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Windham, CT
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1 - 62 of 62 listings (62 total matches)
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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 Office Phone: (860) 887-5000 Broker Contact: (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 Office Phone: (860) 887-5000 Broker Contact: (860) 884-4666
253 Brick Top Road Windham CT 06280
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 Office Phone: (877) 672-3847 Broker Contact: (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 Office Phone: (860) 228-8512 Broker Contact: (860) 450-2682
872 Main Street Windham CT 06226
1 / 5
$500,000
Commercial Sale For Sale
Active
17,400
SQFT
872 Main Street
Windham, CT 06226
 
Listing courtesy of David Mieczynski of National Realty Advisors LLC Office Phone: (877) 672-3847 Broker Contact: (860) 234-7435
121 Highland View Drive Windham CT 06266
1 / 13
$468,500
Single Family Residence For Sale
Pending
3
BEDS
2
TOTAL BATHS
1,200
SQFT
121 Highland View Drive
Windham, CT 06266
 
Listing courtesy of Timothy Morse of Alliance Realty LLC Office Phone: (860) 481-9553 Broker Contact: (860) 481-9553
757 Main Street Windham CT 06226
New Listing - 2 weeks on site
1 / 14
$450,000
Commercial Sale For Sale
Active
12,838
SQFT
757 Main Street
Windham, CT 06226
 
Listing courtesy of Paul Bongiorni of Pioneer CRE Office Phone: (413) 312-9299 Broker Contact: (413) 459-0570
55 Tuckie Road Windham CT 06280
1 / 17
$450,000
Single Family Residence For Sale
Pending
3
BEDS
3
TOTAL BATHS
2,136
SQFT
55 Tuckie Road
Windham, CT 06280
 
Listing courtesy of Mary Beth Malin of Brunet and Company Real Estate Office Phone: (860) 412-9056 Broker Contact: (860) 608-4401
97 Bass Road Windham CT 06280
1 / 40
$449,000
Single Family Residence For Sale
Pending
4
BEDS
3
TOTAL BATHS
2,464
SQFT
97 Bass Road
Windham, CT 06280
 
Listing courtesy of Lindsey Niarhakos of RE/MAX One Office Phone: (860) 429-3973 Broker Contact: (860) 377-7005
121 Insalaco Drive Windham CT 06280
New Listing - 3 weeks on site
1 / 20
$439,900
Single Family Residence For Sale
Active Under Contract
3
BEDS
3
TOTAL BATHS
2,020
SQFT
121 Insalaco Drive
Windham, CT 06280
 
Listing courtesy of Michael Thompson of Countryside Realty Office Phone: (860) 228-8512 Broker Contact: (860) 888-7653
5 Insalaco Drive Windham CT 06280
New Listing - 3 weeks on site
1 / 40
$439,900
Single Family Residence For Sale
Active Under Contract
4
BEDS
2
TOTAL BATHS
1,872
SQFT
5 Insalaco Drive
Windham, CT 06280
 
Listing courtesy of Joe Snell of Luxe Realty LLC Office Phone: (860) 839-5035 Broker Contact: (860) 839-8331
73 Spring Street Windham CT 06226
1 / 24
$385,000
Triplex For Sale
Coming Soon
9
BEDS
3
TOTAL BATHS
2,990
SQFT
73 Spring Street
Windham, CT 06226
 
Listing courtesy of Mandy Gruslin of Kazantzis Real Estate, LLC Office Phone: (860) 774-2733 Broker Contact: (860) 377-9784
41 Spring Street Windham CT 06226
1 / 15
$375,000
Triplex For Sale
Active Under Contract
9
BEDS
4
TOTAL BATHS
4,057
SQFT
41 Spring Street
Windham, CT 06226
 
Listing courtesy of Stephen Galinat of Home Selling Team Office Phone: (860) 456-7653 Broker Contact: (860) 428-1211
91 Insalaco Drive Windham CT 06280
1 / 20
$359,900
Single Family Residence For Sale
Active Under Contract
3
BEDS
3
TOTAL BATHS
2,128
SQFT
91 Insalaco Drive
Windham, CT 06280
 
Listing courtesy of Michael Thompson of Countryside Realty Office Phone: (860) 228-8512 Broker Contact: (860) 888-7653
129 Valley Street Windham CT 06226
1 / 32
$355,000
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 Office Phone: (866) 828-3951 Broker Contact: (860) 712-3723
15 Cracow Avenue Windham CT 06280
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 Office Phone: (860) 313-0700 Broker Contact: (860) 803-4037
11 Woodland Drive Windham CT 06280
1 / 10
$324,900
Single Family Residence For Sale
Active
3
BEDS
2
TOTAL BATHS
1,277
SQFT
11 Woodland Drive
Windham, CT 06280
 
Listing courtesy of Sharon Stokland of List N Show LLC Office Phone: (860) 617-2946 Broker Contact: (203) 564-3262
925 Windham Road Windham CT 06266
1 / 38
$320,000
Single Family Residence For Sale
Pending
3
BEDS
1
TOTAL BATH
1,344
SQFT
925 Windham Road
Windham, CT 06266
 
Listing courtesy of Clarence Russ of Home Selling Team Office Phone: (860) 456-7653 Broker Contact: (860) 456-7653
9 Highland View Drive Windham CT 06266
New Listing - 2 weeks on site
1 / 22
$315,000
Single Family Residence For Sale
Active Under Contract
3
BEDS
1
TOTAL BATH
960
SQFT
9 Highland View Drive
Windham, CT 06266
 
Listing courtesy of Brian Connolly of Real Broker CT, LLC Office Phone: (855) 450-0442 Broker Contact: (860) 861-2605
26 Maple Avenue Windham CT 06226
1 / 7
$309,000
Triplex For Sale
Active Under Contract
7
BEDS
3
TOTAL BATHS
2,383
SQFT
26 Maple Avenue
Windham, CT 06226
 
Listing courtesy of Heather Meehan of Meehan & Daughters Real Estate Office Phone: (860) 456-7610 Broker Contact: (860) 208-5429
34 North Windham Road Windham CT 06280
Open House Sun, Mar 8, 2 PM
Please verify times due to COVID-19
1 / 40
$299,999
Single Family Residence For Sale
Active
4
BEDS
2
TOTAL BATHS
1,294
SQFT
34 North Windham Road
Windham, CT 06280
 
Listing courtesy of Marco Epifani of The Hive Real Estate LLC Office Phone: (860) 786-2854 Broker Contact: (860) 786-2854
50 Selden Street Windham CT 06226
1 / 35
$299,900
Single Family Residence For Sale
Pending
4
BEDS
2
TOTAL BATHS
2,540
SQFT
50 Selden Street
Windham, CT 06226
 
Listing courtesy of Patrizia Puccia of KW Legacy Partners Office Phone: (860) 313-0700 Broker Contact: (860) 377-4006
165 Ballamahack Road Windham CT 06280
New Listing - 3 weeks on site
1 / 40
$299,900
Single Family Residence For Sale
Pending
3
BEDS
2
TOTAL BATHS
1,382
SQFT
165 Ballamahack Road
Windham, CT 06280
 
Listing courtesy of Anthony La Penna of Exceptional Real Estate LLC Office Phone: (860) 303-2918 Broker Contact: (860) 707-2520
119 Quercus Avenue Windham CT 06226
New Listing - 4 weeks on site
1 / 29
$299,000
Single Family Residence For Sale
Active
3
BEDS
2
TOTAL BATHS
1,160
SQFT
119 Quercus Avenue
Windham, CT 06226
 
Listing courtesy of Kristen Kaskela of Berkshire Hathaway NE Prop. Office Phone: (860) 928-1995 Broker Contact: (860) 377-0118
139 South Street Windham CT 06226
New Listing - 2 weeks on site
1 / 27
$285,900
Duplex For Sale
Pending
5
BEDS
3
TOTAL BATHS
1,848
SQFT
139 South Street
Windham, CT 06226
 
Listing courtesy of Heather Miller of RE/MAX One Office Phone: (860) 444-7362 Broker Contact: (860) 334-6919
39 South Windham Road Windham CT 06226
Open House Sun, Mar 8, 11 AM
Please verify times due to COVID-19
1 / 33
$279,900
Single Family Residence For Sale
Active
3
BEDS
1
TOTAL BATH
1,120
SQFT
39 South Windham Road
Windham, CT 06226
 
Listing courtesy of Susan Walsh of RE/MAX One Office Phone: (860) 444-7362 Broker Contact: (860) 367-1285
5 Kathleen Drive Windham CT 06226
1 / 40
$275,000
Single Family Residence For Sale
Active Under Contract
2
BEDS
2
TOTAL BATHS
1,080
SQFT
5 Kathleen Drive
Windham, CT 06226
 
Listing courtesy of Sue Esposito of Home Selling Team Office Phone: (860) 456-7653 Broker Contact: (860) 428-3201
1008 Windham Road Windham CT 06266
New Listing - a week on site
1 / 15
$269,000
Single Family Residence For Sale
Active
5
BEDS
2
TOTAL BATHS
2,340
SQFT
1008 Windham Road
Windham, CT 06266
 
Listing courtesy of Michelle Gutierrez of Social & Co Realty Office Phone: (203) 484-8061 Broker Contact: (203) 556-6608
15 Bristol Street Windham CT 06226
1 / 19
$249,900
Single Family Residence For Sale
Pending
3
BEDS
1
TOTAL BATH
1,170
SQFT
15 Bristol Street
Windham, CT 06226
 
Listing courtesy of Ted Jarrett of Berkshire Hathaway NE Prop. Office Phone: (860) 648-2045 Broker Contact: (413) 537-1914
17 Pearl Street Windham CT 06226
Open House Sun, Mar 8, 12 PM
Please verify times due to COVID-19
1 / 17
$249,900
Duplex For Sale
Active
4
BEDS
2
TOTAL BATHS
2,085
SQFT
17 Pearl Street
Windham, CT 06226
 
Listing courtesy of Ryan Newport of Social & Co Realty Office Phone: (203) 484-8061 Broker Contact: (860) 414-2265
363 Windham Road Windham CT 06226
1 / 28
$235,000
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 Office Phone: (860) 474-3500 Broker Contact: [email protected]
615 Jackson Street Windham CT 06226
1 / 2
$220,000
Single Family Residence For Sale
Pending
3
BEDS
2
TOTAL BATHS
1,433
SQFT
615 Jackson Street
Windham, CT 06226
 
Listing courtesy of Mei Ling Cheung of BHGRE Shore & Country Office Phone: (203) 504-5005 Broker Contact: (914) 752-8788
80 Old Plains Road Windham CT 06226
1 / 19
$219,000
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 Office Phone: (860) 966-2414 Broker Contact: (860) 966-2414
6 Skyline Drive 6 Windham CT 06256
1 / 39
$215,000
Condominium For Sale
Pending
3
BEDS
2
TOTAL BATHS
1,158
SQFT
Windham Oaks
6 Skyline Drive 6
Windham, CT 06256
Listing courtesy of Brianne Carrington of William Raveis Real Estate Office Phone: (203) 453-0391 Broker Contact: (619) 254-4727
235 South Windham Road Windham CT 06226
1 / 30
$199,900
Single Family Residence For Sale
Pending
2
BEDS
1
TOTAL BATH
952
SQFT
235 South Windham Road
Windham, CT 06226
 
Listing courtesy of Anthony D'Amore of eXp Realty Office Phone: (866) 828-3951 Broker Contact: (203) 915-0996
21 Russ Road Windham CT 06226
1 / 12
$199,900
Single Family Residence For Sale
Active Under Contract
4
BEDS
1
TOTAL BATH
1,152
SQFT
21 Russ Road
Windham, CT 06226
 
Listing courtesy of Christy Lofstrom of ERA Blanchard & Rossetto Office Phone: (860) 646-2482 Broker Contact: (860) 539-0533
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 Office Phone: (860) 450-1080 Broker Contact: (860) 630-0103
28 Circle Drive Windham CT 06256
1 / 35
$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 Office Phone: (860) 456-7653 Broker Contact: (860) 456-7653
16 Circle Drive Windham CT 06256
Open House Sun, Mar 8, 11 AM
Please verify times due to COVID-19
1 / 34
$159,000
Mobile Home For Sale
Active
3
BEDS
2
TOTAL BATHS
1,620
SQFT
16 Circle Drive
Windham, CT 06256
Stonegate Manor Subdivision
Listing courtesy of Danielle Allegro of Coldwell Banker Realty Office Phone: (860) 633-3661 Broker Contact: (860) 942-7721
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 Office Phone: (860) 786-7277 Broker Contact: (860) 559-6555
64 Circle Drive Windham CT 06256
Price Change - 2 weeks ago
1 / 40
$150,000
Mobile Home For Sale
Active
3
BEDS
2
TOTAL BATHS
1,620
SQFT
64 Circle Drive
Windham, CT 06256
 
Listing courtesy of Britany Goyen of BB Realty CT Office Phone: (860) 980-0829 Broker Contact: (860) 608-5824
5 Charles Street Windham CT 06226
New Listing - a week on site
1 / 6
$150,000
Single Family Residence For Sale
Active
3
BEDS
1
TOTAL BATH
1,310
SQFT
5 Charles Street
Windham, CT 06226
 
Listing courtesy of Missy Willard of Carl Guild & Associates Office Phone: (860) 474-3500 Broker Contact: [email protected]
7 Circle Drive Windham CT 06256
New Listing - 21 hours on site
1 / 36
$145,000
Mobile Home For Sale
Active
3
BEDS
2
TOTAL BATHS
1,152
SQFT
7 Circle Drive
Windham, CT 06256
 
Listing courtesy of Karen Martin of Century 21 AllPoints Realty Office Phone: (860) 228-9425 Broker Contact: (860) 559-8903
39 Pleasant View Avenue Windham CT 06226
Real Estate Owned
1 / 21
$136,500
Single Family Residence For Sale
Active
2
BEDS
1
TOTAL BATH
1,316
SQFT
39 Pleasant View Avenue
Windham, CT 06226
 
Listing courtesy of Alicia Mercer of ERA Blanchard & Rossetto Office Phone: (860) 646-2482 Broker Contact: (860) 729-9957
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 Office Phone: (860) 429-9700 Broker Contact: (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 Office Phone: (866) 828-3951 Broker Contact: (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 Office Phone: (860) 228-8512 Broker Contact: (860) 942-7405
16 Pond Way Windham CT 06256
New Listing - 2 weeks on site
1 / 22
$67,900
Mobile Home For Sale
Pending
2
BEDS
2
TOTAL BATHS
1,218
SQFT
16 Pond Way
Windham, CT 06256
 
Listing courtesy of Stephen Daly of KW Legacy Partners Office Phone: (860) 313-0700 Broker Contact: (860) 576-8183
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 Office Phone: (860) 456-7653 Broker Contact: (860) 428-3201
53 Lynwood Drive Windham CT 06226
New Listing - yesterday
1 / 10
$2,300
Single Family Residence For Rent
Active
4
BEDS
1
TOTAL BATH
1,134
SQFT
53 Lynwood Drive
Windham, CT 06226
 
Listing courtesy of Adam Zak of Century 21 Classic Homes Office Phone: (860) 633-2192 Broker Contact: (860) 328-5856
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 Office Phone: (877) 672-3847 Broker Contact: (860) 234-7435
319 Boston Post Road 6 Windham CT 06256
1 / 1
$2,000
Commercial Lease For Rent
Active
1,500
SQFT
319 Boston Post Road 6
Windham, CT 06256
 
Listing courtesy of Robert Ferrigno of Ferrigno-Willimantic REALTORS Office Phone: (860) 456-1554 Broker Contact: (860) 428-1335
270 So. Windham Road 68 Windham CT 06266
1 / 11
$1,800
Condominium For Rent
Active
2
BEDS
1
TOTAL BATH
790
SQFT
Cedar Crest
270 So. Windham Road 68
Windham, CT 06266
Listing courtesy of Roberta Cardinal of RbRE, LLC Office Phone: (860) 477-1500 Broker Contact: (860) 377-3725
80 North Street Windham CT 06226
Price Change - 3 weeks ago
1 / 16
$1,750
Multi Family For Rent
Active
2
BEDS
1
TOTAL BATH
2,652
SQFT
80 North Street
Windham, CT 06226
 
Listing courtesy of Sharon Stokland of List N Show LLC Office Phone: (860) 617-2946 Broker Contact: (203) 564-3262
260 Summit Street 2B Windham CT 06226
New Listing - 3 days on site
1 / 6
$1,650
Multi Family For Rent
Active
3
BEDS
1
TOTAL BATH
2,939
SQFT
260 Summit Street 2B
Windham, CT 06226
 
Listing courtesy of Michelle Mandel of Carl Guild & Associates Office Phone: (860) 474-3500 Broker Contact: [email protected]
260 Summit Street 3 Windham CT 06226
New Listing - 4 days on site
1 / 5
$1,400
Multi Family For Rent
Active
2
BEDS
1
TOTAL BATH
2,939
SQFT
260 Summit Street 3
Windham, CT 06226
 
Listing courtesy of Michelle Mandel of Carl Guild & Associates Office Phone: (860) 474-3500 Broker Contact: [email protected]
260 Summit Street 2A Windham CT 06226
New Listing - 3 days on site
1 / 4
$1,100
Multi Family For Rent
Active
1
TOTAL BATH
2,939
SQFT
260 Summit Street 2A
Windham, CT 06226
 
Listing courtesy of Michelle Mandel of Carl Guild & Associates Office Phone: (860) 474-3500 Broker Contact: [email protected]
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 Office Phone: (877) 672-3847 Broker Contact: (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 Office Phone: (860) 887-5000 Broker Contact: (860) 884-4666
1320 Main Street 5 Windham CT 06226
1 / 23
$18
Commercial Lease For Rent
Active
4,600
SQFT
1320 Main Street 5
Windham, CT 06226
 
Listing courtesy of Ron Lyman of Lyman Real Estate Office Phone: (860) 887-5000 Broker Contact: (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 Office Phone: (860) 887-5000 Broker Contact: (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 Office Phone: (413) 312-9299 Broker Contact: (413) 459-0570
1 - 62 of 62 listings (62 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 2026 SmartMLS, Inc.
Last checked: 2026-03-07 02:15 AM UTC.


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