Windham County Homes under $500,000

Welcome to Windham County, Vermont, a picturesque region that beautifully marries natural beauty with a vibrant community spirit. Nestled in the heart of the Green Mountain State, Windham County is renowned for its stunning landscapes, charming small towns, and an array of recreational opportunities. Whether you’re an outdoor enthusiast or someone who appreciates the arts and culture, this county has something for everyone.

Windham County boasts a variety of homes under $500,000, making it an ideal destination for first-time homebuyers, families, and those looking to invest in a serene getaway. From cozy cottages tucked away in the woods to charming single-family homes in quaint towns like Brattleboro and Bellows Falls, the housing market here is diverse and inviting. Many of these properties feature beautiful views, spacious yards, and easy access to hiking trails, lakes, and ski resorts, ensuring that you can enjoy the best of Vermont living right at your doorstep.

In addition to its affordable housing options, Windham County is rich in community spirit. Local farmers' markets, art galleries, and seasonal festivals bring residents together, fostering a strong sense of belonging. With excellent schools, a focus on sustainability, and an emphasis on outdoor activities, it’s no wonder that Windham County is becoming a sought-after location for those looking to call Vermont home.

Explore the charm of Windham County today, and discover your perfect home in this idyllic corner of Vermont!

Newest Windham County Homes under $500,000

$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

$379,000

3 Beds ⋅ 2 Baths ⋅ 5113048 MLS

Bright, open, and airy 3rd floor 3 bedroom, 2 bath Deer Creek condo in a convenient resort-area location across from Mount Snow. Set over two floors, the layout gives room to spread out while still keeping the main living space comfortable and connected. The great-room style living, dining and kitchen area with a cathedral ceiling boasts a wood-burning fireplace and access to a covered back porch overlooking open field and forest views. With three bedrooms, including two en suites, the condo can easily accommodate six people, making it well suited for owners and guests without everyone feeling piled into one space. A practical mudroom area includes full-size washer and dryer units, gives you a place to drop boots, coats, and gear when you come in from the mountain in addition to an exterior ski locker. The current sellers have thoughtfully refreshed the unit throughout, giving it a clean and updated feel without losing its comfortable and warm ski-home character. The location is also a big part of the appeal here! Deer Creek sits on Handle Road between the Carinthia and Sundance Base Lodges. It's close enough that some may consider the Sundance lifts to be walking distance, while others may prefer to jump on the MOOver shuttle with a stop just around the corner at Equipe Sport—for easy access to the main Clock Tower area and the rest of the Mount Snow base. Being positioned on the resort side of the main Route 100 corridor means avoiding much of the inbound and outbound resort traffic at the beginning and end of the ski day. Spend more of your weekend enjoying what you are here for and less time navigating to and from! Firewood, trash removal, plowing, and lawn care are all handled by the association, keeping ownership simple. Deer Creek also offers some of the lower association fees in the Mount Snow area. This is a well-laid-out condo with the space to gather, room to spread out, and a location that puts the best of the Mount Snow resort area close at hand.

14f Deer Crk, Dover

$359,000

3 Beds ⋅ 2 Baths ⋅ 5113029 MLS

Tucked into a peaceful private setting just outside Putney Village, this charming 4-acre property captures the spirit of rural Vermont living. Surrounded by woods, open space, and abundant wildlife, the property offers a wonderful sense of privacy while remaining close to the village’s lively arts, culture, and community. The 1,700-square-foot home is thoughtfully suited to first-floor living, with a comfortable primary bedroom featuring an en-suite bath. A spacious deck invites you to slow down and enjoy the changing seasons, whether listening to the sounds of nature, watching wildlife, or gathering with friends. A fabulous pond adds to the property’s natural beauty and provides a tranquil centerpiece for this special piece of land. The large two-car garage offers plenty of room for vehicles, tools, and Vermont projects, while the full barn provides generous storage above and additional space below - ideal for a workshop, studio, hobbies, or simply embracing the possibilities of country living. The partially finished basement adds even more flexible space. With its combination of privacy, acreage, pond, barn, and proximity to Putney Village, this is a quintessential Vermont setting - a place to put down roots, enjoy the land, and live at a slower, more connected pace. This property will need a bit of love and it will be well worth it! Open House Saturday Oct. 10. 11:00-1:00

56 Old Stage Rd, Putney

8h Trailside Village Way Unit I22, Dover

$454,000

2 Beds ⋅ 2 Baths ⋅ 5113004 MLS

Slopeside living at its best at Seasons on Mount Snow! This well-maintained 2-bedroom, 2-bath condominium has been lovingly enjoyed by its owners since 2003 and has never been rented. Ideally located for easy access to the slopes, this inviting residence offers the perfect blend of mountain convenience, comfort, and resort amenities. Step inside to a warm and welcoming open-concept living space highlighted by a stunning fieldstone, floor-to-ceiling wood-burning fireplace—the perfect gathering place after a day on the mountain. The dining area and kitchen with a breakfast bar create an ideal space for entertaining family and friends. Natural light fills the home, and a private deck just off the dining area provides a wonderful spot to relax and take in the fresh mountain air. The two-bedroom layout offers privacy and flexibility, including a spacious primary suite with an ensuite bath and walk-in closet, plus a second bedroom and hall bath. Both bathrooms have received a nice refresh, including new tile. An outdoor ski locker provides convenient storage for all your winter gear, while the easy-access location makes getting to and from the slopes a breeze. Owners at Seasons enjoy exceptional recreation at the Seasons Sports Center, featuring an indoor pool, a new indoor hot tub, fitness center, game room, two lounges—including an exclusive owner-only lounge—locker rooms, and saunas. Outdoors, enjoy a seasonal in-ground pool, hot tub, dining and grilling area, and fire pit. Whether you're skiing or snowboarding in the winter, enjoying the mountains in summer, or leaf-peeping in the fall, the amenities at Seasons create a true four-season resort experience. With its prime slopeside location, generous amenities, inviting mountain interior, and rare history of never being rented, this Seasons condominium is a special Mount Snow opportunity.

8h Trailside Village Way Unit I22, Dover

$375,000

3 Beds ⋅ 2 Baths ⋅ 5112926 MLS

Bright, sunny solid 2-story house, tons of light, with 3 bedrooms, 1 1/2 bathrooms, on 0.4 acres, in a picturesque Guilford location. Quiet, sunny yard, with fruit and shade trees. Your neighbors are the historical society, meeting house, library, an historic brick schoolhouse, and a playscape park around the corner. All new wiring and plumbing. Basement has a concrete slab, has been structurally-reinforced, drainage is in place. The kitchen was taken out, and is now ready for your choices (the room is down to the studs). List price is adjusted for no kitchen. Pellet boiler, baseboard hot water heat. Lots of storage space. Large attached barn offers interesting possibilities. This is a classic house with lots of curb appeal. Property is being sold As Is. A local lender has offered financing through a rehab loan. Come check it out! Open House, Saturday, October 10, 11am-1pm.

4054 Guilford Center Rd, Guilford

$395,000

3 Beds ⋅ 2 Baths ⋅ 5112923 MLS

Welcome to 8 Winhall Station Road in South Londonderry, a well-located three-bedroom, two-full-bath Vermont home offering convenient access to some of Southern Vermont’s best year-round recreation. Several major ski resorts are within easy driving distance, along with nearby hiking trails, campgrounds, swimming, biking, and countless opportunities to enjoy the Green Mountains. The home offers a comfortable, practical layout that works equally well as a primary residence, vacation retreat, or ski getaway. Its location combines the peaceful feel of Vermont country living with convenient access to local schools, shopping, dining, and everyday services. Whether you are drawn to the area for skiing, hiking, camping, or simply enjoying the beauty and relaxed pace of Southern Vermont, 8 Winhall Station Road provides an excellent home base for every season. With multiple resorts and outdoor destinations nearby, this property offers a wonderful opportunity to enjoy the Vermont lifestyle year-round.

8 Winhall Station Rd, Londonderry

$499,900

3 Beds ⋅ 3 Baths ⋅ 5112846 MLS

Enjoy Vermont living in every season! This spacious 3-bedroom, 3-bath home sits on an oversized lot close to the Hermitage Club and Mount Snow, offering plenty of room to gather, relax, and unwind. Outstanding community amenities include indoor and outdoor pools, a hot tub, tennis, pickleball, and basketball courts, plus a clubhouse with an arcade and lounge. With hiking, biking, boating, golf, and skiing at your fingertips, adventure is always within easy reach. Whether you’re seeking a mountain getaway or a year-round home, this property offers space, recreation, and a convenient location to enjoy it all. The seller is open to selling the neighboring lot to the purchaser of the home. The offer is at a very fair price, and the seller is open to negotiations.

14 Hightop Rd Unit B124, Wilmington

$359,000

3 Beds ⋅ 2 Baths ⋅ 5112782 MLS

This gem is tucked away in the quiet Section C part of the super popular Chimney Hill, HOA this modified ranch style home, featuring 3 bedrooms, half and full baths, a gas fired stove in the open concept living/dining area, and a pellet stove in the Bonus Room. Careful attention to detail, landscaped gardens, Firepit, fenced in area in the back, garage/Bonus Room addition, covered porch, custom woodwork inside and out. For those who like a more rustic 'Vermonty" vibe, this is it! Stop dreaming and start living the dream! Enjoy all the amenities offered by Chimney Hill ON THE 1,200 Acre Campus with an exclusive member only Clubhouse located 2,000' up on the Hill with indoor and outdoor heated pools for year-round swimming, arcade room, après ski lounge, fully-equipped kitchen for members use, fitness room, community style hot tub, community room, playgrounds, 3 areas with tennis courts, extensive trail system, lookout, fishing pond stocked with annual kids fishing derby, seasonal pickleball and ice skating, basketball court, birchwood recreation area, and so much more! See why Southern Vermont and the Deerfield Valley are so popular, offering World Class Skiing and Shredding at Vail's Mt. Snow, and the privately owned Hermitage Club at Haystack Mt., festivals, flea markets, antiques, uniques shopping and fine dining experiences, music, mountains, boating, golf, S VT Pickleball Club, mountain biking, and so much more!

60 E Brook Xing Unit C-201, Wilmington

$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

$259,000

1 Beds ⋅ 1 Baths ⋅ 5112712 MLS

An easy Mount Snow getaway in an incredibly convenient location. This charming one-bedroom condo in the Mountaineer development sits across the street from the Magic Carpet, with mountain views that include the summit and the top of the Bluebird Express. The efficient layout makes great use of the space and gives you everything you need for a low-maintenance Vermont escape, including a wood burning fireplace that adds classic ski condo warmth and a bathroom with a Jacuzzi tub for relaxing after a day on the mountain. The bedroom opens through a large sliding glass door to a private patio, where you can take in the mountain view and enjoy being right in the middle of the Mount Snow action. The unit entry is tucked around the side of the building and includes a dedicated ski locker, making it easy to come and go with gear. Whether you are heading across the street to ski, grabbing dinner nearby, or settling in by the fire, the location is hard to beat. Offered furnished and ready to go, this is an easy option for anyone looking for an efficient second home, ski base, rental or Mount Snow retreat with exceptional access to everything the resort area has to offer.

266 Handle Rd Unit I, Dover

$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

$299,000

1 Beds ⋅ 3 Baths ⋅ 5112295 MLS

Rare investment or owner-occupied duplex opportunity in Guilford, offered for the first time in over four decades! Nestled on a scenic parcel featuring its very own private swimming pond, this property delivers a classic Vermont setting with unbeatable potential. The grounds showcase quintessential New England charm, complete with stone walls, an established old garden bed with hydrangea, trailing grapevines, and productive blackberry and raspberry bushes. The owner has lovingly held this property for 43 years, providing a solid, deeply rooted foundation for its next chapter. All major systems are in good working order, highlighted by brand-new, high-efficiency heat pumps just installed to provide modern heating and reliable cooling. The structure and interior have been well-maintained over the years, though the aesthetics remain classic 1980s. The finishes are tired and ready for a cosmetic refresh, making this the ideal blank canvas to bring your design ideas, build immediate equity, and customize both units to your taste. Whether you choose to live in one unit while offsetting your mortgage with rental income from the other, or hold the entire property, the combination of strong systems, acreage with a private pond, and rental flexibility is hard to find at this price point. Property is being sold in "as-is" condition. Sale is subject to the seller finding suitable housing. Don't miss the open house this Saturday from 12:00 PM to 2:00 PM!

1311 Stage Rd, Guilford

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