Lewisboro, NY Homes

• 

  

  

  /35

  $1,695,000

  Pending

  • 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 custom,

  Melissa Frank Lutz Douglas Elliman Real Estate

  32 Split Rock Rd, Pound Ridge, NY 10576
• 

  $1,137,000

  Sold Sep 15, 2025

  30 Benedict Rd, South Salem, NY 10590

  • 3 Beds
  • 2 Baths
  • 2,400 Sq Ft
  • Built 1960

  Last Sold Summary

  • 14% Above List Price
  • $474/SF
  • 35 Days On Market

  Current Estimated Value $1,139,678

  Last Listing Agent Margaret Harrington Douglas Elliman Real Estate

  30 Benedict Rd, South Salem, NY 10590
• 

  Est $305,818

  Not Listed For Sale

  58 Fox Run Unit 258, South Salem, NY 10590

  • 1 Bed
  • 1 Bath
  • 791 Sq Ft
  • Built 1981

  58 Fox Run Unit 258, South Salem, NY 10590

  Last Sold Summary

  • 30 Days On Market

  Last Listing Agent Michael Portnoy Giner Real Estate Inc.
• 

  

  

  /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
• 

  $872,000

  Sold Oct 23, 2025

  187 Todd Rd, Katonah, NY 10536

  • 3 Beds
  • 2 Baths
  • 1,851 Sq Ft
  • Built 1939

  Last Sold Summary

  • 21% Above List Price
  • $471/SF
  • 14 Days On Market

  Current Estimated Value $883,467

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

  187 Todd Rd, Katonah, NY 10536
• 

  Est $259,937

  Not Listed For Sale

  56 Fox Run, South Salem, NY 10590

  • 1 Bed
  • 1 Bath
  • 660 Sq Ft
  • Built 1980

  56 Fox Run, South Salem, NY 10590

  Last Sold Summary

  • 83 Days On Market

  Last Listing Agent DONNA LEWIS K. Fortuna Realty, Inc.
• 

  

  /16

  $1,875,000

  Coming Soon

  • 3 Beds
  • 2.5 Baths
  • 3,364 Sq Ft

  21 Twin Lakes Rd, South Salem, NY 10590

  Welcome to 21 Twin Lakes Road — a stunning, complete renovation that is as close to new construction as you'll find. Every detail has been thoughtfully reimagined, from the sun-filled open floor plan to the gorgeous authentic reclaimed beams that give the home instant character and warmth. A separate 1st floor bonus room and finished basement offers flexible space for a home office, playroom, or

  Juliska Martino Compass Greater NY, LLC

  21 Twin Lakes Rd, 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 $727,573

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

  15 Glen Dr, South Salem, NY 10590
• 

  Est $259,737

  Not Listed For Sale

  22 Fox Run, South Salem, NY 10590

  • 1 Bed
  • 1 Bath
  • 660 Sq Ft
  • Built 1981

  22 Fox Run, South Salem, NY 10590

  Last Sold Summary

  • 54 Days On Market

  Last Listing Agent Christine MacDonald Houlihan Lawrence Inc.
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  /32

  $1,695,000

  $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
• 

  $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 $2,524,980

  Last Listing Agent Lindsay Matthews Houlihan Lawrence Inc.

  241 N Salem Rd, Waccabuc, NY 10597
• 

  Est $597,689

  Not Listed For Sale

  39 Bittersweet Ln, South Salem, NY 10590

  • 3 Beds
  • 2 Baths
  • 1,883 Sq Ft
  • Built 1981

  39 Bittersweet Ln, South Salem, NY 10590

  Last Sold Summary

  • 32 Days On Market

  Last Listing Agent Brenda Timm Coldwell Banker Realty
• 

  

  /34

  $725,000

  Pending

  • 3 Beds
  • 1 Bath
  • 1,188 Sq Ft

  21 Elmwood Rd, South Salem, NY 10590

  Welcome to Pepper Ridge Farm! 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

  Debi Orr Keller Williams Prestige Prop

  21 Elmwood 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 $760,647

  Last Listing Agent Mark Boyland Keller Williams Realty Partner

  25 Twin Lakes Rd, South Salem, NY 10590
• 

  Est $958,424

  Not Listed For Sale

  38 Lockwood Rd, South Salem, NY 10590

  • 3 Beds
  • 3.5 Baths
  • 2,478 Sq Ft
  • Built 1977

  38 Lockwood Rd, South Salem, NY 10590

  Last Sold Summary

  • 30 Days On Market

  Last Listing Agent Geraldine Brucale BHHS Hudson Valley Properties
• 

  

  /28

  $2,295,000

  Open Sun 12PM - 2PM $100K PRICE DROP

  • 3 Beds
  • 4.5 Baths
  • 2,812 Sq Ft

  137 Boway Rd, South Salem, NY 10590

  Gracious Country Colonial! Originally built in 1932 and thoughtfully renovated, this timeless antique Colonial seamlessly blends historic character with modern updates. Offering approximately 2,800 square feet of beautifully appointed living space, the home features hardwood floors, period millwork, abundant natural light, French doors, and nicely proportioned rooms throughout. Former owner Liz

  Cheryl Neuburger Ginnel Real Estate

  137 Boway Rd, South Salem, NY 10590
• 

  $35,000

  Sold Jul 21, 2026

  0 Cove Rd Unit KEY993296, Lewisboro, NY 10590

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

  Last Sold Summary

  • 18 Days On Market

  Last Listing Agent Anne-Marie Nordgren Coldwell Banker Realty

  0 Cove Rd Unit KEY993296, Lewisboro, NY 10590
• 

  Est $955,662

  Not Listed For Sale

  235 Elmwood Rd, South Salem, NY 10590

  • 4 Beds
  • 2.5 Baths
  • 2,592 Sq Ft
  • Built 1975

  235 Elmwood Rd, South Salem, NY 10590

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Joann Galluccio William Raveis-New York LLC
• 

  

  /27

  $1,595,000

  • 3 Beds
  • 3.5 Baths
  • 3,665 Sq Ft

  78 Old Church Ln, Pound Ridge, NY 10576

  Nestled on one of South Salem's most picturesque country lanes, 78 Old Church Lane offers a beautiful blend of privacy, comfort, and timeless style. Set on 4.6 magical, level acres surrounded by classic architecture and rolling countryside, this beautifully maintained residence is move-in-ready and designed for effortless living. Completely renovated in 2004, the home features sun-filled

  Jody Rosen Julia B Fee Sothebys Int. Rlty

  78 Old Church Ln, Pound Ridge, NY 10576
• 

  $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 $1,294,357

  Last Listing Agent Lindsay Lafreniere William Raveis-New York LLC

  9 Ashwood Rd, South Salem, NY 10590
• 

  Est $843,103

  Not Listed For Sale

  11 Lorraine Rd, South Salem, NY 10590

  • 3 Beds
  • 2 Baths
  • 1,332 Sq Ft
  • Built 1970

  11 Lorraine Rd, South Salem, NY 10590

  Last Sold Summary

  • 15 Days On Market

  Last Listing Agent Mark Boyland Keller Williams Realty Partner
• 

  

  /23

  $375,000

  $50K PRICE DROP Pending

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft

  14 W Main St, Goldens Bridge, NY 10526

  Unique opportunity to own a 3-bedroom, 2-bath home offering flexibility and future possibilities in the Goldens Bridge Lake Community, also known as The Colony. Property presents an opportunity for significant improvement or possibly new construction. One of the home's most exciting features is the approximately 480 sq. ft. walk-up attic, a truly unique space with endless potential. Whether

  Mark Boyland Keller Williams Realty Partner

  14 W Main St, Goldens Bridge, NY 10526
• 

  $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 $822,442

  Last Listing Agent Erin Lee Keller Williams Realty Group

  256 Smith Ridge Rd, South Salem, NY 10590
• 

  Est $1,230,586

  Not Listed For Sale

  3 Scenic Dr, South Salem, NY 10590

  • 4 Beds
  • 3.5 Baths
  • 3,079 Sq Ft
  • Built 1986

  3 Scenic Dr, South Salem, NY 10590

  Last Sold Summary

  • 24 Days On Market

  Last Listing Agent Michael Vasquez eXp Realty
• 

  

  /22

  $809,900

  $90K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,189 Sq Ft

  98 Smith Ridge Rd, South Salem, NY 10590

  Beautifully updated and move-in ready, this 4-bedroom home is set on 2 private acres in the highly desirable Katonah-Lewisboro School District. Thoughtfully renovated throughout, the home features refinished hardwood floors, fresh neutral interiors, brand-new stainless steel appliances, 2 full bathrooms, and an updated powder room.The light-filled open layout offers comfortable everyday

  Sari Shaw Compass Greater NY, LLC

  98 Smith Ridge Rd, 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 $416,229

  Last Listing Agent Lindsay Lafreniere William Raveis-New York LLC

  144 Stone Meadow, South Salem, NY 10590
• 

  Est $785,455

  Not Listed For Sale

  464 Smith Ridge Rd, South Salem, NY 10590

  • 4 Beds
  • 3 Baths
  • 3,371 Sq Ft
  • Built 1900

  464 Smith Ridge Rd, South Salem, NY 10590

  Last Sold Summary

  • 68 Days On Market

  Last Listing Agent Hua Bin Chen Liberty Chateau Realty Inc
• 

  

  /22

  $649,000

  $30K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,872 Sq Ft

  9 Stewart Rd, South Salem, NY 10590

  This lake community home has deeded access to Truesdale Lake and is located in the award-winning Katonah-Lewisboro School District. Located on a quiet cul-de-sac, this expanded cape cod-style home has good bones and great potential. Upon entering, a fireplace warms the front parlor and living room. Beyond, the kitchen opens to a dining room and an expanded family room with a stone fireplace, home

  Larry Mango Giner Real Estate Inc.

  9 Stewart Rd, South Salem, NY 10590
• 

  $900,000

  Sold Aug 07, 2026

  5 Primrose St, Katonah, NY 10536

  • 3 Beds
  • 2 Baths
  • 2,467 Sq Ft
  • Built 1945

  Last Sold Summary

  • 5% Above List Price
  • $365/SF
  • 17 Days On Market

  Current Estimated Value $871,271

  Last Listing Agent Christine Trudeau Keller Williams Prestige Prop

  5 Primrose St, Katonah, NY 10536
• 

  Est $1,112,240

  Not Listed For Sale

  42 West Rd, South Salem, NY 10590

  • 3 Beds
  • 3 Baths
  • 2,656 Sq Ft
  • Built 1948

  42 West Rd, South Salem, NY 10590

  Last Sold Summary

  • 21 Days On Market

  Last Listing Agent Lawler Parker Douglas Elliman Real Estate
• 

  

  /45

  $1,695,000

  $54K PRICE DROP

  • 5 Beds
  • 6 Baths
  • 4,952 Sq Ft

  Unlisted Address

  Architecturally distinctive and beautifully connected to its natural surroundings, this custom cedar contemporary offers a refreshing alternative to the traditional colonial. Set on over 4 private acres in the heart of South Salem, the home blends dramatic volume, natural light, privacy, and flexible living spaces designed for modern living. The home’s layout flows easily from one inviting space

  Danielle Raguzin Re-Max Experience

  Unlisted Address
• 

  $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 $1,450,120

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

  230 Spring St, South Salem, NY 10590
• 

  Est $541,460

  Not Listed For Sale

  28 West Rd, South Salem, NY 10590

  • 2 Beds
  • 1 Bath
  • 1,176 Sq Ft
  • Built 1921

  28 West Rd, South Salem, NY 10590

  Last Sold Summary

  • 20 Days On Market

  Last Listing Agent Giancarlo Pecora eXp Realty
• 

  

  /24

  $650,000

  Pending

  • 3 Beds
  • 2 Baths
  • 2,206 Sq Ft

  33 Sabbath Day Hill Rd, South Salem, NY 10590

  Perfect as a year-round residence or a private weekend retreat, this charming home offers comfortable living in a super convenient location. It sits on a quiet country road surrounded by nature, yet it is close to the highway (7 miles to I-684); train (8 miles to Katonah MTA Metro North station with direct trains to Grand Central), schools, and other everyday conveniences. This well-loved home

  Natasha Pazdzerskaia Coldwell Banker Realty

  33 Sabbath Day Hill Rd, South Salem, NY 10590
• 

  $1,325,000

  Sold Oct 16, 2025

  21 Lake Shore Dr, South Salem, NY 10590

  • 2 Beds
  • 3 Baths
  • 1,940 Sq Ft
  • Built 2020

  Last Sold Summary

  • 8% Above List Price
  • $683/SF
  • 8 Days On Market

  Current Estimated Value $1,360,383

  Last Listing Agent Melissa Marcogliese Compass Greater NY, LLC

  21 Lake Shore Dr, South Salem, NY 10590
• 

  Est $729,227

  Not Listed For Sale

  35 West Rd, South Salem, NY 10590

  • 3 Beds
  • 2.5 Baths
  • 2,052 Sq Ft
  • Built 1979

  35 West Rd, South Salem, NY 10590

  Last Sold Summary

  • 16 Days On Market

  Last Listing Agent Carol Court Howard Hanna Rand Realty
• 

  

  /14

  $1,150,000

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

  42 Gilbert St, South Salem, NY 10590

  A special opportunity to own a piece of Westchester's sought after private lake communities! Beautifully sited on 83 acre Lake Truesdale. It has a large deck and dock overlooking the water, along with a private driveway. This 1930 antique colonial is full of character - beamed ceilings, a fireplace and glass doors opening to a deck built for lakeside living. The spacious living room with

  Barbara Tremain Houlihan Lawrence Inc.

  42 Gilbert St, South Salem, NY 10590
• 

  $1,685,000

  Sold May 28, 2026

  9 Comanche Ct, Katonah, NY 10536

  • 4 Beds
  • 3.5 Baths
  • 4,256 Sq Ft
  • Built 1982

  Last Sold Summary

  • 21% Above List Price
  • $396/SF
  • 10 Days On Market

  Current Estimated Value $1,602,761

  Last Listing Agent Wendy Loring William Raveis-New York LLC

  9 Comanche Ct, Katonah, NY 10536
• 

  Est $1,205,442

  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

  Last Listing Agent Luke Joachim Redfin Real Estate
• 

  

  /32

  $950,000

  $49K PRICE DROP Pending

  • 4 Beds
  • 2.5 Baths
  • 2,700 Sq Ft

  10 Silvermine Dr, South Salem, NY 10590

  THE ONE YOU HAVE BEEN WAITING FOR! Move-in ready and surrounded by nature, this beautifully updated Colonial is tucked away on a quiet cul-de-sac. Enjoy a peaceful setting that's ideal for morning coffee on the deck, scenic dog walks, and neighborhood bike rides, while still offering a highly convenient location close to shopping, schools, parks, and commuting routes.From the moment you

  Larry Mango Giner Real Estate Inc.

  10 Silvermine Dr, South Salem, NY 10590

Showing Results 121 - 160, Page 4 of 18