Westchester, NY Homes

• 

  Est $1,388,151 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 2,688 Sq Ft

  25 Meadow Ln, Chappaqua, NY 10514

  25 Meadow Ln, Chappaqua, NY 10514
• 

  

  

  /22

  $1,099,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,212 Sq Ft

  5 Crossways, Chappaqua, NY 10514

  Move right into this walk-to-town beautifully updated 4-bedroom, 2.5-bath Colonial that offers the perfect balance of classic charm and modern convenience. Just steps from the heart of Chappaqua, this home features an open-concept layout and flexible spaces ideal for everyday living and effortless entertaining.Step through the storybook Dutch door to a light-filled, double-height entry with a

  Jill Urban Compass Greater NY, LLC

  5 Crossways, Chappaqua, NY 10514
• 

  $1,589,000 Sold May 28, 2025

  • 3,041 Sq Ft
  • $523/SF
  • 26 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1955

  395 Bedford Rd, Chappaqua, NY 10514

  An impressive and tastefully appointed five bedroom colonial home in the much sought after Chappaqua School District. Set on just over one beautiful acre of level land, this impressive home offers the perfect blend of tranquility and convenience, with easy access to the Chappaqua train station. The heart of the home is the spacious, airy, sun-filled family room, featuring a wall of full length

  Catherine O'Connor Houlihan Lawrence Inc.

  395 Bedford Rd, Chappaqua, NY 10514
• 

  Est $1,419,594 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,022 Sq Ft

  10 Birch Ln, Chappaqua, NY 10514

  10 Birch Ln, Chappaqua, NY 10514
• 

  

  

  /33

  $999,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,824 Sq Ft

  8 Elizabeth St, Chappaqua, NY 10514

  Welcome to 8 Elizabeth Street – A Charming, Turnkey Colonial nestled on a quiet cul-de-sac street. A beautifully updated three-bedroom, two-and-a-half-bathroom Colonial that seamlessly blends style, comfort, and convenience. Step inside to discover a thoughtfully designed layout, where large, updated windows flood the home with natural light. The spacious living room is an inviting gathering

  Jennifer Harris Compass Greater NY, LLC

  8 Elizabeth St, Chappaqua, NY 10514
• 

  $2,100,000 Sold May 23, 2025

  • 4,446 Sq Ft
  • $472/SF
  • 8 Days On Market

  • 5 Beds
  • 5 Baths
  • Built 1969

  28 James Rd, Mount Kisco, NY 10549

  Perched perfectly on 2 acres with a private and level backyard in the Chappaqua school district. This stunning colonial home offers 5 bedrooms, 5 full bathrooms, and over 4,400 sq ft of living space. Step inside the spacious entry hall to find a sunlit open floor plan with distinctive finishes and hardwood floors. The chef’s kitchen, featuring a skylight over the large center island, and Viking

  Edward Holmes William Raveis-New York, LLC

  28 James Rd, Mount Kisco, NY 10549
• 

  Est $1,076,810 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,355 Sq Ft

  30 Meadow Ln, Chappaqua, NY 10514

  30 Meadow Ln, Chappaqua, NY 10514
• 

  

  /5

  $1,599,995 Pending

  • 3 Beds
  • 3.5 Baths
  • 3,353 Sq Ft

  15 Wallace Way Unit 20, Chappaqua, NY 10514

  TO BE BUILT. Move-in Spring 2026. Spacious 3485 square feet ! Still time to personalize interior finishes by visiting our luxurious Design Studio. As you enter the Millwood Elite, the exquisite foyer presents sweeping views of this home's open-concept floor plan and luxurious finishes. A large center island in the kitchen overlooks the casual dining area. The great room is the perfect setting

  Andrea Martone Houlihan Lawrence Inc.

  15 Wallace Way Unit 20, 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
• 

  Est $2,375,846 Not Listed For Sale

  • 4 Beds
  • 6 Baths
  • 5,920 Sq Ft

  36 Gray Rock Ln, Chappaqua, NY 10514

  36 Gray Rock Ln, Chappaqua, NY 10514
• 

  

  /29

  $879,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,334 Sq Ft

  180 Millwood Rd, Chappaqua, NY 10514

  Welcome to a home full of warmth, charm, and everyday comfort — perfectly situated right across from beautiful Gedney Park and just around the corner from the elementary school.This inviting 4-bedroom, 2.5-bathroom home has everything you need for easy, relaxed living. Step inside to a bright and welcoming living room, a private office ideal for working from home, and a comfortable family

  Danae Richards William Raveis-New York, LLC

  180 Millwood Rd, Chappaqua, NY 10514
• 

  $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
• 

  Est $1,388,815 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,736 Sq Ft

  71 Oak Hill Rd, Chappaqua, NY 10514

  71 Oak Hill Rd, Chappaqua, NY 10514
• 

  

  /27

  $1,695,000 Pending

  • 5 Beds
  • 3 Baths
  • 3,192 Sq Ft

  19 Brandon Dr, Mount Kisco, NY 10549

  Welcome to this beautifully renovated, sun-filled 5-bedroom, 3-bathroom home in the award-winning Chappaqua School District. Set on 1.54 acres, this home features a seamless open-concept layout ideal for everyday living and entertaining. The bright and well-appointed kitchen is a true highlight that features an expansive island, stainless steel appliances, and ample storage space. The kitchen

  Amy Ensign Julia B Fee Sothebys Int. Rlty

  19 Brandon Dr, Mount Kisco, NY 10549
• 

  $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
• 

  Est $1,279,577 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,275 Sq Ft

  29 Deepwood Dr, Chappaqua, NY 10514

  29 Deepwood Dr, Chappaqua, NY 10514
• 

  

  /47

  $2,275,000 Pending

  • 5 Beds
  • 5.5 Baths
  • 7,412 Sq Ft

  25 Cardinal Place, Mount Kisco, NY 10549

  Graciously set on park-like property behind a gated circular drive at the end of a cul-de-sac in one of Chappaqua's premiere neighborhoods, this stunning 5+ bedroom colonial on 3 lovely park-like acres is move-in ready and offers an open floorplan. A covered porch leads to an expansive entry hall with powder room, a large formal living room with 3 exposures, adjacent to an inviting formal dining

  Sena Baron William Raveis-New York, LLC

  25 Cardinal Place, Mount Kisco, NY 10549
• 

  $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
• 

  Est $1,747,607 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 4,459 Sq Ft

  15 North Way, Chappaqua, NY 10514

  15 North Way, Chappaqua, NY 10514
• 

  

  /4

  $1,399,995 Pending

  • 2 Beds
  • 3.5 Baths
  • 2,945 Sq Ft

  13 Wallace Way Unit 19 Briarcliff Tradit, Chappaqua, NY 10514

  2 BR Primary on first floor home. Large Eat in kitchen with island, open to great room and dining room. Second floor office and wet bar makes entertaining easy on rooftop terrace with built-in kitchen BBQ. Lower level is finished with media room and full bath.

  Thomas Jacovino Toll Brothers Real Estate Inc.

  13 Wallace Way Unit 19 Briarcliff Tradit, 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
• 

  Est $2,421,594 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 3,775 Sq Ft

  28 North Way, Chappaqua, NY 10514

  28 North Way, Chappaqua, NY 10514
• 

  

  /7

  $990,000 Pending

  • Land
  • 12 Acres
  • $82,652 per Acre

  115 Old Roaring Brook Rd, Mount Kisco, NY 10549

  Open lawns and stone walls encompass this vacant property on coveted Old Roaring Brook Road offering a uniqueopportunity to create and custom build your dream home. Gated sweeping drive to private setting. The mature trees and natural gardens present a peaceful and serene environment. The existing parcel is presently a blank canvas of nature and tranquility totaling almost 12 acres. Distant

  Susan Stillman Houlihan Lawrence Inc.

  115 Old Roaring Brook Rd, Mount Kisco, NY 10549
• 

  $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
• 

  Est $1,597,269 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,046 Sq Ft

  18 West Way, Chappaqua, NY 10514

  18 West Way, Chappaqua, NY 10514
• 

  

  /26

  $989,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,018 Sq Ft

  74 Seven Bridges Rd, Chappaqua, NY 10514

  Welcome to 74 Seven Bridges Road in Chappaqua—a home that perfectly blends comfort and style.This inviting home features an open floor plan designed for effortless living and entertaining. Enter into a large foyer with a smart mud room tucked away to the side. Here you also have direct and easy access to the garage. Once inside you will appreciate the warmth and sophistication this home

  Joanna Rizoulis Julia B Fee Sothebys Int. Rlty

  74 Seven Bridges Rd, Chappaqua, NY 10514
• 

  $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
• 

  Est $1,402,746 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,763 Sq Ft

  34 Shady Ln, Chappaqua, NY 10514

  34 Shady Ln, Chappaqua, NY 10514
• 

  

  /4

  $1,338,995 Pending

  • 2 Beds
  • 2.5 Baths
  • 2,503 Sq Ft

  14 Carriage Ln Unit 87, Chappaqua, NY 10514

  HOME IS UNDER CONSTRUCTION- READY FOR Summer 2025 closing 2 BR Briarcliff Floorplan with primary on first floor. You can still add structural and design features to this home. This outstanding home is located in a great location facing greenspace on one side and forest views from the rooftop deck. It is located in the heart of the neighborhood where you can walk to shopping, cafes,

  Thomas Jacovino Toll Brothers Real Estate Inc.

  14 Carriage Ln Unit 87, Chappaqua, NY 10514
• 

  $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
• 

  Est $1,616,281 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,827 Sq Ft

  67 Cross Ridge Rd, Chappaqua, NY 10514

  67 Cross Ridge Rd, Chappaqua, NY 10514
• 

  

  /5

  $1,480,995 Pending

  • 2 Beds
  • 3.5 Baths
  • 2,945 Sq Ft

  14 Carriage Ln Unit 87, Chappaqua, NY 10514

  HOME IS UNDER CONSTRUCTION- READY FOR FALL 2025 2 BR Briarcliff Floorplan with primary on first floor. A finished basement with full bath give plenty of room for everyone to enjoy. This outstanding home is located in a great location facing greenspace on one side and forest views from the rooftop deck. It is located in the heart of the neighborhood where you can walk to shopping,

  Thomas Jacovino Toll Brothers Real Estate Inc.

  14 Carriage Ln Unit 87, 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
• 

  Est $3,028,910 Not Listed For Sale

  • 6 Beds
  • 5.5 Baths
  • 8,000 Sq Ft

  10 Nancy Ln, Chappaqua, NY 10514

  10 Nancy Ln, 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
• 

  Est $1,860,151 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 4,898 Sq Ft

  66 Mountain Peak Rd, Chappaqua, NY 10514

  66 Mountain Peak Rd, Chappaqua, NY 10514
• 

  $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
• 

  Est $1,433,821 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,919 Sq Ft

  6 Cindy Way, Chappaqua, NY 10514

  6 Cindy Way, 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
• 

  Est $1,432,927 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,550 Sq Ft

  385 Quaker Rd, Chappaqua, NY 10514

  385 Quaker Rd, Chappaqua, NY 10514

Showing Results 241 - 280, Page 7 of 18