Windham County VT Homes under $300,000

/46
$210,000
- Land
- 30 Acres
- $6,977 per Acre
184 Schoolhouse Rd, Jamaica, VT 05343

Jamaica, Vermont’s hidden gem! Experience this wonderful 30.1+/- acre forested parcel with views of the local mountains. The land gently slopes to the southeast, perfect for solar, but better yet, utility lines are located along much of the frontage! Bounded on two sides by classic stone walls, there is a woods road that travels through the property making exploration easy. Jamaica has NO local

Curtis Trousdale Preferred Properties

184 Schoolhouse Rd, Jamaica, VT 05343
/7
$235,000
- Land
- 15 Acres
- $15,390 per Acre
0 W Hill Rd, Jamaica, VT 05343

The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 2 is 15.27 acres and is the first parcel found on the left side of the newly built 20 foot

Thom Milke Fountains Land Inc.

0 W Hill Rd, Jamaica, VT 05343
/20
$299,000
- 3 Beds
- 1 Bath
- 1,178 Sq Ft
17 Winter Ct, Brattleboro, VT 05301

Classic Ranch Style Home! Just starting out or thinking of downsizing? This could be the one! Nestled in a sweet neighborhood, this charming ranch offers easy one-level living just minutes from downtown shopping, schools, and recreation. Set on a manageable 0.2 acre lot, this home features a bright enclosed porch/bonus room perfect for morning coffee, reading, or relaxing year-round. Continuing

Liz LaVorgna Berkley & Veller Greenwood Country

17 Winter Ct, Brattleboro, VT 05301
/27
$263,000
- 2 Beds
- 1 Bath
- 1,440 Sq Ft
637 Wiswall Hill Rd, Townshend, VT 05353

Discover your perfect Vermont escape in this cozy two-story cabin nestled on a sweet, level acre. Whether you're looking for a weekend getaway or a full-time residence, this home offers the ideal blend of rustic charm and everyday functionality. The lower level welcomes you into an open-concept guest or living space, with convenient access to utilities and a fenced-in shaded area—perfect for pets

Jessica Landers Barrett and Valley Associates Inc.

637 Wiswall Hill Rd, Townshend, VT 05353
/30
$255,000
- 3 Beds
- 1 Bath
- 1,144 Sq Ft
77 Griswold Dr, Bellows Falls, VT 05101

Nestled on a dead-end street in a sought-after neighborhood, this charming split-level ranch offers both comfort and potential. Featuring three spacious bedrooms and a full bath, the home boasts an inviting layout perfect for modern living. The kitchen opens to a lovely porch—ideal for enjoying your morning coffee or evening relaxation. Set on a generous 0.37-acre lot, there’s plenty of outdoor

Rob Weltz Barrett & Valley Assoc. Inc

77 Griswold Dr, Bellows Falls, VT 05101
/34
$265,000
- 2 Beds
- 1 Bath
- 1,137 Sq Ft
199 Depot Rd, Williamsville, VT 05362

Nestled on 12.4 acres of wooded privacy, this raised ranch at 199 Depot Road offers the best of Vermont living—peaceful, scenic, and just minutes from the village of Newfane. With 2 bedrooms and 1 full bath across 1,137 square feet, this well-maintained home features warm wood accents, abundant natural light, and an open-concept living and dining area that feels bright and inviting.Large

Kate Barry EXP Realty

199 Depot Rd, Williamsville, VT 05362
/16
$275,000
- 2 Beds
- 2 Baths
- 720 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 Alger Real Estate Agency

10 Riverfront Dr, Bellows Falls, VT 05101
/45
$269,000
- 3 Beds
- 1 Bath
- 1,586 Sq Ft
2277 Vermont 30, Jamaica, VT 05343

Meander down the winding private drive and “LO AND BEHOLD” an enchanting country cottage nestled on a serene 4.8 acres awaits you! This quaint 3-bedroom, 1-bath home is brimming with potential. Inside, you'll find wideboard pine flooring in the dining and living rooms, 2 woodstoves, and an additional den area. In 2024, SEVCA conducted an energy service, enhancing the home with spray foam

Elyn Bischof Berkshire Hathaway HomeServices Stratton Home

2277 Vermont 30, Jamaica, VT 05343
/24
$279,900
- 3 Beds
- 2 Baths
- 1,183 Sq Ft
4322 Augur Hole Rd, Brattleboro, VT 05301

Super location! Easy access to Rt 9 and Rt 30 but tucked into nearly a level acre in a lovely country setting. You can tell the previous occupants loved their gardens and a bit of work would restore the blooms to full glory. The pool is a bonus but is waiting for some care to get up and running...The home has emerged from a fun loving schoolhouse filled with learning and joy to a cozy,

Christine Lewis Brattleboro Area Realty

4322 Augur Hole Rd, Brattleboro, VT 05301
/41
$265,000
- 4 Beds
- 1 Bath
- 1,612 Sq Ft
178 Parsons Rd, Wilmington, VT 05363

Charming Cape-style home set on 1.7 beautifully landscaped acres, featuring a detached two-car garage. The expansive yard includes established gardens, a BBQ area, a barn, and two additional sheds in need of some TLC. Located just 4 miles from downtown Wilmington, you’ll enjoy easy access to shopping, dining, and year-round outdoor activities like skiing, golfing, hiking, biking, and boating. The

Jennifer Hovey-Densmore Deerfield Valley Real Estate

178 Parsons Rd, Wilmington, VT 05363
/45
$275,000
- 3 Beds
- 1.5 Baths
- 1,728 Sq Ft
121 Happy Haven Rd, Wilmington, VT 05363

This home offers endless potential to become your ideal retreat. Tucked away on 1.3 acres at the end of a quiet dead-end road, it provides privacy while still being conveniently close to downtown Wilmington and year-round recreation—whether you enjoy skiing, golfing, hiking, biking, or boating. The main level features an open-concept layout with a cozy living room with a wood-burning fireplace, a

Jennifer Hovey-Densmore Deerfield Valley Real Estate

121 Happy Haven Rd, Wilmington, VT 05363
/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

Christine Lewis Brattleboro Area Realty

109 Central St, Brattleboro, VT 05301
/25
$239,000
- 4 Beds
- 2 Baths
- 1,634 Sq Ft
67 Williams Street Extension, Town of Rockingham, VT 05101

This charming and versatile home is on a double village lot at the end of a dead end road in close proximity to the vibrant village of Bellows Falls. This location allows for wonderful privacy in the heart of town and plenty of room for gardening and entertaining. The second floor has three bedrooms, a 3/4 bath and a kitchen, ideally suited for mother-in-law space or it works as a single family

Oona Madden Berkley & Veller Greenwood Country

67 Williams Street Extension, Town of Rockingham, VT 05101
/34
$299,900
- 3 Beds
- 2.5 Baths
- 1,025 Sq Ft
35 Hillcrest Terrace, Brattleboro, VT 05301

Open House August 1, 5:30-7:00 and August 2, 10-11:30. Welcome to 35 Hillcrest Terrace, a well-loved home owned by the same family for over 20 years, perfectly situated in one of Brattleboro’s most convenient neighborhoods. Just moments from Memorial Park, this charming property offers easy access to recreation, walking trails, and town amenities while providing a peaceful, residential

Morriah Adams BHG Masiello Brattleboro

35 Hillcrest Terrace, Brattleboro, VT 05301
/28
$249,000
- 3 Beds
- 1 Bath
- 1,213 Sq Ft
5704 Coolidge Hwy, Guilford, VT 05301

Tucked back off the road, equidistant between Brattleboro, Vermont and Bernardston, MA, this “cute-as-a-button,” chalet-influenced cape is an excellent opportunity for a cozy, 3-bedroom home or an Airbnb, on a 7.9-ac lot in beautiful Guilford, Vermont. Nice mix of sun and shade. Excellent gardening spot. High-speed internet available. Single-level living is possible, with a first-floor

Dan Normandeau Berkley & Veller Greenwood Country

5704 Coolidge Hwy, Guilford, VT 05301
/47
$249,000
- 3 Beds
- 2 Baths
- 1,960 Sq Ft
5 Camelot Dr, Wilmington, VT 05363

This 3-bedroom, 2-bath manufactured home on .43 acres offers flexibility and potential, currently set up as two separate 1-bedroom units—ideal for rental income, guests, or an easy conversion back to a single residence. The property features a nice lawn area, two storage sheds, a one-car garage with plenty of space inside, and a paved driveway for convenience. Located in a quiet section of town

Chad Lackey Deerfield Valley Real Estate

5 Camelot Dr, Wilmington, VT 05363
/40
$224,000
- 2 Beds
- 1 Bath
- 550 Sq Ft
505 Smith Rd, Halifax, VT 05342

Classic Cabin In The Woods! Wonderful Wilderness spot! Feeling of remoteness and SO close to Everything Vermont and Northwestern Mass have to offer. Built in 2006 Hewn from local timber. The open floor plan 20 x 20 Cabin has 2 sleeping lofts and amazingly endless potential. The drilled well is in, water lines are run and a three bedroom state approved septic system is installed. The cabin

Steve Goldfarb Deerfield Valley Real Estate

505 Smith Rd, Halifax, VT 05342
/28
$249,000
- 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
/5
$210,000
- 2 Beds
- 1 Bath
- 560 Sq Ft
1570 Somerset Rd, Wilmington, VT 05363

Somerset Wilderness,Close to the reservoir and Deerfield River. Boating. snowmobiling, hunting, and hiking. Open land with trails and apple trees. Abuts the National Forest.

Mark Yule BHG Masiello Brattleboro

1570 Somerset Rd, Wilmington, VT 05363
/16
$259,900
- Land
- 29 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

Christine Lewis Brattleboro Area Realty

1270 Melendy Hill Rd, Guilford, VT 05301
/23
$245,000
- 1 Bed
- 1 Bath
- 640 Sq Ft
9B Snow Mountain Village Unit 142, Dover, VT 05356

GORGEOUS VIEWS OF MOUNT SNOW from this bright, airy one-bedroom, top-floor, corner condo in Snow Mountain Village, just minutes to the base area! Recent updates to the building include a new roof and new skylights. The interior has been tastefully updated with wood-tone vinyl flooring, plush bedroom carpet, all new LG appliances, quartz countertop and kitchen cabinets, new bathroom vanity, new

Patricia Fitzpatrick Skihome Realty

9B Snow Mountain Village Unit 142, Dover, VT 05356
/34
$289,000
- 2 Beds
- 1.5 Baths
- 1,059 Sq Ft
394 Haystack Rd Unit 2, Wilmington, VT 05363

Enjoy four-season living in this inviting 2-bedroom, 1.5-bath townhome just a short walk to Haystack Golf Course. Set in a peaceful location with direct Valley Trail and snowmobile access, this well-cared-for home is part of a small HOA with low fees. The main level offers a spacious open layout featuring a cozy wood stove on a slate hearth—perfect for watching the fire roar after a day on the

Chad Lackey Deerfield Valley Real Estate

394 Haystack Rd Unit 2, Wilmington, VT 05363
/40
$229,900
- 1 Bed
- 2 Baths
- 848 Sq Ft
11F Snow Tree Ln Unit F, Dover, VT 05356

Be in the heart of the action at the base area of Mount Snow in this light-filled 1-bedroom, 2-bath end unit in the sought-after Snowtree community. Step out your door, stroll across the bridge and parking lot, and hop on the Magic Carpet lift—no need to drive. This well-designed end unit offers extra windows for abundant natural light, a smart floor plan, generous closet space, and two cozy

Chad Lackey Deerfield Valley Real Estate

11F Snow Tree Ln Unit F, 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
$239,000
- Land
- 1.57 Acres
- $152,229 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.

Andrew King Stratton Real Estate

2 Gold Medal Cir, Stratton, VT 05343
/19
$249,000
- Land
- 30 Acres
- $8,275 per Acre
189 North St, Dover, VT 05356

Discover the perfect Vermont retreat on this 30.09 acre wooded parcel, ideally located in the heart of ski country. Tucked away in East Dover, this private lot offers a serene, natural setting just minutes from Mount Snow and The Hermitage Club. Towering hardwoods and softwoods provide a peaceful forest backdrop ideal for building your dream mountain home or cabin escape.Whether you

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

189 North St, Dover, VT 05356
/37
$275,000
- 3 Beds
- 2.5 Baths
- 1,200 Sq Ft
301C Vermont Route 100 Unit C, Dover, VT 05356

Charming 3-bedroom, 2.5-bath condo located just one mile from Mount Snow! This cozy mountain getaway offers views of the slopes from the living room and back deck and offers easy access to the Moover shuttle—just steps away. Inside, you’ll find a warm and welcoming space featuring new granite counter tops in the kitchen and a recently installed heat pump providing efficient heating in the winter

Chad Lackey Deerfield Valley Real Estate

301C Vermont Route 100 Unit C, Dover, VT 05356
/30
$275,000
- Land
- 58 Acres
- $4,761 per Acre
0 Vermont Route 100, Jamaica, VT 05343

Over 57 IMPRESSIVE ACRES located in a NO ZONING town close to Stratton and Mount Snow! Large tract of land with stunning views from multiple locations throughout the property! State wastewater permit already in place and on file with the State of Vermont for construction of a three bedroom home, see permit number WW-2-5317 attached. So many other options available should you want to subdivide or

Julie Lowe Lowe's Real Estate, LLC

0 Vermont Route 100, Jamaica, VT 05343
/28
$205,000
- 2 Beds
- 1 Bath
- 844 Sq Ft
8577 Vermont 30 Unit H, Jamaica, VT 05343

Welcome to The Willows. Where convenience, comfort, and value come together in this well-appointed 2 bedroom, 1 bathroom condominium. Set privately back from Route 30, this thoughtfully maintained unit offers peaceful surroundings just two minutes from Strattons Access Road and within easy reach of Jamaica State Park and the West River.Ideal for first-time homebuyers or those looking to

Tara van de Velde Four Seasons Sotheby's Int'l Realty

8577 Vermont 30 Unit H, Jamaica, VT 05343
/13
$249,000
- Land
- 0.71 Acre
- $350,704 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

Jacki Murano Southern Vermont Realty Group

24 Lower Highlands Rd, Dover, VT 05356
/20
$250,000
- 1 Bed
- 1 Bath
- 640 Sq Ft
3C Snow Mountain Village Unit 113, Dover, VT 05356

The special assessment on this unit has been paid in full! Don’t miss out on this incredible opportunity to own a cozy mountain getaway at Snow Mountain Village! This beautifully updated 1 bed, 1 bath condo offers the perfect balance of comfort and convenience. With breathtaking mountain views right from your first-floor patio, you can relax and enjoy the natural beauty of the area

Carrie Mathews Winhall Real Estate

3C Snow Mountain Village Unit 113, Dover, VT 05356
/19
$299,000
- 3 Beds
- 2 Baths
- 1,248 Sq Ft
8E Dover Green Loop, Dover, VT 05356

Spacious townhome at an incredible price in the Dover Green community located just a short drive or shuttle ride south of Mount Snow. This unit sits nestled towards the top of the development with great privacy and parking, and has had numerous recent upgrades to the roof, foundation, paint, siding, and whole house water filtration. The interior boasts a vaulted great room, wood burning fireplace

Adam Palmiter Berkley & Veller Greenwood/Dover

8E Dover Green Loop, Dover, VT 05356
/27
$289,000
- 2 Beds
- 2 Baths
- 896 Sq Ft
5 Mountain Village Unit 127, Dover, VT 05356

The special assessment for this unit has been paid in FULL!! An overall tremendous value for a prime location and direct Mount Snow views, this bright and spacious 2-bedroom, 2-bath Snow Mountain Village condo offers functionality and amazing convenience. There is Moover shuttle service to the lifts, restaurants, and shops. Upon entering this well maintained unit, is a mudroom for ski gear and

Prema Fitzpatrick Skihome Realty

5 Mountain Village Unit 127, Dover, VT 05356
/9
$225,000
- Land
- 0.73 Acre
- $308,219 per Acre
5 Pinnacle View Rd, Dover, VT 05356

With breathtaking views of Mount Snow, this exceptional 0.73-acre parcel is the perfect setting for your dream mountain retreat. Located in the resort district, short-term rentals are permitted, making this a prime investment opportunity or an ideal family legacy home for generations to enjoy. Just off Route 100, a one-minute drive to the lifts at Mount Snow,an Epic Pass mountain, offering

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

5 Pinnacle View Rd, Dover, VT 05356
/20
$215,000
- 3 Beds
- 1 Bath
- 636 Sq Ft
30 Water St, Jamaica, VT 05343

Discover the Acorn, a picturesque retreat nestled on the banks of the scenic West River in Jamaica, Vermont. This unique home, a beautifully converted sugar shack, offers an enchanting taste of rustic charm, perfect for those seeking a serene getaway. Ideal for nature lovers and outdoor enthusiasts, the Acorn sits close to the renowned ski resorts of Stratton Mountain and Mount Snow, providing a

Daire Gibney Barrett and Valley Associates Inc.

30 Water St, Jamaica, VT 05343
/18
$250,000
- 5 Beds
- 1.5 Baths
- 1,504 Sq Ft
1614 Burbee Pond Rd, West Townshend, VT 05359

Great location for primary or vacation home. Near Burbee Pond in Windhame. 2.6 acres and possibly small commercial. 4 Plus bedrooms with one full bath and a half bath on main floor.Home is ready for your improvements.Close to ski resorts!

Bob Maisey Berkshire Hathaway HomeServices Stratton Home

1614 Burbee Pond Rd, West Townshend, VT 05359
/22
$289,000
- 3 Beds
- 2 Baths
- 1,512 Sq Ft
6738 Vermont Route 100, Wardsboro, VT 05355

This charming 1500 square foot manufactured home, located just over 3 miles from Mount Snow Ski Resort and a 15-minute drive to Stratton Mountain Resort, offers a perfect blend of comfort and convenience for mountain enthusiasts. 3 bedrooms and 2 bathrooms, this home provides ample space for family or guests. Inside, the open-plan living area is both cozy and spacious, featuring warm wood

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

6738 Vermont Route 100, Wardsboro, VT 05355
/10
$250,000
- Land
- 23 Acres
- $10,823 per Acre
184 Dupre Dr, Guilford, VT 05301

Here's a large 23.10 +/- acre parcel that's mostly wooded but with a little bit of open field and possible short range local views. Conveniently located within a few minutes of town, here's an opportunity to enjoy country living while having access to modern amenities. There's a lot of potential for the right buyer! Please respect the privacy of the other houses on the road past this land.

A.J. Bellville Bellville Realty

184 Dupre Dr, Guilford, VT 05301
/29
$225,000
- Land
- 34 Acres
- $6,618 per Acre
0 Hillside Dr Unit 4998188, Wilmington, VT 05363

Discover Your Private Vermont Retreat – 34 Acres of Possibility and PeaceA rare opportunity awaits to own an expansive 34.0-acre parcel offering tremendous privacy, breathtaking views, and endless potential. Nestled amidst rolling topography with picturesque stone walls and a network of historic trails, this unique property invites exploration and inspiration at every turn. Two potential

Monique White Deerfield Valley Real Estate

0 Hillside Dr Unit 4998188, Wilmington, VT 05363
/8
$235,000
- Land
- 0.32 Acre
- $734,375 per Acre
8 A Freestyle Cir, Dover, VT 05356

Ski in and out at Mount Snow from one of the last two buildable lots. In other words, if you like the convenience of slopeside living this could be the location for you to build your dream home with easy access to the mountain. 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

John Redd Skihome Realty

8 A Freestyle Cir, Dover, VT 05356

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Copyright 2025 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.