Lewisboro, NY Homes

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  /39

  $1,250,000 Open Sat 1PM - 4PM

  • 3 Beds
  • 2.5 Baths
  • 3,522 Sq Ft

  6 Orchard Dr, South Salem, NY 10590

  LAKE COMMUNITY SOPHISTICATION. An exceptional opportunity within the deeded Twin Lakes Village. Perfectly positioned on a private, level half-acre, this home offers a premier lifestyle with exclusive lake privileges and access to a private community beachfront, boat launch, and docks. A masterfully maintained Country Colonial featuring airy, sun-filled spaces and an open floor plan designed for

  Colleen Hickey Giner Real Estate Inc.

  6 Orchard Dr, South Salem, NY 10590
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  /29

  $2,300 per month

  • 1 Bed
  • 1 Bath
  • 675 Sq Ft
  • Property for Rent

  10 Wild Oaks Rd Unit 124, Goldens Bridge, NY 10526

  Beautiful one bedroom in Goldens Bridge in Wild Oaks area. Not finished yet but a good idea can be had from viewing. The owner can explain what the kitchen will look like. Will be available for move in on April 1 . Easy app process must be done with board . Credit will be run and paperwork as to proof of income must be shown. Totally renovated. Close to parking. Short short walk. Looks upon nice

  Joan Cotrone ERA Insite Realty Services

  10 Wild Oaks Rd Unit 124, Goldens Bridge, NY 10526
• 

  $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 $441,517

  Last Listing Agent Mark Boyland Keller Williams Realty Partner

  45 Old Bedford Rd, Goldens Bridge, NY 10526
• 

  Est $1,070,106 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

  • 24% Above List Price
  • $410/SF
  • 172 Days On Market

  Last Sold Price $860,000

  Last Listing Agent Heather Crabtree Coldwell Banker Realty
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  /28

  $1,695,000 Open Thu 1PM - 3PM

  • 3 Beds
  • 2 Baths
  • 2,778 Sq Ft

  58 Twin Lakes Rd, South Salem, NY 10590

  Set along the shoreline of Lake Oscaleta, this direct waterfront home offers a rare combination of privacy, natural beauty, and truly usable lakefront property in the heart of South Salem. Occupying .564 acres with sweeping frontage on one of the area’s most peaceful glacial lakes, the setting is defined by something increasingly hard to find - an expansive, level lawn that extends all the way to

  Adam Hade Compass Greater NY, LLC

  58 Twin Lakes Rd, South Salem, NY 10590
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  /17

  $15,000 per month

  • 3 Beds
  • 3 Baths
  • 2,435 Sq Ft
  • House for Rent

  49 Twin Lakes Rd, South Salem, NY 10590

  Dramatic Lakefront Retreat. Country Contemporary overlooking the clean, clear waters of Lake Rippowam and the Mountain Lakes Park. Spacious wrap-around deck for summer barbecues with steps down to swimming dock and firepit. Sun-filled interior with wonderful open floorplan designed for entertaining. Dramatic Living Room with soaring, skylit ceiling and fireplace. Open Dining Room with easy

  Cristina Civetta Ginnel Real Estate

  49 Twin Lakes Rd, South Salem, NY 10590
• 

  $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 $980,610

  Last Listing Agent Mary Anne Condon Ginnel Real Estate

  9 Upland Ct, South Salem, NY 10590
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  Est $391,698 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

  • 54% Above List Price
  • $316/SF
  • 265 Days On Market

  Last Sold Price $255,000

  Last Listing Agent Eric Rosenfeld William Raveis-New York LLC
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  /23

  $1,295,000

  • 4 Beds
  • 2.5 Baths
  • 2,476 Sq Ft

  12 Skytop Dr, Katonah, NY 10536

  Live the Lake Katonah life in this spacious, fully renovated mid-century modern with incredible views. This house embraces open concept living at its best. The great room has direct access out to the spectacular screened porch from both the living and dining rooms and a brand new deck is directly off of the huge eat-in-kitchen. Enjoy the lovely level backyard for great outdoor activities. Walk to

  Angela Kessel Houlihan Lawrence Inc.

  12 Skytop Dr, Katonah, NY 10536
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  /38

  $15,000 per month

  • 3 Beds
  • 2 Baths
  • 1,866 Sq Ft
  • House for Rent

  34 Twin Lakes Rd, South Salem, NY 10590

  Fully Furnished Seasonal Rental May -Oct. 31. Enjoy your summer on the lake in this remarkable waterfront single-family home. Offering the perfect combination of space, comfort, and timeless charm, this property provides an idyllic lakefront experience. The home features three bedrooms plus a den/office, with sliders that open to a spacious deck overlooking the water—perfect for indoor-outdoor

  Patty Wagner Compass Greater NY, LLC

  34 Twin Lakes 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 $1,497,783

  Last Listing Agent Mark Boyland Keller Williams Realty Partner

  136 Elmwood Rd, South Salem, NY 10590
• 

  Est $944,040 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

  • 11% Above List Price
  • $560/SF
  • 102 Days On Market

  Last Sold Price $849,000

  Last Listing Agent Gina Cooney Giner Real Estate Inc.
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  /31

  $1,295,000 Pending

  • 3 Beds
  • 3 Baths
  • 2,800 Sq Ft

  26 Gilbert St, South Salem, NY 10590

  Lakefront Lakehouse Retreat – 52 Miles to Midtown NYC Experience the perfect blend of tranquility and convenience in this stunning lakehouse just 52 miles to Midtown Manhattan—an exceptional opportunity for a full-time residence or weekend escape close to NYC. Set on nearly a half-acre with approximately 140 feet of private lake frontage on beautiful Truesdale Lake, this charming lakefront home

  Francine Liza Tuxedo Hudson Realty Corp

  26 Gilbert St, South Salem, NY 10590
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  /35

  $5,500 per month

  • 3 Beds
  • 1 Bath
  • 1,300 Sq Ft
  • House for Rent

  9 S Shore Dr, South Salem, NY 10590

  Lakeside Retreat - where you can get away from it all! Relax with the family at this peaceful fully furnished home. This is a 3 Bedroom that features a newly renovated open floor plan of kitchen, den, fireplace and living room with lake views and a beautiful back deck overlooking Lake Waccabuc. Enjoy the water views from your private dock on the lake. Washer/Dryer, Large Deck with grill, kayaks

  Gina Cooney Giner Real Estate Inc.

  9 S Shore 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 $597,291

  Last Listing Agent James Garcia Coldwell Banker Realty

  158 Jay Ct Unit 158C, Cross River, NY 10518
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  Est $498,534 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

  • 16% Above List Price
  • $614/SF
  • 48 Days On Market

  Last Sold Price $430,000

  Last Listing Agent Patricia Hinkley Coldwell Banker Realty
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  /38

  $619,000

  • 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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  /26

  $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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  $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 $426,007

  Last Listing Agent Eric Staub Keller Williams NY Realty

  52 Bittersweet Ln, South Salem, NY 10590
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  Est $813,580 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

  • 4% Above List Price
  • $556/SF
  • 62 Days On Market

  Last Sold Price $783,000

  Last Listing Agent Melissa Marcogliese Compass Greater NY, LLC
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  /27

  $799,000

  • 3 Beds
  • 2 Baths
  • 2,160 Sq Ft

  3 Mark Mead Rd, Cross River, NY 10518

  Welcome to 3 Mark Mead Road, a sunlit, incredibly spacious home in the adorable hamlet of Cross River. This fully renovated, 2160sq ft home lives much larger than a typical 3 bedroom, 2 bathroom home. The first floor bedroom, 2 second floor bedrooms, and 2 second floor offices/dens ensure there is plenty of space for everyone! The renovated kitchen, with breakfast area featuring whitewashed

  Patricia Hinkley Coldwell Banker Realty

  3 Mark Mead Rd, Cross River, NY 10518
• 

  $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 $1,221,355 Not Listed For Sale

  9 Tommys Ln, South Salem, NY 10590

  • 4 Beds
  • 3.5 Baths
  • 3,389 Sq Ft
  • Built 1976

  9 Tommys Ln, South Salem, NY 10590

  Last Sold Summary

  • 16% Above List Price
  • $311/SF
  • 12 Days On Market

  Last Sold Price $1,053,000

  Last Listing Agent Mark Boyland Keller Williams Realty Partner
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  /50

  $5,450,000 Pending

  • 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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  $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 $766,315

  Last Listing Agent Maureen Connolly Coldwell Banker Realty

  17 Kingswood Way, South Salem, NY 10590
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  Est $402,672 Not Listed For Sale

  274 Maplewood Dr Unit 32274, South Salem, NY 10590

  • 1 Bed
  • 1 Bath
  • 970 Sq Ft
  • Built 1994

  274 Maplewood Dr Unit 32274, South Salem, NY 10590

  Last Sold Summary

  • 10% Above List Price
  • $376/SF
  • 40 Days On Market

  Last Sold Price $365,000

  Last Listing Agent Alex Mashkin Keller Williams Realty Partner
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  /15

  $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
• 

  $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 $961,123

  Last Listing Agent Patricia Hinkley Coldwell Banker Realty

  1 Harriet Ln, Goldens Bridge, NY 10526
• 

  Est $407,464 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

  • 13% Above List Price
  • $362/SF
  • 45 Days On Market

  Last Sold Price $360,000

  Last Listing Agent Alex Mashkin Keller Williams Realty Partner
• 

  

  /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
• 

  $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 $998,586

  Last Listing Agent Julia Klagsbrun Corcoran Legends Realty

  6 Manor Dr, Goldens Bridge, NY 10526
• 

  Est $553,715 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

  • 1% Above List Price
  • $375/SF
  • 6 Days On Market

  Last Sold Price $550,000

  Last Listing Agent Amanda Goldberg William Raveis-New York, LLC
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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
• 

  $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 $928,611

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

  123 East St, South Salem, NY 10590
• 

  Est $281,486 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

  • 34% Above List Price
  • $329/SF
  • 14 Days On Market

  Last Sold Price $209,532

  Last Listing Agent Teresa Rivers Coldwell Banker Realty
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  /7

  $415,000

  • 3 Beds
  • 1 Bath
  • 924 Sq Ft

  10 Beech Rd, South Salem, NY 10590

  Calling all investors, builders, and contractors. 10 Beech Road presents a prime value-add opportunity on a quiet dead-end road in the desirable Lake Kitchawan community. This 3-bedroom home situated on approximately 0.43 acres is ready for renovation and ideal for cash buyers or purchasers using a rehab loan looking to create value. As a member of the Lake Kitchawan Association, owners enjoy

  Anna Proctor Compass Greater NY, LLC

  10 Beech 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 $498,213

  Last Listing Agent Cate Hegarty Compass Greater NY, LLC

  99 Fox Run, South Salem, NY 10590
• 

  Est $368,138 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

  • 12% Above List Price
  • $332/SF
  • 32 Days On Market

  Last Sold Price $330,000

  Last Listing Agent Mark Boyland Keller Williams Realty Partner
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  /14

  $595,000 Pending

  • 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
• 

  $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 $5,137,035

  Last Listing Agent Benjamin Ginnel Ginnel Real Estate

  76 E Ridge Rd, Waccabuc, NY 10597

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