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Windham town, NY - single-family homes for sale
72 of 72 results displayed
- New
$289,900Active2 beds 1 baths800 sq. ft.107 Route 40 Road, Windham, NY 12496
MLS# 20260694Listed by: RHR REALTY GROUP - New
$675,000Active3 beds 2 baths2,350 sq. ft.5287 Route 23, Windham, NY 12496
MLS# 20260653Listed by: COMPASS GREATER NEW YORK, LLC 
$599,000Active3 beds 2 baths2,250 sq. ft.16 Hickory Hill Road, Windham, NY 12496
MLS# 20260578Listed by: SHAW COUNTRY REALTY, INC.
$1,300,000Active5 beds 3 baths2,834 sq. ft.42 N Ridge Extension, Windham, NY 12496
MLS# 20260530Listed by: COLDWELL BANKER VILLAGE GREENW
$1,345,000Active4 beds 4 baths2,856 sq. ft.2 Watch Hill Lane #2, Windham, NY 12496
MLS# 20260488Listed by: BRAINARD RIDGE MANAGEMENT- Open Sat, 2 to 4pm
$1,200,000Active3 beds 2 baths2,170 sq. ft.206 Siam Road, Windham, NY 12496
MLS# 20260444Listed by: COMPASS GREATER NEW YORK, LLC - Open Sat, 12:30 to 2pm
$1,775,000Active5 beds 5 baths3,218 sq. ft.31 Windham Farms Road, Windham, NY 12496
MLS# 957893Listed by: FOUR SEASONS SOTHEBYS INTL 
$152,000Active-- beds 1 baths560 sq. ft.7 Quads Way, Windham, NY 12496
MLS# 957003Listed by: RE/MAX TOWN & COUNTRY
$2,750,000Active6 beds 5 baths4,730 sq. ft.208 Mill Street, Windham, NY 12496
MLS# 953759Listed by: ICONIC PROS
$695,000Active3 beds 2 baths1,448 sq. ft.730 Mill Street, Windham, NY 12496
MLS# 20260344Listed by: BRAINARD RIDGE MANAGEMENT- Open Sun, 12:30 to 2pm
$1,375,000Active4 beds 4 baths4,280 sq. ft.305 Mitchell Hollow Road, Windham, NY 12496
MLS# 951166Listed by: FOUR SEASONS SOTHEBYS INTL 
$1,750,000Active5 beds 4 baths4,056 sq. ft.5433 Ny-23, Windham, NY 12496
MLS# 20260285Listed by: COMPASS GREATER NY, LLC
$525,000Active3 beds 2 baths2,084 sq. ft.34 Old Road, Windham, NY 12496
MLS# 952926Listed by: PATRICIA FORGIONE'S REALTY
$499,000Active3 beds 3 baths1,566 sq. ft.13 Brainard Ridge Road, Windham, NY 12496
MLS# 20260225Listed by: COLDWELL BANKER VILLAGE GREENW
$349,000Active3 beds 2 baths1,152 sq. ft.315 Begley Road, Windham, NY 12496
MLS# 20260215Listed by: SHAW COUNTRY REALTY, INC.
$550,000Active2 beds 1 baths1,122 sq. ft.183 South Street, Windham, NY 12496
MLS# 20260193Listed by: SHAW COUNTRY REALTY, INC.
$780,000Active4 beds 3 baths1,839 sq. ft.91 Beaver Hill Road, Windham, NY 12496
MLS# 20260174Listed by: BRAINARD RIDGE MANAGEMENT
$1,650,000Active4 beds 4 baths2,770 sq. ft.10 Stonewall Lane, Windham, NY 12496
MLS# 948997Listed by: DOUGLAS ELLIMAN REAL ESTATE
$1,900,000Active5 beds 5 baths3,150 sq. ft.19 Stonewall Lane, Windham, NY 12496
MLS# 949825Listed by: DOUGLAS ELLIMAN REAL ESTATE
$685,000Active5 beds 3 baths3,184 sq. ft.523 Mitchell Hollow Road, Windham, NY 12496
MLS# 20256169Listed by: SHAW COUNTRY REALTY, INC.
$790,000Pending3 beds 4 baths2,324 sq. ft.78 Mitchell Hollow Road, Windham, NY 12496
MLS# 20256152Listed by: COLDWELL BANKER VILLAGE GREENW
$2,250,000Active5 beds 5 baths3,600 sq. ft.90 Club Road, Windham, NY 12496
MLS# 20256151Listed by: BUNCE REALTY
$2,500,000Active7 beds 6 baths5,569 sq. ft.110 Old Road, Windham, NY 12496
MLS# 20256123Listed by: COLDWELL BANKER VILLAGE GREENW
$3,600,000Active6 beds 5 baths5,000 sq. ft.209 Club Road, Windham, NY 12496
MLS# 20256011Listed by: BRAINARD RIDGE MANAGEMENT
$499,000Active3 beds 3 baths1,903 sq. ft.215 Siam Road, Windham, NY 12496
MLS# 20255960Listed by: COLDWELL BANKER VILLAGE GREENW
$1,175,000Active5 beds 3 baths4,489 sq. ft.32 Glennamaddy Drive, Windham, NY 12496
MLS# 20255834Listed by: CONTINENTAL REAL ESTATE GROUP
$699,000Active2 beds 2 baths1,438 sq. ft.355 South Street, Windham, NY 12496
MLS# 20255740Listed by: BRAINARD RIDGE MANAGEMENT
$1,899,000Active5 beds 4 baths4,044 sq. ft.22 The Loop, Windham, NY 12496
MLS# 20255691Listed by: COLDWELL BANKER VILLAGE GREENW
$985,000Active5 beds 5 baths4,500 sq. ft.5355 Ny-212, Shandaken, NY 12480
MLS# 202529002Listed by: PRIME LISTINGS, INC
$1,175,000Pending12 beds 4 baths3,284 sq. ft.20 Brook Hollow Lane, Windham, NY 12496
MLS# 921643Listed by: FOUR SEASONS SOTHEBYS INTL
$2,175,000Active6 beds 4 baths4,104 sq. ft.19 Twin Maples Lane, Windham, NY 12496
MLS# 20255113Listed by: COLDWELL BANKER VILLAGE GREENW
$2,799,000Active6 beds 6 baths5,872 sq. ft.81 Sundance Drive, Windham, NY 12496
MLS# 20255018Listed by: COLDWELL BANKER VILLAGE GREENW
$399,000Pending5 beds 3 baths2,472 sq. ft.317 Mitchell Hollow Road, Windham, NY 12496
MLS# 20254983Listed by: COLDWELL BANKER VILLAGE GREENW
$715,000Active4 beds 2 baths2,240 sq. ft.60 County Route 65 A, Windham, NY 12496
MLS# 20254949Listed by: COLDWELL BANKER VILLAGE GREENW
$479,000Active4 beds 2 baths1,368 sq. ft.7 Karlstadt Road, Windham, NY 12496
MLS# 20254931Listed by: COLDWELL BANKER VILLAGE GREENW
$625,000Active4 beds 4 baths2,100 sq. ft.57 Brainard Ridge #3-E, Windham, NY 12496
MLS# 20254919Listed by: COLDWELL BANKER VILLAGE GREENW
$1,125,000Active5 beds 6 baths3,643 sq. ft.292 #3 South Street, Windham, NY 12496
MLS# 20254832Listed by: COLDWELL BANKER VILLAGE GREENW
$2,495,000Active8 beds 4 baths3,350 sq. ft.3 Leon Macglashan Road, Windham, NY 12496
MLS# 912042Listed by: SERHANT LLC
$749,000Active4 beds 4 baths2,088 sq. ft.93 Maplewood Road, Windham, NY 12496
MLS# 20254677Listed by: COLDWELL BANKER VILLAGE GREENW
$399,000Pending3 beds 2 baths1,876 sq. ft.370 Begley Road, Windham, NY 12496
MLS# 20254656Listed by: COLDWELL BANKER VILLAGE GREENW
$199,000Active-- beds -- baths611 Mitchell Hollow Road, Windham, NY 12496
MLS# 20254648Listed by: COLDWELL BANKER VILLAGE GREENW
$799,000Active3 beds 4 baths3,729 sq. ft.415 Old Road, Windham, NY 12496
MLS# 20254472Listed by: HUNTER WINDHAM REAL ESTATE
$399,000Active3 beds 2 baths1,400 sq. ft.436 Big Hollow Road, Windham, NY 12496
MLS# 20254344Listed by: SHAW COUNTRY REALTY, INC.
$500,000Pending3 beds 2 baths1,140 sq. ft.38 Cambridge Heights Road, Windham, NY 12496
MLS# 20254210Listed by: ANATOLE HOUSE LLC
$1,295,000Active4 beds 4 baths2,900 sq. ft.129 Club Road, Windham, NY 12496
MLS# 20254026Listed by: BRAINARD RIDGE MANAGEMENT
$849,000Pending3 beds 3 baths2,864 sq. ft.407 Mill Street, Windham, NY 12496
MLS# 202524673Listed by: HOULIHAN LAWRENCE
$1,299,000Active5 beds 6 baths3,752 sq. ft.7 Meadow Lane, Windham, NY 12496
MLS# 20253813Listed by: COMPASS GREATER NY, LLC
$1,450,000Active6 beds 6 baths4,284 sq. ft.93 & 99 Nauvoo Road, Windham, NY 12496
MLS# 20253703Listed by: COLDWELL BANKER VILLAGE GREENW
$1,999,000Active4 beds 4 baths4,247 sq. ft.37 White Way, Windham, NY 12496
MLS# 20253702Listed by: BUNCE REALTY
$3,250,000Active6 beds 5 baths5,005 sq. ft.219 Club Road, Windham, NY 12496
MLS# 20253358Listed by: COLDWELL BANKER VILLAGE GREENW
$565,000Active4 beds 2 baths1,052 sq. ft.31 Koonan Road, Windham, NY 12496
MLS# 20253265Listed by: CORE REAL ESTATE TEAM
$850,000Active8 beds 8 baths3,712 sq. ft.5320 Route 23, Windham, NY 12496
MLS# 20252750Listed by: SHAW COUNTRY REALTY, INC.
$334,900Active2 beds 2 baths1,040 sq. ft.504 Rt. 40, Windham, NY 12496
MLS# 20252589Listed by: SHAW COUNTRY REALTY, INC.
$449,000Active4 beds 2 baths2,457 sq. ft.20 Slater Road, Windham, NY 12496
MLS# 20252531Listed by: RHR REALTY GROUP
$499,000Active4 beds 3 baths2,287 sq. ft.18 Maplewood Avenue, Windham, NY 12496
MLS# 20252508Listed by: BUNCE REALTY
$759,000Active4 beds 4 baths2,100 sq. ft.769 Mitchell Hollow Road, Windham, NY 12496
MLS# 20252216Listed by: COLDWELL BANKER VILLAGE GREENW
$1,899,000Active5 beds 5 baths3,723 sq. ft.4 Goff Road, Windham, NY 12496
MLS# 20251987Listed by: COLDWELL BANKER VILLAGE GREENW
$294,000Active2 beds 2 baths1,290 sq. ft.71 County Road 65 #6, Windham, NY 12439
MLS# 925738Listed by: COMPASS GREATER NY, LLC
$1,949,000Active5 beds 3 baths3,893 sq. ft.33 Elm Ridge Road, Windham, NY 12496
MLS# 142580Listed by: COLDWELL BANKER VILLAGE GREENW
$999,000Pending7 beds 3 baths4,281 sq. ft.5474 Route 23, Windham, NY 12496
MLS# 149640Listed by: JANE H. REYNOLDS
$650,000Active4 beds 2 baths1,440 sq. ft.85 Cambridge Heights Rd., Windham, NY 12496
MLS# 156043Listed by: COLDWELL BANKER VILLAGE GREENW
$1,950,000Active5 beds 4 baths4,834 sq. ft.77 Beaver Hill Road, Windham, NY 12496
MLS# 156103Listed by: COLDWELL BANKER VILLAGE GREENW
$1,149,000Active5 beds 6 baths3,460 sq. ft.292 South Street #2, Windham, NY 12496
MLS# 156125Listed by: COLDWELL BANKER VILLAGE GREENW
$2,250,000Pending9 beds 7 baths6,859 sq. ft.150 Trailside Road, Windham, NY 12496
MLS# 156438Listed by: COLDWELL BANKER VILLAGE GREENW
$449,000Active4 beds 4 baths2,950 sq. ft.25 Vets Road, Windham, NY 12496
MLS# 156676Listed by: COLDWELL BANKER VILLAGE GREENW
$1,649,000Active5 beds 4 baths4,312 sq. ft.102 Thunderbird Terrace, Windham, NY 12496
MLS# 156747Listed by: COLDWELL BANKER VILLAGE GREENW
$389,000Active3 beds 2 baths1,464 sq. ft.110 - 2 High Ridge Road, Windham, NY 12496
MLS# 156888Listed by: BUNCE REALTY
$485,000Active3 beds 1 baths1,200 sq. ft.5134 Route 23, Windham, NY 12496
MLS# 20254112Listed by: DUGO REALTY
$439,000Pending4 beds 3 baths1,914 sq. ft.17 Mitchell Hollow Road, Windham, NY 12496
MLS# 20255650Listed by: BUNCE REALTY
$1,998,500Active5 beds 6 baths5,000 sq. ft.4 Estate View Drive, Windham, NY 12496
MLS# 202519775Listed by: KW PLATFORM
$1,400,000Active3 beds 4 baths2,400 sq. ft.17 Stonewall Lane, Windham, NY 12496
MLS# 948963Listed by: DOUGLAS ELLIMAN REAL ESTATE
$2,100,000Active4 beds 4 baths3,400 sq. ft.22 Club Road, Windham, NY 12496
MLS# 20252877Listed by: BRAINARD RIDGE MANAGEMENT
Local realty services provided by:CENTURY 21 Hudson Valley Realty, CENTURY 21 Monticello Realty, CENTURY 21 North East
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©2026 Century 21 Real Estate LLC. All rights reserved. CENTURY 21®, the CENTURY 21 Logo and C21® are service marks owned by Century 21 Real Estate LLC. Century 21 Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each office is independently owned and operated. Listing information is deemed reliable but not guaranteed accurate.
Protect your home and budget from life's surprises with an Assurant Home Warranty, backed by a partner that supports you through every step of homeownership. Explore Plans.
©2026 Century 21 Real Estate LLC. All rights reserved. CENTURY 21®, the CENTURY 21 Logo and C21® are service marks owned by Century 21 Real Estate LLC. Century 21 Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each office is independently owned and operated. Listing information is deemed reliable but not guaranteed accurate.