Bennington County

MLS Number 5085047

• Residential Single Family
• Full Bath 3
• Address 751 Main Road
• Bedrooms 6
• Bathroom 6

Step into the most amazing Victorian house you will ever see! Built in 1880, you will feel like you've walked back in time. Beautiful architecture and woodwork. The house was built by John Tudor, a Welsh immigrant who had made a fortune as a mill owner in northern Vermont and settled in Stamford. There is a stunning 3 floor Post & Beam Barn built in 2000 with a 2 car garage built-in. Barn also features 4 stalls with room for a 5th, tack room, hayloft, along with some finished sq ft with electric, heat and water. Also included is a 2nd home on the property. It's a 2 bedroom 870 sq ft 1 story Modular. Other amenities include a very large in ground salt water pool with new liner along with a beautiful pool house with outdoor kitchen and bathroom, sauna, green houses, shed and a tiny vineyard with 50 vines! Two duck houses and a small 10 x 8 cow barn. Oh, I almost forgot the chicken coop! 400 amp Whole House Generator. 2 septics and 2 drilled wells. Located on the southern border of Vermont with mountain views of Mt Greylock in the Berkshire Mountains. Just under 10 acres of level land with fruit trees. 2 Stone Lions in the front yard have been a marque in the village for years. This property has so much to offer in a small southern Vermont town!

Listed by Michael Jarvis of United Country Real Estate Mike Jarvis Group Inc

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

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MLS Number 5090426

• Residential Single Family
• Full Bath 3
• Bedrooms 4
• Bathroom 3
• Square Feet 3,370

Perched on the side of Mount Aeolus and conveniently located near Manchester, this exceptional 4-bedroom, 3-bath contemporary retreat offers privacy, sophistication, and year-round natural beauty across 21 picturesque acres. Thoughtfully designed to embrace its surroundings, the property features rolling meadows, mature woodland, vibrant perennial gardens, and sweeping views of the Green Mountains from every room. A striking exterior with modern architectural lines, standing seam roofing, marble accents, and expansive glass entryways sets the tone upon arrival. Inside, an airy open-concept layout is flooded with natural light through oversized windows that frame the mountain landscape like artwork. Ideal for entertaining, the home offers multiple inviting gathering spaces from the elegant living and dining area with rich cherry floors and a fireplace, to the expansive great room complete with a sun-filled solarium, wood stove lounge, wet bar, and chef-inspired kitchen featuring stainless steel appliances and generous wraparound cabinetry. Radiant heated slate floors warm the oversized family room, while the main level also includes a serene primary suite, spacious mudroom, and a flexible bonus room suited for a studio, office, or fitness space. Step outside to two oversized decks with electric awnings or unwind in the marble-surrounded hot tub beneath the stars. The lower-level optimizes a geothermal design and hosts three bright guest bedrooms, including one with its own fireplace and covered deck access, along with two additional baths and a laundry room. A survey is available identifying potential opportunities for subdivision or additional building sites, offering flexibility for future expansion, investment, or multi-generational living. Blending refined modern living with the tranquility of Vermont's landscape, this one-of-a-kind property is a rare mountain sanctuary designed for comfort, connection, and escape.

Listed by Annette Gallo and Stephanie Sugden of Real Broker LLC

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 1310 Dorset Hill Road Dorset VT 05253 (#5090426).

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MLS Number 5078597

• Residential Single Family
• Full Bath 1
• Address 2167 Myers Road
• Bedrooms 3
• Bathroom 3

Welcome to Hidden Ponds Farm - a breathtaking retreat set on 40 sprawling acres where history and refined country living meet in perfect harmony. This extraordinary early 1800s post-and-beam converted barn has been thoughtfully reimagined, preserving its authentic character while seamlessly integrating modern comforts. A magnificent 1,000-foot hand-placed stone wall winds gracefully across the landscape, framing two picturesque ponds and twin orchards that offer seasonal beauty and fresh harvests. The outdoor amenities elevate this property into a private resort: an inviting in-ground pool, hot tub, propane fire pit, and an impressive 90-foot deck with retractable awning, ideal for effortless entertaining and long summer evenings under the Vermont sky. For collectors, hobbyists, or outdoor enthusiasts, the property offers exceptional versatility. A detached four-bay garage with second-story loft provides abundant storage, while an additional outbuilding easily accommodates a large Class A motor home or boat. Separate pump houses serve both the pond and pool, ensuring functionality meets convenience. A dramatic post-and-beam great room addition, completed in 1997, creates a striking focal point within the home. Anchored by a soaring floor-to-ceiling stone fireplace, this grand yet welcoming space captures the essence of rustic elegance. Above, a charming loft offers the perfect reading nook, studio, or private office retreat. The renovated kitchen blends contemporary appliances and thoughtful design with the warmth and character of the original barn structure. Three spacious bedrooms and three beautifully updated bathrooms, including one featuring a luxurious steam shower, provide comfort and privacy for family and guests. Hidden Ponds Farm is a rare and remarkable offering, a timeless estate where history, natural beauty, and modern living come together in one unforgettable property.

Listed by Kelley McCarthy of Mahar McCarthy Real Estate

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

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MLS Number 5086670

• Residential Single Family
• Full Bath 5
• Address 144 Taconic Road
• Bedrooms 6
• Bathroom 6

“The Colonial” - Queen of Taconic Avenue One of the original summer “cottages” gracing historic Taconic Avenue, The Colonial is a crown jewel of Manchester Village. Painstakingly renovated, this stately home perfectly balances old-world charm with modern sophistication. The heart of the home is a stunning new chef's kitchen, seamlessly blending timeless design with today's comforts. All-new windows, updated electrical and plumbing, and thoughtful improvements throughout breathe new life into this historic residence while preserving its character and grace. The first floor offers multiple inviting sitting areas, a formal dining room ideal for gatherings, and elegant spaces for entertaining. Upstairs, the second floor features four beautifully appointed bedrooms and three fully renovated bathrooms, including twin en-suites. The master suite is highlighted by a spa-inspired bath, complete with a soaking tub overlooking the majestic slopes of Mount Equinox. A versatile third floor offers additional guest rooms or flexible living space. Outdoors, the wraparound porch-often called the finest sitting porch in Manchester Village-sets the stage for warm summer evenings, conversation, and al fresco dining. A detached carriage house provides further opportunity as a private in-law apartment or a spacious work-from-home retreat. Steeped in history yet fully renewed for modern living, The Colonial is a true gem in the heart of Manchester Village. Homes of this caliber rarely come to

Listed by Sara Buckley and Thomas Deck of Josiah Allen Real Estate, Inc.

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

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MLS Number 5064340

• Residential Single Family
• Full Bath 1
• Bedrooms 6
• Bathroom 3
• Square Feet 3,340

Two homes, multiple barns and outbuildings on 60 +/- incredible acres in Dorset, VT. Nestled in the Green Mountains, 215 Route 30 the 1780s farmhouse featuring 3 bedrooms, 2 baths with 1645 finished sqft. The second building, nestled away from the road is 221 Route 30 built in 1940 with 3 bedrooms and 2 baths. 1800 sqft. The property offers pastoral venues, mature forest, and scenic mountain views. Stone walls border the south edge of the property. The extraordinary 60-acre estate parcel in Dorset, perfectly positioned along Route 30. This remarkable property offers the ultimate trifecta-location, natural beauty, and limitless potential. Featuring a mix of rolling meadows and scenic mountain logging trails, this raw, untouched farmland is a rare find in one of Vermont's most sought-after areas. Held in the same family for generations, the property is ready for new owners to bring their vision to life. The open fields invite cattle to graze, gardens to flourish, and dreams to take shape. With three convenient access points off Route 30 and an unrestricted deed, the possibilities are endless-whether you envision a private country estate, a residential subdivision, or even a condominium development. The property straddles Manchester/Dorset, known for its historic village charm, quaint shops, and outdoor recreation. The area offers privacy and easy access to Manchester, making it ideal for both full-time living and weekend escapes.

Listed by Margretta Fischer of Wohler Realty Group

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

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MLS Number 5073964

• Residential Single Family
• Full Bath 2
• Bedrooms 3
• Bathroom 3
• Square Feet 3,368

Luxury Timber Frame Estate on 52+ Acres in Southern Vermont. This exceptional custom post-and-beam retreat is privately set amid rolling hardwood forestland, offering expansive mountain views, remarkable privacy, and a rare sense of peace and connection to nature. Designed for both elegance and efficiency, the home features solar panels with two Tesla Powerwalls for optional off-grid independence, paired with energy-efficient mini-split systems providing low-cost heating and air conditioning throughout the seasons. The residence offers three bedrooms and three baths, two versatile lofts, bonus room, gym and a spacious attached two-car heated and insulated garage, complemented by a flexible office, studio, or guest space above-perfect for today's work-from-home lifestyle, supported by high-speed internet in a truly serene setting. A newly designed chef's kitchen with premium appliances flows effortlessly into refined living spaces anchored by a Vermont stone fireplace, blending warmth, craftsmanship, and timeless Vermont character. Outdoor living is equally impressive, featuring a bluestone patio, in-ground heated pool with integrated hot tub, all surrounded by sweeping 360-degree mountain vistas and complete privacy-an idyllic environment for both entertaining and quiet retreat. The expansive acreage includes a separately deeded 10.53± acre parcel located at the intersection of Wilcox Hollow Road and Sandgate Road, featuring approximately 25 apple trees and a tranquil softwood stand, presenting the perfect opportunity for a second family residence or guest home. Ideally located near Manchester fine dinning and shopping while enjoying the benefit of affordable Sandgate taxes, the town offers full school choice from Pre-K through 12th grade. Four Vermont Ski resorts are within one hour, and both New York City and Boston are just three hours away. A rare Southern Vermont offering where privacy, community, and breathtaking mountain vistas exist in perfect harmony.

Listed by Margretta Fischer of Wohler Realty Group

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

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MLS Number 5081618

• Residential Single Family
• Full Bath 1
• Address 397 Fern Hill
• Bedrooms 5
• Bathroom 5

Take a drive up Nichols Hill Road to Fern Hill and head to the very top of the long bending driveway to find a serene, picturesque artist's retreat 3 minutes from historic Dorset Village. Refreshingly private, quiet and secluded, drenched in natural light. With broad mountain vistas of Mother Myrick and Merck Forest, the top of the property backs gently into a beautiful private forest. The entire property has been carefully curated to encourage wildlife, a rewilding effort in place for 9 years, toxin and poison free. The large, pristine, spring fed swimming pond is the year round home to approximately 50+ healthy colorful Koi and overlooks a soft meadow bordered by old growth forest habitat, much to the delight of birds, butterflies, dragonflies, bees and abundant wildlife. The house is large, eclectic and rustic with a lodge feeling. A simple open concept design with lots of room and a farmhouse kitchen. Abundant windows throughout invite in and embrace the changing light and glistening view all day long. Distressed wide-plank floors, repurposed barn wood walls and beams, natural wood tray ceilings, curving wooden bookshelves and a curving staircase that leads to a half moon studio filled with natural light and sweeping views. Off the farmhouse kitchen find the very substantial screen porch and long sitting porch overlooking the gorgeous, vibrant, spring fed pond which reflects the changing light and soft scenery all day long. Natural beauty and peace, completely private and yet so close to everything.

Listed by Laura Beckwith and Elizabeth Romano of Josiah Allen Real Estate, Inc.

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

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MLS Number 5089425

• Residential Single Family
• Full Bath 2
• Address 527 Sleighbell Lane
• Bedrooms 4
• Bathroom 6

Set on over 11.5 private acres, this custom-built Colonial offers the kind of comfort, craftsmanship, and peace of mind that's increasingly hard to find. Thoughtfully designed and maintained since it was built in 2004, this home blends timeless style with practical features for everyday living. With over 4,300 square feet, the layout provides generous space without feeling overwhelming. The home is permitted for four bedrooms, with flexibility for additional rooms to accommodate guests, hobbies, or a home office. Five full bathrooms and a half bath ensure convenience for both residents and visitors. The main level is designed for ease and accessibility, featuring a spacious primary suite with a spa-like bathroom, complete with a soaking tub. A two-story great room with a striking floor-to-ceiling stone fireplace creates a welcoming gathering space, while hardwood floors and central air conditioning add comfort throughout. The kitchen is equipped with high-quality Viking appliances, ideal for those who enjoy cooking and entertaining. Outside, the property has been thoughtfully improved to enhance mountain views and to maximize natural light. Additional features include a heated two-car garage, a large laundry room, ample storage space, and a finished lower level with a recreation or fitness area that opens directly to a bluestone patio. An elevated screened porch offers a quiet place to relax and enjoy the surrounding landscape.

Listed by David Halligan of Four Seasons Sotheby's Int'l Realty

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

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MLS Number 5077038

• Residential Single Family
• Full Bath 4
• Address 1035 Holy Smoke Road
• Bedrooms 5
• Bathroom 5

Experience the quintessential Vermont lifestyle in this masterfully renovated (2021) contemporary farmhouse, offering 6,100 sq. ft. of finished living space. Tucked at the end of a breathtaking maple-lined driveway, this 17± acre property offers panoramic mountain views and a private sanctuary for hiking, cross-country skiing, snowshoeing, and snowmobiling right from your door. The heart of the home features beautiful cherry flooring and a chef's kitchen with premium appliances and quartz countertops, flowing seamlessly into a spacious dining area with an intimate sitting room anchored by a soapstone stove. Beyond, a window-lined living room with vaulted wood-beamed ceilings and custom built-ins serves as a perfect hub for media, games, or relaxation. The top floor is designed for both luxury and versatility, featuring a primary suite retreat with a private fireplace and a modern en suite bath showcasing those incredible mountain views. A window-lined hallway with recessed laundry leads to a flexible secondary living wing with two additional vaulted ceiling bedrooms and two full bathrooms-perfectly suited for guests or an au pair suite with its own separate entries. The expansive lower level is built for indoor-outdoor living, featuring a massive stone fireplace, family room, exercise area, game room, and two private bedrooms. Large glass doors provide a seamless walk-out to the patio, where you'll find a heated inground swimming pool and a custom fire pit. Automotive and outdoor enthusiasts will appreciate the three separate garages accommodating several cars plus a spacious workshop, including one bay designed specifically for a boat or oversized vehicle. A solar array on the garage roof works with backup batteries to keep electric costs below $400 annually. Located with easy access to Stratton and Mount Snow, and a straightforward drive from New York or Boston, this estate is the ultimate four-season destination.

Listed by Lori Hurley of Four Corner Properties LLC

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

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