Ossining, NY Homes

• 

  $199,999 Sold Oct 21, 2025

  360 N State Rd Unit 2 I, Ossining, NY 10510

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft
  • Built 1950

  Last Sold Summary

  • $250/SF
  • 18 Days On Market

  Last Listing Agent Loretta Fleming Chiavetta Coldwell Banker Realty

  360 N State Rd Unit 2 I, Ossining, NY 10510
• 

  Est $384,000 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,576 Sq Ft

  73 Spring St Unit 1Y, Ossining, NY 10562

  73 Spring St Unit 1Y, Ossining, NY 10562
• 

  

  

  /38

  $399,000

  • 1 Bed
  • 1 Bath
  • 1,089 Sq Ft

  101 Eagle Bay Dr Unit 101, Ossining, NY 10562

  Eagle Bay! Discover serene living in this first floor - no steps - 1 bedroom condominium home. Eagle Bay has incredible grounds with gardens, flowering trees and incredibly maintained homes, all in a gated community. Large living and dining room, updated eat-in-kitchen and a large bedroom with ample closets. Private outdoor space with privacy and wooded views. Clubhouse, pool, tennis, pickle

  Nancy Kennedy

  101 Eagle Bay Dr Unit 101, Ossining, NY 10562
• 

  $956,000 Sold Jun 25, 2025

  21 Vails Ln, Ossining, NY 10562

  • 5 Beds
  • 3.5 Baths
  • 2,684 Sq Ft
  • Built 1968

  Last Sold Summary

  • 3% Above List Price
  • $356/SF
  • 17 Days On Market

  Current Estimated Value $963,847

  Last Listing Agent Sherry Wiggs Houlihan Lawrence Inc.

  21 Vails Ln, Ossining, NY 10562
• 

  Est $843,554 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,655 Sq Ft

  47 Briarbrook Dr, Briarcliff Manor, NY 10510

  47 Briarbrook Dr, Briarcliff Manor, NY 10510
• 

  

  /50

  $500,000 Pending

  • 2 Beds
  • 2.5 Baths
  • 1,178 Sq Ft

  88 Broadway Unit 4, Ossining, NY 10562

  Discover this stunning penthouse in Ossining’s landmark 1820s schoolhouse conversion, where SoHo loft vibes blend with Hudson Valley charm. With dramatic architectural lines including soaring ceilings, exposed brick, wood beams, copper piping, and clerestory windows, every detail tells a story. The open-concept main level features a sunlit living room, elevated kitchen with granite counters and

  Lauren Zaccaria Houlihan Lawrence Inc.

  88 Broadway Unit 4, Ossining, NY 10562
• 

  $840,000 Sold Dec 19, 2025

  58 Narragansett Ave, Ossining, NY 10562

  • 4 Beds
  • 2.5 Baths
  • 2,202 Sq Ft
  • Built 1997

  Last Sold Summary

  • 4% Below List Price
  • $381/SF
  • 39 Days On Market

  Last Listing Agent Luis Morgado HomeSmart Homes & Estates

  58 Narragansett Ave, Ossining, NY 10562
• 

  Est $324,000 Not Listed For Sale

  • 1 Bed
  • 1.5 Baths
  • 893 Sq Ft

  63 Dale Ave Unit B3, Ossining, NY 10562

  63 Dale Ave Unit B3, Ossining, NY 10562
• 

  

  /10

  $399,222 Pending

  • 4 Beds
  • 2 Baths
  • 2,116 Sq Ft

  22 William St, Ossining, NY 10562

  Calling all contractors, investors, and end users! This classic two-family home is brimming with potential and offers an incredible opportunity to restore, renovate, or reimagine the space to fit your needs. Whether you're looking for a solid income-producing rental property or a place to call home while offsetting your mortgage by renting out the second unit—this is the one! Key Features: two

  Mark Seiden Mark Seiden Real Estate Team

  22 William St, Ossining, NY 10562
• 

  $1,450,000 Sold Aug 07, 2025

  30 Cottonwood Ln, Briarcliff Manor, NY 10510

  • 4 Beds
  • 2.5 Baths
  • 3,568 Sq Ft
  • Built 1977

  Last Sold Summary

  • 9% Above List Price
  • $406/SF
  • 17 Days On Market

  Current Estimated Value $1,478,407

  Last Listing Agent Maria Teresa Duguet Houlihan Lawrence Inc.

  30 Cottonwood Ln, Briarcliff Manor, NY 10510
• 

  Est $617,094 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,390 Sq Ft

  253 Woods Brooke Cir, Ossining, NY 10562

  253 Woods Brooke Cir, Ossining, NY 10562
• 

  

  /50

  $900,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,715 Sq Ft

  9 High Ridge Rd, Ossining, NY 10562

  Make an easy lifestyle transition to resort-style living in this beautifully-updated 3 bedroom, 2.1 bath townhome in Mystic Pointe, northern Ossining’s sought-after, gated luxury waterfront condominium community. This sizable, sunny, pristine tri-level end unit, known as a Biscayne, lives much like a single family house with its kitchen, dining and living areas all on the main floor, all bedrooms

  Cindy Cassuto Corcoran Legends Realty

  9 High Ridge Rd, Ossining, NY 10562
• 

  $799,000 Sold Jun 24, 2025

  3 Willow Dr, Briarcliff Manor, NY 10510

  • 4 Beds
  • 2.5 Baths
  • 1,886 Sq Ft
  • Built 1959

  Last Sold Summary

  • 1% Above List Price
  • $424/SF
  • 12 Days On Market

  Current Estimated Value $813,169

  Last Listing Agent Susan Slotnick William Raveis Real Estate

  3 Willow Dr, Briarcliff Manor, NY 10510
• 

  Est $647,795 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,616 Sq Ft

  192 Horseshoe Cir, Ossining, NY 10562

  192 Horseshoe Cir, Ossining, NY 10562
• 

  

  /34

  $899,000

  • 7 Beds
  • 3 Baths
  • 2,224 Sq Ft

  25 William St, Ossining, NY 10562

  This spacious three-family home in Ossining offers three full stories plus a finished basement, perfect for multi-generational living or rental income. Each unit features its own living areas, kitchen, and bedrooms, providing privacy and flexibility for family members or tenants. The first floor includes a living room, central kitchen and dining area, three bedrooms, and a full bath. The second

  Etan Hakimi Mitra Hakimi Realty Group LLC

  25 William St, Ossining, NY 10562
• 

  $215,000 Sold Sep 03, 2025

  133 S Highland Ave Unit B4, Ossining, NY 10562

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Built 1962

  Last Sold Summary

  • $239/SF
  • 34 Days On Market

  Last Listing Agent Mark Seiden Mark Seiden Real Estate Team

  133 S Highland Ave Unit B4, Ossining, NY 10562
• 

  Est $1,168,889 Not Listed For Sale

  • 6 Beds
  • 4 Baths
  • 5,500 Sq Ft

  31 Beach Rd, Ossining, NY 10562

  31 Beach Rd, Ossining, NY 10562
• 

  

  /42

  $1,100,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,643 Sq Ft

  320 Cedar Dr W, Briarcliff Manor, NY 10510

  Stately 4 Bedroom, 2 1/2 bathroom colonial set high on .94 acres at the end of a quiet cul-de-sac in Briarcliff Manor. The newly refurbished deck, accessible from the kitchen and family room, offers a place to relax or entertain in the privacy of your backyard. A large 2 room basement has the potential to legalize and make it into an office and playroom. The main floor laundry room adds to this

  Susan Strawgate Code Houlihan Lawrence Inc.

  320 Cedar Dr W, Briarcliff Manor, NY 10510
• 

  $750,000 Sold Dec 04, 2025

  1305 Grants Ln, Ossining, NY 10562

  • 2 Beds
  • 1 Bath
  • 1,469 Sq Ft
  • Built 1940

  Last Sold Summary

  • $511/SF
  • 13 Days On Market

  Last Listing Agent Beth Silfen Compass Greater NY, LLC

  1305 Grants Ln, Ossining, NY 10562
• 

  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 432 Sq Ft

  23 Camp Ground, Ossining, NY 10562

  23 Camp Ground, Ossining, NY 10562
• 

  

  /37

  $1,090,000

  • 3 Beds
  • 2.5 Baths
  • 3,990 Sq Ft

  81 Glendale Rd, Ossining, NY 10562

  Fully Available. Fantastic find for nature lovers seeking total stillness away form the City hustle and bustle, just a short 1 hr train ride from Manhattan! 14.5 wooded acres with beautiful stone outcroppings and a few clearings, suitable for chickens, goats and/or horses. The property has rustic outbuildings and walking paths that connect to Teatown trails. This home has large rooms with

  Helena Macintyre North Country Sothebys Int Rlt

  81 Glendale Rd, Ossining, NY 10562
• 

  $805,000 Sold Nov 18, 2025

  38 Ganung Dr, Ossining, NY 10562

  • 4 Beds
  • 3.5 Baths
  • 2,585 Sq Ft
  • Built 1956

  Last Sold Summary

  • 2% Above List Price
  • $311/SF
  • 25 Days On Market

  Last Listing Agent Janet Brand Houlihan Lawrence Inc.

  38 Ganung Dr, Ossining, NY 10562
• 

  Est $516,000 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 736 Sq Ft

  16 Rockledge Ave Unit 2MM-2, Ossining, NY 10562

  16 Rockledge Ave Unit 2MM-2, Ossining, NY 10562
• 

  

  /37

  $332,500 Pending

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

  16 Rockledge Ave Unit 5B1, Ossining, NY 10562

  Inspirational. Awe inspiring. Witness first-hand the most stunning panoramic Hudson River views from EVERY room of this large two-bedroom, two-bathroom coop apartment in exceptional, Scarborough Manor—a gated community in Ossining, NY. This unit has exquisite, unobstructed southern views of one of the most poetically beautiful rivers in the world. The primary bedroom ensuite has its own

  Melissa Terman River Realty Services, Inc.

  16 Rockledge Ave Unit 5B1, Ossining, NY 10562
• 

  $2,150,000 Sold Sep 17, 2025

  7 Purdy Ct, Briarcliff Manor, NY 10510

  • 4 Beds
  • 4 Baths
  • 3,362 Sq Ft
  • Built 1979

  Last Sold Summary

  • 30% Above List Price
  • $640/SF
  • 12 Days On Market

  Current Estimated Value $2,081,018

  Last Listing Agent Shari Besterman Houlihan Lawrence Inc.

  7 Purdy Ct, Briarcliff Manor, NY 10510
• 

  Est $734,202 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,620 Sq Ft

  52 Mystic Dr, Ossining, NY 10562

  52 Mystic Dr, Ossining, NY 10562
• 

  /2

  $300,000 Pending

  • 2 Beds
  • 1 Bath
  • 1,474 Sq Ft

  30 Hunter St, Ossining, NY 10562

  Here is your chance to take advantage of a rare opportunity to buy a designers honeymoon with water views and close to transportation. Must be purchased sight unseen with occupants inside. CASH ONLY. Tear it down and build something new. Renovate and make it your own. DRIVE BY SHOWINGS ONLY! DO NOT KNOCK ON THE DOOR OR GO ON THE PROPERTY AT ALL! Additional Information: HeatingFuel:Oil Below

  Crystal Hawkins Syska Keller Williams NY Realty

  30 Hunter St, Ossining, NY 10562
• 

  $390,000 Sold Aug 04, 2025

  9 Briarcliff Dr S Unit 2, Ossining, NY 10562

  • 2 Beds
  • 2 Baths
  • 1,065 Sq Ft
  • Built 1978

  Last Sold Summary

  • 1% Above List Price
  • $366/SF
  • 20 Days On Market

  Current Estimated Value $386,000

  Last Listing Agent Mark Boyland Keller Williams Realty Partner

  9 Briarcliff Dr S Unit 2, Ossining, NY 10562
• 

  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 950 Sq Ft

  352 N State Rd Unit 4H, Briarcliff Manor, NY 10510

  352 N State Rd Unit 4H, Briarcliff Manor, NY 10510
• 

  

  /50

  $3,300,000

  • 5 Beds
  • 7 Baths
  • 7,931 Sq Ft

  36 Revolutionary Rd, Briarcliff Manor, NY 10510

  The Essence of Westchester Luxury. A Grand Briarcliff Manor Estate Nestled on 3.83 Private Acres. Perfectly positioned between the Hudson River and Sleepy Hollow Country Club. World-class dining, shopping and Metro North train are nearby, blending convenience with serene privacy. The stately home boasts five spacious ensuite bedrooms, including a spectacular primary suite with a cozy

  Elaine Wasserman Houlihan Lawrence Inc.

  36 Revolutionary Rd, Briarcliff Manor, NY 10510
• 

  $450,000 Sold Oct 27, 2025

  27 Knoll View, Ossining, NY 10562

  • 2 Beds
  • 1.5 Baths
  • 1,200 Sq Ft
  • Built 1989

  Last Sold Summary

  • 2% Below List Price
  • $375/SF
  • 42 Days On Market

  Last Listing Agent James Hawkins D.L. Hawkins Realty LLC

  27 Knoll View, Ossining, NY 10562
• 

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft

  121 S Highland Ave Unit 5A, Ossining, NY 10562

  121 S Highland Ave Unit 5A, Ossining, NY 10562
• 

  

  /23

  $514,999 Pending

  • 2 Beds
  • 2.5 Baths
  • 1,265 Sq Ft

  608 Kemeys Cove Unit 6-08, Briarcliff Manor, NY 10510

  Welcome to 608 Kemeys Cove, a beautifully maintained 2-bedroom, 2.5-bathroom duplex condominium nestled in the sought-after Kemeys Cove community in Briarcliff Manor. Step inside to a spacious and thoughtfully designed layout that flows seamlessly between the living, dining, and kitchen areas—ideal for today’s lifestyle. The primary bedroom suite offers a serene retreat with a private bathroom

  Kareem Kirby Keller Williams Realty NYC Grp

  608 Kemeys Cove Unit 6-08, Briarcliff Manor, NY 10510
• 

  $160,000 Sold Oct 03, 2025

  48 Gordon Ave, Briarcliff Manor, NY 10510

  • Land
  • 0.99 Acre
  • $161,731 per Acre

  Last Sold Summary

  • 29% Below List Price
  • 125 Days On Market

  Last Listing Agent Eric Stein RE/MAX Distinguished Hms.&Prop

  48 Gordon Ave, Briarcliff Manor, NY 10510
• 

  Est $2,058,961 Not Listed For Sale

  • 4 Beds
  • 6 Baths
  • 5,400 Sq Ft

  12 Arrow Tree Ln, Briarcliff Manor, NY 10510

  12 Arrow Tree Ln, Briarcliff Manor, NY 10510
• 

  

  /50

  $679,000

  • 5 Beds
  • 2.5 Baths
  • 3,656 Sq Ft

  33 Ryder Rd, Ossining, NY 10562

  FREE 12 MONTH HOME WARRANTY that covers electrical/plumbing/appliances/and MORE! This historically charming Center Hall Colonial Farmhouse is situated on almost an acre of pristine land. Own a piece of Westchester County history with this 1826 built farmhouse, enjoy 7' high ceilings, wide planked hardwood floors, and three working fireplaces. HUGE dry walkout basement with an enormous walk-up

  Justin Landon Howard Hanna Rand Realty

  33 Ryder Rd, Ossining, NY 10562
• 

  $545,000 Sold Aug 26, 2025

  263 Horseshoe Cir, Ossining, NY 10562

  • 1 Bed
  • 2.5 Baths
  • 1,652 Sq Ft
  • Built 1986

  Last Sold Summary

  • 4% Below List Price
  • $330/SF
  • 28 Days On Market

  Current Estimated Value $547,195

  Last Listing Agent Jamie Fosgate Nestedge Realty

  263 Horseshoe Cir, Ossining, NY 10562
• 

  Est $530,999 Not Listed For Sale

  • 1 Bed
  • 1.5 Baths
  • 1,248 Sq Ft

  213 Woods Brooke Ct, Ossining, NY 10562

  213 Woods Brooke Ct, Ossining, NY 10562
• 

  

  /39

  $899,888 Pending

  • 4 Beds
  • 2.5 Baths
  • 3,946 Sq Ft

  59 Somerstown Rd, Ossining, NY 10562

  Welcome to this stunning Hudson Valley Greek Revival home, a rare architectural gem that blends historic elegance with modern comfort. Set on a beautifully landscaped, park like property with fruit trees and ornamental gardens, this 4+ bedroom, 2.5 bath home offers a peaceful country lifestyle just minutes from vibrant Hudson Valley villages, towns and amenities. Enter through a circular driveway

  Janet Brand Houlihan Lawrence Inc.

  59 Somerstown Rd, Ossining, NY 10562
• 

  $240,000 Sold Oct 07, 2025

  196 Charter Cir Unit 196, Ossining, NY 10562

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

  Last Sold Summary

  • 4% Below List Price
  • $267/SF
  • 45 Days On Market

  Last Listing Agent Concetta Connie Gallo Howard Hanna Rand Realty

  196 Charter Cir Unit 196, Ossining, NY 10562

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