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

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FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Windham County, CT:
Historic 1850 Charm with Modern Updates & In-Law Living! Step inside this beautifully remodeled 1850 home, thoughtfully updated for today's lifestyle while maintaining the character and charm that makes an older home so special. The main living portion of the home offers 3 spacious bedrooms, 2.5 baths, and a dedicated office space. The heart of the home features a bright and inviting open-concept kitchen, dining room, and living room, providing a comfortable layout for everyday living and entertaining. Main-level laundry adds even more convenience. The separate in-law living area offers first-floor living with 1 bedroom, 1 full bath, its own laundry area, and comfortable living space-

$549,900

4 beds3.5 baths2,548 sq ft

33 Machine Shop Hill Rd, South Windham, CT 06266

Modern updates • Open-concept kitchen • Historic charm

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Windham County, CT:
BACK ON MARKET - NO FAULT OF THE PROPERTY! Buyer's circumstances changed prior to inspections being completed, giving you a second opportunity to make this home yours. Don't miss your chance! Welcome to 25 Provost Lane in Killingly! This charming 3-bedroom, 1.5-bath home is set on a beautiful, spacious lot with a peaceful brook running along the property, creating a wonderful backyard setting. Enjoy summer days by the in-ground gunite pool, complete with a pool house and plenty of outdoor space for entertaining, relaxing, and making memories. The inviting front porch with Trex decking is the perfect spot to enjoy your morning coffee or unwind at the end of the day. Inside, the partially fin

$469,900

3 beds1.5 baths1,597 sq ft

25 Provost Ln, Dayville, CT 06241

Quiet road • Front porch • Pool house

ABOUT THIS HOME
Vintage Home for sale in Windham County, CT:
This well-maintained duplex offers an excellent opportunity for investors or owner-occupants looking to build equity while generating rental income. Each unit features 3 bedrooms, 1 full bathroom, and nearly 1,300 square feet of living space, providing spacious layouts and strong rental potential. One unit will be vacant at the time of purchase and has been recently renovated, allowing a new owner the flexibility to move in, secure a new tenant at current market rates, or utilize the unit as an owner-occupied residence. The second unit is currently tenant-occupied and generates $1,700 per month in rental income, providing immediate cash flow from day one. Both units feature individual basem

$389,900

6 beds2 baths2,673 sq ft

81-83 Community Ave, Plainfield, CT 06374

Spacious layouts • Individual basements • Recently renovated

ABOUT THIS HOME
Vintage Home for sale in Windham County, CT:
CHARMING 1752 QUINTESSENTIAL CENTER CHIMNEY COLONIAL ON NEARLY 2 ACRES OF PRETTY LANDSCAPE. LOVINGLY MAINTAINED FOR OVER 40 YEARS THIS CAPTIVATING CLASSIC FEATURES ORIGINAL PERIOD DETAILS HIGHLIGHTING 5 WORKING FIREPLACES WOW, FUNCTIONAL BEEHIVE OVEN, ORIGINAL BUTTERY, WONDERFUL CHESTNUT AND PINE WIDE BOARD FLOORS AND 2 STAIRCASES. SPACIOUS EAT-IN-KITCHEN WITH UPDATED STAINLESS APPLIANCES, CORIAN COUNTEROPS AND FARMHOUSE SINK SIT BY THE FIRPLACE AND ENJOY! THE KITCHEN OPENS TO A KEEPING ROOM WHERE YOU CAN GATHER AROUND THE BEEHIVE OVEN AND HEARTH. THE MAIN LEVEL CONTINUES WITH THE FORMAL DINING ROOM, PINK PARLOR AND DEN WHICH LEADS TO RELAXING TIME IN THE SCREENED IN PORCH. THE SECOND FLOOR

$399,600

3 beds2 baths2,700 sq ft

11 N Canterbury Rd, Canterbury, CT 06331

Working fireplaces • Farmhouse sink • Original buttery

ABOUT THIS HOME
Vintage Home for sale in Windham County, CT:
Welcome to 609 Norwich Road, Plainfield-a spacious and unique contemporary home offering approximately 2,800 square feet of living space. This property features 4 bedrooms, 2.5 bathrooms, and a stunning addition highlighted by a dramatic floor-to-ceiling fieldstone fireplace, cathedral ceilings, and walls of windows that flood the space with natural light. The flexible floor plan includes a private office, spacious primary suite, three additional bedrooms, hardwood floors, a three-season porch, detached one-car garage, and a full basement with high ceilings. The addition offers excellent potential for multigenerational living or a private guest suite. This home requires updating, repairs, a

$285,000

4 beds2.5 baths2,820 sq ft

609 Norwich Rd, Plainfield, CT 06374

Walls of windows • Private office • Cathedral ceilings

Property at 233 Fire Tower Rd, Pomfret Center, CT 06259, 4 beds, 2.5 baths

$799,900

4 beds2.5 baths2,982 sq ft

233 Fire Tower Rd, Pomfret Center, CT 06259

Property at 207 Summit St, Willimantic, CT 06226, 3 beds, 2 baths

$365,000

3 beds2 baths2,318 sq ft

207 Summit St, Willimantic, CT 06226

Property at 202 S Main St, Putnam, CT 06260, 3 beds, 1 bath

$349,900

3 beds1 bath1,600 sq ft

202 S Main St, Putnam, CT 06260

Property at 11 Cottage St, Putnam, CT 06260, 2 beds, 1 bath

$190,000

2 beds1 bath864 sq ft

11 Cottage St, Putnam, CT 06260

Property at 983 Riverside Dr, North Grosvenordale, CT 06255, 5 beds, 2 baths

$325,000

5 beds2 baths2,040 sq ft

983 Riverside Dr, North Grosvenordale, CT 06255

Property at 1530 Hartford Pike, East Killingly, CT 06243, 5 beds, 4 baths

$699,900

5 beds4 baths3,018 sq ft

1530 Hartford Pike, East Killingly, CT 06243

Property at 13 Bates Rd, Chaplin, CT 06235, 5 beds, 2.5 baths

$419,900

5 beds2.5 baths2,887 sq ft

13 Bates Rd, Chaplin, CT 06235

Property at 61-63 Pomfret St, Putnam, CT 06260, 7 beds, 2.5 baths

$450,000

7 beds2.5 baths2,198 sq ft

61-63 Pomfret St, Putnam, CT 06260

Property at 8 Palmer Rd, Scotland, CT 06264, 2 beds, 2 baths

$299,908

2 beds2 baths3,144 sq ft

8 Palmer Rd, Scotland, CT 06264

Property at 602 N Main St, Killingly, CT 06239, 3 beds, 2 baths

$275,000

3 beds2 baths1,467 sq ft

602 N Main St, Killingly, CT 06239

Property at 288 Bedlam Rd, Chaplin, CT 06235, 3 beds, 1 bath

$369,900

3 beds1 bath1,710 sq ft

288 Bedlam Rd, Chaplin, CT 06235

Property at 350 Hartford Pike, Dayville, CT 06241, 4 beds, 2.5 baths

$575,000

4 beds2.5 baths3,100 sq ft

350 Hartford Pike, Dayville, CT 06241

Property at 37 Van Den Noort St, Putnam, CT 06260, 5 beds, 2.5 baths

$399,900

5 beds2.5 baths4,063 sq ft

37 Van Den Noort St, Putnam, CT 06260

Property at 31 Mill St, Putnam, CT 06260, 5 beds, 3 baths

$435,000

5 beds3 baths2,392 sq ft

31 Mill St, Putnam, CT 06260

Property at 19-21 Mohegan St, Putnam, CT 06260, 6 beds, 1.5 baths

$449,900

6 beds1.5 baths2,354 sq ft

19-21 Mohegan St, Putnam, CT 06260

Property at 429 New Sweden Rd, Woodstock, CT 06281, 3 beds, 2.5 baths

$625,000

3 beds2.5 baths2,478 sq ft

429 New Sweden Rd, Woodstock, CT 06281

Property at 250 Killingly Rd, Pomfret Center, CT 06259, 5 beds, 3 baths

$689,000

5 beds3 baths3,182 sq ft

250 Killingly Rd, Pomfret Center, CT 06259

Property at 40 Main St, Plainfield, CT 06374, 6 beds, 4.5 baths

$1,100,000

6 beds4.5 baths5,856 sq ft

40 Main St, Plainfield, CT 06374

Property at 14 Carey St, Willimantic, CT 06226, 6 beds, 3 baths

$299,900

6 beds3 baths2,700 sq ft

14 Carey St, Willimantic, CT 06226

Property at 1147 Plainfield Pike, Sterling, CT 06373, 5 beds, 3 baths

$470,000

5 beds3 baths3,050 sq ft

1147 Plainfield Pike, Sterling, CT 06373

Property at 176 S Main St, Putnam, CT 06260, 9 beds, 3 baths

$385,000

9 beds3 baths3,033 sq ft

176 S Main St, Putnam, CT 06260

Property at 31-33 Brunswick Ave, Moosup, CT 06354, 6 beds, 2 baths

$359,000

6 beds2 baths2,383 sq ft

31-33 Brunswick Ave, Moosup, CT 06354

Property at 9 E Franklin St, Killingly, CT 06239, 6 beds, 5 baths

$649,900

6 beds5 baths4,134 sq ft

9 E Franklin St, Killingly, CT 06239

Property at 165 Huntington Rd, Scotland, CT 06264, 3 beds, 3.5 baths

$515,000

3 beds3.5 baths3,052 sq ft

165 Huntington Rd, Scotland, CT 06264

Property at 433 Wrights Crossing Rd, Pomfret Center, CT 06259, 12 beds, 8 baths

$6,950,000

12 beds8 baths10,517 sq ft

433 Wrights Crossing Rd, Pomfret Center, CT 06259

Property at 110 Church St, Putnam, CT 06260, 7 beds, 3 baths

$529,900

7 beds3 baths3,071 sq ft

110 Church St, Putnam, CT 06260

Property at 37 Ruth St, Killingly, CT 06239, 3 beds, 1 bath

$285,000

3 beds1 bath960 sq ft

37 Ruth St, Killingly, CT 06239

Property at 78 S Main St, Brooklyn, CT 06234, 6 beds, 2 baths

$400,000

6 beds2 baths2,652 sq ft

78 S Main St, Brooklyn, CT 06234

Property at 207 N Society Rd, Canterbury, CT 06331, 2 beds, 2 baths

$345,000

2 beds2 baths1,076 sq ft

207 N Society Rd, Canterbury, CT 06331

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

$266,999

6 beds2 baths2,600 sq ft

144 Prospect Ave, Killingly, CT 06239

Property at 260 Summit St, Willimantic, CT 06226, 9 beds, 4 baths

$479,000

9 beds4 baths2,939 sq ft

260 Summit St, Willimantic, CT 06226

Property at 232 Ballouville Rd, Dayville, CT 06241, 8 beds, 2 baths

$474,900

8 beds2 baths2,450 sq ft

232 Ballouville Rd, Dayville, CT 06241

Property at Undisclosed address, Plainfield, CT 06374, 4 beds, 2 baths

$459,900

4 beds2 baths2,400 sq ft

Undisclosed address, Plainfield, CT 06374

Property at 23 Mechanic St, Killingly, CT 06239, 5 beds, 3 baths

$450,000

5 beds3 baths2,032 sq ft

23 Mechanic St, Killingly, CT 06239

Property at 70 Walnut St, Putnam, CT 06260, 5 beds, 2 baths

$325,000

5 beds2 baths1,998 sq ft

70 Walnut St, Putnam, CT 06260

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

$520,000

4 beds3 baths2,150 sq ft

101 Child Hill Rd, Woodstock, CT 06281

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Vintage Homes for Sale in Windham County

There are currently 88 vintage homes for sale in Windham County at a median listing price of $400K. 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 37 days and receive 1 offers. This map is refreshed with the newest listings in Windham County every 15 minutes.

In the past month, 133 homes have been sold in Windham County. In addition to houses in Windham County, there were also 35 condos, 1 townhouse, and 42 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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