Windham Homes with Historic Antique Style

Welcome to Windham County, Connecticut, a picturesque region steeped in rich history and charming landscapes. Nestled in the northeastern part of the state, Windham County boasts a unique blend of rural beauty and vibrant communities. With its lush greenery, scenic parks, and quaint town centers, it’s no wonder that families and individuals alike are drawn to this enchanting area.

One of the most captivating features of Windham County is its collection of historic antique-style homes. These architectural gems tell stories of a bygone era, showcasing craftsmanship and design that have stood the test of time. From Colonial-era houses with their stately facades to charming Victorian cottages adorned with intricate woodwork, each home is a testament to the artistry of its time. Imagine strolling through tree-lined streets, where every turn reveals a new treasure, inviting you to explore the rich history that resides within these walls.

Living in a historic antique home in Windham County means more than just owning a piece of history; it offers a lifestyle filled with character and charm. Many of these homes feature original details such as hardwood floors, ornate moldings, and vintage fixtures, providing a unique backdrop for modern living. Residents enjoy a sense of community, with local farmers' markets, artisanal shops, and cultural events that celebrate the region's heritage.

Whether you’re seeking a serene retreat or a vibrant community, Windham County’s historic homes offer the perfect blend of charm and convenience. Discover the timeless allure of this remarkable area and find your dream home among the enchanting antique styles that define Windham County!

Newest Windham Homes with Historic Antique Style

$533,000

5 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24203884 MLS

Beautifully restored 1880 Colonial farmhouse set on an impressive 18.03 acres, offering a wonderful opportunity for farming, homesteading, or simply enjoying the peace and beauty of the countryside. Approximately 10 acres are fenced and well suited for cows, goats, sheep, horses, or other agricultural uses. The property also features a greenhouse, multiple outbuildings, and a farm stand building along the road-perfect for selling farm-fresh goods. The home offers the charm and character you would expect from an 1880 farmhouse, combined with thoughtful updates. The spacious kitchen features an open floor plan, granite countertops, and an abundance of new cabinetry. A convenient mudroom off the side entrance includes a large closet and full bath. The kitchen flows naturally into the family room, where numerous windows fill the space with natural light. Enjoy the warmth of the wood stove and access to the back deck overlooking the beautiful property. The formal dining room and living room provide additional gathering spaces, with the living room featuring a pellet stove. Two additional rooms are currently being used as offices and laundry. The primary bedroom and two additional bedrooms showcase beautiful original wide-board flooring, adding to the home's timeless character. The land is truly special, bordering the scenic Mt. Hope River and offering open space, privacy, and endless possibilities. With its historic charm, extensive acreage, outbuildings, agricultural potential

813 Westford Rd, Ashford

$825,000

5 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24204013 MLS

This beautiful old Colonial home was built on one of the first four parcels of land when Brooklyn was first settled. The historic character is seen throughout the home but with many modern amenities. Five Bedrooms, 2.5 Baths, 2 Fireplaces, 2 Woodstoves, Hot air heat, Newer Windows and beautiful old wood flooring. The attached heated workshop is state of the art and offers many uses. There is a very cool walkup attic, and several outbuildings. The land consists of 21.6 Acres of land with open fields, woodlands and frontage on Blackwell's brook. This lovely setting is off the main road for peace and quiet. The amount of frontage has potential for subdivision and is eligible for a free split.

26 Beecher Rd, Brooklyn

$459,900

5 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24199139 MLS

This beautiful 1740 antique Cape sits on a lovely 1.59 acres with the iconic stone walls of the area. The home is immaculate and ready for you to move right in. The first floor features a kitchen with the pantry everyone wants. In addition there is an impeccable butler's pantry with custom storage and display cases. The dining room is bright and can accommodate large family gatherings. There is a working fireplace in the sitting room and the office receives beautiful afternoon light. The sunny living room boasts a wood stove to keep you warm all winter. There is a first floor full bath & laundry. The second floor has four bedrooms, a full bath, and a large walk in attic. Other features include a screened porch, two barns, which would be ideal for a hobby farm or workshops/studios. There is a fenced-in area for pets, an above ground pool, a large garden area with two raised beds, in ground beds, 4 newly planted fruit trees, and an area for expansion. Half of the property is in the process of rewilding, but it has only been a year and can easily be returned to lawn if desired. Recent updates include a new roof in 2025 with a warranty ,which will convey, many replacement windows, new chimney cap, the well pump was replaced two years ago, and the woodstove was installed in 2025. The home is filled with charm and character and has a floor plan that provides many options. Schedule a time to view this exceptional Brooklyn property

136 Hartford Rd, Brooklyn

$749,900

7 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24198629 MLS

Step back in time while enjoying the comforts of today in this exceptional Antique Colonial, built in 1830 and proudly situated on historic Thompson Hill. From the moment you arrive, the home makes a lasting impression with its welcoming wrap-around front porch, tastefully landscaped grounds, and classic circular driveway. The property also features a sizeable barn, offering abundant storage and endless possibilities. There is even an original "privy"! Inside, the 5-bedroom main residence offers generous closet space, 2 full baths, a thoughtfully designed updated kitchen, both formal and informal dining spaces, and beautifully updated bathrooms.A convenient first-floor laundry adds to the functionality of this spacious home, while the property's original character provides the warmth and charm that only an antique Colonial can offer. A standout feature is the spacious two-story in-law apartment, complete with a private entrance and rear deck. With 2 bedrooms and 1 1/2 baths, this versatile space is perfect for extended family, guests, a home office, or other living arrangements. The property has been thoughtfully improved with updated mechanical systems and a brand-new septic system, providing modern peace of mind while maintaining the home's historic character. This home is ideally located just minutes from the Massachusetts and Rhode Island state lines and major commuter routes allowing quick and easy access to the Arts, Dining, Shopping, Medical facilities and Airports

362 Thompson Rd, Thompson

$475,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24197506 MLS

Investors, take notice! This antique Colonial is situated on an impressive 6.6-acre private lot offering a peaceful setting and endless potential. A portion of the acreage is already cleared, while the property also features three beautiful ponds and plenty of outdoor space to enjoy the tranquil surroundings. Inside, the home offers 4 bedrooms, 3 full bathrooms, and a walk-out basement, providing plenty of space and flexibility for future improvements. A brand-new 200-amp electrical service is already in place, along with a newer heating system, approximately 4 years old, giving the next owner a great start on bringing this property back to life. The home is in need of TLC and updating, but with its antique Colonial character, spacious layout, beautiful acreage, and private setting, the possibilities are plentiful. Whether you're an investor searching for your next project or an owner occupant looking to restore an antique home and create something special, this property is ready for your vision. Schedule your showing today and discover its full potential!

128 Holmes Rd, Pomfret

$500,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24193694 MLS

Everyone loves a great wrap-around front porch, & this one feels like it was made for slowing down. Wrapped in classic columns & overlooking one of Connecticut's most scenic historic districts, this 1830 home offers 4 bedrooms, 3.5 bathrooms, & over 2,800 square feet filled with original character. Step inside to an elegant oak staircase, original hardwood floors, crown molding, & an interior that reminds you why people continue to fall in love with historic homes. The oversized living room is filled with natural light from dramatic floor-to-ceiling windows. A formal dining room flows into the eat-in farmhouse-style kitchen, where a remarkable brick fireplace once served as the home's original indoor cooking hearth. A first-floor en suite bedroom provides flexibility for guests, multigenerational living, or a private home office, while upstairs you'll find three additional bedrooms plus additional rooms ideal for offices, art studios, a library, or hobby space. Outside, the large rear deck overlooks a just over 3/4-acre, partially fenced lot with plenty of room to entertain, garden, or simply enjoy the outdoors. A new roof installed in 2026, solar panels that help offset electric costs, & a one-car garage add everyday convenience. Located along scenic Route 169 in Brooklyn's historic district, you'll enjoy the charm of Connecticut's Quiet Corner just five minutes from everyday conveniences & approximately 45 minutes from both Providence & Worcester.

31 Canterbury Rd, Brooklyn

$365,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE 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

$995,000

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

$799,900

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24193491 MLS

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

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