Windham County

MLS Number 5089829

• Residential Single Family
• Full Bath 1
• Address 116 Teacher Road
• Bedrooms 4
• Bathroom 3

Set on 14.4 acres bordering the beautiful Green Mountain National Forest, this lovingly maintained 4-bedroom, 2.5-bath Vermont retreat offers the perfect combination of privacy, comfort, and year-round recreation. Currently operating as a successful Airbnb with repeat renters, the property is being offered fully equipped as a turn-key vacation rental opportunity or exceptional full-time residence. Conveniently located just 20 minutes from Stratton Mountain and Mount Snow. The south-facing home features bright, open living and dining spaces with large picture windows showcasing beautiful views in every direction. A fieldstone hearth with wood stove creates a warm and inviting atmosphere for entertaining, while the kitchen offers abundant storage. The main level includes three bedrooms, a ¾ bath, and a sun-filled mudroom/sunroom with wall-to-wall windows and its own propane stove. Upstairs, the spacious primary suite or bunk room retreat includes a full bath, cedar walk-in closet, and mountain views. The basement with half bath, and attached 2-car garage provide excellent storage, workshop, recreation, or future living space potential. Outside, enjoy expansive lawns, meadows, a screened gazebo, private trails, mature forest, stone walls from an old homestead, and a year-round creek. Endless hiking, snowmobiling, ATV riding, and outdoor adventure await right from the property. Energy-efficient upgrades include owned REC solar panels, owned Tesla backup batteries, Daikin heat pumps and mini splits, rebuilt chimney, generator-ready setup, multiple heating options, and high-speed Starlink internet with mesh coverage. Tucked at the end of a town-maintained dead-end road, this is a rare opportunity to own a true Vermont escape.

Listed by Carrie Mathews of Winhall Real Estate

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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MLS Number 5074646

• Residential Single Family
• Full Bath 2
• Address 3148 Route 11
• Bedrooms 3
• Bathroom 2

Acreage with so much potential! Looking for a piece of Vermont to call your own? Look no further then this beautiful home looking for new owners to love and enjoy it like the current owners have. Perfectly situated in Londonderry, Vermont near Bromley, Stratton, Okemo, and Magic Mountains. The sellers have done updates to the home and property but have left spots for the new owners to still put their own finishing touches on the place! The house has 3 bedrooms and 2 bathrooms, a very spacious living room, and separate dining room, and offers several great porches/decks and a hot tub. The house also has a bonus room that could be used as an office with a private outside entrance if you wanted to work from home. The property also boasts 14 acres of mostly wooded acreage with a 3 bay pole barn, 1.5 bay garage, and a couple other outbuildings. So many great options and potential in this property-it could make a great primary residence, vacation home, possibly subdivide and make a family compound, or so many other options. Don't let this one get away, schedule your appointment today!

Listed by Erin Kendall of EXP Realty

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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MLS Number 5086258

• Residential Single Family
• Full Bath 2
• Address 14 High Top Road
• Bedrooms 3
• Bathroom 3

Section B Cul de Sac. Fabulous large house on an oversized lot! First time on the market in 20 years! 3+ bedrooms, 3 bathrooms, gas fireplace, large deck, workshop space, large driveway with plenty of level parking. Mudroom entry, laundry room, open concept living, dining and kitchen. Newer appliances, second fridge, first floor bedroom and bathroom, plus a study and two glass rooms that are connected; one was previously a hot tub room. Second level features a primary bedroom with ensuite bath, walk-in closet, and two additional bedrooms with a shared bath, and one has an oversized closet. Vaulted ceiling, natural woodwork, tons of privacy. This is it! Start living the dream of your resort getaway lifestyle. Chimney Hill is situated on 1,200 acres, with 550 owned in common by the members. Owners enjoy all the recreation amenities CHOA offers, including our exclusive member-only clubhouse located at 2,00' in elevation with an outdoor heated pool, playground, basketball and tennis, indoor heated pool and hot tub, fitness room, toddler playroom, aprs ski lounge, fully equipped kitchen, reading nook, community room, arcade, extensive trail system, seasonal pickleball and ice skating, and a stocked fishing pond. Plus, enjoy all that the Deerfield Valley and Southern Vermont offer including world class skiing and shredding, snowmobiling, snow shoeing, hiking, biking, boating, theater, music, breweries, distilleries, fine dining, flea markets, antiques, unique shopping, horseback riding, and so much more!

Listed by Sigrid Pickering of Chimney Hill Realty

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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MLS Number 5084477

• Residential Single Family
• Full Bath 2
• Bedrooms 4
• Bathroom 2
• Square Feet 2,580

Nestled among the trees in the sought-after Snow Mountain Farms community, this beautifully maintained four-bedroom home is just 7.6 miles to Mount Snow and 13 miles to Stratton Mountain Resort. The welcoming front porch leads to a spacious wrap around deck, creating an ideal setting for entertaining or simply enjoying the peaceful natural surroundings. The main living area features pine floors and a cozy wood-burning fireplace, delivering that classic Vermont feel. The primary suite with its own bath, along with two additional bedrooms, are located on the main level for easy living. The lower level expands the living space with a workshop, a recreation room complete with an indoor hot tub, and direct walkout access to the backyard. A fourth bedroom and a versatile bonus room provide additional flexibility for guests, a home office, or hobbies. The community offers an indoor pool for year-round enjoyment and a outdoor tennis court. Whether you're seeking a full-time residence or vacation getaway, this home is ready to deliver a mountain lifestyle at its best.

Listed by Jessica Citera of Cummings & Co

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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Your Questions & Comments I have a question about the property at 1229 Sheldon Hill Road Wardsboro VT 05355 (#5084477).

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MLS Number 5060691

• Residential Single Family
• Full Bath 2
• Address 794 White Road
• Bedrooms 2
• Bathroom 2

Enjoy the best of Vermont living in this thoughtfully renovated home on a paved country road in Windham. Renovated down to the studs, this property offers upgrades inside and out-new standing seam roof, new siding, new windows, full-house generator, new central air and heating systems, plus new electrical and plumbing systems upgraded to 200 amps. The home is insulated with rockwool and foam board, and the foundation is sealed with full drainage installed around the perimeter. Step inside to a light-filled interior with new flooring, walls, and fixtures throughout. The spacious kitchen features Big Chill appliances and opens to a lovely front porch overlooking the old stone walls that border the property. A fenced-in yard makes this ideal for pets, and the water filtration system with UV light ensures clean living. You'll also find a new washer and dryer, a new septic system, and thoughtful design throughout. Close to skiing at Magic (10 min), Bromley and Stratton (20-25 min), and just 15 minutes to downtown Londonderry. Hike, bike, or snowmobile with access to VAST trails and Timber Ridge nearby. Come see what makes this rare offering a great opportunity!

Listed by Erica Reynolds of Southern Vermont Realty Group

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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MLS Number 5075776

• Residential Single Family
• Bedrooms 2
• Bathroom 2
• Square Feet 2,016
• Acreage 2.00

Looking for a turn key Vermont retreat to call your own? This beautiful home built in 2009 and complete with a newer barn, chicken coop, treehouse, and storage shed could be what you have been dreaming of. Conveniently located just a short drive to 91, not far to the Vast trail access for snowmobiling, and near to many Vermont mountains for skiing or snowboarding. The warm and welcoming home features two bedrooms, a multipurpose loft space, a spacious bathroom with a lovely soaking tub, a gorgeous kitchen, spacious living room upstairs! From there you can walk outside onto the covered section of porch or the deck overlooking the spacious lot complete with corrals for animals. Back inside you can walk down the steps to the walk out basement with the utility room, a space currently used as a gym, a cozy living room with lots of space, and a another bathroom. Walk outside and admire the beautiful stone walls and steps, flower beds, and peaceful setting. The barn has so much potential and depending on what you need it could be used for animals, storage, garage or something else you dream up. The extra storage shed affords more storage space. The treehouse overlooks the house from the back yard, just waiting to be used. Set up your appointment to view this home today! Please do not pull in driveway without appointment.

Listed by Erin Kendall of EXP Realty

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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Your Questions & Comments I have a question about the property at 35 Upper Bartonsville Road Rockingham VT 05143 (#5075776).

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MLS Number 5087887

• Residential Single Family
• Full Bath 2
• Bedrooms 4
• Bathroom 3
• Square Feet 3,263

Welcome to this spacious contemporary home located on the desirable Hartley Hill Road, conveniently situated near Saxtons River, Bellows Falls, Putney, and I-91. Built in 2008, this well-maintained home offers quality craftsmanship including a brand new roof installed April 2026, high-end utilities, and modern comforts throughout. The finished, walk-out lower level features radiant heat, abundant natural light, and exterior access from three sides of the home. This floor is home to the spacious primary suite including a luxurious ensuite bathroom complete with a soaking tub, dual sinks, a beautiful walk-in shower, separate toilet room, and a large walk-in closet. This level also offers a generous bonus room, laundry room, and utility room. Upstairs, enter through the back deck into a welcoming entryway leading to the expansive modern kitchen, featuring granite countertops, a large center island with pendant lighting, and plenty of space for entertaining. The open-concept kitchen, dining, and living area is centered around a striking staircase that ties the space together beautifully. This level also includes an additional bedroom and a convenient half bath. The upper floor offers two more spacious bedrooms and a full bathroom with dual sinks and a walk-in shower. Outside, relax on the deck overlooking the pool while enjoying the privacy and tranquility of the surrounding rural countryside.

Listed by Chelsea Cary of Barrett and Valley Associates Inc.

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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Your Questions & Comments I have a question about the property at 1488 Hartley Hill Road Westminster VT 05158 (#5087887).

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MLS Number 5094642

• Residential Single Family
• Full Bath 1
• Bedrooms 2
• Bathroom 1
• Square Feet 1,576

Perched atop this scenic hillside on 6 acres, this distinctive contemporary home and classic gambrel two-story barn once enjoyed sweeping easterly views to Mount Wantastiquet and distant Mount Monadnock. Glimpses of the long-range views exist but will need to be reclaimed. Located on highly desirable Pleasant Valley Road in West Brattleboro, the property offers an exceptional combination of rural Vermont charm, privacy and convenience, with easy access to town. The beautiful Pleasant Valley Reservoir and the recreational opportunities provided by its protected land, trail system and class 4 road network are an underutilized outdoor paradise just down the road. The home's striking flat roof design, redwood siding, and clean mid-century modern influences create a timeless architectural aesthetic. Inside, the open concept living/dining and kitchen area is filled with natural light from the expansive windows that frame the surrounding landscape. An East/SE facing corner deck provides the perfect setting for morning coffee and sunrise views. The main level features two bedrooms and a full bath updated in 2026. The finished walkout lower level offers a spacious additional living space. The impressive gambrel barn once housed horses in its 3-5 stall lower level and has water and power. The top level of the barn is open clear span with a drive-in door ideal for vehicles and equipment storage, a wood shop, workshop, studio space or a variety of other uses including a possible second dwelling unit with applicable permits. The open land in front of the barn was once a dressage arena and provides an excellent level outdoor space for recreation, animals or agriculture. The remainder of the property includes a mix of open field, young growth forest and established yard areas surrounding the home with abundant room for large gardens and outdoor fun. Despite its peaceful country setting skiing, golf, hiking and biking are only minutes away. A rare one-of-a-kind Vermont property.

Listed by Chris Long of BHG Masiello Brattleboro

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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Your Questions & Comments I have a question about the property at 211 Pleasant Valley Road Brattleboro VT 05301 (#5094642).

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