Very Cool Houses

MLS Number 5111781

• Residential Single Family
• PricePerSqFt 1066.35
• Full Bath 4
• Address 165 High Meadow Road
• Construction Existing

Wandering Moose: a rare heated-pool ski house on High Meadow, on the Stratton winter shuttle route. Rebuilt top to bottom in 2024 with a designer interior, then finished with a heated in-ground pool (2025), hot tub, barrel sauna, Level 2 EV charger and rooftop solar. Open great room with stone wood-burning fireplace and indoor swing, open kitchen and dining, walkout lower level with wet bar and arcade, 4 bedrooms and 4.5 baths. One of the only private heated-pool rentals near Stratton, and it earns like it: $155,716 gross in 2025 and $216,999 trailing 12 months; about $102,000 in confirmed future bookings on the books (9 stays). GOLF-COURSE ESTATE OPPORTUNITY: the seller also owns the adjoining Indian Paint Brush building lots (Lots E-13R & E-14R, 2.48± ac), which abut the Stratton golf course and are listed separately at $500,000. Buy both: live in or rent the Moose while you build your estate next door. Featured on the Destination Channel's Staycation TV program. PORTFOLIO FOR SALE: This property is one of five 42 North properties in Winhall offered individually or together (four turnkey short-term rentals + the Indian Paint Brush building lot; ~$560K combined trailing-12-month gross rental revenue). Ask about package pricing. Listing broker is a principal and beneficial owner of the selling entity. Potential tax advantages for STR buyers (non-passive treatment, cost segregation, bonus depreciation) - consult your tax advisor. Revenue figures are gross rental revenue excluding taxes, before expenses; unaudited; past results do not guarantee future results.

Listed by David Powers of 42 North LP

MLS Number 5108457

• Residential Single Family
• PricePerSqFt 582.9
• Full Bath 1
• Address 226 Hoey Road
• Construction Existing

Historic Rowen Farm is an extraordinary Vermont country property, where the character of a circa-1812 Federal farmhouse has been preserved with exceptional care and paired with refined modern comfort on 77.68 private acres of reclaimed meadow, woodland and mountain views. Original wide-plank floors, exposed beams, doors, period details and four wood-burning fireplaces speak to the home's history, while the updated kitchen, baths and lighting by Teaselwood Designs provide a refined modern counterpoint. Inside, the home unfolds with an easy, welcoming flow. The renovated kitchen opens to breakfast, dining and living spaces, with abundant windows framing the landscape. Porches and decks overlook meadows and ridgeline views. Mudroom, ski/gear room, laundry and outdoor shower support four-season living. The four-bedroom, five-bath layout is equally suited to quiet weekends or a full house. A first-floor ensuite guest room offers privacy, while a library/office leads to a separate wing with bonus room, 3/4 bath and exterior entrance, creating exceptional flexibility and potential for a private first-floor suite. Outside, the land is as compelling as the house. Reclaimed meadows, restored stone walls, woodland trails, brooks and exposed rock ledge create a private setting for hiking, biking and quiet enjoyment. The meadows are maintained by a farmer, preserving the pastoral setting with ease. A barn/garage with loft and lean-to adds character and storage. A comprehensive 2003 restoration by skilled craftsmen included major system upgrades and a full basement excavated beneath the original house. The town road was relocated to create greater setback and privacy. A four-bedroom wastewater system was permitted in 2022 and a new shingle roof completed in 2026. High-speed fiber internet keeps you fully connected. Offered largely furnished with limited personal exclusions. Just 8 miles from Okemo, with convenient access to Woodstock, Killington and the Upper Valley.

Listed by Kim Prins of Four Seasons Sotheby's Int'l Realty

MLS Number 5099132

• Residential Single Family
• PricePerSqFt 603.9
• Full Bath 3
• Address 918 Armstrong Road
• Construction Existing

A rare opportunity to own one of Northern Vermont's premier agricultural properties. This exceptional 427± acre certified organic farm combines a fully operational dairy, diversified agricultural business, and an outstanding custom home with breathtaking views. The dairy operation includes a barn with capacity for approximately 130 head, a fully equipped milk house with bulk tank, pumps, and milking infrastructure, plus radiant floor heat in the milk house bathroom. Four greenhouses, a retail storefront for flowers and vegetables, additional storage buildings, and a heated, insulated 10' x 20' building with outdoor seating create outstanding opportunities for direct-to-consumer sales and agritourism. A separate insulated garage features radiant floor heat, an automotive lift, and workshop. Built in 2008, the quality-crafted home offers over 3,600 sq. ft. of living space with radiant floor heat throughout, cathedral ceilings, a stunning fieldstone fireplace built from stones found on the property, two kitchens with walk-in pantries, a private in-law suite, and an attached two-car garage. The land features productive certified organic hay fields, gravel and sand pits, and an untouched sugarbush with an estimated 5,000-15,000 taps accessed by its own private road separate from the main farm entrance. Enjoy spectacular 180-degree panoramic views of Vermont's Green Mountains, the Canadian mountain ranges, and Jay Peak Ski Resort. Whether you're expanding an agricultural operation, pursuing a diversified farming business, or searching for a legacy estate, this extraordinary property offers unmatched versatility, productivity, and natural beauty in the heart of Vermont's Northeast Kingdom.

Listed by Jeff Como of Rise Realty

MLS Number 5086468

• Residential Single Family
• PricePerSqFt 732.4
• Full Bath 3
• Address 9671 Vt Route 12
• Construction Existing

SPRING HILL FARM- A Storied Vermont Estate with Timeless Appeal. Set amidst the rolling hills of Barnard, Vermont, Spring Hill Farm is a distinguished country estate where historic charm and thoughtful stewardship come together across 207 acres of beautifully maintained landscape. Anchoring the property is a stately brick residence dating to 1795, offering a refined sense of heritage and permanence. A later addition introduces a striking post-and-beam great room, with soaring cathedral ceilings and a fieldstone fireplace that brings warmth, scale, and a sense of rustic elegance to the home's traditional architecture. The result is a sophisticated yet approachable interior, ideal for both intimate gatherings and relaxed everyday living. The grounds are equally compelling. A series of manicured ponds adds visual interest and tranquility, drawing wildlife and reflecting the changing sky. Meandering through the property is a spring-fed stream, which courses gently across the land-its flow punctuated by small waterfalls. The estate also includes a variety of well-preserved outbuildings,including a potting shed, sugar house, and a recently renovated guest cabin nestled high up in a quiet meadow with big views. While the estate enjoys gentle visibility within the surrounding landscape, it offers a unique sense of openness, rhythm, and retreat-perfect for those seeking a connection to land, light, and legacy.

Listed by Susan Hickey of Snyder Donegan Real Estate Group

MLS Number 5089881

• Residential Single Family
• PricePerSqFt 622.87
• Full Bath 4
• Construction Existing
• Bedrooms 4

A rare opportunity for true year-round enjoyment. This is a remarkable chance to own a home on a motorboat lake - with a private dock - just minutes from both the Mount Snow and Hermitage Club ski resorts, hiking, biking, and snowmobile trails, and the charming village of Wilmington, Vermont. Lake Raponda stands apart from the other lakes in the area in one important way: because larger boats tend to head for the public-access Harriman Reservoir on the southern end of Wilmington, Raponda remains a predominantly owner-enjoyed lake. The result is noticeably less boat noise and wake, making it equally wonderful for kayaking, paddleboarding, and peaceful summer mornings on the water. The property sits on a generous, nicely sized parcel with sweeping level lawn space, a private yard with fire pit, ample parking, kayak racks, and a private dock - which transforms into an ice skating destination come winter. Inside the fully remodeled and expanded vintage four-bedroom, four-bath lake house, an open-concept floor plan invites you in with warm wood floors throughout, a living room anchored by a wood-burning stove set in a stone hearth, and a well-appointed kitchen with stainless appliances and island. A relaxing entertainment area with full bath flows into the heated sunroom addition, with expansive windows framing the lake views and opening onto a wraparound deck. A generous mudroom entry handles gear for every season with ease. Upstairs, the primary suite offers wonderful natural light and a luxurious bath, alongside three spacious guest bedrooms, two additional full baths, custom built-in storage, and a lovely office space. The practical upgrades here are just as impressive: efficient mini-split heating and air conditioning, an attached garage for gear storage, an updated septic system, and a private driveway with ample parking. All of it recently completed, the home is completely turnkey - so all you'll have to worry about is downtime, not upkeep.

Listed by Adam Palmiter of Berkley & Veller Greenwood/Dover

MLS Number 5090750

• Residential Single Family
• PricePerSqFt 414.15
• Full Bath 3
• Construction Existing
• Bedrooms 5

Perched on a private hilltop and surrounded by nature, this stunning recently renovated home offers over 141 acres of open and wooded land enrolled in Vermont's Current Use Forestry Program. Thoughtfully designed by Beilman Design, the residence features gracious living spaces filled with natural light and an exceptional floor plan ideal for entertaining. The handsome chef's kitchen is appointed with high-end stainless steel appliances, beautiful countertops, and an exquisite walk-in pantry dedicated to preparation and storage. A spacious guest suite includes two bedrooms and a comfortable sitting area, while the finished lower level offers an additional recreation room with a fireplace. The luxurious primary suite features oversized walk-in closets and a gas fireplace that adds warmth and ambiance. Enjoy the peaceful surroundings from the lovely screened porch or the expansive covered porch overlooking the sweeping lawn and natural landscape. Offering three levels of refined living, the property also includes a large oversized barn for storage, a generator, and a driveway alarm system. Conveniently located with easy access to GMHA, skiing, championship golf, and exceptional fishing, this private retreat presents outstanding potential for a family compound or countryside getaway. Landscaping plans are available.

Listed by Gretchjen Smith of Williamson Group Sothebys Intl. Realty

MLS Number 5088843

• Residential Single Family
• PricePerSqFt 507.05
• Full Bath 3
• Address 719 Walker Hill Road
• Construction Existing

An exquisite, private retreat for artists, writers, nature-lovers, composers or simply as a quiet, serene getaway gathering house on 66 stunningly beautiful acres with stone walls, gardens, patios, open lawns, a beautiful swimming pond, in-ground heated saltwater pool with stone patio, and a breathtakingly beautiful outdoor screened pergola. The residence has five rooms with beds (easily sleeps 10) plus the heated studio building with half-bath, was constructed using reclaimed frames from several historic hand-hewn cape homes built on a modern foundation with modern mechanicals. The home features antique period door hardware, hinges and locks throughout - and hand hewn beams and wall panel boards (some are 2 feet wide). Other features include 12-over-12 wavy glass windows, dutch doors (pantry and study), 3 fireplaces and 2 wood stoves. Other common spaces include a living room, kitchen, formal dining room, sitting room, rec room and two offices and stone wine cellar. Separately a finished/heated “studio” building with a half-bath is now being used as a pottery studio. Excellent mechanicals include buried electrical lines, fiber optic internet, a solar array and an automatic propane backup generator. The mature gardens feature landscape lighting and many varieties of flowers, apple trees and blueberry bushes, attracting bees and hummingbirds. 64 of the 66 acres of land are professionally managed in a Current Land Use program, saving on taxes, with walking trails. And the property abuts the Hawks Hill Forest and trail network. SEE PROPERTY WEBSITE FOR MORE.

Listed by John Snyder of Snyder Donegan Real Estate Group

MLS Number 5107116

• Residential Single Family
• PricePerSqFt 592.92
• Full Bath 1
• Address 1576 Ferry Road
• Construction Existing

Just minutes from Lake Champlain, this exceptional 5 acre Vermont homestead blends historic character with state of the art construction, energy efficiency, and thoughtful design. Built by the owner/builder and talented local craftspeople, the home reflects a passion for quality reclaimed materials and Vermont craftsmanship. At the heart of the home is an extraordinary 1830s Post & Beam frame salvaged from a building at Norwich Academy that was being dismantled. Carefully restored and incorporated into the new construction, the frame brings warmth, character, and a remarkable sense of place. Hickory boards from Shelburne Farms were crafted into the main-level flooring, while 100-year-old Vermont ash boards grace the second level. Vermont marble from Danby was used for the steps. The open first floor is filled with natural light and features a custom kitchen, a stone-fireplace living room, and a sunroom for gathering. Upstairs, the primary suite joins two additional bedrooms and a full bath. The lower level offers a family room, custom designed second kitchen, private ensuite bedroom, and wine room, with walkout access to a welcoming stone patio overlooking the pond. Above the garage is a complete apartment with kitchen, bedroom, and bath. Energy efficiency is seamlessly integrated, with solar providing 100% of the home's electricity needs, complemented by mini-split heat pumps for heating and AC and radiant floor heat. Set on five peaceful acres, this classic Vermont Vernacular home feels naturally rooted in its landscape, private, peaceful, and stately, with architecture and land that seem meant to belong together. Bike to the Charlotte beach or marina, hike Mount Philo or nearby conserved trail systems, enjoy terrific local restaurants, and be on the ski slopes in about an hour. A truly special Vermont property where history, craftsmanship, nature, and modern living come together in one remarkable place.

Listed by Kathleen OBrien and Patrick O'Connell of Four Seasons Sotheby's Int'l Realty

MLS Number 5111700

• Residential Single Family
• PricePerSqFt 621.07
• Full Bath 3
• Address 4945 South Road
• Construction Existing

Located in the heart of the charming hamlet of South Woodstock, the iconic John Arnold Cottle House is widely considered one of Woodstock's finest early residences. Built in 1811, and listed on the National Historic Register, this stately home has been thoughtfully restored, and lovingly stewarded over the years honoring the period detail while creating the perfect unification of antiquity and modern functionality. The bright, spacious rooms flow seamlessly for daily living or entertaining. The impressive Kitchen-Great Room is anchored by a generous brick fireplace, and sweeping 17' cathedral ceiling, and steps out to a private deck overlooking the brook, fields and trail systems beyond. There is a lovely Primary ensuite bedroom, two additional guest rooms and a cozy loft space on the second level. The Kingsley Barn has been transformed into an impeccably appointed two-bedroom lofted guest house with a heated studio space below, and a strong rental history. Cross the brook to the fields and find another barn for storage or animals. Direct access to the GMHA and VAST trail systems for riding, hiking, cross country skiing, and recreation. A short stroll to South Woodstock Store, Kedron Valley Inn and Ransom Tavern. 5 minutes drive to Woodstock Village Green. Furnishings available.

Listed by Danny Kogut of Williamson Group Sothebys Intl. Realty

MLS Number 5085971

• Residential Single Family
• PricePerSqFt 293.64
• Full Bath 3
• Address 1497 Bowman Road
• Construction Existing

Circa 1799 Vermont cape, thoughtfully restored and expanded to over 7,300 finished square feet on 12.5 private acres, minutes to Silver Lake and Woodstock village. Five bedrooms, nine baths, and a layout that balances everyday living with the ability to host. Original materials carry throughout, including wide pine floors, skim-coat plaster walls, hand-carved paneling, and period hardware, giving the house a consistent, grounded feel across old and new spaces. The 24' x 24' kitchen is designed for real use, anchored by an eight-foot Atlantic granite island and equipped with Sub-Zero, Wolf, and DCS appliances, dual Bosch dishwashers, and a walk-in pantry with tiled counters, extensive storage, half bath, and laundry. It opens to a sitting room with a wood-burning fireplace and full-height paneling. A separate wet bar includes a wine cooler, ice maker, and copper sink. Living spaces include a formal dining room, library with built-ins, study with J?tul woodstove, a 22' sunroom with stone fireplace and custom windows, and a 34' screened porch with fir floors and painted wainscot ceiling. The bedroom layout offers flexibility and privacy, with a first-floor en-suite for guests and a primary suite with fireplace, private deck, dressing room, and bath with soaking tub and tiled shower. Two additional en-suite bedrooms, along with a large family room, office, and second laundry, are located upstairs. The grounds feature three ponds, fieldstone terraces and walkways, brick patios, perennial gardens, raised beds, and an apple orchard, along with tucked-away seating areas. Outbuildings include a heated three-bay attached garage and a separate 1,465 SF heated car barn with capacity for up to ten vehicles (four on lifts). Above, a one-bedroom apartment with full kitchen and bath is currently used as a short-term rental. Additional structures include a historic bank barn and chicken coop. 15kW whole-house generator, fiber internet, and updated systems throughout.

Listed by Richard Higgerson of Higgerson & Company

MLS Number 5095153

• Residential Single Family
• PricePerSqFt 493.42
• Full Bath 4
• Address 121 Fannie Hill Road
• Construction Existing

Owner will consider offers. Stunning contemporary chalet completely renovated in 2016 and located adjacent to the base of the Hermitage Club private ski resort. This gorgeous home sits on a private lot with direct snowmobile trail access, easy access to the ski trails, and direct to the clubhouse. Just a short drive into the village of Wilmington and the area's tremendous lakes. Thanks to the complete overhaul and meticulous maintenance, this home is turn key for immediate enjoyment, with features including an open concept design, large great room with vaulting ceilings and exposed beams, a stone hearth with wood burning fireplace, upscale country kitchen with stainless appliances and granite counters, a secondary wet bar area, sizeable dining table for all your guests, wood floors throughout, a main floor primary suite with walk-in closets and large tiled bath, dual rustic bunk rooms, a lower level guest suite, 7 spacious bedrooms in total, a large family room for great separate entertaining space, movies, and games, as well as an adjacent tv area, and a tremendous mudroom with built in cubbies for all your gear after a day on the trails. There is also a large covered front porch to keep the snow at bay with wood storage, massive hot tub, fenced in dog area, generator, tremendous parking, and nice lawn space without being much to maintain. With proximity like this and creature comforts from home, this makes for a great ski home, as well as a welcome respite from the metropolitan bustle year round.

Listed by Adam Palmiter of Berkley & Veller Greenwood/Dover