Ossining, NY Homes

• 

  Est $485,122

  Not Listed For Sale

  94 Deer Run, Ossining, NY 10562

  • 1 Bed
  • 1.5 Baths
  • 1,234 Sq Ft
  • Built 1986

  94 Deer Run, Ossining, NY 10562

  Last Sold Summary

  • 9 Days On Market
• 

  

  

  /34

  $899,000

  $50K PRICE DROP Pending

  • 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
• 

  $653,000

  Sold Oct 22, 2025

  407 Glenwood Dr, Briarcliff Manor, NY 10510

  • 2 Beds
  • 2.5 Baths
  • 1,837 Sq Ft
  • Built 2001

  Last Sold Summary

  • 9% Above List Price
  • $355/SF
  • 19 Days On Market

  Current Estimated Value $674,627

  Last Listing Agent Suzan Zeolla Houlihan Lawrence Inc.

  407 Glenwood Dr, Briarcliff Manor, NY 10510
• 

  Est $158,000

  Not Listed For Sale

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

  • Studio
  • 1 Bath
  • 650 Sq Ft
  • Built 1964

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

  Last Sold Summary

  • 42 Days On Market
• 

  

  

  /48

  $2,699,000

  $296K PRICE DROP Pending

  • 4 Beds
  • 3.5 Baths
  • 3,282 Sq Ft

  132 Ridgecrest Rd, Briarcliff Manor, NY 10510

  BREATHTAKING YEAR ROUND HUDSON RIVER PANORAMIC VIEWS define this iconic Mid-Century Modern residence! Located on Briarcliff’s coveted Ridgecrest Road in the highly sought-after Briarcliff Manor School District, this modern masterpiece, being sold FURNISHED, is well known in architectural and interior design circles. Ideally located just minutes from the Scarborough Metro-North station, this home

  Cindy Glynn Compass Greater NY, LLC

  132 Ridgecrest Rd, Briarcliff Manor, NY 10510
• 

  $320,000

  Sold Dec 29, 2025

  20 Maple Place, Ossining, NY 10562

  • 5 Beds
  • 1.5 Baths
  • 2,880 Sq Ft
  • Built 1870

  Last Sold Summary

  • 12% Below List Price
  • $111/SF
  • 284 Days On Market

  Current Estimated Value $510,502

  Last Listing Agent Gary Leogrande Keller Williams NY Realty

  20 Maple Place, Ossining, NY 10562
• 

  Est $412,892

  Not Listed For Sale

  6 Steven Dr Unit 5, Ossining, NY 10562

  • 1 Bed
  • 1 Bath
  • 825 Sq Ft
  • Built 1988

  6 Steven Dr Unit 5, Ossining, NY 10562

  Last Sold Summary

  • 23 Days On Market
• 

  

  /45

  $1,799,999

  Pending

  • 5 Beds
  • 4.5 Baths
  • 6,458 Sq Ft

  11 Hollow Tree Rd, Briarcliff Manor, NY 10510

  Nestled on a quiet cul-de-sac in Briarcliff Manor, this inviting 5-bedroom, 4.5 bath home combines space, light, and a layout that simply works for the way people live today. A grand entry foyer with hardwood floors and inlay detail sets the tone, opening to well-proportioned formal and informal spaces suited for both everyday living and entertaining. The living room features recessed lighting

  Suzan Zeolla Houlihan Lawrence Inc.

  11 Hollow Tree Rd, Briarcliff Manor, NY 10510
• 

  $150,000

  Sold Jan 13, 2026

  117 S Highland Ave Unit 6J, Ossining, NY 10562

  • 1 Bed
  • 1 Bath
  • 750 Sq Ft
  • Built 1969

  Last Sold Summary

  • $200/SF
  • 9 Days On Market

  Current Estimated Value $158,000

  Last Listing Agent Peter Raider Real Broker NY LLC

  117 S Highland Ave Unit 6J, Ossining, NY 10562
• 

  Est $597,658

  Not Listed For Sale

  222 Woods Brooke Cir, Ossining, NY 10562

  • 2 Beds
  • 2.5 Baths
  • 1,390 Sq Ft
  • Built 1983

  222 Woods Brooke Cir, Ossining, NY 10562

  Last Sold Summary

  • 16 Days On Market
• 

  

  /18

  $750,000

  • 4 Beds
  • 2 Baths
  • 2,110 Sq Ft

  321 Spring St, Ossining, NY 10562

  Beautifully maintained TWO FAMILY DUPLEX in the cherished, historic Sparta district! Each 1000 sq. foot apartment features two bedrooms, one updated bathroom, living room, kitchen, dining room and large bright 4 season sun sunroom. The full, unfinished basement features two laundry stations, one for each unit plus plenty of storage. Additional features include oak hardwood floors, stucco walls &

  Margaret Callaci Corcoran Legends Realty

  321 Spring St, Ossining, NY 10562
• 

  $1,650,000

  Sold Apr 24, 2026

  2 Lodge Rd, Briarcliff Manor, NY 10510

  • 6 Beds
  • 5.5 Baths
  • 5,700 Sq Ft
  • Built 1996

  Last Sold Summary

  • $289/SF
  • 12 Days On Market

  Current Estimated Value $1,850,417

  Last Listing Agent Arya Rabinovits eRealty Advisors, Inc

  2 Lodge Rd, Briarcliff Manor, NY 10510
• 

  Not Listed For Sale

  224 Kemeys Cove Unit 2-24, Briarcliff Manor, NY 10510

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

  224 Kemeys Cove Unit 2-24, Briarcliff Manor, NY 10510

  Last Sold Summary

  • 41 Days On Market
• 

  

  /35

  $750,000

  $29K PRICE DROP Pending

  • 4 Beds
  • 2 Baths
  • 2,034 Sq Ft

  15 Marshall Place, Ossining, NY 10562

  Welcome home to a charming two family Dutch Colonial in the Forest Park area of Ossining. Each unit features two bedrooms, full bath, living room, dining room, & kitchen. The first floor unit has access to a full basement with laundry & plenty of storage. The second floor unit also has 2 bedrooms, full bath, living room, dining room & attic space. Hardwood floors, high ceilings & plenty of

  Elizabeth Kamp Kane & Associates

  15 Marshall Place, Ossining, NY 10562
• 

  $445,000

  Sold Oct 07, 2025

  705 Briarcliff Dr S, Ossining, NY 10562

  • 2 Beds
  • 2 Baths
  • 1,288 Sq Ft
  • Built 1977

  Last Sold Summary

  • 2% Above List Price
  • $345/SF
  • 46 Days On Market

  Last Listing Agent Cindy Cassuto Corcoran Legends Realty

  705 Briarcliff Dr S, Ossining, NY 10562
• 

  Est $371,535

  Not Listed For Sale

  103 Eagle Bay Dr, Ossining, NY 10562

  • 1 Bed
  • 1 Bath
  • 1,089 Sq Ft
  • Built 1982

  103 Eagle Bay Dr, Ossining, NY 10562

  Last Sold Summary

  • 22 Days On Market
• 

  

  /21

  $699,000

  • 5 Beds
  • 2 Baths
  • 1,860 Sq Ft

  1 Edward St, Ossining, NY 10562

  Well-maintained two-unit property in the heart of Ossining, fully renovated in 2020 and offering a strong combination of space, convenience, and versatility. The building features a spacious three-bedroom second floor unit that is ready for immediate occupancy over a two-bedroom unit, providing an ideal opportunity for owner-occupants or investors. Both units benefit from updated finishes

  Tana McGuire eXp Realty

  1 Edward St, Ossining, NY 10562
• 

  $490,000

  Sold Jul 31, 2025

  49 Pine Ave, Ossining, NY 10562

  • 3 Beds
  • 1 Bath
  • 1,026 Sq Ft
  • Built 1963

  Last Sold Summary

  • 2% Above List Price
  • $478/SF
  • 36 Days On Market

  Current Estimated Value $517,805

  Last Listing Agent Kelly Castiglione Coldwell Banker Realty

  49 Pine Ave, Ossining, NY 10562
• 

  Est $498,113

  Not Listed For Sale

  1010 Eagle Bay Dr, Ossining, NY 10562

  • 1 Bed
  • 2 Baths
  • 1,378 Sq Ft
  • Built 1982

  1010 Eagle Bay Dr, Ossining, NY 10562

  Last Sold Summary

  • 18 Days On Market
• 

  

  /38

  $499,900

  Pending

  • 2 Beds
  • 2 Baths
  • 1,400 Sq Ft

  9 Nicole Cir Unit 8, Ossining, NY 10562

  Offering an open floorplan with sophistication and style filled with designer finishes. This wonderfully maintain unit offers an impressive eat in kitchen with granite counters, stainless steel appliances and rich cabinetry, the dining room flows into the living area complete with fireplace and vaulted ceilings with skylight. The primary bedroom is located on the main level, with vaulted

  Robert Mulvey William Raveis Real Estate

  9 Nicole Cir Unit 8, Ossining, NY 10562
• 

  $699,000

  Sold Dec 19, 2025

  5 Cedar Place, Ossining, NY 10562

  • 3 Beds
  • 3 Baths
  • 2,272 Sq Ft
  • Built 1931

  Last Sold Summary

  • 4% Below List Price
  • $308/SF
  • 73 Days On Market

  Current Estimated Value $714,874

  Last Listing Agent Brian Perez Century 21 Hire Realty

  5 Cedar Place, Ossining, NY 10562
• 

  Est $725,380

  Not Listed For Sale

  59 Briarbrook Dr, Briarcliff Manor, NY 10510

  • 2 Beds
  • 2.5 Baths
  • 2,000 Sq Ft
  • Built 2001

  59 Briarbrook Dr, Briarcliff Manor, NY 10510

  Last Sold Summary

  • 15 Days On Market
• 

  

  /22

  $699,000

  $26K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 1,960 Sq Ft

  2 Piping Rock Dr, Ossining, NY 10562

  VERSATILE "HIGH RANCH" HOME NESTLED INTO GENTLE ROLLING HILLSIDE. SOUTH WESTERN EXPOSURE, MANICURED LAWN, LOWER BRICK FRONT FACADE ACCENT, ALONG WITH GENEROUS DRIVEWAY PARKING. THE LIVING ROOM W/TRIPLE WINDOW, DINING AREA, EAT-IN-KITCHEN W/BACK YARD ACCESS, HALL BATHROOM, 2 BEDROOMS, PRIMARY BEDROOM W/HALF BATH - ARE ON THE UPPER LIVING LEVEL. THE RECREATION RM, OFFICE/GUEST BEDROOM, BATHROOM,

  Greg Kane Kane & Associates

  2 Piping Rock Dr, Ossining, NY 10562
• 

  $635,000

  Sold Dec 16, 2025

  7 Birchbrook Rd, Ossining, NY 10562

  • 4 Beds
  • 2 Baths
  • 2,049 Sq Ft
  • Built 1955

  Last Sold Summary

  • 2% Below List Price
  • $310/SF
  • 55 Days On Market

  Current Estimated Value $669,772

  Last Listing Agent John Buoninfante Real Broker NY LLC

  7 Birchbrook Rd, Ossining, NY 10562
• 

  Not Listed For Sale

  18 Charter Cir Unit 18, Ossining, NY 10562

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

  18 Charter Cir Unit 18, Ossining, NY 10562

  Last Sold Summary

  • 25 Days On Market
• 

  

  /37

  $825,000

  $265K PRICE DROP

  • 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
• 

  $610,000

  Sold Nov 14, 2025

  73 van Cortlandt Ave, Ossining, NY 10562

  • 3 Beds
  • 2 Baths
  • 1,482 Sq Ft
  • Built 1882

  Last Sold Summary

  • 2% Above List Price
  • $412/SF
  • 56 Days On Market

  Current Estimated Value $628,785

  Last Listing Agent Patricia Wolny Corcoran Legends Realty

  73 van Cortlandt Ave, Ossining, NY 10562
• 

  Not Listed For Sale

  106 Kemeys Ave Unit 6, Briarcliff Manor, NY 10510

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

  106 Kemeys Ave Unit 6, Briarcliff Manor, NY 10510

  Last Sold Summary

  • 13 Days On Market
• 

  /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
• 

  $343,350

  Sold Dec 22, 2025

  4 William St, Ossining, NY 10562

  • 3 Beds
  • 2 Baths
  • 1,160 Sq Ft
  • Built 1826

  Last Sold Summary

  • 26% Below List Price
  • $296/SF
  • 1,016 Days On Market

  Current Estimated Value $436,320

  Last Listing Agent Jamarr Zellner REALHome Services & Solutions

  4 William St, Ossining, NY 10562
• 

  Not Listed For Sale

  135 S Highland Ave Unit B4, Ossining, NY 10562

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

  135 S Highland Ave Unit B4, Ossining, NY 10562

  Last Sold Summary

  • 16 Days On Market
• 

  

  /48

  $615,000

  Open House 7/11

  • 2 Beds
  • 2 Baths

  23 Hudson Point Ln, Ossining, NY 10562

  Rare Hudson River View Home with Resort-Style Amenities This beautiful main-level home offers picturesque Hudson River views and a tastefully upgraded kitchen and bathrooms, making it one of the rarest opportunities in this highly sought-after riverfront community in the Hudson Valley. Start your mornings with coffee and unwind in the evenings with your favorite beverage on your private covered

  Matthew Harms

  23 Hudson Point Ln, Ossining, NY 10562
• 

  $912,000

  Sold Sep 05, 2025

  16 Rockledge Ave Unit 5D-2, Ossining, NY 10562

  • 3 Beds
  • 2 Baths
  • 2,050 Sq Ft
  • Built 1970

  Last Sold Summary

  • 4% Below List Price
  • $445/SF
  • 41 Days On Market

  Current Estimated Value $432,000

  Last Listing Agent Susan Strawgate Code Houlihan Lawrence Inc.

  16 Rockledge Ave Unit 5D-2, Ossining, NY 10562
• 

  Not Listed For Sale

  648 Pinesbridge Rd, Ossining, NY 10562

  648 Pinesbridge Rd, Ossining, NY 10562

  Last Sold Summary

  • 27 Days On Market
• 

  

  /50

  $2,725,000

  Pending

  • 6 Beds
  • 7 Baths
  • 7,242 Sq Ft

  16 Austin Place, Briarcliff Manor, NY 10510

  Just the one you've been waiting for. Stunning 6 BR, 5.2 bath, post-modern colonial home of premier quality both inside and out. Vacation at home with these wonderful exterior features: magnificent salt water in-ground pool with 3 waterfalls & a spa, fully-equipped outdoor Kitchen/BBQ entertaining area on flagstone patio and lush level fenced-in lawn area. Young cul-de-sac neighborhood. Other

  Susan Strawgate Code Houlihan Lawrence Inc.

  16 Austin Place, Briarcliff Manor, NY 10510
• 

  $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 $714,580

  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
• 

  

  /40

  $85,000

  • 2 Beds
  • 1 Bath
  • 1,380 Sq Ft

  37 Secor Rd, Ossining, NY 10562

  Welcome to 37 Secor Road. Being sold strictly as-is and as a buy one get one with 39 Secor Road; You cannot pass on this deal! Get this cozy 2-bedroom, 1-bathroom single family home replete with a garage, unfinished basement and unobstructed windows to the Hudson River. This home is priced to be sold as a package with the adjoining Two family home at 39 Secor Road (MLS # 973596 offered @ $675K).

  Monica Cooper THD Homes LLC

  37 Secor Rd, Ossining, NY 10562
• 

  $525,000

  Sold Aug 11, 2025

  54 Hudson Point Ln, Ossining, NY 10562

  • 2 Beds
  • 2 Baths
  • 1,185 Sq Ft
  • Built 1993

  Last Sold Summary

  • 5% Above List Price
  • $443/SF
  • 25 Days On Market

  Current Estimated Value $543,817

  Last Listing Agent James Schunk Schunk Realty Group

  54 Hudson Point Ln, 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

Showing Results 201 - 240, Page 6 of 18