Very Cool Houses

MLS Number 5077720

• Residential Single Family
• Full Bath 3
• Construction Existing
• Bedrooms 6
• Bathroom 6

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

MLS Number 5052439

• Condo
• Square Feet 2,363
• Bedrooms 4
• New Contruction Existing
• Complex Rising Bear Lodge

Perfect for the large family! Four bedrooms, Three and a Half Baths, plus a Loft! In highly desirable Rising Bear Lodge, Top Floor, Corner location! Easy walking distance to the Slopes, (Shuttle also available), the Commons' Skating Pond, and the Village Shops and Restaurants. Other amenities include a year round heated Pool, outdoor hot tubs, and a cedar sauna---all comfortably accessible by the heated patio! Rising Bear also offers an owners' Hearth Room with a large, stone fireplace. Each individual home offers a cozy, warm gas fireplace, air conditioning for summertime, owner storage area, lockers, an underground heated parking garage with two assigned spaces! Your Vermont home away from home!

Listed by Edwin Kevil of Stratton Real Estate

MLS Number 5089553

• Residential Single Family
• Full Bath 4
• Construction Existing
• Bedrooms 3
• Bathroom 4

Welcome to your private retreat on Cider Mountain! Set on a beautifully private parcel with sweeping year-round views of Sugarbush Resort and Camel's Hump, this exceptional post and beam home captures everything buyers dream about when they picture Vermont living. Thoughtfully built by a well-known local specialty carpenter using locally sourced materials, the home showcases stunning hemlock throughout, beautiful maple hardwood floors, and timeless craftsmanship that gives the entire property warmth, character, and soul. A wood burning stove and fully functioning stone chimney create the perfect cozy Vermont ambiance throughout the colder months. The open concept layout creates an inviting flow throughout the home, while radiant heat adds comfort year round. Features include a first floor in-law suite, spacious primary suite with a private balcony, detached 3-car garage, greenhouse, and expansive garden space ideal for those looking to homestead, entertain, or simply enjoy a quieter way of life surrounded by nature. Large windows frame the mountains beyond, filling the home with natural light and breathtaking views in every season. The fully finished walkout lower level offers exceptional flexibility with its own private entrance, full kitchen, bathroom, and laundry area perfect for guests, recreation space, extended family, or potential multi-generational living. Outside, the property truly shines. Spend mornings on the porch watching the sunrise with a cup of coffee in hand, afternoons gardening or picking fresh berries from the numerous berry bushes throughout the property, and evenings relaxing on the spacious front porch or primary balcony soaking in the mountain views and unmatched serenity. Backing up to protected land, the setting will remain private, peaceful, and untouched for years to come. Rarely does a property combine this level of privacy, craftsmanship, acreage, flexibility, and breathtaking natural beauty in one truly unforgettable Vermont setting.

Listed by Lindsay Haley of Vermont Real Estate Company

MLS Number 5083578

• Residential Single Family
• Full Bath 1
• Address 50 Grouse Lane
• Construction Existing
• Bedrooms 4

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

MLS Number 5089684

• Residential Single Family
• Full Bath 2
• Address 1268 Myers Road
• Construction Existing
• Bedrooms 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.

MLS Number 5078509

• Commercial
• Address 40 The Common
• Year Built 1920
• Area VT-Windsor

A rare opportunity to own one of southern Vermont's most beloved hospitality landmarks. Located directly on the picturesque village green in historic downtown Chester, the iconic Fullerton Inn stands as the centerpiece of this charming New England village and offers a fully established turnkey business ready for its next steward. Set on 2.28 acres with access to the scenic Williams River, the property combines classic Vermont character with exceptional hospitality infrastructure. Guests gather in multiple inviting spaces including a spacious main dining room, a cozier secondary dining area, and a lively tavern and bar, creating a warm and memorable destination for locals and travelers alike. A large rear deck overlooking the grounds and river provides an ideal setting for outdoor dining, seasonal gatherings, and private celebrations. The inn features 20 guest rooms and suites, along with two separate owner or general manager apartments, offering flexible on-site living and management options. A professional commercial kitchen supports a full restaurant operation and catered events. Well known as a regional gathering place, the property also serves as a popular event venue for weddings, large parties, and cultural or civic celebrations. The inn even appeared as a filming location for the 2008 Hallmark movie Moonlight & Mistletoe. Offering 18,896 square feet of hospitality space in the heart of Vermont ski country, the Fullerton Inn benefits from year-round tourism, from winter skiers to the region's world famous fall foliage visitors. An extraordinary chance to own a true Vermont destination.

Listed by Patrick Kelley and Betsy Adamovich of Real Broker LLC

MLS Number 5046390

• Commercial
• Year Built 1848
• Square Feet 14,861
• Acreage 3.5
• Area VT-Bennington

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

MLS Number 5046479

• Residential Single Family
• Full Bath 15
• Construction Existing
• Bedrooms 17
• Bathroom 20

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

MLS Number 4989182

• Residential Single Family
• Full Bath 2
• Village Quechee
• Address 399 Bentley Road
• Construction New Construction

The Evergreen at Mountain Stream - Currently under construction at 399 Bentley Road, the Evergreen offers 2,709 square feet of contemporary living across two finished levels, paired with a detached two-car garage. A long, low silhouette under a standing-seam metal roof, composite board-and-batten siding, and oversized windows give the home a distinctly modern presence - clean architectural lines softened by the surrounding forest. The main level opens to expansive living, dining, and kitchen areas anchored by a Wittus Shaker wood stove and stretching out to a generous deck designed for entertaining or for quiet mornings beneath the trees. A primary suite sits alongside three additional bedrooms and two more full baths, delivering true single-level living whenever so desired. The walkout lower level adds a fifth bedroom, full bath, family room, flex space, laundry, and generous storage - exceptional flexibility for family, guests, and four-season Vermont living. Interior finishes are uncompromising throughout: hand-applied skim-coat plaster walls for a refined, seamless finish; wide-plank white oak floors; custom tilework in the kitchen and all bathrooms; natural stone countertops on every kitchen surface and vanity; and thoughtful, high-quality millwork in every single room. Built to perform as beautifully as it lives, the Evergreen features high-efficiency construction with R-30 wall insulation and R-60 in the cap, delivering year-round comfort and meaningful energy savings. Located within Quechee Lakes, owners enjoy access to two championship golf courses, an alpine ski hill, tennis, pickleball, and paddle facilities, lake and river recreation, and an extensive year-round network of hiking, biking, and Nordic ski trails. Mountain Stream represents a new chapter at Quechee Lakes - architecturally considered homes built by a developer committed to craft, performance, and longevity. This Is The Place. Photos are renderings only. CO expected 6/1/2026

Listed by Richard Higgerson of Higgerson & Company

MLS Number 5087874

• Residential Single Family
• Full Bath 1
• Construction Existing
• Bedrooms 5
• Bathroom 5

Set on 18 private acres, Popple Dungeon is a distinctive Vermont property offering the feel of a true country retreat. Owned by one family and designed and built by its owner, the Williamsburg-style reproduction Saltbox reflects a deep appreciation for traditional craftsmanship and enduring design. Inside, the home is defined by warm, handcrafted details-wide-plank wood floors, paneled walls, layered moldings, and reclaimed beams create a sense of comfort and authenticity throughout. The scale and layout offer a balance of inviting gathering spaces and quieter rooms, well-suited for both everyday living and hosting. Originally operated as a bed-and-breakfast, the home was thoughtfully designed to welcome guests while maintaining a natural flow and sense of privacy. The surrounding land provides a peaceful and private setting, with stone walls, established gardens, wildflowers, fruit trees, and a blueberry patch woven into the natural landscape. Open areas and wooded sections create a property that feels both curated and comfortably natural, offering space to explore, relax, and enjoy Vermont's changing seasons. A guest house and dedicated woodworking barn add to the property's appeal, offering flexibility for hosting, hobbies, or creative pursuits. Ideally located near the charming village of Chester, the property offers convenient access to year-round outdoor recreation, including skiing, hiking, biking, fishing, and scenic trails. Throughout the home, the builder's attention to detail is unmistakable, with thoughtfully crafted custom woodwork and timeless finishes that reflect a genuine commitment to quality and design. Quiet, private, and rooted in tradition, this is a property well suited for those seeking a classic Vermont retreat and lifestyle.

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

MLS Number 5091076

• Residential Single Family
• Full Bath 4
• Address 163 Chapin Road
• Construction Existing
• Bedrooms 4

Set on over 10 private acres with access to an additional 26 acres of common land, this exceptional 4-bedroom, 5-bathroom Essex property offers a rare combination of privacy, flexibility, and everyday convenience. Located just minutes from local amenities with an easy commute to Burlington, the University of Vermont Medical Center, and Burlington International Airport. With over 6,000 square feet of living space, the home was thoughtfully designed for both entertaining and comfortable daily living. Soaring cathedral ceilings and expansive windows fill the main living areas with natural light, anchored by a dramatic floor-to-ceiling stone fireplace. The kitchen features rich wood cabinetry, stainless appliances, generous counter space, breakfast bar seating, and a sunny breakfast nook, all flowing easily into the formal dining room and spacious living area. A screened porch and expansive wraparound deck extend the living space outdoors. A standout feature of the home is the flexible first-floor layout, including a guest suite with vaulted ceilings, en suite bath, and direct deck access ideal for guests or a comfortable first-floor primary option. A dedicated den or office adds even more versatility. Upstairs, the primary suite includes a gas fireplace, walk-in closet, and spacious bath with soaking tub, along with two additional bedrooms and second-floor laundry. The finished walkout lower level offers exceptional bonus space with a fireplace, bar, game room, gym, and additional flexible areas for entertaining, hobbies, or guests. Outdoor features include an attached heated garage, stone patio, reinforced deck with hot tub hookup, gas grill hookup, pole barn ideal for equipment or RV storage, and a detached barn/2-car garage with finished space above and a 3/4 bath. Perfect for hobbies, studio space, guests, or flexible use. A truly special Essex property offering exceptional space, privacy, and opportunity both inside and out.

Listed by Nancy Warren of Coldwell Banker Hickok and Boardman