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

Vintage Home for sale in Windham County, VT:

Step into a piece of Jamaica Village history. Once home to the F. E. Smith Dry Goods, Ready-Made Clothing, and Grocery Store, this distinctive red-and-white building blends Greek Revival presence with Vermont farmhouse character and now serves as a year-round residence filled with history and personality. The classic façade features full-width double-decker porches, white picket railing, and bold corner pilasters. Inside, this C. 1860 building’s commercial past lives on in a dramatic great room with original built-in storefront shelving and drawer banks once used to display dry goods. Now a unique library, studio and sitting area, the space features wide-plank wood floors, expo

Vintage Home for sale in Windham County, VT:

Welcome to this lovingly maintained country property situated on 5.5 acres in Whitingham, Vermont. Offering a wonderful combination of open pasture, wooded acreage, and privacy, this property has so much to offer. The two-story home has been thoughtfully cared for by its long-time owners and features abundant natural light throughout the main living level. A delightful sunroom provides additional living space with direct access to the deck, perfect for enjoying the peaceful surroundings. A walk-out basement adds flexible space with access to the front yard. Outside, you’ll find beautiful open fields, wooded areas, and a spacious two-story barn in excellent condition, complete with ele

Vintage Home for sale in Windham County, VT:

INVESTORS, LANDLORDS & OWNER-OCCUPANTS - HERE’S YOUR OPPORTUNITY! Whether you’re looking to expand your rental portfolio, create two income-producing units, or live in one unit while the other helps offset your mortgage, this two-unit, up-and-down multifamily property is ready for its next chapter. The heavy lifting has already begun! The current owner has completed the deconstruction, removing all drywall and taking the interior down to the studs, creating a true blank canvas for your vision. Building permits were issued for the deconstruction work already completed. Additional improvements have been made throughout the property, including replacement of the existing chim

Vintage Home for sale in Windham County, VT:

Exquisite! Feel the life, the romance of history and the charm of an era waiting to be recaptured. .. Front stairs! back stairs! third floor for the maid!. .. bedrooms grouped around a child's dream play room. Capture the essence. .. .tall windows, high ceilings. .. room to breathe. .. room to dance. .. room to love. Perfectly decorated, precisely maintained, delightfully presented. All that AND. .. updated in reverence to the era, but functional for those who appreciate the modern way of life. New kitchen, baths, appliances top those polished and gleaming floors. Outside is as lovely as in. .. with a large lazy porch off the kitchen, topped by a Juliette balcony for star gazing and enjoyi