11,370

Ossining, NY Homes

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  • 54 Lincoln Ave, Ossining, NY 10562
    54 Lincoln Ave, Ossining, NY 10562
    54 Lincoln Ave, Ossining, NY 10562
    /31

    $699,000 Pending

    • 4 Beds
    • 3 Baths
    • 2,205 Sq Ft

    54 Lincoln Ave, Ossining, NY 10562

    Spacious Custom Built 4 Bedroom Home Near Veteran’s Park Ideal for Comfortable Living and Entertaining. Discover the perfect blend of space, comfort, and lifestyle in this large custom built 4 bedroom home. Tucked in a desirable neighborhood just minutes from Veteran’s Park, this property offers a rare combination of privacy and accessibility, making it ideal for families, professionals, or

    Janet Brand Houlihan Lawrence Inc.

    54 Lincoln Ave, Ossining, NY 10562
  • 10 Crest Dr, Briarcliff Manor, NY 10510

    $749,000 Sold Jul 30, 2025

    • 1,767 Sq Ft
    • $424/SF
    • 39 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1928

    10 Crest Dr, Briarcliff Manor, NY 10510

    Set on a picturesque, tree-lined street in the highly sought-after village of Briarcliff Manor, 10 Crest Drive is a striking Tudor brimming with curb appeal. Step into the screened-in porch, where a serene atmosphere invites you to relax and unwind for hours. Inside, you're welcomed by a charming foyer that leads into a beautifully appointed living room, featuring a wood-burning fireplace,

    Mark Nadler Berkshire Hathaway HS NY Prop

    10 Crest Dr, Briarcliff Manor, NY 10510
  • 369 Sleepy Hollow Rd, Briarcliff Manor, NY 10510
    369 Sleepy Hollow Rd, Briarcliff Manor, NY 10510
    369 Sleepy Hollow Rd, Briarcliff Manor, NY 10510
    /48

    $2,100,000 Pending

    • 5 Beds
    • 5.5 Baths
    • 3,981 Sq Ft

    369 Sleepy Hollow Rd, Briarcliff Manor, NY 10510

    Like a masterly crafted engaging jewel this grand 1927 Colonial farmhouse reveals delightful surprises at every turn. After nearly a century of stately gracious living the property has been luxuriously updated for the 21st century while preserving its timeless charm and refined architectural details. Whether hosting holiday gatherings, summer soirees or more intimate moments this sumptuous

    Stacy Levey William Raveis-New York, LLC

    369 Sleepy Hollow Rd, Briarcliff Manor, NY 10510
  • 24 Hollow Tree Rd, Briarcliff Manor, NY 10510

    $1,950,000 Sold Jul 30, 2025

    • 6,116 Sq Ft
    • $319/SF
    • 13 Days On Market
    • 5 Beds
    • 4.5 Baths
    • Built 1994

    24 Hollow Tree Rd, Briarcliff Manor, NY 10510

    **Welcome to 24 Hollow Tree Road – a sun-drenched Colonial tucked on a quiet cul-de-sac in the heart of Briarcliff Manor.**Set on nearly an acre of impeccably landscaped, flat property, this 5-bedroom, 4.5-bath residence offers a seamless blend of elegance, comfort, and functionality. Natural light floods the home through oversized windows, highlighting warm hardwood floors, soaring

    Hillary Landau Compass Greater NY, LLC

    24 Hollow Tree Rd, Briarcliff Manor, NY 10510
  • 19 1st Ave, Ossining, NY 10562
    19 1st Ave, Ossining, NY 10562
    19 1st Ave, Ossining, NY 10562
    /25

    $579,000 Pending

    • 3 Beds
    • 1 Bath
    • 1,512 Sq Ft

    19 1st Ave, Ossining, NY 10562

    Welcome to this delightful home nestled on a lovely, peaceful street in the village of Ossining. This charming property offers the perfect blend of classic charm and modern convenience, ideal for those looking to enjoy a serene lifestyle in a walking neighborhood.Step onto the inviting rocking chair front porch, a perfect spot to unwind and enjoy the tranquility of your surroundings.

    Valerie Cascione Compass Greater NY, LLC

    19 1st Ave, Ossining, NY 10562
  • 86 Charter Cir, Ossining, NY 10562

    $247,000 Sold Jul 30, 2025

    • 900 Sq Ft
    • $274/SF
    • 18 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1961

    86 Charter Cir, Ossining, NY 10562

    Welcome home to 86 Charter Circle. This bright, light and spacious unit is ready for you to make it your own in the sought after High Meadow garden style cooperative community. This unit offers a private entrance has hardwood floors throughout. Upon entry you have a cozy living room that is open to the dining area, updated kitchen with stainless steel appliances washer and dryer in the unit for

    Cristina Gameiro Howard Hanna Rand Realty

    86 Charter Cir, Ossining, NY 10562
  • 81 Glendale Rd, Ossining, NY 10562
    81 Glendale Rd, Ossining, NY 10562
    81 Glendale Rd, Ossining, NY 10562
    /37

    $1,090,000 Pending

    • 3 Beds
    • 2.5 Baths
    • 3,990 Sq Ft

    81 Glendale Rd, Ossining, NY 10562

    Shaky A/O, show for back up. Fantastic find for nature lovers seeking total stillness away form the City hustle and bustle, just a short 1 hr train ride from Manhattan! 14.5 wooded acres with beautiful stone outcroppings and a few clearings, suitable for chickens, goats and/or horses. The property has rustic outbuildings and walking paths that connect to Teatown trails. This home has large rooms

    Helena Macintyre North Country Sothebys Int Rlt

    81 Glendale Rd, Ossining, NY 10562
  • 246 Horseshoe Cir, Ossining, NY 10562

    $770,000 Sold Jul 29, 2025

    • 2,731 Sq Ft
    • $282/SF
    • 19 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1986

    246 Horseshoe Cir, Ossining, NY 10562

    Welcome to this beautifully maintained end-unit townhouse-style condo offering the perfect blend of space, style, and convenience! This bright and spacious 2-bedroom, 2.5-bath home features a 2-car attached garage and a thoughtfully designed floor plan. The main level boasts a welcoming living room with a cozy fireplace, a formal dining room, and a den—ideal for a home office or library. The

    Mary Ann Tighe Houlihan Lawrence Inc.

    246 Horseshoe Cir, Ossining, NY 10562
  • 16 Rockledge Ave Unit 7D1, Ossining, NY 10562
    16 Rockledge Ave Unit 7D1, Ossining, NY 10562
    16 Rockledge Ave Unit 7D1, Ossining, NY 10562
    /29

    $379,000 Pending

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

    16 Rockledge Ave Unit 7D1, Ossining, NY 10562

    Welcome to this tastefully renovated corner penthouse co-op in the coveted Scarborough Manor development. This spacious unit offers stunning, unobstructed panoramic river views from every room! The home has an abundance of large windows creating a light-filled, airy atmosphere. As you step in your are welcomed by an oversized foyer that leads to the breathtaking living room with beautiful

    Sarah Mirza Mulhall Julia B Fee Sothebys Int. Rlty

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

    $660,000 Sold Jul 29, 2025

    • 1,338 Sq Ft
    • $493/SF
    • 17 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1905

    23 Brookville Ave, Ossining, NY 10562

    Welcome to this truly special 3-bedroom, 2-bathroom Victorian home, gracefully nestled in the heart of Ossining’s desirable Chilmark neighborhood. A rare blend of timeless charm and modern updates, this residence invites you to step into a world where classic craftsmanship meets today’s comfort and style.From the moment you arrive, the home’s character captivates — a nod to its historic roots

    Heather Bouza William Raveis-New York, LLC

    23 Brookville Ave, Ossining, NY 10562
  • 78 Alder Dr, Briarcliff Manor, NY 10510
    78 Alder Dr, Briarcliff Manor, NY 10510
    78 Alder Dr, Briarcliff Manor, NY 10510
    /45

    $1,349,000 Pending

    • 4 Beds
    • 3 Baths
    • 2,413 Sq Ft

    78 Alder Dr, Briarcliff Manor, NY 10510

    Backyard Oasis in Briarcliff Manor School District! This beautifully maintained 4-bedroom, 3-bath residence offers over 2,500 sq ft of bright, versatile living space in one of the area’s most desirable neighborhoods. The main level features a spacious, open flow with sun-filled living and dining areas, a center island kitchen and seamless access to the outdoors. Four generously sized bedrooms,

    Jamey Gelardi Houlihan Lawrence Inc.

    78 Alder Dr, Briarcliff Manor, NY 10510
  • 47 Pine Ave, Ossining, NY 10562

    $600,000 Sold Jul 29, 2025

    • 1,248 Sq Ft
    • $481/SF
    • 33 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1900

    47 Pine Ave, Ossining, NY 10562

    Come view this immaculately kept gem located in Ossining Village. First time to market in 45 years, this charming 4 bedroom, 2 full bath classic Cape boasts a new kitchen and updated baths. First floor features a bedroom with full bath for primary use or potential guest suite. Second floor has three rooms and full hall bath. Third room on this level perfect for nursery or home office. Basement

    Kathy Kane Coldwell Banker Realty

    47 Pine Ave, Ossining, NY 10562
  • 102 Butternut Rd, Briarcliff Manor, NY 10510
    102 Butternut Rd, Briarcliff Manor, NY 10510
    102 Butternut Rd, Briarcliff Manor, NY 10510
    /33

    $1,349,000 Pending

    • 4 Beds
    • 3 Baths
    • 2,799 Sq Ft

    102 Butternut Rd, Briarcliff Manor, NY 10510

    Set on nearly an acre of beautifully landscaped property in a quiet cul-de-sac, this updated four-bedroom, three-and-a-half-bathroom Contemporary split-level home offers bright, open living spaces. Located in the desirable Briarcliff Manor School District, this home is perfect for both entertaining and everyday living. The main level features a spacious living room with a wood burning fireplace,

    Cindy Glynn Compass Greater NY, LLC

    102 Butternut Rd, Briarcliff Manor, NY 10510
  • 3 Ward Place, Ossining, NY 10562

    $525,000 Sold Jul 25, 2025

    • 1,474 Sq Ft
    • $356/SF
    • 41 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1933

    3 Ward Place, Ossining, NY 10562

    Charming Tudor on a tree-lined street with tons of potential. Rooms live large - huge living room with fireplace, kitchen with center island, study/den bonus room on the main level. Full sized unfinished basement where the possibilities are endless, and a full-height attic. Two-car detached garage is perfect for a workshop. Oversized deck and great yard. Don't miss the opportunity to turn this

    Tracy Salciccia ERA Insite Realty Services

    3 Ward Place, Ossining, NY 10562
  • 106 Mystic Dr, Ossining, NY 10562
    106 Mystic Dr, Ossining, NY 10562
    106 Mystic Dr, Ossining, NY 10562
    /50

    $1,099,000 Pending

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

    106 Mystic Dr, Ossining, NY 10562

    Mystic Pointe in Ossinng is a coveted gated community tucked between the Hudson and N. Highland Ave., offering a serene lifestyle with the convenience of nearby Croton-on-Hudson Metro North, local shops and scenic nature trails. This highly desirable Chatham end unit model has been meticulously maintained and features a sought-after main level primary suite with en-suite bath. The open and

    Jody Toth Corcoran Legends Realty

    106 Mystic Dr, Ossining, NY 10562
  • 94 Linden Ave, Ossining, NY 10562

    $720,000 Sold Jul 25, 2025

    • 1,944 Sq Ft
    • $370/SF
    • 68 Days On Market
    • 6 Beds
    • 2 Baths
    • Built 1900

    94 Linden Ave, Ossining, NY 10562

    Welcome to this legal 2 family Stucco Colonial 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 property offers character, charm, and details one expects from this vintage. Unit 1: The main floor: the gracious entry leads you to an enclosed

    Maria Vele Keller Williams Realty Partner

    94 Linden Ave, Ossining, NY 10562
  • 127 S Highland Ave Unit A4, Ossining, NY 10562
    127 S Highland Ave Unit A4, Ossining, NY 10562
    127 S Highland Ave Unit A4, 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
  • 73 Pine Ave, Ossining, NY 10562

    $660,000 Sold Jul 23, 2025

    • 2,464 Sq Ft
    • $268/SF
    • 14 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1984

    73 Pine Ave, Ossining, NY 10562

    In Ossining there is a rare gem, (lives like 5) legal 4-bedroom, 2.5-bath colonial offering 2,464 sq ft of living space. Featuring two levels of living. As you enter, you can head right to the first floor, which is the Den/office. Continue with the first level living to the utility room then First floor bathroom. to the left of the big living room is first floor bedroom. Off the living room is

    Howard Payson RE/MAX Town & Country

    73 Pine Ave, Ossining, NY 10562
  • 31 Magnolia Rd, Briarcliff Manor, NY 10510
    31 Magnolia Rd, Briarcliff Manor, NY 10510
    31 Magnolia Rd, Briarcliff Manor, NY 10510
    /32

    $899,000 Pending

    • 3 Beds
    • 3 Baths
    • 2,550 Sq Ft

    31 Magnolia Rd, Briarcliff Manor, NY 10510

    Accepted offer....Welcome to your dream home in this desirable Chilmark Park neighborhood. This lovely split-level home offers the perfect combination of space, comfort, and style. Situated on a half-acre of land, this property boasts three bedrooms, three baths, and many features that make it a must-see. As you step inside, you'll be greeted by entry with vaulted ceilings, a sun filled sunken

    Lena O'Neill Howard Hanna Rand Realty

    31 Magnolia Rd, Briarcliff Manor, NY 10510
  • 117 S Highland Ave Unit 5H, Ossining, NY 10562

    $300,000 Sold Jul 23, 2025

    • 1,200 Sq Ft
    • $250/SF
    • 50 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1963

    117 S Highland Ave Unit 5H, Ossining, NY 10562

    Welcome to this beautifully renovated 3-bedroom, 2-bathroom apartment in the highly desirable Parkview Cooperative complex, nestled in the heart of Ossining. This well-maintained unit offers a private balcony overlooking Nelson Park, with views of the Hudson River. Step inside to a spacious dining area, hard wood floors throughout, and ample storage with four closets. The renovated kitchen

    Dina DiPaola-Gulli Keller Williams Realty Group

    117 S Highland Ave Unit 5H, Ossining, NY 10562
  • 23 Brookwood Dr, Briarcliff Manor, NY 10510
    23 Brookwood Dr, Briarcliff Manor, NY 10510
    23 Brookwood Dr, Briarcliff Manor, NY 10510
    /46

    $1,550,000 Pending

    • 4 Beds
    • 3.5 Baths
    • 4,592 Sq Ft

    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
  • 444 River Rd, Briarcliff Manor, NY 10510

    $1,410,000 Sold Jul 22, 2025

    • 4,412 Sq Ft
    • $320/SF
    • 20 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1984

    444 River Rd, Briarcliff Manor, NY 10510

    Unmatched Hudson River Views • Endless Potential • Coveted Location - Welcome to 444 River Road—a rare opportunity to own prime riverfront property in Briarcliff Manor with panoramic Hudson River views from every room. Perfectly positioned for privacy and stunning sunsets, this 4-bedroom contemporary offers bold architectural lines, exceptional outdoor space, and the chance to own your

    Hillary Landau Compass Greater NY, LLC

    444 River Rd, Briarcliff Manor, NY 10510
  • 27 Knoll View, Ossining, NY 10562
    27 Knoll View, Ossining, NY 10562
    27 Knoll View, Ossining, NY 10562
    /25

    $450,000 Pending

    • 2 Beds
    • 1.5 Baths
    • 1,200 Sq Ft

    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
  • 117 S Highland Ave Unit 1H, Ossining, NY 10562

    $280,000 Sold Jul 22, 2025

    • 827 Sq Ft
    • $339/SF
    • 67 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1962

    117 S Highland Ave Unit 1H, Ossining, NY 10562

    Welcome to 117 South Highland Avenue!! This lovely 3-bedroom, 2-bathroom corner unit is a rare gem nestled in a beautifully maintained complex. Imagine waking up to breathtaking park views right from your private ground-level deck – the perfect spot for morning coffee or evening relaxation. Unwind and reconnect in the complex's amenities, including an inground pool and inviting recreation

    Tatiana Volcy Charles Rutenberg Realty, Inc.

    117 S Highland Ave Unit 1H, Ossining, NY 10562
  • 33 Ann St, Ossining, NY 10562
    33 Ann St, Ossining, NY 10562
    33 Ann St, Ossining, NY 10562
    /24

    $699,000 Pending

    • 5 Beds
    • 3 Baths
    • 2,000 Sq Ft

    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

    Matthew Bizzarro Bizzarro Agency, LLC

    33 Ann St, Ossining, NY 10562
  • 45 Lee Ave, Ossining, NY 10562

    $635,000 Sold Jul 21, 2025

    • 1,274 Sq Ft
    • $498/SF
    • 16 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1962

    45 Lee Ave, Ossining, NY 10562

    Step into the charm of 45 Lee Avenue, a beautiful, impeccable move in ready four-bedroom Cape Cod nestled in Ossining. Imagine cooking in the custom kitchen, with gleaming granite counters, and modern stainless-steel appliances, or relaxing on the expansive composite deck overlooking your private backyard oasis. Hardwood floors flow throughout the home, and ductless AC ensures your comfort. The

    Suzanne Lagle Houlihan Lawrence Inc.

    45 Lee Ave, Ossining, NY 10562

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