Westchester, NY Homes

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  /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

• 

  

  

  /17

  $2,800 per month

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

  149 Central Dr, Briarcliff Manor, NY 10510

  Step into a unique blend of old-world charm and modern comfort in this beautifully renovated 1-bedroom apartment, located on the first floor of a distinctive 6-unit colonial home in the heart of Briarcliff Manor.This spacious residence features super high ceilings, refinished floors, and an abundance of natural light throughout. The inviting living room boasts an original exposed brick

  

  Valerio Santucci

  Link NY Realty

  (914) 873-5783

  149 Central Dr, Briarcliff Manor, NY 10510
• 

  $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
• 

  Est $156,000 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
• 

  

  

  /35

  $1,850,000

  • 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
• 

  

  /27

  $5,100 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
• 

  $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
• 

  Est $858,348 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
• 

  

  /44

  $1,330,000 Pending

  • 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
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  /50

  $2,768 - $27,520 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
• 

  $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
• 

  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
• 

  

  /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
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  /46

  $5,500 per month

  • 2 Beds
  • 4 Baths
  • 2,100 Sq Ft
  • Condo for Rent

  3 Deer Tree Ln, Briarcliff Manor, NY 10510

  Welcome to this spacious townhouse in sought-after Wyndcrest in the village of Briarcliff Manor with award winning Briarcliff Schools!This beautifully maintained two-bedroom, two full and two half bathroom home offers four fully finished levels with plenty of storage space and nearly all new appliances. The main level features an inviting eat-in kitchen with granite countertops, ceramic

  Linda Einfrank Sterling Property Solutions

  3 Deer Tree Ln, Briarcliff Manor, NY 10510
• 

  $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
• 

  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
• 

  

  /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
• 

  $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
• 

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft

  14 Charter Cir, Ossining, NY 10562

  14 Charter Cir, 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
• 

  

  /10

  $1,750 per month

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

  46 Ferris Place, Ossining, NY 10562

  Come see this 1 Bedroom, 1 Bath apartment on the 2nd floor of a private home. Hardwood floors throughout. Close to all - public transportation, schools, shopping and Metro North.

  Jason Kerwar William Raveis-New York, LLC

  46 Ferris Place, Ossining, NY 10562
• 

  $960,000 Sold Jul 23, 2025

  • 2,872 Sq Ft
  • $334/SF
  • 47 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 1948

  193 Chappaqua Rd, Briarcliff Manor, NY 10510

  Nestled along a scenic road in Briarcliff Manor, this idyllic two-family home sits on more than an acre and a half of beautifully landscaped grounds, offering two distinct and exquisitely appointed residences. From the moment you arrive, it's clear that this is a truly special and unique property.The estate is thoughtfully divided by two private driveways, each bordered by classic stone walls

  Marc Campolongo Marc Jason

  193 Chappaqua Rd, Briarcliff Manor, NY 10510
• 

  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
• 

  

  /37

  $2,900 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
• 

  $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
• 

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft

  43 Charter Cir, Ossining, NY 10562

  43 Charter Cir, Ossining, NY 10562
• 

  

  /16

  $150,000

  • 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
• 

  

  /15

  $5,000 per month

  • 3 Beds
  • 2 Baths
  • 2,100 Sq Ft
  • House for Rent

  2 Blue Lantern Rd, Briarcliff Manor, NY 10510

  Sprawling 3 bedroom 2 bath high ranch with large family room ,spacious yard ,2 car garage , skylights, just a few steps to the park, restaurants & more.

  Lisa Omboni Main Source Realty, Ltd.

  2 Blue Lantern Rd, Briarcliff Manor, NY 10510
• 

  $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
• 

  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

  $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
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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
• 

  $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
• 

  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
• 

  

  /27

  $210,000

  • 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) 601-2993

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

  

  /18

  $3,500 per month

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Apartment for Rent

  231 Eastern Ave Unit 2, Ossining, NY 10562

  Discover this beautifully updated 3-bedroom, 1-bathroom apartment located in the charming village of Ossining. Positioned on the second floor of a private, three-family home, this residence offers both comfort and convenience.Step inside to find a huge living room and dining room, perfect for entertaining or relaxing. The brand-new kitchen is a chef's delight, featuring modern white shaker

  Valerie Cascione Compass Greater NY, LLC

  231 Eastern Ave Unit 2, 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
• 

  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

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