Very Cool Houses

MLS Number 5078166

• Residential Single Family
• Full Bath 3
• Address 316 South Street
• Construction Existing
• Bedrooms 3

Set along the coveted western shoreline of Lake Champlain in the heart of the Champlain Islands, this extraordinary 13+ acre estate offers over 350 feet of prime lake frontage and sweeping Adirondack views. With its prized west-facing orientation, each evening ends with spectacular sunsets reflected across the water. Custom built in classic Adirondack style and clad in timeless cedar shingles, the residence offers more than 4,000 square feet of thoughtfully designed living space. The dramatic 33 x 38 foot great room is the architectural centerpiece, showcasing a commanding stone fireplace, and walls of glass that frame the lake beyond. Gleaming birch floors and natural wood finishes create warmth and understated elegance throughout. Radiant heated floors provide exceptional comfort, while mini-split systems offer efficient cooling in summer months. A geothermal heating system, paired with solar roof panels and solar trackers, underscores a commitment to sustainability and energy efficiency without sacrificing luxury. The chef's kitchen, appointed with cherry and birch cabinetry, is designed for both refined entertaining and relaxed daily living. A private first-floor primary suite offers a serene retreat, while three additional bedrooms and well-appointed baths provide generous accommodations for family and guests. Multiple porches and expansive decks capture lake breezes and uninterrupted views. Step to your shoreline to enjoy boating, swimming, and world-class fishing. The expansive acreage allows for a guest house, gentleman's farm, equestrian pursuits, or simply preserving privacy and pastoral beauty. Though peacefully secluded, this exceptional property is just 20 miles to Burlington and approximately one hour to Montreal-offering the perfect balance of privacy, proximity, and refined Lake Champlain living.

Listed by Kelly Byers and Mary Palmer of Four Seasons Sotheby's Int'l Realty

MLS Number 5077313

• Residential Single Family
• Full Bath 6
• Construction Existing
• Bedrooms 5
• Bathroom 7

Solitude home at the top of the hill awaits! Solitude on Okemo Mountain, where this exceptional five-bedroom home captures the ultimate ski location, breathtaking long-range views, and unparalleled privacy. Perfectly positioned to embrace the beauty of the surrounding mountains, this residence offers a rare opportunity to enjoy true slope-side living in one of Vermont's most sought-after resort communities. The main floor offers a sunken living room with views of the Okemo Valley. Off the living room is a dining room and kitchen with a large island and room for entertaining. The family room off the kitchen has a full bathroom and access to the large deck with a hot tub overlooking the ski trail. From the main floor, you can access the heated garage. Above the garage is a primary suite. The primary suite has a vaulted ceiling,a gas fireplace, a balcony, and a soaking tub with window views. The bathroom has a large shower, a double vanity, and a walk-in closet. Back down to the main level, you can access another second floor with 2 en-suites, each with a full bathroom. There is a den and a full bathroom to complete the second level. The basement area offers a full game room and family room, 2 additional bedrooms, a full bathroom, a half-court basketball room, and a mudroom, which opens to the bridge that brings you to the ski trail. The current homeowner has thoughtfully enhanced the property with numerous upgrades, including new mechanical systems and additional improvements that enhance efficiency and livability. Step outside and experience mountain living at its finest in this secluded setting, where serenity meets adventure right at your doorstep. Whether you're relaxing after a day on the slopes or entertaining while taking in the sweeping vistas, this home delivers the very best of resort lifestyle. If you're looking for the best of the best, call us today to schedule your private showing and discover this extraordinary mountain retreat.

Listed by Katherine Burns of William Raveis Real Estate Vermont Properties

MLS Number 5090134

• Residential Single Family
• Full Bath 4
• Construction Existing
• Bedrooms 5
• Bathroom 5

The Drake House is a rare Vermont landmark, nearly two centuries in the making and thoughtfully carried forward by generations of careful stewards. Built in 1825 by Asaph Drake and his wife, this distinguished brick Federal home has long held an important place in the Middlebury area, with later connections to the Morgan Horse Farm, ownership by a Middlebury College president, and listing on the National Register of Historic Places. Most recently purchased in 2023, the 5,030-square-foot home has been meticulously modernized for contemporary living while preserving the character, craftsmanship, and soul that make it irreplaceable. Light-drenched interiors feature original pumpkin pine floors, historic brickwork, marble accents, reclaimed oak flooring, a restored archway, and elevated updates throughout, including a custom kitchen with coffered ceilings, walnut island, Fisher & Paykel dishwasher, and black enamel AGA propane range. Surrounded by approximately 650 acres of conserved land just five minutes from Middlebury village, the property feels deeply private while remaining closely connected to the landscape, with gardens, a pond, outdoor living spaces, and access to the MALT system's 18-mile trail network. Inside, gracious gathering spaces, a parlor with fireplace and beehive/pizza oven, a serene primary wing with office and cedar sauna, and a wine cellar create a home that is both historic and deeply livable. A post-and-beam barn/garage with guest apartment, additional barn, and second driveway complete this beautifully renewed Federal-era retreat, ready for its next chapter.

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

MLS Number 5051212

• Residential Single Family
• Full Bath 3
• Village Ludlow
• Construction Existing
• Bedrooms 5

Welcome to your mountain sanctuary in the heart of Solitude VillageOkemo’s premier slopeside community. This luxurious 5-bedroom, 3-bathroom retreat offers true ski-on/ski-off access, allowing you to hit the Rising Star Trail or Moon Shadow right from your doorstep. Step inside to a warm, elegant interior featuring radiant-heated tile and rich hardwood floors throughout. The expansive great room, with its stunning stone fireplace and vaulted ceilings, creates the perfect aprs-ski gathering space. Just off the great room, a custom beverage bar with seating for three invites you to unwind with a cocktail while watching the snow fall. The chef’s kitchen is appointed with high-end appliances, granite countertops, and custom cabinetryideal for entertaining. The dining room comfortably seats twelve, making it perfect for holidays and celebrations. After a day on the slopes, drop your gear in the well-designed mudroom with built-in cubbies before heading down to the walkout lower levelcomplete with a pool table, exercise space, sauna, and hot tub for ultimate relaxation. A large game room with tons of comfortable seating for movie watching. The spacious primary suite includes a private balcony, perfect for morning coffee with mountain views. Additional features include a dramatic carport entry, two-car garage, ample storage, and timeless craftsmanship throughout. Whether you're seeking a serene winter escape or an active four-season retreat, this home delivers. ROFR

Listed by Joseph Karl of William Raveis Real Estate Vermont Properties

MLS Number 5091062

• Residential Single Family
• Full Bath 2
• Address 66 Hollow Farm Road
• Construction Existing
• Bedrooms 5

CURTIS HOLLOW FARM- Exceptional estate on the western edge of Woodstock offering 105 diverse acres bordering Calvin Coolidge State Forest. The updated main house features 5 bedrooms and 4 baths, filled with abundant natural light and thoughtfully designed for both large gatherings and quiet retreat spaces. The open-concept main level includes a spacious living room with picture windows overlooking the landscaped grounds, a recently updated chef's kitchen with a stunning Mercury/Aga range, and generous dining space nearby. On the east side of this level, the original historic homestead-with its native timbers and stone fireplace-creates a warm and intimate dining experience. A wraparound deck provides additional space for outdoor dining and entertaining, while bedroom with its own bath completes this floor. Upstairs are 4 additional bedrooms, several featuring charming portal windows with views over the surrounding fields & hills. The primary suite is spacious and inviting, highlighted by exposed historic timbers, a sitting area, direct access to an upper deck, and a spa-inspired bath. On the uppermost level, the cupola offers the perfect yoga studio or quiet reading nook, complete with its own private deck. The grounds are truly magical, with an extensive trail network throughout the property and direct access to a magnificent waterfall and swimming hole just beyond the lot line within the State Forest. Large level lawns, mature landscaping, and a brook flowing along the southern side of the property add to its private tranquility. Nestled beside the brook is the guest house, known as the Brook House-a well-maintained 3-bedroom, 2-bath home privately sited away from the main residence, with its own lawn and deck overlooking the water below. With a convenient location offering easy access to Woodstock and Bridgewater Villages and a short drive to Killington Mountain Resort, this stunning estate is the consummate blend of privacy, charm, and modern convenience.

Listed by David Donegan of Snyder Donegan Real Estate Group

MLS Number 5083576

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

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

MLS Number 4971898

• Residential Single Family
• Full Bath 1
• Address 36 Woffenden Road
• Construction Existing
• Bedrooms 6

Discover the quintessential Vermont lifestyle at historic Wheeler Farm! Nestled amid its own 260+/- acres of scenic beauty, this 6-bedroom farmhouse embodies rural farmhouse charm. Open meadows, green hay fields and the sugarhouse's steam on spring days barely begin to tell the story of all this special property holds. Boasting a coveted southeast exposure, the home and land are cheerful and whimsical and yes it gets even better-this is waterfront property that offers substantial frontage on the North Branch of the Deerfield River, a haven for fly fishing & serenity. For the farmer in you, two livestock barns provide ample space for your animals or envision more-the potential to be certified organic or transform these barns into charming event spaces or the farm into a Bed and Breakfast to blend Vermont's rural allure with modern comfort. This property is an opportunity waiting to be realized. With 5 identified potential new home sites, you may consider creating a family compound or explore development possibilities. Additionally, there's a sugar house and sugar lot, operated with modern efficiency for maple syrup production. Historic Wilmington, is only a stone's throw away and Mount Snow and the prestigious Hermitage Club are just a few miles North. Rarely does an opportunity like this arise. While currently part of Vermont's Current Use program, removal is an option upon sale, making your vision even more attainable. Unlock the limitless posibilities at Wheeler Farm!

Listed by Melissa Ellis of Southern Vermont Realty Group

MLS Number 5089125

• Residential Single Family
• Full Bath 6
• Construction Existing
• Bedrooms 4
• Bathroom 7

Set behind a gated entrance and approached by a winding private drive, this custom-designed fully-furnished residence is surrounded by 63.15 acres of beautifully landscaped, estate-like grounds offering exceptional privacy just minutes from Essex Junction and Burlington. Thoughtfully positioned to capture the natural beauty of the property, the home offers a rare balance of quiet seclusion and convenient access to nearby golf, dining, and Vermont's mountains. Designed for both refined entertaining and comfortable daily living, the home blends expansive gathering spaces with warm, inviting interiors. At the center of the main level, the chef's kitchen features a Wolf cooktop, oversized island, walk-in pantry, and custom copper-lined sink, flowing easily into both formal and casual living areas. Large windows and outdoor access throughout the home create a seamless connection to the surrounding landscape and expansive rear deck. With four bedrooms and 6.5 baths, the layout offers privacy and flexibility for hosting. The primary suite serves as a peaceful retreat with a spa-like bath, soaking tub, and generous walk-in closet, while three additional en suite bedrooms provide exceptional comfort. A third-level media room, bonus spaces, and a distinctive cupola with sweeping views add to the character and versatility you'll find throughout this home. The walkout lower level was designed with entertaining in mind, featuring a recreation room, bar, wine cellar, office, and full bath. Outdoors, the property continues to unfold as a private Vermont retreat with a pond and dock, raised garden beds, fire pit area, and professionally designed landscaping that brings color and enjoyment throughout the seasons. Offering the scale and setting of a country estate without sacrificing proximity to Greater Burlington conveniences, this is a property for those who value privacy, open space, and an elevated Vermont lifestyle.

Listed by Sarah Harrington of Coldwell Banker Hickok and Boardman

MLS Number 5085635

• Residential Single Family
• Full Bath 1
• Address 59 Garden Loop Road
• Construction New Construction
• Bedrooms 4

Move into this brand new stunning custom contemporary set on over 3 acres in coveted Stratton ski country. This exceptional modern design offers elevated living with superior craftsmanship and sweeping endless views. Featuring four well appointed ensuites with polished baths boasting radiant heated floors, half bath, family room and dual laundry areas. The well designed kitchen with Italian custom cabinetry offers an impressive honed granite island, Thor oven and 6 burner cooktop, Bosch dishwasher, Zline frig/freezer. Beautiful French oak floors throughout. Brizo hardware. Sonos sound system. Air conditioning. HVAC system is variable refrigerant flow (VRF). Weather Shield windows and doors. Heated two car garage. HOA fees include road and driveway maintenance, caretaking, lawn care and private winter shuttle service to Stratton's base lodge. We are nearing completion of Luna Thermowood exterior siding work with landscaping including blue stone patio next. (added digital image of lawn) Stylishly furnished. Experience captivating sunsets from most rooms, your deck and covered porch. We welcome your interest and enthusiasm, come take a look. This is not just a home but a mountain statement.

Listed by Terry Hill of Berkshire Hathaway HomeServices Stratton Home

MLS Number 5002873

• Residential Single Family
• Full Bath 2
• Address 61 Academy Circle
• Construction Existing
• Bedrooms 6

Hyacinth House has been a landmark property in the historic village of South Woodstock from its early settlement in the 1800's. Sited on a knoll overlooking the Kedron Brook this grand residence has been carefully restored by talented craftsmen. Taking care to keep the beautiful original details the owners have brought the systems into the 21st century with the highest quality of materials. The back ell seamlessly ties into the original brick Federal and offers additional spaces for entertaining guests including the Pine Room with its' large fireplace for snowy winter nights. The brick Federal consists of formal living room, dining room, library and gourmet kitchen with walk in pantry. On the second floor there are 2 ensuite bedrooms,4 more bedrooms, 2 baths and large laundry room. The third floor offers the surprise of a family room that was originally a ballroom with curved ceiling. There is also a bright studio and half bath on that level. The new attached oversize 2 car garage is accessed from the Pine Room and the fully renovated basement. The 2+/- acres comprises of lovely landscaping around the home and plenty of land for gardens . The 18th century barn and corn crib lend much charm to the setting. There are 8 additional acres for sale if one would like to expand the property. Walk to the charming village store and enjoy dinner on the porch of the Ransom Tavern. Only 5 miles to Woodstock and a short drive to multiple ski areas. South Woodstock is truly a bucolic place to call home! Call today for a private viewing.

Listed by Carol Wood of Williamson Group Sothebys Intl. Realty