Ossining, NY Homes

• 

  

  

  /41

  $1,800,000

  Pending

  • 5 Beds
  • 5 Baths
  • 4,223 Sq Ft

  16 Hall Rd, Briarcliff Manor, NY 10510

  Welcome to 16 Hall Rd, where the cul-de-sac is quiet enough to stroll, and the house itself feels like it's been designed just for you. You've been thinking about this move for a while now. Maybe the city apartment that once felt exciting has started to feel a little tight. Maybe you've been eyeing bigger spaces in the suburbs, but have not found the one that checks every box without needing a

  

  Hillary Landau

  Compass Greater NY, LLC

  16 Hall Rd, Briarcliff Manor, NY 10510
• Explore Ossining

• 

  

  

  /27

  $3,700 Per Month

  • 1 Bed
  • 1.5 Baths
  • 1,452 Sq Ft
  • Townhouse for Rent

  8 Davids Ln, Ossining, NY 10562

  Rare and expansive 1-bedroom triplex with office/den/finished basement offering approximately 1,450 square feet of living space, featuring a large bonus room ideal for a home office, den, or entertaining space. This sun-filled residence enjoys beautiful natural light throughout, with morning sun in the kitchen and warm sunset light in the living room. The multi-level layout provides a unique

  

  Sara Reel

  Julia B Fee Sothebys Int. Rlty

  8 Davids Ln, Ossining, NY 10562
• 

  $510,000

  Sold Sep 26, 2025

  8 Samstag Ave, Ossining, NY 10562

  • 3 Beds
  • 1 Bath
  • 1,031 Sq Ft
  • Built 1922

  Last Sold Summary

  • 2% Above List Price
  • $495/SF
  • 105 Days On Market

  Current Estimated Value $518,554

  Last Listing Agent Maureen McEnroe Joyce Realty Corp

  8 Samstag Ave, Ossining, NY 10562
• 

  Est $158,000

  Not Listed For Sale

  121 S Highland Ave Unit 2B, Ossining, NY 10562

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Built 1964

  121 S Highland Ave Unit 2B, Ossining, NY 10562

  Last Sold Summary

  • 27 Days On Market
• 

  

  

  /42

  $1,750,000

  Pending

  • 5 Beds
  • 3.5 Baths
  • 4,392 Sq Ft

  177 Quinn Rd, Briarcliff Manor, NY 10510

  177 Quinn Road is the kind of home you stop in front of and just know. Set on a flat, open 1.3 acres in the heart of Briarcliff Manor, this five-bedroom, three-and-a-half-bathroom home offers over 4,300 square feet of generous, well-loved living space, the sort of place where every room has a purpose, and every corner has been cared for. Step inside and the layout greets you the way a home

  

  Hillary Landau

  Compass Greater NY, LLC

  177 Quinn Rd, Briarcliff Manor, NY 10510
• 

  

  /50

  Starting at $2,750 Per Month

  • 1 - 2 Beds

  3 Westerly Rd, Ossining, NY 10562

  1 month free on select units.

  Harbor Square

  

  3 Westerly Rd, Ossining, NY 10562
• 

  $1,210,000

  Sold Sep 19, 2025

  32 Waterview Dr, Ossining, NY 10562

  • 4 Beds
  • 2.5 Baths
  • 3,246 Sq Ft
  • Built 2002

  Last Sold Summary

  • 8% Above List Price
  • $373/SF
  • 34 Days On Market

  Current Estimated Value $1,184,345

  Last Listing Agent Eric Lebenson ERA Insite Realty Services

  32 Waterview Dr, Ossining, NY 10562
• 

  Est $432,000

  Not Listed For Sale

  16 Rockledge Ave Unit 7J-2, Ossining, NY 10562

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

  16 Rockledge Ave Unit 7J-2, Ossining, NY 10562

  Last Sold Summary

  • 93 Days On Market
• 

  

  /10

  $4,000,000

  Pending

  • Land
  • 15.55 Acres
  • $257,235 per Acre

  620 Sleepy Hollow Rd, Briarcliff Manor, NY 10510

  Discover the potential of 620 Sleepy Hollow Rd, an expansive 15.55-acre parcel of raw land in the picturesque Briarcliff Manor. This unique property offers a rare opportunity for buyers seeking to create their dream estate or invest in a prime location. With over 677,358 square feet, this lot provides ample space for various development possibilities, whether you envision a private residence, a

  

  Peter Raider

  Real Broker NY LLC

  620 Sleepy Hollow Rd, Briarcliff Manor, NY 10510
• 

  

  /17

  Starting at $2,400 Per Month

  • 1 - 2 Beds

  42 Cedar Ln, Ossining, NY 10562

  Waterview Living, located in Ossining NY, offers beautiful views of the Hudson River, with updated apartments and wonderful amenities. The property is situated between major highways, easy access to Metro North, and a short distance from the bustling downtown area of Ossining. There is much to do and see in this historic Rivertown. With local restaurants and the Sing Sing Kill Brewery downtown,

  WaterView Living

  

  42 Cedar Ln, Ossining, NY 10562
• 

  $870,000

  Sold Feb 12, 2026

  40 Magnolia Rd, Briarcliff Manor, NY 10510

  • 3 Beds
  • 3 Baths
  • 2,614 Sq Ft
  • Built 1961

  Last Sold Summary

  • 3% Below List Price
  • $333/SF
  • 83 Days On Market

  Current Estimated Value $890,945

  Last Listing Agent Denyse Fecteau Denyse M. Fecteau

  40 Magnolia Rd, Briarcliff Manor, NY 10510
• 

  Not Listed For Sale

  94 Charter Cir Unit 94, Ossining, NY 10562

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

  94 Charter Cir Unit 94, Ossining, NY 10562

  Last Sold Summary

  • 80 Days On Market
• 

  

  /38

  $249,999

  Pending

  • 1 Bed
  • 1 Bath
  • 736 Sq Ft

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

  Perched gracefully above the majestic Hudson River, this beautifully renovated one-bedroom home is ready to welcome you in. Nestled within the highly sought-after, gated Scarborough Manor community, you’ll be greeted by the gatekeeper each time you arrive—an immediate sense of comfort and care. This sun-soaked, south-facing unit feels bright and uplifting from the moment you step inside.

  

  Loretta Fleming Chiavetta

  Coldwell Banker Realty

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

  

  /14

  Starting at $2,215 Per Month

  • 1 Bed

  38 1/2 Wolden Rd, Ossining, NY 10562

  Audubon Living is located in Ossining, a beautiful Rivertown in Northern Westchester. The property offers close proximity to Metro North and major highways for convenient commuting. Audubon Living is located in the residential area of Ossining, close to the High School, and a short distance from downtown, which offers many local restaurants, brewery, and the historical Aqueduct Trail. There are

  Audubon Living

  

  38 1/2 Wolden Rd, Ossining, NY 10562
• 

  $386,000

  Sold Jun 05, 2026

  16 Rockledge Ave Unit 6K-2, Ossining, NY 10562

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

  Last Sold Summary

  • 9% Above List Price
  • $244/SF
  • 36 Days On Market

  Last Listing Agent Mark Seiden Mark Seiden Real Estate Team

  16 Rockledge Ave Unit 6K-2, Ossining, NY 10562
• 

  Not Listed For Sale

  338 N State Rd Unit 3F, Briarcliff Manor, NY 10510

  • 2 Beds
  • 2 Baths
  • 1,050 Sq Ft
  • Built 1950

  338 N State Rd Unit 3F, Briarcliff Manor, NY 10510

  Last Sold Summary

  • 80 Days On Market
• 

  

  /44

  $599,000

  Pending

  • 3 Beds
  • 3 Baths
  • 1,668 Sq Ft

  41 Clinton Ave, Ossining, NY 10562

  A charm-filled village home with river views, timeless details, and the ease of modern updates. This beautiful antique Colonial offers a rare blend of character, light, and convenience. From the moment you arrive, the Hudson River and Palisades set the tone, followed by a welcoming covered front porch and the warmth of beautiful woodwork and period details inside. The main level features an

  

  Valerie Cascione

  Compass Greater NY, LLC

  41 Clinton Ave, Ossining, NY 10562
• 

  

  /24

  Starting at $2,123 Per Month

  • 1 - 3 Beds

  24 Claremont Gardens, Ossining, NY 10562

  More than an apartment community, Cortlandt Ridge is your home. We offer affordable one, two, three, and four apartments and townhomes for rent in central Ossining, NY, near North Highland Avenue. Our homes are unique. Not only are they comfortable, they're stylish, too. Fully equipped featuring new kitchens and designer cabinetry. We have just what you need to live well in Westchester

  Cortlandt Living

  

  24 Claremont Gardens, Ossining, NY 10562
• 

  $379,000

  Sold Nov 25, 2025

  16 Rockledge Ave Unit 7D1, Ossining, NY 10562

  • 1 Bed
  • 1 Bath
  • 1,284 Sq Ft
  • Built 1970

  Last Sold Summary

  • $295/SF
  • 18 Days On Market

  Current Estimated Value $432,000

  Last Listing Agent Sarah Mirza Mulhall Julia B Fee Sothebys Int. Rlty

  16 Rockledge Ave Unit 7D1, Ossining, NY 10562
• 

  Not Listed For Sale

  14 Charter Cir, Ossining, NY 10562

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

  14 Charter Cir, Ossining, NY 10562

  Last Sold Summary

  • 19 Days On Market
• 

  

  /48

  $1,650,000

  • 5 Beds
  • 3.5 Baths
  • 4,317 Sq Ft

  77 Central Dr, Briarcliff Manor, NY 10510

  Set on 2.63 private acres on one of the Village’s most desirable streets, this Mediterranean-style home offers the perfect blend of privacy, space and convenience, just minutes to the business district, shops, dining and recreation. Surrounded by lawns, mature trees and lush natural landscaping, enjoy a peaceful, estate-like setting. Inside, sun-filled, spacious rooms create an inviting flow for

  

  Maria Teresa Duguet

  Houlihan Lawrence Inc.

  77 Central Dr, Briarcliff Manor, NY 10510
• 

  

  /17

  Starting at $2,950 Per Month

  • 1 - 2 Beds

  87 Hawkes Ave, Ossining, NY 10562

  CONTACT US DIRECTLY, NO BROKER FEE!!! WESTCHESTER MAGAZINE BUILDER AWARD FINALIST FOR BEST LUXURY MULTIFAMILY PROPERTY- PARTH KNOLLS is Luxury at your Leisure with the look and feel of single-family home living. Most apartments feature a study, which is perfect for your home office. Onsite indoor and assigned outdoor parking, spacious oversized units, In-unit full-sized Washer & Dryer in your

  Parth Knolls Apartments

  

  87 Hawkes Ave, Ossining, NY 10562
• 

  $640,000

  Sold Aug 18, 2025

  107 Glenwood Dr, Briarcliff Manor, NY 10510

  • 2 Beds
  • 2.5 Baths
  • 2,246 Sq Ft
  • Built 1996

  Last Sold Summary

  • 2% Above List Price
  • $285/SF
  • 12 Days On Market

  Current Estimated Value $675,783

  Last Listing Agent Susan Strawgate Code Houlihan Lawrence Inc.

  107 Glenwood Dr, Briarcliff Manor, NY 10510
• 

  Not Listed For Sale

  119 S Highland Ave Unit 6H, Ossining, NY 10562

  • 3 Beds
  • 2 Baths
  • 1,212 Sq Ft
  • Built 1965

  119 S Highland Ave Unit 6H, Ossining, NY 10562

  Last Sold Summary

  • 28 Days On Market
• 

  

  /46

  $1,095,000

  $105K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 3,867 Sq Ft

  27 Allapartus Cir, Ossining, NY 10562

  This distinctive Teatown compound made for gatherings and entertainment blends timeless craftsmanship with modern livability offering seclusion without sacrificing proximity to trains, parks, and major highways. Tucked at the end of a quiet cul-de-sac, this exceptional estate offers rare privacy on more than 3 picturesque acres while remaining conveniently close to everything. The stunning

  

  Mary Stetson

  Stetson Real Estate

  27 Allapartus Cir, Ossining, NY 10562
• 

  

  /19

  $4,000

  Total Monthly Price

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • Condo for Rent

  1600 Spring Valley Rd Unit 3BR, Ossining, NY 10562

  Discover peaceful living on the edge of Ossining, nestled beside a nature preserve — where quiet trails and the sounds of the natural world are right outside your door. This bright, thoughtfully designed 3-bedroom, 2-bathroom apartment offers the perfect blend of comfort and contemporary style — ideal for professionals, families, or anyone looking for a sophisticated place to call home in

  1600 Spring Valley Rd Unit 3BR, Ossining, NY 10562
• 

  $845,000

  Sold Oct 07, 2025

  31 Murray Ln, Ossining, NY 10562

  • 3 Beds
  • 4 Baths
  • 2,068 Sq Ft
  • Built 2003

  Last Sold Summary

  • 6% Above List Price
  • $409/SF
  • 15 Days On Market

  Current Estimated Value $871,849

  Last Listing Agent Daniella Ingenito Compass Greater NY, LLC

  31 Murray Ln, Ossining, NY 10562
• 

  Not Listed For Sale

  43 Charter Cir, Ossining, NY 10562

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

  43 Charter Cir, Ossining, NY 10562

  Last Sold Summary

  • 20 Days On Market
• 

  

  /42

  $799,000

  • 4 Beds
  • 3 Baths
  • 1,368 Sq Ft

  143 N Highland Ave, Ossining, NY 10562

  Legal 3-family home, located in the heart of Ossining. Excellent 1st time buyer opportunity to live in one and rent two other units and parking lot to help pay the mortgage or great investment opportunity for passive income and build equity. Prime location-close to all, easy access to transportation, downtown, and Hudson River waterfront.

  

  Abraham Mathew

  CENTURY 21 DAWNS GOLD

  143 N Highland Ave, Ossining, NY 10562
• 

  

  /20

  $2,300

  Total Monthly Price

  • 1 Bed
  • 1 Bath
  • 650 Sq Ft
  • Condo for Rent

  8 Old Albany Post Rd Unit A, Ossining, NY 10562

  Cozy one-bedroom, 1 full bathroom apartment for rent! Located in Ossining, NY. Close to 9A, and walking distance to Croton-on Husdon train station. Quiet neighborhood with plenty of hiking trails and 5mins away from supermarkets and stores.The apartment is 650 sq ft The apartment comes with new appliances, a washer, and dryer, and 1 parking spaces. Utilities are not included, the owner

  8 Old Albany Post Rd Unit A, Ossining, NY 10562
• 

  $500,000

  Sold Feb 24, 2026

  14 Gates Ave, Ossining, NY 10562

  • 3 Beds
  • 1 Bath
  • 1,276 Sq Ft
  • Built 1920

  Last Sold Summary

  • 17% Below List Price
  • $392/SF
  • 188 Days On Market

  Current Estimated Value $539,337

  Last Listing Agent Tim Rothman Compass Greater NY, LLC

  14 Gates Ave, Ossining, NY 10562
• 

  Not Listed For Sale

  211 Schrade Rd Unit 2C, Briarcliff Manor, NY 10510

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft
  • Built 1954

  211 Schrade Rd Unit 2C, Briarcliff Manor, NY 10510

  Last Sold Summary

  • 18 Days On Market
• 

  

  /24

  $550,000

  Pending

  • 6 Beds
  • 3 Baths
  • 2,276 Sq Ft

  41 Ellis Place, Ossining, NY 10562

  Legal 2-family opportunity in the heart of Ossining offering exceptional value, versatility, and upside potential. Priced at $550,000, this spacious property features a 5-bedroom, 3 full bath layout plus a separate studio apartment with its own private entrance—ideal for investors or owner-occupants looking to generate rental income. Set on a 7,405 sq ft lot, the home offers approximately 2,276

  

  Paula Esteves

  Century 21 Full Service Realty

  41 Ellis Place, Ossining, NY 10562
• 

  

  /67

  $5,250

  Total Monthly Price

  • 4 Beds
  • 3 Baths
  • 2,950 Sq Ft
  • House for Rent

  275 Croton Dam Rd Unit 275 Croton Dam Rd (Main House), Ossining, NY 10562

  This beautifully maintained 2017 stand-alone modern home offers privacy, space, and upscale living on just under an acre of level property. Featuring 4 bedrooms and 3 full bathrooms across 2,950 square feet, the home is thoughtfully designed with hardwood floors and an open-concept main level ideal for both everyday living and entertaining.The expansive living room flows seamlessly into a

  275 Croton Dam Rd Unit 275 Croton Dam Rd (Main House), Ossining, NY 10562
• 

  $1,225,000

  Sold Nov 14, 2025

  106 Mystic Dr, Ossining, NY 10562

  • 3 Beds
  • 3.5 Baths
  • 3,638 Sq Ft
  • Built 1998

  Last Sold Summary

  • 11% Above List Price
  • $337/SF
  • 9 Days On Market

  Current Estimated Value $855,789

  Last Listing Agent Jody Toth Corcoran Legends Realty

  106 Mystic Dr, Ossining, NY 10562
• 

  Not Listed For Sale

  121 S Highland Ave Unit L1, Ossining, NY 10562

  • 2 Beds
  • 1 Bath
  • 959 Sq Ft
  • Built 1964

  121 S Highland Ave Unit L1, Ossining, NY 10562

  Last Sold Summary

  • 16 Days On Market
• 

  

  /49

  $3,500,000

  • 10 Beds
  • 5.5 Baths
  • 8,881 Sq Ft

  335 Croton Dam Rd, Ossining, NY 10562

  Hidden behind a storybook cobblestone drive and set across 45 breathtaking acres in the heart of the Hudson Valley, this extraordinary 1932 Tudor estate is the kind of property that rarely comes to market - a true legacy compound offering cinematic beauty, complete privacy, and effortless access to Manhattan. For the city buyer dreaming of a refined countryside escape without sacrificing

  

  Hillary Landau

  Compass Greater NY, LLC

  335 Croton Dam Rd, Ossining, NY 10562
• 

  

  /19

  $2,600

  Total Monthly Price

  • 2 Beds
  • 1 Bath
  • 700 Sq Ft
  • Condo for Rent

  18 Everett Ave Unit 2 BR In-Unit Laundry Off St Parking, Ossining, NY 10562

  18 Everett Ave Unit 2 BR In-Unit Laundry Off St Parking, Ossining, NY 10562
• 

  $1,025,013

  Sold Sep 05, 2025

  144 Hungerford Rd N, Briarcliff Manor, NY 10510

  • 3 Beds
  • 2.5 Baths
  • 2,416 Sq Ft
  • Built 1998

  Last Sold Summary

  • 5% Above List Price
  • $424/SF
  • 13 Days On Market

  Current Estimated Value $1,060,427

  Last Listing Agent Jeanne Beckley Howard Hanna Rand Realty

  144 Hungerford Rd N, Briarcliff Manor, NY 10510
• 

  Not Listed For Sale

  119 S Highland Ave Unit 3E, Ossining, NY 10562

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Built 1965

  119 S Highland Ave Unit 3E, Ossining, NY 10562

  Last Sold Summary

  • 28 Days On Market

Showing Results 1 - 40, Page 1 of 18