Ossining, NY Homes

• 

  Est $403,000 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,082 Sq Ft

  2 Briarcliff Dr S Unit 14, Ossining, NY 10562

  2 Briarcliff Dr S Unit 14, Ossining, NY 10562
• 

  

  

  /50

  $1,499,000

  • 3 Beds
  • 3.5 Baths
  • 4,300 Sq Ft

  383 Illington Rd, Ossining, NY 10562

  Welcome to 383 Illington Road – an amazing, oversized 3 bedroom colonial that lives like a 4 bedroom, with 10 foot ceilings, nestled on over 5 acres of picturesque, level land in the highly sought-after Yorktown Central School District. This exceptional property offers privacy, space, and convenience, including an additional lot with an adorable treehouse for everyone to enjoy. All just minutes

  Annette Cicinelli Keller Williams Realty Partner

  383 Illington Rd, Ossining, NY 10562
• 

  $725,000 Sold Jul 21, 2025

  6 Cedar Lane Terrace, Ossining, NY 10562

  • 4 Beds
  • 3 Baths
  • 3,016 Sq Ft
  • Built 1948

  Last Sold Summary

  • $240/SF
  • 222 Days On Market

  Current Estimated Value $748,593

  Last Listing Agent Thomas Nigro Schatz Realty Group

  6 Cedar Lane Terrace, Ossining, NY 10562
• 

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,627 Sq Ft

  333 N State Rd Unit PH63, Briarcliff Manor, NY 10510

  333 N State Rd Unit PH63, Briarcliff Manor, NY 10510
• 

  

  

  /40

  $510,000 Pending

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

  16 Rockledge Ave Unit 3E1, Ossining, NY 10562

  Welcome to Scarborough Manor, a premier Hudson River co-op community in Ossining offering resort-style amenities and spacious living. This rare three-bedroom, two-bath apartment in Building 1 spans 2,050 sq ft—one of the largest layouts in the complex—and is just minutes from the Scarborough Metro-North station. The oversized living room opens to a private terrace with Hudson River views, while

  Marcia Sousa Weichert Realtors

  16 Rockledge Ave Unit 3E1, Ossining, NY 10562
• 

  $514,000 Sold May 05, 2025

  106 Kemeys Ave Unit 6, Briarcliff Manor, NY 10510

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

  Last Sold Summary

  • 3% Above List Price
  • $396/SF
  • 13 Days On Market

  Last Listing Agent Mark Seiden Mark Seiden Real Estate Team

  106 Kemeys Ave Unit 6, Briarcliff Manor, NY 10510
• 

  Est $899,045 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 2,797 Sq Ft

  51 Croton Dam Rd, Ossining, NY 10562

  51 Croton Dam Rd, Ossining, NY 10562
• 

  

  /33

  $450,000

  • 2 Beds
  • 2 Baths
  • 1,148 Sq Ft

  2 N Water St Unit 1A, Ossining, NY 10562

  Beautiful riverfront SOHO style loft in converted 1800s brick schoolhouse facing the Hudson River, close to train, restaurants, riverfront, marinas, summer concerts on the river and all that glorious Hudson Valley riverfront life has to offer. Enjoy one level living in this fabulous open plan unit at the best corner spot in the building, with 14 foot ceilings and 10 foot windows, facing the

  Lynn Harmonay North Country Sothebys Int Rlt

  2 N Water St Unit 1A, Ossining, NY 10562
• 

  $355,000 Sold Apr 22, 2025

  16 Rockledge Ave Unit 2C2, Ossining, NY 10562

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

  Last Sold Summary

  • 11% Below List Price
  • $225/SF
  • 207 Days On Market

  Current Estimated Value $516,000

  Last Listing Agent Christopher Cawley Corcoran Legends Realty

  16 Rockledge Ave Unit 2C2, Ossining, NY 10562
• 

  Est $1,191,987 Not Listed For Sale

  363 Long Hill Rd E, Briarcliff Manor, NY 10510

  363 Long Hill Rd E, Briarcliff Manor, NY 10510
• 

  

  /50

  $699,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,332 Sq Ft

  7 Liberty St, Ossining, NY 10562

  Charming Renovated Historic Home in Sparta, Ossining | Hudson River Views & Prime Location Step into the timeless charm of this beautifully renovated 3-bedroom, 2-bath home nestled in the heart of historic Sparta—one of Ossining’s most coveted neighborhoods. Blending modern updates with authentic period details, this rare gem offers both comfort and character. Enjoy mornings on the classic front

  Elizabeth Harlow Compass Greater NY, LLC

  7 Liberty St, Ossining, NY 10562
• 

  $516,000 Sold Nov 14, 2025

  19 Lincoln Place Unit 55, Ossining, NY 10562

  • 2 Beds
  • 2.5 Baths
  • 1,658 Sq Ft
  • Built 1966

  Last Sold Summary

  • 3% Above List Price
  • $311/SF
  • 26 Days On Market

  Last Listing Agent Mark Seiden Mark Seiden Real Estate Team

  19 Lincoln Place Unit 55, Ossining, NY 10562
• 

  Est $681,228 Not Listed For Sale

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

  9 River Pkwy, Briarcliff Manor, NY 10510

  9 River Pkwy, Briarcliff Manor, NY 10510
• 

  

  /38

  $1,100,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,860 Sq Ft

  3 Holbrook Rd, Briarcliff Manor, NY 10510

  Behind stately iron gates on a quiet, tree-lined street in the heart of Briarcliff Manor, a remarkable home awaits—steeped in history, wrapped in charm, and gracefully updated for modern living. Originally built in 1897 as part of the historic Macy Estate, this enchanting Tudor-style Gate House offers a rare blend of vintage character and contemporary comfort across approx 2,800 square feet of

  Kathryn Weinberger Compass Greater NY, LLC

  3 Holbrook Rd, Briarcliff Manor, NY 10510
• 

  $1,415,000 Sold May 07, 2025

  101 Long Hill Rd E, Briarcliff Manor, NY 10510

  • 4 Beds
  • 3 Baths
  • 2,934 Sq Ft
  • Built 1947

  Last Sold Summary

  • 9% Above List Price
  • $482/SF
  • 9 Days On Market

  Current Estimated Value $1,446,891

  Last Listing Agent Maya Sheehan Compass Greater NY, LLC

  101 Long Hill Rd E, Briarcliff Manor, NY 10510
• 

  Est $814,419 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,305 Sq Ft

  7 Wolden Rd, Ossining, NY 10562

  7 Wolden Rd, Ossining, NY 10562
• 

  

  /21

  $130,000 Pending

  • 1 Bed
  • 1 Bath
  • 750 Sq Ft

  127 S Highland Ave Unit A4, Ossining, NY 10562

  Welcome to 127 S Highland Avenue, Unit A4 in Ossining, NY—a bright and inviting cooperative in the sought-after Highland Terrace Complex. This 1-bedroom, 1-bath home offers 750 square feet of comfortable living with a smart layout that makes everyday life feel simple and easy. Step inside and you’ll find a spacious living area that flows seamlessly into the rest of the home, creating a warm and

  Safiya Swan Keller Williams Realty Group

  127 S Highland Ave Unit A4, Ossining, NY 10562
• 

  $225,000 Sold Aug 12, 2025

  123 S Highland Ave Unit B3, Ossining, NY 10562

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

  Last Sold Summary

  • 2% Above List Price
  • $250/SF
  • 21 Days On Market

  Current Estimated Value $162,000

  Last Listing Agent Stephanie Rosenhaus William Raveis Real Estate

  123 S Highland Ave Unit B3, Ossining, NY 10562
• 

  Est $516,000 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,560 Sq Ft

  16 Rockledge Ave Unit 6J2, Ossining, NY 10562

  16 Rockledge Ave Unit 6J2, Ossining, NY 10562
• 

  

  /48

  $5,500,000

  • 7 Beds
  • 5.5 Baths
  • 5,700 Sq Ft

  433 Arcady Rd, Ossining, NY 10562

  Old Dam Farm — A Rare Hudson Valley LegacySet on nearly 40 pristine acres bordered by over 100 acres of protected New York City watershed land, Old Dam Farm offers an unparalleled combination of natural beauty, history, and lifestyle. This remarkable estate overlooks the sparkling Croton Reservoir, creating a backdrop of breathtaking views in every season.At its heart stands a

  Nancy Kennedy

  433 Arcady Rd, Ossining, NY 10562
• 

  $805,000 Sold Aug 12, 2025

  801 Syska Rd, Ossining, NY 10562

  • 2 Beds
  • 1.5 Baths
  • 1,328 Sq Ft
  • Built 1956

  Last Sold Summary

  • 15% Above List Price
  • $606/SF
  • 7 Days On Market

  Current Estimated Value $776,612

  Last Listing Agent Yona Strougo Compass Greater NY, LLC

  801 Syska Rd, Ossining, NY 10562
• 

  Est $631,638 Not Listed For Sale

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

  8 Robert Rinaldi Ln, Briarcliff Manor, NY 10510

  8 Robert Rinaldi Ln, Briarcliff Manor, NY 10510
• 

  

  /40

  $699,222

  • 6 Beds
  • 3 Baths
  • 3,254 Sq Ft

  7 Grandview Ave, Ossining, NY 10562

  Expanded 6 bedroom, 3 bath home on fenced-in property! Property is over assessed by 10% and taxes are based on a market value of $778,000. Once sold, the assessment may be grieved. This spacious home offers comfort, functionality, and room to grow. Nestled on a lovely level lot, the property features a newly painted rear deck, a storage shed, and a fully fenced yard—perfect for outdoor enjoyment.

  Mark Seiden Mark Seiden Real Estate Team

  7 Grandview Ave, Ossining, NY 10562
• 

  $850,000 Sold May 15, 2025

  19 High Ridge Rd, Ossining, NY 10562

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

  Last Sold Summary

  • 1% Below List Price
  • $313/SF
  • 15 Days On Market

  Current Estimated Value $869,665

  Last Listing Agent Gay Marglin Houlihan Lawrence Inc.

  19 High Ridge Rd, Ossining, NY 10562
• 

  Not Listed For Sale

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

  506 Kemeys Cove Unit 506, Ossining, NY 10562

  506 Kemeys Cove Unit 506, Ossining, NY 10562
• 

  

  /29

  $799,000 Pending

  • 4 Beds
  • 2 Baths
  • 2,252 Sq Ft

  40 Linden Ave, Ossining, NY 10562

  Welcome to this legal 2 family Stucco Victorian home style in the heart of it all! Great opportunity for those looking to owner-occupy one unit, and rent the other unit to offset some of your carrying cost or a great investment opportunity! This unique corner property offers character, charm, and details one expects from this vintage, complimented with updates for today's living needs. Unit 1:

  Luby Contreras Keller Williams Realty Partner

  40 Linden Ave, Ossining, NY 10562
• 

  $925,000 Sold Oct 06, 2025

  35 Mystic Dr, Ossining, NY 10562

  • 2 Beds
  • 3.5 Baths
  • 2,700 Sq Ft
  • Built 1996

  Last Sold Summary

  • 8% Above List Price
  • $343/SF
  • 20 Days On Market

  Last Listing Agent Wendy Nolan Houlihan Lawrence Inc.

  35 Mystic Dr, Ossining, NY 10562
• 

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft

  123 S Highland Ave Unit B5, Ossining, NY 10562

  123 S Highland Ave Unit B5, Ossining, NY 10562
• 

  

  /14

  $240,000

  • 2 Beds
  • 1 Bath
  • 951 Sq Ft

  135 Main St Unit 203, Ossining, NY 10562

  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 of "fair and affordable"

  Igor Krasnoperov Rising Star Realty

  135 Main St Unit 203, Ossining, NY 10562
• 

  $485,000 Sold Mar 21, 2025

  20 Knoll View, Ossining, NY 10562

  • 3 Beds
  • 3.5 Baths
  • 1,500 Sq Ft
  • Built 1988

  Last Sold Summary

  • 3% Above List Price
  • $323/SF
  • 35 Days On Market

  Current Estimated Value $492,812

  Last Listing Agent Erika King YourHomeSold Guaranteed Realty

  20 Knoll View, Ossining, NY 10562
• 

  Est $945,265 Not Listed For Sale

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

  45 Mystic Dr, Ossining, NY 10562

  45 Mystic Dr, Ossining, NY 10562
• 

  

  /38

  $849,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,242 Sq Ft

  1376 Spring Valley Rd, Ossining, NY 10562

  Story book setting found. Nestled within the Teatown area with pond and gardens galore. The magical setting is only enhanced by the spectacular home. The kitchen is the ideal center of the home with breakfast bar, timeless updates and open airy floorplan. Entertain your guests while overlooking the water and grounds. When a screened-in porch has an outdoor fireplace, the use is year-round. The

  Douglas Dill Houlihan Lawrence Inc.

  1376 Spring Valley Rd, Ossining, NY 10562
• 

  $550,000 Sold Mar 20, 2025

  45 Gordon Ave, Briarcliff Manor, NY 10510

  • 4 Beds
  • 3 Baths
  • 1,976 Sq Ft
  • Built 1938

  Last Sold Summary

  • 4% Below List Price
  • $278/SF
  • 43 Days On Market

  Last Listing Agent John Piazza RE/MAX Classic Realty

  45 Gordon Ave, Briarcliff Manor, NY 10510
• 

  Est $505,693 Not Listed For Sale

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

  1210 Eagle Bay Dr, Ossining, NY 10562

  1210 Eagle Bay Dr, Ossining, NY 10562
• 

  

  /33

  $899,222

  • 4 Beds
  • 2.5 Baths
  • 3,551 Sq Ft

  1 Noel Dr, Ossining, NY 10562

  Sprawling Cape Cod style home with first floor primary suite on a fabulous, private setting. Kitchen has stainless appliances and stone counters, formal dining room has large bay window looking out at the fenced-in property, and living room has high ceilings and a fireplace. Sun Room off the kitchen has 3 skylights and the covered patio off the kitchen overlooks the lush landscaping, backing up

  Mark Seiden Mark Seiden Real Estate Team

  1 Noel Dr, 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

  Last Listing Agent Suzan Zeolla Houlihan Lawrence Inc.

  407 Glenwood Dr, Briarcliff Manor, NY 10510
• 

  Est $162,000 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 890 Sq Ft

  129 S Highland Ave Unit B4, Ossining, NY 10562

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

  

  /36

  $938,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 3,300 Sq Ft

  2 Oak Hill Terrace, Ossining, NY 10562

  Nestled on one of Ossining Village’s most coveted streets, this quintessential 1920s Colonial exudes timeless charm while embracing modern luxury. Just a short stroll to town, the home offers sweeping Hudson River views from every floor. Vintage details blend seamlessly with thoughtful updates, including a chef’s kitchen with top-tier stainless steel appliances and three exquisitely renovated

  Heather Bouza William Raveis-New York, LLC

  2 Oak Hill Terrace, 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
• 

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 813 Sq Ft

  123 S Highland Ave Unit B4, Ossining, NY 10562

  123 S Highland Ave Unit B4, Ossining, NY 10562

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