Windsor County

MLS Number 5066208

• Residential Single Family
• Full Bath 4
• Address 650 Francis Road
• Bedrooms 2
• Bathroom 7

Set on 400+/- acres in Barnard, Vermont, Monsalvat Farm is a legacy estate where rolling pastures, stone walls, forests, and mountain views reflect the state's timeless character. Settled in 1793, the land carries generations of stewardship, elevated by one of the finest residences in the country-an architectural masterpiece complemented by historic and companion structures that are carefully integrated into the landscape with grace and permanence. Buildings include: the primary residence called "the Sanctuary" with 12-sided cathedral great room, primary bedroom suite with 2 bathrooms, one with fireplace, 7 additional fireplaces including one in the guest suite, wine cellar, music media room known as "the Cabin" and a dining room with stunning overhead sculpture positioned as an upside down tree with nested lights; a 2 bedroom 2 1/2 bathroom charming stone guest house, known as "Gilbert's Cottage;" a restored farmhouse with 4 separate apartments each with 1 bedroom and a full bathroom; a 1 bedroom 1 bathroom cabin called "the Lodge"; a restored historic barn with attached 5 stall stable, heated tack room and farm managers office with bathroom and shower; a Gazebo with fireplace, half bathroom and shower, a detached 3-bay garage, an equipment barn, a cattle barn and a sugar house. With a private gated entrance and bridge, built to highway specifications, over a large pond, a private FAA approved heliport, orchard, fields and miles of trails, Monsalvat Farm is truly magical.

Listed by Christopher Lang of Bravynia

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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MLS Number 5066210

• Residential Single Family
• Full Bath 5
• Address 355 Greene Road
• Bedrooms 7
• Bathroom 10

Star Hill Farm is completely private, hidden on a hillside with pastoral and mountain views in the heart of South Woodstock. From the valley floor to the top of Meetinghouse Hill, you will be inspired by its beauty, a mesmerizing 183.7+/- acre oasis over gorgeous terrain with fields, woodlands, trails, and stone walls. The historic 2-bedroom guest house and party barn are fully restored, and located next to the swimming pond. The main residence, completed in 2010, consists of the center core with porch - for cooking, gathering and entertaining; the owner's quarters with a 2nd floor suite and 2 bedrooms below; the guest wing with 3 first-level bedrooms, second-floor game room and adjacent 8-bed bunk room and a 4-story octagon with wine cellar at the base and flexible multi-use spaces above. All 7 bedrooms are ensuite plus 3 powder rooms. The attached gambrel barn is a professional grade gymnasium with 6-car heated garage underneath. The interior is like a grand lodge in the American West while the exterior with shingles and gambrel barn is traditional New England. The systems and mechanicals are all commercial grade. The finishes and craftsmanship are consistently superb. The atmosphere is relaxed and fun. As a complete fully furnished package, each and every attribute at Star Hill Farm - the location, land, exposure, privacy, views, guest house, barn, pond, residence and gymnasium- is exceptional, creating one of the finest properties in Vermont.

Listed by Christopher Lang of Bravynia

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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MLS Number 5044620

• Residential Single Family
• Full Bath 4
• Address 412 Skyland Lane
• Bedrooms 4
• Bathroom 5

Once the site of an 1850s homestead and now reimagined for 21st-century living, Skyland Farm is a private retreat on 63 acres. Mineral springs, glass architecture, and extraordinary views define this rare legacy property, just minutes from the village of Woodstock and with direct access to the trails of Mount Peg. Found at the end of a quiet lane, sweeping vistas of the Green Mountains and Killington are viewed from nearly every room. Finished in 2024, this timber frame home channels modern farmhouse warmth with a clean, contemporary edge.The wall-to-wall glass in both gables frames the surrounding landscape like living artwork, while inside, 24-foot ceilings, radiant heat, A/C, and a sauna provide everyday indulgence and embrace. At the heart of the home is a chef's kitchen with Marinace granite, Wolf and SubZero appliances, and reclaimed hickory floors. Gently sloping meadows invite sledding in winter and lead to the barns below including a 6-stall stable, indoor riding arena with heated viewing area, and a spacious barn perfect for guest quarters, workshop or a car collection. Set between the twin gables, an elevated courtyard with a heated Soake pool creates a seamless indoor-outdoor connection, ideal for sunset reflections in the summer and stargazing in the winter. A 3-bay garage, and stream complete this offering. GMHA, and premier skiing nearby.

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

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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MLS Number 5089158

• Residential Single Family
• Full Bath 3
• Address 2358 Long Hill Road
• Bedrooms 5
• Bathroom 4

Framed by groves of mature birch trees, a winding drive descends into a private valley surrounded by pastures, apple orchards, a spring-fed pond, and sweeping mountain views, arriving at Birch Tree Farm. Spanning more than 465 acres, this extraordinary Vermont retreat offers an immersive four-season lifestyle -- from pressing fresh cider from the orchard and tapping maple trees for syrup to harvesting honey and gathering fresh eggs for breakfast. Miles of trails traverse varied terrain, including the summit of Old Baldy Mountain (2,409 feet). The retreat includes a lodge-style residence, a modern barn, and several ancillary farm buildings. The wood and stone lodge-style home carries a relaxed mountain vibe. Thoughtfully renovated in 2026, the interiors balance scale and warmth: exposed beams, a cathedral ceiling in the great room, and a substantial wood-burning stone fireplace anchor the space, while floor-to-ceiling windows draw in sweeping views of the mountains. The wrap-around deck takes in an infinity pool, hot tub, and stocked pond. In spring, wild lupine carpet the meadow; in autumn, the apple orchard comes into its own. Landscape design by Shep Butler includes 10' hydrangea bushes, perennials gardens, stone walls and a walled vegetable garden. The three-level bank barn, designed by award winning Boston architect John MacDonald and built by Housewright Construction, offers one of the finest barns in area with 7 box stalls, a farm manager's office/tack room, and a versatile upper level for entertaining, recreation, and movie night as well as accommodating an overflow of guests. Nine fenced pastures, run-in sheds, chicken coop, apiary, and direct access to GMHA's trail network support an exceptional equestrian and recreational lifestyle. 157 acres conserved by VLT. 3.1 miles from GMHA, 3.8 miles from South Woodstock Country Store and Post Office, Less than a half hour from Killington, 2.5 hours from Boston.

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

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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MLS Number 5089880

• Residential Single Family
• Full Bath 1
• Bedrooms 8
• Bathroom 8
• Square Feet 10,062

Escape to Moosewalk Lane. This ultimate family compound is a fully furnished and equipped rural retreat in Andover, Vermont. Set on 384 acres rising to 2,200 feet, the tract blends seclusion and timeless craftsmanship, with miles of private trails for winter sports, horseback riding and recreational vehicles, all threading through open meadows, historic stone walls, and woodlands, with direct access to the VAST snowmobile system. The 10,062 sq ft timber frame main house is anchored by a soaring two story great room with a dramatic stone fireplace and an open chef's kitchen featuring double appliances, a Viking 60 inch cooktop and a wood fired pizza oven. A cozy loft and a library provide serene reading nooks. The main level includes a distinctive 2 bed, 2 bath primary suite, plus six additional bedrooms and five baths for family and guests. Onsite amenities include a home gym, media and game room, outdoor art installations, paved driveways and six garage bays. The multi building compound consists of a guesthouse with private office, a heated writer's cabin with panoramic view of the Connecticut River Valley, an equipment barn and woodshed - everything needed for comfortable year round living, family retreats, or events. Enjoy hiking, snowshoeing, wildlife viewing and a gravity fed 50 tap maple syrup operation all in a private setting to share with family and friends. Watch the award nominated video tour to see why Moosewalk Lane delivers the quintessential Vermont experience.

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

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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MLS Number 5047809

• Residential Single Family
• Full Bath 6
• Address 476 Salt Ash Road
• Bedrooms 5
• Bathroom 6

Serena Lodge was inspired by the legendary William Rockefeller estate in the Adirondacks, known as The Point, and thoughtfully designed to reflect its inviting look and warm, rustic elegance. This 9,000+ square foot residence sits atop a knoll beside a lively creek with small waterfalls, creating a peaceful, natural soundtrack. The Great Room is the centerpiece of the home, with a soaring stone fireplace, floor-to-ceiling windows, two sitting areas, and an open kitchen framed by thick granite counters. Just outside, a terrace with built-in barbecue and stairs leads down to the creekside. The east wing features a serene primary suite with a fireplace, sitting area, and private balcony. The west wing includes four en-suite bedrooms and a family room. A loft above offers space for an office, artist studio, or reading nook. The lower level Adirondack Room (25' x 38') is perfect for games and movies, with flexible sleeping options, plus a bonus room, full bath and a woodshop that doubles as garage space. Fully air-conditioned with high-speed internet and a backup generator, Serena Lodge offers comfort and convenience year-round. Located in the Hawk community and serviced by Hawk Property Management, it is just a short drive to Okemo and Killington. Whether you seek solitude or connection, adventure or rest, this stunning home offers it all.

Listed by Debra Staniscia of Four Seasons Sotheby's Int'l Realty

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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MLS Number 5076511

• Residential Single Family
• Full Bath 4
• Address 924 Okemo Ridge Road
• Bedrooms 7
• Bathroom 7

Perched in Solitude, one of Okemo’s most sought-after on-mountain neighborhoods, 924 Okemo Ridge Road offers exceptional slope access, sweeping long-range views, and the scale to comfortably bring generations together under one roof. With 7 bedrooms and 6.5 bathrooms, this is a true ski homedesigned for gathering, hosting, and making memories year after year. The home delivers classic ski lodge vibes with expansive living spaces, walls of glass framing the mountain views, and seamless indoor-outdoor flow. Slopeside outdoor living is a standout feature, with a maintenance-free deck system, covered hot tub area, heated stone patio, and an exterior fireplace built for long aprs-ski afternoons. Ski home, light the fire, and settle in. Inside, the kitchen was fully renovated in 2021 and anchors the main living space with new cabinetry, granite countertops, a reconfigured island, a dedicated coffee and bar area, a pizza oven, and thoughtfully integrated appliancesperfect for feeding a crowd. Multiple gathering zones include a theater room, game room, wine room, sauna, and a well-designed boot room that keeps ski days organized. Significant mechanical and system upgrades add peace of mind. Other great upgrades include Tesla charging and whole-home Sonos. The result is a turnkey, well-maintained slopeside retreat that balances comfort, durability, and funwhether it’s a holiday weekend with the whole family or a quiet midweek powder day. Located just steps from some of the best skiing on the mountain at Okemo Mountain Resort, this Solitude home stands apart for its access, views, and ability to live large on the mountain. Visit the Okemo real estate community today. Taxes are based on current town assessment. ROFR

Listed by Katherine Burns of William Raveis Real Estate Vermont Properties

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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MLS Number 5063616

• Residential Single Family
• Full Bath 1
• Village Ludlow
• Bedrooms 4
• Bathroom 2

MAJOR 7 FIGURE PRICE REDUCTION! Your Vermont Mountain Retreat Awaits Discover 127 acres of pure Vermont beauty at the foot of Okemo Mountain, just 2 minutes from downtown Ludlow. This rare property offers expansive meadows, forested trails, and panoramic views of Okemo, Mount Ascutney and beyond. Enjoy direct access to cross country skiing, hiking, snowshoeing, the VAST trail system, and year-round outdoor adventure. The updated finished 3150 square ft 4 bedroom house with bonus rooms and barn is move-in ready. Perfect for your full-time home, vacation getaway, or guest house while you build your dream retreat elsewhere on the property. This is a once-in-a-lifetime chance to own one of Ludlow's last large undeveloped parcels. Preliminary engineering, structural work and surveys are complete, making this a perfect candidate for multi-phased development. Owner financing available. Create a private estate, build a family compound, or develop a ski-centric neighborhood of townhomes, chalets, or even commercial lodging.

Listed by Frank Provance and Sean Attebury of Diamond Realty

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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MLS Number 5092980

• Residential Single Family
• Full Bath 2
• Address 112 Snowbridge Road
• Bedrooms 5
• Bathroom 6

Experience the pinnacle of slopeside luxury in this extraordinary ski-in/ski-out mountain retreat, positioned between Okemo's coveted Ledges and Sachem Ski Trails. Masterfully crafted across three impeccable levels, this exceptional residence showcases timeless mountain elegance, superior craftsmanship, and refined finishes throughout. Designed for effortless living and grand-scale entertaining, the home features two dedicated mudrooms with direct trail access, allowing you to step right onto the slopes. Lighted stairways connect generous living spaces that blend comfort and sophistication at every turn. The main level serves as the family gathering space, offering an inviting great room anchored by a stunning stone fireplace, a recreation room with billiards, and a chef's kitchen designed to impress. Outfitted with premium appliances, custom cabinetry, island seating, and an oversized beverage refrigerator, the kitchen is perfectly suited for both intimate gatherings and aprs-ski celebrations. After a day on the mountain, retreat to the lower-level family room and relax by the fire, rejuvenate in one of two spacious indoor saunas, or escape to private lofts and bonus rooms ideal for a home office, reading nook, or additional guest accommodations. Outside, an extensive deck invites year-round enjoyment with ample space for outdoor dining, grilling, and entertaining. Unwind beneath the stars in the brand-new hot tub while taking in panoramic views of the ski slopes and surrounding mountains. From the deck and interior living spaces, enjoy a front-row seat to the chairlift and the beauty of the landscape. Completing this remarkable offering is parking for more than ten vehicles, including a spacious two-car attached garage with abundant storage for all your mountain gear. A rare opportunity to own one of Okemo's premiere slopeside residences, where luxury, convenience, and breathtaking mountain views converge to create the ultimate alpine lifestyle.

Listed by Elissa Scully of Mary W. Davis Realtor & Assoc., Inc.

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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MLS Number 5080290

• Residential Single Family
• Full Bath 5
• Address 5893 Stage Road
• Bedrooms 7
• Bathroom 9

Set on 54 exceptionally private acres, Long Way Hill is a a quietly luxurious Vermont country retreat overlooking a half-acre pond, with sweeping lawns, gardens, fields, and woodland trails. It is located minutes from Silver Lake and Twin Farms, and 15 minutes from Woodstock. Designed by David Beilman and built by Savelberg Construction in 2006, the home is defined by its high craftsmanship--beautifully detailed, high ceilings, and informed by the understated elegance of New England architecture. The home is both gracious and comfortable, created for gathering. A dramatic great room with vaulted ceiling and floor-to-ceiling stone fireplace anchors the main level, while a well-appointed gourmet kitchen with eat-in dining, butler's pantry, and generous workspace invites connection and ease. A spacious living room with a fireplace and dining-sitting area, and a private library/office add warmth and versatility. Five en suite bedrooms, thoughtfully arranged over the second and third floors, offer privacy and separation, complemented by a four-story elevator. The lower level offers a game-theatre room, fitness space with sauna, and additional recreation areas. A separate two-bedroom apartment with full kitchen and laundry accommodates guests. Outdoors, perennial and wildflower gardens unfold from spring through fall, surrounding open porches, a screened porch, and a hot tub overlooking the pond. Wildlife, birdsong, and star-filled skies define the setting. Top-tier mechanical systems, central AC, whole-house generator, and high-speed fiber connectivity. The property is meticulously maintained.

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

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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