Windham County, CT Real Estate Search

Windham County, CT Homes between $350,000 and $400,000 for Sale

Our website features the best real estate search for homes between $350,000 and $400,000 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 $350,000 and $400,000 for Sale

$399,900
5 Beds 4 Baths 24192242 MLS
Timeless New England charm meets modern-day opportunity in this impressive 5-bedroom, 3.5-bath antique Colonial, where historic character and spacious living come together on a picturesque setting. Rich in original details, this one-of-a-kind home showcases wide-plank hardwood floors, stunning decorative fireplaces with ornate mantels, oversized windows, and classic architectural craftsmanship throughout. The spacious country kitchen offers ample room for gathering and opens to multiple living and entertaining spaces, including a formal dining room, inviting family room, and generously sized bedrooms filled with natural light. A flexible floor plan provides endless possibilities for today's lifestyle, whether you're looking for space for a home office, guest quarters, or multi-generational living. Outside, the property continues to impress with a welcoming covered front porch, expansive yard, and an oversized detached 2-car garage/barn offering exceptional storage, workshop space, or hobby potential. Surrounded by mature trees and timeless New England scenery, this remarkable property delivers the perfect balance of privacy, history, and functionality. Whether you're drawn to the craftsmanship of a bygone era or looking for a home with room to grow, this exceptional antique Colonial is ready for its next chapter. Schedule your private showing today and experience the character and possibilities this unique property has to offer.

394 Jerusalem Rd, Windham

$350,000
3 Beds 2 Baths 24160862 MLS
Welcome to place where time truly is the most beautiful thing. There is a particular kind of feeling when you walk through a historic door like this. Maybe it's the hardwood plank floors that have held two centuries of footsteps. Maybe it's the way the morning light hits the windows on every home on Chaplin Street, a village so notable it's listed on the National Register of Historic Places. Maybe it's the quiet and peace that magically flows through a home like this. Built in 1837 as the town parsonage, this home has been part of this community's story for nearly 200 years. Now it's looking for someone ready to write the next chapter. 11 rooms await for the exciting next chapter. The big work is already done. New roof. New electrical panel. Foundation fully repointed with fresh mortar, inside and out. Chimney repointed and stuccoed, New stainless steel liner, crown, and cap installed. What's left to do is the part that lets the new owner make it their own: cosmetic updates, with flooring quotes already in hand for new carpet and refinished hardwood. Set on nearly an acre of flat, open land, this is the kind of property that rewards patience and vision. For the history lover who's been waiting for a home with a past worth preserving, the hands-on owner who sees potential where others see projects, or the investor eyeing the space and the location near UConn and ECSU, this one is worth it all. Come and see what was once part of the past and how it can be a part of your future

60 Chaplin St, Chaplin

$389,000
2 Baths 24173858 MLS
Position your business where visibility, flexibility, and opportunity come together. This beautifully updated commercial property offers over 2,600 sq ft of single-level space at the highly traveled Abington 4 corners of Rt 44 and Rt 97 - a prime location designed to maximize exposure and business growth. Inside, a welcoming front entry opens into a spacious main area filled with endless potential. Ideal for retail, office, industrial, studio, showroom, or service-based use, the flexible layout can easily adapt to your vision. Two additional rooms flow openly off the main space, perfect for offices, meeting rooms, workstations, or added retail display areas. The property also features two half bathrooms, an employee kitchenette/breakroom, and rear access with a second entrance and exit. Outside, a charming picnic and luncheon area offers a great space for employees to relax. Additional functionality includes a lower parking area with a large overhead garage door and expansive storage or maintenance space. An upper driveway and parking area provide easy access for customers and staff, while the smaller garage offers convenient loading, storage, and direct building entry. Extensive recent upgrades include a brand-new roof, refinished original floors, new sheetrock, updated windows, new bathrooms, fresh interior and exterior paint, landscaping, and more. With exceptional visibility on a state highway and endless commercial potential, this is a move-in ready business locatio

500 Hampton Rd, Pomfret

$394,900
3 Beds 3 Baths 24152288 MLS
Welcome to 1 Library Road, a beautifully updated antique Colonial nestled in the heart of Canterbury's Historic District. Built circa 1807, this classic home combines historic charm with modern improvements on a generous 1.15-acre corner lot just steps from the Canterbury Center Historic District and village green, which features fine 18th- and early 19th-century architecture and cultural landmarks. The spacious living room flows into a formal dining room - perfect for gatherings - while the updated eat-in kitchen boasts granite countertops, stainless steel appliances, and plenty of room for daily living. The primary suite offers a tranquil retreat with dual marble-top vanities and refined finishes, and two additional bedrooms share a stylish Jack-and-Jill bathroom with double sinks. Shiplap detailing adds warmth and character to select spaces, and the walk-up attic presents valuable unfinished square footage ideal for a future office, game room, or creative flex space. Outdoors, enjoy a maintenance-free deck overlooking a private, level backyard and fire pit area, perfect for entertaining or quiet evenings. The home has been thoughtfully updated throughout, including modern heating, plumbing, and electrical systems, while preserving its historic essence. 1 Library delivers historic appeal, modern comfort, and standout location - a rare opportunity in one of Connecticut's most charming communities. Be sure to take the virtual tour and prepare to be impressed!

1 Library Rd, Canterbury

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