Windham County

MLS Number 5026310

• Residential Single Family
• Full Bath 4
• Address 43 Upton Road
• Bedrooms 6
• Bathroom 5

The best of both worlds... High end luxury in this Post & Beam home on a private 35+ acre wooded lot with direct ski trail views of Mount Snow, yet just over a mile to the ski area. It's nearly impossible to find this kind of privacy so near mountain. This spectacular 6 bedroom, 4.5 bath Post & Beam home was built in 2007 and no expense was spared in the construction. Features include a high end chef's kitchen with granite counters, stainless appliances, breakfast bar, pantry, stunning 3 story vaulted great room with stone fireplace that also offsets heating costs, natural wood joinery and exposed beams throughout, beautiful hardwood floors, a large screened-in porch and entertaining deck for 3 season enjoyment, a primary suite on the main level with tiled shower and jacuzzi tub, 3 upstairs guest bedrooms with full bath, spacious loft, and bonus third floor loft room, a full finished basement with family room and full guest suite, as well as ample owner storage, additional guest suite above the garage, and stunning mountain views from almost every room. There is an attached 2 car garage which leads into the oversized mudroom with cubbies for all your gear, hot tub, and numerous recent upgrades including new roof, new paved driveway, all new paint, lighting, wifi thermostats, cameras, and energy monitoring, and furnishings, which are included at the offering price. Direct access to VAST snowmobile trails. Septic sized for 4 bedrooms full time use.

Listed by Adam Palmiter of Berkley & Veller Greenwood/Dover

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

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MLS Number 5088735

• Residential Single Family
• Full Bath 3
• Address 74 N Brookwood Road
• Bedrooms 4
• Bathroom 3

PRIME LOCATION near the coveted STRATTON MOUNTAIN RESORT. This EXCEPTIONAL four bedroom three bathroom turn-key home is PRIVATELY SITUATED on 1.5 acres and READY TO BE ENJOYED YEAR ROUND. Snowmobile right from the house to access thousands of acres of pristine VAST snowmobile trails for ENDLESS WINTER ADVENTURE. Ski home to the Covered Bridge neighborhood or hop on the resort shuttle, which runs every weekend and picks up right at the end of the driveway for an EFFORTLESS TRIP TO AND FROM THE MOUNTAIN. This property also coveys with the coveted Stratton Mountain and Fitness bond, granting FULL ACCESS to the golf course, fitness center, and an EXCLUSIVE PRIVATE HOMEOWNERS LODGE AT THE MOUNTAIN. The spacious great room features CATHEDRAL CEILINGS, walls of glass and a DRAMATIC WOOD BURNING FIREPLACE. The GOURMET KITCHEN with stone countertops and UPSCALE APPLIANCES opens seamlessly to the dining and great room. The primary suite offers privacy with a BEAUTIFUL BATH, walk in closets and WOODLAND VIEWS. A family room with SUNNY EXPOSURE opens to the back deck where you can ENJOY THE SPA. Multiple decks provide both covered and open spaces to enjoy the seasons, including a beautiful front upper deck that offers AMAZING SUNRISE AND SUNSET VIEWS. Wood floors, tile baths, and a lovely entry and mudroom complete the interior. IDEAL FOR WINTER AND SUMMER ENTHUSIASTS seeking a premier resort.

Listed by Paul Marino of WWW.FLATFEEMLS4FREE.COM

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

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MLS Number 5089005

• Residential Single Family
• Full Bath 4
• Address 3 Slopeside Road
• Bedrooms 6
• Bathroom 6

Trailside luxury in a class of its own. This stunning home was taken down to the frame and should be considered new construction positioned immediately trailside at Mount Snow with a private ski trail connecting directly to the magic carpet at Carinthia for full-season ski access. Ski to and from your mudroom door and never worry about shuttles or parking again. Professionally designed and built with no expense spared, the home welcomes you with a generous mudroom outfitted with benches and hooks for all your gear, conveniently off the oversized garage, ideal for gear storage. The main living level showcases a vaulted great room with exposed natural wood ceilings and beams, a floor-to-ceiling stone chimney with wood-burning fireplace, and expansive new windows that frame breathtaking mountain proximity and flood the space with natural light. The chef's kitchen features stainless appliances, contemporary cabinetry, custom counters, and a substantial island, open to the large the dining area. Down the hall, a half bath with handsome brick floors, a walk-in pantry that can double as an owner's closet, and a dedicated laundry room add everyday functionality. An office with a murphy bed offers flexible guest space, alongside a generous guest bedroom and a full bath with tiled shower. The upper level is home to a spectacular primary suite with a spa-like bath featuring exquisite custom tilework, plus two additional guest bedrooms and a full guest bath. The entry level delivers an expansive family room perfect for entertaining, complete with a half bath, wet bar, a bunk room with its own full bath, and a slider which leads out to the hot tub and fire pit. A spacious deck rounds out the outdoor living, ideal for grilling and soaking in the aprs-ski sun. With easy access off a paved road and ski-in/ski-out proximity that simply cannot be found anywhere else, this is a rare opportunity that will not last.

Listed by Adam Palmiter of Berkley & Veller Greenwood/Dover

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

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MLS Number 5087347

• Residential Single Family
• Full Bath 2
• Address 95 Middletown Road
• Village So. Londonderry
• Bedrooms 4

One-of-a-Kind Vermont Lifestyle Property Home, Income & Creative Opportunity Welcome to an exceptional Southern Vermont offering that blends refined country living with rare income and lifestyle flexibility. Set on 2.4 picturesque acres in South Londonderry, this beautifully restored 1865 property is first and foremost a warm and inviting 4-bedroom home-rich in character, thoughtfully updated, and designed for everyday living. Originally an inn and lovingly reimagined by its current owners, the residence offers comfortable living spaces alongside multiple options for creative use, hosting, or generating income. A separate rental ADU, classic Vermont barn, greenhouse, and expansive grounds bordered by historic stone walls create a setting that feels both private and full of possibility. Adding to the property's versatility is the space currently home to the nationally recognized SoLo Farm & Table-an award-winning farm-to-table restaurant with a loyal following. Fully equipped with a state-of-the-art kitchen, wood-fired masonry grill, sound-insulated dining rooms, and curated wine display, this space is ideal for a turnkey culinary venture-or could be reimagined as a studio, event venue, workshop, or expanded residential use. Outdoor living is equally compelling, featuring a beautifully designed stone patio with a custom-built whole animal cooker, a hard-wired generator, established growing spaces, and room to gather, create, and unwind. Whether you envision continuing a celebrated culinary destination, cultivating a home-based business, or simply enjoying a distinctive Vermont property with room to grow, this offering presents a rare opportunity to live, work, and thrive in one remarkable setting.

Listed by Eric Nathan of Nathan Auction & Real Estate Inc.

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

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MLS Number 5072561

• Residential Single Family
• Full Bath 3
• Bedrooms 4
• Bathroom 3
• Square Feet 2,420

This vintage renovated waterfront home is being offered for the second time in 40 years. Lake Raponda allows motorized craft, with primarily private beach front, and a small local boat launch and public beach. It is located conveniently down from the Mt Snow Ski Resort, on a quiet road, affording year round enjoyment and solitude. This home has been lovingly maintained, updated, and expanded by the current owners, and features a lodge style quite unique in the area which offers warm charm and Vermont rustic styling perfect for a retreat. Inside you are treated to vaulted ceilings in the main living room with floor to ceiling stone fireplace. There are freshly painted walls and exposed woodwork throughout, a country kitchen with gas stove and basin vintage sink, great light from the many windows and updated lighting, a tremendous great room addition perfect for entertaining with wood stove for ambiance, two main floor suites including a large primary, an upstairs guest suite, a spacious sleeping loft, great storage and closet spaces, a den/tv room ideal as an office or overflow sleeping, and lake views from every bedroom. Outside you'll find a large stone patio with hot tub which leads down to the extensive perennial landscaping and path to the water. There is a boathouse at the lake for lake storage, a large dock, swim platform, and level lawn space for fun in the sun. The home has a detached garage great for off season boat storage or whatever you may need. Updated septic!

Listed by Adam Palmiter of Berkley & Veller Greenwood/Dover

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

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MLS Number 5092566

• Residential Single Family
• Full Bath 1
• Address 161 Depot Road
• Bedrooms 4
• Bathroom 4

Perched high above the enchanting hills of Newfane, VT, lies a truly one-of-a-kind property. This meticulously crafted home offers an off-grid, private retreat with breathtaking views of the surrounding landscape. Constructed in 2003, the post and beam design incorporates wood and stone harvested from its expansive 219-acre setting, showcasing a harmonious blend of nature and architecture. This exceptional estate is now ready to welcome its next owners. Designed with sustainability in mind, this eco-friendly property features numerous green initiatives such as locally sourced materials and renewable energy sources. Thoughtful land management practices further enhance the property's environmental stewardship, making it a sanctuary that harmonizes with its natural surroundings. As you ascend the driveway, you pass grain bins, barns, and pastures, remnants of a once-thriving goat farm. Midway up the drive, near the old foundation of the original homesite, you will discover a serene swimming pond complete with a cabana and a wood-fired sauna, providing a tranquil oasis. Upon reaching the summit, you are greeted by sweeping 180-degree views of the verdant hills. Stone walkways wind through perennial gardens surrounding the house, leading to a wood-fired hot tub and sun deck where you can immerse yourself in the stunning scenery. Meandering trails, A guest house above the 2 car garage, and an expertly crafted treehouse round out this remarkable property. Schedule today.

Listed by Keith Nowak 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 5077331

• Residential Single Family
• Full Bath 4
• Address 4669 Vermont Rte 100
• Bedrooms 7
• Bathroom 5

Encompassing over 200 acres of pasture and forest, Timberland Farm is anchored by an early 1800s farmhouse that feels at once timeless and lived-in, a place shaped by centuries of stories, music, and shared meals. The living spaces feel both intimate and generous, framed by hand-hewn beams and original wide pine floors. From the dining room to the music room, wood-burning fireplaces crowned with antique mantels add warmth and character, while the expansive kitchen hearth draws one in for easy conversation and board games. Built-in bookcases, plaster walls, wood paneling, and windows overlooking the land lend the house a quiet, grounded grace. The farmhouse also includes a lower-level guest apartment with a private entrance. Nearby, a charming guest cabin, once the town's blacksmith shop, provides a private haven for visitors. The barn has been thoughtfully reimagined and now houses a commercial kitchen, gym, and offices, offering flexibility for creative enterprise and agricultural ventures. A separate barn includes a woodworking shop. In recent years, pastureland surrounding the home and pond was reclaimed for grazing goats, restoring the agrarian rhythm of the property. Wildflowers and apple trees scatter the fields. A three-quarter-mile hike through the wood reveals a cool swimming hole. Additional woodland trails invite walking, snowshoeing, and foraging for berries, mushrooms and fiddleheads. Timberland Farm is a legacy holding, and very private, yet within easy reach of Stratton, Bromley, Magic Mtn. and Okemo. 17 miles from Manchester and 26 miles from Rutland Airport. 3 h from Boston and 4 h from New York. No showings through May 16th, 2026. Showings are by APPOINTMENT ONLY. Do not drive up the driveway to view the property. Home is owner-occupied and surveillance is in effect.

Listed by T Story Jenks and Dia Jenks of LandVest, Inc/Woodstock

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

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MLS Number 5091196

• Residential Single Family
• Full Bath 3
• Bedrooms 7
• Bathroom 6
• Square Feet 6,292

The Hickory Ridge House is a Federal Masterpiece. Own a definitive piece of Vermont history with this 1808 Federal-style estate, proudly listed on the National Register of Historic Places. For decades, it was a B&B. It could still be used as a very upscale, sophisticated country Inn. While its soul remains rooted in the 19th century, its heart beats with 21st-century innovation. This meticulously restored residence features a newer roof, solar panels, and a Tesla Powerwall, offering a level of energy independence rarely found in historic homes. The interiors are a masterclass in "refined rustic" design. Five spacious bedrooms are anchored by a chef's kitchen where rough-hewn textures meet polished, modern finishes. Outside, the lush grounds are a perennial paradise of fruit trees and colorful flowers. For those seeking the ultimate family compound, a charming two-bedroom cottage is on the premises. Located just moments from one of the most vibrant villages in Vermont, with world-class performances at Yellow Barn and the legendary pies of Green Mountain Orchards, this isn't just a home-it's a front-row seat to the best of Putney. More photos of the Cottage and a full prospectus are available upon request.

Listed by Thom Dahlin of Berkley & Veller Greenwood Country

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 53 Hickory Ridge Road South Putney VT 05346 (#5091196).

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MLS Number 5073006

• Residential Single Family
• Full Bath 4
• Address 286 Coldbrook Road
• Bedrooms 4
• Bathroom 5

This new construction home is in one of Southern Vermont's top four season destinations. Three homes are being built, with two still available, offering a great opportunity to secure a brand new home! The multi gabled modern farmhouse design blends clean architectural lines and warm natural materials. Ideally located just minutes from Mount Snow, the Hermitage Club, Harriman Reservoir, golf courses, and local amenities, this home suits a luxury second home, a strong investment property, or a comfortable year-round residence. The floor plan features a main level primary bedroom with an en suite bath and walk-in closet, plus what could be a second primary bedroom on the lower level with a full bath and direct walkout access to the covered patio. There are two more spacious bedrooms on the top level, each with its own full bathroom, and a bonus room for an office or extra sleeping space. Highlights include a two-story great room with a wood burning fireplace, a large covered porch, and an oversized attached two car garage. Buyers who commit early could personalize finishes within the builder's allowances or choose upgrades at their expense.

Listed by Melissa Nebelski 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 286 Coldbrook Road Wilmington VT 05363 (#5073006).

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