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Addison VT Single Family Real Estate

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816 Black Bear Road Jamaica VT 05343

Jamaica, VT816 Black Bear Road

Price$3,995,000

Est. Mortgage: $/month

MLS Number 5096846

  • Residential Single Family
  • PricePerSqFt 726.36
  • Full Bath 5
  • Address 816 Black Bear Road
  • Construction Existing

Set atop the Vermont hillside with stunning views, offering 4 bedrooms with additional sleeping rooms accommodating up to 16 family and friends. A custom-built home by The Wadsworth Design Build/Vermont Barns is an example of craftsmanship blended with modern luxury. Timber-framed architecture, this four-bedroom, six-bath estate offers a warm, rustic elegance that embraces its natural surroundings. Just a short drive from Stratton and Mt Snow ski resorts. The moment you arrive; the home’s striking presence is undeniable. A porte-cochre welcomes you, setting the tone for the beauty that lies within. The heart of the home is the gourmet chef’s kitchen, anchored by a La Cornue stove, rich custom cabinetry, and an expansive island.Douglas fir beams and wide oak floors lend warmth and character, while a masonry fireplace in the great room offers the perfect setting to unwind after a day on the slopes. One of the home’s most captivating features is its silo with a winding staircase illuminated by gas lanterns. A bonus playroom above the three-car garage provides additional space for recreation, while a custom wine room and private movie theater elevate the home’s entertainment offerings. The seamless connection between indoor and outdoor living is one of the home’s greatest attributes. Heated pool, hot tub and fireplace sit against a backdrop of vast mountain views. The landscape is adorned with a sea of peony bushes, adding vibrant color to the meticulously designed gardens.

Listed by Betsy Wadsworth of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.4% last updated on Oct 15, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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253 Lake Avenue Sunapee NH 03782

Sunapee, NH253 Lake Avenue

Price$3,995,000

Est. Mortgage: $/month

MLS Number 5110235

  • Residential Single Family
  • PricePerSqFt 1821.71
  • Full Bath 1
  • Address 253 Lake Avenue
  • Construction Existing

Inspired by Western influences, this exceptional Lake Sunapee retreat blends rustic character with refined luxury in an extraordinary waterfront setting. The main house is anchored by an impressive great room, where a dramatic wall of windows captures sweeping water views and brings the beauty of the lake indoors. The gourmet kitchen is designed for both entertaining and everyday living, with abundant storage, top-of-the-line appliances, and a spacious walk-in pantry/laundry room. A first-floor bedroom with ensuite bath enjoys peaceful garden views. Upstairs, two generously sized bedrooms share an adjacent bath, while a cozy loft offers flexible space for a study, yoga studio, reading retreat, or play area. An inviting open porch connects the main residence to a charming two-bedroom guest house—an ideal private retreat for family and friends—featuring a spacious living area, wet bar, and wide views across the water. Open and covered porches create wonderful places to relax, dine, and enjoy long summer days by the lake. Just a few steps below the living areas, a deep-water dock puts Lake Sunapee at your doorstep. Set out by boat to explore 10 miles of crystal-clear water, dotted with islands, sandbars, secluded coves, and expansive open-water views. The shops, galleries, restaurants, and music venues of Sunapee Harbor are within walking distance, while Vail/Mount Sunapee is just a 10 minute drive. A remarkable combination of luxury, character, location, and quintessential lake living. Welcome to Lake Sunapee!

Listed by Pamela Perkins of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.4% last updated on Oct 15, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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515 West Fields Road Manchester VT 05254

Manchester, VT515 West Fields Road

Price$3,995,000

Est. Mortgage: $/month

Pending

MLS Number 4974441

  • Residential Single Family
  • PricePerSqFt 614.62
  • Full Bath 3
  • Address 515 West Fields Road
  • Construction Existing

Enduring values expressed in stone and wood! VERMONT CRAFTMANSHIP...A WORK OF ART!! Offering a private haven just minutes from downtown, in the heart of Manchester Village, nestled in the foothills of Equinox Mtn. is this rare and exceptional 5-bedroom, 6-bathroom home....The creative design of Architect Ramsey Gourd and Master Builder Mark Breen, well known as two of Southern Vermont's best, along with a dream team of highly skilled craftsmen, all passionate Masters of their own trade, and the result is quite simply....BREATH TAKING!!! The serpentine driveway is bordered by Maples, Birches, Pines and curves gracefully up to the cloistered court yard. Step through the front door into a wide foyer adorned with a gallery of floor to ceiling windows which further enhances the intimacy between the home's interior aesthetic and natural landscape. The home's showstopper has to be its jaw-dropping Great Room, thoughtfully designed as the heart of the home, this massive space accommodates kitchen, dining and living under a vaulted, 26 ft ceiling accented with hand-sawn wood beams. It features an incredible Chef's kitchen at one end and a floor-to-ceiling fire place at the other. The kitchen boasts a 17-foot book matched soap stone clad island seating for 6-8 and light filled sunny breakfast nook. With an outdoor kitchen, fire pit, built in water fall soaking pool, 5 verdant acres, tastefully blends with its idyllic valley setting, serenity is sublime!!!

Listed by Sunny Breen of Josiah Allen Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 7.4% last updated on Oct 15, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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4777 Rush Meadow Road West Windsor VT 05089

West Windsor, VT4777 Rush Meadow Road

Price$3,975,000

Est. Mortgage: $/month

Pending

MLS Number 5108253

  • Residential Single Family
  • PricePerSqFt 905.67
  • Full Bath 6
  • Construction Existing
  • Bedrooms 4

Sheep Run Farm takes its name from the stone-walled lanes where a prosperous 19th-century farmer once moved his sheep between the barn and upper meadows. Nearly two centuries later, those walls still trace the landscape, framing a beautifully reimagined Vermont farmstead on 21± acres in West Windsor, 3 miles from South Woodstock and 8 miles from Woodstock Village. Drawing on the traditional forms of Vermont architecture, the 2017 residence introduces a lighter, more contemporary way of living, with large windows and an open main level overlooking the Rush Meadow Valley and Mount Ascutney. A series of connected buildings includes a two-bay garage, carriage barn, wood room, yoga studio, and private guest suite. The three-season carriage barn is an exceptional gathering space, with a massive stone fireplace and an oversized glass door opening to a stone terrace, pergola and gardens. The land unfolds through rolling meadows, orchards, extensive stone walls, a cascading brook, and two ponds, including a swimming pond with a small beach. Additional buildings include a heated detached garage, equipment barn, and run-in shed at the top of the meadow. Located near GMHA, an extensive network of equestrian trails, and quiet country roads well suited to gravel riding, Sheep Run Farm combines the character of an established Vermont farmstead with the ease and systems of a modern country home. High-speed EC Fiber supports integrated lighting, climate, security, video, and property-access controls.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 7.4% last updated on Oct 15, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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69 South Main Street Wolfeboro NH 03894

Wolfeboro, NH69 South Main Street

Price$3,950,000

Est. Mortgage: $/month

MLS Number 5103036

  • Residential Single Family
  • PricePerSqFt 1077.76
  • Full Bath 2
  • Address 69 South Main Street
  • Construction Existing

Some properties are purchased for what they are. Others are acquired for what they can become. Perfectly positioned in the heart of downtown Wolfeboro, yet privately nestled behind mature trees, perennial gardens, and classic New England stone walls, this extraordinary property offers 138 feet of pristine Lake Winnipesaukee waterfront on Wolfeboro Bay and nearly eight-tenths of an acre of beautifully landscaped grounds. Whether your vision is to preserve and thoughtfully modernize the existing residence or create an entirely new architectural masterpiece, the opportunity is unmatched. Raze-and-rebuild permits are already in place, dramatically reducing the time and uncertainty often associated with premier waterfront development. The existing home may also be redesigned within its current footprint, with professionally designed renderings available to showcase its remarkable potential. The gracious six-bedroom Colonial spans three levels and offers timeless character, two lakeside sunrooms, a spacious living room with wood-burning fireplace, formal dining room with butler's pantry, updated kitchen, refinished hardwood floors, and a first-floor guest suite with private entrance. Equally exceptional are the waterfront improvements. The impressive 48' x 58' dry boathouse provides space for multiple boats or up to six vehicles and includes a lakeside sun porch, workshop, and attic storage. Multiple stone patios, a substantial crib dock, and a protected lagoon create an extraordinary setting for boating, swimming, fishing, and lakeside entertaining. Just steps from Wolfeboro's shops, restaurants, marinas, and year-round attractions, yet offering remarkable privacy, this is one of the most significant waterfront opportunities to come to market in years. This is more than a remarkable waterfront property. It is an invitation to create something truly iconic.

Listed by Jon Parker of Maxfield Real Estate/Wolfeboro

$
$
%
$/month over payments
Federal 30-year interest rate: 7.4% last updated on Oct 15, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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4 Occom Ridge Hanover NH 03755

Hanover, NH4 Occom Ridge

Price$3,950,000

Est. Mortgage: $/month

MLS Number 5074186

  • Residential Single Family
  • PricePerSqFt 497.29
  • Full Bath 6
  • Address 4 Occom Ridge
  • Construction Existing

Set on the crest of Hanover's prestigious Occom Ridge, The Carleton House is a landmark residence with deep roots in Dartmouth College's history. Originally built circa 1897, this shingle-style estate combines timeless New England architecture with a coveted in-town location, just a short walk to Pine Park, Dartmouth's campus, and downtown Hanover. Sited on 1.2 beautifully elevated acres with 273 feet of frontage and sweeping western views over the Connecticut River, the property is accessed via a private driveway, offering both privacy and proximity. The main house features seven bedrooms and is rich in period detail, graciously scaled, light-filled rooms, original hardwood floors, raised paneling, wainscoting, crown moldings, and other hallmarks of its era. Thoughtful updates over time have preserved its historic character while enhancing everyday comfort. The first floor includes an open kitchen/family room, formal living and dining rooms, a spacious front entry hall, rear mudroom, and a half bath. Upstairs, four bedrooms, including a generous primary suite, and a laundry room occupy the second level, with three additional bedrooms and a study on the third. Connected via enclosed breezeway and exterior walkway is a distinct four-bedroom accessory dwelling, a rare feature in this neighborhood. With its own kitchen, two bathrooms, and an open living/dining area, this second home offers versatile living for extended family, guests, or rental income. Elegant, enduring, and intrinsically tied to the fabric of Hanover, The Carleton House is a singular opportunity to own one of the town's most admired historic homes.

Listed by Richard Higgerson of Higgerson & Company

$
$
%
$/month over payments
Federal 30-year interest rate: 7.4% last updated on Oct 15, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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6 Wyanoke Gate Lane Wolfeboro NH 03894

Wolfeboro, NH6 Wyanoke Gate Lane

Price$3,950,000

Est. Mortgage: $/month

MLS Number 5100917

  • Residential Single Family
  • PricePerSqFt 1776.88
  • Full Bath 2
  • Address 6 Wyanoke Gate Lane
  • Construction Existing

Near the protected waters of Diamond Cove, nestled within Winter Harbor, one of Lake Winnipesaukee's most sheltered and sought after areas, this rare offering in the prestigious Wyanoke Harbors Association presents an exceptional opportunity to create a lasting legacy in New Hampshire's premier lakefront destination. Set on approximately 1.78 acres with nearly 200 feet of shoreline, this property combines privacy, protected waters, and an exceptional lifestyle minutes from downtown Wolfeboro, America's Oldest Summer Resort. Charming boutiques, acclaimed restaurants, marinas, Carry Beach, and a vibrant year round community have made Wolfeboro one of New England's most sought-after waterfront destinations. Designed for gathering family and friends, the home features four generously sized bedrooms (plus 2 bonus rooms), 5 baths, and a functional floor plan with an expansive recreation room with a second kitchen ideal for entertaining, multi generational living, rainy day games, or seamless indoor/outdoor summer living. Separate bedroom wings provide privacy for owners and guests, while expansive waterfront-facing living spaces offer the perfect canvas for updates tailored to your vision. An attached two-car garage with Level II electric vehicle charging and access to public water add modern convenience. Outside, a cozy sandy beach invites swimming, kayaking, or simply relaxing along the shoreline, while a substantial T shaped dock provides effortless access to New Hampshire's largest lake, with 72 square miles of crystal-clear water, hundreds of islands, and countless secluded coves. Ownership also includes access to the Wyanoke Harbors tennis pickleball, and basketball courts. Whether enjoyed as it is or thoughtfully reimagined over time, this is a rare opportunity to secure one of Wolfeboro's premier waterfront settings, where protected waters, timeless views, and an exceptional Lakes Region lifestyle come together in a property to be treasured for generations.

Listed by Sara Reineman of BHHS Verani Wolfeboro

$
$
%
$/month over payments
Federal 30-year interest rate: 7.4% last updated on Oct 15, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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2236 River Road Manchester VT 05255

Manchester, VT2236 River Road

Price$3,900,000

Est. Mortgage: $/month

MLS Number 5096230

  • Residential Single Family
  • PricePerSqFt 332.31
  • Full Bath 1
  • Address 2236 River Road
  • Construction Existing

Set on more than 18 picturesque acres along desirable River Road in Manchester Village, this extraordinary, converted farm offers a rare blend of historic character, modern comfort, & endless possibilities. Thoughtfully transformed into a multi-use residential compound, the property features four distinct living, working, & entertaining spaces, each with its own personality and purpose. Throughout the property, authentic antique details have been carefully preserved & integrated into the design. Original barn doors, handcrafted woodwork, exposed beams, & custom trim accents create a warm & inviting atmosphere while seamlessly blending with modern updates & amenities. The former horse barn stalls have been creatively reimagined into a charming office, library, & 3/4 bath, providing an inspiring space for work, study, or quiet retreat. A covered walkway leads to an impressive barn, ideal for large gatherings, celebrations, creative pursuits, or even a prized car collection.. A third living area serves as an exceptional landing place for family, guests, or multigenerational living. Barn-inspired architectural elements continue throughout, complemented by multiple bedrooms, and bathrooms, Completing the compound is a separate one-bedroom cottage, offering privacy & flexibility for guests, caretakers, or your personal slice of serenity. Outside, the grounds are equally captivating. Mature plantings & meticulously maintained landscaping showcase several perennial gardens that bloom throughout the seasons. A heated in-ground pool provides the perfect place to relax. Across the street, additional acreage framed by classic Vermont stone walls and a large stream-fed pond adds another dimension to the estate, with space for future residences, guest accommodations, or a private family compound. A truly exceptional offering in the heart of Historic Manchester Village.

Listed by Carol O'Connor of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.4% last updated on Oct 15, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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217 Logging Hill Road Stowe VT 05672

Stowe, VT217 Logging Hill Road

Price$3,900,000

Est. Mortgage: $/month

MLS Number 5095013

  • Residential Single Family
  • PricePerSqFt 853.2
  • Full Bath 3
  • Construction Existing
  • Bedrooms 4

Magnificent views of Mt. Mansfield, a spring-fed swimming pond, clay tennis court, and 21 private acres create an exceptional setting at 217 Logging Hill Road. Offering a rare vantage point over the Green Mountains, the property combines remarkable privacy with a collection of outdoor amenities seldom found in a single offering. Thoughtfully positioned to capture the scenery, the home's living room, dining area, sunroom, and spacious main-level primary suite all enjoy views of Vermont's highest peak. The upper level includes a second ensuite bedroom, two additional bedrooms, and a full bath, providing comfortable accommodations for family and guests. A walk-out lower level offers casual gathering space for games, television, and entertaining, with direct access to the grounds. The landscape is a defining feature of the property. The pond serves as a centerpiece for summer enjoyment, while a brook flows through the property over natural boulders. Mature perennial gardens provide seasonal color throughout the grounds, and the clay tennis courts offer a rare opportunity for recreation in a spectacular mountain setting. An attached three-car garage includes a dedicated workroom, while the detached Hobby Barn provides flexible space for a studio, fitness area, workshop, storage, or RV parking. An additional equipment barn supports the maintenance and enjoyment of the property's extensive acreage. Combining panoramic mountain views, exceptional privacy, and amenities that are increasingly difficult to find, 217 Logging Hill Road represents a compelling opportunity to own one of Stowe's distinctive estate properties.

Listed by Meg Kauffman of LandVest,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 7.4% last updated on Oct 15, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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16 Sawmill Road Stratton VT 05155

Stratton, VT16 Sawmill Road

Price$3,900,000

Est. Mortgage: $/month

MLS Number 5113882

  • Residential Single Family
  • PricePerSqFt 1098.59
  • Full Bath 3
  • Address 16 Sawmill Road
  • Construction Existing

Location, luxury, and the best of Stratton Mountain living! Just steps from Stratton Village and The Stratton Club, this exceptional mountain retreat offers convenience, privacy, and timeless Vermont charm, with the added benefit of being able to walk to the slopes! Extensively updated, the home showcases beautiful craftsmanship, soaring ceilings, exposed reclaimed timber beams, and a dramatic floor-to-ceiling stone fireplace anchoring the impressive great room. Expansive windows invite natural light and showcase the surrounding mountain landscape, while warm hickory floors create an atmosphere that is both elegant and comfortable. The stunning dining area, with its vaulted wood ceiling, distinctive antler chandelier, and walls of windows, provides a beautiful setting for entertaining. Major improvements include a complete exterior renovation, an expansive new deck offering generous space for outdoor dining and relaxation, and a beautiful stone patio. After a day on the slopes, unwind in the hot tub or gather around the fireplace for a cozy Vermont evening. In addition to five bedrooms, the thoughtfully designed interior features a spacious bonus room above the garage, a private office, and an expansive lower level with an additional bonus room, offering wonderful flexibility for entertaining, recreation, and quiet retreats. The home's proximity to the Village makes enjoying Stratton's restaurants, shops, and year-round activities effortless. Adding to its appeal, the property may transfer with a Stratton Sports Center bond, providing access to additional recreational amenities. Whether you're seeking an exceptional ski getaway or a four-season mountain home, this beautifully updated property offers an extraordinary opportunity to experience the Stratton lifestyle in one of the mountain's most desirable locations.

Listed by Carrie Mathews of Winhall Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 7.4% last updated on Oct 15, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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10 Morgan Road Hanover NH 03755

Hanover, NH10 Morgan Road

Price$3,900,000

Est. Mortgage: $/month

MLS Number 5085263

  • Residential Single Family
  • PricePerSqFt 480.89
  • Full Bath 5
  • Address 10 Morgan Road
  • Construction Existing

Welcome to 10 Morgan Road, an expansive brick Colonial perched atop a stunning open meadow with western views across rolling fields to the Green Mountains of Vermont. Spread across 23.5 acres in Hanover's coveted Etna neighborhood, this property is just minutes to downtown Hanover, Dartmouth College, and Dartmouth Hitchcock Medical Center, yet wrapped in privacy virtually impossible to find in the Upper Valley. Built in 1991 and beautifully renovated in 2005, this home offers over 8,000 square feet of above-grade living space across three levels, plus a 3,300-square-foot finished lower level. Its generous size and practical four-level design maximize flexibility, accommodating year-round family living, extensive work-at-home options, inside and outside entertainment, and extended guest visits like no other Hanover property. A dramatic two-story foyer with an elegant double staircase sets the tone. Formal living and dining rooms flow into a spacious kitchen with a sun-filled breakfast area and a family room anchored by a fireplace. The west-facing sunroom is a showstopper, with panoramic views, glorious sunsets, and natural light throughout the day. The spacious primary suite features a private office, a double-sided fireplace, a walk-in closet, and a stunning bath. Three additional bedrooms complete the second level. The third floor offers a private guest suite with a sitting room, two additional bedrooms, a full bath, and cedar closets. The finished lower level, bright and expansive with walkout access, houses a gym, media room, game rooms, craft space, and full bath. An attached three-car garage adds convenience. Outside, open hayfields, mature evergreens, and classic New England stone walls frame a setting of rare beauty. A truly rare opportunity, grand scale, an unrivaled setting, and outstanding proximity to everything the Dartmouth region offers.

Listed by Richard Higgerson of Higgerson & Company

$
$
%
$/month over payments
Federal 30-year interest rate: 7.4% last updated on Oct 15, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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5685 Vt Route 12 Barnard VT 05031

Barnard, VT5685 Vt Route 12

Price$3,895,000

Est. Mortgage: $/month

MLS Number 5109476

  • Residential Single Family
  • PricePerSqFt 693.92
  • Full Bath 3
  • Address 5685 Vt Route 12
  • Construction Existing

OPEN HOUSE Saturday October 17 from 11 am to 2 pm. AUCTION: Bidder registration deadline: 20 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. SEE PROPERTY-SPECIFIC WEBSITE FOR DETAILS, HIGH RESOLUTION PHOTOS, VIDEOS AND MORE.

Listed by John Snyder of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 7.4% last updated on Oct 15, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated October 20, 2026 6:07 AM EDT