Windham County 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 County Homes with Historic Antique Style

$515,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24217299 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

$468,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24215683 MLS

A rare chance to live in a home that feels like a story. Welcome to one of Hampton's oldest treasures-an early 18th century Colonial residence built in 1723 known as the "Mosley House". Set along the Main Street corridor referred to as the Hampton Hill Historic District. Set on 1.2 acres at the corner of Main Street and Hammond Hill Road, this is a landmark home recognized by the National Register of Historical Places. Period architecture shines throughout the 4,100+ square feet with 3 fireplaces, a wood roof, wide plank floors, plaster walls, wood paneling details, high ceilings, and both a grand front staircase and a second "back" servant staircase. Inside, the home offers 4-5 bedrooms, 3 full baths, a formal dining room with a barrel back corner hutch, two sitting rooms with fireplaces, a library or den, and a dedicated home office with a separate entrance once used for a home business. The kitchen blends period charm with modern function, anchored by a large stone fireplace, butcher block island, soapstone counters, built ins, and glass paned cabinetry. Several rooms throughout the home include built in shelving and hidden closets. The terraced yard is framed by classic New England stone walls, offering a peaceful outdoor setting that complements the home's historic charm. The craftsmanship, scale, and authenticity are what makes this property truly one of a kind.

298 Main St, Hampton

$329,900

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 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

$574,900

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24212900 MLS

Step onto this property and you are immediately taken with its beauty. Mature landscaping filled with ornamental and native trees including 1000's of spring bulbs, summer lilies, and other perennials surrounded by the stone walls that characterize so much of New England charm. This 1900's home has been carefully updated to highlight its character and history with all the conveniences we have learned to love. The entry way welcomes you with vintage cherry floors, The kitchen has been completely remodeled with new cabinets, quartz countertops, and new appliances. The back ell consists of a walk-in pantry, an oversized mud room with laundry and new 3/4 bath as well as an office with private entrance on the first floor. Spacious Dining room, featuring Washington fir floors is right off the kitchen. The large living room with fireplace, is open to sunroom/family room with ample space for you to spread out and enjoy entertaining. A beautiful staircase leads to three bedrooms, all with wood flooring and remodeled full bathroom. There are possibilities for an in-law suite with not too much effort. Refinished plaster walls and fresh paint throughout. Almost 4 acres gives you room to spread your wings. Open field, perfect for grazing your animals. Concrete pad, ready for your new garage or barn. Most windows replaced; roof on the ell of the house is brand new. Mechanicals are up to date. Ready to for you to move right in!

54 Westford Rd, Eastford

$779,000

5 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24209434 MLS

Set high on historic Woodstock Hill, this distinctive 19th-century property offers a rare combination of history, character, exceptional views, flexible living spaces, guest accommodations, gardens, and opportunity. Offering approximately 2,500 square feet, this beautifully maintained home features five bedrooms and three-and-a-half baths, along with multiple living areas and a beautiful sitting porch overlooking the surrounding landscape. The home has been thoughtfully adapted to accommodate both private living and hospitality, creating flexibility for a variety of lifestyles. Two separate, thoughtfully furnished guest suites provide an established short-term rental opportunity and have enjoyed strong bookings. Guests have included parents visiting their children attending Woodstock Academy and Pomfret School, families attending weddings and local events, and visitors seeking to experience the beauty and charm of Woodstock. The grounds offer another exceptional dimension. Flower-growing areas, gardens, and a flower stand have been developed by the current owners during their first year on the property, building upon their longstanding experience with gardening and growing. The property offers an exciting opportunity to continue and expand the flower-growing vision, create a garden-based business, or explore the possibility of a future studio or shop, subject to applicable approvals.

500 Rte 169, Woodstock

$699,900

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24208396 MLS

Investors and homeowners, take notice! Welcome to The Gathering House, a breathtaking 1837 Greek Revival church seamlessly transformed into a stunning, turnkey residence. Nestled in historic South Killingly, this architectural gem underwent a complete, top-to-bottom restoration. Today, it stands as a fully furnished, 5-star Airbnb/VRBO destination, an exceptional second home, and the ultimate venue for grand-scale entertaining.The main level is dedicated to hosting. Step into the spectacular 1,200 sq ft multi-purpose great room, boasting soaring 14-foot ceilings and flooded with light from seven massive 10-foot windows. This jaw-dropping space features a built-in stage, dining area, comfortable seating for a crowd, and an 85" TV with a sound bar. A convenient kitchenette and half bath are located adjacent to the great room to effortlessly serve your guests.The lower level offers a beautifully designed residential retreat. It features a gorgeous, open-concept kitchen, dining area, and cozy den, alongside 3 bedrooms and a full bathroom. The fully equipped kitchen is ready for business, showcasing rich cherry cabinetry and elegant granite countertops with bar seating. Two bedrooms feature large walk-in closets, while the spacious full bath includes a linen closet and an all-in-one washing machine.Don't miss this incredible turnkey opportunity. Check out the 3D tour and read the glowing guest reviews! The listing agent is one of the owners.

160 Halls Hill Rd, Killingly

$379,900

4 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24207835 MLS

Welcome to the Benjamin Clarke House - a grand 1700s center entrance colonial located on a 2-acre country lot - complete with rolling lawn, gardens, restored shed and a pond. Spacious house with much restoration complete - 2 upstairs rooms and a bathroom still to be completed by the new owners. Charm and warmth prevail in this beautiful home, including wide board floors, fabulous stone fireplaces, 1st floor laundry and a woodstove. Poured concrete and stone foundation. A 1-car garage completes this lovely property.

19 North Rd, Ashford

$699,900

5 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24204013 MLS

Looking for a large home with character and charm. This property offers a beautiful single family home that could be a great place for a multi generational family. If you are looking to expand your imagination, consider creating a lovely Air BNB or a traditional Bed and Breakfast for those travelers visiting our historic, scenic rural area. A drive along the 36 mile highway of Route 169 takes you right through the heart of New England's "Quiet Corner". Perhaps with the 10+ acres you could create a venue for destination weddings or a place family retreats. The historic character of this wonderful old home remains but with many modern amenities. The home was built in 1704 and includes 5 Bedrooms, 2.5 Baths, 2 Fireplaces, and 2 Woodstoves. The attached heated workshop is state of the art and offers many uses. There is a very cool walkup attic, and several outbuildings. Set just off the main road offers a peace and quiet setting. So many possibilities, so much potential. It is a must see.

26 Beecher Rd, Brooklyn

$449,900

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24199139 MLS

This exceptional 1740 antique cape is set on a lovely 1.59 acre property with stonewalls. The home has been beautifully maintained, and is in immaculate, move-in condition! The first floor features a bright, sunny kitchen with a walk in pantry, a large dining room, a living room with woodstove, a sitting room, and a home office. The woodstove was installed in 2025, and adds coziness and warmth to the home. Another highlight of the first floor is a beautiful butler's pantry with custom built-ins. There is also a main level full bath with laundry. The second floor has 4 bedrooms, a full bath, and a large walk in attic area for storage. Other features include a lovely screened in back porch, two barns which would be perfect for a hobby farm or a workshop/studio, and an above ground pool. The spacious, private back yard has a large garden area with perennial plants, two raised beds, and four newly planted fruit trees. Recent updates include a new roof in 2025 with a warranty which will convey, a well pump installed two years ago, a new chimney cap, and many new replacement windows. This home is filled with charm and character, and has a great flexible floor plan. 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

$449,999

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

$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

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Windham County Homes with Historic Antique Style

Newest Windham County Homes with Historic Antique Style

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