Windham County VT Homes under $500,000

This loving home has seen many years of enjoyment from its current owners. Four bedrooms, two and a half baths, large open kitchen dining area with a beautiful granite island to gather around. Separate living room space with beautiful stone fireplace and half bath all on the main floor. The four bedrooms with a lovely large primary suite with private bath, cathedral ceilings will be the perfect

Julie Lowe Lowe's Real Estate, LLC

COMMERCIAL OR RESIDENTIAL: The Bellows Falls Times Building, constructed in 1932 for the Vermont Newspaper Corporation, stands proudly at the corner of Bridge and Island Streets in downtown Bellows Falls, Vermont. This three-part complex—comprising the main brick newspaper plant, an adjoining warehouse, and a former garage—occupies a compact 0.13-acre lot along the canal fringe Equipped with

Rob Weltz Barrett & Valley Assoc. Inc

Tucked away on a peaceful 4.3-acre lot surrounded by mature trees, this “wow—worthy” 960 sq ft modern “glass house” (with additional 600+ sq ft of lower level living) on Bonnyvale Road, offers a stylish and serene retreat. Exquisitely designed, it blends indoor ease and simplicity with an outstanding natural setting. The stand-out home features an open-concept layout filled with natural light

Kate Barry EXP Realty

Beautifully updated and rustic chalet just south of Mount Snow and near the Mount Snow golf course and Valley Trail. This home sits on a wooded private lot but with amazing convenience just up from a MOOver shuttle drop off location, on a paved road, with easy access to nearby trails. Just about everything has been updated to make this a turn key property, and ready for immediate enjoyment.

Adam Palmiter Berkley & Veller Greenwood/Dover

Diamond in the rough! Don't miss this opportunity to own a property in Jamaica, Vermont that has so much to offer! This property has been absolutely stunning in the past! Perched on a hill overlooking a private pond, fields that used to be pastures where your animals can roam and you can take in the local ridgeline view of the beautiful Green Mountains of Vermont! This is a true log home with

Julie Lowe Lowe's Real Estate, LLC

Ahhhhh Dummerston! An enchanting 3 bedroom/3 bath classic historic Cape on 3.5 glorious and lush Vermont acres in the heart of Dummerston Center's rolling hills. Impressive attributes include the original wide pine wood floors and exposed beams, appealing custom cabinetry with butcher block countertops in the kitchen, a handsome period hearth and fireplace in the large living room, three cozy

Stephanie Peduzzi-Baker Brattleboro Area Realty

Oh wow, get ready to fall head over heels for your dream home! This beauty is nestled in the perfect spot, making every day feel like a breeze! You’ll be just a hop, skip, and a jump away from Dover Elementary School—how cool is that? Plus, if you're itching for a little adventure, Mount Snow Resort is only a quick 10-minute drive, and the charming vibes of Brattleboro are just a half-hour away!

John Redd Skihome Realty

Set on 10.4 acres in Guilford, this versatile property offers open pasture, multiple outbuildings, and direct views across Weatherhead Hollow Pond. Located on a town-maintained road, the property includes a 3-bedroom home with a new roof and many updated windows, a new septic tank in 2014, a large living area with floor to ceiling windows that look out to the pond, an attached 2-bay garage, two

Erica Reynolds Southern Vermont Realty Group

This is a unique, one of a kind, versatile, "blank canvas" opportunity. This is a 3 unit multi-family, fully rented/money making full time property now.. but, use your imagination, create your vision of what this premier location could be. Zoned BOTH commercial AND residential.. this property could be a fabulous restaurant with rivers edge al fresco dining or...a potential location for a new

Wilkie Bushby TPW Real Estate

Modern, contemporary 2-story home w/ unobstructed southern exposure in school-choice town of Vernon, Vermont. Built in 2010, this 3BR, 3BA home sits on a 1-acre, level lot, close to town rec. dept., as well as VAST snowmobile trail. Enter via the oversized 2-car garage (32 ft x 28 ft) or greet your guests at the formal front entry off the full-length farmer’s porch. Garage entry hall offers 2

Dan Normandeau Berkley & Veller Greenwood Country

Discover a hidden gem nestled deep in the woods—a rustic retreat that’s entirely off-grid and 100% solar powered. Perfect for nature lovers, creative spirits, or anyone seeking serenity and self-sufficiency.This one-of-a-kind property features a charming main house with a two-bedroom loft attached, currently used for short-term rentals. The main cabin exudes classic Adirondack charm with

Kate Barry EXP Realty

This lovely, updated 1790 Cape blends timeless New England charm with modern functionality and post-and-beam construction. Ideally located just outside the quaint village of Jamaica, the home offers easy access to four major ski resorts—Stratton, Bromley, Magic Mountain, and Mount Snow. Step into the welcoming kitchen, where a cozy fireplace creates a perfect winter haven. A soaring cathedral

Thomas Dahlin Berkley & Veller Greenwood Country

Unique opportunity to invest in your own home and have revenue from 2 apartments. Located close to all that Brattleboro has to offer for unique shopping, art, theater and lots of dining venues. The 1st floor apartment has over 1500 square feet of living space with 2+ bedrooms and two bathrooms, its own covered porch and expansive deck. Additionally, there is a spacious eat in kitchen, large

Susan Bellville Bellville Realty

Excellent opportunity to be close to everything Vermont has to offer and still feel secluded. This off grid efficient home is so easy to live in, get to and enjoy. IF you'd like to be on grid you're only about 7 power poles away. This offering is for currently combined 2 buildable lots which were subdivided many years ago. There is wonderful access to the woods for all activities. You can

Steve Goldfarb Deerfield Valley Real Estate

Stunning 2 acre building parcel at the prestigious Peaks at Mt Snow directly across from the ski resort. This lot affords tremendous privacy and exposure, but with amazing access and amenities including direct on call shuttle service from your door to the mountain, indoor pool, gym, clubhouse, and game courts. Paved road access, sewer, and water, means total peace of mind. Build your dream home

Adam Palmiter Berkley & Veller Greenwood/Dover

Property is being sold "as is where is" and does need some TLC. The house is set back off the road quite a bit for total privacy and there is a pond on the property. There is a one car garage, a full daylight basement, and a sun room.

Ginny Read Read Realty LTD

When you picture a rustic and woodsy Vermont retreat, but with modern comforts, this is that home. Spacious chalet style home located conveniently on the MOOver shuttle route 3 miles from the Mount Snow Ski Resort. This 4 bedroom, 2.5 bath home has exposed natural woodwork throughout, a great open concept floor plan with large living room and updated gas fireplace on brick hearth, direct views of

Adam Palmiter Berkley & Veller Greenwood/Dover

This beautiful Victorian home is just a short stroll from vibrant Brattleboro and has access to a huge town trail network. Nicely landscaped and has a partially fenced yard for pets or children. The house has lovely Victorian detailing and includes 3 covered porches. The formal entry has hardwood flooring, period staircase, stained glass window and a 3/4 bath. The adjacent front parlor includes

Robert Doyle Berkley & Veller Greenwood Country

Nestled just 5 miles from Stratton's base lodge on the historic grounds of the former White Mop Wringer Co., this remarkable home blends rich history with modern craftsmanship. Built in 2001, the house sits where, in the 1800s, Cassius A. White invented the mop wringer, making Jamaica, Vermont the birthplace of the first mop wringer factory. While the water wheel that powered the factory is no

Carrie Mathews Winhall Real Estate

This beautiful 2-bedroom, 2-bath end-unit condo in Seasons on Mount Snow offers the perfect combination of convenience, comfort, and mountain living. The open-concept floor plan with living, dining, and kitchen areas is perfect for family gatherings and entertaining. This mountain retreat, featuring a cozy floor-to-ceiling fieldstone fireplace, a slopeside location, and an abundance of natural

Jessica Bentz Four Seasons Sotheby's Int'l Realty

Charming Property with Endless Possibilities in Southern VermontNestled on 5 acres in the heart of Southern Vermont, this unique property offers the perfect blend of history, versatility, and potential. Currently operating as a successful Quilt Shop, this property presents an exceptional opportunity for a variety of uses – whether you’re looking to return it to a spacious home with 4-bedrooms, or

Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

Snowmobilers paradise! Enjoy direct access to the VAST trail just down the street or from the backyard. Take in stunning winter views of Mount Snow & Haystack Mountains and summer panoramas of Haystack ski area and the surrounding mountain range. This custom-finished, ranch-style modular home features 3 bedrooms, 2 baths with numerous upgrades including new appliances, generator, more

Jennifer Hovey-Densmore Deerfield Valley Real Estate

You choose! Such a versatile property...invest in 2 rentals...live in either unit and rent the other...maybe develop the barn into another unit, home business, workshop..(check with Zoning). Just short of an acre (.86) the land is the big, big seller....the huge, mostly level back yard is already lush with flourishing fruit trees and blueberry bushes. There is a garage/gardening shed for your

Christine Lewis Brattleboro Area Realty

This 3-bedroom 2-bath Chalet is quietly nestled on 2.6 acres in the heart of Vermont’s ski country. The upper level has a wonderful, spacious kitchen, with an open floor plan combining the dining area and living room, with wood-burning fireplace, has access to the the wrap around deck. One bedroom with a walk-in closet is also on the upper level. The lower level boasts 2-bedrooms, a full bath,

Mike England Michael England Real Estate

Perfect investment. Choose which flat you want to live in and have a bit of income, OR...consider this a long term investment! Such a special location and huge yard. Consider developing more apartments in the back of the house, and rent out the 40 x 40 steel frame building...OR develop into your dream workshop and let the rentals help pay for your fun. Rentals are below market for the

Christine Lewis Brattleboro Area Realty

You choose! This amazing property can be used as one of the grand ladies of the neighborhood...just open a door or two and repurpose the kitchen...what a nice laundry room it would make...or use as is with 2 flats, live in 1 and have a bit of income from the other...What else, you might ask! There is a rear section of the house ready to be reclaimed, and a barn attached that could also be built

Christine Lewis Brattleboro Area Realty

Welcome to this beautifully maintained, bright & spacious three bedroom, three bath Suntec townhome, offering the perfect blend of space, comfort, and convenience just minutes from Mount Snow’s main base lodge, Carinthia Lodge, and the Hermitage Club. This home features three large bedrooms with high ceilings, a versatile loft, and open-concept layout, providing plenty of room for family and

Prema Fitzpatrick Skihome Realty

This quintessential Vermont home in a quiet neighborhood on 2 gorgeous sun-filled acres has been loved and enjoyed by the same family for over 35 years. Inside you will find a spacious layout with many improvements including new carpet, paint, and windows (perfect for letting in lots of natural sunlight). Additionally, the multi-zone boiler is only about 9 years old, ensuring peace of mind for

Kerry Mulverhill Brattleboro Area Realty

This 2 bedroom, plus bunkroom, end unit condo is located across the road from the Mt. Snow ski area. There is a shuttle to the mountain that will allow you to be free from driving and parking fees. Relax in your private hot tub after a day on the slopes or sit on this spacious deck an enjoy the view. A cozy wood-burning fireplace sets the mood for your apre' ski afternoon. On a rainy or

Regina Perrotto Skihome Realty

This charming 3-bedroom, 2-bath dutch colonial home sits atop a knoll, overlooking a picturesque half-acre pond in the front yard. Nestled on 2.06 acres in a tranquil neighborhood, the property offers an excellent floor plan for family living. The home features spacious bedrooms, a cozy brick fireplace in the living room with a cathedral ceiling, and a dining area with pine floors and pond views.

Jennifer Hovey-Densmore Deerfield Valley Real Estate

Cozy convenience on Haystack Mountain adjacent to The Hermitage Club and just a short drive to Mount Snow and downtown Wilmington. This 2 bedroom/2 bathroom unit has an open living space perfect for entertaining and highlighted by the fieldstone fireplace ambiance to warm you apres ski/hike or snowshoe. The unit is being offered furnished and ready to enjoy this season and year round with access

Cordelia Garofalo Deerfield Valley Real Estate

This 2 bedroom, 2 bath, end unit is a great home base for trailside living at Seasons on Mount Snow. Midway up in the development, this unit offers the convenience of ski-on/ski-off, as well as being close enough to walk to one of the best onsite amenities center in the valley. The amenities center features a recently renovated and expanded clubhouse with an indoor pool, locker rooms, saunas,

John Redd Skihome Realty

Whether you are unwinding from a long day at the slopes of Mount Snow or you just enjoyed 18 holes at the Country Club, relax and get away with this beautiful home located in Partridge Run. This home boasts 3 bedrooms, 3 full bathrooms plus a Loft! You are welcomed upon entry by a very spacious mudroom with ample room to store your equipment for all seasons. The living, kitchen and dining areas

Tobin Twelves Skihome Realty

This fully refurbished multi-family building offers two distinct units - a spacious 3 bedroom plus loft 3 bath unit on the left (Unit 2) and a 2 bedroom plus loft 2 1/2 bath unit on the right (Unit 1). Both feature elegant hardwood floors throughout, except for the carpeted lofts. The kitchens in each unit are custom-designed with granite countertops and stainless steel Samsung appliances, fully

Jennifer Hovey-Densmore Deerfield Valley Real Estate

Beautiful updated condo overlooking the 1st green at the Haystack Golf Club, as well as the mountains and sunsets beyond. This lovely private unit sits right on one of the best courses in New England, and is a short drive from the village of Wilmington, nearby lakes, and Mount Snow and Hermitage Club ski resorts. The interior features a large open living space with vaulted ceilings, updated vinyl

Adam Palmiter Berkley & Veller Greenwood/Dover

Mountain Retreat located at 44 Villager Loop, Dover Hills, Dover, VT Very little use and never rented. Upgrades include a freshly painted exterior with a new roof and 3 mini-splits. Large mudroom entry, living room with fireplace, kitchen, dining area, 3 bedrooms, 3 baths, family room and a large deck for entertaining and relaxing. Close to the town center, restaurants, Town Park and Valley

Janet Boyd Boyd Real Estate

Discover the ultimate winter retreat with this beautifully updated two-bedroom condo, perfectly situated just a short walk from the lifts and the brand-new base lodge at the Sundance face of Mount Snow. Step inside and be greeted by the warm ambiance of bamboo floors, complemented by sleek granite countertops and a stylish mosaic tile backsplash in the kitchen.The condo is part of the Seasons

Mike Masters Four Seasons Sotheby's Int'l Realty

A rare gem hitting the market after 22 years. Its design spans two levels, 2-ensuite bedrooms & 2.5 baths, providing ample space for comfort & convenience. Sold furnished, it's primed for immediate enjoyment. Nestled within the Greenspring community, this unit offers easy access to the rec center, pool, & tennis courts, just a short stroll away. The private back deck affords stunning mountain

Donald Koelsch Deerfield Valley Real Estate