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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

18 Hilltop Dr Unit 18, Windham
$317,000
5 Beds ⋅ 3 Baths ⋅ 24202946 MLS ⋅ Oak Forest Village BLDG.
Welcome to desirable Oak Forest Village. This move-in-ready home offers one of the most spacious floor plans in the complex, with 3 bedrooms on the main floor and 2 on the lower level for ample room to spread out. With two and a half baths, enjoy the privacy of a primary bedroom with an en suite full bath. The open-concept living space features a remodeled kitchen with modern two-tone cabinets, stainless steel appliances, granite countertops and a breakfast bar, along with a designated dining area and a spacious living room with a vaulted ceiling. Perfect for both quiet nights in and holiday hosting. The hardwood floors were just refinished in preparation for the sale, and the half bath in the finished lower level was recently remodeled as well. A 2-car garage with automatic openers offers easy access and additional storage, while the deck and backyard provide space for gatherings, gardening, and outdoor relaxation. You're conveniently close to many amenities, including shopping, dining, golf, ECSU plus the Charles H. Barrows STEM Academy right on Tuckie Rd, and walking trails right behind the neighborhood. All ready and waiting for you!

18 Hilltop Dr Unit 18, 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

41 Lauter Ave, Windham
$315,000
3 Beds ⋅ 2 Baths ⋅ 24185984 MLS
Coming Soon - Don't Miss This One! Completely remodeled from top to bottom, this beautifully updated 3-bedroom, 2 full bathroom ranch is the one you've been waiting for! Every detail has been thoughtfully renovated, offering today's buyers the perfect blend of style, comfort, and peace of mind. Extensive improvements in 2019 include an energy-efficient tankless natural gas heating and hot water system, newer roof, windows, siding, updated plumbing, and 200-amp electrical service, providing modern efficiency and long-term value. The finished lower-level includes a full bath room and a spacious family room offering flexible living space ideal for entertaining, relaxing, working from home, or a playroom. Perfectly situated just minutes from shopping, restaurants, medical facilities, and everyday conveniences, this move-in-ready home combines quality updates with an unbeatable location. More photos coming Thursday! Showings begin Friday, July 17. Homes with this level of renovation and value are in high demand-don't miss your opportunity to be among the first to tour this exceptional property! Ring Doorbell Audio and Video surveillance!

41 Lauter Ave, 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

40 Sanitarium Rd, Windham
$315,000
2 Beds ⋅ 3 Baths ⋅ 24156895 MLS
A rare find indeed. This Cape Cod style home is deceiving from the outside. Plenty of room in this beauty. Street card says 2 bedrooms, but you can utilize many finished heated rooms for additional bedrooms in this home. Finished basement above ground with kitchen, living space and bedroom. Nice floorplan on the main level offering living room/dining room combination with fireplace, full kitchen and main floor bedroom. Current owners have used the main floor bedroom for their dining room. Upstairs has one bedroom and three additional finished rooms all heated so any could be used as bedrooms or multipurpose rooms. Owner purchased the home with all rooms in place none were added after purchase. Three full bathrooms, one on each floor. Breezeway and lovely large 1.3 acre lot. Alot of home awaits you Roughly 2300 sq feet.

40 Sanitarium Rd, Windham

39 Selden St, Windham
$312,821
3 Beds ⋅ 1 Baths ⋅ 24192959 MLS
Welcome home to this inviting ranch, offering the ease and convenience of one-level living just outside the city. Inside, you'll find hardwood floors, a freshly painted interior, a beautiful stone fireplace, and a bright sunroom with skylights the perfect place to relax year-round. Recent improvements include new flooring in the foyer, kitchen, and hallway, an updated bathroom, and a new water heater. The partially finished lower level provides additional living space and offers exciting potential for a future in-law setup. Outside, enjoy a level, landscaped, fully fenced backyard complete with an outdoor fireplace, ideal for entertaining or unwinding. Conveniently located near Routes 6, 32, and 66, with easy access to Hartford, New London, Worcester, Eastern Connecticut State University, and UConn. This comfortable and well-located home is ready for its next owner!

39 Selden St, Windham

18 Pleasant View Ave, Windham
$310,000
5 Beds ⋅ 2 Baths ⋅ 24184494 MLS
Spacious and versatile Cape Cod-style home offering 5 bedrooms and 2 full baths in a highly desirable neighborhood! Situated on a beautiful corner lot, this property provides plenty of outdoor space for recreation, gardening, or entertaining. Recent improvements include a brand-new Well Mclain boiler, adding comfort and peace of mind for years to come. The flexible floor plan offers room for everyone, with 2 full bedrooms on main floor share a full bath with tub. Ample living space and the potential for a home office or guest accommodations. Upstairs 3 bedrooms share a remodeled bath with walk in shower. Enjoy your screened in front porch! 1 Car detached garage with room for storage, recently paved driveway, vinyl siding, newer windows! Conveniently located near the scenic Natchaug River, UConn, Eastern CT University and downtown Willimantic. Located in the highly regarded Blue Ribbon School District. A wonderful opportunity to enjoy space, location, and value all in one property!

18 Pleasant View Ave, Windham

63 Whittemore St, Windham
$310,000
3 Beds ⋅ 2 Baths ⋅ 24159508 MLS
OFFER DEADLINE: The seller is asking for all offers to be in by Tuesday, 04/14, at 6 pm. THANK YOU! Welcome to this well-maintained 3-bedroom, 2-bath ranch offering comfort, convenience, and modern updates throughout. Ideally located near Route 6, this home provides easy access to shopping, dining, and is just a short drive to Eastern Connecticut State University and UCONN. Inside, you'll find beautiful flooring that flows seamlessly throughout the home, along with an updated kitchen featuring granite countertops and stainless steel appliances. Both bathrooms have been tastefully updated, adding to the home's move-in-ready appeal. Step outside to enjoy a spacious deck overlooking a fully fenced backyard-ideal for relaxing, gardening, or hosting gatherings. Additional highlights include a newer roof, hot water heater, and insulation, offering peace of mind for years to come. Don't miss this opportunity to own a turnkey home in a convenient and desirable location!

63 Whittemore 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

156 Brick Top Rd, Windham
$308,000
3 Beds ⋅ 2 Baths ⋅ 24181829 MLS
Welcome home to this charming 3-bedroom, 2 full bath colonial set on a picturesque 1.68-acre lot offering privacy, space, and tranquility. The bright and inviting kitchen feature a new dishwasher and beautiful french doors that open to an expansive private deck - Perfect for outdoor entertaining or relaxing while enjoying the wooded views. A sun filled dining room with a bay window flows seamlessly into the spacious living room, highlighted by a cozy wood stove that is perfect for those chilly evenings. Convenient first floor laundry adds to the home's functionality. Upstairs you will find three comfortable bedrooms, along with an oversized closet for additional storage! The detached 2 car garage/barn offers a versatile space for projects, a workshop, or simply additional storage to suit your needs. Major updates include brand new roofs on the both the house and garage, providing peace of mind for years to come. Don't miss out on the opportunity to own this wonderful property filled with character and comfort!

156 Brick Top Rd, 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

43 Hilltop Dr Unit 43, Windham
$300,000
3 Beds ⋅ 2 Baths ⋅ 24178737 MLS
This charming 3bedroom home blends fresh updates with future possibilities. The remodeled kitchen and new flooring (main level) create a bright, modern feel from the moment you walk in. Enjoy morning coffee on the deck, easy parking with the attached garage, and the freedom to design the lower level into whatever space you've been dreaming of. A home that fits your life today-and tomorrow. There is a powder room on the main floor and a full bath (tub/shower combo) on the upper floor. Furnace was replaced in 2022. Perfect location in the Oak Forest Village; convenient to UCONN, ECSU, Windham Hospital, Golf Courses, Shopping and Airline North State Park Trail. Charles H. Barrows STEM Academy is just down the road.

43 Hilltop Dr Unit 43, 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

390 Mansfield Ave, Windham
$295,000
3 Beds ⋅ 1 Baths ⋅ 24167419 MLS
Welcome to this classic 3 bedroom, 1 bathroom Cape-style home offering timeless curb appeal and comfortable living. The heart of the home is a warm and inviting eat-in kitchen showcasing rich cherry cabinetry with crown molding, granite countertops, a classic tile backsplash, and stainless steel appliances including a gas range and dishwasher - a perfect blend of style and function. Adjacent to the kitchen, a versatile dining room with gleaming hardwood floors offers flexible living space, previously utilized as a bedroom. The bright and welcoming living room is bathed in natural light from a large picture window, with hardwood floors that continue seamlessly into the first-floor primary bedroom. A full bath with tub completes the main level. Upstairs are two carpeted guest bedrooms, one featuring built-in shelving currently serving as a sitting room. The unfinished basement offers excellent storage and exciting potential for future expansion. Outside, enjoy a brick paver patio and a storage shed. Key updates include a brand new hot water heater, and central air to keep you cool and comfortable all summer long. Conveniently situated near the Mansfield/Willimantic border with easy access to Routes 6 and 32, plus nearby shopping, dining, and local colleges. A wonderful opportunity not to be missed!

390 Mansfield Ave, Windham

232 North St, Windham
$290,000
4 Beds ⋅ 2 Baths ⋅ 24190236 MLS
Located in the highly desirable Upper Hills neighborhood of Willimantic, just a short distance to Eastern Connecticut State University, this charming Colonial blends timeless character with an unbeatable location. Offering over 2,000 square feet of living space, this home features four spacious bedrooms, one and a half bathrooms, soaring ceilings, original hardwood floors throughout and a classic wood-burning fireplace that creates a warm and inviting atmosphere. The oversized rooms provide exceptional flexibility. Outside, enjoy relaxing on the covered front porch or entertaining on the beautiful bluestone paver patio. Additional highlights include newer replacement windows, a one-car detached garage and mature landscaping that enhances the home's curb appeal. This property presents an excellent opportunity seeking a home with income potential. Conveniently located near Eastern Connecticut State University, shopping, restaurants, parks and major commuter routes, this is a rare opportunity to own a classic Colonial in one of Willimantic's most sought-after neighborhoods.

232 North St, Windham

41 Hilltop Dr Unit 48, Windham
$285,000
2 Beds ⋅ 2 Baths ⋅ 24190954 MLS ⋅ Oak Forest Village BLDG.
Welcome to Oak Forest Village! This well-maintained 2-bedroom, 2-bath detached condo offers comfortable one-level living in a quiet, well-kept community and is ready for a new owner. The main floor features a bright living room, dining area, and a kitchen with center island seating, all filled with natural light. Enjoy the private deck overlooking a peaceful wooded setting, perfect for relaxing and enjoying the outdoors. The attached garage provides added convenience, and the detached design offers the feel of a single-family home with the benefits of condo living. The walk-out lower level offers abundant storage space and room for a workshop, home gym, or other uses. Move right in and make it your own. Conveniently located near UConn, ECSU, Windham Hospital, shopping, dining, golf courses, and the Airline State Park Trail. Property is being sold AS-IS.

41 Hilltop Dr Unit 48, Windham

360 South St, Windham
$275,000
2 Beds ⋅ 1 Baths ⋅ 24194095 MLS
Some homes just feel welcoming from the moment you arrive-and this is one of them. Nestled on a beautiful corner lot, this lovingly maintained home has been the heart of countless neighborhood gatherings, from summer cookouts to evenings spent relaxing on the oversized wooden swing, built for making memories with family and friends. Perfect for first-time homebuyers or anyone looking for a home that's truly move-in ready, you'll appreciate how meticulously cared for every room has been. It's sparkling clean, filled with pride of ownership, and ready for its next chapter. The spacious lower level offers exciting possibilities with high ceilings and full-size windows, making it ideal for a future family room, home office, gym, playroom, or guest space. Expand your living area whenever you're ready. Located in the heart of Willimantic, you'll enjoy a lively downtown filled with local restaurants, shops, parks, community events, and the energy of Eastern Connecticut State University. Don't miss one of the town's most beloved traditions-the annual Fourth of July Boom Box Parade, a celebration unlike any other. If you've been searching for an affordable home with character, room to grow, and a true sense of community, this is one you won't want to miss. Come see why so many wonderful memories were made here-and imagine the ones you'll create next.

360 South St, Windham

46 Station Rd, Windham
$275,000
4 Beds ⋅ 2 Baths ⋅ 24183752 MLS
Welcome to 46 Station Rd, North Windham, CT. Enjoy comfortable everyday living in this 4-bedroom, 2-bath home. Bordered by a stone fence, this Cape Cod-style home would not look out of place in a storybook. Imagine sharing meals in the inviting dining room. A well-laid-out kitchen with convenient pantry storage makes meal prep a snap. Many rooms feature authentic wood flooring, and there's room for everyone to find a cozy nook. A partially finished, walkout basement has full bath and sitting area. Outside, delightful garden areas offer seasonal delights. For added energy efficiency, solar panels harness the sunlight. The detached one-car garage with room for a workshop/hobby space includes power, lighting, and a 30-amp RV outlet. And should the need ever arise, the Generac generator and generator-ready plug are standing by. Conveniently located near shopping, bus-line, and the Air-Line Trail, and within 10 miles of the University of Connecticut and Eastern Connecticut State University. Whether lounging on the tree-shaded stone terrace. Or a quick dip in the above-ground pool, the next chapter of your story can be written here. Make your move today.

46 Station Rd, Windham

104 Fairview St, Windham
$275,000
2 Beds ⋅ 2 Baths ⋅ 24180685 MLS
Welcome to 104 Fairview Street, Windham, CT! This beautifully maintained Cape is ready for its next owner. Filled with natural light and featuring updated windows, this inviting home offers 2 bedrooms, 2 full bathrooms, a spacious living room, dining area, and a functional kitchen designed for comfortable everyday living. Step outside and enjoy the spacious backyard, perfect for entertaining, gardening, relaxing, or simply enjoying the outdoors. With plenty of parking and a convenient location, this property offers both comfort and practicality. The full basement provides excellent storage and endless potential to create a family room, or a possible 3rd bedroom, home gym, playroom, media room, guest space, home office, or any additional living area that fits your needs. Located near parks, walking trails, local attractions, restaurants, shopping, and everyday conveniences, you'll enjoy everything this vibrant area has to offer. Move-in ready and exceptionally cared for, 104 Fairview Street welcomes you home. Don't miss this opportunity to own a home with space, flexibility, natural light, and a location you'll love.

104 Fairview St, Windham

66 Gifford Ave, Windham
$275,000
2 Beds ⋅ 1 Baths ⋅ 24175215 MLS
There's something special about a home that instantly feels warm and welcoming, and this charming ranch in Windham does exactly that. From the moment you walk inside, sunlight pours through the living room, reflecting beautifully off the hardwood floors and creating a space that simply feels like home. The open layout makes everyday living easy, with a cozy dining area that flows naturally into the eat-in kitchen featuring stainless steel appliances, abundant cabinetry, and plenty of room to cook, gather, and make memories. Both bedrooms offer hardwood flooring, ceiling fans, and generous closet space, creating comfortable retreats at the end of the day. Downstairs, the unfinished basement is ready for your imagination whether you envision a home gym, workshop, recreation room, or additional living space. Outside is where this home truly shines. Relax beneath the covered patio with your morning coffee, listen to the sounds of nature, and enjoy the privacy of the peaceful backyard with various fruit trees. Thoughtfully updated with new kitchen appliances, kitchen flooring, fresh paint, professionally cleaned vents, a new furnace motor, and new water heater, this home offers both comfort and peace of mind! Whether you're just starting out, downsizing, or looking for a place to truly make your own, this inviting ranch is ready to welcome its next chapter.

66 Gifford Ave, Windham

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