36

Windham County VT Homes under $300,000

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  • /79

    $275,000

    • Land
    • 22.32 Acres
    • $12,321 per Acre

    81 Parish Hill Rd Unit 26, Newfane, VT 05345

    Tucked away in the quiet hills of South Newfane, Vermont, this property presents an excellent opportunity to own a secluded off-grid retreat with endless potential. Spanning 22.32 acres of mixed timberland, the land offers both natural beauty and outdoor recreation, while the cabin provides a comfortable base that is already well on its way to completion.The cabin itself measures 715 square feet

    Chad Bruyette Whitetail Properties Real Estate

    81 Parish Hill Rd Unit 26, Newfane, VT 05345
  • /17

    $285,000

    • 1 Bed
    • 1 Bath
    • 1,320 Sq Ft

    116 Birge St Unit 2, Brattleboro, VT 05301

    Simple but elegant! Historic posts and wonderful beams define the magnificent open concept, giving visual shape and creating traditional options or whimsical uses for your new lifestyle. High ceilings and huge windows create a celebration of light, complementing the glowing antique floors—magical in combination and truly beautiful. A home, an artist loft...so many uses, so unique, so

    Christine Lewis Brattleboro Area Realty

    116 Birge St Unit 2, Brattleboro, VT 05301
  • /18

    $285,000

    • 2 Beds
    • 1 Bath
    • 960 Sq Ft

    3095 Thompsonburg Rd Unit B/2, Londonderry, VT 05155

    Close to Magic, Bromley and Stratton! This two-bedroom, one bath condo with woodburning fireplace overlooks a beautiful brook and tennis court area. Private deck out back to enjoy some sun. Eat in kitchen with pass through countertop area opens into the living room. Manageable and spacious for a nice weekend getaway or make this your fulltime home. Just minutes to downtown with shopping, fuel,

    Julie Lowe Lowe's Real Estate, LLC

    3095 Thompsonburg Rd Unit B/2, Londonderry, VT 05155
  • /16

    $275,000

    • 2 Beds
    • 2 Baths
    • 1,440 Sq Ft

    10 Riverfront Dr, Bellows Falls, VT 05101

    This recently renovated home is located on and with gorgeous views of the Connecticut River, frontage suitable for a wharf. Two bedrooms, two full baths and a beautifully crafted stone and brick fireplace. A large, private backyard, inviting family gatherings, just minutes to I91 and Okemo Mountain. Motivated Seller

    Gale Alger

    10 Riverfront Dr, Bellows Falls, VT 05101
  • /32

    $229,000

    • 1 Bath
    • 475 Sq Ft

    11C Snow Tree Ln Unit Birches 11C, Dover, VT 05356

    Discover effortless mountain living in this beautifully updated studio condominium that is walking distance to the slopes and in the desirable Snow Tree community. Perfect for weekend getaways, seasonal escapes, or as a high performing rental investment. This home boasts an extremely strong rental history supported by a documented 3 year history of over $25,000 annually and is being offered fully

    Melissa Ellis Southern Vermont Realty Group

    11C Snow Tree Ln Unit Birches 11C, Dover, VT 05356
  • /36

    $269,000

    • 1 Bed
    • 1 Bath
    • 2,000 Sq Ft

    116 Birge St Unit 3, Brattleboro, VT 05301

    Huge price reduction! Welcome to Esteyville! Here, history, location, and distinctiveness excel. This rare, NYC loft-style condo on the 3rd and 4th floors was formerly home to Estey Organ, the world's largest pipe organ manufacturer, circa 1870. Listed in the National Registry of Historic Places, you will find original pine wide-plank floors, exposed post-and-beam construction, soaring ceilings,

    Liz LaVorgna Brattleboro Area Realty

    116 Birge St Unit 3, Brattleboro, VT 05301
  • /32

    $239,000

    • 2 Beds
    • 1.5 Baths
    • 1,160 Sq Ft

    11 Hassey Bend Unit 9, Wilmington, VT 05363

    Ready to move in Mountain Ponds end unit Townhouse with 2 bedroom plus loft and 1 1/2 bathsMain level boasts an open concept living/dining and renovated kitchen area. Relax on the back deck off dining area. Gas stove in the living room. Attached ski locker/wood bin with 2 entrances. Spacious mudroom. Direct access to VAST snowmobile trail and adjacent to Haystack Golf Course. Lake Whitingham is

    Jennifer Hovey-Densmore Deerfield Valley Real Estate

    11 Hassey Bend Unit 9, Wilmington, VT 05363
  • /28

    $235,000

    • 2 Beds
    • 1 Bath
    • 970 Sq Ft

    3153 Vermont Route 100, Wardsboro, VT 05355

    Charming 2-bedroom, 1-bath rustic cottage featuring a versatile 14x9 mudroom and plenty of recent upgrades. The spacious kitchen flows into a generous dining area, while the cozy living room offers a VT Castings woodstove, a side bar with stools, and warm, inviting finishes. Both bedrooms are nicely sized, with one offering sliding doors that open directly to the backyard—perfect for easy outdoor

    Jennifer Hovey-Densmore Deerfield Valley Real Estate

    3153 Vermont Route 100, Wardsboro, VT 05355
  • /39

    $295,000

    • 4 Beds
    • 1 Bath
    • 1,248 Sq Ft

    552 - 554 Hinesburg Rd, Brattleboro, VT 05301

    Unique opportunity to own a nearly 40 acre tract and 2 homes on Hinesburg Road in a great West Brattleboro location. The homes sit unseen approximately 500 feet back on a private driveway from the public road. The houses need a fair amount of repair and remodeling to get them in good condition. The main house is a cape style home with open concept kitchen/dining/living room, full bath, and 2

    Steve Schoppmeyer BHG Masiello Brattleboro

    552 - 554 Hinesburg Rd, Brattleboro, VT 05301
  • /48

    $294,000

    • 5 Beds
    • 3 Baths
    • 2,360 Sq Ft

    5 Reynolds Dr, Brattleboro, VT 05301

    Turn-Key Investment in the Heart of Brattleboro! This versatile three-unit multifamily property offers a rare "move-in ready" opportunity for both savvy investors and owner-occupants. Two of the three units have been recently and extensively renovated, featuring brand-new flooring, fresh paint, modern baseboards, and updated plumbing and light fixtures. With new toilets and stainless/modern

    Kate Barry EXP Realty

    5 Reynolds Dr, Brattleboro, VT 05301
  • /33

    $249,000

    • 2 Beds
    • 1 Bath
    • 1,004 Sq Ft

    662 Vt Route 30, Newfane, VT 05345

    Whether you’re just starting out with your first home or looking to downsize and simplify, this sweet home is just the right size. It features two bedrooms plus bonus room upstairs, with a full bathroom conveniently located on the first floor. The kitchen is charming, complete with a dishwasher, newer refrigerator and stove, opens to a dining area, and a spacious living room with beautiful wood

    Rebecca Seymour Brattleboro Area Realty

    662 Vt Route 30, Newfane, VT 05345
  • /29

    $235,000

    • Land
    • 33.48 Acres
    • $7,019 per Acre

    0 Vt Route 100 Unit 5072614, Londonderry, VT 05155

    Beautiful 33.48 acre building lot in Londonderry. Some views possible and some clearing has been done. There are some wetlands on property but various choices for building sites exist. South East Facing

    Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    0 Vt Route 100 Unit 5072614, Londonderry, VT 05155
  • /2

    $249,000

    • Land
    • 1.29 Acres
    • $193,023 per Acre

    350 Route 100, Dover, VT 05356

    Amazing opportunity to have a building lot near Mount Snow with huge view potential, no HOA restrictions, and easy access off a main paved road. This unique site is being offered for the first time in a long time and could be the ideal spot to build your dream Vermont home.

    Adam Palmiter Berkley & Veller Greenwood/Dover

    350 Route 100, Dover, VT 05356
  • /36

    $289,000

    • 1 Bed
    • 2 Baths
    • 895 Sq Ft

    13 Snowtree Ln Unit Willows K, West Dover, VT 05356

    Just a short walk over bridge by Maples Building to the lifts at Mount Snow via the magic carpet, this stunning loft-style, fully remodeled Snowtree condo offers modern comfort and undeniable charm. The open-concept living area features vaulted ceilings, gleaming bamboo floors, and a cozy wood-burning fireplace. A glass slider leads to a private balcony overlooking a babbling brook and peaceful

    Jennifer Hovey-Densmore Deerfield Valley Real Estate

    13 Snowtree Ln Unit Willows K, West Dover, VT 05356
  • /44

    $279,900

    • 4 Beds
    • 1.5 Baths
    • 1,800 Sq Ft

    10 King St, Bellows Falls, VT 05101

    Discover the ideal balance of privacy and convenience in this welcoming 4-bedroom, 2-bath home in the heart of Bellows Falls. Set on a spacious 1-acre lot, the 1,800-sq-ft interior provides generous room for comfortable everyday living. A private garage and secluded yard offer both practicality and serenity, while the large covered porch invites year-round enjoyment of the outdoors. With

    Floyd Amidon Maple Leaf Realty

    10 King St, Bellows Falls, VT 05101
  • /14

    $210,000

    • Land
    • 35 Acres
    • $6,000 per Acre

    00 Vermont Route 100, Jamaica, VT 05343

    Discover the beauty and tranquility of this picturesque wooded parcel—approximately 35 acres—nestled along the serene Deerfield River and spanning the border of Jamaica and Wardsboro. Perfectly situated within easy reach of Mount Snow, Stratton, and Bromley, the property offers convenient access to year-round recreation while preserving the sense of peace and privacy that only a large forested

    Patrice Schneider Southern Vermont Realty Group

    00 Vermont Route 100, Jamaica, VT 05343
  • /43

    $299,000

    • 6 Beds
    • 5 Baths
    • 3,942 Sq Ft

    2072 N Main St, Londonderry, VT 05148

    This is your chance to own in downtown Londonderry! You have the option of commercial, residential or BOTH. One unit is currently set up for residential use with living area and 3/4 bath on the first level and three bedrooms and full bath on the second floor. The second unit has been used for commercial use in the past with open space and 1/2 bath on the first floor with 3 rooms and 2 full baths

    Catherine Cairns Maple Leaf Realty

    2072 N Main St, Londonderry, VT 05148
  • /39

    $285,000

    • 3 Beds
    • 1.5 Baths
    • 1,248 Sq Ft

    70 Overlook Dr, Londonderry, VT 05148

    Welcome Home!!! Located close to town but in a private and quiet area, this property offers an affordable option for locals and first-time homebuyers who want to be in one of Vermont’s best little communities and are willing to make the time and investment to turn this house into a home. The house is solid and has been well-maintained, and there are three bedrooms and 1.5 bathrooms and a nice

    Claudia Harris Mary Mitchell Miller Real Estate

    70 Overlook Dr, Londonderry, VT 05148
  • /12

    $249,000

    • Land
    • 19.6 Acres
    • $12,704 per Acre

    227 Gault Rd, Wardsboro, VT 05355

    This property is ready for you to push the pedal down and Go. All the engineering work has been done! There is an inground 3 bedroom septic system, a drilled well and a long gravel driveway with culverts.With almost half of the 19 acres being cleared, there is massive solar potential here for off the grid living. There is a large shed/cabin at the beginning of the driveway, which you could

    Victoria Woods Brattleboro Area Realty

    227 Gault Rd, Wardsboro, VT 05355
  • /9

    $269,000

    • Land
    • 54.8 Acres
    • $4,909 per Acre

    0 Townshend Dam Rd Unit 5066172, Wardsboro, VT 05355

    Explore the potential of this beautiful 53.8-acre parcel just 3.5 miles from the scenic Townshend Dam. This expansive property offers a peaceful, wooded setting with ample privacy—ideal for recreation, a possible future homesite, or continued forest management. Currently enrolled in Vermont’s Current Use Program, the land offers significant tax savings and can remain in the program under new

    Carrie Mathews Winhall Real Estate

    0 Townshend Dam Rd Unit 5066172, Wardsboro, VT 05355
  • /18

    $299,000

    • Land
    • 1.06 Acres
    • $282,075 per Acre

    12 Someday Rd, Dover, VT 05356

    Located in the prestigious Someday neighborhood of West Dover,VT this 1.06-acre building lot offers a unique opportunity to create your dream home with breathtaking views of Mount Snow ski resort. The lot, which once housed the original Someday homestead as your footprint, it is now ready for its next chapter. With a permit for sewer in place for a 6-bedroom home, the property provides a head

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    12 Someday Rd, Dover, VT 05356
  • /3

    $275,000

    • 4 Beds
    • 2 Baths
    • 2,000 Sq Ft

    2173 Vermont 8a, Whitingham, VT 05361

    4 bedroom 2 bath home located on 4.7 acres. Has a ground level access. Level parking and garden spots. There are huge White Pine trees surrounding this home. Showings delayed until September 29, 2025 to allow for cleaning. License to Sell is needed and in progress, Expected in October.

    Mark Yule BHG Masiello Brattleboro

    2173 Vermont 8a, Whitingham, VT 05361
  • /59

    $275,000

    • 2 Beds
    • 1 Bath
    • 715 Sq Ft

    81 Parish Hill Rd, Newfane, VT 05345

    Nestled in the hills of South Newfane, Vermont, this off-grid property offers the perfect balance of seclusion, recreation, and comfort. Set on 22.32± acres of mixed timberland, the land features a meandering creek, wildlife habitat, and excellent hunting opportunities for deer and turkey. A 715 sq. ft. cabin, approximately 80% complete, serves as the centerpiece of the property. Built with a

    Chad Bruyette Whitetail Properties Real Estate, LLC

    81 Parish Hill Rd, Newfane, VT 05345
  • /2

    $300,000

    • 4 Beds
    • 2 Baths
    • 1,808 Sq Ft

    109 Central St, Brattleboro, VT 05301

    Bright Sunny, south facing! 2 stacked flats just perfect for multi generational living! Inside access with both formal front stair and back utility stairs, so easy for caring for family members, or a plan for aging in place with a care giver. Rent one or both for a money maker. This owner is owner occupying both flats. Plenty of off street parking, a sweet side porch and just a bit of a yard to

    Christine Lewis Brattleboro Area Realty

    109 Central St, Brattleboro, VT 05301
  • /15

    $292,000

    • 2 Beds
    • 2 Baths
    • 1,000 Sq Ft

    5 First Ln Unit 1, Wilmington, VT 05363

    Owner open to offers. Lovely 2 bedroom condo as close as you can get to the 1st tee at the Haystack Golf Club, with winter views over the course to the mountains and sunsets beyond. This practical unit sits conveniently right on one of the best courses in New England, and a short drive from the village of Wilmington, nearby lakes, and Mount Snow and Hermitage Club ski resorts. Inside you are

    Adam Palmiter Berkley & Veller Greenwood/Dover

    5 First Ln Unit 1, Wilmington, VT 05363
  • /16

    $259,900

    • Land
    • 29.2 Acres
    • $8,901 per Acre

    1270 Melendy Hill Rd, Guilford, VT 05301

    A rare find! This amazing land has long range views, privacy and close to everything! There is a right of way for egress, and will be perfect for an off grid tuck away cabin or primary. A small meadow is part of the 2 acre exemption for house site, just at the end of the existing drive...easy to get to and just the beginning of the land. Mostly Black Birch, Sugar Maple and Hemlock, there is a

    Christine Lewis Brattleboro Area Realty

    1270 Melendy Hill Rd, Guilford, VT 05301
  • /12

    $235,000

    • Land
    • 18.93 Acres
    • $12,414 per Acre

    0 Forest Heights Rd, West Dover, VT 05356

    Are you ready to turn your dream home into a reality? This expansive parcel of land, located just 2 miles from the slopes of Mount Snow, is waiting for your vision. The property offers an ideal combination of privacy and seclusion and with some clearing, you can unveil extraordinary views of the Mount Snow ski slopes, creating the perfect backdrop for your dream home. The property boasts

    Michelle O'Neil Deerfield Valley Real Estate

    0 Forest Heights Rd, West Dover, VT 05356
  • /11

    $250,000

    • Land
    • 18 Acres
    • $13,889 per Acre

    0 Melendy Hill Rd Unit 5046973, Guilford, VT 05301

    Tucked in the gently rolling hills of Vermont, this is a sweet spot to build your new home. Located on a class 3 privately maintained road, there are power poles the length of the road with fiber optics ready for the streamers or work at home folks. Build on the road for a short drive and utility ease, or take the secluded route and tuck away in the forest. The acreage is an educated guess and

    Christine Lewis Brattleboro Area Realty

    0 Melendy Hill Rd Unit 5046973, Guilford, VT 05301
  • /6

    $229,000

    • Land
    • 1.57 Acres
    • $145,860 per Acre

    2 Gold Medal Cir, Stratton, VT 05343

    This lot is only one mile from the Stratton Mountain Resort's Sun Bowl base area. The lot has views of Stratton's ski trails. The Powers Subdivision has 11 lots in total and 2.71 acres of common land. Additionally, there is 69 acres of conservation land making this community very private. Build your 4-bedroom dream home right here in one of the best planned communities in southern Vermont. Find

    Andrew King Stratton Real Estate

    2 Gold Medal Cir, Stratton, VT 05343
  • /13

    $209,000

    • Land
    • 0.71 Acre
    • $294,366 per Acre

    24 Lower Highlands Rd, Dover, VT 05356

    Exceptional development opportunity just two minutes from the Mount Snow base area. This 0.71-acre parcel is fully approved for a four-unit residence with occupancy for 16. State wastewater and town construction permits are secured, and full architectural and structural engineering plans will convey. All approvals are valid for the next two years, allowing for immediate construction. With site

    Jacki Murano Southern Vermont Realty Group

    24 Lower Highlands Rd, Dover, VT 05356
  • /10

    $299,000

    • Land
    • 7.08 Acres
    • $42,232 per Acre

    103 Schoolbus Depot Rd, Town of Rockingham, VT 05101

    Located between Chester and Bellows Falls, just a mile from exit 6 off I-91, the opportunity for development awaits your ideas. Easy access, level parcel for either commercial ventures, gardens, or home. Land consists of two parcels separated by School Bus Depot Road totaling 7.08 acres. The island parcel gives excellent exposure to Route 103 for terrific signage. 103 is a high traffic corridor

    Heidi Bernier Berkley & Veller Greenwood Country

    103 Schoolbus Depot Rd, Town of Rockingham, VT 05101
  • /3

    $299,000

    • Land
    • 0.84 Acre
    • $355,952 per Acre

    8 B Freestyle Cir, Dover, VT 05356

    Ski in and out at Mount Snow from one of the last two buildable lots on the mountain. If you understand the convenience of slopeside living this could be the location for you to build your dream home. This building site is part of the TrailsEdge PUD, sharing in their utilities and ski access to/from Mount Snow through the Snowdance Village ski trails. Note that this is the larger of 2 lots

    John Redd Skihome Realty

    8 B Freestyle Cir, Dover, VT 05356
  • /9

    $250,000

    • Land
    • 3.79 Acres
    • $65,963 per Acre

    000 Fort Dummer Heights, Brattleboro, VT 05301

    Easy to build!!! The land is open, so no fuss with a lot of prep. Beautiful high meadow, in a nice little neighborhood tucked up against the state park, what more could you want? This land has gone thru several transitions and plans for development by it's builder owner, but we now have the simplest! There are potentially a couple of options for hooking to town sewer with neighbor cooperation.

    Christine Lewis Brattleboro Area Realty

    000 Fort Dummer Heights, Brattleboro, VT 05301
  • /5

    $270,000

    • 6 Beds
    • 2 Baths
    • 2,112 Sq Ft

    556 S Main St, Brattleboro, VT 05301

    What a great way to start your home ownership! A tenant can help with the monthly expenses letting you build your own reserves and take a bit ofpressure off the cost of home ownership! This 2 family has two-3 bedroom units, a nice yard and off street parking. Check it out and see for yourself...please respect the 48 hour notice for tenants, mask up! No interior photos due to tenant privacy.

    Christine Lewis Brattleboro Area Realty

    556 S Main St, Brattleboro, VT 05301
  • /51

    $244,900 Coming Soon

    • 2 Beds
    • 1.5 Baths
    • 1,056 Sq Ft

    72 Morningside Commons, Brattleboro, VT 05301

    Move up to a designer condo! Impeccable detailing by an IKEA design team raised this unit to a high level of quality. From the marble floor entrance to the architectural ceiling over the dining area to the custom kitchen and bathroom installations to the decorator lighting to the PAX closet wardrobe systems... it all speaks "beautiful". Newer features include a propane boiler and hot water heater

    Sally Fegley BHG Masiello Brattleboro

    72 Morningside Commons, Brattleboro, VT 05301
  • /40

    $214,900

    • 5 Beds
    • 3.5 Baths
    • 3,600 Sq Ft

    2139 Vt Route 30, Townshend, VT 05353

    Great days ahead for the buyer of this stately, manor styled home on close to three (3) acres. You have to see the interior to believe it. Dated? Yes, but solid bones. Crazy nice wood floors, classic built-ins & style. So many 'nooks & crannies. Cavernous, dry & clean basement. Exterior: 'challenged', but I have all the bids to bring it to 'good' condition & the techies are ready to complete

    Robert Balewicz Evergreen Realty of Vermont

    2139 Vt Route 30, Townshend, VT 05353
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