Windham County Homes under $200,000

Welcome to Windham County, Vermont, a picturesque gem nestled in the heart of New England. Known for its stunning landscapes, vibrant communities, and rich history, Windham County offers a unique blend of rural charm and modern conveniences. From the rolling hills and lush forests to the serene rivers and quaint towns, this area is perfect for those seeking a peaceful lifestyle surrounded by nature.

One of the most attractive features of Windham County is its affordability, particularly for homebuyers looking for homes under $200,000. Whether you’re a first-time buyer, a retiree, or looking for a vacation getaway, this region has a variety of options that won’t break the bank. You can find charming single-family homes, cozy cottages, and even some delightful fixer-uppers, all waiting for your personal touch.

The county is not just about affordability; it's also about community. With friendly neighbors and a welcoming atmosphere, you’ll feel right at home. Enjoy local farmers' markets, seasonal festivals, and outdoor activities like hiking, skiing, and fishing that make Windham County a fantastic place to live and play.

Additionally, the area boasts excellent schools, local shops, and a rich cultural scene, including art galleries and theaters that showcase local talent. Whether you’re looking to raise a family, retire, or simply enjoy a slower pace of life, Windham County has something for everyone. Come explore the possibilities of owning a home in this enchanting corner of Vermont!

Newest Windham County Homes under $200,000

$150,000

2 Beds ⋅ 1 Baths ⋅ 5113182 MLS

This West Wardsboro chalet is looking for someone to bring it back to life! Full of potential and ready for renovation, this property offers the perfect opportunity to create your own Vermont mountain getaway. The town lists the property as a three-bedroom, though it currently features one bedroom plus a loft, offering flexibility for future improvements. Set on a nice lot in a convenient location, you’re just 10 minutes from Mount Snow and under 20 minutes from Stratton Mountain, with easy access to skiing, snowboarding, hiking, biking, and year-round outdoor adventure. Enjoy the best of southern Vermont with shopping and dining nearby, while still having a peaceful setting to call home. Bring your vision, your tools, and a little love this chalet could become the mountain retreat you’ve been looking for!

81 Scandia Village Rd, Wardsboro

$20,000

1 Beds ⋅ 2 Baths ⋅ 5113056 MLS

This one-of-a-kind unit features one level and includes one bedroom, two full bathrooms, and an open-concept kitchen, living, and dining area. The living room area features a queen Murphy bed and a queen pull-out sleeper sofa, comfortably sleeping six people. The spacious bedroom includes a king-size bed and a balcony with beautiful ridgeline views. Grand Summit ownership benefits include using your 13 weeks, renting when you're not using it, or trading through timeshare networks such as RCI and Interval International. The Grand Summit Resort Hotel ownership includes valet parking, an owner's private lounge, an owner's private library, an outdoor, year-round, heated pool, a steam room, hot tubs, a full-service spa, and private owners' lockers, all located trailside at Mount Snow. This is a great way to enjoy the mountain resort lifestyle at an affordable price!

230 Qtr 4 89 Grand Summit Way, Dover

$189,500

2 Beds ⋅ 2 Baths ⋅ 5112756 MLS

This cozy condo faces a hillside, landscaped with beautiful mature hydrangeas. Besides beauty, the hillside offers privacy and quiet. And no headlights will shine in your windows. The seller has totally renewed the unit with a new hot water heater, newer boiler, new gas range, new microwave, new closet doors and new flooring, and it was newly painted throughout. Then it was professionally cleaned. It is ready for you to move in. Association amenities include a swimming pool, tennis/pickleball courts, basketball, hiking trails, little libraries and common area gardens. The Association takes care of all outside maintenance. Downtown Brattleboro is within walking distance. Easy living awaits you at 29 Morningside Commons.

29 Morningside Commons, Brattleboro

$30,000

1 Beds ⋅ 2 Baths ⋅ 5112331 MLS

Trailside! Use it, Rent it, Trade it! Imagine having 13 weeks of vacation each year with this deeded quarter-share property, offering you one week every 28 days on a rotating schedule. Interval 3 owns Christmas and New Year's weeks this year, back-to-back, and Dec 18-28, 2026 is held out for owner use. This unique unit boasts stunning valley views and features a 1-bedroom, 2-full-bath setup, accommodating up to 6 guests. The open-concept kitchen and dining area complement a living room that includes a deck, a Murphy bed, and a queen sleeper sofa. The loft-style ensuite bedroom comes with a king-sized bed and a walk-in closet. As an owner, you'll enjoy the prime ski-in/ski-out location at Mount Snow, with year-round access to Grand Summit Hotel amenities. These include valet parking, an owners' private lounge, a library, a deck, a full-service gym with a sauna and steam room, outdoor hot tubs, and a heated outdoor pool. You'll also have exclusive access to owners-only locker rooms for ski or golf equipment storage. A popular perk for owners is the “Space A” option, which allows you to stay at the hotel outside your ownership time at a discounted rate—just cover the housekeeping fees. This property is affiliated with RCI and Interval International.

328 Qtr 3 89 Grand Summit Way, Dover

249/251 Qtr. 3 89 Grand Summit Way Unit 249/251 Qtr 3, Dover

$25,000

1 Beds ⋅ 2 Baths ⋅ 5111966 MLS

Trailside, best ski in/out mountain location. A really comfortable unit sleep 8. Unit 251 includes a kitchenette, comfortable living room setting, a sleep sofa a Murphy bed and full bath. Unit 249 boasts 2 queen size beds a full bathroom, and a deck with views of the mountain to enjoy skiers on the slope and fireworks. Just imagine entertaining family and friends! Benefits of ownership include year round usage of all amenities, outdoor heated pool, sauna, owners private lounge, valet parking, full service spa, gym, ski locker. Discounts on food and retail. And a favorite perk, Space Available that gives you the opportunity to stay in the hotel when it's not your ownership time for the discounted rate of housekeeping. You can use it, rent it or trade with RCI and enjoy resorts world wide. This unit is a lockout. You can rent it several ways, as a full 1 bedroom 2 bath, as a studio sleep two or an hotel suite sleep 4. Enjoy your ownership this year that includes Christmas and New Year weeks.

249/251 Qtr. 3 89 Grand Summit Way Unit 249/251 Qtr 3, Dover

263 Qtr.3 Grand Summit Way Unit 263 qtr 3, Dover

$70,000

2 Beds ⋅ 2 Baths ⋅ 5111533 MLS

Discover the perfect blend of comfort and luxury in this 2-bedroom, 2-bath deluxe unit at the Grand Summit Resort. The entry level is a haven of natural light, featuring a cozy gas fireplace, comfortable furnishings, and a sleep sofa. The dining area, with a table that seats eight, is ideal for hosting memorable gatherings. The kitchen boasts granite countertops, full-size appliances, and a convenient breakfast bar for casual meals. This level also includes a bedroom with two sets of bunk beds, a washer and dryer, and a deck that provides stunning views of the trails. Descend to the lower level to find the primary bedroom, a true retreat with a second fireplace, a king-size bed, and luxurious amenities such as a sauna and jacuzzi tub. This level also features another private deck, offering a peaceful escape. Ownership of this unit offers incredible flexibility, use it as your personal getaway, rent it out, or trade it with RCI or Interval International for vacations in other stunning locations. Resort amenities elevate your experience with a heated pool, saunas, an owner's lounge, indoor locker, and convenient valet parking. This year, ownership includes coveted Christmas and New Year stays, along with exclusive discounts on food and retail. The owner's perk, "Space A," provides the option to stay in the hotel at a discounted rate during non-ownership times. Embrace this incredible opportunity to enjoy the best ski-in, ski-out location on Mount Snow.

263 Qtr.3 Grand Summit Way Unit 263 qtr 3, Dover

$200,000

4 Beds ⋅ 2 Baths ⋅ 5111334 MLS

Room to spare! This nearly 1700 square foot home is tucked into a sweet neighborhood on the outskirts of Westminster and Bellows Falls. Flat fenced sunny ptivate back yard for gardening or fun, 1 car garage and paved drive all add to the excitement of this home. The original double 1975 wide has a 2 story bedroom addition. The floor plan is very open and versatile, with a great flow and accessibility. Enjoy the sun or rain on the enclosed back porch doubling as a cozy safe place for pets to watch the birds or laze in the sun. Easy to show. Manufactured homes are a specialized financing, please chat with your bank for the appropriate pre approval.

47 Adams St, Westminster

$22,000

2 Beds ⋅ 2 Baths ⋅ 5111269 MLS

Use it, Rent it, Trade it! Do 13 weeks of vacation a year sound nice? This sleep 6 unit consists of two adjoining units: a studio unit (226) with a Queen Murphy bed, kitchenette, and full bathroom. Hotel unit 228: two queen beds and a full bathroom. Units are located on the valley side of the hotel. Lockout units let you use the unit as a whole or stay on one side and rent the other. Grand Summit ownership includes the best ski in/out mountain location available. Use the Grand Summit amenities year-round, including valet parking, the owners' private lounge, the private owners' library, a full-service spa with sauna, hot tubs, and an outdoor heated pool, and private owners-only ski/golf locker rooms for year-round storage. A favorite owner's perk is "Space A," which lets you stay in the hotel even when it's not your ownership time, at a discounted rate... and you still pay housekeeping fees! Truly an affordable way to get that mountain resort lifestyle! RCI and Interval International Affiliated

226/28 Qtr.2, Dover

$189,000

2 Beds ⋅ 2 Baths ⋅ 5111264 MLS

Here's a great opportunity in a convenient location being minutes to town while also being a short drive to the school and local produce stands and orchards. This two bedroom home includes additional spaces that could be used differently but are currently being used as home offices. Open concept living in the main area between the kitchen/dining/living room areas make for great gathering space. The detached 2 car garage provides additional storage space above in addition to getting your toys out of the weather. There are also mini splits to help with heating and air conditioning so there's great potential to add your finishing touches to this convenient property!

226 E West Rd, Dummerston

$129,000

2 Beds ⋅ 1 Baths ⋅ 5111023 MLS

Tiny-home ready for the next owner to make their own! The property offers a solid start to creating a comfortable, 2-bedroom tiny-home. The original log cabin sugarhouse features the kitchen, the dining area and ¾ bath while the unfinished addition houses the living room and the two-bedrooms. With the property’s basic infrastructure already in place - town water and sewer, 100 amp service and new roofing, the next owner can focus on completing the remaining exterior / interior work. Enjoy the outdoors from the deck or the yard. Tucked away at the end of a private road extension in a sought-after west Brattleboro residential neighborhood, the setting is tranquil but super convenient, only minutes to downtown Brattleboro and the highway. Sold As-Is. Cash or Rehab Financing Buyers Only.

50 Lawton Dr, Brattleboro

$179,000

1 Beds ⋅ 1 Baths ⋅ 5110478 MLS

Don't wait to come view this newly remodeled, low maintenance, affordable and desirable ground floor end unit. Inviting circular flow, the spacious living room has a brand new slider with a view of the rear yard and the Whetstone brook. Plus, you have a brand new kitchen and appliances. The large bedroom with double closet has direct access to the newly renovated bath. This condo is located in a prime location with quick, easy access to I91 and a stones throw to the Whetstone Brook, Farmers Market and Living Memorial Park. Association fees include heat, water/sewer, landscaping and more. Come visit this sweet home with an attractive price.

40 Brookside Dr Unit 2, Brattleboro

$165,000

3 Beds ⋅ 3 Baths ⋅ 5110251 MLS

An exceptionally rare and enchanting waterside setting along Broad Brook. Hugged by the gentle curve of the water with direct frontage and stream access, this property offers a front-row seat to cascading waterfalls and the soothing soundtrack of rushing rapids right outside your door. It is the kind of storybook Vermont setting that simply cannot be replicated.The existing multi-level residence (2,376 sq. ft.) is in need of a full, top-to-bottom renovation, presenting a true blank canvas for an inspired builder, artisan, or visionary ready to bring a custom retreat to life. The structural footprint is packed with eclectic architectural soul, featuring sculpted organic archways, exposed timber framing, rich wood floors, a dramatic lofted staircase, and extensive glass designed to look straight onto the water. A walk-out deck sits suspended over the natural stone-lined bank, offering an unrivaled vantage point over the falls. While the building requires complete rehabilitation, essential site utilities are already established: the on-site septic system is intact, a private well exists on the parcel, and electric service is connected.Whether you reimagine the interior as an architectural riverside showpiece, an artist retreat, or a peaceful brookside sanctuary, the setting and site infrastructure provide an irreplaceable foundation. Bring your tools, your vision, and your contractor to unlock the magic of this truly singular Guilford property.

1107 Broad Brook Rd, Guilford

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