Southern Vermont Luxury Listings

Scroll down to view all luxury listings in Southern Vermont listed below. Contact us if you have questions or would like to schedule a showing.

Upgrade Your Search - Create an account to save your favorite listings and to receive email updates for similar properties.

View all listings in Stratton Mountain too!

515 West Fields Road Manchester VT 05254

Manchester, VT515 West Fields Road

Price$6,900,000

Est. Mortgage: $/month

MLS Number 4974441

  • Residential Single Family
  • Property Type Single Family
  • Bedrooms 5
  • Bathroom 6
  • Acreage 5.15

Enduring values expressed in stone and wood! VERMONT CRAFTMANSHIP...A WORK OF ART!! Offering a private haven just minutes from downtown, in the heart of Manchester Village, nestled in the foothills of Equinox Mtn. is this rare and exceptional 5-bedroom, 6-bathroom home....The creative design of Architect Ramsey Gourd and Master Builder Mark Breen, well known as two of Southern Vermont's best, along with a dream team of highly skilled craftsmen, all passionate Masters of their own trade, and the results is quite simply....BREATH TAKING!!! The serpentine driveway is bordered by Maples, Birches, Pines and curves gracefully up to the cloistered court yard. Step through the front door into a wide foyer adorned with a gallery of floor to ceiling windows which further enhances the intimacy between the home's interior aesthetic and natural landscape. The home's showstopper has to be its jaw-dropping Great Room, thoughtfully designed as the heart of the home, this massive space accommodates kitchen, dining and living under a vaulted, 26 ft ceiling accented with hand-sawn wood beams. It features an incredible Chef's kitchen at one end and a floor-to-ceiling fire place at the other. The kitchen boasts a 17-foot book matched soap stone clad island seating for 6-8 and light filled sunny breakfast nook. With an outdoor kitchen, fire pit, built in water fall soaking pool, 5 verdant acres, tastefully blends with its idyllic valley setting, serenity is sublime!!!

Listed by Sunny Breen of Josiah Allen Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 7.02% last updated on May 16, 2024
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

25 Mountain Haunts Road Winhall VT 05340

Winhall, VT25 Mountain Haunts Road

Price$3,499,000

Est. Mortgage: $/month

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

$
$
%
$/month over payments
Federal 30-year interest rate: 7.02% last updated on May 16, 2024
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

73 Pine Road Dorset VT 05251

Dorset, VT73 Pine Road

Price$3,275,000

Est. Mortgage: $/month

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

$
$
%
$/month over payments
Federal 30-year interest rate: 7.02% last updated on May 16, 2024
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

4 Gold Medal Circle Stratton VT 05360

Stratton, VT4 Gold Medal Circle

Price$2,999,000

Est. Mortgage: $/month

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 starting in springtime 2024 with completion by the 2024/25 ski season. 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

$
$
%
$/month over payments
Federal 30-year interest rate: 7.02% last updated on May 16, 2024
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

1251 West Road Manchester VT 05255

Manchester, VT1251 West Road

Price$2,750,000

Est. Mortgage: $/month

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

$
$
%
$/month over payments
Federal 30-year interest rate: 7.02% last updated on May 16, 2024
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

743 Green Peak Orchard Road Manchester VT 05255

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

$
$
%
$/month over payments
Federal 30-year interest rate: 7.02% last updated on May 16, 2024
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

207 Brooks Lane Londonderry VT 05148

Londonderry, VT207 Brooks Lane

Price$2,475,000

Est. Mortgage: $/month

MLS Number 4971327

  • Residential Single Family
  • Property Type Single Family
  • Bedrooms 9
  • Bathroom 9
  • Acreage 69.2

This extraordinary, fully furnished property boasts an abundance of amenities and natural splendor. Revel in the awe-inspiring views and the tranquil swimming pond spread across these extensive 69 acres. Delight in the winding trails that lead to 1,235 feet of pristine West River frontage, providing year-round outdoor activities for all. With three distinct residences and a charming cabin, it offers ample space for everyone to convene while relishing their individual, private retreats. The main house, steeped in history dating back to 1820, is a delightful 3-bedroom brick farmhouse showcasing a generous 45-foot-long great room that seamlessly extends to a covered patio adorned with an awning, a idyllic setting for outdoor gatherings. The newly renovated kitchen, with granite countertops, serves as the heart of the home, combining modern elegance with timeless charm. The guest cottage features an additional three bedrooms, a cozy living room, and a well-appointed kitchen with an adjoining dining area. Adjacent to the guest cottage, a spa facility awaits, boasting a ground-level private gym, sauna, and an outdoor hot tub. Ascend to the second floor to discover two bedrooms, each with a private bathroom and a shared balcony. Nestled at the property's edge, overlooking the serene swimming pond with a beach, is a rustic cabin complete with a welcoming wood-burning stove and a lofted sleeping area. Ideally suited as a family compound, this retreat offers both separation and privacy

Listed by Timothy Apps of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.02% last updated on May 16, 2024
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

30 Stark Farm Road Winhall VT 05340

Winhall, VT30 Stark Farm Road

Price$2,350,000

Est. Mortgage: $/month

MLS Number 4953931

  • Residential Single Family
  • Property Type Single Family
  • Bedrooms 6
  • Bathroom 6
  • Acreage 5.6

Welcome to your mountain refuge in Winhall, Vermont! This extraordinary home offers an idyllic haven surrounded by nature. The 7,743 sq ft home is situated on 5 acres of picturesque land and presents the epitome of luxury living. With 6 bedrooms, 5.5 baths, and a myriad of incredible features, this home is a true masterpiece. As you step inside, you'll be captivated by the attention to detail and exquisite craftsmanship throughout. A stunning fireplace invites you to cozy up during the colder months, creating a warm and inviting ambiance. The spacious layout boasts an art studio, perfect for nurturing your creative spirit, while the garage comes equipped with an electric charging station. Embrace the spirit of competition on the basketball court or indulge in the serenity of the outdoors with an invigorating outdoor shower. Gather around the outdoor patio, complete with a cozy fire pit, where you can relax and unwind while sharing stories beneath the starlit sky. This home also offers an in-law suite, providing privacy and comfort for guests or extended family. Winhall school choice, proximity to Manchester and minutes from Stratton Resort, the location is convenient. With its unrivaled features, including the art studio, garage with charging station, amazing mudroom, wine cellar, basketball court, outdoor shower, and patio with a fire pit, this home is a true haven for those seeking both luxury and tranquility. Start your new chapter amidst the beauty of Vermont!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 7.02% last updated on May 16, 2024
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

3309 3321 Main Street Manchester VT 05254

Manchester, VT3309 3321 Main Street

Price$2,200,000

Est. Mortgage: $/month

MLS Number 4977864

  • Residential Single Family
  • Property Type Single Family
  • Bedrooms 11
  • Bathroom 9
  • Acreage 2.54

A rare gem and historically significant property in the picturesque setting of Manchester Village. Available for the first time in over 40 years! The embodiment of timeless elegance with a grand home and an adjacent carriage house, both on their own adjoining lots each with 1.27 acres. Boasting a total of 11 bedrooms, 6 full baths, 3 half baths and the main house includes a separate apartment with an additional kitchen. The main house is ready for full restoration and is the perfect canvas with almost limitless potential! Historical charm at every turn, this residence presents a unique opportunity to revive a piece of local history that once included Bromley Mountain Resort Founder, Fred Pabst Jr. and family. The move-in ready Carriage House with lots of light and charming character offers living space while renovations are underway and after, it could be used as a guest house, artist's studio, or private retreat! Enjoy the almost unheard of 2.54 park-like acres in the village of Manchester! The sprawling grounds provide a serene escape with mature trees and breathtaking mountain views perfect for outdoor activities, relaxation, and gatherings. A spectacular village location and positioned directly across from the renowned Ekwanok Country Club. Immerse yourself in the charm of the village atmosphere while enjoying convenient access to all of the area's best arts, dining, shopping, and endless recreational activities!

Listed by Greg Cutler of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.02% last updated on May 16, 2024
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

528 & 540 Nichols Hill Road Dorset VT 05251

Dorset, VT528 & 540 Nichols Hill Road

Price$2,160,000

Est. Mortgage: $/month

MLS Number 4965438

  • Residential Single Family
  • Property Type Single Family
  • Bedrooms 8
  • Bathroom 6
  • Acreage 187

On an Eastern hillside, between two ridgelines of the Taconic Range, is Goodman Farm. It is reminiscent of an earlier time with two cottages and an antique red barn set at the edge of a spacious hay meadow just outside the village of Dorset. The 187 acres abuts Rupert State Forest with panoramic views, perennial gardens, stone walls and a small pond. Crossing the stone bridge over Goodman Brook and continuing along a carriage width trail to an upper meadow, there is an exceptional building site, which offers complete privacy and spectacular mountain views. The houses include a 2,026 s/f farmhouse built in 1850 with 4 bedrooms and a 2,160 s/f cape built in the 1980s with 4 bedrooms. May Goodman, a former owner and the namesake, was one of the founders of the Dorset Players in 1927. Over the last half century, the owners have lovingly managed the land and created an extensive trail network through the woodlands suitable for walking, riding, mountain biking, or snow shoeing. The large and majestic trees, mostly maple, are a result of a soil rich in lime. According to the forester, these Eastern facing slopes of the Taconic are some of the most productive timberland in the state. Wild elderberries, black walnuts and apple trees abound, and it is an important wildlife corridor. The property is in current use and has a conservation easement with the Vermont Land Trust. 12 miles from Bromley and 24 miles from Stratton. 4 h from New York and 3 h 18 m from Boston.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 7.02% last updated on May 16, 2024
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

92 County Road Stratton VT 05155

Stratton, VT92 County Road

Price$2,100,000

Est. Mortgage: $/month

MLS Number 4988254

  • Residential Single Family
  • Property Type Single Family
  • Bedrooms 5
  • Bathroom 6
  • Acreage 5.18

COME HOME TO THIS EXQUISITE MOUNTAIN RESIDENCE, ONLY 5 MINUTES TO THE STRATTON SUNBOWL! EXCELLENT LUXURY RENTAL OPPORTUNITY! Sellers have successful Airbnb history, with all permits in place. 5 bedrooms, 5 1/2 baths, 2 living areas, gym, golf simulator & more provide space & fun for everyone! Set on a private, landscaped 5+ acre lot. Enjoy the outdoors on the expansive deck, take in the perennial gardens and stone wall. Enter into the foyer and be awed by the 29' towering ceiling accentuated with Douglas Fir beams in the living area just ahead. Stunning floor-to-ceiling, local stone fireplace! A grand wall of windows and glass-paned French doors to the expansive deck reveal a view of Pinnacle Peak. Large, thoughtfully laid out kitchen provides plenty of granite counter space, slate backsplashes, well-crafted cherry cabinets, stainless steel appliances including new double ovens and a 5-burner gas cooktop. The kitchen opens to a breakfast nook with French doors to the deck for easy access to the BBQ in warmer months. The 1st-floor primary suite boasts a gas fireplace, French doors to the deck, and a spacious marble bathroom with its own sauna. 2 ensuites upstairs with generous baths. The 4th & 5th bedrooms on the second level share a well-appointed bath. If there are times when you will not be using this gorgeous property yourself, rent with ease as all the current, necessary permits in place. Be one of the few truly luxury rentals available in the Stratton area!

Listed by Terry Hill and Lauren Behm of Berkshire Hathaway HomeServices Stratton Home

$
$
%
$/month over payments
Federal 30-year interest rate: 7.02% last updated on May 16, 2024
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

14 Old Ridge Road Winhall VT 05340

Winhall, VT14 Old Ridge Road

Price$1,975,000

Est. Mortgage: $/month

MLS Number 4988110

  • Residential Single Family
  • Property Type Single Family
  • Bedrooms 4
  • Bathroom 4
  • Acreage 1

Completely renovated mountain house with desirable layout. Located in the sought-after High Meadow neighborhood, this four bedroom, four bathroom property sits high on a perch, with clear views of Stratton's trails, and a view of Bromley from the front of the house. Rebuilt in 2023/2024, the home is all new, inside and out. The lighted driveway is a welcome entry on a snowy night. The entry foyer opens to the expansive living room with stone fireplace and kitchen/dining area. Massive kitchen island is the heart of this home. Bosch appliances in kitchen, including gas range with pot filler. The ample pantry storage and bar create dedicated spaces for an organized kitchen. Ride the shuttle bus home from the mountain and apres ski on the sunny deck. The game room is also on the main floor, with ample space for billiards and movie night. Bedrooms are oversized in this home. The primary suite has views of the mountain, and a luxury bathroom with heated floor. The mini-suite is a second en suite bedroom with double vanity and curbless walk-in shower. Two additional bedrooms access the hallway bathroom. A loft space with ladder adds intrigue. The two-car attached garage has direct entry to the mudroom and laundry room. This newly renovated home is ready for you.

Listed by Christiane Carroccio of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 7.02% last updated on May 16, 2024
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Broker Reciprocity 

Copyright 2024 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated May 18, 2024 6:38 PM EDT