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luxury houses with pool for sale Windsor County, United States

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House with pool Woodstock (United States)

Just 2 miles from Woodstock Village, this gracious brick Cape on 6 open acres offers the perfect blend of privacy, comfort, and classic Vermont charm. Thoughtfully expanded and beautifully maintained, the home features a chef’s kitchen that opens seamlessly to a spacious gathering room designed for entertaining and everyday living. Multiple fireplaces—including a wood-burning and gas-ready—add warmth and character throughout the home. The flexible floor plan includes 3–4bedrooms, highlighted by an upstairs bedroom with its own fireplace, plus a private guest suite or office above the garage—ideal for visitors, remote work, or creative space. Outdoor living is equally exceptional. Enjoy a covered porch, sunny patio, dedicated garden space, apiary, and an in-ground pool with heat hookup for extended seasonal enjoyment. More than 5 acres of invisible fencing allow pets to roam freely across the open landscape. Perfectly positioned for year-round recreation, the property sits adjacent to the site of America’s first ski tow and offers easy access to Saskadena Six, Killington, and outstanding winter activities throughout the region. A standout feature is the heated and plumbed two-story barn/workshop with its own vehicle bay—offering endless possibilities as a media or game room, studio, workshop, fitness space, or future guest quarters. With easy access to I-89 and the Upper Valley, this rare offering combines acreage, versatility, and close proximity to one of New England’s most iconic villages.

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$1,395,000
339m²
5bedrooms
4bathrooms
land 2.5ha

By Williamson Group Sotheby's International Realty

30
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House with garden and terrace Barnard (United States)

AUCTION: Bidder registration deadline: 6 October. Starting bids expected between $1.25M-$2.25M. Set on twelve pastoral acres in the storybook town of Barnard, Vermont, Highland Glen captures New England charm at its finest. A red barn, mature apple orchard, and towering sugar maples greet arrival, while stone walls and wooded paths wind past willow trees, a stream, trout-stocked ponds, a waterfall, and fountains. A swim spa and expansive decks invite alfresco entertaining beneath open sky. Inside, a chef's kitchen anchors the home, complemented by a four-season lodge room with a river rock fireplace, an upstairs tavern with a full bar, a wine cellar, sauna, and billiards area. Recently renovated and meticulously maintained, Highland Glen stands as a rare Vermont sanctuary, equal parts tranquil retreat and lively gathering place, moments from Silver Lake and the Barnard General Store.

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$3,895,000
755m²
5bedrooms
3bathrooms

By Annonceur International

50
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House with pool Barnard (United States)

Honey Hill Farm is a rare and distinguished Vermont estate encompassing 264.4 extraordinary acres of pastoral beauty, panoramic mountain views, and an unrivaled network of private trails, with an additional contiguous 42.6-acre parcel available for purchase. More than a luxury property, Honey Hill offers the experience of a private park, with nearly 10 miles of trails winding through forests, open meadows, cascading brooks, waterfalls, and around a spring-fed pond. Whether for hiking, cross-country skiing, horseback riding, mountain biking, or quiet exploration, the land offers a seldom-found level of privacy and recreation. The main residence has been masterfully reimagined through a full-scale renovation, blending timeless craftsmanship with modern luxury. At its heart lies an expansive gourmet kitchen with custom marble finishes and bespoke detailing. A four-season room with floor-to-ceiling glass doors dissolves the boundary between indoors and the breathtaking landscape beyond. Formal living spaces flow seamlessly into a richly appointed bar and billiards room and onward to a spectacular library, where exquisite millwork and tailored lighting create an atmosphere of quiet grandeur. Each bedroom suite is generously scaled and paired with indulgent ensuite baths. An extraordinary spa offers infrared and salt therapies and opens directly to a heated pool surrounded by nature. Modern systems ensure comfort and security, including radiant heat, central air, water purification, and a whole-house generator. The iconic red barn has been fully restored, with upper-level entertaining and fitness space and a beautifully appointed guest apartment below. Offered as a fully curated turnkey estate, Honey Hill includes exquisite custom furnishings thoughtfully selected to complement the home and setting, allowing for immediate enjoyment. Privately sited behind gates and shown by appointment only, Honey Hill Farm is a world unto itself and legacy in the making.

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$12,950,000
820m²
5bedrooms
4bathrooms
land 107ha

By Williamson Group Sotheby's International Realty

50
Video

House with pool and garden Weathersfield (United States)

High Shelter Farm offers the ultimate Vermont lifestyle on 64.64 extraordinary acres of fields, forests, and breathtaking views.. Direct access to Vermont's VAST trail network makes this a true outdoor enthusiast's paradise.The meticulously maintained 4,500+ sq. ft. home is perfectly positioned to capture spectacular views of Mount Ascutney and the White Mountains of New Hampshire. Floor to ceiling windows fill the living room with natural light and showcase the surrounding landscape. Recent updates include, newly painted interior, beautifully renovated bathrooms and refinished hardwood floors. The home offers four bedrooms, a spacious eat in kitchen, formal dining room, and inviting gathering spaces throughout. An owned, fully paid for net metered solar system transfers with the property, helping power the home while enhancing energy efficiency and long term value.A permitted one bedroom accessory apartment with private entrance and patio provides flexibility for guests, extended family, or rental income. Outside, an inground gunite pool and gazebo create the perfect setting for summer entertaining. The recently built barn, now an exceptional event space, has hosted family weddings and gatherings while honoring the property's agricultural heritage.Ideally located near Hanover, Dartmouth, Woodstock, Crown Point Country Club, area ski resorts, Hartness State Airport, and the Upper Valley, High Shelter Farm is a rare opportunity to own a property that truly embodies the best of Vermont living where recreation, sustainability, privacy, and natural beauty come together in one extraordinary setting.Available with more acreage see MLS 5096178.

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$1,200,000
4bedrooms
5bathrooms
land 0ha

By Four Seasons Sotheby's International Realty

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