Windsor County

MLS Number 5089848

• Residential Single Family
• Full Bath 3
• Address 5685 VT Route 12
• Bedrooms 5
• Bathroom 6

“HIGHLAND GLEN” - Rarely does a property capture the essence of Vermont as beautifully as Highland Glen. Set on twelve picturesque acres in the charming town of Barnard, this extraordinary estate blends timeless New England character with exceptional comfort, privacy, and recreation. Arrive by the iconic red barn and discover stunning gardens, apple orchard, meandering stone walls, flowing streams, trout-stocked ponds and fountains. Entertain outdoors with the state-of-the-art kitchen, expansive decks, and swim spa overlooking the grounds. Inside, Highland Glen is equally captivating. The heart of the home is a remarkable chef's kitchen featuring an AGA range with four ovens and two hot tops, a La Cornue range, two refrigerators, under-counter refrigeration, two dishwashers, a large walk-in pantry, and a breakfast area beside a wood-burning fireplace. Multiple gathering spaces include a cozy sitting room, formal dining room with fireplace and butler's pantry, a magnificent 4-season lodge room with soaring river rock fireplace, and an upstairs Tavern with vaulted ceilings, full bar, commercial ice maker, and fireplace. The 1st floor primary suite enjoys tranquil pond and woodland views, an oversized bath, and a custom walk-in closet. Additional guest bedrooms, recreation and media rooms, billiards area, office, sauna, wine cellar with tasting room, and secondary kitchenette provide abundant space for entertaining family and friends. Beyond the main residence, the barn serves beautifully for vintage car storage, workshops, or events. A charming exercise chalet and a greenhouse complete the estate. Modern conveniences and excellent mechanical systems throughout. Walk to the Barnard General Store, Barnard Inn, and Silver Lake for kayaking or ice fishing. Woodstock, S-6 and Killington are an easy drive. SEE PROPERTY-SPECIFIC WEBSITE FOR MORE.

Listed by John Snyder of Snyder Donegan Real Estate Group

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

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MLS Number 5072374

• Residential Single Family
• Full Bath 1
• Bedrooms 4
• Bathroom 5
• Square Feet 2,894

A circa 1734 Cape, displaying museum quality authentic detailing, in a setting worthy of a Vermont Life Magazine cover! Originally sited in New Hampshire, the Cape was patiently dismantled, with components meticulously cataloged, and then relocated to an idyllic Vermont hilltop setting! The post and beam construction, gunstock corner posts, exposed beams, extraordinarily wide floor boards, 4 beautiful brick fireplaces, wide board sheathing and hand planed surfaces are desirable components of the original Cape! Now, moving forward to the present day, an experienced designer has recently completely renovated the interior! She has seamlessly blended the early New England architectural features with the benefits of contemporary design amenities! The transformation is truly mesmerizing! Notable major upgrades are all new bathrooms, new bedrooms and a fabulous kitchen that was relocated within the home to benefit from the truly spectacular views. Easily this kitchen is the heart of the home, with an oversized fireplace on one side and long dramatic views on the other side. The additional advantages of contemporary mechanical systems, a full size cement basement and whole house back up generator are unobtrusive nods to present day conveniences! This classic Cape features the traditional Cape floor plan of family oriented rooms and kitchen on the main floor, with luxury bedroom suites above. A 30'x20' wing off the Cape presents the desirable practicality of a privately separated ground level primary bedroom suite. With vaulted ceiling and dramatic windows framing views of the pond and distant hills, this bedroom suite easily becomes a favorite room! Completing this expansive 157 acre estate is a detached private guest cottage with a 4 bay garage below, a large swimming pond, an equipment storage barn and walking trails! Within the extensive 157 acres there is a 24 acre field with agricultural potential! An authentic Cape, in an idyllic setting, without antique home worries!

Listed by John Wetmore of Wetmore Real Estate

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

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MLS Number 5086588

• Residential Single Family
• Full Bath 2
• Address 12 Archibald Lane
• Bedrooms 4
• Bathroom 5

Set on 81 feet of premier frontage along picturesque Lake Rescue, this exceptional Vermont retreat captures the essence of lakeside living. Perfectly positioned on the quieter backside of the lake, the home enjoys extended daylight along with breathtaking sunrises and sunsets that paint the sky year-round. Inside, a spectacular stone wood-burning fireplace anchors the living room, where expansive windows frame stunning water views and flood the space with natural light. Meticulous craftsmanship is evident throughout, with magnificent stonework and thoughtful details enhancing every room. The heart of the home is a wide-open custom kitchen designed for both gathering and entertaining, featuring two islands, granite and butcher block countertops, and a gas range. The main level offers true convenience with a primary suite, private office, mudroom with ample storage, laundry area, and a half bath-all designed for easy living. Upgrades include a recently replaced roof (just one year old), ensuring peace of mind for years to come. A detached two-car garage includes a charming apartment above-perfect for guests, rental income, or a private studio space. Outdoors, beautifully curated plantings and a gentle creek create a serene setting to complement the lakefront lifestyle. Whether you're swimming, boating, kayaking, skiing, golfing, hiking, snowmobiling, skating, or fishing, this property offers year-round recreation-or simply the perfect place to relax and take it all in. A true Vermont picture, where views, ambiance, and lifestyle come together in one remarkable offering.

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 5083683

• Residential Single Family
• Full Bath 1
• Address 166 Jewett Road
• Bedrooms 5
• Bathroom 5

Stately hilltop home built by Silas Banister c.1800, recently undergone a complete restoration. Quality materials & craftsmanship throughout. It has gorgeous views of nearby Ascutney Mountain & long-range views of NH. The property consists of 98 acres made up of fields, hard & softwoods, trails, a large sugarbush (potential for a future boiling operation). Conserved by Upper Valley Land Trust, enrolled in Current Use. The main floor offers a new kitchen which boasts a beautiful 11' quartzite island & counters. Dining & Family Room with soapstone woodstove, Living Room with a new Rumford Fireplace with rod iron & glass doors for efficiency. A large Sunroom with slate floor, more than an entry it's a nice transitional space to enjoy, 3 BR/3 BA and a Sitting area on the 2nd floor with a tranquil view of the back fields. 2 additional BRs and a half bath on the 3rd floor. All new wiring, plumbing, new Bosch propane furnace supplies radiant heat, triple pane, Anderson low-E4 windows, sheetrock, DaVinci slate-like rubber roof & cherry floors. Fully insulated, extremely efficient. Custom built trim, wide baseboards, wainscoting & cabinets. 200+ year old pine boards from the house were used to craft bathroom vanities, 3rd floor stairs & beautiful doors. Outdoor amenities include in ground pool, gardens & lovely stone patio. A large-3600 sq ft former dairy barn with new wiring & FHA furnace & oil tank. Now used as a garage, workshop & abundant storage space offers ENDLESS possibilities!

Listed by Dana Waters and Paula Waters of Dark Horse Realty

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

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Your Questions & Comments I have a question about the property at 166 Jewett Road West Windsor VT 05037 (#5083683).

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MLS Number 5072035

• Residential Single Family
• Full Bath 1
• Address 249 Sawyer Road
• Bedrooms 3
• Bathroom 5

Located in Woodstock, Vermont just one mile from the village green, the Alta House offers a rich quality of life filled with poolside sunsets, mountain vistas, proximity to town, and access to endless outdoor recreation opportunities. Enjoy the convenience of living close to the shops, cafes, and restaurants of Woodstock, while being tucked away in your own world above. The 3-bedroom primary residence is perfectly sited to overlook Woodstock's iconic Mount Tom and the Marsh-Billings Museum, Vermont's only National Park. The property sits at the end of a quiet road with only one other neighboring residence and is surrounded by over 400 acres of conserved land. There is a bedroom suite on each of the three levels, allowing family members or guests to claim their own space. The open living room on the main level is a natural gathering place, either by the fire in the winter, or out on the deck in the summertime to take in the views. The adjoining 1,040-sqft modern pool house was completed in 2023, providing a luxurious new extension of the home. Inside is an open floor plan, where floor-to-ceiling windows showcase unobstructed mountain views to the North and West. Thoughtfully designed with a custom Viking kitchen, spa-style walk-in shower, and guest bed, the pool house is ideal for entertaining guests, hosting family parties, or relaxing apres-ski. The outdoor heated pool is a centerpiece of the property, providing four-season enjoyment.

Listed by Andrew Bustin and T Story 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 5077313

• Residential Single Family
• Full Bath 6
• Bedrooms 5
• Bathroom 7
• Square Feet 5,728

Solitude home at the top of the hill awaits! Solitude on Okemo Mountain, where this exceptional five-bedroom home captures the ultimate ski location, breathtaking long-range views, and unparalleled privacy. Perfectly positioned to embrace the beauty of the surrounding mountains, this residence offers a rare opportunity to enjoy true slope-side living in one of Vermont's most sought-after resort communities. The main floor offers a sunken living room with views of the Okemo Valley. Off the living room is a dining room and kitchen with a large island and room for entertaining. The family room off the kitchen has a full bathroom and access to the large deck with a hot tub overlooking the ski trail. From the main floor, you can access the heated garage. Above the garage is a primary suite. The primary suite has a vaulted ceiling,a gas fireplace, a balcony, and a soaking tub with window views. The bathroom has a large shower, a double vanity, and a walk-in closet. Back down to the main level, you can access another second floor with 2 en-suites, each with a full bathroom. There is a den and a full bathroom to complete the second level. The basement area offers a full game room and family room, 2 additional bedrooms, a full bathroom, a half-court basketball room, and a mudroom, which opens to the bridge that brings you to the ski trail. The current homeowner has thoughtfully enhanced the property with numerous upgrades, including new mechanical systems and additional improvements that enhance efficiency and livability. Step outside and experience mountain living at its finest in this secluded setting, where serenity meets adventure right at your doorstep. Whether you're relaxing after a day on the slopes or entertaining while taking in the sweeping vistas, this home delivers the very best of resort lifestyle. If you're looking for the best of the best, call us today to schedule your private showing and discover this extraordinary mountain retreat.

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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Your Questions & Comments I have a question about the property at 191 Moon Shadow Drive Ludlow VT 05149 (#5077313).

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MLS Number 5051212

• Residential Single Family
• Full Bath 3
• Village Ludlow
• Bedrooms 5
• Bathroom 5

Welcome to your mountain sanctuary in the heart of Solitude VillageOkemo’s premier slopeside community. This luxurious 5-bedroom, 3-bathroom retreat offers true ski-on/ski-off access, allowing you to hit the Rising Star Trail or Moon Shadow right from your doorstep. Step inside to a warm, elegant interior featuring radiant-heated tile and rich hardwood floors throughout. The expansive great room, with its stunning stone fireplace and vaulted ceilings, creates the perfect aprs-ski gathering space. Just off the great room, a custom beverage bar with seating for three invites you to unwind with a cocktail while watching the snow fall. The chef’s kitchen is appointed with high-end appliances, granite countertops, and custom cabinetryideal for entertaining. The dining room comfortably seats twelve, making it perfect for holidays and celebrations. After a day on the slopes, drop your gear in the well-designed mudroom with built-in cubbies before heading down to the walkout lower levelcomplete with a pool table, exercise space, sauna, and hot tub for ultimate relaxation. A large game room with tons of comfortable seating for movie watching. The spacious primary suite includes a private balcony, perfect for morning coffee with mountain views. Additional features include a dramatic carport entry, two-car garage, ample storage, and timeless craftsmanship throughout. Whether you're seeking a serene winter escape or an active four-season retreat, this home delivers. ROFR

Listed by Joseph Karl 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 5091062

• Residential Single Family
• Full Bath 2
• Address 66 Hollow Farm Road
• Bedrooms 5
• Bathroom 6

CURTIS HOLLOW FARM- Exceptional estate on the western edge of Woodstock offering 105 diverse acres bordering Calvin Coolidge State Forest. The updated main house features 5 bedrooms and 4 baths, filled with abundant natural light and thoughtfully designed for both large gatherings and quiet retreat spaces. The open-concept main level includes a spacious living room with picture windows overlooking the landscaped grounds, a recently updated chef's kitchen with a stunning Mercury/Aga range, and generous dining space nearby. On the east side of this level, the original historic homestead-with its native timbers and stone fireplace-creates a warm and intimate dining experience. A wraparound deck provides additional space for outdoor dining and entertaining, while bedroom with its own bath completes this floor. Upstairs are 4 additional bedrooms, several featuring charming portal windows with views over the surrounding fields & hills. The primary suite is spacious and inviting, highlighted by exposed historic timbers, a sitting area, direct access to an upper deck, and a spa-inspired bath. On the uppermost level, the cupola offers the perfect yoga studio or quiet reading nook, complete with its own private deck. The grounds are truly magical, with an extensive trail network throughout the property and direct access to a magnificent waterfall and swimming hole just beyond the lot line within the State Forest. Large level lawns, mature landscaping, and a brook flowing along the southern side of the property add to its private tranquility. Nestled beside the brook is the guest house, known as the Brook House-a well-maintained 3-bedroom, 2-bath home privately sited away from the main residence, with its own lawn and deck overlooking the water below. With a convenient location offering easy access to Woodstock and Bridgewater Villages and a short drive to Killington Mountain Resort, this stunning estate is the consummate blend of privacy, charm, and modern convenience.

Listed by David Donegan of Snyder Donegan Real Estate Group

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

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MLS Number 5002873

• Residential Single Family
• Full Bath 2
• Address 61 Academy Circle
• Bedrooms 6
• Bathroom 6

Hyacinth House has been a landmark property in the historic village of South Woodstock from its early settlement in the 1800's. Sited on a knoll overlooking the Kedron Brook this grand residence has been carefully restored by talented craftsmen. Taking care to keep the beautiful original details the owners have brought the systems into the 21st century with the highest quality of materials. The back ell seamlessly ties into the original brick Federal and offers additional spaces for entertaining guests including the Pine Room with its' large fireplace for snowy winter nights. The brick Federal consists of formal living room, dining room, library and gourmet kitchen with walk in pantry. On the second floor there are 2 ensuite bedrooms,4 more bedrooms, 2 baths and large laundry room. The third floor offers the surprise of a family room that was originally a ballroom with curved ceiling. There is also a bright studio and half bath on that level. The new attached oversize 2 car garage is accessed from the Pine Room and the fully renovated basement. The 2+/- acres comprises of lovely landscaping around the home and plenty of land for gardens . The 18th century barn and corn crib lend much charm to the setting. There are 8 additional acres for sale if one would like to expand the property. Walk to the charming village store and enjoy dinner on the porch of the Ransom Tavern. Only 5 miles to Woodstock and a short drive to multiple ski areas. South Woodstock is truly a bucolic place to call home! Call today for a private viewing.

Listed by Carol Wood of Williamson Group Sothebys Intl. Realty

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

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