Windham County VT Homes under $400,000

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 3 is 34.53 acres, and is mostly forested near the access road. A driveway would need to be

Thom Milke Fountains Land Inc.

Charming and meticulously maintained, this classic Vermont A-frame with a tasteful addition offers the perfect blend of character and comfort. Nestled on just under 2 acres, the home features 3 cozy bedrooms, warm wood accents, and inviting living spaces filled with natural light. Whether you're enjoying a quiet morning on the deck or taking in the peaceful surroundings, this property is a true

Carrie Mathews Winhall Real Estate

This charming, updated 3-bedroom, 2-bath Cape style home sits on 0.17 acres in the heart of Vermont's ski country. Filled with natural light, the warm and inviting interior features a main-level bedroom, while two additional upstairs bedrooms are perfect for guests. After a day on the slopes, unwind by the cozy gas fireplace. Enjoy your morning coffee on the covered porch, or spend evenings

Cassandra Ehrlich BHG Masiello Brattleboro

Slow down and take time to soak up the charm and character of this sweet house in the beautiful town of Windham! The c. 1860 antique Country Cape is a true testament to the enduring appeal of fine craftsmanship and a life well-lived. The house sits on 12 acres, with a stream and flower-filled meadows beyond, and one of the best front porches in Windham – relax, enjoy the view, and watch the world

Claudia Harris Mary Mitchell Miller Real Estate

This charming home in Grafton is centrally located next to the MKT market, offering easy access to the post office, town offices, library, school, inn, church, and local shops. With spacious and bright rooms, the home welcomes you into a main foyer that features a living room and study as its two front rooms. A dining room adjoins the living room and leads to the kitchen at the back of the house.

Jessica Landers Barrett and Valley Associates Inc.

Perfect! If you have been looking for a workshop or studio, this is the perfect set up. 30x40, this huge open building has workshop benches, heat, electricity, water hook ups. There is a potential to hook to the septic....even create a 1 bedroom apartment. On top of this great find, there is a 2 car detached garage that can be also used for storage, a workshop or just plain garage! And, it

Christine Lewis Brattleboro Area Realty

A classic, stately Vermont Colonial wonderfully set on well over an acre of level land in Westminster, the oldest existing village in Vermont. This storied home was first the parsonage for the First Congregational Church, established in 1767. As was the custom of the time, the property was developed in phases. One of the first buildings was the large barn now situated behind the house, where

Bill Hickok Berkley & Veller Greenwood Country

PRICED TO SELL! Fabulous Southern Vermont Estate nestled between Mount Snow and Stratton Ski Areas! You'll have Wardsboro Brook in you back yard & Grout Pond down the street as well as the hiking trails VAST, Appalachian Trail (AT) and Long Trails. Plenty of Back Country outdoor Experiences available all year round! They say location is everything this property has everything and more. The

Kimberly Dubois Matson KW Realty

Make this beautifully constructed duplex your home in the woods. Sited on 59 acres of wooded land, you can make use of the trails on foot or bike. enjoy the peace while being just a short drive from Bellows Falls. The home was built from lumber harvested from the property and lovingly built by the present owners. The majority of the land, 53 +- acres, is held in current use with a wood lot plan

John Tolosky Barrett and Valley Associates Inc.

Welcome to 1082 West River Road — a peaceful, well-located gem just minutes from downtown Brattleboro. This charming home offers the perfect blend of convenience, outdoor space, and natural beauty. Set on a spacious lot with a large, open yard, there's room to garden, gather, or simply relax and enjoy the Vermont seasons. The private river access makes it easy to enjoy kayaking, swimming, or

Kate Barry EXP Realty

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.

Gale Alger Alger Real Estate Agency

This house sits on a lot that is surrounded by common land so it feels very secluded and private. Newer septic, roof, and main level flooring, and the prior owner did a lot of custom wood paneling with built-ins, and creative decorating which add to its charm. The main level has a mudroom entry with laundry and storage space, full bath, kitchen with open shelving above and cabinets below, newer

Sigrid Pickering Chimney Hill Realty

Just right for new beginnings! This raised ranch affords the new home buyer a cozy place to start with a big, level yard with lots of flowering shrubs to look pretty when you drive up, and a perfect spot for ball in the back! The dead end street is a bit safer for bikes and strolls than others and creates a nice comfortable neighborhood for smiling greetings. With an eat in kitchen with

Christine Lewis Brattleboro Area Realty

Cute home at the end of the cul-de-sac. Large front deck with a slider that leads into a newly refinished kitchen, dining area and living room. A half bath with laundry complete the first floor. Two bedrooms upstairs with a full bath. First floor has a door that leads out back to another large deck. The third bedroom and family room in the walkout basement. Open house Saturday 6/21/25 from

Darlene Conca Keller Williams Realty Metro-Keene

This home truly has it all and is conveniently located on one Brattleboro's most charming streets. Close to shopping, restaurants, and downtown yet tucked away from it all. The large fenced lot has good exposure for gardening. Inside the home you will find 3 bedrooms and a fabulous renovated attic, complete with custom cabinetry and shelving. Enjoy indoor/outdoor entertaining with french-door

John Hatton Berkley & Veller Greenwood Country

This rare multi-family home presents a unique investment opportunity, featuring four well-designed units. Nestled in the charming town of Jacksonville you're just 23 minutes from the exhilarating slopes of Mount Snow ski resort. The property offers two one-bedroom units on the first floor, alongside a spacious two-bedroom unit and a generous three-bedroom unit on the second floor. Enjoy the large

Monique White Deerfield Valley Real Estate

Attractive and well maintained 3 unit Multi-family with great in-town location. Many original features remain including wood floors, 2 marble mantles, moldings, curved walls, beautiful arches and built-ins. Unit 1 on the first floor features living room open via graceful arches to dining room, large eat-in kitchen, 2 large bedrooms,, hardwood floors, marble fireplaces. Unit 2 is on the 2nd floor

Steve Schoppmeyer BHG Masiello Brattleboro

Charming historic home with modern updates and exceptional outdoor Living! This sweet, well-built home exudes character and curb appeal. Thoughtfully updates over the years, it features a striking standing seam metal roof, updated 200-amp electric panel, fabulous 2 story deck with low-maintenance Trex decking and a slab for a hot tub, complete with the hookup. Inside, enjoy the convenience of

Kerry Mulverhill Brattleboro Area Realty

Originally built for the 1980 Lake Placid Winter Olympics, this iconic A-frame was later relocated to a serene 2+ acre setting in Marlboro Vermont. Tucked away on a quiet paved road, this 3-bedroom, 2-bath home blends rustic charm with thoughtful updates, including spacious additions and featuring a large mudroom—perfect for storing winter gear after a day on the slopes. The open-concept main

Chad Lackey Deerfield Valley Real Estate

Charming and well-built Cape-style home featuring 4 bedrooms and 2 full baths. The updated kitchen boasts tiled floors, generous counter space, and modern finishes—perfect for the home chef. Just off the kitchen, the dining room includes a sliding door that opens to the backyard and patio, ideal for indoor-outdoor entertaining.Beautiful hardwood floors run throughout the home—no carpet here. The

Monica Sumner BHG Masiello Brattleboro

This charmingly restored 1820's brick, former one-room schoolhouse has been meticulously expanded to include two bedrooms, a kitchen and full bathroom, and sits on a tranquil 5-acre lot with a mostly open, old pasture. The property retains its historical charm with exposed hand-hewn beams in the former schoolhouse that now serves as the living/dining area. Ideal for a cozy primary residence,

Dan Normandeau Berkley & Veller Greenwood Country

Charming 3-Bedroom Condo Just Minutes from Mount Snow!Welcome to your perfect Vermont getaway! This beautifully maintained 3-bedroom, 2.5-bath condo is ideally located in Southern Vermont, just minutes from the renowned Mount Snow Ski Resort and the Mount Snow Golf Course. Whether you're an outdoor enthusiast or seeking a peaceful retreat, this property offers the best of all seasons.Step inside

Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

Escape to your own private sanctuary on 8.1 acres of pristine land with stunning mountain views. This exceptional property is free from HOA restrictions, offering unlimited potential for your dream home or retreat. Featuring a cleared building site, new driveway, and a State of VT Wastewater Permit for a 4-bedroom dwelling, everything is in place for your vision. Accessible off a public road with

Chad Lackey Deerfield Valley Real Estate

Turnkey Townhouse in Sought-After Bears Crossing at Mount Snow, Vermont! Don’t miss this rare opportunity to own a beautifully updated end unit in one of the best-maintained buildings in Bears Crossing! Perfectly situated just steps from the clubhouse, heated pool, tennis and pickleball courts, and the dedicated Moover shuttle bus to Mount Snow—this location offers both convenience and

Steve Goldfarb Deerfield Valley Real Estate

The cutest house on the block! Only 1 house from the famous deli for eats, right near the entrance to I 91, both north and south for travel or work and 2 minutes away from Memorial Park with all it offers....skating, ball games, pools, sliding, skiing. Plus it has a great back yard, 2 levels of decks and a front porch to add to the package. This 1860's Mansard is so sweet, filled with character

Christine Lewis Brattleboro Area Realty

A rare opportunity for a Spruce Haven townhome accessible to the Dover village, Valley Trail, Mount Snow Ski Resort and Golf Course, the Hermitage private ski club, and MOOver shuttle service just down the street. This spacious and fully renovated end unit townhome has 3 bedrooms with en suite baths, a main floor guest half bath, a large open concept living space with hearth and efficient gas

Adam Palmiter Berkley & Veller Greenwood/Dover

This charming 3-bedroom, 2-bath home is tucked away in a peaceful wooded setting, offering the perfect retreat with a cozy, well-maintained ambiance. The spacious living room features a gas fireplace and a Rinnai heater, ensuring comfort throughout the seasons. Adjacent to the living area, the open kitchen and dining space make for a perfect gathering spot. A versatile den with a nearby 3/4 bath

Richard Caplan Deerfield Valley Real Estate

4-unit income property in an ideal location situated next to an operating farm with huge corn and other crop fields surrounding the parcel and very few neighbors. The 1.2 acres are all open and offer plenty of garden spots and outdoor recreation/activities for its tenants. Beautiful views out over the farm fields and an overall relaxed country living feel to this spot. Close to the CT River.

Chris Long BHG Masiello Brattleboro

Nestled between the renowned Mount Snow and Stratton Mountain, this completely remodeled late 19th-century Colonial offers the perfect blend of historic charm and modern comfort. Meticulously renovated, the home has been torn down to the studs and reimagined with no detail overlooked. With all new windows, insulation, electrical, and plumbing, every inch of this home has been looked after with

Mike Masters Four Seasons Sotheby's Int'l Realty

Discover your Vermont mountain escape just 5 minutes from Mount Snow, where charm meets convenience and rental potential. This expanded chalet offers seasonal rental income, making it a smart investment for those looking to maximize returns. Step inside to find a cozy mudroom with natural stone walls, perfect for storing ski gear. The main level features an open floor plan with exposed beams, a

Richard Caplan Deerfield Valley Real Estate

Renovated townhome in the Dover Green community located just a short drive or shuttle ride south of Mount Snow. This spacious unit overlooks a pond and nice sunny exposure thanks to recent clearing, and has easy access to parking and the side yard. Inside is an open concept floor plan with vaulted great room, wood burning fireplace and brick hearth, a large eat in kitchen with new cabinets,

Adam Palmiter Berkley & Veller Greenwood/Dover

Owners will consider offers. Lovely updated efficient chalet on 10 acres just up from the main entrance to Mount Snow. This cute home has great functional space without being overly large to maintain. The current owners have recently updated the heating system, roof, kitchen, bath, etc, to afford turn key enjoyment. Enter to a large great room with updated kitchen and breakfast bar, living room

Adam Palmiter Berkley & Veller Greenwood/Dover

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

Step into the charm of yesteryear with this spacious 1835s home that has a story to tell—yours is next! Enter through the oversized mudroom, which once served as the town post office, from the attached three-bay garage with automatic doors. This home features generous rooms throughout, starting with a large kitchen and dining area, a living room, two main-level bedrooms, and a full bath. Enjoy

Erica Reynolds Southern Vermont Realty Group

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

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

This land has many features. Beautiful large trees (Pines, Birches, Maples, Beech and more!), stone walls, beaver pond, several streams, views with clearing, wild Azalea's, Very private. The land has been perked for a 5 bedroom home in the appropriate area for views. There may be other areas that will perk. Views to the east. Large stream to the west. Some timber may be saleable. Without any

Regina Perrotto Skihome Realty

Sweet neighborhood. This would be a great location for an owner to live in one unit and rent the other 3. Lots of character! Great investment possibility. Close to Hospital, nursing homes, shopping, interstate for travel. Plenty of off street parking

Christine Lewis Brattleboro Area Realty

Just around the corner! From the middle and high school, Oak grove elementary! Pop around the corner for all the high school games, exercise at the track. Interstate is minutes away for easy access to work or play! One apartment is over 1,000 square feet so tons of room for owner occupancy! 2 nice front porches. Worth looking at for either your own home or as an investment. Masks please.

Christine Lewis Brattleboro Area Realty

Invest in your own home town! Full tenant roster with the easy access to laundry across the street, grocery stores, train and The Moover. Right in the heart of things with little yard to maintain! Consider as an investment in your portfolio or decide to live in one unit and have the others pay your mortgage! Good way to start, retire or increase your portfolio! Owner is a licensed appraiser.

Christine Lewis Brattleboro Area Realty