Windham County Homes for Sale

Windham County Homes for Sale

Welcome to Windham County, Connecticut—a hidden gem that perfectly blends charming New England character with modern convenience. Nestled in the northeastern part of the state, Windham County is renowned for its picturesque landscapes, vibrant communities, and rich history. From the lush rolling hills to the serene lakes, this county offers a tranquil escape while still being within easy reach of urban amenities.

Windham County is home to a variety of towns, each with its own unique charm. Whether you’re exploring the quaint streets of Willimantic, enjoying the scenic beauty of Mansfield, or experiencing the rich heritage of Putnam, you'll find a welcoming community that prides itself on its local culture and outdoor activities. With an array of parks, hiking trails, and recreational areas, nature enthusiasts will feel right at home.

For those considering a move to this enchanting area, the real estate market in Windham County is thriving. Homes for sale range from historic colonial houses to modern single-family homes, catering to diverse tastes and budgets. Whether you’re a first-time homebuyer or looking to downsize, you’ll discover properties that boast spacious yards, updated interiors, and proximity to local amenities.

With its blend of small-town charm and vibrant community spirit, Windham County is not just a place to live—it's a place to thrive. Explore the homes for sale today and discover the perfect setting for your next chapter in this idyllic corner of Connecticut!

Newest Windham County Homes for Sale

14 Ashford Lake Dr, Ashford
$1,200,000
2 Beds ⋅ 4 Baths ⋅ 24215704 MLS
Stunningly situated on the mouth of Ashford Lake, a project of love has culminated into a brand new dream home, with panoramic views of the lake. Quality craftsmanship is showcased throughout the home, from the kitchen with oversized island, quartz countertops and walk-in pantry, to the transom windows, bathing the great room with an abundance of light. No detail has been overlooked, using only the highest quality materials. Extensive molding, paneling and trim work elevates the ascetic and style of the home. Set on two parcels, there is 254 feet of water frontage with a private dock. Immerse yourself in the beauty of the lake with all the modern comforts. Ashford Lake Drive is lightly traveled and there are no neighbors to the south side, which adds to the tranquil setting.

14 Ashford Lake Dr, Ashford
15 Margaret Henry Road, Killingly
$565,000
3 Beds ⋅ 3 Baths ⋅ 1426621 MLS
Discover the charm of Connecticut's Quiet Corner! Set on a beautiful, level 5+-acre lot, this spacious modern 3 bedroom colonial home offers the perfect blend of privacy, recreation &convenience. This move in ready home features a tremendous amount of updates including newer roof, siding, windows, pool liner and chimney plus updated kitchen! Spacious open floor plan showcases an updated kitchen with granite counters, newer stainless appliances and an abundance of cabinetry plus generous dining area with sliders and access to the oversized deck. The fireplaced family room with 4 casement windows allows an abundance of natural light to flow in, a large living room provides extra space for entertaining during the holidays and 1st floor laundry for convenience. Upstairs features 3 generous sized bedrooms with ample closet space. Primary bedroom with updated full bath plus 2 additional bedrooms with generous closet space. An oversized 2-car garage provides additional storage, while abundant off-street parking accommodates boats, RVs, trailers and other recreational vehicles. The property is an outdoor oasis featuring an inviting in-ground pool, patio (updated) and deck areas perfect for summer entertaining. Think ahead! In winter, the expansive acreage offers plenty of room for ATV fun and outdoor recreation. A rare metal outbuilding with electricity, overhead door and possible access to Route 6, is ideal for collector cars, motorcycles, equipment, workshop space or other hobbies.

15 Margaret Henry Road, Killingly
48 May Brk, Woodstock
$735,000
4 Beds ⋅ 4 Baths ⋅ 24215553 MLS
Some homes just feel like home the moment you arrive, and 48 May Brook Road is one of them! Nestled in one of Woodstock's most desirable neighborhoods, this charming Colonial offers 3,537 square feet of thoughtfully designed living space, picturesque views, and sunsets you'll never grow tired of. A welcoming farmer's porch sets the tone, while the beautifully maintained grounds create an unforgettable first impression. Inside, the main level features an open-concept kitchen with walk-in pantry, dedicated dining area, two spacious living areas including one with a cozy gas fireplace, a private home office, and convenient first-floor laundry. Upstairs, you'll find four generously sized bedrooms and two full bathrooms. The finished walkout lower level offers incredible flexibility with an additional bedroom, full bathroom, media room with equipment included, ample storage, and potential in-law accommodations! Step outside to enjoy the expansive deck overlooking Connecticut's Quiet Corner, beautifully manicured grounds, a storage shed, and even a batting cage! Located within the Woodstock school district, this property offers the perfect combination of comfort, space, and New England charm. Homes like this don't come around often.

48 May Brk, Woodstock
128 Beacon Rd, Windham
$363,000
3 Beds ⋅ 3 Baths ⋅ 24215244 MLS
Welcome to a beautiful home situated on a quiet neighborhood street just minutes from ECSU and an easy commute to UConn. Pride of ownership shines throughout with newer flooring, fresh neutral finishes, and an inviting living room featuring a fireplace with electric insert. The finished walkout lower level offers a dry bar, wood stove, and sliders to the outdoors-perfect for entertaining, a recreation room, home gym, media room, or hobby space. Car enthusiasts and outdoor adventurers will appreciate the 2-car under-house garage PLUS a detached, open-front, 3-bay covered parking structure with additional upper-level area! Spaces are ideal for vehicles, recreational toys, tools, and equipment or a workshop/ storage combination. Step outside to an expansive deck overlooking a tree-lined backyard offering a wonderful sense of privacy, perfect for outdoor entertaining, grilling, or simply relaxing and enjoying the peaceful surroundings. A large, freshly painted deck adds to the appeal. This property offers an exceptional combination of comfortable living, versatile space, abundant storage, and a private backyard setting complete with raised garden beds and a pear tree. A UNIQUE OPPORTUNITY WITH SPACE FOR IT ALL!

128 Beacon Rd, Windham
29 Marcy Ln, Thompson
$599,900
3 Beds ⋅ 3 Baths ⋅ 24215871 MLS
Discover a truly unique property offering three full levels of versatile living space, exceptional privacy, and an outdoor setting designed to be enjoyed in every season. The main level welcomes you with a grand family room featuring soaring vaulted ceilings, a walkout to the expansive rear deck, and a charming front sitting porch. The beautifully renovated kitchen showcases butcher block countertops, stainless steel appliances, and a stunning center island, complemented by a dedicated dining area with a custom coffee station and bay window that fills the space with natural light. An elegant arched doorway leads to a second living room featuring a propane gas fireplace, creating a warm and inviting retreat. A full bathroom with a beautifully designed tiled shower and French doors opening to a private deck complete this level. Upstairs, you'll find three bedrooms, including a spacious primary bedroom with ample room for additional furnishings, along with a flexible bonus room ideal for a home office, guest room, or additional bedroom. A full bathroom with a convenient in-home washer and dryer adds everyday functionality. The fully finished lower level expands the possibilities even further, offering a private room currently used as a bedroom, an additional common area currently set up as a workout room, and a third full bathroom with a tub and shower. Set on nearly five private acres, the outdoor amenities are just as impressive.

29 Marcy Ln, Thompson
300 Starkweather Rd, Plainfield
$699,000
3 Beds ⋅ 3 Baths ⋅ 24214706 MLS
Discover this distinctive country retreat on 5+ picturesque acres, featuring a custom-built home with approximately 2,264 finished square feet, 3 bedrooms, and 2.5 baths. The main level living room boasts a cathedral ceiling, wood stove, and hardwood floors. The dining room features built-in cabinetry, while the kitchen offers granite countertops, a center island, custom cherry cabinetry, and a spacious walk-in pantry with a secondary sink. Enjoy scenic views of the private pond and landscape from the living room and sunroom. The main-level primary suite features French doors and a full bath. Two additional lower-level bedrooms offer French doors and direct patio access and one includes an en-suite bath. A walk-out basement provides convenient access to the outdoors, while the oversized two-car garage offers ample space for storage. The property's outdoor amenities are equally appealing, highlighted by a private spring-fed pond spanning approximately 1.25 acres with an estimated depth of 13 feet. An expansive patio, timber pavilion, and covered porch create inviting settings for outdoor dining, entertaining, or simply enjoying the peaceful surroundings. A solar array and standby generator provide additional utility and resilience. Perfect as a year-round residence, weekend retreat, or multi-generational home, this property offers privacy, flexible living spaces, and a peaceful rural setting while retaining driving access to Boston, Providence, and New York City.

300 Starkweather Rd, Plainfield
128 Spicer Rd, Thompson
$529,000
4 Beds ⋅ 4 Baths ⋅ 24215804 MLS
Welcome to 128 Spicer Road! Set on 3.43 acres in a desirable Thompson location, this spacious 4-bedroom, 3.5-bath Colonial offers the perfect blend of comfort, functionality, and room to entertain. The beautifully renovated kitchen features granite countertops, stainless steel appliances, ample cabinetry, and a convenient center island. Luxury vinyl and tile floors flow throughout the first level, which offers an inviting living room with a brick fireplace, a spacious dining area, and flexible living spaces ideal for everyday living. Upstairs, you'll find generously sized bedrooms with brand-new carpeting, including a spacious primary bedroom. The finished walkout lower level provides additional living and entertaining space, complete with a custom bar, recreation area, and full bathroom-perfect for gatherings, game nights, or guests. Additional highlights include central air conditioning, a new oil tank, new hot water heater, and an attached two-car garage. Outside, enjoy 3.43 acres of land offering privacy, outdoor recreation, and plenty of room to relax. Conveniently located just minutes from Thompson Speedway Motorsports Park and Raceway Golf Club, this property offers the space, setting, and amenities you've been looking for. Don't miss your opportunity to make this wonderful property your own!

128 Spicer Rd, Thompson
6 Meadow Ln, Canterbury
$309,800
3 Beds ⋅ 1 Baths ⋅ 24215720 MLS
BACK ON THE MARKET ... SEE AGENT REMARKS WONDERFUL 3 BEDROOM RAISED RANCH ON PRETTY COUNTRY LOT LOVINGLY CARED FOR AND MAINTAINED BY THE ORIGINAL OWNERS FOR OVER 50 YEARS THIS FLOWING FLOOR PLAN FEATURES A FIREPLACED LOVELY LIVING ROOM WITH HARDWOOD FLOORS WHICH OPENS TO A SPACIOUS EAT IN KITCHEN/DINING AREA WITH NEWER SLIDER TO THE EXPANSIVE BACKYARD GREAT FOR FALL GRILLING, BARBECUES AND THROWING A FOOTBALL. EXCITING FINISHED LOWER LEVEL FAMILY ROOM/ REC ROOM WITH FUN BAR AREA. NEWER ROOF, SEPTIC TANK, CHIMNEY LINER. 2 CAR GARAGE. THIS HOME IS A PLEASURE TO SHOW! FHA APPRAISAL ALREADY COMPLETED.

6 Meadow Ln, Canterbury
692 Chestnut Hill Rd, Killingly
$350,000
3 Beds ⋅ 1 Baths ⋅ 24215273 MLS
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692 Chestnut Hill Rd, Killingly
38 Crystal Rd, Windham
$229,900
2 Beds ⋅ 1 Baths ⋅ 24215087 MLS
Adorable ranch/split level home! Convenient yet quiet non through road. Walk to the bus lines and shopping. Cute 2 bedroom home with updated bath, living room with fireplace. LVP and tile flooring throughout.Three outbuildings, side porch, and front patio. Heated lower level needs updating but great for expansion. Attached garage and walkout basement. Newer septic tank.Great backyard, paved driveway, set up a showing today.

38 Crystal Rd, Windham
Plainfield
$929,900
5 Beds ⋅ 5 Baths ⋅ 24215278 MLS
Welcome to this extraordinary contemporary masterpiece, where architectural elegance meets a semi secluded natural paradise. Perfectly situated on a private wooded lot complete with picket fence that lines driveway. This beautiful 5-bedroom, 4-bathroom home offers the ultimate retreat for modern living and sophisticated entertaining. Step inside to a dramatic, floor plan highlighted by soaring vaulted ceilings and an exquisite stone fireplace that anchors the main living space. Loads of natural light that seamlessly bring the outdoors in. The gourmet, beautifully updated kitchen is a chef's dream, featuring a massive built-in pantry, sleek countertops, and stainless steel appliances. Just above the main living area, a spectacular open loft provides a flexible space ideal for a home office, library, or studio. With five generously sized bedrooms and four completely remodeled bathrooms, there is no shortage of space or comfort. The luxurious primary suite serves as a private oasis within the home, complete with elegant soaking tub and peaceful views of the surrounding tree line. The massive, finished basement expands your living space exponentially. It boasts a massive rec room, offering the perfect setup for a home theater, game room, or private gym. Step outside into your large yard with a pool and large deck. Surrounded by nature and tranquility. A wonderful retreat that is close to major highway. Come see for yourself.

Plainfield
33 Machine Shop Hill Rd, Windham
$519,900
4 Beds ⋅ 4 Baths ⋅ 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
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The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

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