Windham, NY - homes for sale

48 of 48 results displayed

New
$1,599,000Active
5 beds 4 baths4,056 sq. ft.
5433 New York 23, Windham, NY 12496
MLS# 20264601Listed by: WINDSTAR REALTY GROUP, LLC
New
$2,050,000Active
5 beds 5 baths3,150 sq. ft.
13 Stonewall Lane, Windham, NY 12496
MLS# 1037351Listed by: DOUGLAS ELLIMAN REAL ESTATE
New
$1,800,000Active
4 beds 4 baths2,770 sq. ft.
26 Stonewall Lane, Windham, NY 12496
MLS# 1037361Listed by: DOUGLAS ELLIMAN REAL ESTATE
$1,330,000Active
4 beds 4 baths4,280 sq. ft.
305 Mitchell Hollow Road, Windham, NY 12496
MLS# 1031149Listed by: FOUR SEASONS SOTHEBYS INTL
$199,000Active
1 beds 1 baths435 sq. ft.
5220 Route 23 #229, Windham, NY 12496
MLS# 20264331Listed by: COLDWELL BANKER VILLAGE GREENW
$1,275,000Active
3 beds 3 baths1,506 sq. ft.
11 Whisper Creek Drive #301b, Windham, NY 12496
MLS# 20263965Listed by: COLDWELL BANKER VILLAGE GREENW
$1,590,000Active
5 beds 3 baths2,974 sq. ft.
3-5 Hickory Hill Road, Windham, NY 12496
MLS# 20263929Listed by: VENTURE FOX REALTY GROUP
$899,000Active
6 beds 5 baths3,080 sq. ft.
5628 Route 23, Windham, NY 12496
MLS# R1697474Listed by: WINDSTAR REALTY GROUP LLC
$479,000Active
3 beds 2 baths1,652 sq. ft.
177 Mill Street, Windham, NY 12496
MLS# 20263905Listed by: BUNCE REALTY
$464,000Active
6 beds 3 baths2,251 sq. ft.
10 Vets Road, Windham, NY 12496
MLS# 20263857Listed by: BUNCE REALTY
$1,749,000Active
5 beds 4 baths3,893 sq. ft.
33 Elm Ridge Road, Windham, NY 12496
MLS# 20263447Listed by: COLDWELL BANKER VILLAGE GREENW
$610,000Active
4 beds 3 baths2,227 sq. ft.
49 Brainard Ridge Road #3a, Windham, NY 12496
MLS# 20263403Listed by: BRAINARD RIDGE MANAGEMENT
$399,000Active
4 beds 3 baths1,227 sq. ft.
5044 Ny-23, Windham, NY 12496
MLS# 20263217Listed by: WELCH REALTY INC.
$790,000Active
4 beds 2 baths2,112 sq. ft.
97 Clarence D Lane Road #D, Windham, NY 12496
MLS# 20263003Listed by: WINDSTAR REALTY GROUP, LLC
$689,000Active
5 beds -- baths2,500 sq. ft.
5355 New York 23, Windham, NY 12496
MLS# 20262874Listed by: SHAW COUNTRY REALTY, INC.
$332,000Active
3 beds 3 baths1,520 sq. ft.
69 Windham Ridge Road #16-F, Windham, NY 12496
MLS# 202618066Listed by: RE MAX CAPITAL
$269,000Active
2 beds 3 baths1,058 sq. ft.
45 Windham Ridge Road #C, Windham, NY 12496
MLS# R1682752Listed by: HOWARD HANNA
$389,000Active
2 beds 2 baths1,392 sq. ft.
21 French Park Court #7b, Windham, NY 12496
MLS# 20262629Listed by: COLDWELL BANKER VILLAGE GREENW
$799,000Active
6 beds 3 baths2,468 sq. ft.
5429 New York 23, Windham, NY 12496
MLS# 20262576Listed by: SHAW COUNTRY REALTY, INC.
$319,000Active
2 beds 3 baths1,238 sq. ft.
55 Windham Ridge Road #15h, Windham, NY 12496
MLS# 20262498Listed by: COLDWELL BANKER VILLAGE GREENW
$1,700,000Pending
4 beds 4 baths2,770 sq. ft.
23 Stonewall Lane, Windham, NY 12496
MLS# 996209Listed by: DOUGLAS ELLIMAN REAL ESTATE
$239,000Active
2 beds 2 baths1,163 sq. ft.
5359 Route 23 #2E, Windham, NY 12496
MLS# 989706Listed by: REALTY CONNECT USA LLC
$1,350,000Active
11.74 Acres
0 South Street, Windham, NY 12496
MLS# 20261395Listed by: COLDWELL BANKER VILLAGE GREENW
$319,000Active
2 beds 3 baths1,211 sq. ft.
#44 Loo Bridge Lane #14b, Windham, NY 12496
MLS# 20261025Listed by: BRAINARD RIDGE MANAGEMENT
$599,000Active
3 beds 2 baths2,250 sq. ft.
16 Hickory Hill Road, Windham, NY 12496
MLS# 20260578Listed by: SHAW COUNTRY REALTY, INC.
$1,345,000Pending
4 beds 4 baths2,856 sq. ft.
2 Watch Hill Lane #2, Windham, NY 12496
MLS# 20260488Listed by: BRAINARD RIDGE MANAGEMENT
$1,750,000Active
5 beds 5 baths3,218 sq. ft.
31 Windham Farms Road, Windham, NY 12496
MLS# 957893Listed by: FOUR SEASONS SOTHEBYS INTL
$2,650,000Active
6 beds 5 baths4,730 sq. ft.
208 Mill Street, Windham, NY 12496
MLS# 953759Listed by: ICONIC PROS
$799,000Active
3 beds 3 baths1,528 sq. ft.
71 Windham Mount Village #71, Windham, NY 12496
MLS# 20260313Listed by: SHAW COUNTRY REALTY, INC.
$499,000Active
3 beds 3 baths1,566 sq. ft.
13 Brainard Ridge Road, Windham, NY 12496
MLS# 20260225Listed by: COLDWELL BANKER VILLAGE GREENW
$325,000Active
3 beds 2 baths1,152 sq. ft.
315 Begley Road, Windham, NY 12496
MLS# 20260215Listed by: SHAW COUNTRY REALTY, INC.
$550,000Active
2 beds 1 baths1,122 sq. ft.
183 South Street, Windham, NY 12496
MLS# 20260193Listed by: SHAW COUNTRY REALTY, INC.
$427,000Active
3 beds 2 baths1,249 sq. ft.
111 Brainard Ridge Road #11b, Windham, NY 12496
MLS# 20255439Listed by: BRAINARD RIDGE MANAGEMENT
$2,175,000Active
6 beds 5 baths4,104 sq. ft.
19 Twin Maples Lane, Windham, NY 12496
MLS# 20255113Listed by: COLDWELL BANKER VILLAGE GREENW
$1,149,000Active
5 beds 6 baths3,643 sq. ft.
292 #3 South Street, Windham, NY 12496
MLS# 20254832Listed by: COLDWELL BANKER VILLAGE GREENW
$399,000Active
0.46 Acres
2 Twin Maples Lane, Windham, NY 12496
MLS# 20254820Listed by: COLDWELL BANKER VILLAGE GREENW
$749,000Active
4 beds 4 baths2,088 sq. ft.
93 Maplewood Road, Windham, NY 12496
MLS# 20254677Listed by: COLDWELL BANKER VILLAGE GREENW
$569,900Active
40.07 Acres
TBD Boulder Brook Lots 33-38 Road, Windham, NY 12496
MLS# 878815Listed by: HOWARD HANNA RAND REALTY
$449,000Active
4 beds 3 baths2,287 sq. ft.
18 Maplewood Avenue, Windham, NY 12496
MLS# 20252508Listed by: BUNCE REALTY
$545,000Active
2 beds 2 baths1,390 sq. ft.
53 Windham Mountain Village, Windham, NY 12496
MLS# 20252434Listed by: COLDWELL BANKER VILLAGE GREENW
$1,899,000Active
5 beds 5 baths3,723 sq. ft.
4 Goff Road, Windham, NY 12496
MLS# 20251987Listed by: COLDWELL BANKER VILLAGE GREENW
$549,000Active
7 beds 6 baths4,800 sq. ft.
41 County Road 40, Windham, NY 12496
MLS# 150051Listed by: RVW SELECT PROPERTIES
$75,000Active
2 Acres
0 Trail View Lane, Windham, NY 12496
MLS# 155999Listed by: COLDWELL BANKER VILLAGE GREENW
$75,000Active
1 Acres
0 Mountain View Road, Windham, NY 12496
MLS# 156000Listed by: COLDWELL BANKER VILLAGE GREENW
$999,000Active
5 beds 6 baths3,460 sq. ft.
292 South Street #2, Windham, NY 12496
MLS# 156125Listed by: COLDWELL BANKER VILLAGE GREENW
$425,000Active
4 beds 4 baths2,950 sq. ft.
25 Vets Road, Windham, NY 12496
MLS# 156676Listed by: COLDWELL BANKER VILLAGE GREENW
$460,000Active
3 beds 1 baths1,200 sq. ft.
5134 Route 23, Windham, NY 12496
MLS# 20254112Listed by: DUGO REALTY
$569,000Active
3 beds 2 baths2,182 sq. ft.
150 Vining Road, Windham, NY 12496
MLS# 20260953Listed by: COLDWELL BANKER VILLAGE GREENW

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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.

Terms of use Accessibility DMCA notice Fraud alert Privacy policy Fair housing Do not sell info NY reasonable accommodation Submit agent or broker complaint

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.