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37 Manners Ave, Windham
$550,000
8 Beds ⋅ 5 Baths ⋅ 24176666 MLS
HIGHEST and BEST due midnight 6/8. What if your next investment came with an indoor pool and was completely furnished? 37 Manners Ave is not your average multifamily. This custom-built 3-family sits on a spacious lot in Willimantic with additional finished spaces, giving owners over 4,800 square feet to work with. Two 2-car garages, a spacious yard, a wide patio, and a private indoor pool with cathedral wood-beam ceilings and skylights that round out this property that makes this THE special opportunity you've been dreaming of. And, the numbers work great. At market rent this property projects strong monthly cash flow and an appealing cap rate from day one. All total expenses were only $23k last year. Plus, the location just couldn't be better. Minutes from UConn, ECSU, Foxwoods, and Mohegan Sun. And the best part? It's walkable to downtown Willimantic and all of it's parks, restaurants, community center, concerts on the green, and 3rd Thursday Street Festivals. Whether you are a Multigenerational family looking for a space for everyone, a Hospitality entrepreneur ready to host experiences unlike any other, or a buy-and-hold investor that wants to live large while you grow your portfolio, 37 Manners Ave is the perfect pen with which to write your next chapter. This property has the space, the income, and the wow factor to make it all real. They say you only live once. Get the pool

37 Manners Ave, Windham

74 Pigeon Rd, Windham
$435,000
4 Beds ⋅ 3 Baths ⋅ 24172139 MLS
This is the one you've been waiting for! Offered for the first time in 38 years, this lovingly maintained home blends thoughtful updates with charming retro touches - welcome to 74 Pigeon Road! Filled with natural light, the sprawling layout features 4 bedrooms, including a sunken primary suite with walk-in closet on the second floor, and 2.5 baths. The updated kitchen is a total standout, complete with a breakfast nook, while the first floor also offers a formal dining room, spacious office, convenient laundry, living room, and a sunken family room perfect for relaxing or entertaining. Enjoy additional highlights like central vacuum, a newer roof and boiler, newly paved driveway, and a finished lower level ideal for a rec room, hobby, or workshop space. Unwind year-round in the dedicated hot tub room, or step outside to a beautiful stone patio overlooking the manicured yard. Set on a cul-de-sac street in an established neighborhood, this property offers a convenient location that is walkable to downtown where you'll find local shops, dining, and entertainment, and with easy access to nearby ECSU and major routes, and just 15 minutes from UConn. A rare opportunity to own a very well-cared-for home with space, character, and versatility.

74 Pigeon Rd, Windham

272 Prospect St, Windham
$420,750
5 Beds ⋅ 3 Baths ⋅ 24179602 MLS
Step back in time in this majestic REMODELED 5-Bedroom Queen Anne-style Victorian home complete with wrap-around porch, gorgeous stone pathway gardens, soaring ceilings, hardwood floors, original woodwork, AND a beautifully remodeled kitchen!! The George Tiffany House circa 1890 offers plenty of rich history and architectural character and is on the National Registery of Historic Places. The interior has been lovingly updated/restored over the past 3 years, while preserving the special character of this gorgeous home. All antique windows have been reglazed and have storm windows for energy efficiency. Steam radiator heat with natural gas boiler. The huge walk-up partially-finished attic could be easily completed and made into a wonderful artist space or rec/game area. And for those who are looking for a workshop...There are TWO large connected rooms in the basement with tall ceilings for your woodworking or hobby pleasure, in addition to other storage space accessible from both inside the home and though the back garage bay. Excellent location to ECSU and restaurants and amenities downtown. Come see what this beautiful home has to offer!! Additional photos to follow.

272 Prospect St, Windham

4 Aspen Pl, Windham
$413,000
3 Beds ⋅ 2 Baths ⋅ 24197724 MLS
Welcome to this beautifully maintained ranch home offering true one level living and peace of mind with major recent updates, including a newer central air system and convenient efficient propane heating system for reliable year-round comfort. Clean, functional, and easy to navigate, this home is ideal for buyers seeking a low maintenance lifestyle or planning ahead for aging in place. Situated in a desirable residential neighborhood with no HOA fees, this move in ready property is designed for long term convenience. The expansive backyard provides plenty of usable outdoor space for gardening, pets, play, or future outdoor entertaining. Inside, you'll find a bright and inviting interior with a practical open concept layout. The spacious kitchen serves as the heart of the home, flowing seamlessly into both the dining area and living room, creating an ideal space for everyday living and gatherings. The attached one car garage offers easy access to the kitchen, making unloading groceries effortless, while also providing a convenient mudroom area and laundry space with convenient laundry space. The formal front entry welcomes you with unobstructed views of the main living area, enhancing the home's spacious feel. Two bedrooms and a full bath are located on one side of the home, while the private primary suite occupies the opposite wing, featuring a generous walk-in closet and large full bath.

4 Aspen Pl, Windham

66 Lynwood Dr, Windham
$410,000
3 Beds ⋅ 2 Baths ⋅ 24175279 MLS
Welcome to this ranch home in excellent condition offering true one level living and worry free with a new HVAC system for heat and central air, as well as a new hot water heater - both for efficient and reliable comfort. The home is clean, functional, and easy to navigate - perfect for buyers seeking a low maintenance lifestyle or planning ahead for aging in place. Located in a residential area with no HOA fees, this property is move in ready and designed for long term convenience. An expansive backyard allows for plenty of usable outdoor space for gardening, pets, and play. Inside, you'll find a bright, clean interior with a practical flow. The heart of the home features an open concept where the large kitchen is open to both the dining area and living room. Bringing in groceries from the attached 1-car garage is a breeze with just a few steps into the kitchen. This everyday entry also provides a mudroom area and laundry (new units installed in 2025). The formal front door entry gives a spacious feel when entering with unobstructed views of the main living area. To the left are two bedrooms and full bath in between. On the other side of the home is a primary bedroom suite complete with a roomy walk-in closet and large full bath. The walkout lower level is a bonus surprise. A glass slider and two full-sized windows brighten up this level offering future expansion capabilities (possible in-law/apartment). Currently being used for a second laundry area and storage.

66 Lynwood Dr, Windham

21 Lewiston Ave, Windham
$385,000
8 Beds ⋅ 3 Baths ⋅ 24166161 MLS
Discover the perfect blend of owner-occupant comfort and income-generating potential at 21 Lewiston Ave. This versatile property is an ideal house hack opportunity, offering Unit 1 in true move-in condition-perfect for an end user looking to offset their living expenses or an investor seeking to maximize cash flow from day one. Unit 1 has been thoughtfully maintained and is essentially turnkey, allowing for immediate occupancy without the need for renovations or updates. Whether you choose to live in the unit yourself or place a tenant at market rent, the flexibility here is unmatched. The layout is functional and inviting, appealing to a wide range of tenants and ensuring strong, consistent demand. This property presents a rare chance to create a "cash cow" scenario: live affordably while rental income from additional units helps cover your mortgage-or fully lease the building and enjoy steady passive income. With minimal upfront work required, you can focus on optimizing rents and building equity from the start. Additional highlights include solid mechanicals, a well-kept interior, and the kind of low-maintenance condition that both homeowners and tenants appreciate. Opportunities like this-where a property is both livable and income-producing without heavy lifting-don't come around often.

21 Lewiston Ave, Windham

27 Aspen Pl, Windham
$375,000
5 Beds ⋅ 3 Baths ⋅ 24141219 MLS
Welcome to 27 Aspen Place, a well maintained raised ranch built in 2005, offering comfort, space, and convenience. This home features 5 spacious bedrooms, including a Primary Bedroom with a full bath, and an additional full bath on the main level. The finished lower level offers 540 sq ft of expanded living space with 2 bedrooms and a full bath. Gleaming hardwood floors flow throughout the home, adding warmth and character. Nestled in a neighborhood setting, this property provides the perfect balance of a small neighborhood and accessibility. Located walking distance to ECSU, medical facilities, shopping, dining and more. Enjoy the ease of nearby amenities and easy access to Route 6. Don't miss your chance to make this move-in ready gem your own!

27 Aspen Pl, Windham

99 Bellevue St, Windham
$357,000
5 Beds ⋅ 2 Baths ⋅ 24178511 MLS
Wonderful opportunity to own this charming Craftsman-style home in the desirable Hill Section of Willimantic. Built circa 1932, this well-maintained home is filled with timeless character and original details including beautiful natural woodwork, lovely wood doors, glass door knobs, built-ins, and classic architectural charm throughout. The remodeled kitchen features beautiful cabinetry, granite countertops, and ample workspace, blending modern convenience with the home's original warmth and character. Recently renovated full bathrooms on both the first and second floors offer added comfort and functionality. The flexible floor plan includes a bright sunroom/home office on the main level, ideal for remote work, hobbies, or additional living space. Most of the home features energy-efficient replacement windows. The second floor includes a partially finished walk-in storage room with excellent potential for future expansion into additional living area, studio space, or a bonus room. A large full basement and detached storage shed provide abundant storage options. Additional features include a 2-car under garage and established setting conveniently located close to Eastern Connecticut State University, downtown dining, shopping, and entertainment, with easy access to Route 6 and just minutes to University of Connecticut. A rare opportunity to own a home full of charm, character, and future potential. BOM see agent to Agent remarks.

99 Bellevue St, Windham

176 Windham Rd, Windham
$350,000
8 Beds ⋅ 3 Baths ⋅ 24117978 MLS
Located near the South Windham border of Willimantic, this beautifully maintained 3-family Victorian home is a rare find perfect for investors seeking immediate rental income or owner-occupants looking to live on-site while collecting rent. Nestled in a quiet neighborhood filled with majestic historic homes and directly across from a scenic park, the property offers the perfect combination of location, charm, and functionality. Each of the three spacious, sun-filled apartments features gleaming hardwood floors, large windows, and in-unit laundry. The first and second-floor units boast open floor plans with 3 bedrooms, spacious kitchen, dining room, living room, and a private covered porch or deck-ideal for outdoor enjoyment. The third-floor apartment offers a bright, open layout with a large bedroom, a second flexible room (great for an office or guest space), a sunny kitchen with cross-ventilation, and two oversized storage closets. All three units are currently leased, providing immediate cash flow for investors, & utilities are broken up by apartment. Off-street parking accommodates two small to mid-sized cars per unit, and two interior staircases make access easy for tenants and moving. Whether you're looking for a fully rented investment property or the perfect opportunity to live in one unit while the other two offset your mortgage, this home offers historic charm, modern convenience, and strong rental appeal in one of Willimantic's most desirable neighborho

176 Windham Rd, Windham

384 Prospect St, Windham
$337,000
6 Beds ⋅ 3 Baths ⋅ 24115954 MLS
Charming Victorian Home in the Heart of the Hill Section - Just Steps from ECSU This beautifully crafted Victorian residence offers over 3,000 sq ft of living space and is conveniently located near the entrance of Eastern Connecticut State University. Featuring a spacious chef's kitchen, an inviting front porch, and a covered back porch perfect for relaxing or entertaining. Inside, you'll find a stunning formal dining room, a generous living room with a cozy gas fireplace, and a grand entryway highlighted by a regal staircase. The home includes 6 bedrooms and 3.5 bathrooms, providing ample space. While the property requires some TLC-including yard maintenance and repairs to one bedroom affected by a contained fire-it presents a fantastic opportunity to restore and personalize a classic home. Solar panels and their lease will transfer to the new owner at closing.

384 Prospect St, Windham

174 Mansfield Ave, Windham
$335,000
6 Beds ⋅ 2 Baths ⋅ 24159510 MLS
Well maintained Colonial farm house perfect for investors or owner occupied. This home offers 6 Bedrooms and 2 Full baths. The formal dining room is currently being used as a bedroom space but can be easily opened back up for a dining or social living space. The third floor adds an additional 700+ living space. The home has recently refinished hardwood floors throughout. The spacious kitchen has a convenient walk in pantry space. There is a full bath on the first and second floors with a convenient first floor laundry. recent updates to this home include roof, windows, furnace, kitchen cabinets. The exterior of the home has a covered wrap around porch and a detached 1 car garage and plenty of parking. The home is currently rented for 3,200.00 per month with a lease ending 5/31. This home is walking distance to ECSU.

174 Mansfield Ave, Windham

96 Mcdermott Ave, Windham
$335,000
4 Beds ⋅ 2 Baths ⋅ 24157893 MLS
*Highest & Best Offer Deadline on Tuesday, 3/10/26, 10:00 am.* This beautifully updated and wellmaintained home offers a flexible layout in a convenient neighborhood setting. The main level features comfortable living spaces and three bedrooms with a full bath, while the finished lower level includes a spacious additional room that works perfectly as a fourth bedroom, family room, or multipurpose space, along with a second full bath. You'll love the remodeled kitchen with granite counters, stainless appliances and tile floor - featuring an island and dining space, along with sliders to the expansive deck where you can enjoy outdoor living overlooking a nicely sized yard ideal for relaxation or gatherings. The 1-car garage offers shelter from the weather and great storage. Located close to town conveniences, shopping, medical facilities, dining, and entertainment, this home combines comfort with everyday practicality.

96 Mcdermott Ave, Windham

64 Chestnut St, Windham
$332,500
3 Beds ⋅ 2 Baths ⋅ 24183909 MLS
Located in the Historic Hill section of romantic Willimantic, this charming Craftsman-era bungalow offers the perfect blend of historic character and modern convenience, just minutes from downtown shops, restaurants, and local attractions. Before you even step inside, beautifully maintained gardens welcome you to the expansive front porch-an ideal spot to relax and enjoy the neighborhood's timeless charm. Inside, natural light fills the home, highlighting the sparkling hardwood floors, original turn-of-the-century woodwork, and classic architectural details that reflect the craftsmanship of a bygone era. The main level features a light and bright floor plan, including a fully remodeled kitchen, an updated half bath, and a dedicated first-floor office-perfect for working from home, studying, or creating a private retreat. Upstairs, you'll find three generously sized bedrooms and a tastefully remodeled full bath, providing comfortable living space while preserving the home's historic appeal. Rich in character and enhanced with thoughtful updates, this special Historic Hill home offers a rare opportunity to enjoy the best of Willimantic's past and present in a convenient location close to downtown.

64 Chestnut St, Windham

295 Jackson St, Windham
$323,000
6 Beds ⋅ 2 Baths ⋅ 24137503 MLS
Say Happy Centennial to 295 Jackson St! Being lovingly cared for by current owners for 22 years, they have spared no expenses. She just gets better with age. Whether you are starting your investment portfolio, or looking to round it out, this 2 family home is for you. Close to Willimantic's vibrant Main St, shopping & amenities; everything you need is within minutes. If that wasn't enough, ECSU, Windham HS and Windham Tech are all within less than a mile and a half. Added benefit: On collegiate bus routes and only 10 minutes from UCONN. Each unit features 3 bedrooms and 1 bath, beautiful woodwork & embellishments; built-ins and plenty of pantry/cabinet space. Not one, but two separate driveways; one for each unit. Separate furnaces, hot water heaters, oil tanks and upgraded electrical panels. Recently repainted exterior, energy efficient triple pane windows, new roof including chimney & cap, large basement with both a shared space which you can access the large backyard, with individual storage areas, each with it's own washer/dryer hookups.

295 Jackson St, Windham

81 Chestnut St, Windham
$320,000
3 Beds ⋅ 2 Baths ⋅ 24180787 MLS
Step into timeless elegance with this beautiful Colonial home, nestled in the historic Hill section of town. Built in 1918, this character-filled residence showcases the original charm and craftsmanship that make historic homes so special. From the moment you enter, you'll appreciate the stunning original woodwork, period lighting fixtures, welcoming entryway, and classic fireplace. Large windows throughout the home fill every room with natural light, highlighting the beautiful hardwood floors and architectural details. The main level features a spacious living room, formal dining room, kitchen, full bathroom, and a convenient first-floor bedroom. Upstairs, you'll find two to three additional bedrooms, a second full bathroom, and a large family room offering flexible living space for today's lifestyle. Enjoy relaxing on the covered front porch or take advantage of the home's original sleeping porch, a unique feature that adds to its historic appeal. Many of the home's mechanical systems have been updated, providing peace of mind while preserving its vintage character. Ideally located within walking distance to downtown, you'll have easy access to local restaurants, galleries, shops, and community events. This is a rare opportunity to own a home filled with charm, character, and history.

81 Chestnut St, Windham

99 Quercus Ave, Windham
$320,000
3 Beds ⋅ 2 Baths ⋅ 24170867 MLS
HIGHEST & BEST DUE SAT. 5/9 AT 4:00 P.M. Thoughtfully updated and full of charm, this inviting home offers a flexible layout designed to fit today's lifestyle. A welcoming front foyer sets the tone, leading into sun-filled living spaces with refinished floors and a natural flow that feels both open and comfortable. The remodeled kitchen (2008) anchors the home with functionality and style, while natural gas heat and 200 amp electrical provide modern efficiency and peace of mind. The primary bedroom suite is a true retreat, featuring a full wall of closets and a private full bath. In its current configuration, the home offers two bedrooms plus a versatile flex space, ideal for a home office, guest area, den, or creative studio. The original layout reflected a three-bedroom design, and the space could be reimagined to suit a variety of needs. Outside, the property continues to impress with strong curb appeal, a beautifully maintained backyard, detached one-car garage, and additional shed for storage. There is also excellent potential for a home gym or hobby space, adding even more functionality. A well-cared-for home that blends character, flexibility, and everyday comfort, ready to adapt to its next owner's vision.

99 Quercus Ave, Windham

512 Pleasant St, Windham
$315,000
3 Beds ⋅ 1 Baths ⋅ 24192863 MLS
Welcome to 512 Pleasant Street, a move-in ready single-family home offering comfort, convenience, and modern updates. The beautifully updated kitchen serves as the heart of the home, featuring stylish finishes and a functional layout that's perfect for everyday living and entertaining. This well-maintained property is ready for its next owner to move right in and enjoy. With inviting living spaces, a practical floor plan, and a location convenient to shopping, restaurants, parks, and Eastern Connecticut State University, this home is an excellent opportunity for first-time buyers, downsizers, or anyone looking for low-maintenance living in the heart of Willimantic. Upgrades include new fuse box, sump pump, french drain, furnace, oil tank, roof, central air and HVAC system. Remodeled Kitchen and bathroom Don't miss your chance to own this charming home that combines updated features with move-in ready appeal.

512 Pleasant St, Windham

100 Bolivia St, Windham
$315,000
2 Beds ⋅ 2 Baths ⋅ 24181794 MLS
Looking for an owner-occupied multi-family? Here it is! Located on a quiet street in the desirable Upper Hill section of romantic Willimantic, this well-maintained two-family home is an opportunity you won't want to miss. Each unit offers over 1,000 square feet of living space and features a spacious one-bedroom, one-bathroom layout. Separate driveways and individual garages provide added convenience and privacy for both units. Situated on a generously sized lot, the property boasts a large yard with plenty of outdoor space for gardening, entertaining, recreation, or simply relaxing and enjoying the surroundings. Numerous recent improvements include a freshly painted exterior, updated boilers installed in 2016 and 2021, and a roof replaced in 2015. Additional features include a full basement for storage and utilities, as well as a large walk-up attic offering excellent storage potential or future possibilities. Whether you're looking to live in one unit and collect rental income from the other, or add a solid investment property to your portfolio, this versatile multi-family home is a must-see.

100 Bolivia St, Windham

39 S Windham Rd, Windham
$310,000
3 Beds ⋅ 1 Baths ⋅ 24156298 MLS
We have had a lot of interest on this property therefor we are asking for HIGHEST/BEST BY TUES. 3/10 AT NOON. Charming and well-maintained Cape set on a private 1.1-acre lot, offering peaceful surroundings while remaining close to local amenities and major commuter routes. This home features 1,120 sq ft of living space with 9ft ceilings. Town records reflect a 3-bedroom home; however, one bedroom does not have a closet, offering flexible use as a home office, nursery, or guest room. The inviting dining area showcases a charming corner window seat with built-in storage, creating a cozy and functional gathering space. The home offers a bright living area, a practical kitchen layout, and a full bath featuring a walk-in shower for added convenience. Laundry is thoughtfully accommodated with washer/dryer hookups in the basement, along with additional space in the main-level bedroom suitable for a stackable washer/dryer setup, providing flexibility for single-level living. Step outside to a fully fenced, completely private backyard, ideal for entertaining, pets, or relaxing in your own secluded outdoor retreat. A detached 2-car garage offers ample space for vehicles, workshop needs, and additional storage. Conveniently located near Route 6, Route 32, Eastern Connecticut State University, UConn, shopping, and dining. A wonderful opportunity for first-time buyers, downsizers, or investors seeking privacy and versatility in Windham.

39 S Windham Rd, Windham

139 South St, Windham
$310,000
5 Beds ⋅ 3 Baths ⋅ 24155707 MLS
Enjoy the best of both worlds - homeownership with built-in rental income potential. The main residence offers 4 bedrooms, 1 full bath, and 1 half bath, providing generous space and flexibility. The first floor features a spacious eat-in kitchen, a formal dining room with a cozy pellet stove, and a large living room - both with hardwood floors. A convenient half bath completes the main level. Upstairs, you'll find four bedrooms along with a full bath. A large deck overlooks the spacious backyard, offering plenty of room for outdoor entertaining or relaxing. The covered front porch is the perfect spot to enjoy the warmer months. Adding even more value is the oversized one-car garage with a full apartment above. The apartment includes 1 bedroom and 1 full bath, making it ideal for rental income, extended family, or guests. Located just 1.5 miles from Eastern Connecticut State University and 7.9 miles from UConn, this property presents strong rental and investment potential. With ample off-street parking and flexible use options, it's well suited for an owner-occupied individual seeking supplemental income or an investor looking to expand their portfolio. The property does need some TLC and cosmetic updates, offering a great opportunity to build equity and make it your own. Roof on main house was replaced in 2023 and on the garage in 2026. Being sold as is.

139 South St, Windham

194 Ivan Hill St, Windham
$300,000
5 Beds ⋅ 2 Baths ⋅ 24180102 MLS
Welcome home to this spacious and well-maintained ranch offering 5 bedrooms and 2 full baths in one of the area's most desirable neighborhoods. The bright and inviting kitchen features a new tile floor, granite-topped island, and opens seamlessly to the comfortable living room with beautiful hardwood floors and abundant natural light. The main level includes three generously sized bedrooms and a full bath, while the finished lower level provides exceptional additional living space with a large family room, two more bedrooms, a second full bath, and a convenient laundry area. Need extra storage or future expansion potential? The walk-up attic offers plenty of storage space and could be finished to create even more living area. Outside, enjoy the level yard and patio area-perfect for relaxing, entertaining, or enjoying the outdoors. Located within walking distance to town, you'll love the convenience of nearby restaurants, galleries, parks, and local attractions. This versatile home combines space, comfort, and an unbeatable location-don't miss the opportunity to make it yours! Lower Level Perfect For In Law

194 Ivan Hill St, Windham

98 Windham St, Windham
$300,000
4 Beds ⋅ 2 Baths ⋅ 24113958 MLS
Step into timeless elegance at 98 Windham Street, a circa 1893 Victorian gem set on a rare double lot stretching from Windham St to Tingley St. Brimming with historic character, this home showcases beautifully preserved woodwork, rich hardwood floors, breathtaking stained glass windows, and period fixtures that echo its storied past. This home is in process of being lovingly renovated and restored with attention to authenticity and charm and is ready for you to take over (including building materials and fixtures!). The second full bath is unfinished. You'll love the huge walk-up attic which offers expansion potential and a partially finished room, 2nd story balcony, wrap around front porch, turret, 2-car detached garage, in-ground pool with screened pool house, storage shed, and expansive grounds ideal for outdoor living. A very special opportunity to own a piece of history while adding your own chapter as you complete the renovations. Acreage and Taxes listed are total amounts (both parcels). Cash offers only.

98 Windham St, Windham

252 Roanoak Ave, Windham
$295,000
3 Beds ⋅ 1 Baths ⋅ 24177182 MLS
This charming, move in ready, three bedroom, two bathroom home offers comfort, convenience, and flexibility in a great location close to Windham Middle School and Eastern Connecticut State University. Featuring 912 sq ft of living space on the upper level, plus a partially finished walk-out basement, the lower level includes a full bath and mini kitchenette, offering great potential for an in-law suite, guest space, or bonus living area. Enjoy recent updates including new decks, new windows, a brand-new water heater, and new stove. Connected to public water and sewer and running solely on electricity, this home combines convenience with charm. With excellent curb appeal and flexible living space, this is one you won't want to miss!

252 Roanoak Ave, Windham

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