Lewisboro, NY Homes

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  $1,299,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 3,598 Sq Ft

  19 Ledgewood Ln, South Salem, NY 10590

  The Perfect Country Colonial. Peaceful setting at the end of a desirable cul-de-sac. Nearly three serene acres with level lawns, flowering plantings, stone walls and towering trees. Fabulous rear terrace with firepit, built-in barbecue and fridge for fun outdoor entertaining. Absolutely turn-key Colonial with light and airy rooms. Stunning interior with great circular flow, high ceilings and

  Nancy Lacavalla Ginnel Real Estate

  19 Ledgewood Ln, South Salem, NY 10590
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  $6,000 per month

  • 3 Beds
  • 3.5 Baths
  • 3,700 Sq Ft
  • House for Rent

  164 Spring St, South Salem, NY 10590

  PLEASE NOTE: This is a short season rental.Charming converted contemporary farm ranch with a spectacular stone terrace and back yard. Available 11/15/25-2/13/26 can be rented for 1-3 months at $6000 per month. There is an additional $500 per month for oil and electric. The property has a one car garage with attached cottage and a tenant, not too close to house, one garage is included in rental.

  Cecilia Heller Houlihan Lawrence Inc.

  164 Spring St, South Salem, NY 10590
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  $1,350,000 Sold Jul 30, 2025

  72 Chapel Rd, Waccabuc, NY 10597

  • 4 Beds
  • 3.5 Baths
  • 3,643 Sq Ft
  • Built 1979

  Last Sold Summary

  • 4% Above List Price
  • $371/SF
  • 5 Days On Market

  Current Estimated Value $1,363,238

  Last Listing Agent Mindy Weil Ginnel Real Estate

  72 Chapel Rd, Waccabuc, NY 10597
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  Est $936,240 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,515 Sq Ft

  15 S Shore Dr, South Salem, NY 10590

  15 S Shore Dr, South Salem, NY 10590
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  /22

  $1,195,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 3,100 Sq Ft

  4 Scenic Dr, South Salem, NY 10590

  Set on a beautifully maintained private one acre, this classic Colonial offers 4 bedrooms and 2.5 bath. Step into a spacious and inviting layout where the entry opens to a bright living room filled with natural light. A wood-burning fireplace serves as a cozy focal point, perfect for relaxing evenings or gathering with loved ones. The formal dining room provides a refined setting for hosting

  Mark Boyland Keller Williams Realty Partner

  4 Scenic Dr, South Salem, NY 10590
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  $9,000 per month

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • House for Rent

  24 Cove Rd, South Salem, NY 10590

  Welcome to The Lake! Enjoy this newly renovated home on Lake Waccabuc. Just steps to your private dock and beautiful lake community on Cove Rd. This home lends itself to water views throughout the house. Cozy open floor plan downstairs with beautiful kitchen and fireplace. 1st floor also offers a full bathroom. Side deck with lake view off of the kitchen. This home is fully furnished with

  Gina Cooney Giner Real Estate Inc.

  24 Cove Rd, South Salem, NY 10590
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  $444,000 Sold Jul 14, 2025

  45 Old Bedford Rd, Goldens Bridge, NY 10526

  • 2 Beds
  • 1 Bath
  • 850 Sq Ft
  • Built 1919

  Last Sold Summary

  • 1% Above List Price
  • $522/SF
  • 17 Days On Market

  Current Estimated Value $441,679

  Last Listing Agent Mark Boyland Keller Williams Realty Partner

  45 Old Bedford Rd, Goldens Bridge, NY 10526
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  Est $495,170 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 700 Sq Ft

  43 S Shore Dr, South Salem, NY 10590

  43 S Shore Dr, South Salem, NY 10590
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  $650,000

  • 2 Beds
  • 2.5 Baths
  • 2,626 Sq Ft

  10 Guilford Cir, Goldens Bridge, NY 10526

  Rare opportunity in desirable Katonah Close in Goldens Bridge—units here seldom come to market, so don’t miss this one. This bright, tri-level contemporary end-unit townhome offers space, privacy, and convenient living.The main level welcomes you with a two-story entry, hardwood floors and recessed lighting. Very spacious rooms throughout. Enjoy a large eat-in kitchen with a peninsula, formal

  Debra DeMelis Coldwell Banker Realty

  10 Guilford Cir, Goldens Bridge, NY 10526
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  $931,000 Sold Oct 01, 2025

  9 Upland Ct, South Salem, NY 10590

  • 4 Beds
  • 3 Baths
  • 3,200 Sq Ft
  • Built 1985

  Last Sold Summary

  • 4% Above List Price
  • $291/SF
  • 10 Days On Market

  Current Estimated Value $942,589

  Last Listing Agent Mary Anne Condon Ginnel Real Estate

  9 Upland Ct, South Salem, NY 10590
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  Est $836,333 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,408 Sq Ft

  10 Tommys Ln, South Salem, NY 10590

  10 Tommys Ln, South Salem, NY 10590
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  $599,000 Pending

  • 2 Beds
  • 2.5 Baths
  • 1,451 Sq Ft

  33 Briar Ct, Cross River, NY 10518

  This beautifully updated 2-bedroom, 2.5-bath townhouse in The Meadows blends modern comfort with exceptional amenities. Step inside to discover a fully renovated kitchen featuring leathered granite countertops, soft-close cabinetry, new appliances, and upgraded lighting. A large living room, with sliders to the deck, dining area and a freshly painted half bath complete the first floor. Upstairs

  Patricia Hinkley Coldwell Banker Realty

  33 Briar Ct, Cross River, NY 10518
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  $590,000 Sold Aug 20, 2025

  158 Jay Ct Unit 158C, Cross River, NY 10518

  • 1 Bed
  • 2.5 Baths
  • 1,751 Sq Ft
  • Built 1988

  Last Sold Summary

  • 2% Below List Price
  • $337/SF
  • 30 Days On Market

  Current Estimated Value $589,085

  Last Listing Agent James Garcia Coldwell Banker Realty

  158 Jay Ct Unit 158C, Cross River, NY 10518
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  Est $1,198,674 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,389 Sq Ft

  9 Tommys Ln, South Salem, NY 10590

  9 Tommys Ln, South Salem, NY 10590
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  /50

  $5,450,000

  • 4 Beds
  • 3.5 Baths
  • 6,161 Sq Ft

  45 Pine Hill Dr, South Salem, NY 10590

  Welcome to 45 Pine Hill Drive, where modern luxury meets timeless sophistication. This fully renovated 4-bedroom, 3.5-bath residence has been transformed into a true showpiece, offering every amenity for elevated living. Inside, discover a breathtaking open-concept kitchen by Leicht (Germany) with premium electric stainless steel appliances, dual sinks, and a striking oversized island—perfect for

  Joseph Lukic Compass Greater NY, LLC

  45 Pine Hill Dr, South Salem, NY 10590
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  $419,000 Sold Sep 29, 2025

  52 Bittersweet Ln, South Salem, NY 10590

  • 2 Beds
  • 1 Bath
  • 1,070 Sq Ft
  • Built 1981

  Last Sold Summary

  • 2% Below List Price
  • $392/SF
  • 27 Days On Market

  Current Estimated Value $428,297

  Last Listing Agent Eric Staub Keller Williams NY Realty

  52 Bittersweet Ln, South Salem, NY 10590
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  Est $440,699 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 970 Sq Ft

  274 Maplewood Dr Unit 32274, South Salem, NY 10590

  274 Maplewood Dr Unit 32274, South Salem, NY 10590
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  /16

  $385,000

  • 1 Bed
  • 1 Bath
  • 971 Sq Ft

  239 Deer Hill, South Salem, NY 10590

  Welcome to 239 Deer Hill Road in Oakridge Condominiums. This top-floor 1-bedroom, 1-bath unit offers 1,000 square feet of updated, turn-key living with low taxes and access to the sought-after Katonah-Lewisboro School District (Meadow Pond Elementary). Recent upgrades include newer appliances, refreshed flooring, and a sleek modern bathroom. The main level features a bright living room with a

  Cate Hegarty Compass Greater NY, LLC

  239 Deer Hill, South Salem, NY 10590
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  $600,000 Sold Oct 29, 2025

  59 Grandview Rd, South Salem, NY 10590

  • 3 Beds
  • 1.5 Baths
  • 1,360 Sq Ft
  • Built 1977

  Last Sold Summary

  • 14% Below List Price
  • $441/SF
  • 133 Days On Market

  Current Estimated Value $609,160

  Last Listing Agent Andres Sarmiento RE/MAX Distinguished Hms.&Prop

  59 Grandview Rd, South Salem, NY 10590
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  Est $425,349 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 994 Sq Ft

  244 Deer Hill Unit 27244, South Salem, NY 10590

  244 Deer Hill Unit 27244, South Salem, NY 10590
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  $950,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,650 Sq Ft

  14 Mark Mead Rd, Cross River, NY 10518

  Welcome to 14 Mark Mead Road — a picture-perfect Cape Cod Colonial tucked on a quiet cul-de-sac in desirable Cross River. This beautifully maintained home blends timeless style with thoughtful modern updates, offering a warm, comfortable atmosphere and exceptional attention to detail. The sunlit main level flows effortlessly from the great room with a wood-burning fireplace to the granite eat-in

  Christopher Motta Real Broker NY LLC

  14 Mark Mead Rd, Cross River, NY 10518
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  $750,000 Sold Aug 25, 2025

  17 Kingswood Way, South Salem, NY 10590

  • 3 Beds
  • 2 Baths
  • 1,690 Sq Ft
  • Built 1974

  Last Sold Summary

  • 6% Above List Price
  • $444/SF
  • 35 Days On Market

  Current Estimated Value $744,273

  Last Listing Agent Maureen Connolly Coldwell Banker Realty

  17 Kingswood Way, South Salem, NY 10590
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  Est $598,593 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,468 Sq Ft

  230 Lakeside Dr, South Salem, NY 10590

  230 Lakeside Dr, South Salem, NY 10590
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  /25

  $799,000 Pending

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

  256 Smith Ridge Rd, South Salem, NY 10590

  Presenting a rare opportunity to complete a thoughtfully designed home to your own specifications. The residence features a fully finished exterior with new roof, windows, and architectural detailing on its exterior, providing a strong foundation for a custom interior build-out. The interior is currently open and framed, allowing flexibility to modify room layout, finishes, and systems to suit

  Erin Lee Keller Williams Realty Group

  256 Smith Ridge Rd, South Salem, NY 10590
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  $950,000 Sold Jun 26, 2025

  1 Harriet Ln, Goldens Bridge, NY 10526

  • 3 Beds
  • 2 Baths
  • 2,750 Sq Ft
  • Built 1953

  Last Sold Summary

  • 13% Above List Price
  • $345/SF
  • 9 Days On Market

  Current Estimated Value $961,571

  Last Listing Agent Patricia Hinkley Coldwell Banker Realty

  1 Harriet Ln, Goldens Bridge, NY 10526
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  Est $246,147 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 637 Sq Ft

  224 Lakeside Dr, South Salem, NY 10590

  224 Lakeside Dr, South Salem, NY 10590
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  /30

  $1,475,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 3,463 Sq Ft

  7 Douglas Dr, South Salem, NY 10590

  New to the market! This four bedroom, Colonial Farmhouse with a rocking chair porch features a classic layout of rooms. There is a private and quiet, newly built in-ground pool with a large built-in shelf for sunbathing/ kids/ pets and an electric cover. The pool is dramatically sited among large natural rocks. Vintage wide board flooring reclaimed from an antique Virginia barn is

  Sally Slater Douglas Elliman Real Estate

  7 Douglas Dr, South Salem, NY 10590
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  $999,999 Sold Jun 20, 2025

  6 Manor Dr, Goldens Bridge, NY 10526

  • 4 Beds
  • 3 Baths
  • 2,476 Sq Ft
  • Built 1979

  Last Sold Summary

  • 10% Above List Price
  • $404/SF
  • 15 Days On Market

  Current Estimated Value $1,002,132

  Last Listing Agent Julia Klagsbrun Corcoran Legends Realty

  6 Manor Dr, Goldens Bridge, NY 10526
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  Est $385,177 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 994 Sq Ft

  219 Lakeside Dr, South Salem, NY 10590

  219 Lakeside Dr, South Salem, NY 10590
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  /30

  $374,999 Pending

  • 1 Bed
  • 1 Bath
  • 1,112 Sq Ft

  132 Stone Meadow, South Salem, NY 10590

  Welcome to 132 Stone Meadow, a thoughtfully designed condo nestled in the heart of South Salem’s coveted Oakridge community. With over 1,100 square feet of living space, this one-bedroom, one-bathroom home offers more than just comfort—it delivers flexibility and style. A spacious loft adds a layer of versatility, perfect for a home office, guest room, or creative studio. The open layout is

  Lisa Sgobbo Century 21 Alliance Rlty Group

  132 Stone Meadow, South Salem, NY 10590
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  $900,000 Sold Jul 31, 2025

  123 East St, South Salem, NY 10590

  • 4 Beds
  • 3.5 Baths
  • 2,950 Sq Ft
  • Built 1979

  Last Sold Summary

  • 5% Below List Price
  • $305/SF
  • 17 Days On Market

  Current Estimated Value $923,808

  Last Listing Agent Giuseppe 'Joe' Melillo William Raveis Real Estate

  123 East St, South Salem, NY 10590
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  Est $537,803 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,301 Sq Ft

  198 Laurel Ridge, South Salem, NY 10590

  198 Laurel Ridge, South Salem, NY 10590
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  /14

  $595,000

  • 1 Bed
  • 1 Bath
  • 776 Sq Ft

  10 Skytop Dr, Katonah, NY 10536

  Live the Katonah lake life in this absolutely charming, fully renovated cottage. A huge stone fireplace and cathedral ceiling are the focal points of this gem which has beautiful hardwood floors and a great kitchen and bath as well. Relax and watch the world go by from the expansive, picturesque rocking chair front porch and enjoy the lovely backyard for great outdoor living. Walk to the lake to

  Angela Kessel Houlihan Lawrence Inc.

  10 Skytop Dr, Katonah, NY 10536
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  $504,000 Sold Oct 28, 2025

  99 Fox Run, South Salem, NY 10590

  • 2 Beds
  • 1 Bath
  • 1,364 Sq Ft
  • Built 1981

  Last Sold Summary

  • 2% Above List Price
  • $370/SF
  • 20 Days On Market

  Current Estimated Value $496,323

  Last Listing Agent Cate Hegarty Compass Greater NY, LLC

  99 Fox Run, South Salem, NY 10590
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  Est $433,972 Not Listed For Sale

  • 1 Bed
  • 2 Baths
  • 1,112 Sq Ft

  192 Laurel Ridge, South Salem, NY 10590

  192 Laurel Ridge, South Salem, NY 10590
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  /21

  $389,000 Pending

  • 1 Bed
  • 1 Bath
  • 1,000 Sq Ft

  50 S Shore Dr, South Salem, NY 10590

  Charming lake-area cottage offering an inviting retreat in the heart of South Salem. It lives like a two-bedroom, with two bonus rooms that can serve as an office, guest space, or creative studio. Enjoy lake rights with access to a private dock—perfect for relaxing, kayaking, or soaking in the serene water views. The property includes a carport and a driveway accommodating two to three cars,

  Mark Boyland Keller Williams Realty Partner

  50 S Shore Dr, South Salem, NY 10590
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  $5,400,000 Sold Jun 16, 2025

  76 E Ridge Rd, Waccabuc, NY 10597

  • 6 Beds
  • 8 Baths
  • 6,211 Sq Ft
  • Built 2025

  Last Sold Summary

  • 2% Below List Price
  • $869/SF
  • 23 Days On Market

  Current Estimated Value $5,138,093

  Last Listing Agent Benjamin Ginnel Ginnel Real Estate

  76 E Ridge Rd, Waccabuc, NY 10597
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  Est $289,933 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 660 Sq Ft

  176 Laurel Ridge Unit 19176, South Salem, NY 10590

  176 Laurel Ridge Unit 19176, South Salem, NY 10590
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  /46

  $949,000

  • 4 Beds
  • 2 Baths
  • 1,572 Sq Ft

  54 Lockwood Rd, South Salem, NY 10590

  A Picture-Perfect Oasis on 3.46 Private Acres in South Salem!Welcome to your own private sanctuary—a meticulously maintained 1,972-square-foot retreat where nature meets elegance at every turn. Built in 1965 and lovingly cared for ever since, this exceptional South Salem property offers the rare combination of tranquil seclusion and premier location in the sought-after Katonah-Lewisboro

  AnnMarie Sementilli Julia B Fee Sothebys Int. Rlty

  54 Lockwood Rd, South Salem, NY 10590
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  $500,000 Sold Feb 20, 2025

  451 Smith Ridge Rd, South Salem, NY 10590

  • 3 Beds
  • 1.5 Baths
  • 864 Sq Ft
  • Built 1951

  Last Sold Summary

  • 13% Below List Price
  • $579/SF
  • 70 Days On Market

  Current Estimated Value $582,819

  Last Listing Agent Tony Segno Howard Hanna NYC LLC

  451 Smith Ridge Rd, South Salem, NY 10590

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