Lewisboro, NY Homes

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  /39

  $1,175,000

  Pending

  • 4 Beds
  • 2.5 Baths
  • 2,922 Sq Ft

  2 Southwind Dr, Cross River, NY 10518

  Awesome House Alert! Welcome to 2 Southwind Drive — a beautifully reimagined 4-bedroom, 2.5-bath residence that seamlessly blends modern design with comfortable everyday living. Thoughtfully updated by the current owners, this home offers three separate living spaces, providing exceptional flexibility for entertaining, relaxing, or working from home.The fully renovated kitchen showcases sleek

  Lizette Sinhart Christie's Int. Real Estate

  2 Southwind Dr, Cross River, NY 10518
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• 

  

  

  /36

  $6,500 Per Month

  • 2 Beds
  • 1.5 Baths
  • 1,101 Sq Ft
  • House for Rent

  53 Cove Rd, South Salem, NY 10590

  Enjoy Waccabuc Lake just in time for summer! Escape to an exceptional year-round retreat in this beautifully renovated 2-bedroom cottage, where timeless charm meets modern comfort in one of Westchester’s most desirable lake communities on Lake Waccabuc. Thoughtfully redesigned this enchanting home offers the perfect balance of relaxation, recreation, and refined country living. At the heart of

  Gina Cooney Giner Real Estate Inc.

  53 Cove Rd, South Salem, NY 10590
• 

  $1,510,000

  Sold Mar 03, 2026

  136 Elmwood Rd, South Salem, NY 10590

  • 5 Beds
  • 5.5 Baths
  • 5,687 Sq Ft
  • Built 1873

  Last Sold Summary

  • 1% Above List Price
  • $266/SF
  • 32 Days On Market

  Current Estimated Value $1,498,647

  Last Listing Agent Mark Boyland Keller Williams Realty Partner

  136 Elmwood Rd, South Salem, NY 10590
• 

  Est $4,367,991

  Not Listed For Sale

  189 Mead St, Waccabuc, NY 10597

  • 5 Beds
  • 6 Baths
  • 5,849 Sq Ft
  • Built 2009

  189 Mead St, Waccabuc, NY 10597

  Last Sold Summary

  • 174 Days On Market
• 

  

  

  /43

  $950,000

  • 4 Beds
  • 3 Baths
  • 2,490 Sq Ft

  1 Sabbath Day Hill Rd, South Salem, NY 10590

  From the moment you turn down the long, secluded driveway toward 1 Sabbath Day Hill Rd, the feeling is unmistakable: this is a retreat built for those who prize privacy, elevation, and quiet grandeur. Perched atop its own hill and surrounded by mature trees, the home sits back from the road with views visible from the wide front porch—a space that feels like your own private veranda overlooking

  Alex Mashkin Keller Williams Realty Partner

  1 Sabbath Day Hill Rd, South Salem, NY 10590
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  /30

  $6,400 Per Month

  • 3 Beds
  • 2 Baths
  • 2,124 Sq Ft
  • Apartment for Rent

  904 Oakridge Dr, South Salem, NY 10590

  Welcome to Lakeview Lofts - A newly constructed collection of Boutique Luxury Waterfront rental residences in South Salem, offering refined one-level living in a peaceful natural setting. These exceptional residences offer sweeping water views and private waterfront patios surrounded by lush landscaping, this is where glowing sunsets become part of your daily routine. Thoughtfully designed for

  Elaine Voss Coldwell Banker Realty

  904 Oakridge Dr, South Salem, NY 10590
• 

  $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 $600,675

  Last Listing Agent James Garcia Coldwell Banker Realty

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

  Est $890,679

  Not Listed For Sale

  39 Deerfield Rd, Katonah, NY 10536

  • 3 Beds
  • 3 Baths
  • 1,889 Sq Ft
  • Built 1973

  39 Deerfield Rd, Katonah, NY 10536

  Last Sold Summary

  • 13 Days On Market
• 

  

  /49

  $1,295,000

  Pending

  • 4 Beds
  • 2.5 Baths
  • 3,504 Sq Ft

  127 Smith Ridge Rd, South Salem, NY 10590

  The Ideal Country Colonial in South Salem. Built in 2003 and impeccably maintained, this turn-key 4-bedroom, 3-bath Colonial offers 4,534 total sqft (3504 sqft + 1,030 additional sqft finished walk out lower level) light-filled, airy interiors and a timeless layout designed for today’s lifestyle. Set on two serene acres with level lawns, flowering plantings and mature trees. The home is set well

  Maryanne Durr Coldwell Banker Realty

  127 Smith Ridge Rd, South Salem, NY 10590
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  /41

  $4,600 Per Month

  • 2 Beds
  • 2.5 Baths
  • 1,568 Sq Ft
  • Townhouse for Rent

  280 Boulder Ridge Rd Unit 2F, South Salem, NY 10590

  Tucked into a picturesque wooded hillside in sought after South Salem, NY, this pet friendly, immaculate, upgraded townhouse style condo with 2 bedrooms plus an office/den offers and large storage room offers a rare blend of tranquility, style, and modern convenience. Built in 2017 and set within a beautifully landscaped, park-like community, the residence is surrounded by nature creating a true

  Amy Wilhelm Corcoran Baer & McIntosh

  280 Boulder Ridge Rd Unit 2F, South Salem, NY 10590
• 

  $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 $426,031

  Last Listing Agent Eric Staub Keller Williams NY Realty

  52 Bittersweet Ln, South Salem, NY 10590
• 

  Est $1,044,934

  Not Listed For Sale

  48 Schoolhouse Rd, Waccabuc, NY 10597

  • 3 Beds
  • 2.5 Baths
  • 2,100 Sq Ft
  • Built 1964

  48 Schoolhouse Rd, Waccabuc, NY 10597

  Last Sold Summary

  • 172 Days On Market
• 

  

  /41

  $1,300,000

  • 3 Beds
  • 2.5 Baths
  • 1,852 Sq Ft

  56 Lake Shore Dr, South Salem, NY 10590

  Nestled in a desirable South Salem lakefront enclave, this masterfully renovated Craftsman-style residence represents a rare opportunity for the discerning buyer. Spanning 1,852 square feet, the three-bedroom, two-and-a-half-bath home has been thoroughly reimagined, artfully balancing timeless charm with upscale refinement.The heart of the home is a chef-caliber kitchen equipped with stone

  Anthony Ardino William Raveis Real Estate

  56 Lake Shore Dr, South Salem, NY 10590
• 

  $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 $607,120

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

  59 Grandview Rd, South Salem, NY 10590
• 

  Est $330,172

  Not Listed For Sale

  15 Bishop Park Rd, Pound Ridge, NY 10576

  • 1 Bed
  • 1 Bath
  • 807 Sq Ft
  • Built 1934

  15 Bishop Park Rd, Pound Ridge, NY 10576

  Last Sold Summary

  • 265 Days On Market
• 

  

  /27

  $2,295,000

  Pending

  • 4 Beds
  • 3.5 Baths
  • 3,324 Sq Ft

  12 E Ridge Rd, Waccabuc, NY 10597

  Privately set on 4.5 acres along coveted East Ridge Road in the heart of Waccabuc, this beautifully updated residence offers an exceptional balance of tranquility, comfort, and refined country living.Sunlight fills the home’s open, inviting layout, designed for both relaxed everyday living and effortless entertaining. The residence features four bedrooms and three-and-a-half baths,

  Angela Kessel Houlihan Lawrence Inc.

  12 E Ridge Rd, Waccabuc, NY 10597
• 

  $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 $767,293

  Last Listing Agent Maureen Connolly Coldwell Banker Realty

  17 Kingswood Way, South Salem, NY 10590
• 

  Est $890,308

  Not Listed For Sale

  15 S Shore Dr, South Salem, NY 10590

  • 2 Beds
  • 1 Bath
  • 1,515 Sq Ft
  • Built 1920

  15 S Shore Dr, South Salem, NY 10590

  Last Sold Summary

  • 102 Days On Market
• 

  

  /6

  $295,000

  $54K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 900 Sq Ft

  102 Lake Kitchawan Dr, South Salem, NY 10590

  Sold as is, house needs total renovation. Can get a construction loan if you qualify. Backs up to the Leon Levy Preserve, access to Lake Kitchawan Lake. Tucked away along the quiet shoreline of Lake Kitchawan, this modest cape presents a rare chance to reimagine a home in one of Northern Westchester most natural settings. Set on a small parcel that backs directly onto the protected woodlands of

  Cecilia Heller Houlihan Lawrence Inc.

  102 Lake Kitchawan Dr, South Salem, NY 10590
• 

  $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 $979,832

  Last Listing Agent Patricia Hinkley Coldwell Banker Realty

  1 Harriet Ln, Goldens Bridge, NY 10526
• 

  Est $460,031

  Not Listed For Sale

  43 S Shore Dr, South Salem, NY 10590

  • 2 Beds
  • 1 Bath
  • 700 Sq Ft
  • Built 1910

  43 S Shore Dr, South Salem, NY 10590

  Last Sold Summary

  • 48 Days On Market
• 

  

  /19

  $695,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,393 Sq Ft

  95 Main St, South Salem, NY 10590

  Western View. Over one park-like acre with rolling lawns, flowering plantings and towering trees. First time listed in years, distinctive Country House with elements of a classic deck house. Warm interior spaces with hardwood floors and vaulted ceilings finished in wood. Sun-filled Living Room with fireplace and doors to front deck, ideal for relaxation. Dining Room with vaulted ceiling. Country

  Peter Michaelis Ginnel Real Estate

  95 Main St, South Salem, NY 10590
• 

  $550,000

  Sold Jun 08, 2026

  119 Willow Ct, Cross River, NY 10518

  • 1 Bed
  • 1.5 Baths
  • 1,451 Sq Ft
  • Built 1987

  Last Sold Summary

  • $379/SF
  • 21 Days On Market

  Current Estimated Value $522,775

  Last Listing Agent Frederick Cindrich Giner Real Estate Inc.

  119 Willow Ct, Cross River, NY 10518
• 

  Est $786,396

  Not Listed For Sale

  10 Tommys Ln, South Salem, NY 10590

  • 3 Beds
  • 2 Baths
  • 1,408 Sq Ft
  • Built 1960

  10 Tommys Ln, South Salem, NY 10590

  Last Sold Summary

  • 62 Days On Market
• 

  

  /7

  $75,000

  • Land
  • 3.63 Acres
  • $20,661 per Acre

  0 Laurie Ln Unit KEY000152, Lewisboro, NY 10590

  Selling as is. Amazing opportunity to build new construction on 3.6 acres in the town of Lewisboro. Quiet neighborhood setting. Prior BOHA approval is dated 1986. Old BOHA is located in Documents

  Jayne Morelock Howard Hanna Rand Realty

  0 Laurie Ln Unit KEY000152, Lewisboro, NY 10590
• 

  $1,531,781

  Sold Jun 18, 2026

  164 Spring St, South Salem, NY 10590

  • 4 Beds
  • 3.5 Baths
  • 3,697 Sq Ft
  • Built 1970

  Last Sold Summary

  • 2% Above List Price
  • $414/SF
  • 23 Days On Market

  Current Estimated Value $1,437,371

  Last Listing Agent Cecilia Heller Houlihan Lawrence Inc.

  164 Spring St, South Salem, NY 10590
• 

  Est $389,001

  Not Listed For Sale

  244 Deer Hill Unit 27244, South Salem, NY 10590

  • 1 Bed
  • 1 Bath
  • 994 Sq Ft
  • Built 1988

  244 Deer Hill Unit 27244, South Salem, NY 10590

  Last Sold Summary

  • 45 Days On Market
• 

  

  /30

  $1,795,000

  Pending

  • 4 Beds
  • 4.5 Baths
  • 5,960 Sq Ft

  2 Bluestone Ln, South Salem, NY 10590

  This modern 4BR Colonial reimagines classic country living with an effortless work/lifebalance. Privately sited with easy access to shopping, dining, culture and transportation inboth Connecticut and New York, the 3.48-acre property includes a personal trailhead to 7+miles of maintained hiking paths on 370 adjacent Westchester Land Trust and Leon LevyPreserve acres! Bluestone Lane

  Susan Stillman Houlihan Lawrence Inc.

  2 Bluestone Ln, South Salem, NY 10590
• 

  $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 $891,076

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

  123 East St, South Salem, NY 10590
• 

  Est $515,144

  Not Listed For Sale

  230 Lakeside Dr, South Salem, NY 10590

  • 2 Beds
  • 2 Baths
  • 1,468 Sq Ft
  • Built 1987

  230 Lakeside Dr, South Salem, NY 10590

  Last Sold Summary

  • 6 Days On Market
• 

  

  /8

  $650,000

  • 3 Beds
  • 1.5 Baths
  • 1,456 Sq Ft

  4 Lorraine Rd, South Salem, NY 10590

  Welcome to South Salem! Nestled on a picturesque 1.09 acre, this inviting split-level home offers the perfect combination of privacy, and everyday convenience on a spacious private lot.The main level features a bright and open design with a modern eat-in kitchen, dining area, and a living room anchored by a fireplace — creating the ideal setting for both quiet evenings and effortless

  Carine Nowak Compass Greater NY, LLC

  4 Lorraine Rd, South Salem, NY 10590
• 

  $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 $493,903

  Last Listing Agent Cate Hegarty Compass Greater NY, LLC

  99 Fox Run, South Salem, NY 10590
• 

  Est $276,767

  Not Listed For Sale

  224 Lakeside Dr, South Salem, NY 10590

  • 1 Bed
  • 1 Bath
  • 637 Sq Ft
  • Built 1986

  224 Lakeside Dr, South Salem, NY 10590

  Last Sold Summary

  • 14 Days On Market
• 

  

  /43

  $695,000

  Open Sat 1PM - 3PM

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

  103 Locust Ridge, Cross River, NY 10518

  Welcome to the next level living at "The Meadows", the ultimate low maintenance, high vibe resort lifestyle. Get ready to fall in love with this beautifully upgraded 2 bedroom, 2.5 bathroom end unit-undeniably perched in the most coveted, prime location within the community. Start your mornings with a cup of coffee in the renovated kitchen bathed in morning sunlight, then move out to the

  Ellen Schwartz Julia B Fee Sothebys Int. Rlty

  103 Locust Ridge, Cross River, NY 10518
• 

  $2,700,000

  Sold Jul 29, 2025

  23 Rock Shelter Rd, Waccabuc, NY 10597

  • 5 Beds
  • 9 Baths
  • 8,552 Sq Ft
  • Built 2003

  Last Sold Summary

  • 2% Below List Price
  • $316/SF
  • 29 Days On Market

  Current Estimated Value $2,791,925

  Last Listing Agent Angela Kessel Houlihan Lawrence Inc.

  23 Rock Shelter Rd, Waccabuc, NY 10597
• 

  Est $375,287

  Not Listed For Sale

  219 Lakeside Dr, South Salem, NY 10590

  • 1 Bed
  • 1 Bath
  • 994 Sq Ft
  • Built 1987

  219 Lakeside Dr, South Salem, NY 10590

  Last Sold Summary

  • 32 Days On Market
• 

  

  /44

  $675,000

  • 2 Beds
  • 2.5 Baths
  • 1,880 Sq Ft

  169 Jay Ct Unit 160, Cross River, NY 10518

  Welcome to 169 Jay Court, a beautifully updated and meticulously maintained end-unit townhome in the highly sought-after Meadows community. Thoughtfully renovated with timeless finishes and an exceptional attention to detail, this move-in ready residence offers stylish living among three finished levels. The inviting main level features rich hardwood flooring, elegant crown molding, and a

  Laura Sterling Coldwell Banker Realty

  169 Jay Ct Unit 160, Cross River, NY 10518
• 

  $1,200,000

  Sold Dec 05, 2025

  12 Stonewall Ct, South Salem, NY 10590

  • 4 Beds
  • 3.5 Baths
  • 3,022 Sq Ft
  • Built 1969

  Last Sold Summary

  • 9% Above List Price
  • $397/SF
  • 16 Days On Market

  Current Estimated Value $1,213,927

  Last Listing Agent Richard Mishkin Coldwell Banker Realty

  12 Stonewall Ct, South Salem, NY 10590
• 

  Est $475,760

  Not Listed For Sale

  198 Laurel Ridge, South Salem, NY 10590

  • 2 Beds
  • 2 Baths
  • 1,301 Sq Ft
  • Built 1981

  198 Laurel Ridge, South Salem, NY 10590

  Last Sold Summary

  • 25 Days On Market
• 

  

  /8

  $35,000

  Pending

  • Land
  • 7,291 Sq Ft
  • $209,080 per Acre

  0 Cove Rd Unit KEY993296, Lewisboro, NY 10590

  Just in time for summer! Enjoy deeded access to private Lake Waccabuc with community docks and boat launch areas, and paddle access to Lakes Oscaleta and Rippowam. Three Lakes are natural glaciated spring-fed lakes. Three Lakes Council monitors water quality and fish stocking program. Swim, fish, paddle, sail, skate, and ice fish! Property purchase includes two stand-up paddle boards, two kayaks,

  Anne-Marie Nordgren Coldwell Banker Realty

  0 Cove Rd Unit KEY993296, Lewisboro, NY 10590

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