Ossining, NY Homes

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  /39

  $549,000 Pending

  • 2 Beds
  • 2.5 Baths
  • 1,470 Sq Ft

  707 Eagle Bay Dr, Ossining, NY 10562

  Carefree Rivertown Living Surrounded by Nature – Rare End Unit with 2 Deeded GaragesEnjoy effortless living in this bright and spacious end-unit townhome. 2-bedroom, 2.5-bath home featuring a fireplace and a beautiful sunroom that feels like a private treehouse escape. Perfect for reading, relaxing, or enjoying the view year-round.A rare find, this home includes two deeded detached

  

  Maria Teresa Duguet

  Houlihan Lawrence Inc.

  (914) 758-0173

  707 Eagle Bay Dr, Ossining, NY 10562
• Explore Ossining

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  /27

  $4,200 per month

  • 2 Beds
  • 2 Baths
  • 1,310 Sq Ft
  • Apartment for Rent

  333 N State Rd Unit 20E, Briarcliff Manor, NY 10510

  NEW PRICE - INCREDIBLE VALUE to move right into this beautifully gut-renovated 2-bedroom, 2-bathroom apartment in the heart of Briarcliff Manor. This spacious and sunny one-level home features a modern open-concept layout with a brand-new kitchen outfitted with smart stainless steel and white glass appliances, sleek cabinetry, and Porcelanosa tile finishes. The expansive living and dining area

  

  Hillary Landau

  Compass Greater NY, LLC

  (914) 540-8354

  333 N State Rd Unit 20E, Briarcliff Manor, NY 10510
• 

  $310,000 Sold Nov 06, 2025

  • 1,100 Sq Ft
  • $282/SF
  • 32 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1961

  95 Charter Cir, Ossining, NY 10562

  If you are looking for an extra large 2 bedroom unit with private entrance and no steps, look no further! This completely updated end unit has the benefits of being on one level, with a sliding door to a private grassy area, along with a front patio, a large laundry room with stackable front loaders in the unit, and an additional bonus room that can be a home office or serve other purposes.

  Mark Seiden Mark Seiden Real Estate Team

  95 Charter Cir, Ossining, NY 10562
• 

  Est $151,000 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft

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

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

  

  

  /19

  $505,000 Pending

  • 2 Beds
  • 1 Bath
  • 1,151 Sq Ft

  5 Glen St, Ossining, NY 10562

  Imagine the lifestyle you can create in this appealing Victorian, where a welcoming rocking chair front porch sets the tone and modern updates enhance timeless charm. Unwind in the inviting living room with gas fireplace, custom built-in and elegant bow window. Cook and dine with ease in the beautifully renovated eat-in kitchen. Thoughtful touches like radiant heated floors, pot filler, and

  

  Sheri Wolfe

  Berkshire Hathaway HS NY Prop

  (914) 635-2594

  5 Glen St, Ossining, NY 10562
• 

  

  /50

  $3,150 - $4,995 per month

  Harbor Square

  1 - 2 Beds

  3 Westerly Rd, Ossining, NY 10562

  1 month free on select units.

  3 Westerly Rd, Ossining, NY 10562
• 

  $680,000 Sold Oct 31, 2025

  • 2,000 Sq Ft
  • $340/SF
  • 82 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1902

  33 Ann St, Ossining, NY 10562

  Two-Family Home!! Here is a wonderful opportunity for a picturesque Colonial home near the Hudson River in desirable Ossining. Originally built in 1902, the charming clapboard property with its cute green shutters has since been expanded and is currently configured as a two-family residence. The possibilities are endless! The home presents beautifully with its postcard-perfect fenced front yard

  Matthew Bizzarro Bizzarro Agency, LLC

  33 Ann St, Ossining, NY 10562
• 

  Est $890,163 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 3,240 Sq Ft

  23 Mystic Dr, Ossining, NY 10562

  23 Mystic Dr, Ossining, NY 10562
• 

  

  /23

  $199,000 Pending

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft

  147 Charter Cir Unit 147, Ossining, NY 10562

  Step into this fabulous duplex townhouse-style cooperative, boasting its own private entrance on a picturesque, tree-lined street. The main level unfolds into an inviting layout, featuring a bright and spacious living room, a dedicated dining room perfect for entertaining, and a well-appointed kitchen. Ascend to the second floor where you'll discover two generously sized bedrooms, each offering

  

  Sherry Wiggs

  Houlihan Lawrence Inc.

  (914) 647-6619

  147 Charter Cir Unit 147, Ossining, NY 10562
• 

  

  /3

  $2,350 per month

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

  6 William St Unit 2, Ossining, NY 10562

  Wow! Beautiful, freshly painted 2nd floor 2-bedroom, 1 bath apartment with living room, dining area, and kitchen. All new flooring throughout! The kitchen has been freshly painted with a new tile backsplash and new flooring. Nice front porch and shared patio area out back. One parking spot is included in the rental, with an additional parking spot available at an extra monthly cost. Near public

  The Raymond Team Keller Williams Realty Partner

  6 William St Unit 2, Ossining, NY 10562
• 

  $1,710,000 Sold Oct 29, 2025

  • 4,592 Sq Ft
  • $372/SF
  • 12 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1989

  23 Brookwood Dr, Briarcliff Manor, NY 10510

  Impeccably maintained and artfully styled, this four-bedroom, three-and-a-half-bath French Country Colonial marries refined elegance with effortless modern living. Step through the double front doors into a dramatic two-story foyer, where rich hardwood floors and graceful millwork introduce interiors that flow seamlessly from room to room. At the home’s heart, an open-concept core—living room

  Francie Malina Compass Greater NY, LLC

  23 Brookwood Dr, Briarcliff Manor, NY 10510
• 

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft

  94 Charter Cir Unit 94, Ossining, NY 10562

  94 Charter Cir Unit 94, Ossining, NY 10562
• 

  

  /16

  $150,000 Pending

  • 1 Bed
  • 1 Bath
  • 750 Sq Ft

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

  Welcome to your perfect home-away-from-the-hustle! Step into this beautifully maintained 750-square-foot haven featuring thoughtful design and abundant natural light throughout. The well-appointed kitchen with new appliances, and updated bathroom create a perfect foundation for daily living, while the spacious bedroom provides a peaceful retreat after busy days. Ossining offers the perfect

  

  Peter Raider

  Real Broker NY LLC

  (914) 908-6292

  117 S Highland Ave Unit 6J, Ossining, NY 10562
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  /24

  $1,839 - $3,400 per month

  Cortlandt Living

  Studio - 4 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

  24 Claremont Gardens, Ossining, NY 10562
• 

  $164,000 Sold Oct 29, 2025

  • 750 Sq Ft
  • $219/SF
  • 58 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1962

  131 S Highland Ave Unit A3, Ossining, NY 10562

  Back on the Market. Stunning Rivertown Apartment. This beautifully maintained, sunny, move-in ready 1-bedroom, 1-bathroom unit in Highland Terrace garden-style complex offers convenient access to the woods and hiking trail, perfect for nature lovers and outdoor enthusiasts. Amenities include an in-ground pool and basketball court, laundry and storage facilities, assigned parking and pet-friendly

  Amit Shah Compass Greater NY, LLC

  131 S Highland Ave Unit A3, Ossining, NY 10562
• 

  Not Listed For Sale

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

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

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

  

  /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
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  /26

  $1,850 per month

  • 1 Bath
  • 350 Sq Ft
  • Apartment for Rent

  12 Lincoln Place Unit 2a, Ossining, NY 10562

  Step into your own cozy retreat in the vibrant heart of Ossining, NY! This fully renovated studio apartment blends sleek modern living with timeless charm — perfect for anyone seeking comfort, convenience, and community. Enjoy a freshly updated interior with neutral tones that create a warm, welcoming atmosphere. The open layout maximizes space and light, making this studio feel airy and

  Christina DiMinno Julia B Fee Sothebys Int. Rlty

  12 Lincoln Place Unit 2a, Ossining, NY 10562
• 

  $425,000 Sold Oct 28, 2025

  • 1,688 Sq Ft
  • $252/SF
  • 6 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1912

  29 William St, Ossining, NY 10562

  This "diamond in the rough" opportunity only comes once in a lifetime! Assessor's office has this property listed as a 5-bedroom home, tons of potential here. Bring your toolbelt and hard hat and truly turn this into your dream home for the CHEAP or renovate and start your real estate portfolio the right way, with great income producing potential.

  Justin Landon Howard Hanna Rand Realty

  29 William St, Ossining, NY 10562
• 

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft

  14 Charter Cir, Ossining, NY 10562

  14 Charter Cir, Ossining, NY 10562
• 

  

  /50

  $1,320,000

  • 4 Beds
  • 3 Baths
  • 3,813 Sq Ft

  11 Knollwood Dr, Ossining, NY 10562

  Accepted offer. Enter through stately stone pillars and wrought iron gates to this exquisite Center Hall Colonial, perfectly set on nearly one acre of stunning, level, and fully fenced property. Every inch of this residence has been thoughtfully designed to offer an extraordinary combination of elegance, comfort, and functionality. The magnificent gourmet kitchen is a chef’s dream, featuring an

  

  Sherry Wiggs

  Houlihan Lawrence Inc.

  (914) 809-8240

  11 Knollwood Dr, Ossining, NY 10562
• 

  

  /18

  $2,299 - $2,995 per month

  Audubon Living

  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

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

  $450,000 Sold Oct 27, 2025

  • 1,200 Sq Ft
  • $375/SF
  • 42 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1989

  27 Knoll View, Ossining, NY 10562

  Welcome to 27 Knoll View a beautifully designed sun-filled townhome offering exceptional value just minutes from the Hudson River. Located in Ossining sought after Liberty Knolls community, this unit offers large windows, an updated kitchen, hardwood floors and a finished basement. Enjoy amenities such as the pool and clubhouse. Liberty Knolls is a well maintained pet friendly community known for

  James Hawkins D.L. Hawkins Realty LLC

  27 Knoll View, Ossining, NY 10562
• 

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft

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

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

  

  /27

  $199,900

  • 2 Beds
  • 1 Bath
  • 672 Sq Ft

  135 - 6 Highland Ave S Unit D1, Ossining, NY 10562

  Discover this charming, updated two-bedroom co-op in highly sought-after Highland Terrace. This unique unit offers the convenience of both a main building entrance and its own private entry. Inside, you'll find a spacious and bright primary bedroom with ample closet space, while the versatile second bedroom That is currently being utilized as a home office. Abundant windows fill the living areas

  

  Sherry Wiggs

  Houlihan Lawrence Inc.

  (914) 928-2634

  135 - 6 Highland Ave S Unit D1, Ossining, NY 10562
• 

  

  /21

  $2,675 per month

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft
  • Apartment for Rent

  79 Main St Unit 1W, Ossining, NY 10562

  Completely renovated in 2025, this charming two-bedroom, one-bath apartment blends modern style with village convenience. Located in the heart of Ossining, it’s just a short walk to the Metro-North train station—making your NYC commute easy and stress-free.Enjoy weekend strolls to the lively Farmers Market, local cafes, restaurants, and the scenic Hudson River waterfront. The apartment

  Altagracia Grace Patalano BHHS River Towns Real Estate

  79 Main St Unit 1W, Ossining, NY 10562
• 

  $680,000 Sold Oct 23, 2025

  • 2,900 Sq Ft
  • $234/SF
  • 87 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2001

  11C Piping Rock Dr, Ossining, NY 10562

  A/O CTS -Nestled at the end of the serene and private Piping Rock Drive, this stunning colonial home offers a perfect blend of elegance, comfort, and convenience. As you approach, the expansive driveway ensures ample parking, while the attached one-car garage provides seamless access to the property. To the side of the garage, a charming, covered patio invites you to enjoy morning coffee or

  Paige Castiello Keller Williams Realty Group

  11C Piping Rock Dr, Ossining, NY 10562
• 

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft

  43 Charter Cir, Ossining, NY 10562

  43 Charter Cir, Ossining, NY 10562
• 

  

  /35

  $1,950,000

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

  2 Shadow Tree Ln, Briarcliff Manor, NY 10510

  Why Compromise on Luxury? Simplify—and Still Have It All at Trump National Golf Club, Briarcliff ManorWelcome to this exceptional villa-style townhome, set within the prestigious, gated grounds of Trump National Golf Club in Briarcliff Manor. Offering the ultimate in convenience and elegance, this turnkey residence delivers a lifestyle of luxury—without compromise.Filled with

  

  Hillary Landau

  Compass Greater NY, LLC

  (914) 341-3203

  2 Shadow Tree Ln, Briarcliff Manor, NY 10510
• 

  

  /35

  $2,735 - $18,032 per month

  Terraces on the Hudson

  1 - 3 Beds

  217 N Highland Ave, Ossining, NY 10562

  Avalon Ossining, only 1 mile from the Ossining Metro-North Railroad Station, offers thoughtfully designed 1, 2, and 3 bedroom luxury apartments that include contemporary kitchens with Energy Star appliances, walk-in closets, and a washer/dryer. Community amenities include a state-of-the-art fitness center and outdoor swimming pool, on-site children’s play area, and outdoor grilling areas.

  217 N Highland Ave, Ossining, NY 10562
• 

  $653,000 Sold Oct 22, 2025

  • 1,837 Sq Ft
  • $355/SF
  • 19 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 2001

  407 Glenwood Dr, Briarcliff Manor, NY 10510

  Welcome to this lovely townhome located in the desirable Scarborough Glen community. This spacious 2-bedroom, 2.1-bath home offers a comfortable and versatile layout, ideal for modern living. The main level features a welcoming entry foyer with tiled flooring, recessed lighting, a powder room, and a hall closet. The eat-in kitchen boasts hardwood floors and a bright breakfast area. The adjacent

  Suzan Zeolla Houlihan Lawrence Inc.

  407 Glenwood Dr, Briarcliff Manor, NY 10510
• 

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft

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

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

  

  /50

  $1,350,000

  • 6 Beds
  • 7 Baths
  • 4,495 Sq Ft

  9 Gualtiere Ln, Ossining, NY 10562

  Panoramic Hudson River Views | Custom Architecture | Resort-Style Amenities |Discover an extraordinary sanctuary, where every detail has been carefully curated to create an unparalleled living experience. This architecturally stunning residence seamlessly blends sophisticated design with the natural beauty of its coveted river view location.Make a memorable entrance through the property’s

  Irina Fiorella Coldwell Banker Realty

  9 Gualtiere Ln, Ossining, NY 10562
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  /46

  $4,600 per month

  • 3 Beds
  • 2.5 Baths
  • 1,536 Sq Ft
  • House for Rent

  13 Yates Ave, Ossining, NY 10562

  Welcome home to this impeccable turnkey residence on a quiet, tree-lined street — a home that’s been completely gut renovated and finished to perfection. Every detail reflects quality craftsmanship, modern comfort, and effortless style.From the moment you arrive, the manicured front lawn and beautiful stone steps lead you into a warm and welcoming entryway. On the main level, you’ll find

  Michael A Tarallo Giner Real Estate Inc.

  13 Yates Ave, Ossining, NY 10562
• 

  $199,999 Sold Oct 21, 2025

  • 800 Sq Ft
  • $250/SF
  • 18 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1950

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

  This spacious end unit is calling you home! Enjoy one floor of easy living in sought after Briarcliff Manor! Whether you are starting out or buying down, this complex is clean, convenient and close to the vibrant village. This coop offers a flexible floor plan. There is a dining room off the kitchen that can be converted back into an office, nursery or guest space by closing a wall and adding

  Loretta Fleming Chiavetta Coldwell Banker Realty

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

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 959 Sq Ft

  121 S Highland Ave Unit L1, Ossining, NY 10562

  121 S Highland Ave Unit L1, Ossining, NY 10562
• 

  

  /33

  $550,000 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,264 Sq Ft

  110 Pine Ave, Ossining, NY 10562

  Fall in love with this charming colonial-style home offering endless potential to make it your own. As you enter, you’re greeted by a welcoming enclosed front porch, perfect for enjoying morning coffee or adding a touch of seasonal charm. Inside, the spacious living room flows effortlessly into the dining area and office/den, creating a comfortable space for everyday living. The kitchen features

  Ana Bermeo Keller Williams Realty Partner

  110 Pine Ave, Ossining, NY 10562
• 

  

  /15

  $2,299 - $3,195 per month

  WaterView Living

  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,

  42 Cedar Ln, Ossining, NY 10562
• 

  $751,000 Sold Oct 21, 2025

  • 1,784 Sq Ft
  • $421/SF
  • 27 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1986

  201 Horseshoe Cir, Ossining, NY 10562

  MOVE-IN-READY – nothing to do but unpack! Absolutely stunning & rare end unit in desirable Fox Hill community, C model townhome, with 2-car garage and finished basement. This home boasts hardwood floors throughout, a white gourmet kitchen w/quartz countertops & stainless-steel appliances, offering a brand new refrigerator, recessed lighting, and 2.5 updated bathrooms. Main level offers a

  Elvira Aloia Corcoran Legends Realty

  201 Horseshoe Cir, Ossining, NY 10562
• 

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft

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

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

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