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Windham, NY - homes for sale
67 of 67 results displayed
- New
$2,750,000Active6 beds 5 baths4,730 sq. ft.208 Mill Street, Windham, NY 12496
MLS# 953759Listed by: ICONIC PROS - Open Sat, 12:30 to 2:30pmNew
$1,375,000Active4 beds 4 baths4,280 sq. ft.305 Mitchell Hollow Road, Windham, NY 12496
MLS# 951166Listed by: FOUR SEASONS SOTHEBYS INTL - New
$799,000Active3 beds 3 baths1,528 sq. ft.71 Windham Mount Village #71, Windham, NY 12496
MLS# 20260313Listed by: SHAW COUNTRY REALTY, INC. - Open Sat, 1 to 3pmNew
$1,750,000Active5 beds 3 baths4,056 sq. ft.5433 Ny-23, Windham, NY 12496
MLS# 20260285Listed by: COMPASS GREATER NY, LLC 
$1,350,000Active4 beds 4 baths1,856 sq. ft.11 Whisper Creek Drive #504, Windham, NY 12496
MLS# 20260229Listed by: COLDWELL BANKER VILLAGE GREENW
$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.
$1,800,000Active4 beds 4 baths2,030 sq. ft.11 Whisper Creek Drive #503, Windham, NY 12496
MLS# 20260207Listed by: BRAINARD RIDGE MANAGEMENT
$649,000Active3 beds 3 baths1,528 sq. ft.24 Windham Mount Village #24, Windham, NY 12496
MLS# 20260208Listed by: BRAINARD RIDGE MANAGEMENT
$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
$790,000Active3 beds 4 baths2,324 sq. ft.78 Mitchell Hollow Road, Windham, NY 12496
MLS# 20256152Listed by: COLDWELL BANKER VILLAGE GREENW
$285,000Active2 beds 3 baths1,411 sq. ft.76 Loo Bridge Lane #12 B, Windham, NY 12496
MLS# 20256109Listed by: COLDWELL BANKER VILLAGE GREENW
$575,000Active3 beds 3 baths1,082 sq. ft.108 Brainard Ridge Road #14b, Windham, NY 12496
MLS# 20256102Listed by: BRAINARD RIDGE MANAGEMENT
$3,600,000Active6 beds 5 baths5,000 sq. ft.209 Club Road, Windham, NY 12496
MLS# 20256011Listed by: BRAINARD RIDGE MANAGEMENT
$99,000Active0.5 Acres448-1 South Street, Windham, NY 12496
MLS# 20255937Listed by: SHAW COUNTRY REALTY, INC.
$99,000Active0.5 Acres448-2 South Street, Windham, NY 12496
MLS# 20255938Listed by: SHAW COUNTRY REALTY, INC.
$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
$985,000Active5 beds 5 baths4,500 sq. ft.5355 Ny-212, Shandaken, NY 12480
MLS# 202529002Listed by: PRIME LISTINGS, INC
$463,000Active3 beds 2 baths1,249 sq. ft.111 Brainard Ridge Road #11b, Windham, NY 12496
MLS# 20255439Listed by: BRAINARD RIDGE MANAGEMENT
$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
$170,000Active1 beds 1 baths423 sq. ft.5220 Route 23 #126, Windham, NY 12496
MLS# 20254944Listed by: WEICHERT REALTORS FONTAINE
$625,000Active4 beds 4 baths2,100 sq. ft.57 Brainard Ridge #3-E, Windham, NY 12496
MLS# 20254919Listed by: COLDWELL BANKER VILLAGE GREENW
$639,000Pending4 beds 2 baths2,240 sq. ft.19 Brook Hollow Lane, Windham, NY 12496
MLS# 20254907Listed by: SHAW COUNTRY REALTY, INC.
$1,749,999Pending6 beds 5 baths4,855 sq. ft.12 Lauren Lane, Windham, NY 12496
MLS# 20254897Listed 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
$399,000Active0.46 Acres2 Twin Maples Lane, Windham, NY 12496
MLS# 20254820Listed by: COLDWELL BANKER VILLAGE GREENW
$1,499,000Pending4 beds 5 baths2,893 sq. ft.3 Enclave East Drive, Windham, NY 12496
MLS# 20254690Listed by: COLDWELL BANKER VILLAGE GREENW
$749,000Active4 beds 4 baths2,088 sq. ft.93 Maplewood Road, Windham, NY 12496
MLS# 20254677Listed by: COLDWELL BANKER VILLAGE GREENW
$253,000Active0.59 Acres57 South Street, Windham, NY 12496
MLS# 20254628Listed by: LISTWITHFREEDOM.COM
$275,000Active0.32 Acres0 Twin Maples Lane, Windham, NY 12496
MLS# 20254325Listed by: BRAINARD RIDGE MANAGEMENT
$319,000Active2 beds 3 baths1,178 sq. ft.63 Windham Ridge Road, Windham, NY 12496
MLS# 20254311Listed by: SHAW COUNTRY REALTY, INC.
$849,000Active3 beds 3 baths2,864 sq. ft.407 Mill Street, Windham, NY 12496
MLS# 905200Listed by: HOULIHAN LAWRENCE, INC
$289,999Active2 beds 2 baths1,163 sq. ft.5359 Ny-23, Windham, NY 12496
MLS# 202524212Listed by: NEWCOMB REALTY GROUP LLC
$1,450,000Active6 beds 6 baths4,284 sq. ft.93 & 99 Nauvoo Road, Windham, NY 12496
MLS# 20253703Listed by: COLDWELL BANKER VILLAGE GREENW
$449,999Active2 beds 3 baths2,026 sq. ft.61 South Street, Windham, NY 12496
MLS# 900170Listed by: SCHATZ REALTY GROUP
$599,000Active1.23 Acres137-1 South Street, Windham, NY 12496
MLS# 20253609Listed by: COLDWELL BANKER VILLAGE GREENW
$269,000Pending2 beds 3 baths1,211 sq. ft.79 Windham Ridge Road #17A, Windham, NY 12496
MLS# 898832Listed by: REAL BROKER NY LLC
$329,999Pending2 beds 3 baths1,058 sq. ft.73 Windham Ridge Road #16h, Windham, NY 12496
MLS# 20253447Listed by: COLDWELL BANKER VILLAGE GREENW
$259,000Active2 beds 2 baths1,024 sq. ft.113 Windham Ridge Road, Windham, NY 12496
MLS# 20253303Listed by: BERKSHIRE HATHAWAY HOMESERVICE
$590,000Active4 beds 2 baths1,052 sq. ft.31 Koonan Road, Windham, NY 12496
MLS# 20253265Listed by: CORE REAL ESTATE TEAM
$899,900Active6.17 AcresTBD Boulder Brook Lots 33-38 Road, Windham, NY 12496
MLS# 878815Listed by: HOWARD HANNA RAND REALTY
$1,589,000Active3 beds 3 baths1,655 sq. ft.10 Enclave North Drive #106, Windham, NY 12496
MLS# 20252962Listed by: BRAINARD RIDGE MANAGEMENT
$850,000Active8 beds 8 baths3,712 sq. ft.5320 Route 23, Windham, NY 12496
MLS# 20252750Listed by: SHAW COUNTRY REALTY, INC.
$850,000Active8 beds -- baths3,712 sq. ft.5320 Route 23, Windham, NY 12496
MLS# 20252748Listed by: SHAW COUNTRY REALTY, INC.
$499,000Active4 beds 3 baths2,287 sq. ft.18 Maplewood Avenue, Windham, NY 12496
MLS# 20252508Listed by: BUNCE REALTY
$545,000Active2 beds 2 baths1,390 sq. ft.53 Windham Mountain Village, Windham, NY 12496
MLS# 20252434Listed 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
$999,000Pending7 beds 3 baths4,281 sq. ft.5474 Route 23, Windham, NY 12496
MLS# 149640Listed by: JANE H. REYNOLDS
$549,000Active7 beds 6 baths4,800 sq. ft.41 County Road 40, Windham, NY 12496
MLS# 150051Listed by: RVW SELECT PROPERTIES
$75,000Active2 Acres0 Trail View Lane, Windham, NY 12496
MLS# 155999Listed by: COLDWELL BANKER VILLAGE GREENW
$75,000Active1 Acres0 Mountain View Road, Windham, NY 12496
MLS# 156000Listed 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
$499,000Active4 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
$485,000Active3 beds 1 baths1,200 sq. ft.5134 Route 23, Windham, NY 12496
MLS# 20254112Listed by: DUGO REALTY
$439,000Active4 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
$2,200,000Active4 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 New West Properties, CENTURY 21 Stoeckeler Real Estate, 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.