You are viewing Windsor VT Homes between $250000 and $500000 dollars.
$500,000 $101 per sq.ft. Windsor VT Home »
Price Change! Reduced by $35,000 down 7% on August 8th 2026
Waterfront on Lake Runnenede
6 Beds | 4 Baths | Total Sq. Ft. 4933 | Acres: 0.48
Wednesday May 13, 2026
Description: Come see and appreciate this recently rejuvenated and extraordinary home that includes 6 bedrooms and 4 bathrooms as well as a 2 car garage! Located just off the downtown village area, this unique property features historical charm and character with vintage woodwork, custom wood floors, high ceilings, spacious rooms and the nooks and crannies a classic home has to offer! Relax on the rear porch or enjoy the private yard and great living room that overlook the nearby pond providing a peaceful retreat at the end of a long day! See MLS Property & Listing Details & 36 images.
New Listing!
![Windsor VT Home for sale $$299,000 $260 per sq.ft.]()
$299,000 $260 per sq.ft. Windsor VT Home »
2 Beds | 1 Baths | Total Sq. Ft. 1152 | Acres: 0.99Wednesday Aug 26, 2026
Description: Welcome to 319 Back Mountain Road in Windsor, Vermont, a comfortable 2-bedroom ranch situated on approximately one acre in a peaceful country setting. The home features an updated kitchen and a spacious living and dining area with plenty of natural light, creating a warm and inviting space for everyday living and entertaining. A metal roof and updated heating system add to the home's practicality and ease of ownership. A one-car garage provides convenient parking along with additional storage space. Outside, the level yard with mature trees offers plenty of room for gardening, recreation, or simply enjoying the Vermont surroundings. Located along the eastern slopes of Mount Ascutney, with its hiking trails and recreational activities. This property offers a wonderful balance of rural living and convenience, with easy access to downtown Windsor, I-91, and the area's abundant recreational opportunities. Whether you're looking for a primary residence, Vermont getaway, or a home to make your own, 319 Back Mountain Road offers an appealing opportunity in a desirable Upper Valley location. See MLS Property & Listing Details & 16 images.
$299,000 $260 per sq.ft. Windsor VT Home »
Waterfront on River Beaver Brook2 Beds | 1 Baths | Total Sq. Ft. 1152 | Acres: 6.8
Monday Jun 22, 2026
Description: Embrace the ultimate Vermont lifestyle with this 1950s ranch, perfectly situated on 6.8 sprawling acres of versatile land at 466 Esty Lane in Windsor. Combining nostalgic mid-century charm with extraordinary future potential, this property is an absolute dream for investors, developers, or anyone looking to build their ideal country homestead. The existing home offers 1,152 square feet of single-level living space, featuring two comfortable bedrooms, one full bathroom, and a full basement providing excellent storage or workshop space. While the house requires renovation, it boasts solid bones and a layout ready for your personal touch. For those desiring more space, the structure is suited to easily add a second-floor expansion, allowing you to maximize the footprint and capture beautiful scenic views.The true crown jewel of this property is the expansive acreage. With 6.8 total acres at your disposal, there is incredible potential to subdivide the land into two additional separate lots. Adding to this investment appeal, the land layout accommodates separate entrance possibilities for the new potential lots, ensuring future privacy and ease of access. Nature lovers will be captivated by the extensive river frontage running right along the property line, complete with idyllic spots perfect for a private summer swimming area or peaceful afternoon relaxation by the water's edge.Location is everything, and this property delivers. Nestled on a quiet, serene dirt road, you will enjoy complete peace and privacy while remaining just a short drive close to downtown Windsor's shops, dining, and historic amenities. Outdoor enthusiasts will rejoice knowing that Mount Ascutney is less than five miles away, offering fantastic alpine skiing, snowboarding, and winter recreation right in your backyard, alongside summer hiking. Whether you choose to renovate the existing ranch, expand upward, or pursue the subdivision, 466 Esty Lane offers an unmatched canvas. See MLS Property & Listing Details & 60 images.
Under Contract New Listing!
![Windsor VT Home for sale $$279,000 $356 per sq.ft.]()
$279,000 $356 per sq.ft. Windsor VT Home »
2 Beds | 1 Baths | Total Sq. Ft. 783 | Acres: 2.51Wednesday Aug 5, 2026
Description: Completely rebuilt in 2014 (except for the storage room) and set on 2.51 acres spanning both Windsor and Hartland, this 2-bedroom, 1-bath ranch offers comfortable one-level living with plenty of potential. The open-concept living, dining, and kitchen area creates a functional layout, while the attached direct-entry garage and unfinished attached space provide excellent storage or future expansion possibilities. Outside, the property features a circular driveway, a partially level yard, a small, fenced area off the garage, a larger split-rail fenced paddock with a run-in, a storage shed, and a dedicated chicken coop area, offering flexibility for gardening, hobbies, small animals, or outdoor enjoyment. Conveniently located with easy access to area amenities, this property presents a wonderful opportunity to make it your own. Easy access to I-91, 23 min to DHMC, 15 min from West Lebanon, 22 min to Woodstock, 40 min to Okemo. Open house Saturday, August 8th, 10am-12pm See MLS Property & Listing Details & 21 images.
