Ossining, NY Homes

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  /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
• 

  

  

  /55

  $3,595 - $5,895 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
• 

  $101,500 Sold Apr 30, 2025

  • 6,500 Sq Ft
  • $16/SF
  • 27 Days On Market

  • 8 Beds
  • 6.5 Baths
  • Built 1906

  1340 Kitchawan Rd, Ossining, NY 10562

  Auction 1/26-1/28 - This picturesque home in Ossining is situated on Shadow Lake (man-made) and needs someone who can transform it and bring it back to life. You enter through high wrought iron gates that brings you to a 6500 sq ft home boasting 4.2 acres of property that is picturesque, quiet and serene. The wood carvings throughout the home take you back in time. There is a lot of history that

  Donna Ramundo Keller Williams Valley Realty

  1340 Kitchawan Rd, Ossining, NY 10562
• 

  Est $267,000 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
• 

  

  

  /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
• 

  

  /23

  $3,100 per month

  • 2 Beds
  • 1.5 Baths
  • 800 Sq Ft
  • Apartment for Rent

  57 Stafford St Unit 53, Briarcliff Manor, NY 10510

  Newly renovated, 2 bedrooms, 1.5 baths. Brand new kitchen cabinets, appliances and quartz counter top. This entire unit has been newly renovated from top to bottom. Both bedrooms, walk-in closet and 1 full bath on 2nd floor; Living room, kitchen and bath on first floor; Washer and dryer are in the open climate controlled basement. New central AC and heat pump. This beautiful side-by-side 2 family

  Peter Nikic Broad & Bailey Realty LLC

  57 Stafford St Unit 53, Briarcliff Manor, NY 10510
• 

  $875,000 Sold Apr 28, 2025

  • 3,000 Sq Ft
  • $292/SF
  • 9 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2020

  8 Thornton Hill, Ossining, NY 10562

  Discover your dream home in this meticulously crafted 2020 Colonial featuring the sought-after Hawk model in Hawkes Crossing. Nestled in a charming cul-de-sac, this exceptional property offers the perfect blend of modern comfort and classic elegance. Boasting four spacious bedrooms and two and a half bathrooms, the home provides ample living space for family and guests.The interior showcases

  Lisa Douglas Howard Hanna Rand Realty

  8 Thornton Hill, Ossining, NY 10562
• 

  Est $870,033 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
• 

  

  /29

  $1,323,000

  • 4 Beds
  • 3 Baths
  • 2,950 Sq Ft

  320 Illington Rd, Ossining, NY 10562

  Kitchawan Farmhouse built approx. 1850 featuring all up-to-date amenities. Stylish Kitchen w/cherry wood cabinetry, granite counters, Wolf gas stove, Subzero Refrig. & additional 2 refrigerator draws in cabinets.. Enter the Formal Dining Room and extra large Living Room with wood burning original fireplace and freshly stained & polished wide plank floors. Continue on to the Family Room,

  Janet Auer Coldwell Banker Realty

  320 Illington Rd, Ossining, NY 10562
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  /50

  $2,728 - $17,189 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
• 

  $701,000 Sold Apr 25, 2025

  • 1,396 Sq Ft
  • $502/SF
  • 32 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1960

  16 Charles Place, Ossining, NY 10562

  You will be amazed at this house. Everything on the main level is brand new. Open-concept living provides ease in entertaining. A spacious living room with cathedral ceiling, LED recessed lighting and a ceiling fan is open to the fabulous kitchen. The kitchen features granite counters, glass backsplash, an abundance of white, soft-close cabinets and new appliances. There is a door to the

  Lucille Ettere Houlihan Lawrence Inc.

  16 Charles Place, 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
• 

  

  /41

  $1,350,000

  • 4 Beds
  • 2.5 Baths
  • 3,200 Sq Ft

  1121 Estates Dr, Ossining, NY 10562

  Discover your dream home at 1121 Estates Drive in Ossining, NY! Nestled on a picturesque 1.8-acre lot, this amazingly renovated gem offers the perfect blend of modern amenities and serene suburban living within the highly sought-after Yorktown School District.Step inside and be captivated by the gleaming, newly refinished hardwood floors and the light-filled, oversized rooms, perfect for

  Annette Cicinelli Keller Williams Realty Partner

  1121 Estates Dr, Ossining, NY 10562
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  /33

  $7,500 per month

  • 4 Beds
  • 2.5 Baths
  • 3,170 Sq Ft
  • House for Rent

  10 Applegate Way, Ossining, NY 10562

  Make yourself at home at 10 Applegate Way in the desirable Waterview Estates. This impeccably maintained colonial home is located on a cul-de-sac and set on 1.7 partially wooded acres bordering reserve land, ensuring quiet and privacy. The level front and back yards and the spacious deck provide endless options for outdoor fun and relaxation. The house boasts ample living space and 4 comfortable

  Julia Nelson Christie's Int. Real Estate

  10 Applegate Way, Ossining, NY 10562
• 

  $362,500 Sold Apr 25, 2025

  • 1,064 Sq Ft
  • $341/SF
  • 148 Days On Market

  • 1 Bed
  • 2 Baths
  • Built 1920

  24 Campwoods Grounds, Ossining, NY 10562

  Welcome to 24 Campwoods Grounds, a fully gut-renovated 1-bedroom, 2-bath home offering a unique blend of condo-style living with the benefits of a single-family residence. This charming property is situated in the historic Campwoods Grounds community, known for its peaceful, tree-lined streets and close-knit neighborhood. Inside, you'll find a modern open-concept living area, a stylish kitchen

  Richard Blanchet Compass Greater NY, LLC

  24 Campwoods Grounds, 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
• 

  

  /43

  $1,100,000

  • 4 Beds
  • 4 Baths
  • 2,700 Sq Ft

  196 Pinesbridge Rd, Ossining, NY 10562

  **FREE EGGS!** Seize the opportunity to own this incredible farmhouse, perfectly designed for those who dream of expansive property, vibrant gardens, lush fresh berries, and the delight of raising chickens right in your backyard. This enchanting antique farmhouse, originally built in 1868, has undergone a meticulous renovation that seamlessly integrates modern conveniences while preserving the

  Cindy Kief Corcoran Legends Realty

  196 Pinesbridge Rd, Ossining, NY 10562
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  /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
• 

  $430,000 Sold Apr 23, 2025

  • 1,153 Sq Ft
  • $373/SF
  • 47 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1988

  7 Hudson Point Ln, Ossining, NY 10562

  Enjoy breathtaking views of the Hudson River from this beautifully renovated home in the highly desirable Hudson Point community. This move-in-ready residence has been thoughtfully updated with high-end finishes and modern touches throughout, making it the perfect place to call home. The stunning new kitchen features sleek granite countertops and a convenient breakfast bar, ideal for both casual

  Suzan Zeolla Houlihan Lawrence Inc.

  7 Hudson Point Ln, Ossining, NY 10562
• 

  Est $549,000 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,580 Sq Ft

  16 Rockledge Ave Unit 4B1, Ossining, NY 10562

  16 Rockledge Ave Unit 4B1, Ossining, NY 10562
• 

  

  /45

  $1,094,000

  • 5 Beds
  • 4 Baths
  • 2,456 Sq Ft

  140 Fuller Rd, Briarcliff Manor, NY 10510

  Charming & Surprisingly Spacious Cape in Briarcliff ManorDon’t let its unassuming exterior fool you—this 5-bedroom, 4-bath Cape-style home in the heart of Briarcliff Manor’s desirable Neighborhood Park neighborhood is full of unexpected space, comfort, and charm. Located within the sought-after Briarcliff School District and enjoying full access to Briarcliff recreation, this home offers the

  Wendy Phillips Corcoran Legends Realty

  140 Fuller Rd, Briarcliff Manor, NY 10510
• 

  

  /13

  $4,500 per month

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

  1123 Pleasantville Rd Unit 3A, Briarcliff Manor, NY 10510

  Luxury rental living in downtown Briarcliff Manor! This brand new construction elevator building is now offering studio, 1 bedroom and 2 bedroom units. A unique boutique-style rental opportunity, with only 8 units available. Unit 3A is a two bedroom apartment featuring an open layout. This corner unit is bright and sunny thanks to the large windows bringing in natural light. As you step

  Cord Stahl Compass Greater NY, LLC

  1123 Pleasantville Rd Unit 3A, Briarcliff Manor, NY 10510
• 

  $355,000 Sold Apr 22, 2025

  • 1,580 Sq Ft
  • $225/SF
  • 207 Days On Market

  • 2 Beds
  • 2 Baths

  16 Rockledge Ave Unit 2C2, Ossining, NY 10562

  Spacious, Sunny, & Bright unit with majestic Hudson River views from the living room, dining room/balcony and primary suite in sought after "Scarborough Manor" (a prestigious gated community) conveniently just minutes away from Metro North or a short walk to town, shops, trendy restaurants, and waterfront parks. Primary has a large dressing room/walk-in closet and bath making it a lovely ensuite

  Christopher Cawley Corcoran Legends Realty

  16 Rockledge Ave Unit 2C2, 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
• 

  

  /33

  $899,222

  • 4 Beds
  • 2.5 Baths
  • 3,551 Sq Ft

  1 Noel Dr, Ossining, NY 10562

  Sprawling Cape Cod style home with first floor primary suite on a fabulous, private setting. Kitchen has stainless appliances and stone counters, formal dining room has large bay window looking out at the fenced-in property, and living room has high ceilings and a fireplace. Sun Room off the kitchen has 3 skylights and the covered patio off the kitchen overlooks the lush landscaping, backing up

  Mark Seiden Mark Seiden Real Estate Team

  1 Noel Dr, Ossining, NY 10562
• 

  

  /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
• 

  $420,000 Sold Apr 21, 2025

  • 2,087 Sq Ft
  • $201/SF
  • 54 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1897

  23 Ann St, Ossining, NY 10562

  First Sale in over 30 Years. Outstanding 2 Family house sold at Discount CASH ONLY - PROOF OF FUNDS House has great bones and excellent new mechanicals but needs kitchens, baths & full cosmetics. As redone, it should be over $600K Value. Additional Information: HeatingFuel:Oil Above Ground,

  Eric Schatz Schatz Realty Group

  23 Ann St, 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
• 

  

  /33

  $825,000

  • 3 Beds
  • 2 Baths
  • 1,767 Sq Ft

  43 Ganung Dr, Ossining, NY 10562

  Welcome to 43 Ganung Drive, a beautifully updated home nestled in the heart of Ossining—just a 10-minute drive to the Metro-North station for a quick and easy commute to Grand Central. Located near the scenic Hudson River, this home perfectly blends charm and modern style.Step into the heart of the home—a renovated open-plan kitchen thoughtfully designed for the home chef. Outfitted with modern

  Deirdre Coffey Compass Greater NY, LLC

  43 Ganung Dr, Ossining, NY 10562
• 

  

  /23

  $3,600 per month

  • 2 Beds
  • 1.5 Baths
  • 1,318 Sq Ft
  • House for Rent

  227 Cedar Ln, Ossining, NY 10562

  Croton very unique charm. 220 year old original log cabin. Pond, brook, magnificent wildlife. 6.4 acres. Less than 1 hr to Manhattan. 5 minutes to Croton train station and supermarket, shops, restaurants. 1-2 bedrooms, 1.5 baths. Precious privacy. Swim, boat, kayak nearby. Yearly rental only.

  Brenda Timm Coldwell Banker Realty

  227 Cedar Ln, Ossining, NY 10562
• 

  $527,000 Sold Apr 16, 2025

  • 1,141 Sq Ft
  • $462/SF
  • 13 Days On Market

  • 1 Bed
  • 1.5 Baths
  • Built 1986

  274 Horseshoe Cir, Ossining, NY 10562

  Beautiful one bedroom condo in the highly coveted Fox Hill community! This well cared for home has an open floor plan that includes a mudroom, spacious living room with WB fireplace, dining room with wet bar and sliders to the back deck, kitchen with breakfast bar and stainless-steel appliances. The laundry room is conveniently located on the first floor and allows for direct access to the 1 car

  Maura Mcspedon William Raveis Real Estate

  274 Horseshoe Cir, Ossining, NY 10562
• 

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft

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

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

  

  /25

  $795,000

  • 4 Beds
  • 2.5 Baths
  • 1,886 Sq Ft

  3 Willow Dr, Briarcliff Manor, NY 10510

  Welcome to this beautifully maintained Colonial, ideally situated less than a mile from the heart of Briarcliff Manor. Thoughtfully updated and tastefully appointed, this home features exquisite custom woodwork, built-in cabinetry and high-end finishes throughout.The bright, eat-in kitchen opens through elegant French doors to a stunning stone patio and a level backyard surrounded by mature

  Susan Slotnick William Raveis Real Estate

  3 Willow Dr, Briarcliff Manor, NY 10510
• 

  

  /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
• 

  $668,000 Sold Apr 16, 2025

  • 1,408 Sq Ft
  • $474/SF
  • 27 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1953

  89 Morningside Dr, Ossining, NY 10562

  Welcome home to your Ossining Oasis! This charming split-level ranch offers a comfortable and convenient lifestyle with 3 large bedrooms and 2 full baths. This home features a spacious living room with a wood-burning fireplace, a bright kitchen with stainless steel appliances, and a dining room that opens to a delightful deck and stone patio overlooking a large, private, and level backyard.

  Jean-Charles DeOliveira Scappaticci ERA Insite Realty Services

  89 Morningside 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
• 

  

  /23

  $575,000

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

  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
• 

  

  /5

  $3,200 per month

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Apartment for Rent

  57 S Highland Ave, Ossining, NY 10562

  Welcome to your newly renovated 3-bedroom, 1-bathroom apartment, in second floor, ready to move in. This spacious and charming home features all new stainless steel appliances, and a bright eat-kitchen perfect for daily living and entertaining. Walk-to town, shops, and restaurants.

  Sabina Rodriguez eXp Realty

  57 S Highland Ave, Ossining, NY 10562
• 

  $312,200 Sold Apr 16, 2025

  • 986 Sq Ft
  • $317/SF
  • 140 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1989

  27 Knoll View, Ossining, NY 10562

  Amazing opportunity awaits you. This home includes two bedrooms with approximately 986 square feet. Records show it was built around 1989. Roll up your sleeves and put your designer touches to make it a dream home. At this price if you blink it will be SOLD. Buyers check with City, County, Zoning, Tax, and other records to their satisfaction. AS-IS SALE property. Buyers to inspect prior to

  Neven Spralja REALHome Services & Solutions

  27 Knoll View, Ossining, NY 10562
• 

  /2

  Est $145,000 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

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