You are viewing All Upper Valley NH Homes between $250000 and $500000 dollars.
New Listing!
$440,000 $247 per sq.ft. Village of Post Mills in Town of Thetford VT Home »
3 Beds | 3 Baths | Total Sq. Ft. 1781 | Acres: 6.91Listed on Thursday Aug 27, 2026
Description: This is a well-built Dutch Colonial style home with exposed beams and 3 fireplaces, one with a Vermont Castings gas stove, and one hearth, all wrapped in cedar shake siding. The home offers 3 bedrooms upstairs, plus a den/office on the first floor, and 2.5 baths, all set on 6.91 acres with 472.3'+- river frontage, a pond, and open field land. The property also features a 5-stall horse barn with a heated office and open sheds making it an ideal setting for equestrian pursuits, hobby farming, or simply enjoying the peace and beauty of the countryside. The property is conveniently located just 6 miles from I-91 and approximately 20 minutes from Hanover. This special property combines privacy and rural charm with access to excellent primary and secondary schools, libraries, a publicly accessible lake beach, many walking trails and other family-friendly amenities. The unfinished basement ceiling height exceeds 8-feet; a renovation will significantly increase the total finished floor space, or enable a workshop addition. With some TLC, this home's magic will be restored, and the investment will yield longer term value. Sign on property. This is an estate sale; the property is being sold as-is, where-is. See Listing Details & 57 images.
$499,000 $297 per sq.ft. Thetford VT Home »
3 Beds | 2 Baths | Total Sq. Ft. 1680 | Acres: 0.83Listed on Tuesday Aug 18, 2026
Description: This pristine, turnkey home is situated in an excellent location, just a short walk, bike ride, or drive to Lake Fairlee. The property features convenient, updated, first-floor living and a flat, fenced-in backyard offering ample space for recreation and pets. Located only 20 minutes from Hanover and its local amenities, including Dartmouth College and Dartmouth-Hitchcock Medical Center (DHMC). This home provides a peaceful, vacation-like setting. Open House: Sunday, August 23 from 1:00 PM - 3:00 PM See Listing Details & 37 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.
$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.
New Listing!
$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.
$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
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.
$349,000 $216 per sq.ft. Woodstock VT Home »
Price Change! Reduced by $90,000 down 26% on August 17th 2026
4 Beds | 2 Baths | Total Sq. Ft. 1617 | Acres: 0.65
Listed on Wednesday Oct 1, 2025
Description: Classic Vermont farmhouse just minutes from the heart of Woodstock. This charming 4 bedroom , 2 bath home offers the character of a traditional New England property with comfortable , move in ready living spaces. The home features a bright eat-in kitchen, spacious dining room, and a welcoming living room with a wood-burning fireplace--perfect for cozy Vermont evenings. Freshly painted interiors and updated flooring provide a clean , inviting feel while preserving the home's classic farmhouse charm. An attached barn/ garage offers excellent storage and flexible space for outdoor gear , a workshop, or hobby area--ideal for those who enjoy Vermont's year-round outdoor lifestyle. Located just a short drive to the Village Green in Woodstock, the property also provides convenient access to hiking, biking, and skiing at nearby Killington Resort. Whether you are seeking a full time residence or a Vermont getaway , this property offers an excellent opportunity to enjoy one of Vermont's most desirable areas at an attractive price point. Call today for a private viewing. See Listing Details & 47 images.
$400,000 $302 per sq.ft. Woodstock VT Home »
2 Beds | 1 Baths | Total Sq. Ft. 1324 | Acres: 0.51Listed on Friday Jul 10, 2026
Description: Once an old school house, this home features stone walls, beautiful gardens, and a nice level yard with a stone patio. The year-round brook cascades over rocks and winds along the back side of the property. A covered porch leads inside, where the main floor offers an eat-in kitchen, a large living room and a dining area with French doors to the outside. There are also two bedrooms, an office with stairs to the basement, a full bath with laundry, and a mudroom. The 2nd floor attic, with a large dormer, offers many possibilities for additional space but requires installing stairs and building out the open area. The basement houses utilities and allows for significant storage. The house needs a few updates but has lots of potential and is a wonderful investment opportunity or a great way to get into a starter home in the Woodstock area. It is conveniently located just minutes from Woodstock Village and only a few miles from the Kedron Valley Inn, the South Woodstock Store, and the Green Mountain Horse Association. See Listing Details & 32 images.
