Homes with 50+ Acres

MLS Number 5015744

• Residential Single Family
• Full Bath 7
• Address 370 Fischer Lane
• Construction Existing
• Bedrooms 6

Accessible, but miles from the everyday. Camp Endo's mountain kingdom is minutes from Stratton Mtn. with a 21st century take on a mountain timberframe home, and 417+/- acres threaded with trails and ridgelines. Ski your own glades and rip the eight miles of custom-designed mountain biking terrain, or just pause to enjoy the vast views. The house reimagines a rustic lodge with classic wood, bark and stone detailing combined with complete comfort, great light and welcoming spaces. The property was featured in the book Rustic Living by Ralph Kylloe as one of the great rustic style homes in the U.S. The 13,393-square-foot home has an open floor plan, massive stone great room fireplace, chef's kitchen and 6 bedrooms en suite, each with magnificent mountain views. Off the kitchen and great room is a screened-in porch and large deck with an outdoor stone fireplace to soak in the panoramic southerly green mountain views. Smaller gathering spaces include a corner office, gym/spa, meditation room and 22-seat home theater. Camp Endo's extensive trail network provides a daily dose of rugged, natural beauty for mountain biking, walking or snow shoeing and playful options include a paintball course and a six-foot square chessboard. The adjacent barn houses a fully appointed 2 bedroom guest suite, 3-bay garage and half-basketball court with surround sound. Next to the apple orchard is a large swimming pond with views of Stratton Mtn. The property has renewable solar and wind energy.

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

MLS Number 5015743

• Residential Single Family
• Full Bath 1
• Construction Existing
• Bedrooms 8
• Bathroom 8

A magnificent 10,062 SF family compound. Custom built, it comes fully furnished and equipped for immediate occupancy, featuring 7BR, 8BA, a separate 1BR guesthouse and office, a furnished and heated writers cabin overlooking the Connecticut River Valley, and an equipment barn, all situated on 384 acres of pristine hardwood forest, accessed by an 1800' paved driveway. Anchored by miles of woodland trails and located in Andover, Vermont, the offering includes outdoor sculpture and artwork, historic rock walls, open fields and building ruins from early settlers, along with direct access to the VAST trail system for winter trail riding. The main house features a soaring 2-story fireplace, post and beam timber frame construction, and a chef's kitchen with double appliances, Viking 60” cooktop and wood-fired interior pizza oven, while a reading loft and library add a calming vibe to the outdoor view. The primary suite has a 2BR, 2BA configuration on the main floor with 5 additional bedrooms with en suite baths. There are 6 garage bays supplied with commercial sinks, a 21' x 35' open design gym and exercise suite, and a media room with custom pool table and walkout to the ground floor. Designed for 4-season recreation, privacy and small batch maple syrup production, the hardwood forest, mountain trails, open fields, and additional access from another town road offer unlimited possibilities for the discerning buyer looking for a lifestyle in Vermont's iconic Green Mountains.

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

MLS Number 5005058

• Residential Single Family
• Full Bath 5
• Address 454 Mountain Road
• Construction Existing
• Bedrooms 6

Luxurious 141 acre mountaintop retreat within Stratton Mountain Resort, stunning views of Stratton, Mt Snow, and Bromley. This architectural masterpiece blends comfort and elegance, with multi level interiors harmonizing living areas and en suite bedrooms. Inspired by the graceful arcs of skiing turns, the design features a dramatic entryway leading to a spacious living room and library. An 18-foot stone fireplace and expansive windows flood the space with natural light and breathtaking views. The entry leads to a gourmet kitchen with a large eat-in dining and a formal dining room, perfect for entertaining. The home boasts 6 en suite bedrooms, an expansive primary suite with an office, two custom walk-in closets and a cedar closet. A custom-built bunk room with locker-style cubbies adds playful sophistication. A light-filled hallway connects the upper and lower levels, linking bedrooms, a home theatre, and living areas, enhancing the open and airy feel. Additional amenities include a golf simulator and a movie theatre. Outdoors enjoy mountain views, perennial gardens, natural stone accents, and a bluestone walkways. In warmer months, luxuriate in the gunite pool and hot tub while soaking in views. A gym in the detached three-car garage is perfect for workouts. Tennis and pickleball courts offer additional outdoor activities. This property is a sanctuary where architectural elegance meets mountain tranquility. Discover the epitome of luxury at this stunning mountain retreat.

Listed by Lisa Sullivan of Four Seasons Sotheby's Int'l Realty

MLS Number 5011880

• Residential Single Family
• Full Bath 1
• Address 527 Benson Road
• Construction Existing
• Bedrooms 5

Boorn Brook Farm combines the rich character of history and the comfort of contemporary living with complete privacy. Established in the late 1700s, the estate near Manchester Center offers stunning views of the Mt. Equinox and the Taconic Range. Surrounded by the Green Mountain National Forest, it creates a peaceful haven that balances the old and the new. For over 50 years, Marion Gould Pleissner lived at the Plaza in New York City and summered here while her husband, celebrated artist Ogden Pleissner, used the barn as his studio-his works now hang at the Met, Shelburne Museum and in private collections. The 1790s farmhouse and 1820s barn underwent extensive renovations by Boston architects Judge, Skelton, Smith. The farmhouse was thoughtfully restored, while the barn was transformed into two living spaces. Modern updates, including new utilities and underground infrastructure, were discreetly integrated to preserve the pristine vistas. The Great Room of the Barn have seen many lively gatherings over the years. Today, this multi-generational sanctuary remains a tranquil retreat, bordered by Bourn Brook and encircled by the GMNF's Lye Brook Wilderness Area. The property retains its pastoral allure with goats grazing the fields and timeless pleasures like fly fishing, hiking and swimming. Currently serving as a family compound and wedding venue, the property holds an Act 250 permit for up to 43 cabins. For more details, refer to the commercial listing.

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

MLS Number 5011616

• Commercial
• Village Bennington
• Address 507 Benson Road
• Year Built 1890
• Square Feet 5,445

Rustic simplicity. Luxury retreat. Complete privacy and surrounded by National Forest. Green Mountain Resort at Boorn Brook Farm in Manchester Center is shovel ready. All town zoning and Vermont State Act 250 permits are in place, along with all other required environmental and state approvals, for developing a 46-cabin, four-season retreat on 53+acres. With big views of Mt. Equinox and the Taconic Range and sited at the end of Benson Road, Green Mountain Resort at Boorn Brook Farm is within the Rural Agricultural zoning district, with a portion in the Forest Conservation zoning district. Just 2 miles from the center of Manchester, the property is bordered to the north by Bourn Brook and surrounded on the east, south, and west by the Green Mountain National Forest and Lye Brook Wilderness. Included in the sale are a C.1790 farmhouse and C.1820 barn, which have been extensively renovated, trout pond, meadows, woodlands threaded with trails and tennis/pickle ball court. Refer to the residential listing for more information. A significant amount of the required infrastructure and project components are already in place. Envisioned as an eco-friendly, experiential retreat, the project aims to provide guests with an opportunity to connect with nature and the community through immersive and educational experiences. Green Mountain Resort at Boorn Brook Farm is also perfect for hosting weddings, corporate retreats, cultural events, and business conferences.

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

MLS Number 5005964

• Land
• Address 00 Vt Route 11
• Acreage 227
• Area VT-Bennington
• Utilities None

Seize a once-in-a-lifetime opportunity with this stunning 227 +/- acre legacy property, nestled against the natural backdrop of the National Forest and Bromley Mountain. This expansive parcel offers development potential, making it the perfect canvas for creating a private compound or a luxury mountain retreat. Imagine waking up to breathtaking sunrise views of Stratton and the Green Mountain National Forest, with outdoor adventures right at your doorstep. The property's generous size provides ample space for multiple dwellings and private amenities, ensuring privacy and exclusivity. Whether you envision a serene family estate or a secluded sanctuary, this property is the ideal setting to bring your vision to life. Embrace the tranquility and splendor of mountain living; one could even ski back to the property from Bromley. Enjoy all that Southern Vermont has for you, while being just a short distance from, Magic, Stratton and Manchester. Don't miss out on this rare chance to own a piece of paradise that can be cherished for generations to come.

Listed by Kevin Moran of Four Seasons Sotheby's Int'l Realty

MLS Number 4972272

• Residential Single Family
• Full Bath 1
• Address 662 Howe Farm Road
• Construction Existing
• Bedrooms 4

Discover this renovated timber frame home nestled on 366 acres of private land. Offering a seamless blend of historic character and modern comfort, this 4 bedroom plus office, 4 and a half bathroom home showcases attention to detail. The gourmet kitchen, inviting living spaces, bonus game room and home gym are complemented by a sunlit dining space with a greenhouse sunroom, adding a touch of nature to your daily life. Multiple bedrooms give everyone in your party a private space to relax after a long day exploring the outdoors. Step outside to witness dramatic views of the rolling hills that surround the property. A tranquil pond with gazebo graces the landscape. A well-appointed barn with 5 stalls and a paddock caters to equestrian enthusiasts. Miles of trails crisscross the property, providing endless opportunities for outdoor activities. This property is subject to an Act 250 permit and enrolled in Vermont Current Use Program, securing its natural beauty for the future. Whether you are relaxing on the porch or hosting gatherings in the spacious bonus room, this estate balances seclusion and convenience. Situated in bucolic Jamaica, it is 20 minutes from Stratton and 25 minutes from Mount Snow. Let this be your four season retreat, close to the mountains in the winter, swimming holes in the summer, and stunning views all year round!

Listed by Andie Fusco and Tara van de Velde of Four Seasons Sotheby's Int'l Realty

MLS Number 4990472

• Land
• Address 0 Howard Hill Road
• Acreage 297.52
• Area VT-Windsor
• PricePerSqFt 6720.56

You've got creative visions - We've got your canvas Immerse yourself in the tranquility of nature as you explore the mature maples,ponds, meadows, stone walls and vista views of this remarkable 200.27-acre property. Whether you're seeking a private retreat, an investment opportunity, or your dream home, this property offers the perfect blend of natural beauty, seclusion, and potential. The possibilities are endless. Don't miss your chanceto own a piece of Vermont's pristine landscape. Schedule a viewing today and let your imagination take flight!

Listed by Frank Provance of Diamond Realty

MLS Number 4971327

• Residential Single Family
• Full Bath 6
• Address 207 Brooks Lane
• Construction Existing
• Bedrooms 9

This extraordinary, fully furnished property boasts an abundance of amenities and natural splendor. Revel in the awe-inspiring views and the tranquil swimming pond spread across these extensive 69 acres. Delight in the winding trails that lead to 1,235 feet of pristine West River frontage, providing year-round outdoor activities for all. With three distinct residences and a charming cabin, it offers ample space for everyone to convene while relishing their individual, private retreats. The main house, steeped in history dating back to 1820, is a delightful 3-bedroom brick farmhouse showcasing a generous 45-foot-long great room that seamlessly extends to a covered patio adorned with an awning, a idyllic setting for outdoor gatherings. The newly renovated kitchen, with granite countertops, serves as the heart of the home, combining modern elegance with timeless charm. The guest cottage features an additional three bedrooms, a cozy living room, and a well-appointed kitchen with an adjoining dining area. Adjacent to the guest cottage, a spa facility awaits, boasting a ground-level private gym, sauna, and an outdoor hot tub. Ascend to the second floor to discover two bedrooms, each with a private bathroom and a shared balcony. Nestled at the property's edge, overlooking the serene swimming pond with a beach, is a rustic cabin complete with a welcoming wood-burning stove and a lofted sleeping area. Ideally suited as a family compound, this retreat offers both separation and privacy

Listed by Timothy Apps of Four Seasons Sotheby's Int'l Realty

MLS Number 4990111

• Land
• Address Howard Hill Road
• Acreage 111
• Area VT-Windsor
• PricePerSqFt 10810.81

You've got creative visions - We've got your canvas Immerse yourself in the tranquility of nature as you explore the mature maples, ponds, meadows, stone walls and vista views of this remarkable property. Whether you're seeking a private retreat, an investment opportunity, or your dream home, this property offers the perfect blend of natural beauty, seclusion, and potential. The possibilities are endless. Don't miss your chance to own a piece of Vermont's pristine landscape. Schedule a viewing today and let your imagination take flight!

Listed by Frank Provance of Diamond Realty

MLS Number 5021448

• Land
• Address West Hill Road
• Acreage 51.93
• Area VT-Windham
• Utilities None

The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 5 is 51.93 acres and is located at the top of the subdivision. This parcel is very unique, and rarely do pieces of land like this come onto the market. Lot 5 has a private driveway that begins at Lot 4. The parcel encompasses the entire north side of the subdivision, from the bottom of the hill all the way up the access road. The views from the clearing at the top of the driveway are to the west toward Bromley Mountain, but there are also big views in the other direction looking southeast. There would be several spots to build on this parcel, but the top of the hill seems like the place to be with the ability to have unobstructed views from your new home.

Listed by Thom Milke of Fountains Land Inc.

MLS Number 4982154

• Land
• Village Ludlow
• Address Macginnis Drive
• Acreage 74.2
• Area VT-Windsor

The Soapstone Babbling Brook flows through this wonderful property with stone walls, soft and hard wood trees, all within 1.5 miles to downtown Ludlow and Okemo Mountain. Developers take notice of the beautiful long distant VIEWS to OKEMO and beyond from several different locations on the property, with the potential to connect to village sewer. The perfect playground for any outdoor enthusiasts, fishing, hunting, x-country skiing, snowshoeing, four wheelin', dirt bikin' and the list goes on. On the VAST trail, with access to Maine, even Canada if your up for a road/trail trip. The perfect spot for someone who wants to be in the woods with the conveniences of town just down the road. There aren't to many of these large parcels left with this proximity to the village. A MUST SEE PROPERTY TO SEE THE POTENTIAL!

Listed by Frank Provance of Diamond Realty

MLS Number 5021418

• Land
• Address West Hill Road
• Acreage 68.89
• Area VT-Windham
• Utilities None

The Cotswold Hill Parcels are five separate surveyed house sites located off West Hill Road in Jamaica, VT. These high elevation properties have some views toward Bromley Mountain to the west and toward Magic Mountain to the east. The views from these sites could be expanded with some tree thinning. Lot 4 is 68.89 acres and is the largest of the five parcels for sale. This lot has a solid woods road leading from the main access road into the property's interior. Immediately next to the road is the first clearing where a house could be built. This is a level spot, and by removing some of the trees near the road, views of the mountains would be seen. Continuing up the road there is another large clearing. This site would have great views, possibly in two directions once some tree clearing has been done. As with the rest of the parcels, this land is not in Current Use, so there are no restrictions on where you can build.

Listed by Thom Milke of Fountains Land Inc.

MLS Number 5012880

• Land
• Address 000 Route 11
• Acreage 99.31
• Area VT-Bennington
• PricePerSqFt 6444.47

Discover Vermont's captivating beauty with this expansive 99.31-acre land parcel in the picturesque town of Peru. This property, surrounded by wooded forests and adjacent national forest land, offers scenic views of neighboring fields and Bromley Mountain. Perfect for nature enthusiasts and adventure seekers, it's just a stone's throw from Bromley Mountain and Wild Wings Nordic Center, and a short drive to the year-round attractions of Stratton, Okemo, and Magic Mountains. This haven provides the perfect blend of privacy and convenience, with walking distance to the charming Peru village center and close proximity to Manchester's shops, restaurants, golf courses, spas, and cultural attractions. High-speed internet availability, electricity at the street, and direct road frontage on Route 11 ensure modern comforts and accessibility. Additionally, the property benefits from a sustainable forestry program with property tax advantages and potential timber value. Imagine building your dream home, a family estate, or creating private trails for biking, hiking, and snowshoeing. Seize this opportunity to invest in a legacy and own a piece of Vermont's pristine landscape.

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

MLS Number 5032279

• Condo
• Square Feet 1,215
• Bedrooms 3
• New Contruction Existing
• Address 5 Red Hickory Road

The season is not over! Red Hickory 5 at Birch Hill is one of the best values today offered at Stratton. This ready to move into attractively appointed Co-Op townhome is located at the quiet end of popular Birch Hill street with views of the mountain. Three bedrooms, two baths, family room. Winter shuttle service to the base lodge. Brand new in ground pool for your summer enjoyment. This second home community has been long maintained and managed for years. Come take a look.

Listed by Terry Hill of Berkshire Hathaway HomeServices Stratton Home

MLS Number 5023272

• Land
• Acreage 91
• Area VT-Windsor
• Utilities None
• PricePerSqFt 3285.71

91± Acres with Stunning Mountain Views in Chester, Vermont Discover a breathtaking 91± acre property just minutes from the charming village of Chester, Vermont. This expansive parcel features stunning alpine views of Fox Chair Mountain, over 3,000 feet of road frontage, and power and internet access along more than half the frontage. Located on the historic Green Mountain Turnpike, this property embodies the best of quintessential Vermont countryside living. A perfect horse property with an outdoor arena and lots of dirt roads for trail riding. The land includes several open meadows, perfect for future development, homesteading, or recreation. Enrolled in Vermont's Current Use Program, the property is both environmentally and financially sustainable. A section of the land was selectively logged, creating a network of trails and plateaus, ideal for hiking, wildlife exploration, or building opportunities. This property offers unparalleled potential for dream homes, private retreats, or as an investment in Vermont real estate. Don't miss the chance to own this unique Vermont land with its stunning mountain views and incredible development possibilities.

Listed by Daire Gibney of Barrett and Valley Associates Inc.

MLS Number 5027632

• Land
• Address Vt Route 100 South
• Acreage 57.76
• Area VT-Windham
• Utilities Cable - Available

Just over 57 ACRES! Large tract of land with stunning views! State wastewater permit already exists and on file for a the construction of a three bedroom home, see WW-2-5317. This lot offers amazing views from several locations, frontage on a private small brook and the larger Wardsboro Brook that flows along Route 100 South in Jamaica. This is a no zoning town and is extremely easy to get your build started this spring! Located just a short drive to Stratton, Mount Snow, Bromley and Magic Mountain Ski Resorts!

Listed by Julie Lowe of Lowe's Real Estate,LLC