Windham County, CT Real Estate Search

Windham County, CT Single Family Homes for Sale

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Newest Windham County, CT Single Family Homes for Sale

$165,500
3 Beds ⋅ 2 Baths ⋅ 24171622 MLS
Completely remodeled 3-bedroom, 2-bath mobile home in North Windham! This move-in-ready home has been thoughtfully updated throughout and features a brand-new roof, new appliances, and modern finishes from top to bottom. The interior offers a bright and functional layout with updated flooring, refreshed kitchen and bathrooms, and comfortable living space. With recent upgrades throughout, this home provides a great opportunity for affordable, low-maintenance living. Conveniently located close to shopping, restaurants, and local amenities.

28 Circle Dr, Windham
$424,900
5 Beds ⋅ 2 Baths ⋅ 24170264 MLS
Step back in time with this beautifully preserved circa 1815 antique home, known as the Old Danielson house, set on an expansive 6.1acre lot. Rich in history and timeless character, this 2,760sqft residence seamlessly blends classic New England charm with thoughtful modern updates for today's lifestyle. Inside you'll find 5 bedrooms, 1.5 baths, and 10 total rooms, offering a versatile layout with warm, inviting spaces. The home features a living room with a wood stove, a spacious family room, and a kitchen with a cozy breakfast nook that is perfect for everyday living and entertaining. Updated elements throughout enhance comfort while preserving original character, creating a home that feels both historic and functional. Set on over 6 acres of land, the property provides privacy and endless opportunity whether you envision outdoor entertaining, gardening, hobby farming, or simply enjoying peaceful surroundings. Pond located just a short walk from the main house adds to the natural beauty and charm. The current owners have completed a wetlands assessment, offering insight into the land's potential, and suggesting the possibility for additional dwellings or expansion. Buyers is responsible for verifying all information regarding future use and development. Ample parking and a convenient location close to local amenities. A rare opportunity to own a piece of local history with the updates you want and character you can't recreate.

760 Upper Maple, Killingly
$654,900
3 Beds ⋅ 3 Baths ⋅ 24163257 MLS
Rare opportunity to own a waterfront ranch with a legal in-law apartment set on over 3 private acres in the peaceful countryside of Ashford. Boasting over 800 feet of direct frontage on a state-owned pond with no other homes on the water, this property offers natural beauty, and a truly one-of-a-kind setting. The main home features a comfortable single-level layout filled with natural light, including a spacious living room with fireplace, an inviting dining area, and a functional kitchen ideal for everyday living and entertaining. Generous bedrooms and well-appointed baths complete the main level. The fully approved in-law apartment provides its own private entrance, kitchen, living area, bedroom, and bath-perfect for multi-generational living, guests, or potential rental income. A partially finished lower level adds valuable flex space for a home office, gym, or recreation room, along with additional storage. Step outside to enjoy serene water views, abundant wildlife, and the peace of having your own private stretch of shoreline-ideal for kayaking, fishing, or simply relaxing in nature. Conveniently located with easy access to Interstate 84 and just a short drive to University of Connecticut, this property combines seclusion with accessibility. A truly unique waterfront retreat offering privacy, versatility, and endless potential.

592 Ference Rd, Ashford
$369,900
3 Beds ⋅ 2 Baths ⋅ 24169587 MLS
2 full nice bathrooms and 3 bedrooms with one having access to fully finished and heated attic. Dining room could be used as a first floor bedroom with closet. New 4 bedroom septic installed. Brand new appliances, stove, fridge, dishwasher, washer and dryer

633 Wauregan Rd, Brooklyn
$495,000
3 Beds ⋅ 2 Baths ⋅ 24168086 MLS
Well-maintained 3-bedroom, 1.5-bath Cape that offers unique flexibility. For more than 75 years, this property was home to a family-run monument business, seamlessly blending residential living with a working space-an ideal setup for today's live/work lifestyle or those simply seeking extra room to fit their needs. Inside, you'll find a functional and inviting layout filled with character. The heated sun porch, formerly used as the business office, now serves as a bright and versatile space. The first-floor primary bedroom adds convenience and features a cedar closet. The home has seen several important updates, including a new hot water heater (2023), water holding tank (2024), oil tank, and septic tank. The roof is approximately 10 years old, and double-pane replacement windows help improve overall efficiency. Enjoy a Trex deck. Adding to the appeal, the abutting land is protected by Joshua's Trust, preserving the natural surroundings and offering lasting privacy. An exceptionally deep detached garage (roof 9 yrs) provides plenty of space for storage, hobbies, or workshop use. With zoning that allows for both residential and commercial use, this property presents a rare opportunity to create the lifestyle you want-whether that's purely residential or incorporating a home-based business. Conveniently situated on Route 6 close to shopping, restaurants, and everyday conveniences, this is a truly distinctive offering with history, flexibility, and potential

203 Willimantic Rd, Chaplin
$859,900
3 Beds ⋅ 3 Baths ⋅ 24169232 MLS
Rare opportunity to own 100 feet of beautiful pond frontage in Thompson, CT! From the moment you arrive, you'll fall in love with the peaceful setting, breathtaking water views, and the care that has gone into maintaining this home. Whether you're enjoying your morning coffee overlooking the lake, relaxing in the hot tub, or unwinding after a long day, this property offers a true sense of comfort, relaxation, and escape. This well-maintained 3-bedroom, 2.5-bath home offers approximately 1,437 sq ft of inviting living space and was thoughtfully designed with energy efficiency in mind, featuring both geothermal heating and solar. The home feels warm and welcoming throughout, filled with natural light and plenty of space to make it your own. The partially finished basement offers added flexibility-perfect for a home office, gym, playroom, or additional living space. Outside, the 0.82-acre lot provides plenty of room to entertain, enjoy the outdoors, and take in the natural beauty surrounding you. One of the standout features of this property is the detached 2-car garage with a spacious loft area and half bath, offering endless potential for a studio, workshop, guest space, home office, game room, or whatever fits your lifestyle best. Whether you're searching for a year-round home or a peaceful waterfront retreat, this property offers the perfect blend of comfort, efficiency, and scenic lakeside living-all tucked away in a quiet Thompson location. HOT TUB is STAYING!

9 Becola Rd, Thompson
$480,000
2 Beds ⋅ 2 Baths ⋅ 24168088 MLS
Brand new construction offering easy, modern living! This thoughtfully designed home features 2 bedrooms and 2 full bathrooms with a bright, open floor plan perfect for today's lifestyle. The spacious kitchen showcases a center island, ideal for entertaining, and flows seamlessly into the living and dining areas. Enjoy an abundance of natural light from the many windows throughout. The primary suite offers comfort and privacy, while additional features include central air conditioning and a 2-car garage. Step outside to a deck overlooking a partial lake view. A wonderful opportunity to own a low-maintenance, newly built home in a scenic setting!

10 Indian Run Dr, Thompson
$400,000
1 Beds ⋅ 1 Baths ⋅ 24168085 MLS
Similar to be built. Charming Craftsman-style home offering efficient, low-maintenance living! This thoughtfully designed 644 sq. ft. home features 1 bedroom and 1 full bathroom with a bright, open floor plan. Large windows fill the space with natural sunlight, creating a warm and inviting atmosphere. The kitchen and living areas flow seamlessly, perfect for comfortable everyday living. Enjoy relaxing on the front deck overlooking a nice, level lot. Additional highlights include central air conditioning and a rare 2-car garage. A perfect opportunity for downsizing, a starter home, or a weekend retreat!

6 Indian Run Dr, Thompson
$659,900
4 Beds ⋅ 3 Baths ⋅ 24160228 MLS
"Buyer's loss, your gain." Modern Luxury meets timeless design on a Cul-De-Sac in Thompson, CT! 38 Madison Ave was custom-built home in 2020 and set on nearly 2 private acres, this masterpiece redefines move-in ready. Located in a subdivision with underground utilities, this home offers an impeccable blend of curb appeal and sophisticated design. The Exquisite Interior Design boosts the heart of the home a chef's dream kitchen, with a gorgeous quartz island, professional-grade stainless appliances, and a stunning marble-inlay herringbone backsplash. The open-concept layout flows effortlessly into a living area anchored by a dramatic floor-to-ceiling stone-textured accent wall w/electric fireplace. Escape to the expansive Primary Suite, a true sanctuary featuring: A freestanding soaking tub set against a custom mosaic niche and a double vanity with sleek matte black fixtures. A dedicated office alcove with vaulted ceilings and abundant natural light and 3 spacious closets to keep your things organized. Outdoor Living: A large composite deck overlooks a lush, private, and wooded backyard-perfect for quiet mornings or entertaining guests. Home has Central Air, high-efficiency forced air, and a spacious 2-car attached garage. Recently painted throughout! Additional Space: Ready to be finished basement offers the perfect footprint for added living, private home gym or a cozy media room. Schedule your tour today to see this GORGEOUS home! Mins to 395 and Center of Thompson

38 Madison Ave, Thompson
$624,000
4 Beds ⋅ 4 Baths ⋅ 24164619 MLS
Beautifully maintained and built to last, this spacious 4 bedroom, 3.5 bath home offers comfort, quality, and exceptional living space in a prime location near prestigious Thompson Hill. Situated on a manicured corner lot, the home features newer vinyl siding with a lifetime warranty, and 50-year shingles for peace of mind. Designed for easy living and entertaining, enjoy the oversized composite deck with electric awning, expansive paver patio, and a recently remodeled family room with custom built-ins and abundant natural light. The oversized two-car garage is wired for heat and connects to a convenient mudroom and laundry room. Inside, you'll find generous room sizes, oversized closets, and flexible living space throughout, including a partially finished lower level with fireplace, wet bar, and half bath. The oversized primary suite features a newly remodeled spa-like bath with soaking tub, walk-in shower, double sinks, and quartz counters. Additional highlights include five heating zones, two central air zones, and a whole-house propane generator for year-round comfort and reliability. Spacious, solidly built, and meticulously cared for - this is a home designed to stand the test of time.

1 Maple Ln, Thompson
$745,000
3 Beds ⋅ 3 Baths ⋅ 24167102 MLS
Approved building lot on desirable street, property is on a shared driveway. TO BE BUILT: A 2,020 sqft., 3 bedroom, 2.5 bath colonial style home sits on a beautiful 2.6 acre lot. The kitchen features a tile backsplash, oversized island, stainless steel range hood, pantry cabinet, and quartz countertops. The living room flows from the kitchen creating an open feel. Hardwood flooring throughout the home. The staircase is a wonderful centerpiece of the home, with banisters and iron balusters. Upstairs you will find 3 large bedrooms. The primary bedroom features a walk-in closet and attached bath with tile shower and double sink vanity. Forced hot air and A/C climate control the home. Attached 2 bay garage, back deck, walk out basement and front porch are just a few other wonderful features.

106 Church St, Brooklyn
$319,000
3 Beds ⋅ 1 Baths ⋅ 24166792 MLS
Back on Market! Buyers backed out because of payoff request is taking too long, should have it soon.|| Welcome to 58 Viens Street in Putnam, offering a fantastic opportunity to build equity and make it your own. This home features a flexible layout with two generously sized bedrooms upstairs and a first-floor primary bedroom, providing convenient living options for a variety of needs. Inside, you'll find hardwood floors throughout much of the home and a kitchen layout that includes a center island overlooking the living room-an ideal setup for a future open-concept design. A pellet stove adds character to the main living area, and the basement includes a workshop space with 220-volt outlets already in place, perfect for projects or additional utility. The home also includes a water purification system, a patio just off the kitchen, a level backyard, and an oversized shed for extra storage. Several key improvements have already been completed, including a roof and siding that are under 10 years old, along with a newer chimney, doors, and some windows. With its existing features and updates, this property presents a great chance for buyers to add their personal touch and maximize value over time.UPDATE: CALLING HIGHEST AND BEST THURSDAY APRIL 23rd BY 5:00 PM

58 Viens St, Putnam
$799,900
4 Beds ⋅ 3 Baths ⋅ 24165439 MLS
TO BE CONSTRUCTED | Starting at $799,900 Welcome to Eastwood Estates, where luxury living meets the natural beauty and tranquility of Woodstock. Set on a picturesque 1.92-acre homesite bordering protected open space and framed by classic New England stone walls, this offering provides a rare opportunity to build a custom home in one of the area's most desirable neighborhoods. Partner with an experienced local builder to create a home that reflects your lifestyle and vision. Choose from thoughtfully designed plans, including a stunning Country Colonial featuring 4 bedrooms and 2.5 baths, or explore alternative layouts, or bring your own ideas to life within the builder's program. Each home is crafted with attention to detail, blending timeless elegance with modern functionality; open living spaces, quality finishes, and design flexibility suited for today's living. Eastwood Estates is governed by covenants that preserve the integrity and value of the neighborhood, including a minimum home size of 2,900 square feet (which may include finished lower-level space). Enjoy the peaceful charm of Woodstock with nearby access to local farms, walking trails, and scenic roads, while still being within reach of everyday conveniences and commuting routes. A unique opportunity to build a home that is both refined and personal, guided every step of the way.

36 Olde Meadow Rd, Woodstock
$299,999
3 Beds ⋅ 3 Baths ⋅ 24131328 MLS
Classic details and practical updates come together in this charming home, where the covered front porch and fenced front yard set a welcoming first impression. The main level offers an easy daily layout with a mudroom, half bath, flexible office or bonus room, a spacious living room with a bow window and built-in bookshelves. The dining room adds character with wainscoting and crown molding, creating a comfortable setting for everyday meals or larger gatherings. Upstairs, the oversized primary bedroom includes its own full bath and his-and-her walk-in closets, joined by two additional bedrooms, another full bath, and extra closet storage. Recent improvements include new carpeting throughout, a boiler installed in 2026, and chimney re-flashing completed in 2024. Outside, the concrete patio, covered front porch, and fenced back yard provide space for outdoor dining, relaxing, gardening, or entertaining. Conveniently located near I-395, shopping, dining, and Davis Park.

23 Winter St, Killingly
$375,000
4 Beds ⋅ 2 Baths ⋅ 24160840 MLS
Delightfully COMPLETELY REMODELED 4/5 Bed, 2 Full bath with WATERVIEWS in almost every room. Enjoy the weather with gorgeous views of Moosup Pond. 2/3 beds on the first level with full bath. Large master suite on the second floor. This house has ALL NEW OF THE FOLLOWING... Roof, Windows, Siding, Flooring, Electrical System, Plumbing, Paint, Kitchen, Stainless Steel Appliances, 2 New Bathrooms, Lighting, HIGH EFFICIENCY HEATING SYSTEM, Plumbing, Well Tank, Well Pump & Doors. There's Been No Stone Left Unturned! There's even an additional 400 sq ft unfinished room that could easily be turned into a huge walk in closet or office space. Additional Site Clean up to be completed before closing. This is the one!

200 Pond Hill Rd, Plainfield
$499,900
3 Beds ⋅ 3 Baths ⋅ 24160115 MLS
To be built similar. Quality built and energy efficient, this 3 bedroom, 2.5 bath Custom Raised Ranch style home with 2 car garage will be built on private 1.47 acre lot. Part of the Ashford Lake Association community, you'll have lake views and access right down the street. This custom built home features high quality amenities and energy efficient construction. The main level has cathedral ceiling with an open floor plan and features hardwood floors in the living room, dining area and kitchen. The kitchen also features solid wood cabinetry and granite counters. A primary bedroom suite with it's private bath and walk in closet, two additional bedrooms and full bath finish the main level. On the lower level you'll find additional living space with a half bath and laundry area as well as a large family room for entertaining. Unfinished storage space and 2 car garage make up the remainder of the lower level. This home will have central air and energy efficient upgrades to drastically reduce your costs for heating and cooling. Construction to begin once contract is received so there is the option to make changes to the plans and pick your finishes. Current tax information is for lot only; full assessment on home will not be done until after construction is completed. Great lot located with access to restaurants, shopping, universities, and major routes. You can be in your new home in 2026!

21 Westview Dr, Ashford
$219,000
4 Beds ⋅ 1 Baths ⋅ 24159602 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
$359,000
2 Beds ⋅ 2 Baths ⋅ 24156526 MLS
Welcome to this charming 2-bedroom, 1.5-bath home that offers the perfect blend of comfort and convenience. Ideal for empty nesters, downsizers, or anyone looking for a fantastic condo alternative, this home provides the privacy of single-family living without the hassle HOA. Step inside and enjoy a warm and inviting layout with comfortable living spaces that make the home feel instantly welcoming. The two bedrooms offer just the ample space, while the 1.5 baths add everyday convenience for both residents and guests. Whether you're looking to simplify your lifestyle or purchase your first home, this property offers easy living in a great location. Professional Photos to follow* Subject to seller finding suitable housing*

70 Hawkins Rd, Woodstock
$279,999
3 Beds ⋅ 1 Baths ⋅ 24156434 MLS
Recently refreshed and priced aggressively for a fast sale, this move-in ready property is an incredible opportunity for both homeowners and investors. The home features light updates throughout, offering a clean, functional space while still leaving room to add value over time. Inside, you'll find a practical layout with comfortable living areas, updated finishes, and plenty of natural light. Whether you're looking for an affordable primary residence or a strong rental/flip candidate, this property delivers flexibility and upside. Situated in a convenient location near downtown Putnam, shopping, dining, and major routes, the home combines accessibility with long-term potential. Priced below market to generate immediate interest - submit your highest and best. Opportunities like this don't last.

259 Church St, Putnam
$199,900
3 Beds ⋅ 2 Baths ⋅ 24150653 MLS
Beautiful, brand new mobile home in excellent Killingly location! This spacious home features 1280 square feet of living spaces, with a bright sunny interior. The large eat-in kitchen has stainless appliances, a farm house sink, a spacious center island with microwave, and range hood. The living room has built in storage, and a ship lap wall for tv mounting. The primary bedroom suite has a private full bath, and extra large closet. There are two additional bedrooms, and another full bath. The mudroom provides a welcoming entrance, along with washer and dryer hookups and storage areas. Other features include energy efficient propane heat, craftsman style doors, low "e" thermal windows, and lots of recessed lighting throughout. There are beautifully built front and side entrances with white railings and composite steps, and there is off street parking for 2 vehicles. This home is located in Bailey Hill Village mobile home park, a well run and nicely maintained neighborhood. The monthly lot charge for the leased land is $470, which covers plowing of the main driveway and septic pumping. The homeowner is responsible for their own lawn care, plowing of their driveway area, and shoveling their walkways and steps. Property taxes are $1,759. Excellent location, on a quiet country road close to RI, with easy access to all major routes. Exceptional opportunity to live in a brand new home with a very affordable budget. Schedule your showing today!

23 Bailey Hill Vlg, Killingly
$699,000
2 Beds ⋅ 2 Baths ⋅ 24142329 MLS
Perched above the shoreline of private Witches Woods Lake, this fully furnished waterfront retreat offers breathtaking water views, exceptional privacy, and a rare sense of tranquility. Brand-new multi-level TimberTech decks spanning roughly 800 square feet create an expansive outdoor living experience, perfectly positioned for entertaining, relaxing, or simply taking in the beauty of the lake below. Extensively renovated with remarkable attention to detail, the home features a beautifully updated granite kitchen with stainless appliances, whole-house mini-split heating and cooling, a new full septic system, refreshed baths, and numerous thoughtful improvements throughout. The main level offers an easy flow between the kitchen and living room, along with two bedrooms and a full bath. A sun-filled enclosed porch opens directly to the decks, creating a seamless connection between indoors and out. The professionally waterproofed and finished walk-out lower level provides valuable additional living space with a spacious recreation room, full bath with laundry, and direct access to the exterior. A one-car garage, breezeway, and multiple storage areas add everyday convenience. Known for its peaceful atmosphere, natural beauty, and walkable lake community, Witches Woods Lake offers kayaking, swimming, fishing, sailing, and regulated power boating, while restrictions on jet skis and personal watercraft help preserve the quiet character that makes the lake so special.

60 Indian Spring Rd, Woodstock
$289,000
3 Beds ⋅ 1 Baths ⋅ 24133723 MLS
RANCH HOME! Bring your vision and make this 3-bedroom, 1-bath ranch your own! Situated on a corner lot, this 960 sq ft home offers great potential with a full basement for added space or storage. Enclosed porch. With some repairs and updates, this property could shine again-ideal for investors, DIY enthusiasts, or first-time buyers looking for a project. Features a dirt driveway and solid bones ready for your finishing touches.

47 Texas Heights Rd, Plainfield
$520,000
4 Beds ⋅ 3 Baths ⋅ 24125003 MLS
Step back in time with this one-of-a-kind 1830 Greek Revival farmhouse, offering 2,150 sq ft of character and charm on a picturesque 0.90-acre lot surrounded by farm land. Just down the hill from historic Woodstock Hill and the Academy, this setting is as scenic as it is convenient. Inside, wide plank floors and distinctive windows frame beautiful country views, while the front entry showcases its original door with full exterior shutters, a hallmark of Greek Revival style. The living room centers on a classic fireplace, and along the upstairs landing a wall of built-in bookshelves creates a welcoming library space. Three bedrooms are located on the second floor, with an additional first-floor room currently serving as a fourth bedroom. The primary includes a walk-in closet and bath with a clawfoot tub. The walk-up attic offers potential for an office, playroom, or studio. The kitchen features a custom layout paired with quality appliances (Sub-Zero fridge & Thor cooktop) and the warmth of a wood stove. Updates include new Trex decking and a newly finished three-season room off the dining room. Historic touches, such as unique wallcoverings and original details, remain intact, blending history, artistry, and the timeless charm of living in Woodstock, CT. Property to be sold in as-is condition.

101 Child Hill Rd, Woodstock
$439,000
4 Beds ⋅ 2 Baths ⋅ 24132242 MLS
Nestled in the peaceful, rural charm of Scotland, CT, this lovingly updated 9-room, 4-bedroom, 2-bathroom home delivers the perfect blend of comfort, character, and modern convenience. From the moment you arrive, you'll feel the embrace of home - and see endless opportunities for family life here. This home is ready for your life to unfold - from quiet weekday mornings to lively gatherings. Step inside to discover a brand-new kitchen designed with both functionality and elegance in mind-featuring modern cabinetry, sleek countertops, and stylish fixtures. Both full bathrooms have been fully renovated. Throughout the home, gleaming hardwood floors flow seamlessly from room to room, adding warmth and character to every space. Set on a serene property surrounded by the natural beauty of eastern Connecticut, this home offers the ideal mix of quiet country living and modern comfort-all within a short drive to nearby amenities, schools, and major routes. SOLD AS-IS.

7 Devotion Rd, Scotland
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