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55 Main St, Windham
$299,000
4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24216737 MLS
Investors Take Notice! Bring your vision and unlock the potential of this Victorian-style two-family property at 55 Main Street in Willimantic. Each unit offers 2 bedrooms and 1 bath, with both bathrooms recently updated with brand-new finishes. While the property would benefit from additional updating and improvements, the opportunity to build equity and maximize its potential is well worth exploring. Ideally located across from Recreation Park, near Eastern Connecticut State University and UConn, and within walking distance to local amenities and the bus line. Whether you're an investor seeking your next project or an owner-occupant looking to offset your mortgage with rental income, this property offers exciting possibilities. Bring your ideas, envision the possibilities, and schedule your showing today!

55 Main St, Windham

207 Summit St, Windham
$329,900
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24216414 MLS
Step into a truly one-of-a-kind home where history, character, and creativity come together. Originally built circa 1892 as the historic Hilltop Hose Company No. 3 Firehouse, this remarkable property has been thoughtfully transformed into an eclectic single-family residence while honoring its architectural roots. The 1,000-square-foot first floor offers an expansive open layout with soaring ceilings, creating an impressive space for everyday living and entertaining. Nearly as spacious, the versatile third-floor retreat includes a full bathroom, extensive built-in storage, counter space, and a private balcony-making it ideal as a generous primary suite, guest room, living area, home office, creative studio, or flexible multigenerational living space. Distinctive Art Deco-inspired design elements add personality throughout, creating a home unlike any other. The composite and stone patio, landscaped yard, and the refreshing shade of mature trees make it an ideal spot to enjoy your morning coffee or unwind at the end of the day. The impressive stone foundation basement boasts high ceilings, a laundry area with utility sink, and clean storage space. Conveniently located near Eastern Connecticut State University, downtown Willimantic's restaurants, shops, entertainment, and local events, with easy access to Route 6 and a short drive to UConn. A rare opportunity to own a distinctive property where historic charm and modern comfort blend into an unforgettable place to call home.

207 Summit St, Windham

106 Jerusalem Rd, Windham
$389,000
3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24216131 MLS
Pride of ownership shines throughout this beautifully maintained circa 1953 Ranch, nestled on 1.38 acres of picturesque, park-like grounds! Quality built and lovingly cared for, this inviting 3-bedroom, 1-bath home offers comfortable one-level living with timeless charm and thoughtful updates. Inside, discover gleaming hardwood floors, a spacious living room with fireplace, adjoining dining area, and a bright kitchen featuring natural wood cabinetry and ample storage. A true highlight is the expansive 48'x17' 3-season sunroom, surrounded by windows and sliders offering wonderful views of the beautifully landscaped grounds. Perfect for relaxing, entertaining, or simply enjoying nature's changing seasons! Outside, sweeping lawns, mature trees, ornamental plantings, and lovely garden areas create a peaceful retreat. A covered patio, two storage sheds, paved driveway, and attached 2-car garage add convenience and versatility. Significant improvements include the roof, windows, sliders, updated electrical, mini-split systems, and a new boiler. Central air and a generator hookup provide additional comfort and convenience. A wonderful combination of solid construction, meticulous maintenance, and natural beauty, this special property is ready for its next chapter. Come experience it for yourself! Owner is a licensed real estate agent in VT.

106 Jerusalem Rd, Windham

33 Old Brooklyn Tpke, Windham
$365,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24215945 MLS
Country living at its best with this Contemporary Cape w/1711sqft, 3 Bedrm, 3 Full Baths, HUGE 1000 plus sqft BARN/GARAGE/OUTBUILDING ON 2.64 ac of level land with a stream. Perfect property for hobbys, animals, storage, wood working, home based business and much more. Open floor plan w/ 2 Foyer entrances w/ tiles floors, open kitchen & dining rm with slider to your private deck. Living rm with a woodstove. 1st floor large bedrm w/ full bath with tile floor & adorable barn doors. 2nd floor has a Master suite w/ Full bath w/a jacuzzi tub. 2nd master bed w/vaulted ceilings & french doors to a private deck. Separate office, play rm or could be a large walkin closet & a 3rd FULL BATH. BARN/OUT BUILDING/ GARAGE w/ a full attic floored. So many possibilities in this home. Bring your horses, home based business, 4 wheelers, dirt bike, green house, storage, man cave, garage, chicken coop & so much MORE. Sits privately off the road with lots of space for gardens on a nice level lot. Many updates throughout the years including windows, roof, septic tank, well tank & much more. Solar panels to save money on power. Power bill is approx 80 dollars a month. Sits on a dead end street. Come live in the country close to all major routes, airport, Hartford, cssinos for ONLY 365,000

33 Old Brooklyn Tpke, Windham

33 Machine Shop Hill Rd, Windham
$519,900
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24215433 MLS
Beautifully Remodeled Home with Modern Updates & Separate In-Law Living! Welcome to this beautifully renovated home offering the perfect combination of modern comfort, spacious living, and versatility! Thoughtfully updated throughout, this home features an inviting layout designed for today's lifestyle. The main living area offers 3 spacious bedrooms, 2.5 bathrooms, and a dedicated home office. The bright, open-concept kitchen, dining, and living areas create a seamless flow, perfect for everyday living and entertaining. Convenient main-level laundry adds to the home's functionality. A separate in-law living area provides an excellent opportunity for multigenerational living, extended family, or guests. This private space features 1 bedroom, 1 full bathroom, its own laundry area, and a comfortable living space, all conveniently located on the first floor. Extensive renovations throughout, including a new roof and new furnace, offer added value and peace of mind. Step outside to enjoy the spacious deck, ideal for outdoor entertaining, relaxing, or hosting summer gatherings. The property also features two detached garages, including an oversized heated garage offering exceptional space for vehicles, storage, a workshop, or hobbies. With its beautifully updated interior, flexible living arrangements, and impressive garage space, this property offers something for everyone. Move-in ready and full of possibilities-schedule your private showing today!

33 Machine Shop Hill Rd, Windham

15 Cracow Ave, Windham
$324,999
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24214512 MLS
Imagine summer mornings with coffee on the new Trex deck, afternoons spent by your in-ground pool, and evenings launching a kayak right into the river behind your backyard. At 15 Cracow Ave, that lifestyle comes together with the comfort of an updated 3-bedroom, 2-bath ranch where many of the big-ticket improvements have already been taken care of. Inside, the open floor plan was made for gathering. The remodeled kitchen features quartz countertops and soft-close cabinetry and opens directly into the dining area and spacious living room, where a wood-burning fireplace becomes the centerpiece on cooler New England nights. Down the hall, the true primary suite gives you something rarely found at this price point-a private full bathroom with double vanities-along with two additional bedrooms and a second full bath.

15 Cracow Ave, Windham

303 Boston Post Rd, Windham
$495,000
ACTIVE Status ⋅ 24215007 MLS
303 Boston Post Road, North Windham, CT, offers a compelling opportunity to acquire a high-visibility commercial property along the Route 6 retail corridor at a lighted corner. Priced at $495,000, this single-story brick/masonry building features approximately 1,500 SF on the first floor plus a 1,500 SF basement, providing flexibility for office, service, or adaptive-reuse potential. Surrounded by major national retailers including Walmart, The Home Depot, Tractor Supply Co., and Dunkin', the property benefits from strong commercial synergy and daily exposure along a corridor with approximately 16,900 vehicles per day. The site is well positioned for users seeking an established location with existing improvements, public water and sewer, and strong visibility in one of North Windham's primary retail areas. This property also presents an exciting value-add or redevelopment angle, with potential to explore a compact coffee or quick-service concept, subject to approvals.

303 Boston Post Rd, Windham

129 Walnut St, Windham
$217,500
4 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24213182 MLS
Charming Antique Colonial - Prime Windham Location Step back in time and experience the warmth and character of this classic 1915 Antique Colonial, beautifully situated on a desirable corner lot in Windham. This inviting home offers four spacious bedrooms and one full bath, along with a generously sized living room perfect for relaxing or entertaining. The bright eat-in kitchen provides a welcoming space for gatherings and everyday living. Enjoy peaceful mornings or cozy seasonal evenings in the sun-filled three-season room, complete with stairs leading directly out to the backyard. The property is surrounded by a charming white picket fence, enhancing its timeless New England appeal. A standout feature is the impressive two-story garage with access from two streets, offering exceptional convenience, storage, or potential workshop space. The full walk-out lower level adds additional functionality and flexibility. Ideally located close to local colleges, this property presents an excellent opportunity for investors, owner-occupants, or those seeking rental potential. Enjoy nearby delicious eateries, unique shops, and easy commuting access to surrounding towns and major routes. This is a truly charming and classic New England home that must be seen to be fully appreciated.

129 Walnut St, Windham

154 Manners Ave, Windham
$288,000
3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24210578 MLS
Welcome to this well-cared-for home, where thoughtful updates and a comfortable layout create an inviting place to call home. The spacious eat-in kitchen provides plenty of room for meals and entertaining and flows naturally into the living area. The home offers three bedrooms and a well-maintained bathroom. A full walkout basement provides excellent potential space, whether you need a recreation room, home office or workshop. Outside, you'll find a private deck, paved driveway, an a carport for convenient parking and outdoor enjoyment. The roof was newly installed in September 2026, providing an important recent improvement for the next owner. With its comfortable floor plan, outdoor amenities, and opportunity to expand, this home offers plenty of room to make it your own. Situated in a peaceful and desirable part of town, the property is also conveniently located near UConn and Eastern Connecticut State University.

154 Manners Ave, Windham

19 Bellevue St, Windham
$349,900
5 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24210038 MLS
Spacious two-family home offering 5 bedrooms, 2 baths, a large basement, detached garage, covered front porch, and flexible space throughout. Great opportunity for an owner-occupant or investor. Unit 1 offers approximately 1,453 sq. ft. with 3 bedrooms and 1 full bath. The first floor features a large bedroom, spacious living room, kitchen, and full bath, with two additional bedrooms upstairs. The unit also has access to an approximately 1,201 sq. ft. unfinished basement with washer and dryer and plenty of storage space. Unit 2 offers approximately 1,026 sq. ft. with 2 bedrooms and a 3/4 bath. It includes a living room, kitchen, large bedroom with balcony, second bedroom, and approximately 216 sq. ft. of additional attic/storage space on the third floor. The property also includes a 462 sq. ft. detached garage and off-street parking. Convenient opportunity to live in one unit while renting the other, or add a two-family property to your investment portfolio. Furniture shown in the photos can be included with the sale at no additional cost.

19 Bellevue St, Windham

349 Mansfield Ave, Windham
$299,900
3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24201525 MLS
A delightful gem of a home, this Cape is set in the heart of Willimantic. This home offers easy access to town, shopping, and commuting routes. A charming, move-in-ready opportunity is updated and ready for its next owner, with an open-air plan and unique, tasteful finishing touches throughout. Fresh, modern updates within the last 4 years include: kitchen with granite counters and new stainless appliances (oven/range, microwave, range hood, refrigerator, dishwasher), first-floor bath, carpet in the upstairs bedrooms, newer vinyl siding, windows, roof, and furnace, 3-zone heat for comfort and efficiency. First-floor primary bedroom - easy single-level living, first-floor laundry in the expansive four-season sunroom, sunroom opens to a deck overlooking a very private backyard with stone walls, 3 bedrooms, 1 full bath, 6 rooms total, original wood panel interior doors; updated insulated exterior doors. Added features include, connected Bluetooth speaker in the shower, electric fireplace insert and, under-house 1-car garage plus private driveway (4 parking spaces) and Solar - schedule your tour today!

349 Mansfield Ave, Windham

29 James Dr, Windham
$82,900
2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24204985 MLS
Welcome to this well-maintained 2-bedroom, 2-full-bath mobile home located in Stonegate Manor, offering a comfortable and functional floor plan. The primary bedroom features a private full bath and walk-in closet, while the two bedrooms are thoughtfully situated at opposite ends of the home for added privacy. The fully applianced kitchen includes a convenient snack bar, with a dedicated laundry area down the hall. Enjoy the added comfort of Central Air Conditioning throughout the home. A newer roof (2021) and updated windows adds peace of mind, while the 12x12 roofed deck provides a great space for relaxing. A storage shed adds additional convenience. While the home retains some original finishes, it has been well cared for, is clean, and move-in ready. Conveniently located near shopping, restaurants, gas stations, and other everyday amenities, this home offers comfortable living in a convenient location. Park approval is required. Monthly park fee is $769

29 James Dr, Windham

120 North St, Windham
$634,900
10 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24204552 MLS
Income producing multi family property offering a strong opportunity for investors or owner occupants alike. One unit is currently not leased, providing immediate leasing potential or flexibility for owner occupancy. Property presents the opportunity to generate rental income with additional upside potential over time. Detached garage offers added utility with potential for storage, workshop space, or future supplemental income opportunities. Conveniently located near Eastern Connecticut State University, downtown Willimantic, shopping, dining, and major commuter routes. Great opportunity to add a multifamily asset to an investment portfolio. One of the parties to the LLC has an active real estate license.

120 North St, Windham

86 Chestnut St, Windham
$290,000
4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24201649 MLS
INVESTOR OPPORTUNITY IN WILLIMANTIC! Bring your vision to 86 Chestnut Street, an approximately 1,560 SF multifamily property. Originally built in 1887, the property offers timeless architectural character and charm rarely found in newer construction. Conveniently located near downtown Willimantic, Eastern Connecticut State University, shops, restaurants, services, and major area routes. Offered AS-IS, providing an opportunity to renovate and customize to your investment strategy. The property's character, layout, location, and value-add potential make this an excellent opportunity for an investor or owner-occupant. Cash or conventional financing only. No government financing. Buyer to conduct their own due diligence regarding condition, zoning, intended use, and renovation potential.

86 Chestnut St, Windham

11 Bellevue St, Windham
$145,000
6 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24201036 MLS
Bring your vision to this six-bedroom home in Willimantic's Hill Section. With approximately 1,948 square feet of living space, the property features generously sized rooms, hardwood flooring, tall windows, original woodwork, and period details throughout. A brand-new roof has already been installed, providing a great start for future improvements. With thoughtful updates, this home has the potential to showcase its original character while being tailored to its next owner. Conveniently located near downtown Willimantic, Eastern Connecticut State University, shopping, dining, and major routes. Property is being sold as-is. Also available is 15 Bellevue Street, located at the front of the property, creating the possibility of a package purchase. One of the parties to the LLC has an active real estate license.

11 Bellevue St, Windham

350 Tuckie Rd, Windham
$1,149,000
4 Baths ⋅ ACTIVE Status ⋅ 24197138 MLS
Rare income-producing industrial/residential combination (sold as a package) on 3.41 acres in North Windham, CT, conveniently located right off Rt6. The offering includes an active concrete casting and precast manufacturing campus at 350 Tuckie Road, comprised of two buildings totaling 13,800 SF: a 9,800 SF two-story main plant built in 1965 with 21' wall height, and a 4,000 SF warehouse built in 2002 with 15' wall height, currently leased to a metal fabrication tenant. Casting equipment and forms convey with the sale, offering a turnkey opportunity for an owner to continue precast operations, while additional site equipment, vehicles, and machinery may be available separately. The adjoining residential parcel at 356 Tuckie Road provides road frontage and a buffer to the industrial campus, and includes a 1,052 SF, 2-bedroom, 1-bath ranch-style residence with a 308 SF garage - ideal for an owner-operator or on-site foreman/employee, or currently rented month-to-month for immediate income. Both parcels share a private well and septic system and are offered together as one. Combined in-place gross rental income totals approximately $33,600/year. This gives the new owner the flexibility to occupy, re-lease, or formalize a new lease at closing. Estimated market rent range for the combined property is $5.000+/month. Zoned C1 (industrial) and PDD1 (residential), this is an excellent opportunity for an owner-operator, investor, or precast manufacturer!

350 Tuckie Rd, Windham

260 Summit St, Windham
$479,000
9 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24185574 MLS
Opportunity awaits with this multi-family property in Willimantic. Featuring multiple residential units with a mix of layouts, this property offers flexibility for both investors and owner-occupants seeking rental income. Conveniently located near Eastern Connecticut State University, shopping, restaurants, parks, public transportation, and major commuter routes. Separate living spaces provide privacy for occupants while the property's central location adds to its long-term appeal. Whether you're looking to expand your investment portfolio or offset your housing costs with rental income, this property presents a versatile opportunity in a convenient location. One of the parties to the LLC has an active real estate license.

260 Summit St, Windham

45 Whittemore St, Windham
$374,900
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24184708 MLS
Welcome home to this lovingly maintained 3-bedroom, 2-bath Ranch set on nearly half an acre in Willimantic. A welcoming slate-tiled foyer leads into a spacious living room that flows seamlessly into the dining area, creating a bright and inviting space filled with natural light. The eat-in kitchen features warm wood cabinetry, granite countertops, and ample workspace for meal preparation. Step outside to the composite deck overlooking the fenced backyard, perfect for relaxing, entertaining, gardening, or play. The home offers a primary suite with a private bath and two additional bedrooms. Laundry is currently located in the third bedroom but can easily be relocated to the basement, where washer and dryer hookups already exist. The walkout lower level is unfinished and offers endless possibilities for future expansion, including additional living space, a home office, gym, or potential in-law setup. Additional features include a spacious two-car garage with storage, central air, a boiler and heat pumps for efficient heating and cooling. Move right in and make it your own!

45 Whittemore St, Windham

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