South Windham, CT homes for sale & real estate

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3D WALKTHROUGH

34 S Windham Rd, Windham, CT 06226
34 S Windham Rd, Windham, CT 06226
34 S Windham Rd, Windham, CT 06226
ABOUT THIS HOME
South Windham, CT Homes for Sale
Welcome to 34 South Windham Road! Whether you're a first-time homebuyer or looking to downsize, this charming, well-maintained home is move-in ready and full of thoughtful updates. Step inside to find new flooring in the living room and bedrooms, a fresh coat of paint throughout, a new roof and boiler, and a recently updated rug in the spacious downstairs extra room. The lower level features a fully finished family/rec room with a closet-ideal for relaxing, entertaining, or even a guest space. Outside, enjoy your morning coffee or evening unwind on the cozy front patio. Every detail has been handled with care and pride, making this home truly turn-key. Be sure to check out the photos and vi

$244,900

3 beds1 bath1,156 sq ft

34 S Windham Rd, Windham, CT 06226

0.75 acre lot • Car-dependent

33 Machine Shop Hill Rd, Windham, CT 06266
ABOUT THIS HOME
South Windham, CT Homes for Sale
Welcome to a unique chance to own a spacious multi-family property in the charming South Windham area. This home presents an outstanding opportunity for investors seeking rental income and invites a creative new owner to explore the renovation potential. With a total of five bedrooms and two bathrooms spread across 2,548 square feet, this property is ideal for offering flexibility to operate as a side-by-side duplex or be converted to a single-family residence. Each unit features its own living space, making it suitable for an owner-occupant with rental plans or a full investment property. The basement offers additional storage or workshop options. The versatile layout also includes covered

$237,500

5 beds1 bath2,548 sq ft

33 Machine Shop Hill Rd, Windham, CT 06266

0.42 acre lot • Garage • Car-dependent

4 Main St, Windham, CT 06226
4 Main St, Windham, CT 06226
4 Main St, Windham, CT 06226
ABOUT THIS HOME
South Windham, CT Homes for Sale
Terrific Investment Opportunity! Don't miss this rare chance to own a well-maintained multi-unit property with strong income potential. The main house features a spacious layout with 5 bedrooms, ideal for large households or rental flexibility. Behind the main home, you'll find a separate 2-bedroom unit, perfect for extended family or additional rental income. Additionally, there's a third unit-a charming ranch-style 2-bedroom apartment located above a detached 3-car garage. Key features include: Whole-house generator for the main home. Newer boiler and hot water heater. New roof. Plenty of off-street parking. Whether you're a seasoned investor or just getting started, this property is a fa

$485,000

8 beds3.5 baths5,134 sq ft

4 Main St, Windham, CT 06226

1.54 acre lot • 3 garage spots • Car-dependent

270 S Windham Rd Apt 63, Windham, CT 06226
270 S Windham Rd Apt 63, Windham, CT 06226
270 S Windham Rd Apt 63, Windham, CT 06226
ABOUT THIS HOME
South Windham, CT Homes for Sale
Welcome to 270 S Windham Road in Willimantic, CT! This beautifully updated first-level condo offers the perfect blend of comfort and convenience. Ideal for first-time buyers, downsizers, or investors, this well-maintained unit features modern finishes and a thoughtfully designed layout. Step inside to discover a bright, freshly painted living space with newer flooring and stylish updated fixtures. The open-concept living and dining areas provide a seamless flow for entertaining, while the in-unit laundry adds everyday convenience. Enjoy easy access to both Mohegan Sun and Foxwoods casinos, as well as Eastern Connecticut State University and UConn. Plus, the charming Windham Center is just a

$127,500

2 beds1 bath790 sq ft

270 S Windham Rd Apt 63, Windham, CT 06226

$455 HOA • Car-dependent

337 S Windham Rd, Windham, CT 06226
337 S Windham Rd, Windham, CT 06226
337 S Windham Rd, Windham, CT 06226
ABOUT THIS HOME
South Windham, CT Homes for Sale
Step into timeless elegance with this beautifully renovated 1850 Colonial, now featuring a brand new septic tank and central A/C system installed in April 2025-a perfect blend of historic charm and modern comfort. Nestled in the heart of Windham, this stunning 9-room home has 4 spacious bedrooms and 2.1 bathrooms, providing ample space for today's lifestyle. Inside, you'll find brand-new kitchens and bathrooms thoughtfully designed with contemporary finishes while preserving the home's classic character. Gleaming hardwood floors flow throughout, adding warmth and sophistication to every room. Whether you're entertaining in the bright, open living areas or enjoying quiet moments on the pictu

$437,000

4 beds2.5 baths2,905 sq ft

337 S Windham Rd, Windham, CT 06226

0.3 acre lot • Car-dependent

Property at 1157 Windham Rd, Windham, CT 06266, 3 beds, 2 baths

$441,750

3 beds2 baths1,400 sq ft

1157 Windham Rd, Windham, CT 06266

Property at 1145 Windham Rd, Windham, CT 06266, 3 beds, 2.5 baths

$459,000

3 beds2.5 baths1,900 sq ft

1145 Windham Rd, Windham, CT 06266

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122 Lovers Ln, Windham, CT 06280
122 Lovers Ln, Windham, CT 06280
122 Lovers Ln, Windham, CT 06280
ABOUT THIS HOME
South Windham, CT Homes for Sale
Nestled on a just under 2 acre lot in Windham, this refreshed home offers a tranquil retreat surrounded by nature. Step inside to discover a welcoming interior, spanning 1,736 square feet, with 4 bedrooms and 2 full bathrooms. The property boasts modern comforts while retaining its charming character. Beyond the thoughtfully placed living spaces, the true highlight of this property is its exceptional natural setting. The expansive 1.75 acres provide ample space for outdoor enjoyment, with wooded and treed areas creating a private oasis. For the outdoor enthusiast, this location is a dream. You'll enjoy the convenience of being within walking distance to Potash Brook and its scenic dam, offe

$335,000

4 beds2 baths1,680 sq ft

122 Lovers Ln, Windham, CT 06280

1.75 acre lot • Car-dependent

208 Kick Hill Rd, Lebanon, CT 06249
208 Kick Hill Rd, Lebanon, CT 06249
208 Kick Hill Rd, Lebanon, CT 06249
ABOUT THIS HOME
South Windham, CT Homes for Sale
A Rare Gem on 25 Acres - Timeless Charm Meets Thoughtful Updates This absolutely stunning antique home sits on 25 acres of picturesque land-a truly rare find. Lovingly maintained and thoughtfully updated over the past 33 years, the home features Marvin window additions, a roof installed just 7 years ago, and beautifully renovated kitchen and baths-all while preserving the timeless charm and character that make this home so special. Recent upgrades include a new hot water heater installed in 2021, as well as central air conditioning and forced hot air heating for year-round comfort. Step out back to discover a spacious structure boasting a massive brick wood-burning fireplace that spans an e

$450,000

3 beds2 baths1,629 sq ft

208 Kick Hill Rd, Lebanon, CT 06249

25.06 acre lot • Car-dependent

20 Greystone St, Windham, CT 06226
20 Greystone St, Windham, CT 06226
20 Greystone St, Windham, CT 06226
ABOUT THIS HOME
South Windham, CT Homes for Sale
Fully renovated 3 bedroom, 1 1/2 Bathrooms on a level lot. Updated plumbing, electrical, insulation, furnace, water heater, roof, appliances, kitchen, all new windows and framed in basement ready for completion to add additional bedrooms or space. All public utilities. Dont miss your chance to see this move in ready home !

$274,900

3 beds1.5 baths1,344 sq ft

20 Greystone St, Windham, CT 06226

0.23 acre lot • 2 garage spots • Car-dependent

434 Pleasant St, Windham, CT 06226
434 Pleasant St, Windham, CT 06226
434 Pleasant St, Windham, CT 06226
ABOUT THIS HOME
South Windham, CT Homes for Sale
This 2 story multi-family gem offers two spacious 2-bedroom, 1-bath units (approx. 1,100 sq ft each), one upstairs and one downstairs-both currently leased by long-term tenants with separate utilities, providing hassle-free rental income. Many upgrades have already been done here. Schedule a showing for a better look of this property. Check agent remarks

$235,000

4 beds2 baths2,259 sq ft

434 Pleasant St, Windham, CT 06226

5,227 sq ft lot • Very walkable

389 Pleasant St, Windham, CT 06226
389 Pleasant St, Windham, CT 06226
389 Pleasant St, Windham, CT 06226
ABOUT THIS HOME
South Windham, CT Homes for Sale
Prime Investment Opportunity in Willimantic! Excellent potential in a high-demand, low vacancy location. With strong bones, proximity to ECSU, public transit and downtown this property is perfect for investors or house hackers looking to build equity fast. NEW ELECTRIC PANELS, NEW HEAT AND HOT WATER FURNACES. Combine with other listed Willimantic properties: Elm st. , Jackson St. , and Chapman St. as a 17 unit portfolio. GOI:63,000 Expenses: 10,868 NOI: 52,132 10CAP PRO Forma NOI: 77,932!!! floor plans available * *

$489,999

8 beds4 baths3,828 sq ft

389 Pleasant St, Windham, CT 06226

0.32 acre lot • Very walkable

57 Chapman St, Windham, CT 06226
57 Chapman St, Windham, CT 06226
57 Chapman St, Windham, CT 06226
ABOUT THIS HOME
South Windham, CT Homes for Sale
Don't miss this exceptional investment opportunity at 57 Chapman Street in Willimantic, CT! This versatile 3-family property features one spacious 3-bedroom, 1-bath unit and two well-proportioned 2-bedroom, 1-bath units, making it an ideal choice for investors or owner-occupants seeking rental income. Each unit offers comfortable layouts with ample potential for updates and customization, allowing you to increase long-term value and cash flow. The property is situated in a convenient location close to shopping, dining, schools, parks, and public transportation, making it attractive to a wide range of tenants. Whether you're expanding your portfolio or looking to live in one unit while renti

$179,925

7 beds3 baths2,668 sq ft

57 Chapman St, Windham, CT 06226

6,534 sq ft lot • Somewhat walkable

Property at 100 South St, Windham, CT 06226, 6 beds, 2 baths

$299,000

6 beds2 baths1,932 sq ft

100 South St, Windham, CT 06226

Property at 96 South St, Windham, CT 06226, 6 beds, 2 baths

$289,000

6 beds2 baths1,736 sq ft

96 South St, Windham, CT 06226

Property at 87 North St, Windham, CT 06226, 6 beds, 2 baths

$320,000

6 beds2 baths2,981 sq ft

87 North St, Windham, CT 06226

Property at 38 Elm St, Windham, CT 06226

$99,900

— beds— baths— sq ft

38 Elm St, Windham, CT 06226

Average home prices near South Windham, CT

Cities

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$384,950
East Hampton homes for sale
$399,900
Manchester homes for sale
$329,900
Willimantic homes for sale
$276,450
Baltic homes for sale
$464,900
Brooklyn homes for sale
$432,450
Stafford Springs homes for sale
$375,000
Gales Ferry homes for sale
$380,000
Danielson homes for sale
$499,900
Rockville homes for sale
$312,450
Moodus homes for sale
$349,900
Norwich homes for sale
$296,950
Moosup homes for sale
$439,000

Zip Codes
Minor Civil Divisions

South Windham, CT real estate trends

$360K

Sale price

+101.1%
since last year

$181

Sale $/sq ft

-8.1%
since last year

Over list price

2.3%

Days on market

Down payment

—

Total homes sold

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