Windsor Vermont MLS Listings Homes For Sale

town and country realty associates

You are viewing Windsor VT Homes between $250000 and $500000 dollars.

You can change listings price from to do not use $ or , in amounts
Switch to Land in Windsor VT    Condos in Windsor VT    Multi Family in Windsor VT    Commercial Listigs in Windsor VT  
1 Showing Results 1 to 3 of 3 Page 1 of 1 Results per-page:   5 | 10 | 20 | 50
Under Contract WINDSOR VT Home for sale $$279,000 | $356 per sq.ft.

$279,000 | $356 per sq.ft. WINDSOR VT HOME FOR SALE

15 Rt. 5 North 2 Beds | 1 Baths |   Total Sq. Ft. 783  |  Acres: 2.51

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.


WINDSOR VT Lake House for sale $$299,000 | $260 per sq.ft.

$299,000 | $260 per sq.ft. WINDSOR VT LAKE HOUSE FOR SALE

466 Estey Lane Waterfront Owned 2 Beds | 1 Baths |   Total Sq. Ft. 1152  |  Acres: 6.8

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.


WINDSOR VT Lake House for sale $$500,000 | $101 per sq.ft.

$500,000 | $101 per sq.ft. WINDSOR VT LAKE HOUSE FOR SALE
Price Change! reduced by $35,000 down 7% on August 8th 2026

2 Pine Street Waterfront Owned 6 Beds | 4 Baths |   Total Sq. Ft. 4933  |  Acres: 0.48

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.


1