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
/29
$290,000
- 3 Beds
- 1 Bath
- 1,392 Sq Ft
403 Tyler Hill Rd, Vernon, VT 05354

Welcome to this sweet and inviting 3-bedroom, 1-bath home, beautifully updated around 2015 and ready for new memories! Nestled on a generous lot, this home offers both comfort and functionality with a bright, open layout and thoughtful improvements throughout.Enjoy relaxing or entertaining on the deck overlooking a spacious yard with a babbling brook—perfect for peaceful mornings or summer

Kerry Mulverhill Brattleboro Area Realty

403 Tyler Hill Rd, Vernon, VT 05354
/45
$295,000
- 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 Open Sun 11AM - 1PM
- 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
/60
$260,000
- 3 Beds
- 2 Baths
- 1,250 Sq Ft
111 Binney Brook Rd Unit M581, Wilmington, VT 05363

Nice location on the Hill! Featuring a fairly level lot, seasonal views from the deck, a vaulted ceiling in the living room, along with a wood-burning fireplace and adjacent dining area, which is next to the kitchen. Original wood paneling and detailing are intact, a compact galley kitchen, shower bath and two bedrooms on the main upstairs level. The lower walkout level has a bedroom, full bath

Sigrid Pickering Chimney Hill Realty

111 Binney Brook Rd Unit M581, Wilmington, VT 05363
/32
$275,000
- 3 Beds
- 1.5 Baths
- 1,440 Sq Ft
119 Upper Meadows Rd, Bellows Falls, VT 05101

MOTIVATED SELLER! This sweet home built in 1799 sits on seven acres of land, mostly surrounded by woods. Located on a dead-end road, you'll find yourself immersed in the peaceful sounds of nature with lots of privacy. Ample parking is available, and the property offers a large yard to enjoy. Just a seven-minute drive into Bellows Falls and four minutes to I-91, you'll be close to everything

Heather Gleim CENTURY 21 North East

119 Upper Meadows Rd, Bellows Falls, VT 05101
/23
$295,000
- 3 Beds
- 2 Baths
- 1,473 Sq Ft
2705 Vermont Route 100, Wardsboro, VT 05355

Welcome to this charming 3 bedroom home with great river frontage on the Wardsboro brook, situated along Vermont's Route 100 National Scenic Byway. With lots of windows and beautiful wood flooring, the home is very bright and cozy. There's a pellet stove to keep you extra warm when the Vermont winter sets in, and plenty of space to rest your head with two comfy bedrooms and one huge oversized

Mike Masters Four Seasons Sotheby's Int'l Realty

2705 Vermont Route 100, Wardsboro, VT 05355
/46
$299,900
- 6 Beds
- 4 Baths
- 3,581 Sq Ft
27 Westminster Terrace, Bellows Falls, VT 05101

Don't miss this rare opportunity to own a 3-story Victorian multi-family home, perfectly situated in the heart of town. This classic property features four fully occupied rental units generating a solid net income of $32,142 per year. Unit #4 is not fully independent as it has no kitchen and shares the kitchen with family members renting unit 1 . Each unit showcases original hardwood floors,

Jon Tourville BHG Masiello Brattleboro

27 Westminster Terrace, Bellows Falls, VT 05101
/33
$235,000 Open Mon 1PM - 3PM
- 2 Beds
- 2.5 Baths
- 2,112 Sq Ft
116 Morningside Commons, Brattleboro, VT 05301

Yes! A coveted first floor single level unit! And not only that but an end unit, sweetly tucked away for privacy! Just follow the tree and flower lined path right to your door!2 bedrooms, one ensuite, with an additional bedroom, bath, large eat in kitchen, living room, and a stackable washer/dryer, all on the first floor! There are only a few condos here that have finished basement space and this

Rebecca Seymour Brattleboro Area Realty

116 Morningside Commons, Brattleboro, VT 05301
/19
$230,000
- 3 Beds
- 1 Bath
- 900 Sq Ft
373 Brookline Rd, Athens, VT 05143

Tucked away on 16 wooded acres in the quiet hills of Athens, Vermont, this unique property offers the kind of peace that’s getting harder to find. At its center is a simple, charming cabin with an open floor plan and vaulted ceiling, set just above a beaver pond that draws in wildlife and reflects the changing sky. It’s quiet here—really quiet. The kind of place where time slows down and the

Daire Gibney Barrett and Valley Associates Inc.

373 Brookline Rd, Athens, VT 05143
/38
$235,000
- 2 Beds
- 1.5 Baths
- 1,056 Sq Ft
81 Morningside Commons, Guilford, VT 05301

The moment you step into this condo, you notice its unique features and feel a sense of calm. In the living room, you’ll enjoy the “Anywhere” ethanol fireplace for its ambience and extra heat - with no connections, venting or emissions to worry about! The kitchen has been carefully redone, with expanded cabinetry and improvements to the layout and lighting, including a custom display cabinet and

Victoria Woods Brattleboro Area Realty

81 Morningside Commons, Guilford, VT 05301
/17
$201,400
- Land
- 2.80 Acres
- $71,929 per Acre
37 Fred Houghton Rd, Putney, VT 05346

Just in time! So special! This unusual offering was a beloved family complex for many years. The land is a delight of mixed hardwoods and evergreens, easy to walk and gently rolling for intrigue. Walk to "downtown" Putney for the small town energy, pop in the auto for a short drive to everything else...interstate access, NH, skiing...hospitals and services.....or tuck in at home for a

Christine Lewis Brattleboro Area Realty

37 Fred Houghton Rd, Putney, VT 05346
/17
$225,000
- 3 Beds
- 2 Baths
- 1,414 Sq Ft
2147 N Main St, Londonderry, VT 05148

Terrific in-town location! Improvements include new roof and trim last year, 24kw Generator, serviced annually, new flooring on first level and new washer and dryer. Easy to maintain yard space, walk to the plaza for shopping and restaurants, minutes to 3 ski resorts!

Lisa Kelley Cummings & Co

2147 N Main St, Londonderry, VT 05148
/29
$299,000
- 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
/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 envision a

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

189 North St, Dover, VT 05356
/35
$225,000
- Land
- 12 Acres
- $18,160 per Acre
712 Stimpson Hill Rd, Whitingham, VT 05361

Discover this stunning and private 12+ acre parcel, bathed in sunshine and nestled on a quiet dead-end road. Featuring a beautiful open meadow framed by classic stone walls, this idyllic setting offers the perfect location for building your dream home. The property comes ready with essential infrastructure, including; State of Vermont wastewater permit with an approved septic design for a

Monique White Deerfield Valley Real Estate

712 Stimpson Hill Rd, Whitingham, VT 05361
/37
$299,000
- 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
/28
$239,000
- 3 Beds
- 1.5 Baths
- 1,531 Sq Ft
316 Putney Rd, Brattleboro, VT 05301

Convenient Location & Low Maintenance Living! Enjoy easy access to shopping, public transportation and waterfront with scenic trails. The backyard is just the right size for enjoying nature and a little fresh air. This charming home combines classic character with practical updates featuring a standing seam roof, vinyl windows and aluminum siding. Inside, the home radiates its original charm

Kerry Mulverhill Brattleboro Area Realty

316 Putney Rd, Brattleboro, VT 05301
/45
$295,000
- 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
/33
$249,000
- 2 Beds
- 1 Bath
- 1,000 Sq Ft
290 Old Mill Ln, Wilmington, VT 05363

“The Camp” Are you looking for that special seasonal getaway? Look no further! This charming 1-bedroom on the main level and second bedroom upstairs sleeping loft is located in the beautiful town of Wilmington. Nestled in the woods, this cozy cabin offers a unique and special Vermont experience. Enjoy the covered front porch and large deck, perfect for entertaining friends and family. Just steps

Richard Caplan Deerfield Valley Real Estate

290 Old Mill Ln, Wilmington, VT 05363
/48
$235,000
- 2 Beds
- 1.5 Baths
- 1,056 Sq Ft
145 Morningside Commons, Brattleboro, VT 05301

A touch of class at Morningside Commons! This condo exudes comfort and style from the flowering trees in front through the tasteful interior to the shaded patio in the rear. Updated features include laminate floors, newer carpeting on the stairs, newer cabinetry, ceiling fans in the kitchen and master bedroom, and blinds on all the windows. The community pool and tennis/pickleball courts are only

Sally Fegley BHG Masiello Brattleboro

145 Morningside Commons, Brattleboro, VT 05301
/17
$299,000
- 2 Beds
- 2 Baths
- 924 Sq Ft
5 Mountain Village, Dover, VT 05356

Renovated, flexible-use condo in a prime Mount Snow location—just minutes from the base area and on the mountainside of the access road! This 2-bedroom, 2-bath layout is ideal for vacation use or rental income, with a private suite that functions as a lockout unit. Use one side and rent the other, rent both, or enjoy as a full 2-bedroom unit—simply open or close the interior connecting doors. The

Erica Reynolds Southern Vermont Realty Group

5 Mountain Village, Dover, VT 05356
/30
$299,000
- Land
- 58 Acres
- $5,177 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
/8
$220,000
- 3 Beds
- 2 Baths
- 2,262 Sq Ft
570 Rockingham Rd, Bellows Falls, VT 05101

What a great opportunity! This property in its heyday was a thriving Gift Shop and small campground, the owners lived on premises in a charming dormered cape. It has since fallen in disrepair but offers endless opportunity to the right person! The house is a three bedroom cape with a small attached studio apartment and a two car garage with a level, sunny,and private yard. The Gift Shop is almost

Oona Madden Berkley & Veller Greenwood Country

570 Rockingham Rd, Bellows Falls, VT 05101
/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 purchase

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 site

Jacki Murano Southern Vermont Realty Group

24 Lower Highlands Rd, Dover, VT 05356
/18
$230,000
- 1 Bed
- 2 Baths
- 848 Sq Ft
11B Snow Tree Ln Unit Birches B, Dover, VT 05356

Amazing nearby access directly across to the magic carpet at Mount Snow! This lovely updated Snowtree condo is located at the base of the Mount Snow ski resort with easy access to the mountain, as well as convenient amenities and full maintenance for peace of mind. This unit has been renovated to be more functional for sleeping and entertainment than a typical one bedroom. There is a large living

Adam Palmiter Berkley & Veller Greenwood/Dover

11B Snow Tree Ln Unit Birches B, 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
$294,000
- 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
/19
$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
/4
$250,000
- Land
- 1.57 Acres
- $159,236 per Acre
0 Gold Medal Cir Unit 5023219, Stratton, VT 05155

This is lot #1 in the Powers Subdivision, which is the closest lot to Mountain Rd, giving you access to Stratton's Sunbowl entrance less than a mile away. Lot #1 is 1.57 acres and has views of Stratton Mountain. This Gold Medal Circle area of the Powers Subdivision has 11 lots, 2.71 acres of common land with a pond, and 69.06 of conservation land.Permits are in place with the State of Vermont and

Ross Powers TPW Real Estate

0 Gold Medal Cir Unit 5023219, Stratton, VT 05155
/22
$299,000
- 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 this

John Redd Skihome Realty

8 A Freestyle Cir, Dover, VT 05356
/9
$250,000
- Land
- 3.79 Acres
- $65,963 per Acre
000 Fort Dummer Heights Unit 1 and 2, 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 Unit 1 and 2, Brattleboro, VT 05301

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