Very Cool Houses

MLS Number 5048760

• Residential Single Family
• Full Bath 2
• Address 1589 Main Street
• Construction Existing
• Bedrooms 10

Glimmerstone Mansion, an extraordinary legacy estate where timeless elegance meets modern sophistication. Set on 2.4± beautifully landscaped acres, this iconic property, listed on the National Historic Register, has been meticulously restored, thoughtfully upgraded, and exquisitely furnished. At the heart of the estate is the grand 10-bedroom mansion, where nearly every bedroom and gathering space is graced with a stately fireplace, evoking the charm of a bygone era. Five bedrooms offer ensuite baths, each with spa-style finishes, while the owner's private apartment ensures comfort and privacy. Enjoy central air conditioning, high-speed internet, and cell service, ideal for today's work-from-home lifestyle. An entertainer's dream, the lower level reveals an English-style pub complete with a full bar and pool table, opening to an expansive bluestone patio. Step outside to relax in the 6 to 8-person hot tub, gather around the fire pit, or unwind on the gracious covered porch. The estate includes a fully equipped chef's kitchen designed for restaurant-scale culinary experiences and a beautifully renovated, 3,000-square-foot rustic barn, ideal for hosting events of up to 125 guests. Whether envisioned as a luxury retreat, corporate gathering space, or exceptional venue for weddings and celebrations, the possibilities are endless. Once a thriving bed and breakfast, this remarkable estate is ready for its next steward, whether as a private residence or a luxury hospitality venture. Visit the Okemo real estate community today. Taxes are based on current town assessment.

Listed by Kevin Barnes of William Raveis Real Estate Vermont Properties

MLS Number 5094775

• Condo
• Square Feet 2,500
• Bedrooms 5
• New Contruction Existing
• Complex Village Association

Opportunities like this don't come around often at Jay Peak. This spacious 5 bedroom, 4 bath condo sits just off the Grammy Jay ski trail, giving you true slopeside access in one of the mountain's most desirable spots. Owned by the same family since it was built and never rented, it shows a level of care that's hard to find. Inside, the main level offers an easy, open layout made for gathering a bright living area with a gas fireplace, a dining space that fits a crowd, and a well appointed kitchen with a new refrigerator. Large windows bring in soft natural light and views of the surrounding woods. A new furnace installed in 2024 adds peace of mind. Multiple bedroom suites are spread across different levels, giving everyone space and privacy. Additional bedrooms make hosting simple, and the layout handles larger groups without ever feeling cramped. And of course, this is Jay Peak known for some of the most abundant annual snowfall in the East. Step outside and you're moments from skiing, riding, hiking, and all of the resort's four season amenities, including the Pump House Waterpark, Ice Haus Arena, championship golf, restaurants, and miles of trails. It's one of the mountain's largest and most versatile condos in a true slopeside location.

Listed by Mark English of Jim Campbell Real Estate @ Jay

MLS Number 5079104

• Residential Single Family
• Full Bath 1
• Address 1559 Swamp Road
• Construction Existing
• Bedrooms 4

Discover an extraordinary opportunity to own 284.9 acres of Vermont countryside in the scenic town of Fairfield. This remarkable property offers a beautiful mix of open agricultural fields, mature woodland, and abundant wildlife, providing exceptional privacy and endless possibilities for recreation, farming, or a peaceful rural retreat. At the center of the property sits a historic farmhouse built in 1800, offering approximately 1,984 square feet with 4 bedrooms and 1 bathroom. The home is rich with character and presents a wonderful opportunity to personalize a classic Vermont farmhouse while enjoying the surrounding landscape. The expansive acreage provides excellent potential for agriculture, forestry, hunting, trail systems, and outdoor recreation. Protected through a Vermont Land Trust conservation easement, the land has been preserved to maintain its agricultural productivity, natural resources, and scenic beauty for generations while still allowing continued farming, forestry, recreation, and residential use in accordance with the easement. Despite its peaceful rural setting, the property is within driving distance of Jay Peak Resort and Smugglers' Notch, offering easy access to some of Vermont's best skiing, hiking, and four-season outdoor recreation. Large conserved tracts of land of this size are increasingly rare. Whether you're seeking a working agricultural property, recreational escape, or long-term land investment, this unique Fairfield property offers incredible potential and Vermont country charm.

Listed by Michael Preseau of CENTURY 21 North East

MLS Number 5096704

• Residential Single Family
• Full Bath 3
• Address 81 Town Farm Road
• Construction Existing
• Bedrooms 5

Experience the essence of Vermont mountain living in this exceptional five-bedroom, four-and-a-half-bath retreat, ideally located just minutes from Okemo Mountain Resort and offering partial winter views of the mountain. Nestled on approximately one acre and boasting over 3,300 square feet of beautifully finished living space, this inviting home combines timeless mountain character with the comfort and amenities today’s buyers seek. From the moment you enter you will notice a soaring cathedral ceiling, natural woodwork, abundant natural light, and stunning wide-plank wood floors that create a warm and welcoming atmosphere. The spacious living room serves as the heart of the home, where a beautiful fireplace invites family and friends to gather after a day of skiing, hiking, golfing, or exploring Vermont’s four-season recreation. Designed for both everyday living and entertaining, the well-appointed kitchen features stainless steel appliances, beautiful cabinetry, and generous workspace for preparing everything from casual breakfasts to holiday meals. The private primary suite offers a relaxing sanctuary, while four additional bedrooms and multiple baths provide ample space for family and guests. The lower-level family room is the perfect destination for game nights and aprs-ski gatherings, complete with a billiard table and room to unwind. Step outside onto the expansive deck to enjoy fresh mountain air, seasonal views toward Okemo, morning coffee, summer barbecues, and evenings under the stars. A two-car garage offers convenient storage for vehicles and outdoor gear, while the home’s spacious layout comfortably accommodates large gatherings and memorable weekends. Whether you’re searching for a luxury vacation home, an investment opportunity, or a year-round residence, this remarkable property delivers the ideal blend of location, comfort, and mountain lifestyle in one of Vermont’s most sought-after destinations.

Listed by Matthew Bellantoni of Mary W. Davis Realtor & Assoc.,Inc.

MLS Number 5080413

• Residential Single Family
• Full Bath 4
• Address 121 High Meadow Road
• Construction Existing
• Bedrooms 6

Bring the whole household to this great place with lots of room for fun. A 6-bedroom, 4-bathroom Adirondack-style Ski Chalet located in a neighborhood just minutes from the Stratton Mountain Ski Resort, with free door-to-mountain shuttle service on select days. Amenities include four (4) fireplaces, best hot-tub on the market, an in home gym, electric sauna, pool table, SuperChexx Bubble Hockey table, foosball table and corn hole, Sonos entertainment system, and high-speed Wi-Fi and digital cable service. Top of the line WOLF Stove and appliances. 4 years of STRONG rental value. This House checks every box. This is the premier house in the area. Huge owners closet. You have so many options here.

Listed by Ralph Harvey of Listwithfreedom.com

MLS Number 5076203

• Residential Single Family
• Full Bath 1
• Address 563 Rim Road
• Construction Existing
• Bedrooms 4

The Queen's Croft-A Luxurious 4-Bedroom, 5-Bath Custom Vacation Home less than 2 miles to Bear Mountain. Built in 2007 and spanning three beautifully finished levels, this fully furnished and equipped 4,000 sq ft custom home offers the ideal blend of luxury, comfort, and convenience. The property features many thoughtfully designed rooms, and high quality details like heavily-insulated 2x6 construction, 12-inch on center deck framing, and 200 amp electrical service. Private Setting & Exceptional Outdoor Living located on peaceful, wooded, 1.1 acre lot, the home features a large deck for outdoor dining and relaxation, plus a private hot tub for unwinding after a day on the mountain. Ample parking ensures easy access for owners and guests alike. Designed for Mountain Living. Both the upper and lower entryways offer exceptional storage solutions, with the lower foyer offering storage for skis and boards, as well as a custom drying rack for wet boots and gear-keeping everything organized and ready for your next adventure. A striking stone, wood-burning fireplace anchors the main living area, creating a warm and inviting gathering space. Spacious & Fully Appointed. With four bedrooms and five bathrooms across three levels, the layout provides comfort and privacy for groups of all sizes, and the spacious chef's kitchen is perfectly appointed for feeding a hungry crowd. The home comes fully furnished and turnkey, allowing you to step right into the mountain lifestyle without lifting a finger. Strong Rental History. This property has an established rental track record, making it an excellent option for buyers seeking both personal enjoyment and investment potential. Don't miss this rare opportunity to own a luxurious, well maintained mountain retreat in one of Killington's most desirable locations. Ready for immediate enjoyment and income generation, call today to schedule a private showing.

Listed by Bret Williamson of Killington Valley Real Estate

MLS Number 5017773

• Residential Single Family
• Full Bath 2
• Address 36 Emerson Drive
• Construction Existing
• Bedrooms 3

Welcome to your dream home! Nestled on 36.6 acres of private, picturesque land in Jericho, this stunning one-level residence offers the perfect blend of luxury, comfort & functionality. As you enter through the front covered porch, you'll step into the great room, highlighted by a dbl-sided gas fireplace & 9-foot ceilings. The gourmet kitchen features a granite island w/ a dbl oven, dbl dishwasher, gas cooktop & custom Simpson cabinetry w/ under-cabinet lighting. A formal dining room provides the perfect setting for entertaining & offers direct access to an outdoor deck. The primary bedroom suite is complete w/ a walk-in closet & a private bath, which boasts a Jacuzzi tub, stand-up shower & dual vanities. Off the 3-car garage, you'll find a spacious mudroom a 1/2 bath w/ laundry along w/ 2 additional generously sized bedrooms, another full bath w/ dual vanities & a bonus room/office. The full walk-out basement is partially finished offering potential for additional living or entertainment space. Energy efficiency abounds w/ owned solar panels, radiant floor heat in the kitchen & entry & a propane boiler w/ the option to switch to an outdoor wood boiler. For all your storage needs, a large 32x40 detached 2-bay garage, complete w/ a 32x38 addition, offers ample space for vehicles & equipment w/ the potential to finish the 2nd level. Located on a private road, this exceptional property offers tranquility & seclusion while being just a short drive to I-89 & nearby amenities!

Listed by Daniel Titus of Flex Realty

MLS Number 5095057

• Residential Single Family
• Address 145 The Plateau
• Construction Existing
• Bedrooms 4
• Bathroom 4

"The Plateau", originally part of the Kennedy Biscuit Co. (Nabisco) family estate, is nestled on a plateau at the end of a private road which greets you with open fields, mature trees, beautiful gardens, and a protected front-and-center view of Mt. Ascutney to the West and the Connecticut River to the East. This private peaceful setting includes an inground pool for those hot summer days, and two porches: one open air and one screened-in, with views into the New Hampshire hillsides. Inside, the house is open and bright with a wonderful flow throughout. The large living room features a wood-burning fireplace and plenty of windows streaming in lots of natural light. The formal dining room, with built-in cabinets and a second wood burning fireplace, connects to the kitchen which is open to the family room. A beautiful spindle staircase with oversized steps leads you upstairs to the four bedrooms, including the primary with an ensuite bath and an attached office. The main guest/children's bedroom features a magnificent turret style sunroom taking in views of the Connecticut River, and a second set of stairs leads back down to the mudroom. The full basement offers plenty of storage and all the utilities. The large 2 story garage offers room for 4 vehicles and plenty of storage on the 2nd floor. This unique property presents a rare opportunity to own a special homestead in the Windsor area, just minutes from downtown shopping and restaurants.

Listed by Dan Noble of Snyder Donegan Real Estate Group

MLS Number 5103511

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

Exceptional Vermont country property ideally situated within a serene pastoral setting with wonderful views, yet just minutes from the Dorset Village Green. Set on 16 picturesque acres, this remarkable offering features a spacious 4-bedroom main residence, a newly renovated 1-bedroom guest house, an in-law studio with a full bath, a classic barn, and a machine shed. Rich in Vermont charm, the main residence showcases two fireplaces, exposed beams, beautiful wood flooring, and abundant natural light. The farmhouse-inspired chef's kitchen is thoughtfully appointed with a premium Bertazzoni gas range, top-of-the-line appliances, generous storage, and oversized windows overlooking the front lawn and surrounding pasture. The inviting lodge room is perfect for gathering around the fireplace, while the spacious formal dining room creates an elegant setting for entertaining family and friends. The main floor primary suite wing serves as a peaceful retreat, featuring an adjoining office, extensive storage, and an oversized spa-inspired bathroom with a soaking tub and walk-in shower. Large windows fill the space with natural light, enhancing its tranquil atmosphere. Upstairs, three generously sized bedrooms provide comfortable accommodation for family and guests, complimented by a full bath. The stone patio and spacious covered porch are ideal for al fresco dining while enjoying sunset views. Outside, mature gardens, beautifully landscaped grounds, rolling pastures, and classic farm buildings create the quintessential Vermont country lifestyle. Ideally located just minutes to the New York border and approximately 30 minutes to Saratoga Springs, this exceptional property offers the perfect balance of peaceful Vermont living and convenient access. Whether enjoyed as a private retreat, multigenerational residence, or equestrian property, this exceptional offering combines timeless character, versatility, and natural beauty in one of Southern Vermont's most desirable locations.

Listed by Kim Morgan-Wohler of Wohler Realty Group, Britt Wohler of WOHLER REALTY GROUP

MLS Number 5086522

• Commercial
• Village Woodstock
• Address 15 Central Street
• Year Built 1840
• Square Feet 6,612

15 Central Street is one of the finest commercial locations in Woodstock with two of the most creative and successful businesses as the anchor tenants. The historic building has adapted to changes over the course of its long history of uses including residential, barber shop, a dance & pool hall, law office, architectural services and a variety of mercantile endeavors. Notably, the building was the headquarters of Lt Colonel Peter T. Washburn, who led the 1st Vermont Regiment troops in their crucial role at Gettysburg. He returned to the roles of Adjutant and Inspector General to organize and direct Vermont's military efforts through the rest of the Civil War from his offices at 15 Central Street. The current owners, recognizing it was time to adapt the building to the 21st Century, developed plans to upgrade and modernize the second and third floors for mixed use including an incredible residential unit with exposed brick walls and timber framing. The story high historic windows have been restored, and the second level has been reframed with new sheetrock. The third level partition walls have been removed to create a dramatic open area with views over the village to the north and south leaving the finishes and uses of the two levels up to your imagination. This is a once-in-a-lifetime opportunity to acquire a property with a remarkable history and become part of creating Woodstock's future. Note: Gross income reduced in 2024 due to renovation

Listed by Danny Kogut and Laird Bradley of Williamson Group Sothebys Intl. Realty

MLS Number 5092750

• Land
• Village Burke
• Address 98 Vt Route 114
• Acreage 4.9
• Area VT-Caledonia

This is the well known spot called the "log Yard" at the beginning of East Burke Village, Currently being rented with no lease by a log broker company for the storage of logs. The owners of the land also have 24 storage units on the property. It is often used for event parking and Kingdom Trails parking. Lots of room for more storage units and other potential uses.

Listed by Andrea Kupetz of Century 21 Farm & Forest/Burke