  • 2 Cedar Ln, Chappaqua, NY 10514

    $2,201,800 Sold May 09, 2025

    • 4,462 Sq Ft
    • $493/SF
    • 35 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1963

    2 Cedar Ln, Chappaqua, NY 10514

    Welcome to 2 Cedar Lane, one of Chappaqua’s most charming and cozy capes situated on a quiet corner close to town. The home boasts over 4,400 square feet of bright and airy space, offering 5 bedrooms and 3/full 1/half bathrooms. The layout is designed for easy living with the primary bedroom + 2 bedrooms on the main floor, 2 bedrooms upstairs, and a finished lower level with ample space for

    Francie Malina Compass Greater NY, LLC

    2 Cedar Ln, Chappaqua, NY 10514
  • /40

    $650,000 Pending

    • 3 Beds
    • 2.5 Baths
    • 2,084 Sq Ft

    375 Quaker Rd, Chappaqua, NY 10514

    Vintage Village Colonial set on a pretty, .85-acre, level, corner lot landscaped with colorful seasonal blooms. Small covered front porch entry. Hardwood floors run throughout the entry foyer, the large front-facing living room with bay window, beamed ceiling and ceiling fan, and the adjoining formal dining room adorned with ornamental tin ceiling and crown and chair-rail molding. The eat-in

    Stacy Levey William Raveis-New York, LLC

    375 Quaker Rd, Chappaqua, NY 10514
  • 50 Mountain Peak Rd, Chappaqua, NY 10514

    $1,290,000 Sold May 09, 2025

    • 3,229 Sq Ft
    • $400/SF
    • 19 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1968

    50 Mountain Peak Rd, Chappaqua, NY 10514

    Expanded Cape Cod Colonial in Prime Chappaqua Location. Discover the perfect blend of privacy, convenience, and potential in this delightful 4-bedroom, 3-bath home, nestled in a sought-after Chappaqua location. Set on a fabulous private lot, this lovingly maintained property offers a rare opportunity to customize and create your dream home while enjoying modern updates and timeless character. The

    Wendy Nolan Houlihan Lawrence Inc.

    50 Mountain Peak Rd, Chappaqua, NY 10514
  • /32

    $1,890,000 Pending

    • 4 Beds
    • 5 Baths
    • 4,051 Sq Ft

    50 Kerry Ln, Chappaqua, NY 10514

    Nestled on a coveted lane in Chappaqua, this expanded 4-bedroom Colonial offers an unparalleled blend of privacy, luxury, and charm. Set on over 2 acres of meticulously landscaped grounds, this exceptional property features a stunning gunite heated saltwater pool, lush mature plantings, and a picture-perfect setting that defines upscale suburban living. Step inside to discover a beautifully

    Amy Singer Houlihan Lawrence Inc.

    50 Kerry Ln, Chappaqua, NY 10514

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