5,366

Lewisboro, NY Homes

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  • 20 Oscaleta Rd, South Salem, NY 10590
    20 Oscaleta Rd, South Salem, NY 10590
    20 Oscaleta Rd, South Salem, NY 10590
    /36

    $1,995,000

    Pending
    • 5 Beds
    • 4.5 Baths
    • 4,886 Sq Ft

    20 Oscaleta Rd, South Salem, NY 10590

    Nestled on over 7 quiet acres along a picturesque country road, this stylish, renovated 5-bedroom, 4.1 bath home offers the best of country living — complete with a heated pool and tennis court. Set on fabulous open land just an hour from NYC, the residence was taken to the studs in 2016 and thoughtfully rebuilt for today’s lifestyle.The open-concept Great Room is the heart of the home,

    Angela Kessel Houlihan Lawrence Inc.

    20 Oscaleta Rd, South Salem, NY 10590
  • 15 Glen Dr, South Salem, NY 10590

    $710,000

    Sold Oct 07, 2025

    15 Glen Dr, South Salem, NY 10590

    • 3 Beds
    • 1.5 Baths
    • 1,924 Sq Ft
    • Built 1964

    Last Sold Summary

    • 2% Above List Price
    • $369/SF
    • 31 Days On Market

    Current Estimated Value $732,218

    Last Listing Agent AnnMarie Sementilli Julia B Fee Sothebys Int. Rlty

    15 Glen Dr, South Salem, NY 10590
  • 32 Split Rock Rd, Pound Ridge, NY 10576
    32 Split Rock Rd, Pound Ridge, NY 10576
    32 Split Rock Rd, Pound Ridge, NY 10576
    /35

    $1,695,000

    • 5 Beds
    • 3.5 Baths
    • 4,192 Sq Ft

    32 Split Rock Rd, Pound Ridge, NY 10576

    This home truly stands apart. A turnkey five-bedroom Colonial set on nearly three private acres, privately located at the end of a quiet cul-de-sac. Thoughtfully expanded from its original design, the home features an exceptional layout with remarkable versatility, perfect for entertaining, working from home, play areas, all designed to meet your lifestyle. At the heart of the home is a

    Melissa Frank Lutz Douglas Elliman Real Estate

    32 Split Rock Rd, Pound Ridge, NY 10576
  • 241 N Salem Rd, Waccabuc, NY 10597

    $2,700,000

    Sold Jun 05, 2026

    241 N Salem Rd, Waccabuc, NY 10597

    • 5 Beds
    • 5.5 Baths
    • 6,622 Sq Ft
    • Built 1999

    Last Sold Summary

    • 20% Above List Price
    • $408/SF
    • 13 Days On Market

    Current Estimated Value $2,240,282

    Last Listing Agent Lindsay Matthews Houlihan Lawrence Inc.

    241 N Salem Rd, Waccabuc, NY 10597
  • 1 Canaan Cir, South Salem, NY 10590
    1 Canaan Cir, South Salem, NY 10590
    1 Canaan Cir, South Salem, NY 10590
    /23

    $1,389,750

    Pending
    • 4 Beds
    • 4.5 Baths
    • 4,076 Sq Ft

    1 Canaan Cir, South Salem, NY 10590

    Experience the pinnacle of Westchester living in this stunning 4-bedroom, 5-bathroom colonial, perfectly situated on a premier corner lot in one of South Salem’s most coveted neighborhoods. TRULY LIVES LIKE A 5 BEDROOM!!! Minutes from top tier shopping, dining, and libraries in wonderful Wilton and New Canaan, CT! This home offers a rare blend of sophisticated design and everyday comfort. From

    James LaTempa Compass Greater NY, LLC

    1 Canaan Cir, South Salem, NY 10590
  • 25 Twin Lakes Rd, South Salem, NY 10590

    $675,000

    Sold Oct 15, 2025

    25 Twin Lakes Rd, South Salem, NY 10590

    • 4 Beds
    • 3 Baths
    • 1,944 Sq Ft
    • Built 1964

    Last Sold Summary

    • 3% Below List Price
    • $347/SF
    • 49 Days On Market

    Current Estimated Value $761,633

    Last Listing Agent Mark Boyland Keller Williams Realty Partner

    25 Twin Lakes Rd, South Salem, NY 10590
  • 32 Boulder Ln, Goldens Bridge, NY 10526
    32 Boulder Ln, Goldens Bridge, NY 10526
    32 Boulder Ln, Goldens Bridge, NY 10526
    /37

    $669,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 1,706 Sq Ft

    32 Boulder Ln, Goldens Bridge, NY 10526

    Beautifully maintained 3 bedrooms, 2.5 bath home in desirable Goldens Bridge, ideally positioned as a corner unit with a private, serene, wooded setting. The open-concept main level is enhanced by high ceilings, creating a bright and airy atmosphere through-out the living room and dining area. Sliding glass doors lead to an expansive deck, offering perfect setting for indoor-outdoor living and

    Melissa DeFeo Howard Hanna Rand Realty

    32 Boulder Ln, Goldens Bridge, NY 10526
  • 9 Ashwood Rd, South Salem, NY 10590

    $1,254,000

    Sold Dec 08, 2025

    9 Ashwood Rd, South Salem, NY 10590

    • 4 Beds
    • 3.5 Baths
    • 3,688 Sq Ft
    • Built 1997

    Last Sold Summary

    • 3% Below List Price
    • $340/SF
    • 27 Days On Market

    Current Estimated Value $1,280,181

    Last Listing Agent Lindsay Lafreniere William Raveis-New York LLC

    9 Ashwood Rd, South Salem, NY 10590
  • 101 Post Office Rd, Waccabuc, NY 10597
    101 Post Office Rd, Waccabuc, NY 10597
    101 Post Office Rd, Waccabuc, NY 10597
    /34

    $1,849,000

    Pending
    • 4 Beds
    • 4 Baths
    • 4,573 Sq Ft

    101 Post Office Rd, Waccabuc, NY 10597

    Tucked away on Waccabuc’s scenic Post Office Road, this lovingly maintained and stylishly updated 4BR was designed to capture sunlight and celebrate the views of its lushly landscaped and fenced two-acre property. Built in 1985, this is the first time it has been offered for sale. Beyond the automatic gates, a circular drive provides easy guest parking and leads to the sheltered front entrance.

    Susan Stillman Houlihan Lawrence Inc.

    101 Post Office Rd, Waccabuc, NY 10597
  • 24 Benedict Rd, South Salem, NY 10590

    $711,000

    Sold Jul 21, 2025

    24 Benedict Rd, South Salem, NY 10590

    • 4 Beds
    • 2 Baths
    • 1,846 Sq Ft
    • Built 1955

    Last Sold Summary

    • 5% Below List Price
    • $385/SF
    • 89 Days On Market

    Current Estimated Value $764,817

    Last Listing Agent Cecilia Heller Houlihan Lawrence Inc.

    24 Benedict Rd, South Salem, NY 10590
  • 31 Spring St S, South Salem, NY 10590
    31 Spring St S, South Salem, NY 10590
    31 Spring St S, South Salem, NY 10590
    /41

    $799,999

    • 4 Beds
    • 2 Baths
    • 1,900 Sq Ft

    31 Spring St S, South Salem, NY 10590

    Welcome to 31 Spring Street South in beautiful South Salem, NY — a lovingly maintained expanded ranch being offered for the first time in decades. Nestled on a private, sun-drenched property with mature landscaping and estate-like grounds, this special residence offers the perfect blend of tranquility, space, and opportunity. Featuring 4 bedrooms/2 full bathrooms, this picturesque property also

    Kathryn Norman Market Match Real Estate Corp

    31 Spring St S, South Salem, NY 10590
  • 256 Smith Ridge Rd, South Salem, NY 10590

    $725,000

    Sold Apr 20, 2026

    256 Smith Ridge Rd, South Salem, NY 10590

    • 4 Beds
    • 3 Baths
    • 2,682 Sq Ft
    • Built 1983

    Last Sold Summary

    • 9% Below List Price
    • $270/SF
    • 10 Days On Market

    Current Estimated Value $801,718

    Last Listing Agent Erin Lee Keller Williams Realty Group

    256 Smith Ridge Rd, South Salem, NY 10590
  • 274 Maplewood Dr Unit 32274, South Salem, NY 10590
    274 Maplewood Dr Unit 32274, South Salem, NY 10590
    274 Maplewood Dr Unit 32274, South Salem, NY 10590
    /27

    $399,000

    $14K PRICE INCREASE Pending
    • 1 Bed
    • 1 Bath
    • 970 Sq Ft

    274 Maplewood Dr Unit 32274, South Salem, NY 10590

    Experience carefree living at its best in this stunning, move-in-ready 1-bedroom condo. This home is bathed in natural sunlight, highlighting an effortless open-concept layout perfect for modern living. The chic kitchen features high end appliances with gleaming quartz countertops that opens directly into a bright living area anchored by a cozy fireplace. Charming barn sliding doors add a touch

    Elizabeth Koski Coldwell Banker Realty

    274 Maplewood Dr Unit 32274, South Salem, NY 10590
  • 144 Stone Meadow, South Salem, NY 10590

    $419,500

    Sold Nov 04, 2025

    144 Stone Meadow, South Salem, NY 10590

    • 1 Bed
    • 1 Bath
    • 1,112 Sq Ft
    • Built 1982

    Last Sold Summary

    • 7% Below List Price
    • $377/SF
    • 22 Days On Market

    Current Estimated Value $416,925

    Last Listing Agent Lindsay Lafreniere William Raveis-New York LLC

    144 Stone Meadow, South Salem, NY 10590
  • 158 Mead St, Waccabuc, NY 10597
    158 Mead St, Waccabuc, NY 10597
    158 Mead St, Waccabuc, NY 10597
    /32

    $1,695,000

    Open Sat 2PM - 4PM $34K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 4,259 Sq Ft

    158 Mead St, Waccabuc, NY 10597

    Welcome to 158 Mead Street — offered for the first time, this custom-designed sanctuary is nestled in the heart of Waccabuc and lives like four bedrooms (4 bedroom septic). Privately sited on over four park-like acres, this elegant residence is surrounded by mature trees, creating a serene retreat just minutes from town, train, and everyday conveniences. Inside, the home seamlessly blends rustic

    Amy Smith Sroka Julia B Fee Sothebys Int. Rlty

    158 Mead St, Waccabuc, NY 10597
  • 30 Schoolhouse Rd, Waccabuc, NY 10597

    $1,681,000

    Sold Jul 30, 2025

    30 Schoolhouse Rd, Waccabuc, NY 10597

    • 3 Beds
    • 3 Baths
    • 2,577 Sq Ft
    • Built 1950

    Last Sold Summary

    • 5% Above List Price
    • $652/SF
    • 12 Days On Market

    Current Estimated Value $1,655,391

    Last Listing Agent George D'Ambrosio Ginnel Real Estate

    30 Schoolhouse Rd, Waccabuc, NY 10597
  • 21 Elmwood Rd, South Salem, NY 10590
    21 Elmwood Rd, South Salem, NY 10590
    21 Elmwood Rd, South Salem, NY 10590
    /34

    $725,000

    Open Fri 12:30PM - 1:30PM
    • 3 Beds
    • 1 Bath
    • 1,188 Sq Ft

    21 Elmwood Rd, South Salem, NY 10590

    Rarely does an opportunity like this come along. Tucked away on nearly 5 private acres, this classic Mid-Century ranch offers the chance to create exactly the lifestyle you've been imagining. Whether you're looking for a manageable country retreat, a renovation project with room to grow, or the ideal setting for a custom estate home, this property delivers the foundation and flexibility to make

    Debi Orr Keller Williams Prestige Prop

    21 Elmwood Rd, South Salem, NY 10590
  • 72 Lambert Ridge, Cross River, NY 10518

    $1,525,000

    Sold Jul 16, 2025

    72 Lambert Ridge, Cross River, NY 10518

    • 4 Beds
    • 3.5 Baths
    • 4,335 Sq Ft
    • Built 1997

    Last Sold Summary

    • 7% Above List Price
    • $352/SF
    • 9 Days On Market

    Current Estimated Value $1,555,482

    Last Listing Agent Wendy Loring William Raveis-New York LLC

    72 Lambert Ridge, Cross River, NY 10518
    • 25 West Rd, South Salem, NY 10590

      Est $1,116,199

      Not Listed For Sale

      25 West Rd, South Salem, NY 10590

      • 4 Beds
      • 2.5 Baths
      • 3,231 Sq Ft
      • Built 1983
      25 West Rd, South Salem, NY 10590

      Last Sold Summary

      • 11 Days On Market

  • 122 E Ridge Rd, Waccabuc, NY 10597
    122 E Ridge Rd, Waccabuc, NY 10597
    /2

    $2,795,000

    Pending
    • 4 Beds
    • 5.5 Baths
    • 3,958 Sq Ft

    122 E Ridge Rd, Waccabuc, NY 10597

    THE ULTIMATE WACCABUC ESTATE. Rare Hollywood History Meets Modern Luxury. Nestled in the foremost, highly coveted Waccabuc estate area, a legendary private sanctuary. Steeped in Hollywood lore, this distinctive 1948 Country Colonial famously hosted the wedding reception for Arthur Miller and Marilyn Monroe. High-end Modern Renovation with nearly 4000 square feet of finely finished and

    Benjamin Ginnel Ginnel Real Estate

    122 E Ridge Rd, Waccabuc, NY 10597
  • 2 Hastings Ct, South Salem, NY 10590

    $960,000

    Sold Jun 26, 2025

    2 Hastings Ct, South Salem, NY 10590

    • 4 Beds
    • 2.5 Baths
    • 2,513 Sq Ft
    • Built 1970

    Last Sold Summary

    • 13% Above List Price
    • $382/SF
    • 16 Days On Market

    Current Estimated Value $971,190

    Last Listing Agent Margo Lancia Houlihan Lawrence Inc.

    2 Hastings Ct, South Salem, NY 10590
  • 15 Debbie Ln, Cross River, NY 10518
    15 Debbie Ln, Cross River, NY 10518
    15 Debbie Ln, Cross River, NY 10518
    /26

    $1,189,000

    Pending
    • 4 Beds
    • 2 Baths
    • 2,072 Sq Ft

    15 Debbie Ln, Cross River, NY 10518

    SUMMER BY THE POOL. Picture perfect Cape! Enjoy your own private backyard oasis at this beautifully renovated 4BR/2BA home. Tucked away at the end of a quiet cul-de-sac on over one level acre with a 20’x40’ in-ground salt-water pool, this property offers the perfect blend of comfort, chic style, and outdoor enjoyment. Located in the award-winning Katonah-Lewisboro school district! Renovated in

    Joanne Monteleone Ginnel Real Estate

    15 Debbie Ln, Cross River, NY 10518
  • 7 Laurie Ln, South Salem, NY 10590

    $869,000

    Sold Aug 01, 2025

    7 Laurie Ln, South Salem, NY 10590

    • 3 Beds
    • 3.5 Baths
    • 2,576 Sq Ft
    • Built 1972

    Last Sold Summary

    • $337/SF
    • 26 Days On Market

    Current Estimated Value $923,879

    Last Listing Agent Patricia Hinkley Coldwell Banker Realty

    7 Laurie Ln, South Salem, NY 10590
  • 39 Park Rd, Goldens Bridge, NY 10526
    39 Park Rd, Goldens Bridge, NY 10526
    39 Park Rd, Goldens Bridge, NY 10526
    /34

    $599,900

    Pending
    • 2 Beds
    • 2 Baths
    • 1,308 Sq Ft

    39 Park Rd, Goldens Bridge, NY 10526

    Sophisticated, beautifully renovated 2-bedroom, 2-bath semi-attached residence in the highly desirable Wild Oaks community, offering breathtaking sunset and serene wooded views with an expansive private backyard. This light-filled, move-in ready home combines timeless elegance with modern upgrades in a peaceful, natural setting.The interior showcases rich hardwood floors, crown moldings, and

    Teresa Chang Houlihan Lawrence Inc.

    39 Park Rd, Goldens Bridge, NY 10526
  • 230 Spring St, South Salem, NY 10590

    $1,440,000

    Sold Feb 18, 2026

    230 Spring St, South Salem, NY 10590

    • 3 Beds
    • 3.5 Baths
    • 3,532 Sq Ft
    • Built 2012

    Last Sold Summary

    • 4% Below List Price
    • $408/SF
    • 56 Days On Market

    Current Estimated Value $1,464,694

    Last Listing Agent Kristina Pepdjonovic Julia B Fee Sothebys Int. Rlty

    230 Spring St, South Salem, NY 10590
  • 48 Winterberry Cir, Cross River, NY 10518
    48 Winterberry Cir, Cross River, NY 10518
    48 Winterberry Cir, Cross River, NY 10518
    /21

    $599,000

    Pending
    • 2 Beds
    • 2.5 Baths
    • 1,570 Sq Ft

    48 Winterberry Cir, Cross River, NY 10518

    Welcome to this beautifully maintained end-unit in The Meadows. Offering 2 bedrooms and 2.5 baths, this spacious home combines comfort, privacy, and convenience. The updated kitchen features wood cabinetry and granite countertops. The open floor plan creates a seamless transition from the dining room into a cozy living room with a fireplace. Sliding glass doors lead to a private deck, perfect for

    Mark Boyland Keller Williams Realty Partner

    48 Winterberry Cir, Cross River, NY 10518
  • 2 Woodway Rd, South Salem, NY 10590

    $545,000

    Sold Jul 28, 2025

    2 Woodway Rd, South Salem, NY 10590

    • 4 Beds
    • 2.5 Baths
    • 2,037 Sq Ft
    • Built 1800

    Last Sold Summary

    • 5% Above List Price
    • $268/SF
    • 13 Days On Market

    Current Estimated Value $589,101

    Last Listing Agent Ghylaine Manning Vincent & Whittemore R.E.

    2 Woodway Rd, South Salem, NY 10590

Showing Results 121 - 160, Page 4 of 18

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