Ossining, NY Homes

• 

  $1,850,000

  Sold Jun 08, 2026

  10 Shadow Tree Ln, Briarcliff Manor, NY 10510

  • 4 Beds
  • 4.5 Baths
  • 5,399 Sq Ft
  • Built 2005

  Last Sold Summary

  • 3% Below List Price
  • $343/SF
  • 37 Days On Market

  Last Listing Agent Ellen Schwartz Julia B Fee Sothebys Int. Rlty

  10 Shadow Tree Ln, Briarcliff Manor, NY 10510
• 

  Est $730,636

  Not Listed For Sale

  55 Briarbrook Dr, Briarcliff Manor, NY 10510

  • 2 Beds
  • 2.5 Baths
  • 2,099 Sq Ft
  • Built 2001

  55 Briarbrook Dr, Briarcliff Manor, NY 10510

  Last Sold Summary

  • 34 Days On Market

  Last Listing Agent Suzan Zeolla Houlihan Lawrence Inc.
• 

  

  

  /41

  $975,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 2,889 Sq Ft

  19 Winterberry Ln, Briarcliff Manor, NY 10510

  Welcome to 19 Winterberry Lane, a beautifully maintained townhome in the highly desirable Wyndcrest community of Briarcliff Manor. Offering approximately 3,000 square feet of thoughtfully designed living space, this move-in ready home combines quality craftsmanship, generous living areas, and an exceptional location. Just a short walk to the Village, restaurants, shopping, parks, and scenic

  Suzan Zeolla Houlihan Lawrence Inc.

  19 Winterberry Ln, Briarcliff Manor, NY 10510
• 

  $625,000

  Sold Sep 02, 2025

  7 Fuller Rd, Ossining, NY 10562

  • 4 Beds
  • 2 Baths
  • 1,692 Sq Ft
  • Built 1963

  Last Sold Summary

  • 10% Above List Price
  • $369/SF
  • 18 Days On Market

  Current Estimated Value $660,212

  Last Listing Agent Amy Dmytryshyn Corcoran Legends Realty

  7 Fuller Rd, Ossining, NY 10562
• 

  Not Listed For Sale

  129 S Highland Ave Unit 2C5, Ossining, NY 10562

  • 1 Bed
  • 1 Bath
  • 750 Sq Ft
  • Built 1962

  129 S Highland Ave Unit 2C5, Ossining, NY 10562

  Last Sold Summary

  • 76 Days On Market

  Last Listing Agent Mavra Mita Howard Hanna Rand Realty
• 

  

  /39

  $1,045,000

  • 4 Beds
  • 3 Baths
  • 2,573 Sq Ft

  27 Ryder Rd, Ossining, NY 10562

  Welcome to this beautifully renovated Dutch Colonial, where timeless charm meets modern comfort and breathtaking Hudson River views create an unforgettable setting. Thoughtfully redesigned, the sun-filled chef's kitchen is the heart of the home, featuring crisp white cabinetry, expansive quartz countertops, abundant storage, and a seamless flow into the dining and living areas, perfect for

  Wendy Holt Houlihan Lawrence Inc.

  27 Ryder Rd, Ossining, NY 10562
• 

  $3,100,000

  Sold Sep 24, 2025

  41 Austin Place, Briarcliff Manor, NY 10510

  • 5 Beds
  • 7.5 Baths
  • 9,783 Sq Ft
  • Built 2007

  Last Sold Summary

  • 3% Above List Price
  • $317/SF
  • 53 Days On Market

  Current Estimated Value $3,224,924

  Last Listing Agent Hillary Landau Compass Greater NY, LLC

  41 Austin Place, Briarcliff Manor, NY 10510
• 

  Est $159,000

  Not Listed For Sale

  121 S Highland Ave Unit 3C, Ossining, NY 10562

  • 1 Bed
  • 1 Bath
  • 750 Sq Ft
  • Built 1964

  121 S Highland Ave Unit 3C, Ossining, NY 10562

  Last Sold Summary

  • 27 Days On Market

  Last Listing Agent Laura Ionata Corcoran Legends Realty
• 

  

  /26

  $899,000

  Pending

  • 4 Beds
  • 2.5 Baths
  • 2,716 Sq Ft

  5 Gualtiere Ln, Ossining, NY 10562

  Welcome to this beautiful 4 bedroom, 2 full bath, 1 half bath home offering stunning water views and views of the Hudson River and Mario M. Cuomo bridge. Thoughtfully designed with spacious living areas and inviting outdoor spaces, this home combines comfort, charm, and an exceptional setting. Step inside through the impressive two story foyer, where soaring ceilings create a bright and welcoming

  Guadalupe Mendoz Avila Semper Home Real Estate, LLC

  5 Gualtiere Ln, Ossining, NY 10562
• 

  $650,000

  Sold Oct 01, 2025

  23 Ann St, Ossining, NY 10562

  • 5 Beds
  • 2 Baths
  • 1,800 Sq Ft
  • Built 1897

  Last Sold Summary

  • $361/SF
  • 58 Days On Market

  Current Estimated Value $665,804

  Last Listing Agent Eric Schatz Schatz Realty Group

  23 Ann St, Ossining, NY 10562
• 

  Est $726,505

  Not Listed For Sale

  9 River Pkwy, Briarcliff Manor, NY 10510

  • 3 Beds
  • 2 Baths
  • 1,696 Sq Ft
  • Built 1976

  9 River Pkwy, Briarcliff Manor, NY 10510

  Last Sold Summary

  • 270 Days On Market

  Last Listing Agent Joe Hasselt Joe Hasselt Real Estate
• 

  

  /16

  $500,000

  Pending

  • 3 Beds
  • 3 Baths
  • 1,992 Sq Ft

  237 Spring St, Ossining, NY 10562

  Welcome to this beautiful triplex. Taxes do not reflect STAR. It’s a short distance to the Metro North train station and downtown Ossining with it’s restaurants, shops and Farmer’s Market. 3rd floor unit is occupied and can only be shown when the tenant is present for pre-arranged appointments.There is a cistern behind the house with stones on top of it. Please do not disturb it. The garage

  Peggy Wunderlich Douglas Elliman Real Estate

  237 Spring St, Ossining, NY 10562
• 

  $280,000

  Sold Dec 30, 2025

  129 S Highland Ave Unit C-2, Ossining, NY 10562

  • 3 Beds
  • 2 Baths
  • 1,047 Sq Ft
  • Built 1961

  Last Sold Summary

  • $267/SF
  • 91 Days On Market

  Last Listing Agent Linda Williams Century 21 Alliance Realty Grp

  129 S Highland Ave Unit C-2, Ossining, NY 10562
• 

  Not Listed For Sale

  17 Steven Dr Unit 3, Ossining, NY 10562

  • 2 Beds
  • 2.5 Baths
  • 1,710 Sq Ft
  • Built 1995

  17 Steven Dr Unit 3, Ossining, NY 10562

  Last Sold Summary

  • 21 Days On Market

  Last Listing Agent Pamela Rotando Coldwell Banker Realty
• 

  

  /34

  $1,700,000

  Pending

  • 2 Beds
  • 2 Baths
  • 1,590 Sq Ft

  1306 Grants Ln, Ossining, NY 10562

  Some homes are simply built. Others are designed to change the way you experience nature. This extraordinary 1956 residence by renowned architect David Henken, one of Frank Lloyd Wright's most celebrated apprentices, is one of those rare homes.Privately nestled on more than 17 breathtaking acres above a babbling stream near Teatown Lake Reservation, the home embodies the timeless principles

  Diana Polack Compass Greater NY, LLC

  1306 Grants Ln, Ossining, NY 10562
• 

  $999,000

  Sold Apr 24, 2026

  7 Dunn Ln, Briarcliff Manor, NY 10510

  • 3 Beds
  • 3 Baths
  • 1,800 Sq Ft
  • Built 1950

  Last Sold Summary

  • 2% Above List Price
  • $555/SF
  • 29 Days On Market

  Current Estimated Value $981,914

  Last Listing Agent Greg Kochanov Compass Greater NY, LLC

  7 Dunn Ln, Briarcliff Manor, NY 10510
• 

  Not Listed For Sale

  79 Main St, Ossining, NY 10562

  • 8 Beds
  • 4 Baths
  • 3,888 Sq Ft
  • Built 1880

  79 Main St, Ossining, NY 10562

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Arafat Ibrahim AI Realty Brokerage LLC
• 

  

  /14

  $210,000

  $93K PRICE DROP Pending

  • 2 Beds
  • 1 Bath
  • 951 Sq Ft

  135 Main St Unit 203, Ossining, NY 10562

  Fully available as f 1/7/2026. Exciting 2-bedroom condo in the Village of Ossining! Enjoy the lifestyle of convenience. Walk to train, restaurants, stores, farmers market, festivals, waterfront park, community recreation center, library, and more. Cats and dogs friendly (limit 2 per unit)! As an owner, you can obtain a parking permit for both the village and train station. This property is a part

  Igor Krasnoperov Rising Star Realty

  135 Main St Unit 203, Ossining, NY 10562
• 

  $865,000

  Sold Aug 04, 2026

  55 Hoags Cross Rd, Ossining, NY 10562

  • 3 Beds
  • 2 Baths
  • 2,292 Sq Ft
  • Built 1964

  Last Sold Summary

  • 4% Below List Price
  • $377/SF
  • 57 Days On Market

  Current Estimated Value $861,048

  Last Listing Agent Maryanne Durr Coldwell Banker Realty

  55 Hoags Cross Rd, Ossining, NY 10562
• 

  Est $621,792

  Not Listed For Sale

  8 Robert Rinaldi Ln, Briarcliff Manor, NY 10510

  • 2 Beds
  • 2.5 Baths
  • 1,566 Sq Ft
  • Built 2015

  8 Robert Rinaldi Ln, Briarcliff Manor, NY 10510

  Last Sold Summary

  • 39 Days On Market

  Last Listing Agent Mary Ann Tighe Houlihan Lawrence Inc.
• 

  

  /21

  $295,000

  $20K PRICE DROP Pending

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft

  352 N State Rd Unit 1H, Briarcliff Manor, NY 10510

  Welcome to Briar Hill, one of Briarcliff Manor’s most charming garden-style co-op communities. This classic brick Colonial complex is set amid tranquil, park-like grounds, yet is just minutes from the village center, dining, and everyday conveniences.This pristine first-floor residence offers two comfortable bedrooms, a beautifully renovated gourmet kitchen featuring granite countertops and a

  Jody Toth Corcoran Legends Realty

  352 N State Rd Unit 1H, Briarcliff Manor, NY 10510
• 

  $280,000

  Sold Sep 17, 2025

  92 Charter Cir Unit 92, Ossining, NY 10562

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft
  • Built 1961

  Last Sold Summary

  • 2% Above List Price
  • $295/SF
  • 14 Days On Market

  Last Listing Agent Valerie Cascione Compass Greater NY, LLC

  92 Charter Cir Unit 92, Ossining, NY 10562
• 

  Not Listed For Sale

  506 Kemeys Cove Unit 506, Ossining, NY 10562

  • 2 Beds
  • 2.5 Baths
  • 1,298 Sq Ft
  • Built 1975

  506 Kemeys Cove Unit 506, Ossining, NY 10562

  Last Sold Summary

  • 26 Days On Market

  Last Listing Agent Madelyn Ricciardi Houlihan Lawrence Inc.
• 

  

  /36

  $599,000

  • 3 Beds
  • 1 Bath
  • 1,510 Sq Ft

  23 Gates Ave, Ossining, NY 10562

  This lovingly maintained, one level home offers the ideal location- so convenient to all and a beautiful level backyard....You will be impressed with the very private outdoor space ready for entertaining and warm weather enjoyment -a country neighborhood feel yet only 10 minutes to Metro North station- a 50 min express commute to Grand Central and 2-3 miles to Rt 9/ Taconic Parkway....A warm and

  Maureen Connolly Coldwell Banker Realty

  23 Gates Ave, Ossining, NY 10562
• 

  $605,000

  Sold Feb 21, 2026

  126 Whitetail Cir, Ossining, NY 10562

  • 2 Beds
  • 2.5 Baths
  • 1,886 Sq Ft
  • Built 1986

  Last Sold Summary

  • 3% Above List Price
  • $321/SF
  • 23 Days On Market

  Current Estimated Value $609,521

  Last Listing Agent Kathleen Courtney Coldwell Banker Realty

  126 Whitetail Cir, Ossining, NY 10562
• 

  Est $980,995

  Not Listed For Sale

  45 Mystic Dr, Ossining, NY 10562

  • 2 Beds
  • 3.5 Baths
  • 2,715 Sq Ft
  • Built 1996

  45 Mystic Dr, Ossining, NY 10562

  Last Sold Summary

  • 79 Days On Market

  Last Listing Agent Gay Marglin Houlihan Lawrence Inc.
• 

  

  /28

  $625,000

  $20K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,539 Sq Ft

  83 Deerfield Ln, Ossining, NY 10562

  A tri-level gem, just minutes from downtown Ossining, this three bedroom home is perfect for those who need more space, but want less maintenance. Park either in the driveway or pull into the garage (with extra storage space). There is additional parking shortly down the street. Entering the home on the first floor, you will find a flexible bonus room, great for storage, an office or more. There

  Paul Leis North Country Sothebys Int Rlt

  83 Deerfield Ln, Ossining, NY 10562
• 

  $365,000

  Sold Jul 27, 2026

  16 Rockledge Ave Unit 2C-1, Ossining, NY 10562

  • 2 Beds
  • 2 Baths
  • 1,580 Sq Ft
  • Built 1970

  Last Sold Summary

  • 9% Below List Price
  • $231/SF
  • 44 Days On Market

  Last Listing Agent Gino Bello Howard Hanna Rand Realty

  16 Rockledge Ave Unit 2C-1, Ossining, NY 10562
• 

  Est $159,000

  Not Listed For Sale

  117 S Highland Ave Unit 5J, Ossining, NY 10562

  • 1 Bed
  • 1 Bath
  • 750 Sq Ft
  • Built 1962

  117 S Highland Ave Unit 5J, Ossining, NY 10562

  Last Sold Summary

  • 114 Days On Market

  Last Listing Agent Lisa Emanuele ERA Insite Realty Services
• 

  

  /38

  $799,000

  Pending

  • 2 Beds
  • 2.5 Baths
  • 1,656 Sq Ft

  4 Winterberry Ln, Briarcliff Manor, NY 10510

  Welcome to 4 Winterberry Lane, a beautifully updated townhouse tucked away on a quiet cul-de-sac in the highly sought-after Wyndcrest community. This move-in ready 2-bedroom, 2.1-bath home with a loft and finished lower level offers the perfect blend of style, comfort, and convenience in the heart of Briarcliff Manor. Ideally located just moments from the village, restaurants, shopping, parks,

  Suzan Zeolla Houlihan Lawrence Inc.

  4 Winterberry Ln, Briarcliff Manor, NY 10510
• 

  $625,000

  Sold Sep 02, 2025

  233 Woods Brooke Cir, Ossining, NY 10562

  • 2 Beds
  • 2.5 Baths
  • 1,475 Sq Ft
  • Built 1985

  Last Sold Summary

  • $424/SF
  • 26 Days On Market

  Current Estimated Value $639,284

  Last Listing Agent Carl Baker Ball Property Management LLC

  233 Woods Brooke Cir, Ossining, NY 10562
• 

  Est $517,323

  Not Listed For Sale

  1210 Eagle Bay Dr, Ossining, NY 10562

  • 2 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 1982

  1210 Eagle Bay Dr, Ossining, NY 10562

  Last Sold Summary

  • 26 Days On Market

  Last Listing Agent Kristen da Costa Coldwell Banker Realty
• 

  

  /42

  $850,000

  Pending

  • 3 Beds
  • 3 Baths
  • 2,240 Sq Ft

  21 Hawkes Ave, Ossining, NY 10562

  Offered for the first time ever, 21 Hawkes Avenue is a one of a kind contemporary residence in the Town of Ossining custom built by its current owner, an accomplished contractor, and designed by architect Jim Picone. Completed in 1983 and thoughtfully improved over the years, the home sits on a private, wooded 1.5-acre parcel originally acquired in 1980. A winding, tree-lined driveway leads to

  Laura Bulfamante Houlihan Lawrence Inc.

  21 Hawkes Ave, Ossining, NY 10562
• 

  $164,000

  Sold Oct 29, 2025

  131 S Highland Ave Unit A3, Ossining, NY 10562

  • 1 Bed
  • 1 Bath
  • 750 Sq Ft
  • Built 1962

  Last Sold Summary

  • 3% Above List Price
  • $219/SF
  • 58 Days On Market

  Last Listing Agent Amit Shah Compass Greater NY, LLC

  131 S Highland Ave Unit A3, Ossining, NY 10562
• 

  Est $404,549

  Not Listed For Sale

  7 Nicole Cir Unit 7, Ossining, NY 10562

  • 1 Bed
  • 2 Baths
  • 1,127 Sq Ft
  • Built 1987

  7 Nicole Cir Unit 7, Ossining, NY 10562

  Last Sold Summary

  • 82 Days On Market

  Last Listing Agent Nancy Kennedy Houlihan Lawrence Inc.
• 

  

  /46

  $1,460,000

  Pending

  • 4 Beds
  • 2 Baths
  • 2,152 Sq Ft

  670 Long Hill Rd W, Briarcliff Manor, NY 10510

  Designed by acclaimed architect Edward G. Schildbach, this remarkable mid-century modern residence is a masterful blend of iconic architecture and natural beauty. Gracefully nestled into the hillside, the home's thoughtfully designed approach creates a striking first impression, leading to an interior where walls of glass, natural stone, rich wood, and soaring architectural lines blur the

  Amy Via Houlihan Lawrence Inc.

  670 Long Hill Rd W, Briarcliff Manor, NY 10510
• 

  $515,000

  Sold Jan 29, 2026

  61 Snowden Ave, Ossining, NY 10562

  • 3 Beds
  • 1 Bath
  • 1,516 Sq Ft
  • Built 1957

  Last Sold Summary

  • 3% Above List Price
  • $340/SF
  • 30 Days On Market

  Current Estimated Value $533,856

  Last Listing Agent Paul Leis North Country Sothebys Int Rlt

  61 Snowden Ave, Ossining, NY 10562
• 

  Not Listed For Sale

  129 S Highland Ave Unit C6, Ossining, NY 10562

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft
  • Built 1965

  129 S Highland Ave Unit C6, Ossining, NY 10562

  Last Sold Summary

  • 82 Days On Market

  Last Listing Agent James Racioppo Coldwell Banker Realty
• 

  

  /25

  $599,000

  Pending

  • 2 Beds
  • 2 Baths
  • 1,307 Sq Ft

  45 Copley Unit 45, Briarcliff Manor, NY 10510

  Classic at the Copley. Luxury condominium living with a large two-bedroom, two bath, and featuring two private terraces overlooking the pool with scenic views and privacy. Enjoy an open and comfortable layout, gorgeous granite kitchen counters, in-unit new washer and dryer, elevator access, an indoor garage, and a private storage unit. Resort style living with all the amenities. Kick back Copley

  Ali Alvarez Houlihan Lawrence Inc.

  45 Copley Unit 45, Briarcliff Manor, NY 10510
• 

  $377,500

  Sold Jan 13, 2026

  16 Rockledge Ave Unit 7J, Ossining, NY 10562

  • 2 Beds
  • 2 Baths
  • 1,580 Sq Ft
  • Built 1968

  Last Sold Summary

  • 2% Below List Price
  • $239/SF
  • 122 Days On Market

  Last Listing Agent Janet Brand Houlihan Lawrence Inc.

  16 Rockledge Ave Unit 7J, Ossining, NY 10562

Showing Results 241 - 280, Page 7 of 18