You are viewing Windsor VT Homes between $250000 and $500000 dollars.
$490,000 $99 per sq.ft. Windsor VT Home »
Price Change! Reduced by $45,000 down 9% on September 6th 2026
Waterfront on Lake Runnenede
6 Beds | 4 Baths | Total Sq. Ft. 4933 | Acres: 0.48
Listed on 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 Listing Details & 36 images.
$475,000 $360 per sq.ft. Windsor VT Home »
3 Beds | 2 Baths | Total Sq. Ft. 1320 | Acres: 16.35Listed on Friday Sep 4, 2026
Description: Pull off County Road and the gravel goes quiet under the tires as 16.35 acres in Windsor, Vermont open in grass, timber, and sky. Hubbard Brook moves through the land with water over stone, cool in the shade and bright where the light finds it, and a snowmobile trail crosses the acreage when winter takes the fields. I-91 sits close enough that the Upper Valley is an easy reach. That is 1268 County Road before anyone touches a doorknob. Stand long enough to smell the wet bank and feel how much ground comes with the house, then go inside to the finished second floor you can use tonight: two bedrooms, two full baths, and a primary suite that takes real space. The walk-in closet is the size of a room and the laundry lives in that closet, so the suite keeps its own rhythm. The primary bath does not force a choice. A jetted tub with a built-in water warmer and a separate walk-in shower mean steam or a long soak with tile underfoot, and two electric fireplaces add a low glow on cold nights. Sellers upgraded the electrical throughout to 200 amp service, and two propane hot-air furnaces split the house by level, the larger one warming the finished floor and the smaller one waiting on the first floor. That first floor is unfinished on purpose, bare rooms and open air where the next owner can draw walls, add square footage, and let the house grow into the acreage. One honest note belongs up front: the roof and the siding both need to be replaced, and with an appropriate offer the seller will escrow funds to complete that work. More photos will follow as belongings are packed and rooms open up. What you are buying is 16.35 acres, a finished floor that works, a first floor to invent, a 200 amp panel, a drilled well with softener and sediment filter, municipal sewer, cable internet, a carport, decks, and a plan for new roof and siding. Come for the land, stay for the suite, and leave with brook sound still in your head. 1268 County Road, Windsor, VT 05089. House plus 16.35 acres. See Listing Details & 20 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
Listed on 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 Listing Details & 60 images.
Under Contract
$299,000 $260 per sq.ft. Windsor VT Home »
2 Beds | 1 Baths | Total Sq. Ft. 1152 | Acres: 0.99Listed on Wednesday 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 Listing Details & 16 images.
Under Contract
$279,000 $356 per sq.ft. Windsor VT Home »
2 Beds | 1 Baths | Total Sq. Ft. 783 | Acres: 2.51Listed on Wednesday 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 Listing Details & 21 images.
