Southern Vermont Luxury Listings

MLS Number 5005058

• Residential Single Family
• Property Type Single Family
• Bedrooms 6
• Bathroom 8
• Acreage 141.2

Luxurious 141 acre mountaintop retreat within Stratton Mountain Resort, stunning views of Stratton, Mt Snow, and Bromley. This architectural masterpiece blends comfort and elegance, with multi level interiors harmonizing living areas and en suite bedrooms. Inspired by the graceful arcs of skiing turns, the design features a dramatic entryway leading to a spacious living room and library. An 18-foot stone fireplace and expansive windows flood the space with natural light and breathtaking views. The entry leads to a gourmet kitchen with a large eat-in dining and a formal dining room, perfect for entertaining. The home boasts 6 en suite bedrooms, an expansive primary suite with an office, two custom walk-in closets and a cedar closet. A custom-built bunk room with locker-style cubbies adds playful sophistication. A light-filled hallway connects the upper and lower levels, linking bedrooms, a home theatre, and living areas, enhancing the open and airy feel. Additional amenities include a golf simulator and a movie theatre. Outdoors enjoy mountain views, perennial gardens, natural stone accents, and a bluestone walkways. In warmer months, luxuriate in the gunite pool and hot tub while soaking in views. A gym in the detached three-car garage is perfect for workouts. Tennis and pickleball courts offer additional outdoor activities. This property is a sanctuary where architectural elegance meets mountain tranquility. Discover the epitome of luxury at this stunning mountain retreat.

Listed by Lisa Sullivan of Four Seasons Sotheby's Int'l Realty

MLS Number 5006694

• Residential Single Family
• Property Type Single Family
• Bedrooms 5
• Bathroom 6
• Acreage 7.97

Welcome to High Fields: A Custom-Built Sanctuary in Southern Vermont. Arrive via a private, maple-canopied lane to discover tranquility & breathtaking mountain views. This home features exquisite Vermont oak flooring, custom woodwork & cabinetry, & a charming brick-floored mudroom with garage access & a stairway to a one-bedroom apartment. The heart of the home, the kitchen, is a culinary dream with large windows, floor-to-ceiling cabinetry, a center island, & a spacious pantry. The dining room seats twelve comfortably, & the living space is perfect for entertaining or cozy nights by the wood-burning fireplace. Seamless indoor-outdoor flow is achieved with terraces & a covered porch ideal for alfresco dining. The main floor primary suite boasts a luxurious shower, custom closet, private terrace, vaulted ceiling, & a cozy gas fireplace. The second floor offers two guest bedrooms with a Jack & Jill bathroom, a workout space, & an additional laundry room. The upper primary suite is a private oasis with stunning mountain views, a spacious closet, & a spa-like bath. The lower level features spaces for media, reading, & entertaining, including a wine cellar & full bath. Additional features include a heated garage, geo-fencing, security & door cameras, an Ecobe smart thermostat, & a whole-house generator. High Fields is designed for sophisticated living, blending elegance, comfort, & functionality. Conveniently located just 1 mile from town amenities & 3 hours from Boston & NYC.

Listed by Andrea Kaplan of Four Seasons Sotheby's Int'l Realty

MLS Number 5011880

• Residential Single Family
• Property Type Single Family
• Bedrooms 5
• Bathroom 4
• Acreage 53

Boorn Brook Farm combines the rich character of history and the comfort of contemporary living with complete privacy. Established in the late 1700s, the estate near Manchester Center offers stunning views of the Mt. Equinox and the Taconic Range. Surrounded by the Green Mountain National Forest, it creates a peaceful haven that balances the old and the new. For over 50 years, Marion Gould Pleissner lived at the Plaza in New York City and summered here while her husband, celebrated artist Ogden Pleissner, used the barn as his studio-his works now hang at the Met, Shelburne Museum and in private collections. The 1790s farmhouse and 1820s barn underwent extensive renovations by Boston architects Judge, Skelton, Smith. The farmhouse was thoughtfully restored, while the barn was transformed into two living spaces. Modern updates, including new utilities and underground infrastructure, were discreetly integrated to preserve the pristine vistas. The Great Room of the Barn have seen many lively gatherings over the years. Today, this multi-generational sanctuary remains a tranquil retreat, bordered by Bourn Brook and encircled by the GMNF's Lye Brook Wilderness Area. The property retains its pastoral allure with goats grazing the fields and timeless pleasures like fly fishing, hiking and swimming. Currently serving as a family compound and wedding venue, the property holds an Act 250 permit for up to 43 cabins. For more details, refer to the commercial listing.

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

MLS Number 4971483

• Residential Single Family
• Property Type Single Family
• Bedrooms 5
• Bathroom 6
• Acreage 9.4

Hidden at the top of one of Dorset's quiet lanes you will discover the epitome of timeless elegance & modern luxury in this meticulously renovated 5-bedroom, 6-bathroom 1941 Colonial. On a sprawling 9.4-acre estate, this enchanting property offers a harmonious blend of history and sophistication. 6 fireplaces evoke a warm and inviting ambiance, creating the perfect backdrop for cozy and memorable gatherings. The post & beam great room addition is a breathtaking architectural achievement. With soaring ceilings, exposed beams, and expansive windows; a seamless connection between the interior and the natural beauty of the exterior landscape. Outside, tastefully landscaped grounds beckon you to explore. Stone walls add character, while expertly crafted gardens bloom with color. The tranquil brook that meanders through the property offers a soothing soundtrack to your daily life. A short distance from the main residence you arrive at a remarkable stone and timber barn designed for all your recreational needs, by noted architect, Ramsay Gourd. Continuing down the path you arrive at the private, two bedroom/two bath, elegantly appointed guest cottage, with rear private patio to enjoy some quiet down time. Located close to the main house is the free form pool and exquisite pool house. This property is not just a home; it's a lifestyle, a retreat; an opportunity to own a piece of heaven. Don't miss your chance to make this exquisite retreat your own. More information attached.

Listed by Richard Slocum of Four Seasons Sotheby's Int'l Realty

MLS Number 5012831

• Residential Single Family
• Property Type Single Family
• Bedrooms 5
• Bathroom 7
• Acreage 21.53

This extraordinary multi-generational Vermont retreat offers the ultimate in luxury and breathtaking mountain vistas. Nestled on a private 21+ acre estate at the end of a quiet drive, the property boasts sweeping 270-degree views of the surrounding mountains, including the trails of Stratton Mountain Resort. The professionally designed and decorated home features over 10,000 square feet of living space, providing ample room for comfortable and elegant living. The spacious great room, with its soaring 25-foot ceilings, stone fireplace, and expansive windows framing the majestic views, is an ideal gathering space for family and friends. The gourmet kitchen, featuring reclaimed beams and a massive island, is a chef's dream. Step outside onto the stone terrace to enjoy the peaceful ambiance and stunning scenery, or watch the snow groomers at work on the slopes. The primary suite is a true oasis, with two walk-in closets, breathtaking views, and a luxurious en-suite bathroom featuring a walk-in shower and soaking tub. Upstairs, you'll find four generously sized guest bedrooms and a bonus room above the garage. The mudroom and two-car garage provide plenty of space for your outdoor gear, making it easy to enjoy all that the Vermont mountains have to offer. This exceptional property is perfect for those seeking a private, luxurious, and multi-generational retreat. Don't miss this opportunity to own a truly remarkable piece of Vermont real estate

Listed by Robin Apps and Margaret McMahon of Four Seasons Sotheby's Int'l Realty

MLS Number 4945895

• Residential Single Family
• Property Type Single Family
• Bedrooms 6
• Bathroom 7
• Acreage 40.8

Your 40 acre Mountain Playground and Stratton Mountain Estate is nothing short of EXTRAORDINARY! Recently expanded and renovated this grand lodge now boasts 4 en suite bedrooms, three stone fireplaces, huge lodge room with large beams, walls of glass and VIEWS, VIEWS, VIEWS. Gourmet kitchen, plus a 2 BR/2BA Guest House - each with unrivaled views of Stratton Mountain's trails.You'll be captivated by commanding southerly views of Stratton Mountain, surrounding ridge lines and sunset views to the west. This property is without comparison and the last rare parcel of this size near the resort. Enjoy a world of privacy and tranquility. Just minutes to the Base Lodge, you'll come home to endless outdoor fun. Bring your ATVs, snowmobiles and in summer there's a pond and tennis court. Patios, Stonework, outdoor spaces enhance the stunning location. Situated in the heart of everything the region has to offer throughout the seasons. World Class professional theater, the Manchester Music Festival, The Dorset Summer Equestrian Festival. Hiking, biking, kayaking, shopping and dining. Fall foliage, first tacks on powder days and the glorious Green Mountain Summers beckon. This one of a kind property has the essence of a true mountain lodge, set into its surroundings with a tranquil and peaceful vantage point. Adventure is at your doorstep.Additional land parcels available. Make plans to visit this newly expanded and renovated property. 8 Bedroom septic. You'll be enthralled!

Listed by Kim Morgan-Wohler of Wohler Realty Group

MLS Number 4994366

• Residential Single Family
• Property Type Single Family
• Bedrooms 6
• Bathroom 4
• Acreage 6.21

This custom-designed modern farmhouse in Dorset, Vermont was completed in 2023. Soaked in natural light, this sunny home may be everything you are looking for. Spectacular mountain and valley views from this private location, yet minutes from all the best of Southern Vermont. Every detail is completely planned and executed - from the Marvin Ultimate windows to the Waterworks bathtub, the finishes and fixtures are all quality selections. The property consists of a four-bedroom home and a two-bedroom guest cottage on 6 acres. A sophisticated Vermont style, the open living space with white oak floors is filled with light and character. The wood ceiling in kitchen area brings dimension, and the custom mahogany doors exhibit superb craftsmanship. The master suite is on the main floor with custom walk-in closets, a Danby marble bathroom, and its own mahogany deck. The second level features three bedrooms and a full bathroom. The guest cottage was renovated in 2002. Backup generators for both main house and guest house. Radiant heat is provided throughout, and supplemental mini-splits provide air conditioning. Oversized two-car garage attached to main house. 11 minutes to skiing at Bromley, 8 minutes to dinner in Manchester, and 8 minutes to the Dorset Farmers Market. This location has been coveted for years, and now it can be yours.

Listed by Christiane Carroccio of TPW Real Estate

MLS Number 4987337

• Residential Single Family
• Property Type Single Family
• Bedrooms 6
• Bathroom 7
• Acreage 2.4

4 Gold Medal Circle at Stratton, Vermont's newest and most prestigious address, just a 1 minute drive to Stratton's Sun Bowl, with construction coming soon. The 4,845 square foot home boasts expansive views of Stratton's trails along with 6 luxurious bedrooms, 6+ bathrooms, gourmet kitchen complete with high-end appliances and finishes, suspended high efficiency fireplace, and a thoughtfully designed floor plan for a home that promises to be the epitome of modern mountain living. The 2,816 square foot walkout basement with walls of glass and mountain views can be customized and provides easy access to outdoor entertaining space. Gold Medal Circle is an enclave of custom homes, the perfect location for establishing your own retreat with meticulous attention to comfort, style, and elegance. You'll enjoy the adjacent 73 acres of common land deeded for preservation for hiking, snowshoeing, or just basking in the beautiful natural setting. The developer is a master builder with 37 years of experience, specializing in luxury custom homes with superior quality energy efficiency using the latest modern technology, healthy indoor environments, and state of the art thermal protection. Buyers have the option to select finishes and amenities along with working hand-in-hand with the builder and designer to create a spectacular home in which to enjoy a superior mountain lifestyle.

Listed by Deborah Hanst and Jeffrey Sheehan of Cummings & Co

MLS Number 5008469

• Residential Single Family
• Property Type Single Family
• Bedrooms 5
• Bathroom 5
• Acreage 13.79

Modern Magic in Manchester! Live your Vermont dreams on nearly 14 enchanting acres. This extraordinary, contemporary home is a masterpiece of design and luxury. With unparalleled privacy and breathtaking views of Mt. Equinox, indulge in spacious elegance with 5 bedrooms and 4.5 bathrooms spread across 3 levels. The primary suite, nestled on the main level, invites relaxation with wrap-around windows showcasing your personal mountain panorama. The gourmet kitchen, a chef's dream, boasts a Sub Zero 48” Pro refrigerator, Wolf range, Meile dishwasher and wine fridge. Gather loved ones around the grand living room's crackling fireplace and watch the snow fall across the mountaintops, creating unforgettable memories or relax in the sunroom, featuring a new, Jotul gas fireplace. Embrace the outdoors and immerse yourself in nature with a serene pond, rejuvenating hot tub, and expansive deck, perfect for summer entertaining. Endless possibilities await. The expansive partially finished basement offers a canvas for your imagination. Create a home theater, wine cellar, or additional living spaces to suit your lifestyle. Live the ultimate luxury lifestyle with your workout room, sauna, and attached three-car garage that complete this extraordinary package. New hot tub, new generator, new alarm system, new wood flooring in most rooms. This is more than a home; it's a sanctuary. Your Vermont escape begins here.

Listed by Tg Glazer of Winhall Real Estate

MLS Number 5001428

• Residential Single Family
• Property Type Single Family
• Bedrooms 4
• Bathroom 5
• Acreage 12.67

Welcome to 376 Windward Hill: A sprawling estate with spectacular views of the Taconic and Green Mountain Ranges. Nestled in the heart of Southern VT, this extraordinary property offers unparalleled panoramic views. A grand entrance unfolds as you drive through the expansive 12-acre scenic grounds, where a private trout pond adorned with a tranquil waterfall sets a serene tone. Inside, elegance and comfort await with herringbone brick and hardwood flooring that leads you to a sweeping serpentine staircase, ascending to the main floor. A magnificent two-story stone fireplace in the open double living room awaits, creating an ideal space for entertaining. Flow seamlessly from the spacious seating areas to the dining room, which opens to a screened-in porch and expansive wrap-around deck, perfect for enjoying the breathtaking mountain vistas. The well-appointed cook's galley kitchen features a comfortable bar area, ample cabinet storage including a butler's pantry, and modern appliances. The primary suite is a private sanctuary with sweeping mountain views, direct access to the deck and luxurious spa-like bathroom with a jacuzzi tub and steam shower. Down the hall, there are 3 generously sized bedrooms with adjacent bathrooms, plus an office that could serve as an additional bedroom. The lower level is a haven of functionality, featuring an exercise room, a builder's workshop, a spacious office or family room, and floor-to-ceiling closets. All minutes from Manchester and Dorset.

Listed by Sean Dillon and Liz Moore of Four Seasons Sotheby's Int'l Realty

MLS Number 4976603

• Residential Single Family
• Property Type Single Family
• Bedrooms 9
• Bathroom 7
• Acreage 7.05

Welcome to Forever Farm, a landmark property & location in Manchester Village, VT. This well maintained home is ready for family and friends - whether it be entertaining a large dinner crowd or relaxing on the front porch with a good book, this home is so versatile. The main house is comprised of 6 bedrooms, gorgeous cooks kitchen and several inviting living room spaces. The well manicure grounds give a pop of color year-round, whether it be the perennial gardens in the stone walls, colorful fall foliage on the maples, birches and fruit trees, snowcapped mountains or the spring time flowers, this home makes any season a delight. The separate carriage house with 3 bedrooms & 2 baths is a great retreat for guests. Horse stalls and outdoor riding ring, three bay heated garage, home gym & multiple ponds! This home awaits its new owner, to love and continue the tradition of Southern Vermont living. Property is being offer fully furnished & completely turn key.

Listed by Andrea Kaplan of Four Seasons Sotheby's Int'l Realty

MLS Number 4970555

• Residential Single Family
• Property Type Single Family
• Bedrooms 5
• Bathroom 4
• Acreage 7.9

Beautifully designed to capture spectacular views of mountains and sunsets, this exceptional residence is situated on 7.9 open acres with guest house/barn just off of Overlook Drive in Green Peak Orchard. A traditional covered porch welcomes you as you are drawn into the view from every gathering space; living room, billiard room and gourmet kitchen. Wonderful spaces for entertaining. Kitchen features oversized island, 2 dishwashers - Bosch and Wolf appliances. Formal dining room opens to living area with wide pine floors, fireplace, walls of windows and sunny exposure. Exceptional outdoor spaces with large patio, gardens and meadow. The second floor, with en suite primary, additional bedrooms and oversized media room also doubles as an in house work-out space. It's perfect for movie night, watching the game or working out ! The quintessential Vermont red barn is the guest house, complete with open living/dining/ kitchen with one bedroom , bath and den. Exceptional construction, efficient mechanicals, and several special features. Central AC, Generator, cedar closet. Mudroom and oversize garage with storage and work space. Main house has 2 car garage and Barn has 1 garage bay plus an abundance of storage space.Showings begin on Wednesday 9/20.

Listed by Kim Morgan-Wohler of Wohler Realty Group