Refine Search
Sort by
$365,000
3 Beds 2 Baths COMING SOON Status 24195071 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

$1,100,000
6 Beds 5 Baths ACTIVE Status 24194248 MLS
The Fenner-Matthewson Mansion-an extraordinary piece of Connecticut history. Built circa 1855 for prominent mill owner Arnold Fenner, this magnificent Italian Villa is a distinguished contributing property within the National Register-listed Central Village Historic District. Nearly 6,000 SF of timeless grandeur offers 12 rooms, 6 bedrooms and 4.5 baths, with soaring 12' ceilings and exquisite period detail throughout. A grand foyer and sweeping staircase make an unforgettable first impression, complemented by 2 additional staircases, original black walnut doors and millwork, red pine floors, mercury glass doorknobs and beautiful built-ins. An incredible 9 working fireplaces, many with distinctive Italian marble surrounds, grace the home-including fireplaces in the updated kitchen and primary suite. The kitchen blends historic character with modern function, featuring a Sub-Zero refrigerator, pantry and butler's pantry. The primary suite offers a private full bath with soaking tub and fireplace. Recent improvements include a new roof and new central air. Set on 2.65 acres with an inviting front porch, stone courtyard and charming stucco outbuilding. More than a home-this is architecture, history and legacy, awaiting its next steward.

40 Main St, Plainfield

$899,900
4 Beds 3 Baths ACTIVE Status 24193491 MLS
Long PRIVATE driveway leads to 56 expansive ACRES of pristine Connecticut COUNTRYSIDE with quiet rural atmosphere. Space for HUNTING wildlife viewing and trails. Recreational Haven, Homestead with enough room for FARMING and timber. ENORMOUS 2400 square-foot GARAGE/WORKSHOP with 12 x 12 doors HEATED with two zones, office with a full bathroom and additional bathroom and its OWN Septic! DETACHED two car garage with (two NEW doors) next to a ONE of a KIND almost 3000 square-foot Country home with BEAUTIFUL CRAFTMANSHIP throughout with CUSTOM STONE fireplace in the large living room with a second FIREPLACE in the dining/custom kitchen (new oven and microwave) area for entertaining with an ambience and 1/2 bath laundry area. Upper level has primary bedroom suite and three additional bedrooms with two full bathrooms. 2 brand NEW mini splits $15,000, two NEW wood stoves and piping $14,000, two NEW well pumps $10,000, NEW spray foam and attic $18,000, 10 NEW windows, two NEW front doors and exterior doors $20,000. Peace of mind with a brand NEW GENERAC generator 24,000 Watts $12,000, newer heating system and updated electrical panels NEW $10,000 kennel for the animals. CAMERAS and AUDIO and OCCUPIED-DO NOT GO ON PROPERTY without LISTING AGENT-THANKYOU

233 Fire Tower Rd, Pomfret

$399,900
5 Beds 4 Baths ACTIVE Status 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 ACTIVE Status 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

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.