Windham Homes with Cottage Style

Welcome to Windham County, Connecticut, a picturesque region that combines the charm of rural living with the conveniences of modern life. Nestled in the northeastern corner of the state, Windham County is known for its stunning landscapes, vibrant communities, and rich history. Among its many delightful towns, Pomfret stands out as a hidden gem, offering a serene escape surrounded by rolling hills, lush forests, and tranquil lakes.

Pomfret is particularly famous for its enchanting cottage-style homes that exude warmth and character. These charming abodes often feature inviting porches, quaint gardens, and rustic details that make them feel like a storybook retreat. Whether you’re seeking a cozy weekend getaway or a year-round residence, these cottage-style homes provide the perfect backdrop for a peaceful lifestyle. Imagine sipping your morning coffee on a sun-drenched porch or hosting gatherings in a beautifully landscaped yard—life in a Pomfret cottage is nothing short of idyllic.

In addition to its charming homes, Pomfret offers a wealth of outdoor activities for nature enthusiasts. Explore the scenic trails of local parks, enjoy fishing in serene ponds, or simply take a leisurely stroll through the quaint town center, where you’ll find unique shops and delightful eateries. With its rich sense of community and abundance of natural beauty, Windham County—especially the enchanting town of Pomfret—is the ideal place to call home. Embrace the charm of cottage living and discover your dream home in this captivating corner of Connecticut!

Newest Windham Homes with Cottage Style

$384,900

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24205788 MLS

Lakefront living at its best on beautiful Lake Chaffee! This considerately renovated two bedroom, one full-bath cottage offers the perfect blend of charm, comfort, and modern updates. Features include a versatile loft, propane heating stove, generator hookup, new roof, and new electrical and plumbing throughout. Enjoy relaxing or entertaining on the spacious deck overlooking the lake, with a walkway leading directly to your private dock and lake access. A wonderful opportunity to enjoy year-round or seasonal lakeside living in a desirable location! Contact list agent for a list of all renovations completed.

73 Lakeview Dr, Ashford

$517,000

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24201756 MLS

Have you ever wanted your own private backyard beach with private dock? This turnkey, one-level, direct waterfront, year-round home has its own private beach, completed in 2025, along with numerous recent upgrades. Non-motorized watercraft & outboard motors 5 horsepower or less are permitted on the lake by property owners & guests only. Included are several kayaks with a stand, paddle boat, patio set, new shed, floating doc and other outdoor seating, along with custom furniture inside to fit the home in the living room, sunroom, kitchen, and a newer TV w/ wall mount. The relaxing sunroom offers beautiful views of the water and features a new large Anderson picture window with professionally installed remote control blinds and a sliding door out to the deck. This exterior offers easy maintenance with vinyl siding, a newer roof, and composite decking. New foam insulation was installed in 2025. The interior offers commercial-grade laminate floors throughout, and the spacious kitchen is updated with quality-crafted cabinets with pull-out drawers. Entering into the kitchen and living room/dining area are an open floor plan with a brick fireplace. The large master bedroom was completed recently by combining a 2nd bedroom and is on the other side of the kitchen with a 2nd smaller room that's listed as a bedroom currently being used as a storage room and does have the washer and dryer included.

60 Ashford Lake Dr, Ashford

$299,900

3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24198542 MLS

A rare opportunity to create your own waterfront retreat on Alexander's Lake. This 3-bedroom, 1-bath home offers 1,282 square feet of living space with direct lake frontage and a setting that's hard to beat. Inside, you'll find a spacious living area with a brick fireplace and stone flooring, along with a sunroom positioned to take in the water views. Step outside onto the large deck overlooking the lake, with direct access to the water just steps away. The home is ready for renovation, giving the next owner the opportunity to update the space while taking full advantage of its waterfront location. Spend your days kayaking, paddleboarding, fishing or boating on Alexander's Lake, where electric motors only are permitted. Property is located on leased land and sale is subject to Probate Court approval. A little work, a great setting, and plenty of potential-bring your vision and create your own place on the lake.

111 Island Rd, Killingly

$240,000

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24184150 MLS

Lake Life in this small home offering lake views and 2 level living space with large bedroom with storage on upper level. First floor offers a large living room, a bedroom and sitting area with a propane heater stove. The kitchen has space for the laundry equipment, and all amenities and sky lights. The large lot 0.24 acre, 2 sheds, grape vine and expansion possibilities. Selling " AS IS " condition. MOTIVATED SELLER. Closing is subject to seller find suitable housing.

59 Lake View Dr, Ashford

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