Lewisboro, NY Homes

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  $2,500,000

  $200K PRICE DROP

  • 6 Beds
  • 7.5 Baths
  • 8,900 Sq Ft

  11 Lost Nations Rd, Pound Ridge, NY 10576

  Set on over two spectacular acres in a premier location in Pound Ridge, this custom built Colonial offers an extraordinary blend of scale, craftsmanship, and complete privacy. Tucked along a quiet country road, this home has exquisite architectural detail throughout that includes extensive custom millwork, gleaming hardwood floors, soaring ceilings, and spacious rooms that create an atmosphere of

  

  Nikki McMann

  William Raveis-New York LLC

  11 Lost Nations Rd, Pound Ridge, NY 10576
• Explore Lewisboro

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  /20

  $5,185 Per Month

  • 3 Beds
  • 3 Baths
  • 2,433 Sq Ft
  • Townhouse for Rent

  1 The Meadows, Cross River, NY 10518

  Property Id: 492831 Townhouse 3BR / 2.5 bath 2433 sq ft Recently Renovated w finished basement - Pets are welcome! Townhouse / condo in "The Meadows" Katonah - Lewisboro schools Increase Miller elementary John Jay MS John Jay HS New wide plank HW oak flooring throughout New "soft close" cabinets in kitchen w quartz countertops w subway tile

  1 The Meadows, Cross River, NY 10518
• 

  $510,000

  Sold Aug 18, 2025

  125 Woodcock Knolls, Cross River, NY 10518

  • 2 Beds
  • 2.5 Baths
  • 1,570 Sq Ft
  • Built 1987

  Last Sold Summary

  • 1% Above List Price
  • $325/SF
  • 13 Days On Market

  Current Estimated Value $550,642

  Last Listing Agent Kyle Neumann Houlihan Lawrence Inc.

  125 Woodcock Knolls, Cross River, NY 10518
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  Est $1,708,893

  Not Listed For Sale

  10 Shoshone Dr, Katonah, NY 10536

  • 5 Beds
  • 4.5 Baths
  • 4,395 Sq Ft
  • Built 1988

  10 Shoshone Dr, Katonah, NY 10536

  Last Sold Summary

  • 13 Days On Market

  Last Listing Agent Randy Calano Keller Williams Realty Partner
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  /12

  $835,000

  • 2 Beds
  • 1.5 Baths
  • 1,487 Sq Ft

  8 Hoyt St, South Salem, NY 10590

  A rare opportunity in the charming Truesdale Lake community of South Salem. This quaint cottage is in need of renovation and is being sold as-is, offering outstanding potential for restoration, investment, or new construction. Truesdale Lake is an 83-acre private lake community known for its peaceful setting, natural beauty, and long-established neighborhood character. Located in the Town of

  Jessica Lane

  Serhant LLC

  8 Hoyt St, South Salem, NY 10590
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  /23

  $6,500 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,896 Sq Ft
  • House for Rent

  1 Branch St, Goldens Bridge, NY 10526

  Enjoy a perfect weekend escape or year-round lake living! This 3-bedroom contemporary, artist-owned cottage is nestled in the heart of Goldens Bridge Colony, surrounded by 17 acres with lake rights, swimming, clubhouse, summer camp, hiking trails, and so much more. This home offers a perfect blend of modern design with a tranquil cabin charm. Features include: high-pitched ceilings, working

  Peter Giner Giner Real Estate Inc.

  1 Branch St, Goldens Bridge, NY 10526
• 

  $780,000

  Sold Jul 15, 2026

  7 Guilford Cir, Goldens Bridge, NY 10526

  • 2 Beds
  • 2.5 Baths
  • 2,475 Sq Ft
  • Built 1993

  Last Sold Summary

  • 16% Above List Price
  • $315/SF
  • 17 Days On Market

  Current Estimated Value $673,976

  Last Listing Agent Ellen Schwartz Julia B Fee Sothebys Int. Rlty

  7 Guilford Cir, Goldens Bridge, NY 10526
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  Est $1,462,329

  Not Listed For Sale

  5 Jonas Ln, Katonah, NY 10536

  • 4 Beds
  • 3.5 Baths
  • 3,483 Sq Ft
  • Built 1940

  5 Jonas Ln, Katonah, NY 10536

  Last Sold Summary

  • 49 Days On Market

  Last Listing Agent Nelson Salazar Coldwell Banker Realty
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  /30

  $1,295,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 3,200 Sq Ft

  124 East St, South Salem, NY 10590

  HIDEOUT HILL. Part of South Salem’s rich history. Circa 1740 Antique Colonial and one of the area’s oldest homes. Brimming with period details including wide board floors, two fireplaces and period moldings. Tastefully renovated in 2020 carefully marrying the old with the new. 3200 square feet of living space with beautifully proportioned rooms rich in detailing. Exceptionally appointed interior

  Lisa Fitz Ginnel Real Estate

  124 East St, South Salem, NY 10590
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  /33

  $28,000 Per Month

  • 4 Beds
  • 3 Baths
  • 3,476 Sq Ft
  • House for Rent

  50 Cove Rd, South Salem, NY 10590

  Enjoy this beautifully furnished 4+ Bedroom home on Lake Waccabuc, available just in time for summer! Nestled on one of Northern Westchester’s most sought-after lakes, this inviting retreat offers the perfect blend of comfort, relaxation, and breathtaking waterfront views. Wake up to lake views throughout the home and spend your days swimming, kayaking, paddle boarding, fishing, or simply

  Gina Cooney Giner Real Estate Inc.

  50 Cove Rd, South Salem, NY 10590
• 

  $2,200,000

  Sold Oct 30, 2025

  38 Gilbert St, South Salem, NY 10590

  • 3 Beds
  • 2.5 Baths
  • 2,262 Sq Ft
  • Built 1926

  Last Sold Summary

  • 8% Below List Price
  • $973/SF
  • 45 Days On Market

  Current Estimated Value $2,141,686

  Last Listing Agent Mindy Weil Ginnel Real Estate

  38 Gilbert St, South Salem, NY 10590
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  Est $641,129

  Not Listed For Sale

  280 Boulder Ridge Rd, South Salem, NY 10590

  • 2 Beds
  • 2.5 Baths
  • 1,568 Sq Ft
  • Built 2017

  280 Boulder Ridge Rd, South Salem, NY 10590

  Last Sold Summary

  • 24 Days On Market

  Last Listing Agent Susan O'Brien Houlihan Lawrence Inc.
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  /43

  $699,000

  Pending

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

  8 West Ln, South Salem, NY 10590

  Looking for your next investment in a sought-after hamlet of Northern Westchester County? Or hoping to buy a home you can customize yourself? This property would be the ideal scenario. A truly rare offering at an even rarer price in this area. Expansive flat 2-acre lot with in-ground pool in good condition. Ideal for second floor build up in a pristine neighborhood (architectural renderings of

  Giancarlo Pecora eXp Realty

  8 West Ln, South Salem, NY 10590
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  /25

  $9,000 Per Month

  • 3 Beds
  • 2.5 Baths
  • 2,676 Sq Ft
  • House for Rent

  25 Cross Pond Rd, Pound Ridge, NY 10576

  Fantastic 3 BR home on a quiet road in Pound Ridge. Private yet close to everything. Newly renovated, this home is fresh and bright - the perfect rental. Katonah/ Lewisboro School District. Pool. Pets to be considered on individual basis with additional security. Additional Information: HeatingFuel:Oil Above Ground,ParkingFeatures:2 Car Attached.

  Marcus Fitz Ginnel Real Estate

  25 Cross Pond Rd, Pound Ridge, NY 10576
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  $855,000

  Sold Aug 20, 2025

  38 Waccabuc Rd, Goldens Bridge, NY 10526

  • 3 Beds
  • 2.5 Baths
  • 2,379 Sq Ft
  • Built 1977

  Last Sold Summary

  • 1% Above List Price
  • $359/SF
  • 41 Days On Market

  Current Estimated Value $908,553

  Last Listing Agent Michael Winter Julia B Fee Sothebys Int. Rlty

  38 Waccabuc Rd, Goldens Bridge, NY 10526
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  Not Listed For Sale

  12 Howland Dr, Cross River, NY 10518

  12 Howland Dr, Cross River, NY 10518

  Last Sold Summary

  • 228 Days On Market

  Last Listing Agent Angela Lanni Houlihan Lawrence Inc.
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  /36

  $999,999

  Pending

  • 5 Beds
  • 4.5 Baths
  • 3,100 Sq Ft

  9 Lois Ln, Katonah, NY 10536

  First time ever offered on the market! Welcome to 9 Lois Lane, a rare opportunity in one of Katonah’s most desirable settings. Located on a quiet cul-de-sac, this 5-bedroom, 4.5-bath home sits on over 2 beautiful, level acres offering privacy, space, and endless potential. The property features a spacious layout, two-car garage, in-ground pool, and an incredible flat backyard surrounded by mature

  Frank Pistecchia Keller Williams Prestige Prop

  9 Lois Ln, Katonah, NY 10536
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  /26

  $18,000 Per Month

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

  24 Cove Rd, South Salem, NY 10590

  Summer is coming! And what better place to spend it than at Waccabuc 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

  Gina Cooney Giner Real Estate Inc.

  24 Cove Rd, South Salem, NY 10590
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  $655,000

  Sold Sep 04, 2025

  48 Lockwood Rd, South Salem, NY 10590

  • 3 Beds
  • 2 Baths
  • 2,112 Sq Ft
  • Built 1965

  Last Sold Summary

  • 6% Below List Price
  • $310/SF
  • 48 Days On Market

  Current Estimated Value $700,644

  Last Listing Agent Pino Masucci Coldwell Banker Realty

  48 Lockwood Rd, South Salem, NY 10590
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  Est $287,566

  Not Listed For Sale

  462 Smith Ridge Rd, South Salem, NY 10590

  462 Smith Ridge Rd, South Salem, NY 10590

  Last Sold Summary

  • 185 Days On Market

  Last Listing Agent Nicole Orefice Compass Greater NY, LLC
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  /39

  $1,299,000

  Pending

  • 4 Beds
  • 2.5 Baths
  • 3,550 Sq Ft

  17 Pine Hill Dr, South Salem, NY 10590

  Set on 3.73 acres this elegant 4-bedroom, 2.5-bath colonial offers soaring ceilings, expansive windows and exceptional privacy. A dramatic double-height entry welcomes you into the home. A formal living room and a stunning great room with cathedral ceilings both featuring wood-burning fireplaces. The spacious kitchen is complete with a center island, breakfast nook, and access to a full house

  Patricia Hinkley Coldwell Banker Realty

  17 Pine Hill Dr, South Salem, NY 10590
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  /40

  $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 available Sept 1-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

  Patty Wagner Compass Greater NY, LLC

  34 Twin Lakes Rd, South Salem, NY 10590
• 

  $699,000

  Sold Aug 14, 2026

  75 Park Rd Extension, Goldens Bridge, NY 10526

  • 2 Beds
  • 2.5 Baths
  • 1,620 Sq Ft
  • Built 1997

  Last Sold Summary

  • $431/SF
  • 11 Days On Market

  Current Estimated Value $698,316

  Last Listing Agent Hannah Yates Giner Real Estate Inc.

  75 Park Rd Extension, Goldens Bridge, NY 10526
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  Est $2,154,558

  Not Listed For Sale

  11 Falcon Ridge Dr, Goldens Bridge, NY 10526

  • 4 Beds
  • 3.5 Baths
  • 3,848 Sq Ft
  • Built 2018

  11 Falcon Ridge Dr, Goldens Bridge, NY 10526

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Cheryl Neuburger Ginnel Real Estate
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  /18

  $599,000

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

  30 Briar Ct, Cross River, NY 10518

  Welcome to this beautifully maintained two-bedroom, two-and-a-half-bathroom townhome in The Meadows of Cross River. This inviting home offers a spacious and thoughtfully designed layout with comfortable living spaces, quality finishes, and excellent community amenities.The first floor features an inviting entry foyer, a convenient powder room, and an eat-in kitchen with granite countertops, a

  Sheila Olivieri Giaccio Luxury Properties, Inc

  30 Briar Ct, Cross River, NY 10518
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  /32

  $6,100 Per Month

  • 3 Beds
  • 2 Baths
  • 1,986 Sq Ft
  • House for Rent

  5 Howe St, South Salem, NY 10590

  Charming architectural retreat offering the perfect open-concept flow for effortless entertaining. The heart of the home is an expansive Great Room boasting soaring vaulted wood ceilings with exposed beams, rich hardwood floors, and a dramatic stone wood-burning fireplace with a raised hearth. An expansive wall of glass doors floods the space with natural light and opens seamlessly to a

  Paul Tollefson William Raveis-New York LLC

  5 Howe St, South Salem, NY 10590
• 

  $1,412,500

  Sold Jan 27, 2026

  61 Mill River Rd, South Salem, NY 10590

  • 4 Beds
  • 3.5 Baths
  • 4,447 Sq Ft
  • Built 1990

  Last Sold Summary

  • 3% Below List Price
  • $318/SF
  • 63 Days On Market

  Current Estimated Value $1,447,268

  Last Listing Agent Patricia Palumbo Coldwell Banker Realty

  61 Mill River Rd, South Salem, NY 10590
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  Not Listed For Sale

  0 Sullivan Rd Unit KEY822384, Lewisboro, NY 10560

  0 Sullivan Rd Unit KEY822384, Lewisboro, NY 10560

  Last Sold Summary

  • 20 Days On Market

  Last Listing Agent Julie Setterlund Julia B Fee Sothebys Int. Rlty
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  /49

  $1,250,000

  Pending

  • 6 Beds
  • 3.5 Baths
  • 3,468 Sq Ft

  161 Ridgefield Ave, South Salem, NY 10590

  Set on two peaceful acres at the end of a private country lane, this distinctive 6 bedroom, 3.5 bath Colonial farmhouse offers a rare blend of history, charm, and natural beauty. Bordering the western edge of the Leon Levy Preserve, the property enjoys a tranquil setting surrounded by gardens, stone walls, and open green spaces. Originally built around 1900 as the caretaker's residence for the

  Lindsay Matthews Houlihan Lawrence Inc.

  161 Ridgefield Ave, South Salem, NY 10590
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  /21

  $3,400 Per Month

  • 1 Bed
  • 1 Bath
  • 863 Sq Ft
  • House for Rent

  114 Lake Kitchawan Dr, South Salem, NY 10590

  Enjoy peaceful lake area living in this charming reverse living home, ideally located near Lake Kitchawan. This unique layout offers the kitchen and dining area on the lower level, creating a comfortable separation between entertaining and living spaces.Originally designed as a two bedroom home, it has been converted into a spacious one bedroom with an open and airy feel. The home features

  Cindy Aqeel William Raveis-New York LLC

  114 Lake Kitchawan Dr, South Salem, NY 10590
• 

  $583,000

  Sold Jun 09, 2026

  10 Guilford Cir, Goldens Bridge, NY 10526

  • 2 Beds
  • 2.5 Baths
  • 2,626 Sq Ft
  • Built 1994

  Last Sold Summary

  • 10% Below List Price
  • $222/SF
  • 115 Days On Market

  Current Estimated Value $603,205

  Last Listing Agent Debra DeMelis Coldwell Banker Realty

  10 Guilford Cir, Goldens Bridge, NY 10526
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  Not Listed For Sale

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

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft
  • Built 1971

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

  Last Sold Summary

  • 33 Days On Market

  Last Listing Agent Matthew Valvano Berkshire Hathaway HS NY Prop
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  /41

  $1,300,000

  Pending

  • 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
• 

  

  /22

  $2,850 Per Month

  • 1 Bed
  • 1 Bath
  • 1,020 Sq Ft
  • Condo for Rent

  277 Maplewood Dr Unit 32277, South Salem, NY 10590

  Experience the perfect blend of nature, privacy, and modern living in this beautifully renovated end unit, nestled against a tranquil wooded backdrop. Fully updated from the studs up, this move-in ready home features new flooring, windows, doors, utilities, and appliances, along with a sleek new kitchen and stylishly renovated bathroom. The open-concept kitchen flows seamlessly into the dining

  Michael Portnoy Giner Real Estate Inc.

  277 Maplewood Dr Unit 32277, South Salem, NY 10590
• 

  $875,000

  Sold Jul 24, 2026

  8 Debbie Ln Unit 6, Cross River, NY 10518

  • 3 Beds
  • 2.5 Baths
  • 2,132 Sq Ft
  • Built 1984

  Last Sold Summary

  • 12% Above List Price
  • $410/SF
  • 17 Days On Market

  Current Estimated Value $804,245

  Last Listing Agent Jessica Cunningham Houlihan Lawrence Inc.

  8 Debbie Ln Unit 6, Cross River, NY 10518
• 

  Est $306,988

  Not Listed For Sale

  74 Fox Run Unit 3-74, South Salem, NY 10590

  • 2 Beds
  • 1 Bath
  • 885 Sq Ft
  • Built 1981

  74 Fox Run Unit 3-74, South Salem, NY 10590

  Last Sold Summary

  • 66 Days On Market

  Last Listing Agent Ann Marie D'Onofrio Briante Realty Group, LLC
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  /36

  $1,150,000

  Pending

  • 3 Beds
  • 3 Baths
  • 2,487 Sq Ft

  336 Smith Ridge Rd, South Salem, NY 10590

  Through a gated entrance framed by stone pillars awaits one of South Salem's most enchanting hidden treasures. Circa 1802, this extraordinary residence has been thoughtfully restored and impeccably maintained, blending authentic period character with the comforts of modern living. Set on a level, manicured acre, the grounds are magical, with lush lawns, specimen trees, mature hemlocks,

  Michael Neeley William Raveis-New York LLC

  336 Smith Ridge Rd, South Salem, NY 10590
• 

  

  /35

  $5,500 Per Month

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

  9 S Shore Dr, South Salem, NY 10590

  Booked May 19, 2026 - October 20, 2026 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.

  Gina Cooney Giner Real Estate Inc.

  9 S Shore Dr, 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 $1,025,372

  Last Listing Agent Mary Anne Condon Ginnel Real Estate

  9 Upland Ct, South Salem, NY 10590
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  Not Listed For Sale

  17 & 19 Lakeview Rd, South Salem, NY 10590

  • 3 Beds
  • 1.5 Baths
  • 1,048 Sq Ft
  • Built 1925

  17 & 19 Lakeview Rd, South Salem, NY 10590

  Last Sold Summary

  • 49 Days On Market

  Last Listing Agent Gina Cooney Giner Real Estate Inc.

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