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

  (914) 326-0785

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

• 

  

  

  /26

  $3,800 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 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 sense of space and separation rarely

  

  Sara Reel

  Julia B Fee Sothebys Int. Rlty

  (914) 354-3157

  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 $514,485

  Last Listing Agent Maureen McEnroe Joyce Realty Corp

  8 Samstag Ave, Ossining, NY 10562
• 

  Est $159,000

  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

  • 9% Below List Price
  • $194/SF
  • 27 Days On Market

  • Last Sold Price $174,900
  • Apr 08, 2024

  Last Listing Agent Evelyn Romero BHHS River Towns Real Estate
• 

  

  

  /45

  $525,000

  Pending

  • 1 Bed
  • 1.5 Baths
  • 1,152 Sq Ft

  14 Bridle Path Rd, Ossining, NY 10562

  Welcome to this tastefully updated one-bedroom townhouse with loft in the highly desirable Fox Hills community. This inviting home features two skylights that fill the space with natural light, beautiful hardwood floors throughout, and a one-car attached garage. The updated kitchen is appointed with Corian countertops and stainless steel appliances, seamlessly opening to a formal dining area with

  

  Clayton Jeffrey

  Keller Williams NY Realty

  (914) 279-8998

  14 Bridle Path Rd, Ossining, NY 10562
• 

  

  /50

  Starting at $2,650 Per Month

  • 1 - 2 Beds

  3 Westerly Rd, Ossining, NY 10562

  1 month free on select units.

  Harbor Square

  (914) 685-5764

  

  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 $1,183,649

  Last Listing Agent Eric Lebenson ERA Insite Realty Services

  32 Waterview Dr, Ossining, NY 10562
• 

  Est $378,000

  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

  • 13% Above List Price
  • $212/SF
  • 93 Days On Market

  • Last Sold Price $335,000
  • Jan 03, 2025

  Last Listing Agent Eric Lebenson ERA Insite Realty Services
• 

  

  /48

  $1,535,000

  Pending

  • 5 Beds
  • 4.5 Baths
  • 4,155 Sq Ft

  96 Cherry Hill Ct, Briarcliff Manor, NY 10510

  Spacious Contemporary Colonial tucked away on a quiet cul-de-sac in the Briarcliff Manor School District. Offering over 4,000 square feet of living space, this expansive 5-bedroom home is set on .91 beautifully landscaped acres with exceptional privacy and sweeping treetop views. A dramatic two-story entry foyer welcomes you with abundant natural light. The updated gourmet chef’s kitchen is the

  

  Sherry Wiggs

  Houlihan Lawrence Inc.

  (914) 359-3787

  96 Cherry Hill Ct, Briarcliff Manor, NY 10510
• 

  

  /17

  Starting at $2,215 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

  (845) 402-2278

  

  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 $892,684

  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

  • $211/SF
  • 80 Days On Market

  • Last Sold Price $200,000
  • Jul 13, 2023

  Last Listing Agent Kimberly Renzi Coldwell Banker Realty
• 

  

  /26

  $245,000

  Pending

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft

  9 Geneva Rd Unit 9, Ossining, NY 10562

  Welcome to this beautifully updated co-op in the sought-after High Meadow complex, where timeless style meets everyday convenience. The main level offers a bright, airy flow with an inviting living room, dining area, and a beautifully renovated kitchen featuring new cabinetry, quartz countertops, and a classic subway tile backsplash. Barn doors add character and charm while opening to a laundry

  

  Valerie Cascione

  Compass Greater NY, LLC

  (914) 685-5423

  9 Geneva Rd Unit 9, Ossining, NY 10562
• 

  

  /14

  Starting at $2,215 Per Month

  • 1 - 2 Beds

  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

  (845) 671-5778

  

  38 1/2 Wolden Rd, 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 $378,000

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

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

  Not Listed For Sale

  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

  • $252/SF
  • 80 Days On Market

  • Last Sold Price $265,000
  • Jul 21, 2023

  Last Listing Agent Donna McKenna Edlund Coldwell Banker Realty
• 

  

  /38

  $899,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 2,596 Sq Ft

  3 Birch Ct, Ossining, NY 10562

  Set on a quiet cul-de-sac with seasonal river views and unforgettable sunsets, this beautifully maintained Colonial offers the perfect balance of style, comfort, and everyday ease. Built in 2004 and gently lived in, the home is filled with natural light, highlighted by high ceilings, generous proportions, and a seamless, inviting flow.The main level features formal living and dining rooms, a

  

  Valerie Cascione

  Compass Greater NY, LLC

  (914) 290-5256

  3 Birch Ct, Ossining, NY 10562
• 

  

  /24

  Starting at $2,000 Per Month

  • Studio - 2 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

  (845) 523-6636

  

  24 Claremont Gardens, 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 $675,270

  Last Listing Agent Susan Strawgate Code Houlihan Lawrence Inc.

  107 Glenwood Dr, Briarcliff Manor, NY 10510
• 

  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

  • $253/SF
  • 19 Days On Market

  • Last Sold Price $227,500
  • Nov 28, 2023

  Last Listing Agent George Khury Keller Williams Realty Group
• 

  

  /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

  (914) 604-4954

  177 Quinn Rd, 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

  (914) 221-0453

  

  87 Hawkes Ave, 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 $857,764

  Last Listing Agent Daniella Ingenito Compass Greater NY, LLC

  31 Murray Ln, Ossining, NY 10562
• 

  Not Listed For Sale

  310 N State Rd Unit 1C, Briarcliff Manor, NY 10510

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft
  • Built 1950

  310 N State Rd Unit 1C, Briarcliff Manor, NY 10510

  Last Sold Summary

  • $221/SF
  • 182 Days On Market

  • Last Sold Price $210,000
  • Nov 02, 2023

  Last Listing Agent Michelle Drenga Weichert Realtor Future Vision
• 

  

  /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

  (914) 928-2662

  620 Sleepy Hollow Rd, Briarcliff Manor, NY 10510
• 

  

  /119

  $2,250 - $7,250

  Total Monthly Price

  • 1 - 5 Beds
  • 4 Baths
  • 680 Sq Ft
  • House for Rent

  275 Croton Dam Rd, 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, 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 $531,506

  Last Listing Agent Tim Rothman Compass Greater NY, LLC

  14 Gates Ave, 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

  • $242/SF
  • 20 Days On Market

  • Last Sold Price $230,000
  • Jan 12, 2024

  Last Listing Agent SANDRA MAHON BHHS Hudson Valley Properties
• 

  

  /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

  (914) 353-4296

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

  

  /119

  $2,250 - $7,250

  Total Monthly Price

  • 1 - 5 Beds
  • 4 Baths
  • 680 Sq Ft
  • House for Rent

  275 Croton Dam Rd, 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, 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 $865,819

  Last Listing Agent Jody Toth Corcoran Legends Realty

  106 Mystic Dr, 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

  • $274/SF
  • 18 Days On Market

  • Last Sold Price $260,000
  • May 06, 2024

  Last Listing Agent Mark Seiden Mark Seiden Real Estate Team
• 

  

  /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 split-level 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, the property delivers a peaceful, estate-like setting. Inside, sun-filled, spacious rooms

  

  Maria Teresa Duguet

  Houlihan Lawrence Inc.

  (914) 219-6613

  77 Central Dr, Briarcliff Manor, NY 10510
• 

  

  /119

  $2,250 - $7,250

  Total Monthly Price

  • 1 - 5 Beds
  • 4 Baths
  • 680 Sq Ft
  • House for Rent

  275 Croton Dam Rd, 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, 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 $1,038,209

  Last Listing Agent Jeanne Beckley Howard Hanna Rand Realty

  144 Hungerford Rd N, Briarcliff Manor, NY 10510
• 

  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

  • $193/SF
  • 16 Days On Market

  • Last Sold Price $185,000
  • Oct 07, 2024

  Last Listing Agent Amarish J. Khan Apollo Real Properties, Inc.
• 

  

  /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

  (914) 867-0383

  143 N Highland Ave, Ossining, NY 10562
• 

  

  /50

  $23,000 Per Month

  • 4 Beds
  • 2.5 Baths
  • 2,592 Sq Ft
  • House for Rent

  137 Cedar Ln, Ossining, NY 10562

  Discover a refined hilltop retreat in the heart of the Hudson Valley. This fully furnished 4-bedroom, 2.5-bath mid-century modern residence has been fully renovated and offers panoramic Hudson River and Palisades views. Floor-to-ceiling windows fill the open-concept living spaces with natural light, while a chef’s kitchen with premium appliances anchors the home. Spa-inspired baths and designer

  Vitaly Isaacs Magic Of Great Neck Realty Inc

  137 Cedar Ln, Ossining, NY 10562
• 

  $630,000

  Sold Dec 09, 2025

  10 Mohegan Rd, Ossining, NY 10562

  • 3 Beds
  • 1.5 Baths
  • 1,362 Sq Ft
  • Built 1929

  Last Sold Summary

  • $463/SF
  • 38 Days On Market

  Current Estimated Value $638,417

  Last Listing Agent Francie Malina Compass Greater NY, LLC

  10 Mohegan Rd, Ossining, NY 10562
• 

  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

  • $200/SF
  • 28 Days On Market

  • Last Sold Price $179,900
  • Feb 08, 2024

  Last Listing Agent Debra Goodwin Corcoran Legends Realty

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