Very Cool Houses

MLS Number 5099760

• Residential Single Family
• Full Bath 6
• Address 817 Gulf Road
• Construction Existing
• Bedrooms 6

One of the best opportunities our firm has ever presented. 192 acres, mountain views, pond, stream and waterfall - and three dwelling structures plus many outbuildings, in desirable Barnard VT, just 13 minutes drive to Woodstock village green. This is an estate sale of the late owner. This land with the Old Dean House (a cape house on a pond) was purchased and owned by a prominent family in Barnard and Hawaii. The owner began construction some 20 years ago of a magnificent timber frame residence, complete with elevator, observatory turret, radiant heated concrete floors, Viessmann furnace, full solar array, backup generator and 7 bays of solid wood garage doors (a collection of more than 25 vintage cars were stored at the garages at the house until about 6 years ago). The entire house was closed in, weather-tight and heated - and then construction stopped there but has been heated and kept heated ever since. It mainly needs interior finishing - floors, bathrooms kitchens, interior doors and so forth. All the architectural plans for the house are still there including architectural models of the home. In addition to the main residence, there is the original 3-bedroom 2-bath cape (that the owner lived in for many years), and a 2-car garage with full apartment above it - currently occupied by the caretakers of over 20 years. The caretakers can either stay on or vacate prior to closing - at the buyers discretion. There are various other outbuildings and MILES of trails complete this offering. Since the sale is being handled by the Trustee for the late owner, this property is being sold AS-IS, in its current condition. CAMERAS ARE ACTIVE. NO DRIVE-BYs. CALL FOR AN APPOINTMENT.

Listed by John Snyder of Snyder Donegan Real Estate Group

MLS Number 5097566

• Residential Single Family
• Full Bath 7
• Construction Existing
• Bedrooms 7
• Bathroom 8

Cold Moon Farm: Where Dreams Take Root! Ever imagine waking up to mountain vistas & the gentle sound of contented goats? This legendary Vermont property, makes that dream a reality. This once-in-a-lifetime offering is brimming with possibilities, whether you crave a sprawling family haven, a luxurious personal retreat, or a chance to revive the farm's celebrated B&B. Prepare to be Enchanted! An open floor plan unfolds into a breathtaking two-story great room, showcasing panoramic mountain views. Prepare feasts fit for royalty in the commercial-grade kitchen, then unwind in one of 6 spacious bedrooms, each with a private en-suite bath. Rise with the sun on the first-floor primary suite: Cozy up by the fireplace, or step out to the deck & savor the scenery with a steaming cup of coffee. Unwind in the lower-level living room, a haven for gatherings. An exercise room, office, & billiard room cater to every mood, while a walk-out door beckons you farm-side. A two-level barn currently houses a menagerie of friendly goats, sheep, chickens, & ducks! A heated garage provides convenient access, while a workshop & storage area keep things organized. The milking room & stalls below are ready for those who dream of a farm-to-table lifestyle. Plus, a charming 1-bedroom, 1-bath guesthouse offers the perfect space for visiting family, friends or potential rental income. Just 4 mi. from Stratton & close to Bromley, Magic & Snow, Cold Moon Farm puts you at the heart of all that Vermont offers! Listing agent is an owner of this property.

Listed by Tg Glazer of Winhall Real Estate

MLS Number 5101089

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

Set high above the surrounding countryside with sweeping views toward Salem Lake and the mountains beyond, this extraordinary 85.7 acre estate offers a rare combination of luxury, privacy, open land, and future possibilities. Thoughtfully positioned to capture the spectacular setting, the custom-built residence was designed for elegant entertaining and comfortable everyday living. Soaring ceilings, dramatic open spaces, a stunning stone fireplace, and walls of windows showcase the surrounding landscape from nearly every room. At the heart of the home, the chef's kitchen features premium appliances, custom cabinetry, generous workspace, and an effortless connection to the dining and living areas. The primary suite is a peaceful retreat with a private deck, spa-inspired bath, and panoramic views. Spacious guest bedrooms and thoughtfully designed living spaces continue throughout the upper level. Expansive decks overlook rolling fields and distant mountains, offering the perfect place to enjoy Vermont's changing seasons. Additional features include a heated attached garage, substantial unfinished bonus space above the garage, and a radiant-heated walkout lower level with multiple exterior access points. These areas offer outstanding potential for future living space, recreation, a studio, or multigenerational use. Generator wiring and a whole-house fan add everyday convenience. Beyond the 14.8-acre homesite, an additional 70.9 acres are included and have already been subdivided into four separate parcels. This creates exceptional flexibility for a future family compound, guest residences subject to applicable permits and approvals, agricultural use, long-term investment, or preservation of the property's privacy and pastoral surroundings. The open fields have been carefully maintained and hayed for decades. Whether envisioned as a luxury primary residence, Vermont retreat, or legacy estate, this is a remarkable opportunity to own an irreplaceable piece of the NEK.

Listed by Erika Pierce of Four Seasons Sotheby's Int'l Realty

MLS Number 5082662

• Residential Single Family
• Full Bath 3
• Address 234 East Road
• Construction Existing
• Bedrooms 5

Introducing *The Greystone Estate*-a truly one-of-a-kind, fully restored Vermont farmhouse that masterfully blends 200 years of rich history with today's modern luxury. Set on a breathtaking 10-acre parcel, this extraordinary property captures everything you envision in a quintessential Vermont retreat-rolling open meadow, mature trees, a peaceful babbling brook, and complete privacy surrounded by nature. Meticulously renovated over a 2-year restoration, every inch of this historic home has been thoughtfully reimagined while preserving its original charm and character. Exposed hand-hewn beams, wide plank floors, and timeless architectural details are seamlessly paired with high-end finishes and modern systems, offering the perfect balance of old-world craftsmanship and contemporary comfort. The home features three stunning primary bedroom suites-one conveniently located on the main level and two on the second floor-each offering its own unique ambiance and refined design. The gourmet kitchen, inviting living spaces, and beautifully appointed interiors create an atmosphere that is both warm and sophisticated. The Greystone Estate will convey with a few incredible collection pieces of rare antiques, artwork, and curated pieces accumulated over two centuries-making this a true piece of timeless history. Whether you're seeking a remarkable primary residence, private retreat, or proven income-producing property, this home has been a highly successful short-term rental. Adding even more value is the detached “Buck Lodge,” ideal for guests, extended family, or additional rental income. For those looking to expand, one neighboring 10-acre parcel is still available, presenting the rare opportunity to create a 20-acre legacy estate. Opportunities like this are exceedingly rare-a property of this caliber, scale, historical significance, and level of finish is truly unmatched. The Greystone Estate is not just a home, it's a legacy.

Listed by Blake Gintof of Signature Properties of Vermont

MLS Number 5049627

• Residential Single Family
• Full Bath 2
• Construction Existing
• Bedrooms 5
• Bathroom 4

Discover your Vermont sanctuary just 2 miles from stunning Lake Bomoseen and a short drive to the scenic Half Moon State Park! This exceptional home offers a perfect blend of natural beauty and luxurious comfort nestled within over 80 acres of lush land. Imagine waking up to breathtaking water features - a deep spring-fed pond, a majestic fifty-foot waterfall, and a tranquil year-round brook gently flowing behind the house - that create a peaceful, inspiring setting every day. This unique property boasts three distinct living areas, centered around a serene interior stone garden that invites relaxation and connection. The main house, an inviting guest wing, and a spa/living area with a swim-current pool, plunge pool, entertainment zone, cozy caf, and exercise area give everyone space to enjoy. Throughout, you'll find exceptional finishes and thoughtful upgrades, including a modernized primary kitchen, solar energy system, and mini-splits for ultimate comfort. With up to five bedrooms and separate spaces for privacy, this home is designed for creating lifelong memories in harmony with nature. The property’s expansive land offers endless outdoor adventures and privacy in a beautiful Vermont setting. Don’t miss this once-in-a-lifetime opportunity! Schedule your showing today and experience firsthand this one-of-a-kind Vermont retreat - your dream home awaits!

Listed by Michael Johnston of Coldwell Banker Hickok and Boardman

MLS Number 5100663

• Residential Single Family
• Full Bath 1
• Address 791 Journey End
• Construction Existing
• Bedrooms 4

Imagine wrapping up a day on the slopes and rolling home to your own slice of Mendon serenity; 3 bedroom, 2.5 baths and 2,244 square feet of modern luxury waiting down a long dirt driveway for you. This thoughtfully built home puts craftsmanship front and center. Radiant floors warm the main level, the three car garage, and the basement alike. The basement is an expansive, wide-open canvas ready to finish; with plumbing already in place to add a wet bar. A modern farmhouse aesthetic sets the tone throughout, beginning with an open floor plan, designer kitchen offers striking finishes with genuine functionality including a huge island, open to the living/dining areas with mountain views off the back balcony or front porch, Slip away to your primary suite featuring a soaking tub, unique large shower and huge walk-in closet. A practical mudroom is great for ski gear plus a huge upper bonus room. Equestrians, rejoice...A dedicated horse barn, rolling pasture and privacy is increasingly hard to come by, framed by mature trees and mountain scenery but the Location seals the deal; Pico Ski Area is a mere 5 minutes away, while world-class Killington Ski Resort is just 10. Prefer fairways to powder? Green Mountain National Golf Course is a quick drive, and Rutland for shopping and dining.

Listed by Nancy Greenwood of Watson Realty & Associates

MLS Number 5102943

• Residential Single Family
• Full Bath 3
• Address 1508 Sugarhouse Road
• Construction Existing
• Bedrooms 6

This exceptional home offers a wonderful combination of old and new, where a historic 1860's farmhouse has been gutted and totally redone with great care. The result is a comfortable home that provides great areas for gathering as well as private spaces, featuring a total of 6 bedrooms. With all new insulation, wiring, and modern systems including the septic and waterthe property functions seamlessly like a brand new home. The original house now contains a lovely formal living room and a library separated by glass doors, as well as a welcoming eat-in kitchen complete with a walk-in pantry. There is also a fully enclosed Porch off kitch the top floor of this section accommodates two bedrooms and a half bath. Extending the living space a connection to the former barn/garage has been masterfully transformed into a family room with cathedral ceilings and a loft above, accompanied by two guest bedrooms and a full bath. Back on the main floor, you'll find a large primary bedroom suite complete with a 3/4 bath with double sinks, and a huge walk-in closet with an integrated laundry room. Continuing through the office and mudroom, you will find a dedicated home gym featuring a sauna and a half bath. Located over the 3-bay garage is a spacious apartment featuring an open main living area, a comfortable bedroom, an office, a 3/4 bath, and a separate laundry room. A composite deck provides wonderful outdoor living space and direct views of Burke Mountain. Equipped with both stairs and an elevator for access, this space is ideal for multi-generational living. The surrounding grounds are spectacular, offering a private firepit area in the back away from the house, multiple covered porches, and heated patio spaces that eliminate the stress of shoveling snow. there are 2 200 amp services in the house. All set on a 3-acre parcel showcasing grand views to the south of Burke Mountain. Thoughtfully designed with nothing lacking, this home must be seen to fully appreciate its quality.

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

MLS Number 5077331

• Residential Single Family
• Full Bath 4
• Construction Existing
• 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

MLS Number 5082283

• Residential Single Family
• Full Bath 1
• Address 25 Buell Street
• Construction Existing
• Bedrooms 4

Lovingly and meticulously updated Victorian blends historic charm with refined contemporary living. Since 2019, this gorgeous home has been extensively renovated with a new kitchen, three new baths, new lighting, and efficient heat pump for whole house year-round comfort, all with new wiring and plumbing. All the work is done. Inside, exquisite unpainted woodwork, pocket doors, stained glass, and original hardwood floors create a warm, light-filled ambiance. Double wall construction creates a surprisingly quiet interior. The chef's kitchen, rebuilt to the studs, showcases custom cabinetry, Danby VT marble counters and large island, 4-burner gas range with griddle and electric oven, wine fridge, coffee bar, and original pantry - perfect for entertaining. The expansive primary suite is a sanctuary, featuring a spa-like marble bath with soaking tub, steam shower, heated towel bars, and radiant heat. Additional distinctive spaces include a soaring post-and-beam attic and “tower room” ideal for a studio, office, or retreat, plus a local quarried red stone basement with wine cellar and gym. Outdoors, enjoy a gracious wrap-around porch, private courtyard, and lush gardens. Ideally located near downtown, with easy access to shops, dining, the waterfront, UVM, Champlain College, and the UVM Medical Center. This rare blend of beautiful design, highest quality construction, and modern luxury features sets the stage for an exceptional urban lifestyle. City records reflect six bedrooms; there is a first- floor office with adjoining bath which could be a fifth bedroom. While a wonderful home, the property is located in the downtown zoning district allowing for a wide range of commercial, retail, hospitality uses.

Listed by Brian M. Boardman of Coldwell Banker Hickok and Boardman

MLS Number 5046479

• Residential Single Family
• Full Bath 15
• Construction Existing
• Bedrooms 17
• Bathroom 20

The historic Arlington Inn & Spa is the centerpiece of scenic Arlington, Vermont. It features a tavern, restaurant and massage spa room. There are 15 guest rooms in 3 buildings, and an antique event barn on over 3.5 beautifully landscaped acres. This unique property can easily be configured in many creative ways. It could remain as an inn with a restaurant and bar. It could become a restaurant and event destination for weddings and parties. And it would make a wonderful family compound or corporate retreat. In addition to three guest suites, the c. 1848 Main Inn offers a commercial kitchen serving formal and informal dining spaces and the fully renovated Deming Tavern. The romantic Tavern features an antique bar front crafted from a pulpit from the Old First Church in Bennington and Pullman Railcar lighting in a nod to Martin Chester Deming, the original owner of the property and a railroad magnate. While respecting historical detail, the current owners have added modern conveniences and updates. This includes underground utilities, fiber optic high-speed WIFI internet, SmartTV in every room, portable a/c units and USB port alarm clocks. Antique romance with 21st century upgrades! Guests are free to enjoy the front and back yards, patio areas, gazebo and beautiful perennial gardens. This special property is ready for the next stewards to take it to a new level! Please click on the "unbranded tour" link for a virtual tour of the property.

Listed by Vicki Wilson of Maple Leaf Real Estate

MLS Number 5094275

• Residential Single Family
• Full Bath 2
• Address 514 Robinson Road
• Construction Existing
• Bedrooms 3

Experience the essence of Vermont living at Lanes End Farm, a meticulously rebuilt farmhouse estate blending New England charm with modern luxury. Set at the end of a tree lined, town maintained gravel road, the property offers serenity, seclusion, and sweeping mountain views. Inside, an open plan creates effortless flow between the light filled kitchen, dining, and living areas. A wood burning fireplace anchors the living space, while west facing windows capture unforgettable sunsets. Step onto the wraparound rear deck, partially covered for all season use, to enjoy al fresco dining, stargazing, and the panoramic scenery. Upstairs, the primary suite provides a peaceful escape with a walk in closet and spa like bath. A separate guest wing with its own staircase includes two bedrooms and a full bath, ideal for hosting family and friends. Designed for today's flexible lifestyle, the home also features a bonus room over the heated 3 bay garage, perfect for an office, studio, or media lounge, and a finished walkout basement suited for a home gym, recreation, or guest space. Modern comforts include radiant heat, a second floor laundry room, and a whole house generator. The 73 acre property features a handsome two story Vermont barn with five or more stalls for equestrian use, hobby farming, or storage, along with a rustic cabin ready to become a guest house, studio, or caretaker's residence. Offered furnished with farm equipment negotiable, this beautifully maintained property is ready for immediate enjoyment. Located in the quintessential Vermont town of Shrewsbury, known for scenic beauty, historic farms, and its beloved general store, the property is a short drive to Rutland Regional Airport and world class skiing at Killington, Pico, and Okemo. Whether seeking a luxury farmhouse, country estate, equestrian farm, or four season retreat near major ski destinations, Lanes End Farm delivers an unmatched Green Mountain lifestyle.

Listed by Steve Stettler of Four Seasons Sotheby's Int'l Realty