Windham County Homes under $350,000

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Newest Windham County Homes under $350,000

$299,000

2 Beds ⋅ 1 Baths ⋅ 5114567 MLS

A rare opportunity to own true West River frontage in the heart of Dummerston, Vermont. Nestled along one of Southern Vermont’s most beloved waterways, this property delivers a rare combination of privacy, natural beauty, and convenience. This charming two bedroom, one bath retreat offers an inviting blend of rustic comfort, year round recreation, and unbeatable summer enjoyment right on the river’s edge. Private West River beach, your own secluded spot for swimming, sunning, paddling, and cooling off during Vermont’s warm summer months. Large deck off the eat in kitchen, perfect for morning coffee, evening dinners, and taking in the peaceful river views. This is a cozy, manageable layout ideal for weekend getaways or full time living. Additional outbuildings offering character, storage, and flexible use for gear, hobbies, or seasonal equipment. Offered fully furnished, move in ready and prepared for immediate enjoyment less a few personal items. A list to be provided prior to any written offers.

237 Camp Arden Rd, Dummerston

$275,000

1 Beds ⋅ 1 Baths ⋅ 5114514 MLS

A rare opportunity to own a camp on beautiful Sunset Lake! One of only seven cottages on the entire lake, this special getaway offers peace and serenity surrounded by nature. It is the perfect spot for fishing and enjoying life alongside the local loons. With 75 feet of waterfront, a screened porch overlooking the lake, and a loft sleeping area, this cottage is ready for lake days and unforgettable summer memories. The kitchen features a refrigerator, stove top, and dishwasher, while a separate outbuilding offers additional storage and a 3/4 bathroom. Grab your kayaks, head down to the water, and enjoy the simple pleasures of summers at the lake for years to come!

311 Lake Rd, Marlboro

$249,000

3 Beds ⋅ 2 Baths ⋅ 5114286 MLS

Step into a piece of Jamaica Village history. Once home to the F.E. Smith Dry Goods, Ready-Made Clothing, and Grocery Store, this distinctive red-and-white building blends Greek Revival presence with Vermont farmhouse character and now serves as a year-round residence filled with history and personality. The classic façade features full-width double-decker porches, white picket railing, and bold corner pilasters. Inside, this C. 1860 building’s commercial past lives on in a dramatic great room with original built-in storefront shelving and drawer banks once used to display dry goods. Now a unique library, studio and sitting area, the space features wide-plank wood floors, exposed beams, and natural light from the original storefront windows and door. A vintage interior sash window adds another unexpected architectural detail. The kitchen features sage cabinetry, granite tile counters, a pot rack, sunny breakfast area, and walk-in pantry. A cozy living and dining room offers a comfortable gathering space, while upstairs bedrooms retain original wide pine floors and vintage details. Both bathrooms have been updated, and the oil tank, on-demand hot water heater, pressure tank, and well pump have all been recently replaced. Garden beds and a painted harlequin porch floor add personality outside, while the covered porch invite you to enjoy morning coffee and the rhythm of village life. A rare opportunity to own a property with a story to tell and the potential to make it your own. Buyers who appreciate historic homes and are comfortable with a project will find opportunities to build on its existing character.

39 Pikes Falls Rd, Jamaica

$275,000

3 Beds ⋅ 1 Baths ⋅ 5114102 MLS

Just right! All spiffed up, shinny and ready to move right in. Sweet aging in place home on one level, level back yard, and minutes from grocery stores, hospital and Memorial Park! Just starting out? 3 bedrooms gives you room for expansion, hobbies or an aging parent. This affordable home should go most programs, has lots of light, and is a perfect beginner home. Check it out and start a new chapter; leave the rentals behind and invest in your future!

43 Winter St, Brattleboro

$139,000

2 Beds ⋅ 1 Baths ⋅ 5114039 MLS

Finally! An affordable bit of Vermont! Claim it as your own....either enjoy this older mobile home, or replace it with another or a tiny home...log cabin? Sitting near the road and utilities, it is easy to get to on a snowy ski day. The 4.6 acres runs back to Old County road and is a rolling landscape for nature walks and camping out. Choose either Mount Snow or Okemo for your day trip skiing...or hike the Pinnicle Trail only minutes away. Southern Vt has a lot to offer and this is just the starting point.

133 Valley Cemetery Rd, Athens

$129,000

5114033 MLS

INVESTORS, LANDLORDS & OWNER-OCCUPANTS - HERE’S YOUR OPPORTUNITY! Whether you’re looking to expand your rental portfolio, create two income-producing units, or live in one unit while the other helps offset your mortgage, this two-unit, up-and-down multifamily property is ready for its next chapter. The heavy lifting has already begun! The current owner has completed the deconstruction, removing all drywall and taking the interior down to the studs, creating a true blank canvas for your vision. Building permits were issued for the deconstruction work already completed. Additional improvements have been made throughout the property, including replacement of the existing chimney with an insulated stainless steel chimney, as well as upgrades to the roof, heating, and electrical systems. The first-floor unit has its existing systems in place, while the second-floor unit will require systems to be installed as part of the renovation. Outside, enjoy a nice, flat yard and plenty of paved parking. With much of the initial demolition already completed, you can focus on designing and finishing the property to fit your investment goals. Bring your contractor, bring your vision, and bring your plans - this clean slate is ready for its next transformation! Come take a look and see what you can create.

139 Frost St, Brattleboro

$349,000

3 Beds ⋅ 1 Baths ⋅ 5113983 MLS

This charming 3 bedroom, 1 bathroom ranch in a quiet Dummerston neighborhood offers comfort, versatility, and plenty of indoor and outdoor space. The wide-open living area includes an updated kitchen, beautiful wood flooring, and ample natural light. A wood stove adds the perfect touch for cozy fall and winter evenings. There’s plenty of flexible space for hobbies, a home office, or whatever suits your needs. The basement features a photography darkroom, a partially finished bathroom, and great potential for additional finished living space. Outside, enjoy a spacious, level yard and a large deck perfect for relaxing or entertaining, along with an attached one-car garage. Just 5 minutes from Putney Village and the I-91 exit, this home offers a wonderful blend of convenience, character, and possibilities!

50 Sugar Maple Dr, Dummerston

$339,000

2 Beds ⋅ 2 Baths ⋅ 5113651 MLS

There’s so much to love about this home! Enter through an enclosed mudroom, perfect for storing all your outdoor gear. The kitchen offers abundant storage, a dedicated baker’s counter, and a convenient breakfast bar with seating. Beautiful hardwood floors flow throughout the kitchen, dining, and living areas. The first floor features two bedrooms and two full bathrooms, while the basement adds three additional heated, finished rooms, offering endless possibilities for a home office, playroom, hobby space, or more! Step outside to enjoy the deck, perfect for grilling and dining al fresco, overlooking a flat, open yard. Plus, the home is conveniently located just down the road from the town pool and recreation area!

167 Silver Ln, Vernon

$199,000

3 Beds ⋅ 1 Baths ⋅ 5113644 MLS

Looking for an affordable home with a little personality? You've found it in this colorful 3-bedroom, 1-bath home in the historic village of Whitingham, Vt. Set on 0.10 acres along a quiet, paved street with town sewer, the home is surrounded by some of Southern Vermont’s best lakes, including Sadawga Lake and Harriman Reservoir. Step inside through the French doors that separate the mudroom from a flexible living space that can become a dining room, home office, sitting area, or whatever works best for you. The first floor also includes the full bathroom, laundry area, and primary bedroom with a walk-in closet. The kitchen features an eat-in island for casual dining and opens to a spacious great room, where a large picture window brings in plenty of natural light. Bold colors throughout give the home a fun, playful energy and make each room feel a little different from the next. Keep the color, tone it down, or make it completely your own. Upstairs, two additional bedrooms continue the home's bright and bold personality. A door off the living area leads to the fenced backyard, where you can relax and enjoy the sounds of nearby Sadawga Brook on the front porch of the shed, which can be used for storage, a workshop, or play space. Major systems have been recently updated including the well pump and pressure tank (new in 2016), furnace (new in 2021) and water heater (new in 2024). The home is just 13 minutes to Wilmington, 16 minutes to Hogback Mountain’s 100-mile view, 23 minutes to Marlboro, 25 minutes to Mount Snow, and roughly 40 minutes to Brattleboro to the east and Greenfield, Mass., to the west.

105 School St, Whitingham

$335,000

3 Beds ⋅ 2 Baths ⋅ 5113619 MLS

Come take a look at this three bedroom and two bath chalet in the B Section of Chimney Hill with terrific amenities. Relax on the main level in an open concept living, dining and kitchen space, living room has a woodstove and sliders to the deck to enjoy the country side views, a bedroom and a full bath. Upstairs has two more bedrooms and a full bath. An exclusive members-only clubhouse with indoor/outdoor pools, hot tub, fitness room, arcade, kids playroom, media room, library/reading nook, kitchen area with bar, BBQ area and a playground. Throughout the complex there is a fishing pond, trail system, tennis courts, ice skating rink, hiking trails and snowmobile access. Minutes from skiing, fine dining, golfing, boating, downtown Wilmington and so much more!

19 View Rd, Wilmington

$339,000

3 Beds ⋅ 2 Baths ⋅ 5113538 MLS

Located in the desirable Black Mountain Road area, this cozy log home includes an attached two-car garage with a workshop area, a three-season porch, and a wraparound deck. The lower level is accessible from the garage and opens into a spacious tiled mudroom. An open staircase leads to the main floor, which features three bedrooms, 1¾ baths, a living room, and a country kitchen with a dining area. The basement provides abundant unfinished space for a workshop, studio, or other creative pursuits, along with laundry, sink and a workbench. Additional outbuildings include small storage sheds. The home needs some TLC but offers worthwhile potential in a country setting, so close to town. The owners are continuing the cleanout process, and additional photos will follow. Please note that the large stones are not included.

625 Black Mountain Rd, Brattleboro

$289,900

5 Beds ⋅ 3 Baths ⋅ 5113467 MLS

CASH OR REHAB LOAN ONLY – PROPERTY NEEDS WORK! Ski lodge within walking distance to the Chimney Hill Clubhouse, offering 5 bedrooms, 2½ baths, and plenty of space to create your ideal Vermont getaway. Three levels include a family room with wood stove, laundry, mudroom, kitchen with island, dining area with cathedral ceiling, sunken living room with fireplace, and sliders to a multi-level deck. Natural light and woodwork add to the mountain-lodge character. Enjoy Chimney Hill’s extensive four-season amenities, including indoor/outdoor swimming, tennis, pickleball, hot tub, fitness room, skating, hiking, biking, snowmobiling, playground, clubhouse, and more. Conveniently located minutes from skiing, dining, shopping, breweries, festivals, and the Green Mountain National Forest. Property is being sold AS-IS and requires renovation. Cash sale or rehab financing required. Bring your vision and make this mountain retreat your own! This property is eligible under the First Look Initiative which expires after 30 full days on market. No investor offers until first look period expires. No offers regardless of buyer type will be negotiated within the first 7 days of listing.

3 Lightning Ledge Way, Wilmington

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