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415 Jerusalem Rd, Windham
$489,900
4 Beds ⋅ 3 Baths ⋅ 24195334 MLS
Pristine property with one floor living and enough room for all! Beautiful updated kitchen with breakfast bar, granite counters and access to the back deck perfect for all your gatherings by the pool or firepit. Amazing primary bedroom suite with hardwood floors, cathedral ceiling, sitting area, walk-in closet, full bath with whirlpool tub and access to your own private office. The remaining three bedrooms share a bathroom. A cozy den connects the primary bedroom to the large living room with fireplace and pellet stove insert. Bring your ideas to the lower level with its finished space with a half bath. The three car garage is heated and offers plenty of space for any projects. Close to an acre this beautifully landscaped lot offers vibrant colors and a peaceful setting.

415 Jerusalem Rd, Windham

21 Jack Henry Dr, Windham
$464,997
3 Beds ⋅ 3 Baths ⋅ 24207870 MLS
Welcome to this beautiful Colonial home, offering the perfect blend of classic charm, comfort, and space. Step inside to find gleaming hardwood floors and generously sized living areas filled with warmth and character. Spacious bedrooms provide plenty of room to relax and unwind, while the expansive living spaces offer a versatile layout ideal for both everyday living and entertaining. At the heart of the home is a beautiful, inviting kitchen featuring ample cabinetry, generous counter space, and plenty of room for gathering and entertaining. Whether preparing everyday meals or hosting family and friends, this welcoming space flows seamlessly with the rest of the home. Situated on an impressive lot of over two acres, the property offers exceptional privacy and an abundance of outdoor space to enjoy. Whether hosting summer gatherings, creating your own backyard retreat, or simply enjoying the peaceful surroundings, this expansive property provides endless possibilities. With its spacious interior, beautiful hardwood floors, inviting kitchen, and private setting, this Colonial is a wonderful place to call home.

21 Jack Henry Dr, Windham

7 Sycamore Ter, Windham
$399,000
5 Beds ⋅ 3 Baths ⋅ 24176079 MLS
Welcome Home to this beautifully updated 5-bedroom Colonial tucked away on a dead end road on a private, wooded .78-acre lot. Step inside to a sunlit living room where the fireplace sets the tone for cozy New England evenings, flowing seamlessly into the formal dining room and updated kitchen - ideal for hosting holidays or casual weeknight meals. Just off the main level, you will find a beautiful sun-filled room overlooking the backyard, great for entertaining, relaxing, or enjoying your morning coffee. A main-level office or fifth bedroom adds everyday flexibility. Upstairs offers four generously sized bedrooms and a full bath. Head to the finished, heated lower level that features natural light, walk-out access, a full bath, and ample space - offering incredible versatility for guests, a home office, extended living arrangements or potential in-law. Just a short distance to Shetucket Plains Road Park & Route 32.

7 Sycamore Ter, Windham

115 Chapman St, Windham
$375,000
6 Beds ⋅ 3 Baths ⋅ 24207512 MLS
Very well maintained 3 family in vibrant Willimantic. 3 Units plus a 3-car garage (extra cash flow) and 2 building lots (lots of space for parking outdoor activities). Roof replaced in 2023 and the property needs nothing. Unit 1 is a 1-bedroom. Tenant pays all utilities and rent is $1100. Unit 2 is vacant and is a 2 (maybe 3) bedroom. Owner pays gas heat. The unit has electric hot water heater (installed 2021) (electric paid by tenant). Rent is $1400. Unit 3 is a 3 bedroom. Owner pays gas heat. Electric hot water heater (installed 2021) (electric paid by tenant. Rent is $1300. 1 bay of garage is rented at $100/month. This is a great opportunity to live in a well maintained property and have your tenants help pay your mortgage. Or add this well maintained property to your investment portfolio.

115 Chapman St, Windham

371 Prospect St, Windham
$362,500
6 Beds ⋅ 2 Baths ⋅ 24200868 MLS
Whether you're looking for abundant living space, room for extended household members, or an investment opportunity, this spacious 5-bedroom, 2-bath home offers exceptional flexibility in a prime Windham location. The home features generously sized bedrooms, updated bathrooms, and a versatile floor plan that can easily adapt to a variety of needs. A possible sixth bedroom on the first floor provides even more options for a home office, guest room, or additional living space. Previously utilized as a 6-bedroom rental, the home offers an abundance of space and functionality. A detached 2-car garage and expansive driveway provide ample parking, while the generous .41-acre lot offers a surprisingly spacious yard with plenty of room to enjoy the outdoors. Located just steps from Eastern Connecticut State University and close to shopping, dining, and major commuter routes, this property combines space, convenience, and versatility in one unique package. Whether you're searching for a spacious primary residence or a property with strong income potential, this home is full of opportunity.

371 Prospect St, Windham

130 Windham Rd, Windham
$319,900
4 Beds ⋅ 3 Baths ⋅ 24198372 MLS
If you're looking for a spacious investment property or a home where you can add your own personal touches, this could be the one! Ideally located close to Eastern Connecticut State University, this 4-bedroom Colonial offers excellent potential as a housing investment, especially with a separate in-law apartment. The home features generously sized rooms, beautiful wood floors, some updated windows, and a cozy wood stove. Outside, enjoy a beautifully landscaped, fully fenced-in yard, a huge screened-in back porch-perfect for relaxing or entertaining-and a detached one-car garage. With its desirable location, flexible living space, and plenty of potential, this property is a wonderful opportunity for investors, owner-occupants, or anyone looking to create a home that truly reflects their style.

130 Windham Rd, Windham

41 Ashland St, Windham
$289,900
4 Beds ⋅ 2 Baths ⋅ 24202429 MLS
AT THE REQUEST OF THE SELLERS ALL HIGHEST AND BEST OFFERS TO BE SUBMITTED BY MONDAY SEPTEMBER 7, 2026 AT 8PM THANK YOU TO ALL WHO HAVE SHOWN THE PROPERTY AND HAVE SUBMITTED OFFERS Rare find kind of property! This property is complete with many incredible features. First Cape style home is 4 beds and 1.5 baths. Carpeted living room, first floor bedroom with a secondary bedroom that is currently being used as laundry room. Two additional rooms upstairs. Updated Galley style kitchen with granite countertops and plenty of cabinet space. Smaller eatin or informal dining area which leads into great room that looks out over the back yard. Oversized two car garage with lots of room for storage. All the mechanicals are updated including new furnace, electric hot water heater and oil tank. This home is equipped with a propane whole house generator. Your completely fenced in back yard is home to a screened in gazebo, a carefree detached garage, a storage shed and an unbelievable two story barn which has electric and insulated on lower level (WAIT until you see this barn!! Possible make it an ADU or second living space. THIS IS THE ONE YOU HAVE BEEN LOOKING FOR!!!! Priced to be VERY COMPETETIVE. Just a short walk to park springs or a little bit longer walk to center of town.

41 Ashland St, Windham

143 Southridge Dr, Windham
$289,000
3 Beds ⋅ 2 Baths ⋅ 24206582 MLS
Pride of ownership shines throughout this beautifully updated 3-bedroom, 1.1 bath ranch, ideally situated in a convenient neighborhood setting. The bright, freshly painted interior features gleaming hardwood floors, newer carpeting in all three bedrooms, freshly painted doors with updated hardware, custom window treatments, and stylish new lighting throughout. The updated kitchen offers newer tile flooring, refreshed countertops, a double sink, stainless steel appliances, plus a brand-new dishwasher and range hood (July 2026), making it as functional as it is attractive. Major improvements provide peace of mind, including a new roof (October 2024), central air conditioning, newer windows, and newer gutters with leaf guards. The heated lower level adds approximately 575 square feet of finished living space and includes a convenient half bath, creating the perfect space for a family room, home office, guest area, recreation room, or flexible everyday living. A separate laundry area is equipped with a newer washer and dryer. Step outside to enjoy a private backyard bordered by mature woods, offering a peaceful retreat for relaxing or entertaining. A storage shed provides additional space for lawn equipment, gardening tools, and seasonal storage, adding even more functionality to the property. Conveniently located near Routes 6 and 32, this home provides easy access to UConn, Eastern Connecticut State University, shopping, dining, and a variety of everyday amenities.

143 Southridge Dr, Windham

37 Mcdermott Ave, Windham
$250,000
3 Beds ⋅ 2 Baths ⋅ 24210539 MLS
Welcome to this charming 3-bedroom ranch offering convenient single-floor living in a quiet, established neighborhood. Bright, open rooms and ample storage add to the comfort of this home. Enjoy the beautiful new enclosed porch, perfect for relaxing or entertaining year-round. The large, open yard offers plenty of space for gardening, games, BBQs, or simply relaxing. The basement provides abundant storage, potential for future finished space, and a convenient walkout to a covered patio. Recent Updates include a repaved double-wide driveway, newer appliances, a chimney rebuilt in 2020, and a furnace and oil tank replaced in 2019. Solar adds energy efficiency and savings potential. Conveniently located near shopping, dining, UCONN, Eastern CT State University, Electric Boat, and the nearby casinos, with easy access for commuters. Schedule your private tour today!

37 Mcdermott Ave, Windham

129 Valley St, Windham
$250,000
7 Beds ⋅ 4 Baths ⋅ 24138836 MLS
Mixed-use investment property with multiple income streams and strong value-add potential. The property is zoned B-1A and currently configured with two occupied residential units generating income, plus two additional gutted residential units with plumbing in place, ready for build-out. The property also includes a commercial storefront with a separate entrance, offering flexibility for a variety of permitted uses. B-1A zoning may allow for additional residential units, subject to municipal approvals. Additional income opportunities include four dedicated storage spaces, ideal for ECSU students or nearby tenants, two garage bays, and an on-site parking lot, all of which convey with the property. Property is being sold as-is.

129 Valley St, Windham

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