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77 Villager Loop, Dover
$563,300
5 Beds ⋅ 3 Baths ⋅ 5106287 MLS
This one won't last long! Beautifully maintained and updated chalet in the Dover Hills, just a short drive from the Mount Snow ski resort. The current owners have taken care to keep the original charm of this home while adding rustic features and recent updates to allow for turn key enjoyment. Off the side of a private paved loop, this home sits on a level parcel with ample parking, spacious yard, fire pit, and winter views, without having too much to maintain. Inside you are treated to a gorgeous vaulted great room with rustic wood paneling, updated gas fireplace with brick hearth, large open kitchen with breakfast bar, efficient direct vent heating system, bay windows for great natural light, main floor bedroom currently used as a second dining area, and lovely tv area. This leads out to the spacious deck for entertaining. The upper level has a large primary suite with partially updated jack and jill bathroom, as well as a large second bedroom. The finished walkout lower level has a full family room space, ping pong table and ample room to spread out, two more bedrooms and a third full bath, as well as a dining space under the deck leading out to the yard. Other less obvious updates include an updated metal roof and appliances. One bedroom in the lower level does not have legal rental egress. Septic is grandfathered as of 2007 for 5 bedrooms.

77 Villager Loop, Dover

559 Parker Hill Rd, Rockingham
$562,500
2 Beds ⋅ 3 Baths ⋅ 5087641 MLS
Nestled on Historic Parker Hill, this charming residence sits on a generous 10-acre lot that blends open spaces with woodlands, offering both privacy and natural beauty. The home features classic post and beam construction, highlighted by a cathedral ceiling and hardwood floors that create a warm and welcoming atmosphere. Large windows provide captivating views of the surrounding landscape, making every room feel connected to nature. The spacious layout allows for easy flow between the open concept living and dining areas, complemented by a country kitchen with hardwood floors. A loft, complete with built-in bookcases, offers additional living space and overlooks the main area. The handsome brick chimney with a wood stove not only provides warmth but also adds a touch of rustic ambiance. On the first floor, the luxurious primary bedroom includes an ensuite bathroom and a soaking tub, as well as a bank of large windows that frame the picturesque views. Upstairs, a cozy bedroom is equipped with a half bath and built-in storage, providing comfort and functionality. Additional Spaces and Amenities: An attached 2-car garage offers convenient workshop space, along with a heated 18x13 room on the second floor that is perfect for a home office, or studio. The property also includes an equipment shed and wood storage cribs, catering to practical needs. Ideally located less than ten minutes from I-91 exit 6, the home is within easy driving distance of Okemo (30 minutes away) and the nearby towns of Chester, Springfield, and Bellows Falls. This location combines tranquility with accessibility to regional amenities and attractions.

559 Parker Hill Rd, Rockingham

9 Beaver Pond Ln, Jamaica
$560,000
4 Beds ⋅ 4 Baths ⋅ 5094302 MLS
Rare Multi-Dwelling Retreat with Endless Possibilities A truly exceptional and meticulously maintained property featuring three separate residences on one beautifully landscaped lot, a setup buyers often dream about but rarely find. The main residence is a stylish 2-bedroom, 2-bath contemporary home thoughtfully designed for comfortable living. Built with sustainability in mind, the home features an environmentally friendly geothermal system that provides efficient heating and cooling year-round. Complementing the main home are two charming tiny houses, each with its own unique character and appeal. Whether used for guests, rental income, extended family, or creative workspace opportunities, these versatile structures offer tremendous flexibility. The grounds are nothing short of spectacular. A beautiful pond with a sandy beach and cascading waterfall creates a private oasis right outside your door. Mature landscaping throughout the property provides beauty, tranquility, and a clear sense of pride of ownership. Adding to the property's appeal is a septic system permitted for three two-bedroom residences. This substantial infrastructure provides valuable flexibility for future use. Subject to applicable permits and approvals, the existing tiny houses could potentially be replaced with larger two-bedroom cabins, or bedroom capacity could potentially be reallocated to an expanded main residence. Properties offering multiple residences, income potential, privacy, natural beauty, and convenient access to Stratton are exceptionally rare. Here, much of the groundwork has already been completed: the infrastructure is installed, the homes are in place, and significant future potential remains. Don't miss this unique opportunity to own a one-of-a-kind Vermont retreat offering flexibility for today and possibilities for tomorrow.

9 Beaver Pond Ln, Jamaica

8 Deer Run, Wilmington
$560,000
4 Beds ⋅ 4 Baths ⋅ 5093915 MLS
Located in the desirable Chimney Hill community, this beautifully maintained 4 bedroom, 4 bath home offers the perfect combination of comfort, convenience, and year-round recreation. Designed for gathering and relaxing, the open-concept floor plan features vaulted ceilings, abundant natural light, and seamless flow between the kitchen, dining, and living areas. A cozy gas fireplace creates a warm and inviting atmosphere after a day spent exploring Southern Vermont. The spacious kitchen opens to the main living area, making entertaining effortless, while expansive windows bring the outdoors in. Step outside to the large deck, ideal for summer barbecues, morning coffee, or simply enjoying the wooded surroundings. A direct-entry garage provides convenience in every season, and the finished lower level offers additional space for recreation, fitness, guests, or a media room. With four bedrooms and four baths, there is plenty of room for family and friends to gather comfortably. As a homeowner in Chimney Hill, you'll enjoy access to exceptional community amenities, including indoor and outdoor swimming pools, pickleball and tennis courts, a fitness center, clubhouse, skating rink, playground, and access to hiking and snowmobile trails. Ideally located just minutes from Mount Snow, The Hermitage Club, Lake Whitingham, and downtown Wilmington, this property places the very best of Southern Vermont recreation right at your doorstep. Whether you're seeking a full-time residence, weekend getaway, or investment property, 8 Deer Run Lane offers an outstanding opportunity to enjoy Vermont's four-season lifestyle in one of the area's most sought-after communities.

8 Deer Run, Wilmington

509 Silver Ln, Wardsboro
$560,000
4 Beds ⋅ 4 Baths ⋅ 5086516 MLS
Warm and Inviting Home in Snow Mountain Farms. Nestled in the peaceful far side of Snow Mountain Farms, this warm and inviting home offers access to an indoor swimming pool, outdoor tennis courts, and a recreation center all for just $450 annually. Featuring beautiful cathedral ceilings and a wood-burning fireplace, the open-concept living area seamlessly connects the kitchen and dining spaces, creating the perfect setting for gatherings with family and friends. This home is ideally located near many of southern Vermont’s best seasonal attractions, with Mount Snow and Stratton just a short drive away. In winter, enjoy easy access to nearby snowmobile trails; in the warmer months, explore the area by mountain bike or on scenic hikes. The main floor includes three bedrooms and two full baths, while the primary suite occupies the second floor, offering extra privacy. The large recreation room downstairs provides space for games, movies, or simply relaxing with loved ones. Recent updates include a newer propane furnace, hot water heater, and a fully renovated kitchen featuring granite countertops and stainless-steel appliances. Enjoy panoramic views through floor-to-ceiling windows or unwind on the wrap-around deck, perfect for soaking in Vermont’s natural beauty.

509 Silver Ln, Wardsboro

149 Dix Ln, Whitingham
$555,000
4 Beds ⋅ 2 Baths ⋅ 5057333 MLS
Tucked away on a quiet, town-maintained dead end road this Vermont country homestead offers the perfect blend of charm, privacy, and practicality. Set on 34+ acres, this property has woodlands, pasture and hay fields that have supported a working farm with livestock for the past 5 years. This property is well suited for those seeking a working homestead or a recreational retreat. The four-bedroom home, with all new windows and siding, is warm and welcoming, with an open floor plan anchored by a dramatic three-sided fireplace and woodstove in the living room. A wraparound deck and fenced yard extend the living space outdoors, ideal for a gathering or simply taking in the peaceful surroundings. Upstairs, an open loft area connects the second-floor bedrooms, offering a flexible space for work, play, or quiet retreat. The land is complete with pastures, a creek, and an antique barn, plus two livestock run-in sheds and a newly constructed 30’ x 50’ metal building with cement floor, and 12’ x 50’ lean-to. Whether you envision a working farm, year-round residence, ski home, or a place to create lasting memories, this property is uniquely positioned. It offers year-round recreation opportunities from your doorstep, just minutes from Lake Whitingham for swimming or boating, Sadawga for fishing, the VAST trail for snowmobiling, and within easy reach of Mount Snow, Stratton, and Berkshire East resorts. Undeniably Vermont!

149 Dix Ln, Whitingham

64 Gleason Farm Ln, Jamaica
$555,000
3 Beds ⋅ 3 Baths ⋅ 5049166 MLS
Nestled on nearly 2 flat acres, this beautifully maintained South-facing New England Cape Cod farmhouse is a rare find in the mountains. Located on a private dead-end road, the home offers peaceful seclusion while being just a short drive to Stratton Mountain for skiing and tubing in the winter and Jamaica State Park for hiking and stunning waterfalls in the warmer months. With only one owner, this like-new property has been meticulously cared for and features high ceilings throughout, creating a bright, airy and open feel. The open-concept living space seamlessly blends the kitchen, dining, and living areas, making it perfect for both relaxation and entertaining. An attached garage offers added convenience, and two charming outbuildings, including a unique Jamaica Cottage Shop potting shed, provide additional character and utility. Enjoy the tranquility of the mountains with easy access to outdoor adventures. This home is ideal for those seeking privacy, comfort, and a seamless connection to nature, offering a truly special living experience year-round.

64 Gleason Farm Ln, Jamaica

155 Pratt Bridge Rd, Jamaica
$550,000
4 Beds ⋅ 3 Baths ⋅ 5094845 MLS
You may wake up to the singing of Cole Pond resident loons at your next VT home awaiting you just minutes from the Stratton Access road. Tucked away on a quiet country road this inviting 4 bedroom, 2.5 bath home offers the perfect balance of comfort, convenience and charm. Designed for gathering with friends and family, entry level offers a family room with woodstove , open concept on main level with attractive fieldstone wood burning fireplace, appealing kitchen with Jenn air stove. Updated baths and pretty wood floors complete this move in residence, set on a nice level lot, the property provides plenty of space for outdoor enjoyment year round. No HOA fees to worry about, just lock and leave at the end of your stay. Don't miss the opportunity to own a well-maintained and appointed escape in a highly desirable area. Schedule your showing today.

155 Pratt Bridge Rd, Jamaica

193 Rt.9 E, Wilmington
$550,000
3 Beds ⋅ 2 Baths ⋅ 5088885 MLS
Step into a piece of Wilmington history with this captivating 3+ bedroom, 2-bath Cape set on a picturesque 1-acre parcel just beyond Wilmington Village. Built in 1920 by Martin Brown, this former “Playhouse” of Beaver Brook Farm (AKA White House of Wilmington) blends timeless character with thoughtful modern updates. The heart of the home is a magnificent open-concept kitchen, living, and dining area, where a brick fireplace creates a warm focal point amid rich hardwood floors, custom built-ins and natural woodwork. Generous windows capture sweeping views of Haystack Mountain and stunning sunsets. The primary suite is a true sanctuary, featuring vaulted ceilings, abundant natural light, a walk-in closet, private exterior access, and a spa-like bath with radiant heat and a sliding barn door. Two additional large bedrooms and a full bath complete the main level. Enjoy the outdoors from the covered front porch or relax on the back deck overlooking a fenced yard with a firepit. Recent improvements include a stylish new kitchen (2023), new drilled well (w/ a new water softener system) and furnace (2025), and fresh interior paint throughout. A custom staircase built by local Ken Frano leads to a loft and office retreat. Close to village amenities, Harriman Reservoir, and Mount Snow. Rental zoning permit in place adds income potential, making this a rare blend of history, character, and charm.

193 Rt.9 E, Wilmington

68 Ellis Brook Rd, Dover
$550,000
3 Beds ⋅ 2 Baths ⋅ 5076580 MLS
Owners willing to consider offers. Gorgeous updated chalet on a private 2-acre parcel with mountain views and easy access to Mount Snow. Nestled in the desirable Dover Hills, this charming country retreat offers privacy befitting a year-round getaway, yet is just a short drive to the Mount Snow ski resort. Ample parking off a paved road, generous lawn space for play or pets, a garden shed, and excellent sun exposure complete the exterior setting. Inside, the updated interior showcases warm woodsy design with a vaulted living room and natural woodwork throughout. Large updated windows provide abundant natural light, complemented by a cozy wood-burning stove. The upscale kitchen features stainless appliances and flows into a spacious dining area and large deck — ideal for entertaining. The main level includes a bedroom and full bath. Upstairs offers a generous guest bedroom and loft sleeping area sharing a full bath with tiled shower and soaking tub. The fully finished lower level provides a family room perfect for overflow sleeping, games, or media space. Functional mudroom entries on both the main and lower levels make four-season living easy, with the lower level leading to a covered porch and outdoor hot tub — the perfect place to relax and take in the scenery. Beautiful furnishings are included for true turnkey enjoyment. Nearby snowmobile trails, hiking, biking, lakes, shopping, dining, and multiple ski options make this an ideal four-season retreat with tremendous rental potential.

68 Ellis Brook Rd, Dover

12 Colonial Ridge Rd, Dover
$550,000
4 Beds ⋅ 3 Baths ⋅ 5073570 MLS
This one won't last long! Beautifully maintained chalet in the Dover Hills, on a 2 acre parcel, just a short drive from the Mount Snow ski resort. The current owners have taken care to keep the original charm of this home while updating consistently to allow for minimal maintenance and easy enjoyment. Off easy paved access, this home sits on a level parcel with ample parking, storage shed, wraparound entertaining deck which leads to the unique tennis court, cand a lovely lawn space without having too much to maintain. Inside you are treated to a gorgeous vaulted great room with rustic woodwork, a wood burning fireplace with stone surround, large kitchen with island and spacious dining area off the convenient mudroom for gear storage, and great natural light throughout thanks to large windows. The main floor has two ample sized bedrooms and a full bath. Upstairs is a large primary suite with shower and soaking tub, which serves as a jack and jill bath for the large fourth bedroom. There is a full finished lower level walkout family room space with ping pong and tv areas, third full bath, bonus bedroom which does not have legal egress sized windows, and a spacious sauna. Recent upgrades include many new windows and sliding door, a new firebox and chimney chase, rebuilt deck, ceiling insulation, and more. Enjoy winter views of the ski slopes out your front windows and easy snowmobile trail access.

12 Colonial Ridge Rd, Dover

39 West St, Newfane
$550,000
3 Beds ⋅ 3 Baths ⋅ 5072039 MLS
This holiday season, immerse yourself in the quintessential charm of Vermont village life at The Tower House, an impeccably maintained 1851 residence in historic Newfane. This distinguished home is instantly recognizable by its welcoming front sitting porch—ideal for watching the world go by—and its most prominent feature: a two-story Queen Anne tower, complete with a pyramidal peaked roof and abundant windows that flood the interior with natural light. Designed for comfort and effortless entertaining, the main level boasts an open-concept kitchen and dining area with a working fireplace, complemented by a second cozy fireplace in the living room—perfect for enjoying throughout the winter months. A spacious first-floor family room with an adjoining bathroom offers practical, age-in-place potential for flexible living. Practical amenities blend seamlessly with modern upgrades. The property includes a convenient two-car garage and a private backyard oasis featuring a serene brook. The current owners have added valuable enhancements, including two Tesla Powerwalls for reliable energy backup, a complete exterior repaint, and professional landscaping and Vego Garden raised beds. The location offers effortless walkability to local landmarks such as the Newfane Inn, Fat Crow Restaurant, and Four Columns Inn. Brattleboro is only a 20-minute drive. Boston is approximately 2.5 hours away, and NYC & Montreal are 3.5 hrs.

39 West St, Newfane

96 Big Bend Loop, Wilmington
$546,000
4 Beds ⋅ 3 Baths ⋅ 5073252 MLS
Stunning updated contemporary chalet just a short drive out of the village of Wilmington with a tremendous rental history. This home sits privately on a wooded lot, nestled in the Chimney Hill community with easy access to the amenities building, as well as nearby access to Mount Snow and Lake Whitingham. The home has been fully renovated and features a gorgeous vaulted living room with exposed beams, great natural light from the large windows, a gas fireplace and stone hearth, contemporary plank flooring throughout, a beautiful chef's kitchen with breakfast bar, stainless appliances, farm sink, and tile backsplash, large dining area, barn door pantry, large mudroom and half bath on the main floor, open concept staircase leading upstairs to 2 spacious bedrooms, a full bath with tiled shower and shiplap paneling, and large owners closet/bonus room, a lower level walkout family room with second fireplace, two large guest bedrooms still with great light, another beautiful paneled bath with tiled shower, full laundry, spacious deck for entertaining, and winter mountain views. Further renovations include indoor and outdoor upgrades to ensure it has a full fire safety permit to be immediately rentable. Featuring the tremendous Chimney Hill amenities including indoor and outdoor pools, remodeled clubhouse with hot tub, gym, game room, theater, basketball court, tennis courts, fishing pond, winter ice skating, overflow parking lots for boats and snowmobile trailers, and direct snowmobile trail access, as well as a la carte maintenance, for easy downtime, not upkeep.

96 Big Bend Loop, Wilmington

217 Magic Cir, Londonderry
$545,925
4 Beds ⋅ 2 Baths ⋅ 5065295 MLS
Just steps from the lift, this is one of the closest single-family homes to Magic Mountain’s base area. Meticulously maintained and thoughtfully updated, it’s a perfect year-round retreat. Upgrades over the years include a newer roof, interior/exterior paint, heat pump with A/C, Wi-Fi thermostats, and a renovated kitchen with modern appliances and an under-bar mini fridge. The open living/dining/kitchen area is ideal for entertaining, complete with a gas fireplace and flat screen TV. Enjoy the screened-in porch that opens to a lower deck - prepped for a hot tub (partially wired) and fire pit area. Upstairs features a primary suite with private bath. Downstairs offers four flexible rooms, full bath, and a den with built-in ski/snowboard storage. Stackable washer/dryer and a newer hot water tank add convenience. Outside includes covered storage for gear and a shed for tools. A transfer switch and propane generator (included) provide backup power. Never rented and used only as a second home, this move-in ready property is close to Black Line Tavern, hiking, and skiing at Bromley, Okemo, and Stratton. Being sold mostly furnished less personal items.

217 Magic Cir, Londonderry

29a Kingswood Rd Unit 29A, Dover
$542,500
4 Beds ⋅ 3 Baths ⋅ 5094878 MLS
Meticulously updated and maintained Kingswood townhome with direct snowmobile trail access and shuttle service to Mount Snow. This uniquely private four-bedroom unit is ideally positioned centrally in the development, offering greater separation between units, great parking, and yet easy clubhouse access. The home features an open-concept living space with vaulted ceilings, a wood-burning fireplace and updated stone hearth, and large windows providing abundant natural light. The kitchen includes a breakfast bar, granite tile counters, stainless appliances, and flows seamlessly into the spacious dining area — ideal for entertaining. The living area leads out to the rebuilt deck for outdoor enjoyment. The main level offers a vaulted primary suite with tiled bath, while the large family room — which can be used as the fourth bedroom — includes a full guest bath. Upstairs are two additional guest bedrooms (one with double bunks), a third full bath, and a convenient laundry closet. A functional dual mudroom entry features tiled flooring, custom cubbies, benches, ski locker storage, covered entry, and wood storage — perfectly designed for mountain living. The home includes thoughtful upgrades such as fresh paint throughout, upscale furnishings and décor, high-end lighting fixtures, added ceiling lighting and fans, and efficient propane heat. Enjoy direct shuttle service from your driveway to the Mount Snow base area. Snowmobile from your yard to the VAST trail system, or access hiking and biking along the Valley Trail in warmer months. Kingswood amenities include an indoor Olympic-size pool, exercise room, game room, clubhouse, wood delivery, trash service, and exterior building maintenance. An ideal option for those seeking downtime — not upkeep.

29a Kingswood Rd Unit 29A, Dover

3333 W River Rd, Dummerston
$540,000
4 Beds ⋅ 3 Baths ⋅ 5097216 MLS
Amazing multi-family residential/commercial opportunity! Tucked back from the road for added privacy, the main home offers 4 bedrooms, 3 baths, and flexible space ideal for first-floor living or a home office. The thoughtfully designed layout features a spacious kitchen with a cozy pellet stove and beautiful cherry dowel flooring, a bright and welcoming dining room highlighted by a lovely bay window, and a generous living room perfect for gathering with family and friends. A private three-season room is a wonderful place to relax or entertain, while the lower level includes a summer kitchen, full bath, and private walkout, offering even more versatility. A second residence provides 2 bedrooms, a full bath, office space, and an attached one-car garage, making it ideal for extended family, guests, potential rental income, or business use. An additional 28' x 40' four-car garage is a fantastic bonus. Occupied by the original owners for the past 46 years, the property showcases beautifully landscaped grounds with mature rhododendrons, a Japanese dogwood, red maple tree and a productive apple tree. Outdoor enthusiasts will love the endless recreational opportunities nearby, including hiking and biking trails, favorite swimming holes, fishing spots, and skiing at Mount Snow, all within a 30-minute drive. This area is also known for some of the most spectacular foliage around and is conveniently located near the popular Indian Love Call swimming spot. Whether you're looking for space for a large family, accommodations for multiple households, private rental possibilities, or room for a home-based business, this unique property offers exceptional flexibility and potential. Please respect the owners’ privacy and do not enter the driveway.

3333 W River Rd, Dummerston

4 Juniors Way Unit B, Dover
$540,000
3 Beds ⋅ 3 Baths ⋅ 5061000 MLS
Fully furnished three-bedroom, three-bathroom townhouse perfectly located less than 2 miles from Mount Snow, offering the ideal mix of comfort, convenience, and fun. The spacious layout features a finished basement, ideal for additional living space, a game room, or accommodating guests. Enjoy modern upgrades including central air, gas fireplace, and an additional mini-split system in the finished basement, new appliances, and stylish furnishings throughout. The first-floor laundry adds everyday ease, while the open layout provides an inviting space for gathering. Outside, a small pond creates a peaceful backdrop while enjoying the back patio, and the carport provides sheltered parking. Low HOA fees add to the appeal, giving you more value and fewer worries. Whether you’re seeking a ski getaway, investment property, or primary home, this townhouse has it all—stylish furnishings, modern updates, and a prime location near outdoor adventure, restaurants, and shops.

4 Juniors Way Unit B, Dover

16 Buckboard Dr, Dover
$540,000
3 Beds ⋅ 2 Baths ⋅ 5058473 MLS
Award-winning, architect-designed home in the Hills of West Dover offers 3 bedrooms, 2 baths located on a beautifully sloped private and secluded 2-acre wooded lot. Originally built for the architect’s own family, the residence blends modern luxury with thoughtful design. The striking facade features painted cedar clapboard, pre-finished corrugated steel, large Anderson windows, and grade level & elevated decked terraces. Inside, radiant-heated acid-stained cement floors, cherry cabinetry, Kohler Plumbing Fixtures, and a sculptural wood staircase set a refined tone. The light-filled layout includes a dramatic 2-story atrium and flexible second-floor rooms ideal for bedrooms, office, or media use. The open plan first floor features a wood burning fireplace with custom kitchen cabinetry & shelving. The house features a new heating system, new standing seam metal roof and new fireplace with chimney flue. Situated on 2 acres, you have the option to retain the second 1-acre lot for added privacy or utilize it as a potential building site. The property is located just minutes off Route 100 and 10 minutes from Mount Snow Ski Mountain. It is a rare opportunity to own a truly unique Dover Hills home.

16 Buckboard Dr, Dover

1041 Church Hollow Rd, Marlboro
$538,000
4 Beds ⋅ 3 Baths ⋅ 5092339 MLS
Country quiet and tranquility! Sun dappled trees and seventeen woodland acres surround this comfortable seven room, four bedroom, two and half bath house and two car garage. A peaceful setting where views from the deck, porch and every window take in the richness of nature and give a feeling of solitude. Built in 1987, this 2567 SF home has been much loved and well cared for. Designed for easy liveablity, a lifestyle choice for two level living now or one level living when desired. An inviting open floor plan with an 18’x 11’ dining room, a 25’ x 15’ living room w/cathedral ceiling, a brick hearth & wood stove, a 12’ x 11’ kitchen that shares the brick hearth wall, all have maple wood floors. A 6’ x 11’ pantry with laundry. The 12’ x 14’ first floor primary bedroom has double closets. The full bathroom has both a separate walk in shower and an adjacent tub with a shower. A 13’ x 14’ bedroom/office and a half bath complete this level. For your creative spirit, upstairs is a 24’ x 13’ loft space now a quilting studio. There is a 22’ x 14’ bedroom with a skylight, large windows and two walk in closets. A cozy 12’ x 13’ bedroom/home office with a skylight. A walk out basement offers ample space for a home workshop. The attached 25’ x 25’ two car garage has storage space above. A pergola covered 20’ x 10’ deck is located off the living room. The 6’ x 25’ side porch is perfect for morning coffee/tea. The 17.8 surveyed acres has 1282 feet of frontage on a town maintained gravel road. When the world invites you away, choices abound in every direction! There is music, restaurants, theater, bookstores, artisan/collectible shops and places for ice cream. Recreational sports of all kinds are not far away. The new Amtrak train station in Brattleboro will bring ways to have new travel adventures. Exit 2 for Interstate 91 is 11 miles away. The town of Marlboro is in the process of completing a townwide property reassessment. Showings begin on Saturday June 6th by appointment.

1041 Church Hollow Rd, Marlboro

49 High Point Dr Unit #A122, Stratton
$537,500
3 Beds ⋅ 3 Baths ⋅ 5029030 MLS
Crown Point, Stratton Vermont. Enjoy this two-level, three bedroom, three bath condo and BONUS "4th" room with direct access to bath. This home has an upper and lower entry, both with plenty of storage for outdoor gear. The upper level opens into the kitchen, dining area, and living room with wood burning fireplace and a small deck. The primary ensuite bedroom, with a jacuzzi tub, is also on the upper level. The lower level has a second living area with wood burning fireplace, two bedrooms, a full bath, and an additional room. For the summer, there is a small pool and BBQ area outside the unit, and there is a shuttle to the resort area for the winter season. Located only a short walk to the Stratton Sport Center, this condo will provide as a perfect base camp for year-round adventures. Stratton Sport Center bond available with buyer paying transfer and Stratton ROFR.

49 High Point Dr Unit #A122, Stratton

67 Heritage Dr, Dover
$535,000
4 Beds ⋅ 2 Baths ⋅ 5104388 MLS
Absolutely charming cedar chalet nestled in the Dover Hills just a short drive from the Mount Snow ski resort. This recently renovated home sits on a private wooded corner lot with winter views of the sunsets and ski trails. Conveniently accessible off a paved road and near the snowmobile trail access. Inside you are treated to a charming open concept living area with vaulted ceiling and exposed timbers, updated luxury vinyl plank flooring throughout, a wood burning fireplace with updated contemporary hearth, large kitchen with breakfast bar and new counters, great natural light from the many windows out to the large deck, a spacious vaulted master suite with updated bath, 3 guest bedrooms and a full guest bath, as well as a bonus overflow or tv room, and a spacious mudroom entry for gear. There is a large new deck for outdoor enjoyment and taking in the views. The home has had egress windows installed and an oversized septic to ensure the home is permitted and ready for tremendous rentability. The home is being sold fully furnished, providing a truly turnkey opportunity for buyers who want to move in and enjoy it or rent it from day one. The natural wood throughout makes this an ideal mountain getaway, so it won't last long!

67 Heritage Dr, Dover

238 Hemlock Hill Rd, Wardsboro
$535,000
5 Beds ⋅ 2 Baths ⋅ 5042003 MLS
This spacious 5 bedroom home is located on a private lot in the popular Snow Mountain Farms community. The Property has a brand new roof!!! The three levels offer privacy and quiet with an outdoor fire pit, garden shed, and access to the VAST snowmobile trails across the street. Its open floor plan with vaulted ceilings and stone hearth gas fireplace is perfect for aprés ski gatherings, and the large open kitchen is ready to accommodate cooking for a large group. Just off the kitchen is a dining room with views over the wooded lot with convenient access to the screened porch for summer entertaining.The property includes all furnishings, A Tesla Battery Back up system as well as an electric car charger.The property has a new roof installed 4/12/26 The Snow Mountain Farms clubhouse features an indoor pool, plus outdoor tennis and pickle ball courts. Make an appointment today to tour this special property located 15 minutes to Mount Snow and 20 minutes to Stratton Mountain.

238 Hemlock Hill Rd, Wardsboro

121 Dover Hill Rd, Dover
$535,000
3 Beds ⋅ 2 Baths ⋅ 5031010 MLS
Highly motivated sellers. Ideal for remote workers or second-home buyers, this Vermont retreat offers fiber-optic internet, energy-efficient systems, no water or sewer bills, and some of the state's lowest property taxes. Set on 5 private acres just minutes from Mount Snow and Grout Pond, this move-in ready home supports low-cost living with high quality of life. The updated kitchen features new appliances, a butcher-block island, and bold blue tiles. Inside, vaulted ceilings, hardwood floors, and a wood-burning fireplace provide warmth and charm. A sun-filled four-season porch offers peaceful views and year-round comfort. Outdoors, you will find a barn with paddocks, a sugarhouse, and established raspberry and asparagus gardens. It is an excellent fit for homesteaders, hobby farmers, horse owners, or anyone seeking space and privacy. With school choice for grades 7 through 12 and short-term rental potential, it also appeals to investors and growing families. Whether you are downsizing, purchasing your first home, or looking for a seasonal escape, this versatile property is ready for its next chapter. Schedule your private showing today.

121 Dover Hill Rd, Dover

72a Kingswood Rd Unit 72A, Dover
$531,000
4 Beds ⋅ 3 Baths ⋅ 5076153 MLS
Meticulously updated and maintained Kingswood townhome with direct snowmobile trail access and shuttle service to Mount Snow. This uniquely private four-bedroom unit is ideally positioned on the lower side of the development, offering greater separation between units, easy trail access, and a more usable private rear yard. The home features an open-concept living space with vaulted ceilings, a wood-burning fireplace, and large windows providing abundant natural light. The kitchen includes a breakfast bar, granite tile counters, stainless appliances, and flows seamlessly into the spacious dining area — ideal for entertaining. The main level offers a vaulted primary suite, while the large family room — currently serving as the fourth bedroom — includes a full guest bath. Upstairs are two additional guest bedrooms (one with a twin-over-full bunk), a third full bath, and a convenient laundry closet. A functional dual mudroom entry features tiled flooring, custom cubbies, benches, ski locker storage, covered entry, and wood storage — perfectly designed for mountain living. Step outside to a large updated deck with pet-friendly gate, private rear yard, and more parking than many earlier Kingswood units. Offered truly turnkey for immediate enjoyment, the home includes thoughtful upgrades such as fresh paint throughout, upscale furnishings and décor, high-end lighting fixtures, added ceiling lighting, and efficient propane heat. Enjoy direct shuttle service from your driveway to the Mount Snow base area. Snowmobile from your yard to the VAST trail system, or access hiking and biking along the Valley Trail in warmer months. Kingswood amenities include an indoor Olympic-size pool, exercise room, game room, clubhouse, wood delivery, trash service, and exterior building maintenance. An ideal option for those seeking downtime — not upkeep.

72a Kingswood Rd Unit 72A, Dover

4138 W Hill Rd S, Jamaica
$530,000
3 Beds ⋅ 3 Baths ⋅ 5077783 MLS
Nestled on 2.37 private acres in a serene mountain setting just minutes from skiing, this custom-built three-bedroom, three-bath log home offers the perfect blend of rustic charm and comfort. Constructed with double tongue-and-groove logs, the home showcases the rich wood interior and craftsmanship you would expect in a classic mountain retreat. The open-concept main level centers around a stunning fieldstone hearth and cozy wood stove, complemented by beautiful oak flooring throughout. A covered front porch overlooks the peaceful wooded landscape, while the back deck enjoys long hours of sunshine—ideal for relaxing or entertaining. The main level includes a spacious primary bedroom with an ensuite bath, a bunk room, an additional full bathroom, and a versatile bonus room perfect for a den, home office, or extra sleeping space. Downstairs, the walkout lower level features a generous mudroom designed for all your outdoor gear, a large bedroom, a full bathroom, and another flexible bonus room ideal for recreation or entertaining. Set well back from a quiet country road yet conveniently located near the quaint village of Jamaica, the property is accented by classic stone walls and gladed woods, enhancing its Vermont charm. A two-car garage, storage shed for recreational equipment, and a timber shed complete this exceptional offering. Whether you're seeking a full-time residence or a mountain getaway, this inviting log home delivers privacy, character, and convenience in one beautiful package.

4138 W Hill Rd S, Jamaica

25-27 Gingko Ln, Brattleboro
$528,000
5091758 MLS
Great income producing properties! Rent out the 2 apartments over the garage while you live in the adorable 2-story home. Or, finish the house renovations and rent all 3. Located on a quiet side street in this beloved neighborhood, you are in close proximity to the Retreat trails, which offer extensive hiking, and close to our vibrant downtown, a short walk away. The adorable 1,600-square-foot home has 3 bedrooms and 2 baths. The light-filled, open-concept kitchen/dining area is inviting and spacious. Upstairs needs finishing, but there are vaulted ceilings and an abundance of light from the many skylights. Pretty stone paths, widespread gardens, open decks, and a level, private sunny lawn. Above the two-car garage are two rental units—one occupied and one vacant—offering immediate income, strong potential for investors, and appreciation for homeowners. One unit is a two-bedroom, one-bath, and the other is a one-bedroom, one-bath. The home needs some finishing work, but this is an unbeatable opportunity, and your work will be well worth it. *The income/expenses are only for the 2 garage apartments.

25-27 Gingko Ln, Brattleboro

7 High Top Rd Unit B-117 & B-118, Wilmington
$525,000
3 Beds ⋅ 2 Baths ⋅ 5100963 MLS
Section B. Top of the Hill, end of the road, this home is meticulously kept and updated, with lots of attention to detail. Start living the dream you imagine! A classic chalet design with mudroom entry, full bath and bedroom, and open concept living, dining and kitchen on the main level, with a wraparound deck. Upstairs has two bedrooms and a second full bath. The double lot offers privacy and options for a garage. Nice, landscaped level lot with a shed and woodbin, firepit and plenty of parking. Enjoy all the amenities Chimney Hill offers including the exclusive members only clubhouse, located at 2,000' in elevation, it's the perfect spot to enjoy year-round featuring indoor and outdoor heated pools, a brand new hot tub, fitness room, arcade, playroom, lounge, fully-equipped kitchen, playground, community room, table tennis, pickleball, ice skating, hiking, biking and snowmobiling on the 1,200 acre resort campus nestled between the Green Mt National Forest and the town of Wilmington VT. Minutes from world class skiing and shredding at either Vail's Mt Snow or the private Hermitage Club. Discover Southern VT and enjoy outdoor and indoor music, festivals, unique shopping and dining, antiques, flea markets, golf, boating, paddleboarding, and so much more! Owner's list of features and improvements: Two Mini-Split Units for AC/Heat, Replaced all Electric Baseboard Heating Units, Gasoline powered generator hardwired into the electric panel, New Electric Panel, Hardwired Ring Outdoor Cameras, Vapor Barrier Throughout Crawl Space, Flooring throughout the whole house, Window treatments, Furniture, Bedding, Kitchen Appliances, HWH on GMP Rental Program $10 mo., Washer & Dryer, Four Flatscreen TV’s, Safe in MBR, Kitchen Countertops, Both Bathroom Fixtures, Countertops & Toilets, Ceiling Fans & Ceiling Lights, Safety Railings & Wiring on Stairs & Loft, Storage/Woodshed Outside, Firepit.

7 High Top Rd Unit B-117 & B-118, Wilmington

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