Windham County, CT Real Estate Search

Windham County, CT Homes between $300,000 and $350,000 for Sale

Our website features the best real estate search for homes between $300,000 and $350,000 available in Windham County, CT and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official REALTOR®’s database every 15 minutes. 

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Newest Windham County, CT Homes between $300,000 and $350,000 for Sale

135 Armitage Rd, Ashford
$350,000
3 Beds ⋅ 2 Baths ⋅ 24216124 MLS
Tucked into a private, wooded setting in Ashford, this 3-4 bedroom, 2 bath contemporary style raised ranch offers comfortable living space, thoughtful updates, and room to spread out. The main level centers on a bright kitchen with a vaulted ceiling and skylight, oak cabinetry, a pull-down faucet over a double sink, and a peninsula with breakfast-bar seating. It opens to the dining area, where a wide bank of windows looks out onto the trees. A few steps away, the living room has its own vaulted ceiling, a ceiling fan, and a tiled fireplace, with a wood-railed overlook that keeps the spaces connected. The bedrooms have hardwood floors, ceiling fans, and good closet space, including a primary bedroom with two double closets. Fresh paint throughout gives the home a clean, move-in-ready feel. The lower level adds flexibility with a bonus room that has direct access to the backyard, plus a second room suited for an office, den, bedroom or guest space. A full bath with tub and a dedicated laundry room with a utility sink and cabinets round out the level. Practical features include hot water baseboard heat, a Generac standby whole house generator, and an attached/drive-in 2 car garage. Outside, a large chain-link fenced yard is ready for pets or play, surrounded by mature trees for privacy. Adjacent to Tinkerville Brook Preserve. Enjoy a quiet country setting with convenient access to I-84 Sturbridge MA, Boston and UConn

135 Armitage Rd, Ashford

139 Herrick Rd, Brooklyn
$329,900
2 Beds ⋅ 2 Baths ⋅ 24217215 MLS
HIGHEST & BEST DUE 10/29 AT 4PM. Full of rustic charm and storybook character, this custom-built chalet-style home is tucked away in a picturesque woodland setting! Bring your vision and imagination to 139 Herrick Road in Brooklyn! Situated on approximately 8 acres, this unique 2-bedroom, 2-bath home features soaring cathedral ceilings, exposed timber beams, beautiful wood interiors, and distinctive architectural details reminiscent of a European mountain chalet. Dramatic rooflines, expansive windows, an open loft overlooking the main living area, and a spacious wraparound deck add to the home's one-of-a-kind appeal. The loft provides additional flexible space with a variety of possibilities. A charming pond with a cute shed along its banks creates a beautiful setting, especially when surrounded by the brilliant colors of New England's fall foliage. Inside, natural wood finishes, rustic details, and two wood stoves contribute to the home's cozy, cabin-like atmosphere. Whether you envision a peaceful country retreat or a place to enjoy nature and the changing seasons, this property offers wonderful possibilities. The home is in need of repairs and updating and is being sold strictly AS-IS through an estate. Bring your vision and imagination to restore this distinctive woodland retreat to its full potential! Being sold strictly AS-IS through an estate. Home will not be dewinterized for inspections or appraisal. Subject to Probate approval.

139 Herrick Rd, Brooklyn

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

207 Summit St, Windham

692 Chestnut Hill Rd, Killingly
$350,000
3 Beds ⋅ 1 Baths ⋅ 24215273 MLS
Charming Ranch in Scenic Killingly, Connecticut! Discover the beauty of country living in this inviting 3-bedroom, 1-full-bath ranch, offering 1,008 square feet of comfortable single-level living on a spacious .46-acre lot. Nestled along the picturesque back roads of Killingly, Connecticut, this property offers a wonderful combination of peaceful surroundings, natural beauty, and everyday convenience. Enjoy the outdoors complete with an oversized back deck, perfect for entertaining, outdoor dining, relaxing, or simply taking in the beautiful New England scenery. An additional outbuilding provides valuable storage space for outdoor equipment, tools, and seasonal belongings. Surrounded by scenic rivers, winding country roads, and vibrant landscapes, this location offers the opportunity to experience the beauty of all four New England seasons. Conveniently situated for an easy commute to both Rhode Island and Massachusetts, this property offers the perfect balance of tranquil country living and accessibility. Whether you're searching for your first home, looking to downsize, or simply seeking a peaceful place to call your own, this charming Killingly ranch is full of possibilities. Your opportunity to own a piece of Connecticut's beautiful Quiet Corner is here! With its desirable single-level layout, generous outdoor space, and convenient location, this property is one you'll want to see for yourself. Don't just imagine the possibilities-come

692 Chestnut Hill Rd, Killingly

30 Hilltop Dr, Woodstock
$350,000
2 Beds ⋅ 1 Baths ⋅ 24214889 MLS
Charming Home on Beautiful Bunggee Lake Experience the beauty of lakeside living in Connecticut's picturesque Quiet Corner! Welcome to this inviting and spacious 2-bedroom ranch, nestled in the beautiful town of Woodstock, Connecticut, along the desirable Bunggee Lake. Whether you're searching for a peaceful year-round residence, a relaxing weekend retreat, or the perfect place to enjoy all four New England seasons, this property offers a wonderful opportunity to embrace the lake lifestyle. Step inside and discover a warm, welcoming home featuring convenient one-level living. The main floor offers two generously sized bedrooms, a full bathroom, a spacious living room, and a comfortable kitchen, providing plenty of room for everyday living and entertaining. The expansive lower level presents incredible potential for additional living space! With its generous size and convenient walkout access, this area offers endless possibilities for a future in-law suite, guest accommodations, recreation room, home office, or additional finished living area. Outside, enjoy the privacy of your own yard and driveway, creating a peaceful setting to relax, entertain, or simply appreciate the natural beauty surrounding you. Imagine experiencing all four seasons in this beautiful lakeside community - warm summer days enjoying the lake, breathtaking autumn foliage, peaceful winter scenery, and the refreshing beauty of spring. Located in Woodstock, one of

30 Hilltop Dr, Woodstock

114 Green Hollow Rd, Killingly
$340,000
6 Beds ⋅ 2 Baths ⋅ 24207270 MLS
Multiple Offers: Highest and Best Offer Deadline 5PM Tuesday Oct 27 2026. Quiet Corner ease! 2 Units for an extended family or live in one unit; let the other unit's rent pay most if not all the mortgage. Big 2 family, 2766 sq feet heated, on 0.66 grassy acre with 2 car garage, large shed, and above ground pool. 1st floor unit: 3 bedrooms, full bath with pocket door, kitchen, dining area, living room, mudroom with lots of storage and washer hookup, enclosed unheated sunporch, and breezeway to 2 car garage. 2nd floor unit: 3 bedrooms, 1 oversized full bath with washer hookup (a perfect spot for stackables), large kitchen, living room, walkup attic for storage or more liveable space if you finish it. See floorplans in photos. Quiet road, large paved driveway in excellent shape, recently resealed. Lovely old large, flat granite block for front stoop. Full unfinished basement has big workbench that will convey. Newer vinyl windows throughout! Both units share the septic and share the well; unknown which unit's elec meter has the well pump on it. Generator hookup in garage. Oil, radiators, one furnace currently, but there were two: concrete pad and oil line for 2nd furnace in basement. Same family for 100 years. Well maintained, but in need of cosmetic updates; unknown if hardwood floors under carpeting. Roof 20 years old with 50 year shingles and looks great. Deck at pool is mahogany. Staircase to 2nd floor mahogany with stair treads pressure treated wood.

114 Green Hollow Rd, Killingly

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