Very Cool Houses

MLS Number 5094211

• Residential Single Family
• Full Bath 1
• Address 874 Middletown Road
• Construction Existing
• Bedrooms 5

Set along picturesque Middletown Road, just beyond the historic village of Grafton, this elegant five-bedroom residence enjoys a setting that feels both timeless and deeply peaceful. Perhaps it is the pleasing symmetry and classic proportions of the c.1815 brick Federal home with its Georgian floor plan. Perhaps it is the views of rolling meadows and rounded hills that unfold in both directions. Or perhaps it is simply the feeling of being here--a quiet sense of belonging that is difficult to explain and impossible to forget. Filled with natural light, the property has a welcoming spirit. A pond, apple orchard, perennial gardens, blueberry bushes, ancient maple trees, and historic stone walls create a landscape rich in beauty. The home sits along a quiet gravel road that forms part of one of Grafton's favorite four-mile walking loops, while trails meander through the property's 66 acres of fields and woodland. The Saxtons River traces one edge of the property. In the early nineteenth century, Major Benjamin Dwinell and his wife, Mehitable, built this home and raised eleven children here. The family prospered from the land, tending a large flock of sheep and cultivating one of the most productive apple orchards in town. By the late 1800s, Grouse Hill had begun a new chapter as a country retreat for a New York family. Over the years it has served as a boarding house, an inn, a full-time residence, and a cherished second home. Through each chapter, it has remained what it is today: a gracious and welcoming place that draws people in, encourages them to linger, and leaves a lasting impression. 22 miles from Okemo. 2 hours 44 minutes from Boston and 4 hours 19 minutes from New York.

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

MLS Number 5097749

• Residential Single Family
• Full Bath 1
• Address 36 Beaver Street
• Construction Existing
• Bedrooms 3

Your Ultimate Vermont Mountain Retreat Awaits! Luxury log home plus a 2,250 sqft guest house! Just 4 miles from Stratton & minutes to Bromley, this inviting log home is the perfect year-round escape - crafted for adventure, relaxation, and making lasting memories in every season. Whether you're hitting the slopes in winter, hiking through summer trails, or soaking in the stunning fall foliage, this property delivers! Plus, it's only a 10-minute drive to Manchester, where you'll find excellent dining and local shops. Step inside the main house to a soaring great room with exposed beams, a dramatic stone fireplace, and lodge vibes that scream cozy comfort. At the heart is a chef's kitchen that opens to a bright sunroom and dining area, ideal for gathering with family and friends. Fireplaces throughout, plus a game-packed entertainment zone with pool table, shuffleboard, arcade games, TVs, and a wet bar bring endless fun indoors. With 3 bedrooms, 2 bonus rooms and 4 bathrooms, there's room for everyone to relax in comfort. But that's not all - this expansive property also includes a 2,250 sqft guest house with an open kitchen, 1.5 baths, covered porch, and an epic downstairs arcade/bar. Outside is a private playground for all ages: fire pit, hot tub, full outdoor kitchen with fireplace, TV, and grills. Enjoy the pond, playground, horseshoes, and a court for basketball, pickleball, or badminton. Whether you're carving fresh powder, basking in summer nights or soaking in Fall colors - this is Vermont living on a whole new level!

Listed by Mary Kate Grey and Jamie Wylie of Stratton Real Estate

MLS Number 5090364

• Residential Single Family
• Full Bath 1
• Address 235 Primrose Lane
• Construction Existing
• Bedrooms 3

Experience the essence of Vermont living on this totally private property tucked away at the end of Primrose Lane in Ferrisburgh. The 24-acre landscape is an enchanting mixture of verdant fields and woodlands. Over 100 acres of conserved land (no houses allowed) surround the property on two sides, while the other two sides are protected by deep woods that are part of the 24 acres. A quarter-mile driveway welcomes you to a world of mature landscaped gardens, private walking trails, a pole barn, a clay tennis court, and a writing cabin. A charming patio abuts an artesian well, which perpetually delivers pristine water over a sculpted stone fountainhead leading to two spring-fed ponds, one of which is 14 feet deep for swimming. At the heart of the property sits a beautifully crafted Huntington Homes cottage-style house. Expansive windows frame breathtaking views in every season, seamlessly connecting the indoors with the surrounding natural beauty. The home offers a first-floor primary bedroom, inviting open-concept living and dining areas, and a cozy library with a two-sided wood-burning fireplace, ideal for quiet evenings. The crown jewel of the home is the stunning screened porch-an idyllic setting for morning coffee, summer dinners, or simply soaking in the peaceful Vermont countryside. Adding even more value and flexibility, the property includes two income-producing opportunities: an Airbnb-ready detached seasonal guest cabin brimming with charm and character, and an 864-square-foot accessory dwelling unit above the garage with private access, ideal for guests, extended family, or additional rental income. Minutes from Vergennes and Middlebury for dining and charm; Burlington is 30 mins north for UVM and airport access; Lake Champlain is just 15 mins. More than a home, this is a lifestyle - a rare opportunity to own a very private Vermont retreat where comfort, natural beauty, and endless possibilities come together.

Listed by Jana Granzella of Four Seasons Sotheby's Int'l Realty

MLS Number 5059018

• Residential Single Family
• Full Bath 5
• Address 1204 Bailey Road
• Construction Existing
• Bedrooms 6

Exceptional Shrewsbury Estate: 97-Acre Legacy Property Offered for the discerning buyer, 1204 Bailey Road presents a unique opportunity to acquire a substantial 97-acre parcel in the heart of Shrewsbury. This 5-bedroom, 4-bath, 2-story colonial boasts 4,719 sq. ft. of well-maintained living space, characterized by quality craftsmanship and timeless design. The property distinguishes itself with significant infrastructure, including 82 acres under current use (agricultural and forest), ensuring lower tax implications. Notable upgrades to the property include a fully permitted tiny house conversion (septic, well, kitchen, and bath) providing versatile additional living quarters. Featuring 5 bedrooms, 4 bathrooms, 2 fireplaces, and expansive acreage, this property is a standout for those valuing privacy, land stewardship, and substantial square footage in a premier Vermont location. Schedule your private showing to explore the potential of this impressive land holding.

Listed by Gail Beardmore of Engel & Volkers Okemo

MLS Number 5073964

• Residential Single Family
• Full Bath 2
• Construction Existing
• Bedrooms 3
• Bathroom 3

Luxury Timber Frame Estate on 52+ Acres in Southern Vermont. This exceptional custom post-and-beam retreat is privately set amid rolling hardwood forestland, offering expansive mountain views, remarkable privacy, and a rare sense of peace and connection to nature. Designed for both elegance and efficiency, the home features solar panels with two Tesla Powerwalls for optional off-grid independence, paired with energy-efficient mini-split systems providing low-cost heating and air conditioning throughout the seasons. The residence offers three bedrooms and three baths, two versatile lofts, bonus room, gym and a spacious attached two-car heated and insulated garage, complemented by a flexible office, studio, or guest space above-perfect for today's work-from-home lifestyle, supported by high-speed internet in a truly serene setting. A newly designed chef's kitchen with premium appliances flows effortlessly into refined living spaces anchored by a Vermont stone fireplace, blending warmth, craftsmanship, and timeless Vermont character. Outdoor living is equally impressive, featuring a bluestone patio, in-ground heated pool with integrated hot tub, all surrounded by sweeping 360-degree mountain vistas and complete privacy-an idyllic environment for both entertaining and quiet retreat. The expansive acreage includes a separately deeded 10.53± acre parcel located at the intersection of Wilcox Hollow Road and Sandgate Road, featuring approximately 25 apple trees and a tranquil softwood stand, presenting the perfect opportunity for a second family residence or guest home. Ideally located near Manchester fine dinning and shopping while enjoying the benefit of affordable Sandgate taxes, the town offers full school choice from Pre-K through 12th grade. Four Vermont Ski resorts are within one hour, and both New York City and Boston are just three hours away. A rare Southern Vermont offering where privacy, community, and breathtaking mountain vistas exist in perfect harmony.

Listed by Margretta Fischer of Wohler Realty Group

MLS Number 5102622

• Residential Single Family
• Full Bath 10
• Address 4 Court Street
• Construction Existing
• Bedrooms 15

A rare offering on the Newfane village green: a Federal-style inn dating to 1787, set beside the Windham County Courthouse along VT Route 30 in one of New England's most photographed villages. The property combines eight guest accommodations (a mix of multi-room suites and private rooms, each with a private bath) with a three-bedroom, two-bath owner's residence featuring its own full kitchen and open living/dining space, positioned between the main building and a 1,700 sq. ft. two-story barn offering additional storage or development potential. Original architectural character remains intact throughout: brick fireplaces, exposed beams, original wood flooring, and a barrel-vaulted ceiling in the former ballroom. Public spaces include a great room, a parlor with banquet seating, a dedicated yoga studio, and a two-level veranda overlooking the green, town hall, and general store. Current Operation. An on-site restaurant and bar with a full commercial kitchen currently operates Thursday through Sunday, supported by weekly live music and a monthly open mic, giving the property an established food-and-beverage income stream alongside its lodging revenue. The inn has operated as both an individually-bookable lodging property and a whole-property rental for retreats, weddings, and group gatherings. Substantially renovated by the current owner since 2022, the inn is offered move-in ready, with an established brand, and online booking system. An incoming Buyer is welcome to transform the asset to suit their individual desires. The location offers exceptional four-season access: Mount Snow, Stratton, and Bromley are all roughly 30-40 minutes away, with swimming holes, hiking trails, covered bridges, and farm stands nearby, plus strong fall foliage draw. Newfane sits within convenient drive distance of Boston, Hartford, and New York markets - an ideal base for a spacious historic home or a hospitality-driven business. Also listed under commercial MLS #5094214.

Listed by Eben Viens of Berkley & Veller Greenwood Country

MLS Number 5060571

• Residential Single Family
• Village Quechee
• Construction New Construction
• Bedrooms 5
• Bathroom 4

The Aspen at Mountain Stream- To be built by Mountain Stream at Quechee Lakes, the 3,079-square-foot Aspen offers three levels of flexible, beautifully appointed living, with a single-bay tuck-under garage and a detached two-car garage. The main level centers on a great room that combines living, dining, and kitchen areas under double-height ceilings, anchored by a fireplace and opening to a deck ideal for entertaining or quiet mornings. A main-level primary suite, an additional bedroom with a walk-in closet, a mudroom, a mechanical room, and a half bath round out single-level living at its best. The second level adds a family room, full bathroom, and another bedroom. The lower level offers a family room, two more bedrooms, a full bathroom, and an optional mudroom or 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 millwork in every room. Built to perform as beautifully as it lives, the Aspen 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. A rare new construction opportunity in one of Vermont's most established four-season communities. This Is The Place.

Listed by Richard Higgerson of Higgerson & Company

MLS Number 5094747

• Residential Single Family
• Full Bath 3
• Construction Existing
• Bedrooms 5
• Bathroom 4

Welcome to one of South Burlington's most desirable settings, with views of Vermont National Golf Course to the north, the Green Mountains to the east, and nestled in a pastoral surrounding. This meticulously maintained and thoughtfully updated 5-bedroom home offers a rare combination of privacy, scenery, and convenience, blending timeless elegance with contemporary comfort. Recent improvements include beautiful hardwood flooring, a renovated primary bath, updated kitchen countertops, stainless steel appliances, central air conditioning, replacement windows, and a newer roof, allowing the next owner to move in and enjoy the home. Filled with natural light, the main level is designed for both everyday living and effortless entertaining. The welcoming foyer opens to gracious gathering spaces, including a living room with a gas fireplace and a sunroom bathed in afternoon sunshine. A private home office off the entry captures natural views and is the perfect space for work-from-home. The kitchen is the heart of the home, featuring a large center island, abundant workspace, quality finishes, and seamless access to the expansive rear deck. The large backyard connects to a protected landscape and is the perfect setting for summer entertaining, outdoor dining, or simply relaxing with family and friends. The inviting dining room suits both holiday celebrations and everyday meals. A first-floor guest suite with gas fireplace provides a comfortable and private retreat for visitors. Upstairs, the luxurious primary suite features a spa-inspired bath with soaking tub, walk-in shower, a gas fireplace for cool Vermont evenings, and scenic views from every window. Three additional bedrooms, a spacious full bath, and a flexible second office or playroom provide plenty of room for family. Nest smart home system and EV charging outlet make this residence highly efficient. Enjoy stunning sunrises and spectacular sunsets from this welcoming home, walking and biking trails close by.

Listed by Mary Palmer of Four Seasons Sotheby's Int'l Realty

MLS Number 5098540

• Residential Single Family
• Full Bath 3
• Address 55 County Road
• Construction Existing
• Bedrooms 3

Sited on a knoll with lovely views in every direction, this spacious, sun filled Contemporary home was built to last! Using the finest materials, commercial grade mechanics, and custom millwork, this home imbues quality throughout. An impressive fireplace with a wood burning insert anchors the Great Room with sweeping walls of windows integrating indoor and outdoor spaces, and French doors stepping out to a massive deck for entertaining. The kitchen is well suited with top quality appliances, granite counters and maple cabinetry. There is a primary bedroom ensuite, and a guest bedroom, and a study on the main level. Moving downstairs, the expansive spaces offer a variety of options as extended family space, or an in-law accommodation. There's a family room with fireplace, a large area for home gym, or play space. Two additional rooms for guest accommodation, a cedar closet, full bathroom, potential for a second kitchen. Outdoors, the property is magical with terraced perennial beds, mature trees and shrubs all selected to attract birds and butterflies. The oversized barn has three bays, a heated workshop/studio with bathroom, and ample loft space for hay/storage. Commercial grade generator, solar array. Lovely trail network lacing through the property. Easy access to Interstate, Woodstock, Hanover NH, skiing, golf and recreation.

Listed by Danny Kogut of Williamson Group Sothebys Intl. Realty

MLS Number 5081618

• Residential Single Family
• Full Bath 1
• Address 397 Fern Hill
• Construction Existing
• Bedrooms 5

Take a drive up Nichols Hill Road to Fern Hill and head to the very top of the long bending driveway to find a serene, picturesque artist's retreat 3 minutes from historic Dorset Village. Refreshingly private, quiet and secluded, drenched in natural light. With broad mountain vistas of Mother Myrick and Merck Forest, the top of the property backs gently into a beautiful private forest. The entire property has been carefully curated to encourage wildlife, a rewilding effort in place for 9 years, toxin and poison free. The large, pristine, spring fed swimming pond is the year round home to approximately 50+ healthy colorful Koi and overlooks a soft meadow bordered by old growth forest habitat, much to the delight of birds, butterflies, dragonflies, bees and abundant wildlife. The house is large, eclectic and rustic with a lodge feeling. A simple open concept design with lots of room and a farmhouse kitchen. Abundant windows throughout invite in and embrace the changing light and glistening view all day long. Distressed wide-plank floors, repurposed barn wood walls and beams, natural wood tray ceilings, curving wooden bookshelves and a curving staircase that leads to a half moon studio filled with natural light and sweeping views. Off the farmhouse kitchen find the very substantial screen porch and long sitting porch overlooking the gorgeous, vibrant, spring fed pond which reflects the changing light and soft scenery all day long. Natural beauty and peace, completely private and yet so close to everything.

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