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Windham, CT
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1 - 63 of 63 listings (63 total matches)
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1071 Main Street Windham CT 06226
New Listing - 4 weeks on site
1 / 22
$4,500,000
Commercial Sale For Sale
Active
8,827
SQFT
1071 Main Street
Windham, CT 06226
 
Listing courtesy of Islam Ahmad of Real Broker CT, LLC 8554500442 (203) 805-9007
1681 West Main Street Windham CT 06226
1 / 6
$3,500,000
Commercial Sale For Sale
Active
12,696
SQFT
1681 West Main Street
Windham, CT 06226
 
Listing courtesy of Ron Lyman of Lyman Real Estate 8608875000 (860) 884-4666
1548 West Main Street Windham CT 06226
1 / 3
$2,500,000
Commercial Sale For Sale
Active
14,027
SQFT
1548 West Main Street
Windham, CT 06226
 
Listing courtesy of Ron Lyman of Lyman Real Estate 8608875000 (860) 884-4666
 Windham CT 06256
1 / 39
$999,000
Single Family Residence For Sale
Active
3
BEDS
2
TOTAL BATHS
1,808
SQFT

Windham, CT 06256
 
Listing courtesy of Lori Vogel of William Raveis Real Estate 8602586202 (860) 614-0666
253 Brick Top Road Windham CT 06280
New Listing - 3 weeks on site
1 / 11
$799,900
Land For Sale
Active
56.4
ACRES
WINDHAM
COUNTY
253 Brick Top Road
Windham, CT 06280
 
Listing courtesy of David Mieczynski of National Realty Advisors LLC 8776723847 (860) 234-7435
5 Autumn Ridge Windham CT 06280
1 / 4
$527,000
Single Family Residence For Sale
Active Under Contract
4
BEDS
4
TOTAL BATHS
2,368
SQFT
5 Autumn Ridge
Windham, CT 06280
 
Listing courtesy of Cathyann Schulte of Countryside Realty 8602288512 (860) 450-2682
872 Main Street Windham CT 06226
1 / 5
$500,000
Commercial Sale For Sale
Pending
17,400
SQFT
872 Main Street
Windham, CT 06226
 
Listing courtesy of David Mieczynski of National Realty Advisors LLC 8776723847 (860) 234-7435
244 Jerusalem Road Windham CT 06280
New Listing - 4 weeks on site
1 / 36
$462,000
Single Family Residence For Sale
Active Under Contract
3
BEDS
3
TOTAL BATHS
1,622
SQFT
244 Jerusalem Road
Windham, CT 06280
 
Listing courtesy of Patricia Brown of Lebanon Green Real Estate 8606427003 [email protected]
121 Highland View Drive Windham CT 06266
1 / 13
$454,000
Single Family Residence For Sale
Active
3
BEDS
2
TOTAL BATHS
1,200
SQFT
121 Highland View Drive
Windham, CT 06266
 
Listing courtesy of Timothy Morse of Alliance Realty LLC 8604819553 (860) 481-9553
4 Main Street Windham CT 06226
1 / 40
$450,000
Triplex For Sale
Pending
9
BEDS
5
TOTAL BATHS
5,134
SQFT
4 Main Street
Windham, CT 06226
 
Listing courtesy of Tammy Arute of Arute Realty Group LLC 8606840301 (860) 916-0303
61 Oak Street Windham CT 06226
New Listing - 4 weeks on site
1 / 18
$425,000
Triplex For Sale
Pending
7
BEDS
4
TOTAL BATHS
2,769
SQFT
61 Oak Street
Windham, CT 06226
 
Listing courtesy of Julienne Jaber of KW Legacy Partners 8603130700 (860) 803-4037
4 Jerusalem Road Windham CT 06280
1 / 37
$399,900
Single Family Residence For Sale
Pending
3
BEDS
2
TOTAL BATHS
1,938
SQFT
4 Jerusalem Road
Windham, CT 06280
 
Listing courtesy of Skyla Gagnon of RE/MAX Bell Park Realty 8607747600 (860) 617-8493
127 Plains Road Windham CT 06280
1 / 13
$395,000
Duplex For Sale
Active
4
BEDS
2
TOTAL BATHS
1,700
SQFT
127 Plains Road
Windham, CT 06280
 
Listing courtesy of Patricia Malek of First Choice Realty 8607797460 (860) 377-1967
47 Insalaco Drive Windham CT 06280
1 / 24
$379,900
Single Family Residence For Sale
Pending
3
BEDS
3
TOTAL BATHS
2,112
SQFT
47 Insalaco Drive
Windham, CT 06280
 
Listing courtesy of Karan Garewal of Winwin Realty 9142425464 (914) 309-5676
41 Spring Street Windham CT 06226
1 / 15
$375,000
Triplex For Sale
Active
9
BEDS
4
TOTAL BATHS
4,057
SQFT
41 Spring Street
Windham, CT 06226
 
Listing courtesy of Stephen Galinat of Home Selling Team 8604567653 (860) 428-1211
129 Valley Street Windham CT 06226
1 / 32
$375,000
Multi Family For Sale
Active
7
BEDS
4
TOTAL BATHS
3,963
SQFT
129 Valley Street
Windham, CT 06226
 
Listing courtesy of Kyle West of eXp Realty 8668283951 (860) 712-3723
176 Windham Road Windham CT 06226
1 / 28
$369,900
Triplex For Sale
Pending
8
BEDS
3
TOTAL BATHS
3,073
SQFT
176 Windham Road
Windham, CT 06226
 
Listing courtesy of Gregory Leone of Coldwell Banker Realty 8606442461 (860) 508-7637
27 Aspen Place Windham CT 06226
New Listing - 2 weeks on site
1 / 39
$350,000
Single Family Residence For Sale
Active Under Contract
5
BEDS
3
TOTAL BATHS
1,226
SQFT
27 Aspen Place
Windham, CT 06226
 
Listing courtesy of Sue Esposito of Home Selling Team 8604567653 (860) 428-3201
231 Back Road Windham CT 06280
1 / 27
$329,999
Single Family Residence For Sale
Pending
3
BEDS
2
TOTAL BATHS
2,144
SQFT
231 Back Road
Windham, CT 06280
 
Listing courtesy of Matt Noren of RE/MAX Bell Park Realty 8607747600 (860) 428-6534
295 Jackson Street Windham CT 06226
New Listing - 4 weeks on site
1 / 40
$329,900
Duplex For Sale
Active
6
BEDS
2
TOTAL BATHS
2,576
SQFT
295 Jackson Street
Windham, CT 06226
 
Listing courtesy of Michelle Garabedian of Home Selling Team 8604567653 (860) 208-3456
15 Cracow Avenue Windham CT 06280
New Listing - 3 days on site
1 / 37
$325,000
Single Family Residence For Sale
Active
3
BEDS
3
TOTAL BATHS
1,228
SQFT
15 Cracow Avenue
Windham, CT 06280
 
Listing courtesy of Julienne Jaber of KW Legacy Partners 8603130700 (860) 803-4037
45 High Street Windham CT 06226
1 / 13
$300,000
Commercial Sale For Sale
Active
2
TOTAL BATHS
1,424
SQFT
45 High Street
Windham, CT 06226
 
Listing courtesy of David Mieczynski of National Realty Advisors LLC 8776723847 (860) 234-7435
205 Ballamahack Road Windham CT 06280
New Listing - 3 weeks on site
1 / 29
$299,900
Duplex For Sale
Pending
4
BEDS
3
TOTAL BATHS
1,960
SQFT
205 Ballamahack Road
Windham, CT 06280
 
Listing courtesy of Christine Johnson of RE/MAX One 8604447362 (860) 803-5915
162 Scotland Road Windham CT 06280
New Listing - 6 days on site
1 / 31
$299,000
Single Family Residence For Sale
Active
3
BEDS
2
TOTAL BATHS
1,401
SQFT
162 Scotland Road
Windham, CT 06280
 
Listing courtesy of Dillon Cass of eRealty Advisors, Inc. 2039893635 (914) 278-4363
586 Back Road Windham CT 06256
New Listing - 2 weeks on site
1 / 32
$299,000
Single Family Residence For Sale
Active Under Contract
2
BEDS
1
TOTAL BATH
996
SQFT
586 Back Road
Windham, CT 06256
 
Listing courtesy of Jeremy Oliver of William Raveis Real Estate 2034530391 (646) 510-1038
 Windham CT 06280
Short Sale
1 / 1
$295,000
Single Family Residence For Sale
Active
3
BEDS
3
TOTAL BATHS
1,248
SQFT

Windham, CT 06280
 
Listing courtesy of Valerie Yankus of Property Shoppe, LLC 2038290418 (203) 910-2756
359 Plains Road Windham CT 06226
1 / 40
$289,000
Single Family Residence For Sale
Pending
3
BEDS
2
TOTAL BATHS
1,900
SQFT
359 Plains Road
Windham, CT 06226
 
Listing courtesy of Avi Ron of SSG Real Estate LLC 8606574754 (571) 399-6169
96 Beacon Road Windham CT 06280
New Listing - 4 weeks on site
1 / 22
$269,900
Single Family Residence For Sale
Pending
3
BEDS
2
TOTAL BATHS
1,284
SQFT
96 Beacon Road
Windham, CT 06280
 
Listing courtesy of Mark Benard of Brunet and Company Real Estate 8604129056 (860) 377-1906
89 Spring Street Windham CT 06226
Price Change - 4 days ago
1 / 36
$264,900
Single Family Residence For Sale
Active
4
BEDS
2
TOTAL BATHS
1,907
SQFT
89 Spring Street
Windham, CT 06226
 
Listing courtesy of Joshua Brown of KW Legacy Partners 8603130700 (860) 328-0166
59 Lynwood Drive Windham CT 06226
New Listing - 3 weeks on site
1 / 28
$262,000
Single Family Residence For Sale
Pending
3
BEDS
1
TOTAL BATH
1,274
SQFT
59 Lynwood Drive
Windham, CT 06226
 
Listing courtesy of Barbara Hernandez of RE/MAX One 8604447362 (860) 514-9551
363 Windham Road Windham CT 06226
Price Change - 4 weeks ago
1 / 20
$250,000
Single Family Residence For Sale
Active
3
BEDS
2
TOTAL BATHS
2,219
SQFT
363 Windham Road
Windham, CT 06226
 
Listing courtesy of Christine Homa of Carl Guild & Associates 8604743500 [email protected]
261 Beaver Hill Road Windham CT 06256
1 / 25
$249,925
Single Family Residence For Sale
Pending
4
BEDS
2
TOTAL BATHS
1,184
SQFT
261 Beaver Hill Road
Windham, CT 06256
 
Listing courtesy of Jayson Kemp of Five Stars Realty 8605601500 (860) 573-0277
10 North Road Windham CT 06280
1 / 40
$249,000
Single Family Residence For Sale
Active Under Contract
2
BEDS
2
TOTAL BATHS
1,380
SQFT
10 North Road
Windham, CT 06280
 
Listing courtesy of Taylor Gildein of Re/Max Results 4018487827 (508) 523-4935
76 South Windham Road Windham CT 06226
New Listing - 3 weeks on site
1 / 24
$239,925
Single Family Residence For Sale
Active Under Contract
3
BEDS
2
TOTAL BATHS
1,002
SQFT
76 South Windham Road
Windham, CT 06226
 
Listing courtesy of Jayson Kemp of Five Stars Realty 8605601500 (860) 573-0277
84 Machine Shop Hill Road Windham CT 06266
1 / 28
$229,900
Single Family Residence For Sale
Pending
2
BEDS
2
TOTAL BATHS
1,436
SQFT
84 Machine Shop Hill Road
Windham, CT 06266
 
Listing courtesy of Scott Bayne of Century 21 Bay-Mar Realty 8605827404 (860) 582-7404
80 Old Plains Road Windham CT 06226
1 / 19
$229,000
Single Family Residence For Sale
Active
3
BEDS
1
TOTAL BATH
994
SQFT
80 Old Plains Road
Windham, CT 06226
 
Listing courtesy of Justin Marino of Marino Realty LLC 8609662414 (860) 966-2414
50 South Street Windham CT 06226
Short Sale
1 / 6
$198,500
Single Family Residence For Sale
Pending
4
BEDS
2
TOTAL BATHS
1,152
SQFT
50 South Street
Windham, CT 06226
 
Listing courtesy of Franchesca Pescatello of Prue Realty LLC 8604501080 (860) 630-0103
59 Chestnut Street Windham CT 06226
1 / 1
$197,500
Triplex For Sale
Pending
8
BEDS
3
TOTAL BATHS
3,307
SQFT
59 Chestnut Street
Windham, CT 06226
 
Listing courtesy of Kyle Seyboth of Century 21 Limitless 5086176920 (508) 726-3492
33 Machine Shop Hill Road Windham CT 06266
1 / 1
$170,000
Duplex For Sale
Pending
5
BEDS
1
TOTAL BATH
2,548
SQFT
33 Machine Shop Hill Road
Windham, CT 06266
 
Listing courtesy of Franchesca Pescatello of Prue Realty LLC 8604501080 (860) 630-0103
28 Circle Drive Windham CT 06256
New Listing - 4 weeks on site
1 / 26
$168,500
Mobile Home For Sale
Active
3
BEDS
2
TOTAL BATHS
1,152
SQFT
28 Circle Drive
Windham, CT 06256
 
Listing courtesy of Clarence Russ of Home Selling Team 8604567653 (860) 456-7653
335 Pleasant Street Windham CT 06226
1 / 6
$150,000
Land For Sale
Pending
3.1
ACRES
WINDHAM
COUNTY
335 Pleasant Street
Windham, CT 06226
 
Listing courtesy of Ben Kruse of Simply Sold Real Estate 8607867277 (860) 559-6555
96 Lewiston Avenue Windham CT 06226
1 / 22
$150,000
Commercial Sale For Sale
Active
3
TOTAL BATHS
1,860
SQFT
96 Lewiston Avenue
Windham, CT 06226
 
Listing courtesy of Brian Schneider of RE/MAX One 8608751818 (860) 477-7239
270 South Windham Road APT 53 Windham CT 06226
1 / 28
$115,000
Condominium For Sale
Active Under Contract
2
BEDS
1
TOTAL BATH
765
SQFT
Cedar Crest
270 South Windham Road APT 53
Windham, CT 06226
Listing courtesy of Michael Price of KW Legacy Partners 8603130700 (860) 573-1384
361 South Windham Road Windham CT 06226
1 / 1
$109,000
Commercial Sale For Sale
Pending
4,079
SQFT
361 South Windham Road
Windham, CT 06226
 
Listing courtesy of Lawrence Ross of Weichert,REALTORS-Four Corners 8604299700 (860) 377-0408
38 Elm Street Windham CT 06226
1 / 9
$84,900
Unimproved Land For Sale
Active
1.1
ACRES
WINDHAM
COUNTY
38 Elm Street
Windham, CT 06226
 
Listing courtesy of Tammy Lucier of eXp Realty 8668283951 (860) 878-7475
23 Pond Way Windham CT 06256
1 / 17
$74,900
Mobile Home For Sale
Active
2
BEDS
1
TOTAL BATH
938
SQFT
23 Pond Way
Windham, CT 06256
 
Listing courtesy of Krystal Delorge of Countryside Realty 8602288512 (860) 942-7405
48 James Drive Windham CT 06256
New Listing - 6 days on site
1 / 12
$45,000
Mobile Home For Sale
Active Under Contract
3
BEDS
2
TOTAL BATHS
924
SQFT
48 James Drive
Windham, CT 06256
 
Listing courtesy of Clarence Russ of Home Selling Team 8604567653 (860) 456-7653
248 Tuckie Road Windham CT 06256
1 / 3
$40,000
Land For Sale
Pending
1.08
ACRES
WINDHAM
COUNTY
248 Tuckie Road
Windham, CT 06256
 
Listing courtesy of Sue Esposito of Home Selling Team 8604567653 (860) 428-3201
275 High Street Windham CT 06226
1 / 27
$2,600
Single Family Residence For Rent
Pending
4
BEDS
2
TOTAL BATHS
1,378
SQFT
275 High Street
Windham, CT 06226
 
Listing courtesy of Robyn Letourneau of Berkshire Hathaway NE Prop. 8602674481 (860) 918-3945
32 Quarry Street Windham CT 06226
1 / 16
$2,500
Single Family Residence For Rent
Pending
4
BEDS
2
TOTAL BATHS
912
SQFT
32 Quarry Street
Windham, CT 06226
 
Listing courtesy of Robyn Letourneau of Berkshire Hathaway NE Prop. 8602674481 (860) 918-3945
21 Church Street Windham CT 06226
1 / 7
$2,000
Commercial Lease For Rent
Active
2,593
SQFT
21 Church Street
Windham, CT 06226
 
Listing courtesy of David Mieczynski of National Realty Advisors LLC 8776723847 (860) 234-7435
416 Jerusalem Road Windham CT 06280
1 / 39
$2,000
Single Family Residence For Rent
Pending
2
BEDS
2
TOTAL BATHS
1,408
SQFT
416 Jerusalem Road
Windham, CT 06280
 
Listing courtesy of Sondra Reid of Home Selling Team 8604567653 (860) 457-8472
45 High Street Windham CT 06226
1 / 12
$2,000
Commercial Lease For Rent
Active
1,424
SQFT
45 High Street
Windham, CT 06226
 
Listing courtesy of David Mieczynski of National Realty Advisors LLC 8776723847 (860) 234-7435
14 Turner Street 1 Windham CT 06226
Price Change - 4 days ago
1 / 20
$1,975
Multi Family For Rent
Active
3
BEDS
1
TOTAL BATH
1,100
SQFT
14 Turner Street 1
Windham, CT 06226
 
Listing courtesy of Nancy Jacques of Brass Key Realty, LLC 8605080785 (860) 508-0785
399 High Street Windham CT 06226
New Listing - 6 days on site
1 / 37
$1,900
Single Family Residence For Rent
Active
3
BEDS
2
TOTAL BATHS
1,327
SQFT
399 High Street
Windham, CT 06226
 
Listing courtesy of Karan Garewal of Winwin Realty 9142425464 (914) 309-5676
1153 Main Street 3A Windham CT 06226
1 / 13
$1,800
Apartment For Rent
Active
2
BEDS
1
TOTAL BATH
805
SQFT
1153 Main Street 3A
Windham, CT 06226
 
Listing courtesy of Olivia Crable of Berkshire Hathaway NE Prop. 8602674481 (860) 819-1935
1153 Main Street 3B Windham CT 06226
1 / 12
$1,800
Apartment For Rent
Active
2
BEDS
1
TOTAL BATH
805
SQFT
1153 Main Street 3B
Windham, CT 06226
 
Listing courtesy of Olivia Crable of Berkshire Hathaway NE Prop. 8602674481 (860) 819-1935
90 Chapman Street Windham CT 06226
New Listing - 3 weeks on site
1 / 12
$1,700
Single Family Residence For Rent
Active
3
BEDS
1
TOTAL BATH
688
SQFT
90 Chapman Street
Windham, CT 06226
 
Listing courtesy of Heather Meehan of Meehan & Daughters Real Estate 8604567610 (860) 208-5429
49 Gem Drive Windham CT 06226
1 / 3
$1,695
Single Family Residence For Rent
Active
3
BEDS
2
TOTAL BATHS
912
SQFT
49 Gem Drive
Windham, CT 06226
 
Listing courtesy of Kathy Dubay of I.M.A. Realty LLC 8604233936 (860) 423-3936
162 Mansfield Avenue Windham CT 06226
1 / 8
$18
Commercial Lease For Rent
Active
4,248
SQFT
162 Mansfield Avenue
Windham, CT 06226
 
Listing courtesy of David Mieczynski of National Realty Advisors LLC 8776723847 (860) 234-7435
1681 West Main Street Windham CT 06226
1 / 6
$18
Commercial Lease For Rent
Active
4,912
SQFT
1681 West Main Street
Windham, CT 06226
 
Listing courtesy of Ron Lyman of Lyman Real Estate 8608875000 (860) 884-4666
1548 West Main Street 3 Windham CT 06226
1 / 14
$14
Commercial Lease For Rent
Active
9,841
SQFT
1548 West Main Street 3
Windham, CT 06226
 
Listing courtesy of Ron Lyman of Lyman Real Estate 8608875000 (860) 884-4666
757 Main Street Windham CT 06226
1 / 14
$12
Commercial Lease For Rent
Active
12,838
SQFT
757 Main Street
Windham, CT 06226
 
Listing courtesy of Paul Bongiorni of Pioneer CRE 4133129299 (413) 459-0570
1 - 63 of 63 listings (63 total matches)


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 2025 SmartMLS, Inc.
Last checked: 2025-12-07 08:26 PM UTC.


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