Beautiful woodsy contemporary chalet located just down from the Chimney Hill Clubhouse in Wilmington. This charming home has nearby access to the country village of Wilmington, Lake Whitingham, is a short drive to the Mt Snow ski resort, and has nearby to one of the best hiking areas in Southern Vermont, thanks to the community adjacent Green Mountain National Forest. It sits nestled on a private lot in the Chimney Hill community on a quiet side road with easterly mountain views. Inside you will find a lovely open concept living space with vaulted ceilings and exposed woodwork, great natural light thanks to large windows, a spacious great room with wood burning fireplace, brick hearth, and exposed beams, kitchen with island and spacious dining area, wood flooring, a main floor bedroom and full bath, upstairs bedroom with sleeping loft, a full walkout lower level family room partially finished with bunk room and third almost finished bath and laundry, lower level foyer, and hot tub area, ample storage, and more. This includes the amazing Chimney Hill amenities of indoor and outdoor pools, clubhouse, theater, gym, hot tub, basketball court, tennis courts, winter ice skating, and a la carte services like plowing and trash, to afford yourself plenty of downtime, not upkeep. Septic sized for 3 bedrooms full time use.
Listed by Adam Palmiter of Berkley & Veller Greenwood/Dover
This attractive country property covers over 10 acres of beautifully landscaped grounds, bordered by a tranquil brook and peaceful woodlands. The setting provides a serene environment ideal for enjoying nature and outdoor activities. The single-level home features an open-concept main floor, offering a seamless flow between living spaces. It includes a spacious bedroom, a full bathroom, laundry, and office space, making it suitable for comfortable daily living. The walk-out basement is fully finished and designed for both relaxation and functionality. It includes a large family room, an additional bedroom, a full bathroom, and a utility room. Relax on the screened porch, which provides soothing sounds of the natural surroundings. A heated three-car garage with an integrated workshop connects directly to the mudroom and entryway, offering convenience and ample space for projects. Above, a spacious studio is accessible via a private deck. The studio is equipped with a full bathroom and kitchenette, making it ideal for guests or remote work. Additional amenities include tractor shed, garden shed, generator and RV hookup. Situated in Westminster West village, the property offers easy access to nearby towns, numerous farm-stands, and publicly accessible lands with 29 miles of hiking trails, including the especially beloved spot known as the Pinnacle.
Listed by Heidi Bernier of Berkley & Veller Greenwood Country
A picturesque, private home with lovely views from every room. Set back from the road in a pastoral setting, it is quiet and tranquil. The moment you enter through the front covered porch, you are greeted by abundant natural light and breathtaking views. The open floor concept is inviting, and the beautiful timbers were milled from the land. The original owner, who has owned the home for 47 years, adores it. The spacious and peaceful living room features a soothing fireplace. The first floor has a large primary bedroom, a full bath, a laundry room, and another room perfect for an office or bonus room. Upstairs are two spacious bedrooms and another full bathroom. The full basement is ideal for a workshop, featuring additional heat with a wood boiler and a walk-out exit. The 10 x 27 screened-in porch is ideal for family gatherings, and the expansive Trex decks, along with the alluring pool and hot tub, will create lasting memories. The location offers seclusion and accessibility, situated minutes from the historic Guilford Country store and Interstate 91. You will love coming home and never want to leave. Additional 2.8 +/- acreage available for $89,000 only with house purchase.
Listed by Kristen Ziter Taylor of Brattleboro Area Realty
Spacious ski chalet in the Chimney Hill community with easy access to trails, hiking, lakes, and nearby Mount Snow. Just down from the rec center and clubhouse sits this well maintained home with easy access, ample parking, a level back yard, and nice privacy, yet with all the conveniences of community living. The interior has a vaulted open concept living space with natural light and large windows, natural woodwork throughout, a kitchen with stainless appliances and breakfast bar, a spacious dining area open to the living room with gas fireplace and brick hearth, a main floor bedroom and full bath as well as a large mudroom for all your gear, 2 upstairs bedrooms including a large bunk room with great closet space, as well as a second full bath recently renovated, a finished walkout lower level with games, additional sleeping space, and ample room to spread out. There is also a large storage and utility room for seasonal storage or owner lock out space. There is a garage shed outside for snowmobile, a fire pit, and large entertaining deck. This comes with all the great Chimney Hill amenities including road maintenance, community water, clubhouse with indoor and outdoor pools, hot tub, game room, theater, playground, tennis courts, basketball, gym, and more. There are also a la carte services including plowing, sanding, and trash pickup. A truly unique spot that affords Vermont charm and serenity, with easy management.
Listed by Adam Palmiter of Berkley & Veller Greenwood/Dover
Welcome to 494 West River Street, a classic Vermont retreat nestled on more than 10 picturesque acres along the scenic West River in South Londonderry. Built in 1965, this four-bedroom, two-bath ranch-style home offers a rare opportunity to enjoy the natural beauty, privacy, and year-round recreation that make Southern Vermont such a sought-after destination. Set among mature trees and open spaces, the property provides a peaceful setting where the sights and sounds of the river create a truly relaxing atmosphere. Whether enjoying morning coffee on the porch, gathering with family and friends, or simply unwinding after a day outdoors, you'll appreciate the connection to nature that surrounds this special property. Outdoor enthusiasts will love the proximity to some of the area's most treasured recreational resources. Also Views of Magic Mtn from house! The renowned West River Trail is just a short walk away, offering miles of scenic hiking, biking, cross-country skiing, and snowshoeing. Nearby access to the Green Mountain National Forest and Winhall Brook Campground provides endless opportunities for exploring Vermont's beautiful landscape, while the West River itself invites fishing, kayaking, and peaceful riverside enjoyment. Conveniently located in the heart of Southern Vermont, the property is just minutes from the charming villages of South Londonderry and Londonderry. There, you'll find local shops, restaurants, farmers markets, and a welcoming small-town atmosphere. World-class skiing, golf, and year-round events at Stratton and Bromley Mountains are also within easy reach, making this an ideal base for every season. Whether you're seeking a full-time residence, a weekend escape from city life, or a vacation property to enjoy with family and friends, 494 West River Street offers a unique combination of riverfront beauty, acreage, privacy, and recreational access in one of Vermont's most desirable four-season locations
Listed by Bob Maisey of Berkshire Hathaway HomeServices Stratton Home
Escape it all to this beautifully efficient exposed beam log home on over thirty five acres, twenty six or so added by the current owners. Better even, you'll abut the conserved 777 acre Windmill Hill Pinnacle Association with fabulous hiking trails including the Pinnacle Cabin you can book for overnight ridgeline trekking stays. Solar panels over the detached garage, leased Tesla Powerwalls for seamless power outage prevention, western moon and sunsets from your wrap around covered deck, two toasty woodstoves and a detached sauna to soothe you so you don't sweat the small stuff. Hyper fast internet with 325 Mbps down, 413 up so you can work remotely, if you must, surf the net to your heart's content or become a luddite and give it all up. Just 45 minutes from Stratton, this wonderful south eastern Vermont town has a whopping population of 380. Shopping in Bellows Falls, Grafton (cheddar!), Westminster, Putney & Walpole. Chester, Londonderry and Brattleboro for the big time. Amazing tree house in the canopy behind the house with a zipline for onsite adventure. Wildlife, recreation and southern, easily reachable Vermont on fantastic Old County Road. Traditional life, privacy, without losing all that's modern. VAST trail access less than two and a half miles north. Lister card states 3BR home; basement twin set of bunk beds are in the 3rd practical sleeping room. Sauna optional: Sellers would be happy to remove it if you prefer not to have it on site.
Listed by Clayton-Paul Cormier of Maple Sweet Real Estate
This is a rare turnkey quality home that's been completely refurbished since 2018. The immense list of upgrades includes: completely new paint inside and out, electric overhaul, heat pump hot water heater, bulkhead and exterior foundation waterproofing, fully remodeled bathrooms, all new windows and doors, new lighting throughout, wainscotting, new septic tank and the list goes on. There are 2 bedrooms with hardwood and a full bath downstairs. The primary bedroom, full bath and closets make up the 2nd floor. There are 4 heating zones to customize your comfort. Cut your reliance on oil with your newer pellet stove and wood stove for all but the coldest months. When you step out onto the new screened in porch off the back of the house, you're surrounded by calm. There are no visible neighbors. Let your furry friends roam free in the fenced in backyard while keeping unwelcome guests out of your garden. No worry about the weather when you're parked in your detached 2 car garage that has plenty of additional storage space. The large vegetable garden is just waiting for your inspiration. Situated back from the road on just over 4 acres and surrounded by a beautifully landscaped flat yard and woodland. This is a property to enjoy from the inside to the outside.
Listed by Victoria Woods of Brattleboro Area Realty
Located just minutes from the slopes of Mount Snow, the pristine waters of Lake Raponda, and the expansive Harriman Reservoir, this property offers the ideal combination of convenience, recreation, and opportunity. With ample space and zoning flexibility, you have the unique chance to build an Accessory Dwelling Unit (ADU) on-site, perfect for generating rental income, hosting guests, or creating a private retreat. Whether you're a winter sports enthusiast, a lover of water activities like kayaking, paddleboarding, and fishing, or simply seeking a peaceful escape, this location is a gateway to year-round adventure. Explore skiing and snowboarding, hike and bike scenic trails, or enjoy the vibrant local food and arts scene in nearby downtown Wilmington. Imagine the possibilities: your dream home, an income-producing property, or a combination of both, all in a setting that perfectly captures the beauty and charm of Vermont.
Listed by Colt Hazell of Flex Realty, Flex Realty Group of Flex Realty
Recently repositioned with a price improvement, this move-in-ready chalet offers even greater value in one of Dover's most desirable mountain neighborhoods. Nestled on a corner parcel in the desirable Dover Hills area near Mount Snow, this beautiful chalet offers the perfect low-maintenance four-season retreat. Designed for easy upkeep and effortless enjoyment, the home combines warm mountain charm with modern amenities, abundant natural light, and true move-in-ready convenience. Ideally located just minutes from skiing, snowmobile trails, golf, hiking, lakes, shopping, and dining, this property is perfectly suited as a year-round getaway or income-producing vacation rental. After a day on the slopes, relax beside the cozy wood-burning fireplace or unwind in the outdoor hot tub while taking in the peaceful mountain setting. The thoughtfully updated interior features vaulted ceilings, natural woodwork, and oversized windows that fill the home with sunlight. A stunning kitchen with stainless steel appliances opens to a spacious dining area and wrap-around deck, creating an ideal space for entertaining or quiet evenings outdoors overlooking the landscaped yet low-maintenance grounds. The main level includes a comfortable bedroom and full bath, while upstairs offers 2 additional bedrooms, and bath with shower and soaking tub. The convenient mudroom entries for easy four-season living. Outside, ample parking, a paved road location, excellent sun exposure, generous lawn space for pets or play. Beautiful furnishings are included, making this a true turnkey opportunity near some of Southern Vermont's best outdoor recreation. Whether you're seeking a relaxing second home, ski retreat, or investment property, this exceptional chalet must be seen to be appreciated.
Listed by Donald Koelsch of Deerfield Valley Real Estate
Step into an 1880s Victorian re-imagined for the 21st century. Located moments from downtown Brattleboro, this 3-bedroom, 3-bath home blends historic craftsmanship with a cutting-edge deep-energy retrofit. Enjoy easy access to shops, dining, the Amtrak station, and the Retreat Trails from a peaceful, residential setting. Unlike typical historic renovations, this property underwent a from-the-studs rebuild in 2018, serving as a pilot for high-performance building science. It is now fully electric and fossil-fuel free, featuring : Air-to-water heat pump for heating/cooling and an Energy Recovery Ventilation (ERV) system for superior indoor air quality. The home also has a super-insulated, airtight building envelope ensuring year-round comfort and efficiency, with a durable standing seam roof equipped with solar panels. The interior honors its heritage while embracing sustainable, modern design, using eco- friendly materials: copper countertops, natural linoleum flooring, and Energy Star appliances. Modern mechanical systems and smart features throughout, you get turn-key Peace of Mind.: Every major system-from insulation to infrastructure-is new, offering a rare level of durability in a vintage home. 81 Chapin Street is more than a renovation; it's a blueprint for the future. For those seeking environmental responsibility without sacrificing historic charm, this is a truly unique opportunity.
Listed by John Hatton of Berkley & Veller Greenwood Country
Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated June 17, 2026 8:25 AM UTC
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