Vintage homes for sale & real estate in Windham County, VT

Vintage Home for sale in Windham County, VT:

Own a piece of Vermont history with this charming 1854 home, formerly known as The ThreePenny Lodge and now known as The Cardinal Lodge, nestled in the heart of desirable Newfane near skiing, trails and year-round recreation. Cross a picturesque, covered bridge on your way home and discover a property full of character, currently operating as a successful Airbnb with a live-in caretaker. Whether you're looking for a primary residence, multi-generational home or a vacation retreat, this exceptional property offers endless possibilities. The main living area offers a spacious kitchen that's perfect for gathering and entertaining, while the formal dining room overlooks the gorgeous backyard, c

Vintage Home for sale in Windham County, VT:

This classic Federal-style brick home blends historic character with thoughtful modern updates, offering a lifestyle that feels both grounded and effortlessly comfortable. Set on a dead-end road, the property enjoys the rare balance of peaceful country living and everyday convenience, all within moments of the local store, hospital, pharmacy, bank, and neighboring homes. Inside, you will be welcomed with warmth, timeless craftsmanship, and inviting living spaces designed for both gathering and everyday ease. The gracious foyer is anchored by the original staircase with its elegant handrail and simple period balusters. At the same time, the fanlight transom above the front door adds a distin

Vintage Home for sale in Windham County, VT:

Only 8 miles from Stratton Mountain, this extra-large expanded farmhouse provides ample space, quiet, and tons of classic Vermont charm. Set in a lush garden landscape surrounded by meadows, a stone wall, perennial gardens, an apple orchard, a barn, & multiple outbuildings, the home feels like old Vermont while being close to major amenities. The original home is from the 19th century but contains a new addition from the 21st allowing you & your family to have space. The home has high ceilings, hand-hewn beams, classic woodwork, a wood-burning stove, and walls of windows that bring in warmth & light. The addition includes a grand primary suite with soaring ceilings, views o

Vintage Home for sale in Windham County, VT:

Discover a once-in-a-generation opportunity to own an extraordinary 745± acre estate in the heart of Southern Vermont. Steeped in centuries of history yet thoughtfully updated for modern living, this remarkable property combines unmatched natural beauty, recreational opportunities, and agricultural potential. The diverse landscape features expansive open fields, mature woodlands, pristine streams, scenic mountains. Miles of historic carriage roads have been transformed into an extensive trail network ideal for mountain biking, hiking, trail running, horseback riding, cross-country skiing, and snowshoeing. Abundant wildlife, a productive sugarbush, and managed timber resources make th