Vintage homes for sale & real estate in Windham County, CT

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ABOUT THIS HOME
Vintage Home for sale in Windham County, CT:
OH Sunday 12/07. Highest & Best by 12/13! 2.5 Acres with a beautiful updated 3 bed, 2 bath. 1400 sqft home with a detached garage and a barn with electric hookups that also sit on the property! Discover the charm and potential of this Windham property, offering a spacious layout and a peaceful setting in a desirable location. Perfect for buyers seeking comfort, convenience, and room. Enjoy close proximity to local amenities, schools, and major routes while still benefiting from a serene, private atmosphere. Heat is off until oil is ordered this weekend.

$299,000

3 beds2 baths1,401 sq ft

162 Scotland Rd, Windham, CT 06280

2.5 acres • Peaceful setting • Spacious layout

ABOUT THIS HOME
Vintage Home for sale in Windham County, CT:
Cute, comfortable home in Pomfret on a nice 1.6 acre lot. The house has been updated with new flooring, remodeled kitchen, and roof. Gardening, lawn games, or just a place to run, the yard can accommodate. The dining area is bright, with southern and western exposer. There is a propane fireplace in the living room to supplement the heat. Nice enclosed porch on the front, and a deck on the side. The primary bedroom is on the first level, as is the laundry. The two story, two stall, detached garage was built in 2000, with a loft for storage or a bonus room. The driveway is shared, but there is plenty of parking. The town record states 1160sqft, however there is 200sqft of finished space where

$349,000

3 beds1 bath1,160 sq ft

2 Hampton Rd, Pomfret Center, CT 06259

Propane fireplace • Remodeled kitchen • 1.6 acre lot

ABOUT THIS HOME
Vintage Home for sale in Windham County, CT:
A compelling investment opportunity in the center of Putnam, this 1867 Victorian style home combines historic appeal with practical updates and multiple paths for added value. Used today as a two-family, the property offers spacious floor plans, high ceilings, and a layout that lends itself to strong rental demand or a comfortable owner-occupied arrangement. Recent improvements include mini-split heating and cooling units on the first and second floors, bathroom updates, a new chimney liner for the boiler, and upgraded exterior doors for improved efficiency. The second floor features washer and dryer hookups and has the square footage to support potential reconfiguration, pending town appro

$445,000

5 beds3.5 baths3,719 sq ft

16 Wilkinson St, Putnam, CT 06260

0.3 acre lot • 2 garage spots • Built 1867

ABOUT THIS HOME
Vintage Home for sale in Windham County, CT:
MULTIPLE OFFERS: Highest & Best Due Sunday 12-7-25 at Noon. Beautifully Renovated Home at an Incredible Value! Why keep renting when you can own? This fully renovated 3-bedroom, 1-bathroom home offers clean, safe, and comfortable living with modern updates throughout. Enjoy spacious bedrooms, an updated kitchen and bathroom, hardwood floors, and a large private yard perfect for relaxing or entertaining. Major improvements include a young roof, new hot water tank, new well pump, and an updated heating system, giving you peace of mind for years to come. Located within walking distance to shopping outlets, restaurants, and major highways, this home makes commuting and everyday convenienc

$219,900

3 beds1 bath1,575 sq ft

1067 N Main St, Killingly, CT 06241

Renovated home • Large private yard • Updated kitchen

ABOUT THIS HOME
Vintage Home for sale in Windham County, CT:
This three-bedroom, two-bathroom home, situated on two acres conveniently located off Route 6, offers a detached one-car garage with a loft and man door. It is equipped with a fireplace featuring a Heatilator, generator hookup, security system and a spacious sunroom. This property presents ample renovation opportunities to customize it to your preferences.

$295,000

3 beds2 baths1,652 sq ft

337 Hampton Rd, Chaplin, CT 06235

Security system • Spacious sunroom • Generator hookup

Property at 75 Lisbon Rd, Canterbury, CT 06331, 1 bed, 1 bath

$225,000

1 bed1 bath782 sq ft

75 Lisbon Rd, Canterbury, CT 06331

Property at 245 Brooklyn Rd, Canterbury, CT 06331, 4 beds, 2.5 baths

$750,000

4 beds2.5 baths3,285 sq ft

245 Brooklyn Rd, Canterbury, CT 06331

Property at 150 Gager Hill Rd, Windham, CT 06280, 6 beds, 1.5 baths

$179,900

6 beds1.5 baths2,634 sq ft

150 Gager Hill Rd, Windham, CT 06280

Property at 5 Chappell St, Chaplin, CT 06235, 3 beds, 2.5 baths

$345,000

3 beds2.5 baths1,748 sq ft

5 Chappell St, Chaplin, CT 06235

Property at 23 Mechanics St #101, Putnam, CT 06260, 1 bed, 1 bath

$129,000

1 bed1 bath448 sq ft

23 Mechanics St #101, Putnam, CT 06260

Property at 10 Topview Dr, Thompson, CT 06262, 1 bed, 1 bath

$315,000

1 bed1 bath1,586 sq ft

10 Topview Dr, Thompson, CT 06262

Property at 363 Windham Rd, Willimantic, CT 06226, 3 beds, 2 baths

$250,000

3 beds2 baths2,219 sq ft

363 Windham Rd, Willimantic, CT 06226

Property at 33 Railroad Ave, Plainfield, CT 06374, 3 beds, 1 bath

$245,000

3 beds1 bath1,504 sq ft

33 Railroad Ave, Plainfield, CT 06374

Property at 633 Wauregan Rd, Brooklyn, CT 06234, 3 beds, 2 baths

$419,900

3 beds2 baths1,716 sq ft

633 Wauregan Rd, Brooklyn, CT 06234

Property at 89 Spring St, Willimantic, CT 06226, 4 beds, 1.5 baths

$264,900

4 beds1.5 baths1,907 sq ft

89 Spring St, Willimantic, CT 06226

Property at 181 Snake Meadow Rd, Moosup, CT 06354, 3 beds, 2 baths

$399,000

3 beds2 baths2,050 sq ft

181 Snake Meadow Rd, Moosup, CT 06354

Property at Undisclosed address, Chaplin, CT 06235, 3 beds, 1 bath

$315,000

3 beds1 bath1,267 sq ft

Undisclosed address, Chaplin, CT 06235

Property at 29 Union St, Moosup, CT 06354, 4 beds, 1 bath

$260,000

4 beds1 bath1,865 sq ft

29 Union St, Moosup, CT 06354

Property at 409 Main St, Killingly, CT 06239, 8 beds, 5.5 baths

$549,900

8 beds5.5 baths4,670 sq ft

409 Main St, Killingly, CT 06239

Property at 462 Norwich Rd, Plainfield, CT 06374, 3 beds, 1.5 baths

$259,000

3 beds1.5 baths2,280 sq ft

462 Norwich Rd, Plainfield, CT 06374

Property at 295 Jackson St, Willimantic, CT 06226, 6 beds, 2 baths

$329,900

6 beds2 baths2,576 sq ft

295 Jackson St, Willimantic, CT 06226

Property at 69 Wauregan Rd, Killingly, CT 06239, 3 beds, 1 bath

$285,000

3 beds1 bath1,178 sq ft

69 Wauregan Rd, Killingly, CT 06239

Property at 102 Cottage St, Killingly, CT 06239, 8 beds, 4 baths

$279,000

8 beds4 baths3,951 sq ft

102 Cottage St, Killingly, CT 06239

Property at 12 Armitage Ct, Ashford, CT 06278, 3 beds, 2 baths

$585,000

3 beds2 baths1,368 sq ft

12 Armitage Ct, Ashford, CT 06278

Property at 133 Maple St, Killingly, CT 06239, 4 beds, 4.5 baths

$399,900

4 beds4.5 baths3,029 sq ft

133 Maple St, Killingly, CT 06239

Property at 7 Florence St, Putnam, CT 06260, 5 beds, 3 baths

$475,000

5 beds3 baths2,400 sq ft

7 Florence St, Putnam, CT 06260

Property at 41 Spring St, Willimantic, CT 06226, 9 beds, 3.5 baths

$375,000

9 beds3.5 baths4,057 sq ft

41 Spring St, Willimantic, CT 06226

Property at 34 Pleasant St #7, Plainfield, CT 06374, 3 beds, 1.5 baths

$249,900

3 beds1.5 baths1,259 sq ft

34 Pleasant St #7, Plainfield, CT 06374

Property at 140 Ragged Hill Rd, Pomfret Center, CT 06259, 3 beds, 2 baths

$499,900

3 beds2 baths1,102 sq ft

140 Ragged Hill Rd, Pomfret Center, CT 06259

Property at 224 Pomfret St, Putnam, CT 06260, 3 beds, 2 baths

$399,000

3 beds2 baths1,944 sq ft

224 Pomfret St, Putnam, CT 06260

Property at 393 N Canterbury Rd, Canterbury, CT 06331, 5 beds, 2 baths

$595,000

5 beds2 baths2,443 sq ft

393 N Canterbury Rd, Canterbury, CT 06331

Property at 34 Pleasant St #3, Plainfield, CT 06374, 2 beds, 1 bath

$219,500

2 beds1 bath1,188 sq ft

34 Pleasant St #3, Plainfield, CT 06374

Property at 26 Perkins St, Plainfield, CT 06374, 3 beds, 1.5 baths

$323,000

3 beds1.5 baths1,760 sq ft

26 Perkins St, Plainfield, CT 06374

Property at 7 Devotion Rd, Scotland, CT 06264, 4 beds, 2 baths

$415,000

4 beds2 baths1,787 sq ft

7 Devotion Rd, Scotland, CT 06264

Property at 48 Wrights Crossing Rd, Pomfret Center, CT 06259, 3 beds, 3 baths

$647,000

3 beds3 baths2,546 sq ft

48 Wrights Crossing Rd, Pomfret Center, CT 06259

Property at 395 Bailey Hill Rd, Killingly, CT 06239, 3 beds, 2 baths

$485,000

3 beds2 baths2,170 sq ft

395 Bailey Hill Rd, Killingly, CT 06239

Property at 132 Grove St, Putnam, CT 06260, 3 beds, 1 bath

$340,900

3 beds1 bath1,344 sq ft

132 Grove St, Putnam, CT 06260

Property at 17 Green Is, Thompson, CT 06277, 2 beds, 1 bath

$369,900

2 beds1 bath440 sq ft

17 Green Is, Thompson, CT 06277

Property at 101 Child Hill Rd, Woodstock, CT 06281, 4 beds, 3 baths

$549,000

4 beds3 baths2,150 sq ft

101 Child Hill Rd, Woodstock, CT 06281

Property at 144 Prospect Ave, Killingly, CT 06239, 6 beds, 2 baths

$289,999

6 beds2 baths2,600 sq ft

144 Prospect Ave, Killingly, CT 06239

Property at 69 N Bedlam Rd, Chaplin, CT 06235, 3 beds, 2 baths

$599,000

3 beds2 baths1,979 sq ft

69 N Bedlam Rd, Chaplin, CT 06235

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Vintage Homes for Sale in Windham County

There are currently 55 vintage homes for sale in Windham County at a median listing price of $395K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Windham County stay on the market for 50 days and receive 1 offers. This map is refreshed with the newest listings in Windham County every 15 minutes.

In the past month, 93 homes have been sold in Windham County. In addition to houses in Windham County, there were also 26 condos, 1 townhouse, and 24 multi-family units for sale in Windham County last month. Find your dream home in Windham County using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Windham County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Windham County. If you're looking to sell your home in the Windham County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Windham County with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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