Bennington County

MLS Number 5046479

• Residential Single Family
• Full Bath 15
• Bedrooms 17
• Bathroom 20
• Square Feet 14,861

The historic Arlington Inn & Spa is the centerpiece of scenic Arlington, Vermont. It features a tavern, restaurant and massage spa room. There are 15 guest rooms in 3 buildings, and an antique event barn on over 3.5 beautifully landscaped acres. This unique property can easily be configured in many creative ways. It could remain as an inn with a restaurant and bar. It could become a restaurant and event destination for weddings and parties. And it would make a wonderful family compound or corporate retreat. In addition to three guest suites, the c. 1848 Main Inn offers a commercial kitchen serving formal and informal dining spaces and the fully renovated Deming Tavern. The romantic Tavern features an antique bar front crafted from a pulpit from the Old First Church in Bennington and Pullman Railcar lighting in a nod to Martin Chester Deming, the original owner of the property and a railroad magnate. While respecting historical detail, the current owners have added modern conveniences and updates. This includes underground utilities, fiber optic high-speed WIFI internet, SmartTV in every room, portable a/c units and USB port alarm clocks. Antique romance with 21st century upgrades! Guests are free to enjoy the front and back yards, patio areas, gazebo and beautiful perennial gardens. This special property is ready for the next stewards to take it to a new level! Please click on the "unbranded tour" link for a virtual tour of the property.

Listed by Vicki Wilson of Maple Leaf Real Estate

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

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MLS Number 5077720

• Residential Single Family
• Full Bath 3
• Bedrooms 6
• Bathroom 6
• Square Feet 4,864

Gorgeous, renovated Colonial offering exceptional flexibility, thoughtful design, and timeless charm. This beautifully updated property features a spacious main residence along with a stunning addition that includes a full in-law suite and a private studio above ideal for guests, extended family, a home office, or potential rental income. Solar panels installed above the garage power efficient mini-split systems, and a Tesla Powerwall provides added energy independence and peace of mind. The main house offers four bedrooms, a fabulous chef's kitchen with quality finishes and generous workspace, and warm, inviting living areas filled with abundant natural light. Magnificent views of Mount Anthony and the sweeping five-acre meadow below can be enjoyed from the kitchen, dining room, living room, and screened porch-where wildlife is often part of the daily landscape. A new large enclosed porch further expands the living space, creating the perfect setting to relax or entertain year-round. Set on 17+ picturesque acres framed by classic stone walls, the property offers lovely views, open meadow, and wooded privacy with ample outdoor space to explore and enjoy. A three-car detached garage provides excellent space for vehicles, storage, or hobby use, while a workshop and spacious woodshed add exceptional functionality. Equestrian enthusiasts will appreciate the charming pony barn and paddock, completing this truly special setting. A rare opportunity to own a beautifully expanded home with multiple living options, sustainable features, and breathtaking views in a serene and private landscape.

Listed by Kelley McCarthy of Mahar McCarthy Real Estate

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

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MLS Number 5083578

• Residential Single Family
• Full Bath 1
• Address 50 Grouse Lane
• Bedrooms 4
• Bathroom 5

Custom-built Dorset Hollow estate offered for the first time since 1998. Perfectly situated on 10 private acres abutting 3,200 acres of conservation land, this 5,100 sq ft residence combines timeless quality, fine finishes, and Vermont mountain charm. Designed for comfort and entertaining, the home features 4 bedrooms, 5 bathrooms, and an attached 2-car garage. Elegant details include four fireplaces, verdi marble flooring, Marvin windows, a slate roof, and a Viessmann boiler-premier materials chosen for durability and style. The dramatic living room boasts a large wood-burning fireplace framed by 8-foot, 12-panel Marvin windows, crescent-shaped upper windows, and soaring 30-foot ceilings that fill the space with natural light. The chef's kitchen will delight serious cooks, offering THOR double ovens, a mini wood-burning brick fireplace, center island with butcher block top, verdi marble floors, soapstone counters, Wood Harbor cabinetry, and a charming built-in breakfast alcove. The formal dining room features 12-foot ceilings, crown molding, and direct access to an elevated synthetic sundeck, ideal for entertaining or relaxing outdoors. The intimate den, with its brick fireplace, wet bar, and copper sink, provides a cozy retreat for quiet evenings. A first-floor half bath and laundry room add convenience. Upstairs, a custom fluted staircase leads to two spacious guest bedrooms, a full tile bath, and a walk-in cedar closet. The primary suite (30x14) is a luxurious escape featuring a gas fireplace, 10-foot ceilings, crown moulding, and peaceful mountain views. Two walk-in closets and a spa-inspired primary bath include a sauna, whirlpool tub, tile shower, and double vanity. A fourth ensuite bedroom completes the upper level. Outdoors, the serene setting offers unmatched privacy while being just minutes from Dorset Village and Manchester amenities. This rare offering combines classic design, privacy, and enduring Vermont elegance.

Listed by David Halligan 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 5089684

• Residential Single Family
• Full Bath 2
• Address 1268 Myers Road
• Bedrooms 4
• Bathroom 4

Welcome to your paradise! This exquisite 30 acre estate offers extreme privacy, a custom home with architectural details throughout, a modern 1 BR guest apartment, an oversized 2 car garage, top notch equestrian facilities, a trout pond, playhouse and the list goes on and on. The winding driveway leads one to an enchanting compound, as it opens to overlook the exclusive estate in all of it's glory. The 3 Bedroom, 4000SF home boasts 10 foot ceilings, with reclaimed antique oak pocket doors from a nearby mansion, inlaid floors, stained glass windows, arches and a custom cherry and granite eat in island kitchen. The foyer, gracious leads to the expansive living room and kitchen overlooking the fantastic spring fed pond... there is a main level primary suite, and second floor gathering space with pond-side balcony and 2 bedrooms. The finished basement hosts a family recreation room and a sauna. Equestrian facilities are comprised of a recently built barn with 4, 12 X 12 stalls boasting ThuroBed Matress Systems, as well as a 12 X 18 foaling stall, leaving room for additional stalls. Paddocks and pastures with Ramm Flex Fencing and a USDF regulation 20m X 60m dressage arena with sand and fiber footing. There's a large shed and a 5 acre pasture. There's so much room for storage or lifestyle expansion within the main house or the building hosting the detached garage and guest house as there is a full unfinished second floor that could expand studio, exercise and office needs. This special location is convenient to area amenities yet a total feel of being away from it all! Whether you are an equestrian, or you are looking for an idyllic homestead, a place to enjoy nature and peace, and/or a property that demonstrates Vermont beauty, one shall adore this property. It is conveniently 3 hours from NYC, 1 hour from the Albany airport, and 25 minutes from Manchester, all while still feeling a world away! West Mountain Views are engaged wherever one is on the property!

Listed by Laura Beckwith of Josiah Allen Real Estate, Inc.

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

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MLS Number 5090534

• Residential Single Family
• Full Bath 1
• Address 39 Eagle Ridge
• Bedrooms 5
• Bathroom 5

5.7 beautiful acres just off of Morse Hill Road where the southern exposures are to behold, a warm and inviting modern designed residence, post and beam barn and sweeping mountain views await your attention! The 5 Bedroom mostly ensuite house features the grand open concept where living areas are spacious and distinctive areas yet transition beautifully from space to space with newly finished hickory flooring and all areas are walking out to a great deck that overlooks the bucolic 5.7 acres. There's stone walls, easy perennial gardens, the classic red barn, some fruit trees, a small pond, and meadow. Plenty of room to maximize it's potential for vegetable beds... a pool... or any lifestyle whimsy. The great-room marble cooks kitchen has vast cabinetry and upgrade stainless appliances, the dining room would entertain large or small gatherings with ease and the step down living room with cathedral wood ceiling and massive stone hearth wood burning fireplace is lovely with warm natural light. There's an office, powder room and laundry room convenient to the central family command center. The primary suite is quite luxurious with the soaking tub, separate stone shower, double vanity and walk in closet. There are two ensuite bedrooms upstairs boasting new baths. The lower level sun soaked family room can work for recreation, lounging, media, or exercise... there's two other lower level bedrooms or one is considered more in line with flex-space such as a second office. There is a new bath there as well! All baths are just finished. Add central air, the three car attached garage, with and work-shop/studio extension, the fantastic barn that also has a work-shop addition where parties can be had with a separate drive. The possibilities are endless in how this property and house can be utilized. Easy single floor living for the empty nester with plenty of room for the generations to reappear, or a terrific family home. Mountain Views! Welcome to 39 Eagle Ridge!

Listed by Laura Beckwith and Elizabeth Romano of Josiah Allen Real Estate, Inc.

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

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MLS Number 5058749

• Residential Single Family
• Full Bath 3
• Address 932 McNamara Road
• Bedrooms 4
• Bathroom 3

Tucked away at the end of a gently curved, tree-lined drive, this exceptional contemporary home blends timeless elegance with Vermont charm. A welcoming paver patio leads to the informal entry, while a marble pathway guides you to the striking formal entrance and grand foyer. Inside, locally sourced marble floors flow into rich cherry hardwoods, setting the tone for quality throughout. Soaring ceilings extend from the foyer into the formal living room with a wood-burning fireplace and into the relaxed family room, where a second fireplace with a dramatic floor-to-ceiling brick hearth creates a warm gathering space. The formal dining room opens to an expansive eat-in kitchen, designed with generous counter space for cooking, entertaining, and daily living. The serene primary suite offers oversized windows and a charming pellet stove, while the spa-like bath includes a soaking tub, walk-in shower, double vanity, and ample closets. A private guest suite with its own bath and a laundry/utility room complete the first floor. Upstairs are two additional guest bedrooms, a full bath, and a spacious recreation room with wet bar and wood finishes-ideal for a pool table or media space. A detached, heated and cooled studio offers the perfect home office, art studio, or retreat. Nestled on 5 picturesque acres and just a short stroll to the Equinox Highlands Natural Area, this property balances sophistication, comfort, and Vermont lifestyle. NEW ROOF and exterior maintenance all updated for new buyer!

Listed by Britt Wohler of WOHLER REALTY GROUP, Martina Dvorak-Grattan of Wohler Realty Group

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

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MLS Number 5072983

• Residential Single Family
• Full Bath 2
• Bedrooms 3
• Bathroom 3
• Square Feet 2,560

A private Vermont sanctuary set on over 40 acres of meadows, rolling hills, stone walls, and mature forest. This sophisticated modern farmhouse offers rare peace, privacy, and natural beauty, and sweeping seasonal views from every room. Designed to blend seamlessly into the land, the light-filled home features expansive Marvin windows and refined custom finishes throughout. The chef's kitchen includes custom inset cabinetry, marble countertops, a Sub-Zero refrigerator, Viking range, and a walk-in pantry with walnut counter and beadboard ceiling. The primary suite offers a cathedral ceiling and tranquil views, with a spa-like bath featuring marble floors and a clawfoot soaking tub. Two additional bedrooms, a full bath, and laundry complete the second floor. Recent 2025 updates include a standing-seam metal roof and mini-split systems throughout. Property is offered fully furnished with nearly new pieces from Pottery Barn and West Elm. A rare opportunity for those seeking privacy, beauty, and understated Vermont luxury. All measurements approximate.

Listed by Andrea Kaplan 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 5080413

• Residential Single Family
• Full Bath 4
• Address 121 High Meadow Road
• Bedrooms 6
• Bathroom 4

Bring the whole household to this great place with lots of room for fun. A 6-bedroom, 4-bathroom Adirondack-style Ski Chalet located in a neighborhood just minutes from the Stratton Mountain Ski Resort, with free door-to-mountain shuttle service on select days. Amenities include four (4) fireplaces, best hot-tub on the market, an in home gym, electric sauna, pool table, SuperChexx Bubble Hockey table, foosball table and corn hole, Sonos entertainment system, and high-speed Wi-Fi and digital cable service. Top of the line WOLF Stove and appliances. 4 years of STRONG rental value. This House checks every box. This is the premier house in the area. Huge owners closet. You have so many options here.

Listed by Ralph Harvey of Listwithfreedom.com

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 121 High Meadow Road Winhall VT 05340-9999 (#5080413).

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