Ossining, NY Homes

• 

  

  

  /49

  $3,000,000

  • 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
• 

  

  

  /29

  $6,000 per month

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

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

  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 opens via sliding doors to a large

  

  Hillary Landau

  Compass Greater NY, LLC

  (914) 540-8354

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

  $560,000 Sold Jun 13, 2025

  • 1,298 Sq Ft
  • $431/SF
  • 41 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1975

  224 Kemeys Cove Unit 2-24, Briarcliff Manor, NY 10510

  Life's a dream in this renovated 2-bed/2.1-bath duplex condo with Hudson River views. Large, main-level open floor plan. Living area with Hudson River views from slider to balcony with retractable awning. Dining area with Juliet balcony and pass-through to updated kitchen with stainless steel appliances & granite counter tops. Refreshed powder room adjoins entry hall. Upstairs landing suitable

  Stacy Levey William Raveis-New York, LLC

  224 Kemeys Cove Unit 2-24, Briarcliff Manor, NY 10510
• 

  Est $253,000 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
• 

  

  

  /46

  $2,550,000 Pending

  • 5 Beds
  • 5.5 Baths
  • 6,080 Sq Ft

  652 Long Hill Rd W, Briarcliff Manor, NY 10510

  Tucked away on 2 private, beautifully landscaped acres in the sought-after Briarcliff Manor school district, this exceptional mid-century modern retreat offers the perfect blend of design, comfort, and functionality. The property boasts a resurfaced saltwater pool, perennial gardens, a tranquil koi pond, and a sprawling backyard with space for a potential tennis court. Step inside the

  

  Jennifer Fischman

  Houlihan Lawrence Inc.

  (914) 266-7684

  652 Long Hill Rd W, Briarcliff Manor, NY 10510
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  /50

  $3,095 - $6,750 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
• 

  $815,000 Sold Jun 09, 2025

  • 2,050 Sq Ft
  • $398/SF
  • 19 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1965

  10 Redway Rd, Ossining, NY 10562

  Charming Colonial – Nestled at the end of a quiet cul-de-sac, 10 Redway Road exudes curb appeal with its classic Colonial charm and inviting presence. This spacious 5-bedroom home offers a thoughtfully designed layout, featuring an expanded kitchen, sunlit family room with a cozy wood-burning fireplace, and seamless access to an expansive deck overlooking the large backyard—perfect for outdoor

  Maureen Verre Houlihan Lawrence Inc.

  10 Redway Rd, Ossining, NY 10562
• 

  Est $860,715 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
• 

  

  /48

  $1,300,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 4,412 Sq Ft

  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 dream

  

  Hillary Landau

  Compass Greater NY, LLC

  (914) 483-5726

  444 River Rd, Briarcliff Manor, NY 10510
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  /34

  $2,400 per month

  • 1 Bed
  • 1 Bath
  • 950 Sq Ft
  • Apartment for Rent

  12 Lincoln Place Unit 1C, Ossining, NY 10562

  Discover this cozy haven in Ossining! This fully renovated 1 bed/1bath first floor unit with private entrance. This apt is 950 sq ft of meticulouslydesigned living space on the first floor. The home includes heat, hot water, & cooking gas, w/ the tenant responsible for electric & cable. Perfectlysituated in the heart of Ossining this residence presents an updated eat-in kitchen equipped with

  Alana Ciuffetelli Julia B Fee Sothebys Int. Rlty

  12 Lincoln Place Unit 1C, Ossining, NY 10562
• 

  $245,000 Sold Jun 09, 2025

  • 950 Sq Ft
  • $258/SF
  • 25 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1962

  18 Charter Cir Unit 18, Ossining, NY 10562

  Townhouse style living in this two bedroom unit with a private entrance and two levels! High Meadow is a sought after garden style cooperative community. Immediate parking spot outdoors, garage spots are currently on a waitlist. Laundry and a complimentary storage space available. You can walk to shopping, food, and local bus stops. Only 5 minutes away from Ossining waterfront parks,

  Christine Naber RE/MAX Distinguished Hms.&Prop

  18 Charter Cir Unit 18, 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
• 

  

  /47

  $1,850,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 6,116 Sq Ft

  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 ceilings, 2

  

  Hillary Landau

  Compass Greater NY, LLC

  (914) 685-6807

  24 Hollow Tree Rd, Briarcliff Manor, NY 10510
• 

  

  /35

  $2,914 - $26,225 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
• 

  $795,000 Sold Jun 05, 2025

  • 1,701 Sq Ft
  • $467/SF
  • 14 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1955

  9 Leawood Dr, Briarcliff Manor, NY 10510

  This wonderful, pristine house on a quiet cul-de-sac is ready for you to move right in! With a three-season Sunroom and HUGE basement area to make your own NOT included in the square footage, this house truly lives like a much larger home than many in the desired neighborhood. The updated Kitchen with stainless steel, GE Profile appliances COULD be converted to be Eat-In - OR use the current

  Eric Lebenson ERA Insite Realty Services

  9 Leawood Dr, 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
• 

  

  /41

  $925,000 Pending

  • 5 Beds
  • 3.5 Baths
  • 2,684 Sq Ft

  21 Vails Ln, Ossining, NY 10562

  Discover the perfect blend of elegance and comfort in this stunning 5-bed, 3.5-bath colonial home situated on 1 acre with a pool, circular driveway, in the vibrant town of Ossining.Step inside through the formal entry into an oversized living room, bathed in abundant natural light and featuring gleaming hardwood floors. Entertain in the formal dining room, which boasts sliders leading out to an

  

  Sherry Wiggs

  Houlihan Lawrence Inc.

  (914) 829-3451

  21 Vails Ln, Ossining, NY 10562
• 

  

  /13

  $3,100 per month

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

  3 Stanley Ave, Ossining, NY 10562

  Welcome to 3 Stanley Ave - Unit B! A Tastefully updated apartment that has plenty of great features to offer. Located conveniently to both Ossining & Croton on Hudson, the river-town charm will be sure to impress time & time again! The Unit features a comfortable yet classic layout with the Living Room, Dining Room, & Kitchen on the first floor! The 2 Bedrooms & Full Bath are located on 2nd

  Dom Fedele Premier Realty Boutique, LLC

  3 Stanley Ave, Ossining, NY 10562
• 

  $3,000,000 Sold Jun 05, 2025

  • 4,002 Sq Ft
  • $750/SF
  • 41 Days On Market

  • 3 Beds
  • 4 Baths
  • Built 1957

  104 Marlborough Rd, Briarcliff Manor, NY 10510

  The Roy O. Allen House on Marlborough Road is arguably one of the most renowned modern homes in Westchester County and a celebrated icon of mid-century glass architecture worldwide. Featured prominently in Architectural Digest, Dwell, GQ, The New York Times, and TV shows like Fallout and Hunters (Amazon Prime), this 1957 International Style pavilion is a masterwork of design. (In fact, these

  Joanna Rizoulis Julia B Fee Sothebys Int. Rlty

  104 Marlborough Rd, 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
• 

  

  /31

  $1,300,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 3,613 Sq Ft

  48 Central Dr W, Briarcliff Manor, NY 10510

  Discover this charming and spacious colonial nestled in the sought-after estate area of Briarcliff Manor. Set on a picturesque 1.4-acre property, this home offers the perfect blend of usable space and natural beauty, with scenic rock outcroppings and a vegetable garden that add character to the landscape. Featuring a solid foundation and timeless architecture, this home boasts a spacious

  

  Hillary Landau

  Compass Greater NY, LLC

  (914) 353-4113

  48 Central Dr W, Briarcliff Manor, NY 10510
• 

  

  /9

  $1,839 - $2,525 per month

  Cortlandt Living

  Studio-1 Bed

  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
• 

  $300,000 Sold Jun 05, 2025

  • 1,212 Sq Ft
  • $248/SF
  • 28 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1965

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

  Welcome to 119 South Highland Ave, Apt 6H – A Bright and Spacious 3-Bedroom 2-bath Co-op in the Heart of Ossining. Located in the desirable Parkview complex, this beautifully maintained 3-bedroom, 2-bathroom offers a perfect blend of comfort, convenience, and style. Featuring generous living space, this top-floor unit is bathed in natural light thanks to its large windows and open floor plan. A

  Chintan Trivedi RE/MAX In The City

  119 S Highland Ave Unit 6H, 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
• 

  

  /10

  $4,000,000 Pending

  • Land
  • 16 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
• 

  

  /27

  $5,500 per month

  • 3 Beds
  • 1.5 Baths
  • 1,701 Sq Ft
  • House for Rent

  55 Sherwood Ave, Ossining, NY 10562

  Charming front porch colonial on tree lined Street. Front door opens to entry hall, large dining room and living room with hardwood floors, arched walkways between rooms. Beautifully updated kitchen with island and stainless appliances, half bath. A first floor bonus room that can be used as a bedroom or den/office. Upstairs leads to three bedrooms, a full bath, hardwood floors throughout,

  Robin Schwamb North Country Sothebys Int Rlt

  55 Sherwood Ave, Ossining, NY 10562
• 

  $670,000 Sold Jun 05, 2025

  • 1,744 Sq Ft
  • $384/SF
  • 30 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1999

  16 Sabrina Ln, Ossining, NY 10562

  Completely renovated 3 bedroom, 3 bath Raised Ranch in quiet neighborhood. Enjoy the renovated, spacious Eat-in kitchen with quartz counters, stainless appliances, newly painted cabinetry and sliding door to rear deck. Hardwood floor in the living room with bay window and fireplace. New flooring throughout and newly painted throughout. Each bedroom has a ceiling fan and closet. Each bathroom has

  Mark Seiden Mark Seiden Real Estate Team

  16 Sabrina Ln, 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
• 

  

  /44

  $1,330,000

  • 4 Beds
  • 2.5 Baths
  • 3,568 Sq Ft

  30 Cottonwood Ln, Briarcliff Manor, NY 10510

  Charming classic Dutch Colonial offers transitional style throughout and is perfectly situated on a private 1.15-acre lot in a sought-after cul-de-sac. Formal living spaces include an expansive living room, a formal dining room and a family room with a wood burning fireplace, ideal for every day living or entertaining. A first-floor bonus room, once used to house an expansive train collection,

  

  Maria Teresa Duguet

  Houlihan Lawrence Inc.

  (914) 567-4698

  30 Cottonwood Ln, Briarcliff Manor, NY 10510
• 

  

  /15

  $1,947 - $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
• 

  $610,000 Sold Jun 04, 2025

  • 1,200 Sq Ft
  • $508/SF
  • 16 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1996

  203 Glenwood Dr, Briarcliff Manor, NY 10510

  Scarborough Glen is a lovely community featuring condominium and townhouse style homes with beautifully landscaped grounds complete with wooded nature preserve. Amenities include in ground pool, playground, fitness center and beautiful community room. Close to shops, restaurants, Sleepy Hollow Country Club, Scarborough or Ossining train station, Croton Aqueduct trailway, Rockefeller State

  Deborah Valentino Houlihan Lawrence Inc.

  203 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
• 

  

  /23

  $210,000

  • 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
• 

  

  /10

  $2,200 per month

  • 1 Bed
  • 1 Bath
  • 950 Sq Ft
  • Apartment for Rent

  10 Forest Ave, Ossining, NY 10562

  Welcome to 10 Forest Avenue with walkup to 2nd floor rental unit. This unit & entire home had been completed renovated & offers a 1 bedroom, bathroom with standup shower, livingroom, storage, and kitchen with electric stove, refrigerator & island. Ductless units, lots of natural light, street parking with permit. No smoking or pets allowed & no use of backyward.

  Elizabeth Kamp Kane & Associates

  10 Forest Ave, Ossining, NY 10562
• 

  $806,990 Sold Jun 04, 2025

  • 2,444 Sq Ft
  • $330/SF
  • 19 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1920

  63 Sunset Dr, Ossining, NY 10562

  Welcome Home to timeless charm and modern comfort. Like a warm embrace, this enchanting 1920s red brick Colonial invites you in with classic elegance and thoughtful updates throughout. Tucked in a picturesque and sought-after residential neighborhood just minutes from vibrant shops, dining, and Metro-North train, this home offers the perfect blend of old-world craftsmanship and today’s

  Nancy Beard Houlihan Lawrence Inc.

  63 Sunset Dr, Ossining, NY 10562
• 

  /2

  Est $150,000 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 750 Sq Ft

  98 Charter Cir Unit C, Ossining, NY 10562

  98 Charter Cir Unit C, Ossining, NY 10562
• 

  

  /27

  $210,000

  • 2 Beds
  • 1 Bath
  • 672 Sq Ft

  135 S Highland Ave 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) 409-9352

  135 S Highland Ave Unit D1, 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
• 

  $875,000 Sold Jun 04, 2025

  • 2,614 Sq Ft
  • $335/SF
  • 26 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1862

  12 Maurice Ave, Ossining, NY 10562

  Welcome to 12 Maurice Avenue, a beautifully renovated legal 2-family home situated in the charming Village of Ossining! This versatile property offers a unique opportunity for both investors and owner-occupants. The ground-level unit features 3 bedrooms, 1 full bath, spacious open kitchen with new quartz countertops, separate dining area, cozy family room, and access to a large backyard patio

  Michael Clemente DeSimone Real Estate

  12 Maurice Ave, 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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