Very Cool Houses

MLS Number 5081997

• Residential Single Family
• PricePerSqFt 427.54
• Full Bath 4
• Construction Existing
• Bedrooms 5

Welcome to Green Peak Orchard in Dorset, Vermont, where timeless architecture and exceptional craftsmanship define this custom Greek Revival residence on 9.9 private acres. Surrounded by mature landscaping, stone walls, and slate terraces, this remarkable home blends classic New England elegance with modern comfort. Designed with meticulous attention to detail, the home features wide-plank floors, hand-plastered walls and ceilings, custom moldings, historic reproduction lighting, finely crafted wainscoting and cabinetry, plus premium materials including slate and copper roofs, Vermont marble, and soapstone. A brick-floored mudroom opens to the heart of the home; an expansive, sun-filled chef's kitchen with butler's pantry, dining area, and bar. Just beyond, a charming kitchen garden provides fresh herbs and seasonal blooms. The adjoining keeping room with fireplace flows into a rustic family/sunroom anchored by a dramatic Vermont fieldstone fireplace. French doors from both rooms open to a gracious slate terrace, creating seamless indoor-outdoor living and entertaining. A hardwired audio system enhances the home's inviting atmosphere. The main level also offers a book-lined library and a private guest bedroom with full bath. Upstairs, the primary suite is a peaceful retreat with a spacious spa-inspired bath. Three additional bedrooms and two full baths provide generous accommodations. Radiant heat throughout ensures year-round comfort. The full basement, complete with radiant heat and a half bath, offers outstanding potential for additional finished living space. Landscaped grounds feature mature gardens, stonework, an outdoor shower, and a hot tub for relaxing beneath the night sky. Completing the property are a two-story attached barn/workshop, a two-car garage with loft storage, and an attached tractor shed. A rare offering which must be seen to fully appreciate. Measurements approximate.

Listed by Carol O'Connor of Four Seasons Sotheby's Int'l Realty

MLS Number 5072035

• Residential Single Family
• PricePerSqFt 1002.72
• Full Bath 1
• Address 249 Sawyer Road
• Construction Existing

Located in Woodstock, Vermont just one mile from the village green, the Alta House offers a rich quality of life filled with poolside sunsets, mountain vistas, proximity to town, and access to endless outdoor recreation opportunities. Enjoy the convenience of living close to the shops, cafes, and restaurants of Woodstock, while being tucked away in your own world above. The 3-bedroom primary residence is perfectly sited to overlook Woodstock's iconic Mount Tom and the Marsh-Billings Museum, Vermont's only National Park. The property sits at the end of a quiet road with only one other neighboring residence. There is a bedroom suite on each of the three levels, allowing family members or guests to claim their own space. The open living room on the main level is a natural gathering place, either by the fire in the winter, or out on the deck in the summertime to take in the views. The adjoining 1,040-sqft modern pool house was completed in 2023, providing a luxurious new extension of the home. Inside is an open floor plan, where floor-to-ceiling windows showcase unobstructed mountain views to the North and West. Thoughtfully designed with a custom Viking kitchen, spa-style walk-in shower, and guest bed, the pool house is ideal for entertaining guests, hosting family parties, or relaxing apres-ski. The outdoor heated pool is a centerpiece of the property, providing four-season enjoyment.

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

MLS Number 5099600

• Residential Single Family
• PricePerSqFt 1121.67
• Full Bath 2
• Address 3544 Harbor Road
• Construction Existing

Available for the first time in over half a century, this extraordinary Shelburne Point home offers an uncompromising lifestyle on the pristine shores of Lake Champlain. Nestled on nearly an acre of prime waterfront, this property represents a rare opportunity to acquire one of Vermont's most coveted lakeside locations. Upon arrival, one is immediately captivated by unobstructed panoramic vistas of the Green Mountains, where the majestic, iconic silhouettes of Camel's Hump and Mount Mansfield are framed across the water's expanse. Tailored for the discerning mariner, the home's waterfront is truly unparalleled. A rare, gently sloping private beach provides wade-in access to the lake, ideal for swimming or launching watercraft. Just beyond the shoreline, three dedicated deep-water moorings await, granting immediate access to the finest cruising grounds Lake Champlain has to offer. What distinguishes this property is its exceptional versatility and uncompromising features. Situated mere moments from the gates of historic Shelburne Farms, this waterfront home enjoys unparalleled proximity to Vermont's premier agricultural landmark. World-class walking trails, majestic pastoral landscapes, and a vibrant community become extensions of your own backyard. This is not merely a residence; it is a legacy waiting for its next chapter.

Listed by Kieran Donnelly of Coldwell Banker Hickok and Boardman

MLS Number 5112053

• Residential Single Family
• PricePerSqFt 398.49
• Full Bath 4
• Construction Existing
• Bedrooms 7

Less than 15 minutes from both Sugarbush Resort and Mad River Glen, and just one mile from Waitsfield Village, this private estate combines expansive Green Mountain views with 38 acres of beautifully established grounds and recreational amenities. A private drive winds through mature trees and perennial gardens to bluestone patios, stacked stone walls, a pond, clay tennis court, and four golf holes, creating an exceptional setting for year round enjoyment. Mountain views extend throughout the property, providing a dramatic backdrop from the gardens, terraces, and residence. Built in 1987, the seven bedroom residence offers multiple spaces for gathering and entertaining, balanced by comfortable private accommodations for guests. The main living room features a soaring cathedral ceiling, exposed beams, a substantial stone fireplace, and floor to ceiling glass opening to a stone patio and mountain views. The kitchen and adjoining morning room overlook the gardens and mountains, while a formal dining room, private office, and first floor guest suite complete the main level. Upstairs, the primary suite enjoys mountain views, a wood burning fireplace, walk in closet, and bath with Danby marble, soaking tub, walk in shower, and sauna. Additional accommodations include an en suite bedroom, a third floor suite, and a finished two bedroom apartment above the garage, offering flexibility for extended stays and guests. A finished lower level provides additional recreation and fitness space with direct access to the grounds.

Listed by Wade Weathers and Averill Cook of LandVest,Inc-Burlington

MLS Number 5094600

• Residential Single Family
• PricePerSqFt 526.79
• Full Bath 4
• Address 5798 South Road
• Construction Existing

Kedron Valley Farm c1850: A classic beauty, perched on a knoll overlooking the idyllic hills and lush meadows of the valley with approx 32 acres. This stunning extended antique post and beam cape is complete with a large traditional 4 story barn with 6 horse stables and equipment sheds offers everything one could wish for in a country property. The grounds include gracious old maples, beautiful perennial gardens, antique moss covered stonewalls, an apple orchard, large swimming pond and a privately sited tennis court. The Estate is meticulously cared for and combines antique craftsmanship with modern touches. The Main house consists of 5 bedrooms including a first floor primary suite with private bath, vaulted ceilings and new large walk in closet. Kitchen features thermador appliances and quartz counters anchored by a large dining room with stunning wood floors. An expansive cozy living room centered by a handsome brick fireplace to curl up with a book on a snowy day. The rooms are spacious and inviting with an abundance of light, exposed original hand-hewn beams and easy access for outdoor entertaining on the brick patio or the new east terrace. Enjoy a separate 3 bedroom Guest House for friends/family with good rental income history. New Tesla Tower for backup power. Located in the heart of horse country and the village of South Woodstock. Enjoy skiing, championship golf and fly fishing on the Black River. Easy access to shopping, restaurants and Upper Valley. Only 8 minutes to Woodstock, 2.5 hours to Boston and 5 hours to NYC. Kedron Valley Farm is a stunning, quintessential farm in the heart of GMHA.

Listed by Gretchjen Smith of Williamson Group Sothebys Intl. Realty

MLS Number 5095093

• Residential Single Family
• PricePerSqFt 438.6
• Full Bath 7
• Address 238 Stowe Hill Road
• Construction Existing

Green Meadows Farm is a rare Southern Vermont estate where timeless character, modern comfort, and exceptional recreational amenities come together across more than 16 picturesque acres. Just minutes from Lake Raponda, downtown Wilmington, Mount Snow, and The Hermitage Club, this remarkable property offers sweeping mountain views, stunning sunsets, and the space to create lasting memories for generations. At the heart of the property is a beautifully maintained six-bedroom farmhouse that blends classic New England charm with thoughtful, energy-efficient upgrades. Warm wood floors, inviting gathering spaces, updated kitchens and baths, and period details throughout create a home that is both elegant and welcoming. A post and beam three-season room with a hot tub provides the perfect place to unwind while taking in the surrounding landscape. The property also includes a separate three-bedroom guest cottage, ideal for extended family, guests, caretakers, or rental opportunities. For entertaining on a grand scale, the impressive party barn features an expansive gathering space with kitchen facilities, an indoor basketball court, and room for everything from family celebrations to recreation and hobbies. The lower level, once the dairy barn, offers abundant storage for vehicles, recreational equipment, tools, and toys. Equestrian enthusiasts will appreciate the horse stables, fenced pasture areas, and open grounds, while outdoor lovers will enjoy the property's proximity to Lake Raponda, skiing, hiking, snowmobiling, and year-round recreation. Multiple outbuildings and flexible spaces create endless possibilities for agricultural use, workshops, or a private family compound. Whether envisioned as an equestrian estate, multigenerational retreat or four-season Vermont getaway, Green Meadows Farm presents an extraordinary opportunity to own one of the Deerfield Valley's most distinctive properties.

Listed by Betsy Wadsworth of Four Seasons Sotheby's Int'l Realty

MLS Number 5112394

• Residential Single Family
• PricePerSqFt 814.69
• Full Bath 4
• Address 60 West Ridge Road
• Construction Existing

Tucked high above Stratton Mountain and set off West Ridge Road, this spectacular mid century contemporary style residence offers a rare combination of architectural character, generous living space, and exceptional access to the mountain. Designed for both entertaining and comfortable family living, the home features four bedrooms each with its own en suite bath, along with an open floor plan that brings everyone together while providing plenty of room to spread out. At the heart of the home is a dramatic living space with a panoramic view of the West River valley and Bromley Mountain beyond. A two car garage adds convenience and storage. Walk to the slopes or take the resort shuttle. Sold unfurnished.

Listed by John Sikes and Jamie Wylie of Stratton Real Estate

MLS Number 5092853

• Residential Single Family
• PricePerSqFt 733.65
• Full Bath 4
• Address 2060 Townshend Road
• Construction Existing

A rare opportunity to own one of Southern Vermont's most remarkable private estates, Riverledge Farm encompasses more than 300 acres in the historic village of Grafton. Nestled in the Green Mountains, this exceptional property combines natural beauty, recreation, and a large homestead. A winding approach framed by mature maple trees and classic stone walls leads to the elegant white farmhouse, where timeless Vermont character meets modern comfort. The residence features six bedrooms, four bathrooms, and two kitchens, complemented by an impressive collection of outbuildings, including a 4,000+ square foot timber frame barn for events, five-bay garage with workshop and offices, seven-bay pole barn, and a three-stall horse barn with heated tack room. Additional accommodations include a separate guest or caretaker residence and two rustic cottages. The substantial acreage includes timberland and open pastures, a half-acre aerated pond, more than two miles of streams, and 6.7 miles of private roads and trails throughout the property. Bordering Mollie Beattie State Forest and the South Branch of the Saxtons River, the land offers opportunities for outdoor recreation, forestry, conservation, maple sugaring, and agricultural pursuits. Three access points to the VAST trail network add to the property's recreational appeal. Meticulously maintained grounds, diverse natural features, and a location near the village of Grafton complete this rare Vermont offering.

Listed by Erin McCormick of KW Vermont

MLS Number 5108098

• Residential Single Family
• PricePerSqFt 685.69
• Full Bath 4
• Address 46 Deer Run
• Construction Existing

BRAND NEW CONSTRUCTION. Set on 0.88 private acres just minutes from Killington and Pico Mountain, this newly built mountain retreat is a true blank slate with some of the best views in town. Including three bedrooms and four bathrooms this is a thoughtfully crafted home. Ceilings soar to 28 feet in the den, 12 feet upstairs and in the primary suite, and 10 feet in the basement, with Anderson windows framing the surrounding scenery. A native granite masonry fireplace anchors the open living area. The kitchen features GE Profile appliances, three ovens, and a Blanco barn sink. Moen matte fixtures, custom woodwork, ¾" knotty pine tongue-and-groove accents, and Danaher-finished yellow pine floors add warmth throughout, while Chicago brick tile brings rustic charm to each bath. Built 20% beyond standard efficiency benchmarks with whole-house spray foam, high-end plumbing, and multi-zone HVAC with high-efficiency AC. Also included: heated garage, ski room with custom cubbies, 1,000-gallon propane tank, and generator readiness. Over 3,000 sq ft of additional unfinished space you could add to the home without an addition. CertainTeed cedar impression siding and a standing seam metal roof with snow guards complete the exterior. A rare chance to own brand-new construction minutes from the lifts and Killington's access road. Call today to learn more about this amazing home!

Listed by Nathan Mastroeni of Elevations Real Estate

MLS Number 5083576

• Residential Single Family
• PricePerSqFt 942.77
• Full Bath 2
• Address 2334 Morse Hill Road
• Construction Existing

Beautiful Dorset Contemporary Offering Privacy, Comfort, and Easy Living. If you've been looking for a private Vermont retreat with room to relax, entertain, and enjoy the beauty of every season, this exceptional custom home may be the perfect fit. Built in 1996 by respected Dorset builder Keith Dodson, this thoughtfully designed 5,731 sq. ft. contemporary sits on 12.15 peaceful acres with a pond and detached four-car garage. Inside, the home offers a welcoming and comfortable layout with 9 rooms, hardwood floors, radiant heat, central air with four zones, and a partial-house generator for added peace of mind. The kitchen features cherry cabinets, Corian countertops, a large island, cathedral ceiling, and easy access to the screened porch, an ideal spot for morning coffee or quiet summer evenings. The dramatic great room creates a wonderful gathering space, with its soaring two-story cathedral ceiling, skylights, exposed beams, built-ins, window seats, and balcony overlook. Throughout the home, warm details such as vertical pine walls, granite stone-faced fireplaces, and generous natural light add character and charm. The exterior combines cedar siding, granite stone accents, and a slate roof for lasting beauty and durability. A detached four-bay garage with direct entry and second-floor storage adds convenience and flexibility. This is a special property for those seeking quality construction, privacy, and a relaxed country lifestyle in one of Vermont's most desirable settings.

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