Ossining, NY Homes

• 

  

  

  /39

  $549,000

  • 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) 326-0849

  707 Eagle Bay Dr, Ossining, NY 10562
• 

  Explore Ossining

• 

  

  

  /21

  $6,000 per month

  • 3 Beds
  • 3.5 Baths
  • 2,889 Sq Ft
  • Condo for Rent

  23 Deer Tree Ln, Briarcliff Manor, NY 10510

  Bright corner unit in Wyndcrest condominium. Hardwood floors on main and loft levels, eat-in kitchen overlooking charming front porch. Unit has three-bedrooms plus a family/exercise room in the lower level. Amenities include outdoor swimming pool, playground and basketball court. Unit available November 15th. NO pets or smokers allowed. Tenant pays all utilities and must carry Tenants'

  

  Maria Teresa Duguet

  Houlihan Lawrence Inc.

  (914) 996-6208

  23 Deer Tree Ln, Briarcliff Manor, NY 10510
• 

  $695,250 Sold Sep 12, 2025

  • 1,932 Sq Ft
  • $360/SF
  • 51 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1999

  18 Jenkins Ct, Ossining, NY 10562

  Tucked away at the end of a quiet cul-de-sac, this charming Cape cod is the kind of home that just feels good from the moment you arrive. With 4 bedrooms, and 3 full bathrooms, there’s plenty of room to spread out, grow, and make lasting memories. Step inside through a stylish glass-paneled front door and into a sunlit foyer that sets the tone for the rest of the house. The kitchen—spacious and

  Eva Casoria eXp Realty

  18 Jenkins Ct, Ossining, NY 10562
• 

  Est $222,000 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
• 

  

  

  /18

  $199,999

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft

  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

  (914) 350-3728

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

  

  /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
• 

  $660,000 Sold Sep 10, 2025

  • 2,100 Sq Ft
  • $314/SF
  • 17 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1985

  32 Spring Pond Dr, Ossining, NY 10562

  A beautifully maintained end-unit townhome nestled in the desirable Hamlet on Spring Pond community in Ossining. This spacious 2-bedroom, 2.5-bath residence offers the perfect blend of light-filled interiors, functional layout, and serene outdoor space. The main level features an inviting living room with a wood-burning fireplace, oversized windows, and direct access to a private deck—ideal for

  Erin Lee Keller Williams Realty Group

  32 Spring Pond Dr, Ossining, NY 10562
• 

  Est $850,427 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

  • 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
• 

  

  /50

  $2,550 - $6,250 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
• 

  $800,000 Sold Sep 09, 2025

  • 2,200 Sq Ft
  • $364/SF
  • 46 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1965

  19 Meadowbrook Dr, Ossining, NY 10562

  Enjoy sweeping Hudson River views from every room in this turnkey ranch. The sunlit living room features hardwood floors, a brick wood burning fireplace, and sliding doors to an expansive 62' balcony overlooking the river. Enjoy meals with a view from the dining area or new eat in kitchen complete with island breakfast bar, quartz countertops, stainless steel appliances, and recessed lighting. A

  Eric Stein RE/MAX Distinguished Hms.&Prop

  19 Meadowbrook Dr, Ossining, NY 10562
• 

  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
• 

  

  /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
• 

  

  /13

  $6,000 per month

  • 4 Beds
  • 2.5 Baths
  • 2,400 Sq Ft
  • House for Rent

  116 Meadow Rd, Briarcliff Manor, NY 10510

  Easy living ranch home with ADA compliant ramp at entrance. NO STEPS! Ramp to front door. Handicapped accessible. 1st floor Primary bedroom and bath, 2 additional bedrooms with full hall bath. Additional bedroom/office/study next to kitchen. Lower level has been completely refinished. New flooring and new doors! Beautifully updated new kitchen and bathrooms. Updated furnace and hot water heater.

  Diane Mezzatesta ERA Insite Realty Services

  116 Meadow Rd, Briarcliff Manor, NY 10510
• 

  $475,000 Sold Sep 09, 2025

  • 1,176 Sq Ft
  • $404/SF
  • 73 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1975

  612 Kemeys Ave Unit 12, Briarcliff Manor, NY 10510

  First floor unit with Hudson river views at pet-friendly Kemeys Cove offers a balcony to sit and enjoy river views and spectacular sunsets. This inviting home has an open modern layout designed for today’s lifestyle. The seamless flow between the living, dining, and kitchen areas are perfect for everyday living. The built-in seating in the dining area provides additional storage and the built-in

  Mark Seiden Mark Seiden Real Estate Team

  612 Kemeys Ave Unit 12, Briarcliff Manor, NY 10510
• 

  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
• 

  

  /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
• 

  

  /26

  $2,950 per month

  Apartment for Rent

  2 Beds

  1 Briarcliff Dr S, Ossining, NY 10562

  Beautiful, newly renovated apartment, granite counter top, heat and hot water are included. 5 minute drive to the Ossining or Croton metro north train stations.

  1 Briarcliff Dr S, Ossining, NY 10562
• 

  $1,025,013 Sold Sep 05, 2025

  • 2,416 Sq Ft
  • $424/SF
  • 13 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1998

  144 Hungerford Rd N, Briarcliff Manor, NY 10510

  AO 7/27, inspection 7/27. Impeccably maintained and tastefully updated Split Colonial offers an expansive yet intimate environment for comfortable living and great flow for entertaining. As you enter you will notice living room boasts gleaming hardwood flooring, crown molding, and flows nicely into newer kitchen with stainless steel appliances, quartz counters, and ample storage. Formal dining

  Jeanne Beckley Howard Hanna Rand Realty

  144 Hungerford Rd N, Briarcliff Manor, NY 10510
• 

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft

  14 Charter Cir, Ossining, NY 10562

  14 Charter Cir, 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
• 

  

  /21

  $2,950 per month

  • 2 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • Apartment for Rent

  3 Overton Rd Unit 1st Floor, Ossining, NY 10562

  Immaculate and move-in ready, this bright and spacious first-floor 2-bedroom apartment offers comfort and convenience in a beautifully maintained multi-family home. Enjoy central air, a full bath, a generous living room, dining room, and eat-in kitchen perfect for everyday living. Laundry hookup and additional storage are available in the basement.This home includes parking for two cars

  Deborah Cuiffo Coldwell Banker Realty

  3 Overton Rd Unit 1st Floor, Ossining, NY 10562
• 

  $912,000 Sold Sep 05, 2025

  • 2,050 Sq Ft
  • $445/SF
  • 41 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1970

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

  It doesn't get any better than this! You can't find these panoramic, year-round river views, this space and this new condition in Hudson Harbor or NYC for this price!!! One of a kind-completely renovated top-of-the line showpiece home--a huge 3 BR, corner unit with year-round unobstructed Hudson River Views from all Rooms! Vacation at home and watch the boats sail by. Private Balcony off Living

  Susan Strawgate Code Houlihan Lawrence Inc.

  16 Rockledge Ave Unit 5D-2, 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
• 

  

  /49

  $3,000,000 Pending

  • 5 Beds
  • 7.5 Baths
  • 9,783 Sq Ft

  41 Austin Place, Briarcliff Manor, NY 10510

  Nestled at the end of a serene cul-de-sac, this extraordinary custom-built home in Briarcliff Manor welcomes you with a grand tree-lined circular driveway. Spanning nearly 10,000 sq. ft., this home is a masterclass in luxury, craftsmanship, and thoughtful design.Step inside to discover a beautifully appointed main level, where a custom gourmet eat-in kitchen, complete with a butler’s pantry, sets

  

  Hillary Landau

  Compass Greater NY, LLC

  (914) 650-1828

  41 Austin Place, Briarcliff Manor, NY 10510
• 

  

  /35

  $3,061 - $15,054 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
• 

  $1,200,000 Sold Sep 05, 2025

  • 3,876 Sq Ft
  • $310/SF
  • 41 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1913

  125 Hawkes Ave, Ossining, NY 10562

  A peaceful escape awaits at 125 Hawkes Avenue. Tucked away on two lush acres, this charming Colonial-style home in Ossining welcomes you with warmth and serenity—a perfect full-time haven or relaxing weekend retreat just outside New York City. Outdoors, the property features a picturesque duck pond in the front yard and a fully fenced, private backyard—creating a tranquil oasis ideal for

  Francie Malina Compass Greater NY, LLC

  125 Hawkes Ave, 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
• 

  

  /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
• 

  

  /19

  $3,450 per month

  • 3 Beds
  • 1 Bath
  • 775 Sq Ft
  • Apartment for Rent

  13 Hunter St Unit 2, Ossining, NY 10562

  Welcome to 13 Hunter Street, Fully renovated 2nd floor apartment with an open layout in the kitchen/living room great for entertaining, and comfortable space for relaxing. The kitchen is fully equipped with Granite countertops, all new appliances and completely renovated.. Three bedrooms, one with Hudson River views with a built-in closet.This unit also has a washer and dryer,

  Janice Terry William Raveis Real Estate

  13 Hunter St Unit 2, Ossining, NY 10562
• 

  $485,000 Sold Sep 05, 2025

  • 1,526 Sq Ft
  • $318/SF
  • 127 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1902

  25 Belleview Ave, Ossining, NY 10562

  Choose your Hudson view from your front porch or second floor enclosed balcony in this superb village stunner. This 3 bedroom home has preserved its vintage charm, thanks to the owner's care, with an attractive and artistic color scheme, hardwood floors, sconce lights, and artisan early 20th century millwork. The kitchen has a breakfast bar, and a pass through to the formal dining room,

  J. Philip Faranda Howard Hanna Rand Realty

  25 Belleview Ave, Ossining, NY 10562
• 

  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
• 

  

  /33

  $550,000

  • 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
• 

  $999,000 Sold Sep 04, 2025

  • 3,418 Sq Ft
  • $292/SF
  • 41 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1985

  2 Greenwood Ct, Briarcliff Manor, NY 10510

  This stunning colonial-style home is located in the prestigious gated community of Rosecliff, offering both luxury and convenience.Step inside to find a grand living room with soaring cathedral ceilings and a wood-burning fireplace, creating a welcoming atmosphere perfect for entertaining or unwinding. Adjacent to the living space is a cozy study or den, also featuring its own wood-burning

  Christine Iarocci Coldwell Banker Realty

  2 Greenwood Ct, Briarcliff Manor, NY 10510
• 

  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
• 

  

  /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
• 

  

  /18

  $3,400 per month

  • 3 Beds
  • 2 Baths
  • 1,184 Sq Ft
  • Apartment for Rent

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

  Welcome to 119 S Highland Avenue, Unit 3D, located in the charming village of Ossining, NY. This spacious three-bedroom, two-bathroom condominium offers a perfect blend of comfort and convenience, ideal for those seeking a serene suburban lifestyle with easy access to urban amenities.Upon entering, you are greeted by a bright and open living space that seamlessly connects to the dining

  Cynthia Geiger Corcoran Legends Realty

  119 S Highland Ave Unit 3D, Ossining, NY 10562
• 

  $1,820,000 Sold Sep 03, 2025

  • 7,044 Sq Ft
  • $258/SF
  • 27 Days On Market

  • 4 Beds
  • 5.5 Baths
  • Built 1993

  94 Hirst Rd, Briarcliff Manor, NY 10510

  Commanding Presence! Majestic, exquisite and private! Distinctively designed and constructed Colonial in 1993, is a pure perfection. This outstanding home boasts beautifully proportioned rooms with the highest quality and sophistication, an open floor plan accented by soaring ceilings and grand two-story entryway, 3 fireplaces, extraordinary state-of-art-kitchen with center-island and top of

  Alicja Bohmrich Houlihan Lawrence Inc.

  94 Hirst Rd, Briarcliff Manor, NY 10510
• 

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 959 Sq Ft

  119 S Highland Ave Unit 2E, Ossining, NY 10562

  119 S Highland Ave Unit 2E, Ossining, NY 10562

Showing Results 1 - 40, Page 1 of 18