You are viewing Windsor VT Homes between $0 and $30000000 dollars.
$413,900 $143 per sq.ft. Windsor VT Home »
Price Change! Reduced by $10,100 down 2% on April 28th 2026
4 Beds | 3 Baths | Total Sq. Ft. 2888 | Acres: 1.22
Listed on Tuesday Mar 24, 2026
Description: Motivated seller! Price drop! A rare piece of Vermont history, thoughtfully preserved for modern living. Dating to 1790, this distinguished brick and frame Colonial stands as a testament to early New England craftsmanship -- and it's ready for its next chapter. Meticulously maintained over the centuries and updated where it counts, this two-story home offers the warmth of wide-plank hardwood and softwood floors, the peace of mind of updated electrical and heating systems, and the curb appeal of a classic standing seam roof and fresh paint throughout. Recent windows flood the interior with natural light while preserving the home's timeless character. Whether you're drawn by the historic details or the practical updates, this property is move-in ready from day one. The kitchen is showstopping with a seamless blend repurposed materials. It exudes character and charm. The attached 1 car garage -- complete with a dedicated storage room/workshop area and a massive open attic accessible from both levels -- offers flexible space for a workshop, studio, or expansion. A property of this age rarely offers this much functional square footage. Positioned conveniently off Exit 9, commuting to the Upper Valley and beyond is effortless. The commercial zoning potential makes this an exceptional opportunity for buyers seeking a live-work arrangement, professional office space, or a savvy investment in one of Vermont's most storied small towns. Historic character. Modern comfort. Extraordinary potential. See Listing Details & 38 images.
$339,000 $158 per sq.ft. Windsor VT Home »
4 Beds | 2 Baths | Total Sq. Ft. 2142 | Acres: 0.25Listed on Friday Apr 3, 2026
Description: Discover space, flexibility, and everyday convenience in this charming 4-bedroom, 2-bath home in the heart of Windsor. Thoughtfully designed with a spacious floor plan, the main living area features warm hardwood floors and abundant natural light, creating a bright and welcoming atmosphere throughout. The formal dining area flows seamlessly into the living room, perfect for both everyday living and entertaining. A main-level bedroom and full bath, along with convenient first-floor laundry, offer ideal single-level living options or guest accommodations. Upstairs, you'll find three generously sized bedrooms, providing plenty of space for family, guests, or a home office setup. Set on a quarter-acre lot, the property offers ample parking and a detached one-car garage, perfect for storage, hobbies, or a workshop. Centrally located and easy access to town, grab your morning coffee just a short walk away or head to the nearby pond for a relaxing swim. A wonderful opportunity to own a well-located home with space, charm, and versatility in Windsor! See Listing Details & 25 images.
New Listing!
$229,000 $227 per sq.ft. Windsor VT Home »
2 Beds | 1 Baths | Total Sq. Ft. 1008 | Acres: 0.05Listed on Thursday Apr 23, 2026
Description: Experience the rare opportunity to own a BRAND NEW home, located in the heart of Windsor. This home seamlessly blends efficiency with style, featuring a thoughtfully elevated foundation designed to sit securely out of the flood zone for total peace of mind. The interior offers open living on the first level, and generous sized bedrooms upstairs, maximizing all the available space. The exterior offers a charming covered porch perfect for relaxing. Enjoy the convenience of being just steps away from the Amtrak station, short drive to the local hospital, access to public transportation, and sidewalks that lead you right up into town. Whether you are looking for a low-maintenance primary residence or a high-demand rental asset, this property's brand-new construction and proximity to major employers is a win-win. See Listing Details & 13 images.
New Listing!
$229,000 $227 per sq.ft. Windsor VT Home »
2 Beds | 1 Baths | Total Sq. Ft. 1008 | Acres: 0.08Listed on Thursday Apr 23, 2026
Description: Take a look at this rare chance to own a BRAND NEW home in the heart of Windsor. Built for efficiency, the house features a raised foundation to keep it out of the flood zone for extra peace of mind. The layout is practical and spacious, offering an open-concept first floor and large bedrooms upstairs. You are within walking distance to the Amtrak station and downtown, and our local Moover public transit service is ready to help. The community hospital is just a shore drive as well. Whether you want a low-maintenance home for yourself or a solid rental property near major employers, this new construction is a great choice. See Listing Details & 10 images.
New Listing!
$139,000 $181 per sq.ft. Windsor VT Home »
1 Beds | 1 Baths | Total Sq. Ft. 768 | Acres: 0.1Listed on Thursday Apr 23, 2026
Description: In the heart of Windsor, this charming opportunity was fully rebuilt in 2018. During the renovation, the foundation was raised to sit securely out of the flood zone, giving you peace of mind. Inside, the home features a large, over-sized entryway that leads into a comfortable open living space. The open loft adds a lot of character and extra charm to the layout. Enjoy the covered porch and the strip of opportunity to tend to some raised garden beds or entertain company. Within walking distance to the Amtrak station and downtown, and just a short drive to the hospital. Whether you want a low-maintenance home for yourself or a solid rental property near major employers, this updated home is a great choice. See Listing Details & 18 images.
$119,000 $496 per sq.ft. Windsor VT Home »
1 Beds | 1 Baths | Total Sq. Ft. 240 | Acres:Listed on Monday Mar 16, 2026
Description: This beautifully crafted 2024 "Incredible Tiny Home" built by Amish Artisans, is ready for its next owner. Thoughtfully designed for efficiency and comfort, the home features a convenient kitchen, a spacious bathroom, and a loft sleeping area with stairs for easy access. A mini-split system provides both heating and cooling, ensuring year-round comfort. Step outside to enjoy the well-built deck--perfect for converting in to a sunroom--as well as a screened gazebo and a storage shed included in the sale. Located in a small, quiet park just 4 miles from I-19, this property offers both charm and convenience. If you've ever dreamed of owning a Tiny Home, this is your opportunity! See Listing Details & 26 images.
