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Lewisboro

Luxury listings for sale in Lewisboro

18 of 18 Homes
COMPARE
NEW

$7,900,000

422 Mt Holly Rd, Katonah, NY

6 br3 BA, 1 HALF BA5,053 sf

Listing Courtesy of HOULIHAN LAWRENCE INC.., LINDSAY J. MATTHEWS - 914-318-1394

PRICE REDUCED

$4,395,000

45 Pine Hill Dr, South Salem, NY

4 br4 BA, 1 HALF BA6,161 sf

Listing Courtesy of COMPASS GREATER NY, LLC., JOSEPH LUKIC - 914-334-3805

$3,500,000

390 Smith Ridge Rd, South Salem, NY

3,078 sf

Listing Courtesy of WILLIAM RAVEIS REAL ESTATE., GIUSEPPE MELILLO - 914-329-7325

NEW

$2,995,000

54 Cross Pond Rd, Pound Ridge, NY

4 br4 BA, 1 HALF BA5,386 sf

Listing Courtesy of COMPASS GREATER NY, LLC., ADAM HADE - 914-804-1754

$2,850,000

Lot 13 Sachem Way, South Salem, NY

4 br3 BA, 1 HALF BA4,900 sf

Listing Courtesy of WILLIAM RAVEIS-NEW YORK LLC., MICHAEL NEELEY

PRICE REDUCED

$2,500,000

127 Boutonville Rd, Pound Ridge, NY

4 br4 BA, 1 HALF BA5,575 sf

Listing Courtesy of SERHANT LLC., SAMUEL BEREK - 917-239-7018

$2,499,000

355 Smith Ridge Rd, South Salem, NY

4,500 sf

Listing Courtesy of COLDWELL BANKER REALTY., JUSTIN PIERAGOSTINI - 914-447-3396

Contract signed

$2,250,000

28 Twin Lakes Rd, South Salem, NY

4 br4 BA3,220 sf

Listing Courtesy of HOULIHAN LAWRENCE INC.., ANGELA KESSEL - 914-841-1919

$2,250,000

Lot 6 Sachem Way, South Salem, NY

4 br3 BA, 1 HALF BA3,000 sf

Listing Courtesy of WILLIAM RAVEIS-NEW YORK LLC., MICHAEL NEELEY

Contract signed

$1,999,000

6 Briscoe Rd, South Salem, NY

3 br3 BA, 2 HALF BA4,482 sf

Listing Courtesy of WILLIAM RAVEIS-NEW YORK LLC., MICHAEL NEELEY

Open house

$1,999,000

137 Boway Rd, South Salem, NY

3 br4 BA, 1 HALF BA2,812 sf

Listing Courtesy of GINNEL REAL ESTATE., CHERYL NEUBURGER - 914-707-8577

Contract signed

$1,900,000

3 Old Shop Rd, Cross River, NY

6 br3 BA, 2 HALF BA3,706 sf

Listing Courtesy of JULIA B FEE SOTHEBYS INT. RLTY., JODY ROSEN - 914-907-3300

$1,899,000

292 Smith Ridge Rd, South Salem, NY

4 br4 BA, 1 HALF BA5,666 sf

Listing Courtesy of WILLIAM RAVEIS-NEW YORK LLC., MICHAEL NEELEY

$1,795,000

30 Pine Hill Dr, South Salem, NY

4 br4 BA, 2 HALF BA5,288 sf
Virtual tour

Listing Courtesy of WILLIAM RAVEIS-NEW YORK LLC., NICHOLA MCMANN - 917-349-4763

Contract signed

$1,750,000

33 Truesdale Lake Dr, South Salem, NY

4 br3 BA, 1 HALF BA3,778 sf

Listing Courtesy of ISLAND ADVANTAGE REALTY LLC., TODD A. YOVINO - 631-351-6000

PRICE REDUCED

$1,695,000

37 West Ln, South Salem, NY

5 br6 BA4,952 sf
Virtual tour

Listing Courtesy of RE-MAX EXPERIENCE., DANIELLE RAGUZIN - 845-705-7530

$1,695,000

37 West Ln, Lewisboro, NY

5 br6 BA4,952 sf
Virtual tour

Listing Courtesy of RE/MAX EXPERIENCE, LLC., DANIELLE RAGUZIN - 845-705-7530, Office Contact - 203-775-2200

Open house

$1,650,000

31 Dingee Rd, South Salem, NY

4 br3 BA, 1 HALF BA4,000 sf

Listing Courtesy of HOULIHAN LAWRENCE INC.., TERESA CHANG - 914-907-0881

The data relating to real estate for sale on this web site comes in part from the OneKey® MLS. All information deemed reliable but not guaranteed and should be independently verified. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) nor the website owner shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Property locations as displayed on any map are best approximations only and exact locations should be independently verified. IDX information is provided exclusively for consumers personal non-commercial use and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

©2026 OneKey® MLS. All rights reserved.

LAST UPDATE DATE On OCT 14 2026 AT 11:58 PM COORDINATED UNIVERSAL TIME (UTC).

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed.

Copyright 2026 SmartMLS, Inc.

LAST UPDATE DATE On OCT 14 2026 AT 11:58 PM COORDINATED UNIVERSAL TIME (UTC).