Luxury Properties

Southern Vermont is home to some of New England’s most beautiful luxury real estate and your search begins here. Within a 3-4 hour drive of the northeast's major metro and suburban areas, southern Vermont is home to four-season fun, numerous ski areas, fine dining and shopping, great schools and more.

370 Fischer Lane Jamaica VT 05343

Jamaica, VT370 Fischer Lane

Price$9,950,000

Est. Mortgage: $/month

MLS Number 5015744

  • Residential Single Family
  • Full Bath 7
  • Address 370 Fischer Lane
  • Construction Existing
  • Bedrooms 6

Accessible, but miles from the everyday. Camp Endo's mountain kingdom is minutes from Stratton Mtn. with a 21st century take on a mountain timberframe home, and 417+/- acres threaded with trails and ridgelines. Ski your own glades and rip the eight miles of custom-designed mountain biking terrain, or just pause to enjoy the vast views. The house reimagines a rustic lodge with classic wood, bark and stone detailing combined with complete comfort, great light and welcoming spaces. The property was featured in the book Rustic Living by Ralph Kylloe as one of the great rustic style homes in the U.S. The 13,393-square-foot home has an open floor plan, massive stone great room fireplace, chef's kitchen and 6 bedrooms en suite, each with magnificent mountain views. Off the kitchen and great room is a screened-in porch and large deck with an outdoor stone fireplace to soak in the panoramic southerly green mountain views. Smaller gathering spaces include a corner office, gym/spa, meditation room and 22-seat home theater. Camp Endo's extensive trail network provides a daily dose of rugged, natural beauty for mountain biking, walking or snow shoeing and playful options include a paintball course and a six-foot square chessboard. The adjacent barn houses a fully appointed 2 bedroom guest suite, 3-bay garage and half-basketball court with surround sound. Next to the apple orchard is a large swimming pond with views of Stratton Mtn. The property has renewable solar and wind energy.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* 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

3800 Weston Andover Road Andover VT 05143

Andover, VT3800 Weston Andover Road

Price$8,300,000

Est. Mortgage: $/month

MLS Number 5015743

  • Residential Single Family
  • Full Bath 1
  • Construction Existing
  • Bedrooms 8
  • Bathroom 8

A magnificent 10,062 SF family compound. Custom built, it comes fully furnished and equipped for immediate occupancy, featuring 7BR, 8BA, a separate 1BR guesthouse and office, a furnished and heated writers cabin overlooking the Connecticut River Valley, and an equipment barn, all situated on 384 acres of pristine hardwood forest, accessed by an 1800' paved driveway. Anchored by miles of woodland trails and located in Andover, Vermont, the offering includes outdoor sculpture and artwork, historic rock walls, open fields and building ruins from early settlers, along with direct access to the VAST trail system for winter trail riding. The main house features a soaring 2-story fireplace, post and beam timber frame construction, and a chef's kitchen with double appliances, Viking 60” cooktop and wood-fired interior pizza oven, while a reading loft and library add a calming vibe to the outdoor view. The primary suite has a 2BR, 2BA configuration on the main floor with 5 additional bedrooms with en suite baths. There are 6 garage bays supplied with commercial sinks, a 21' x 35' open design gym and exercise suite, and a media room with custom pool table and walkout to the ground floor. Designed for 4-season recreation, privacy and small batch maple syrup production, the hardwood forest, mountain trails, open fields, and additional access from another town road offer unlimited possibilities for the discerning buyer looking for a lifestyle in Vermont's iconic Green Mountains.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* 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

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
  • Full Bath 3
  • Address 515 West Fields Road
  • Construction Existing
  • Bedrooms 5

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: 6.89% last updated on Feb 6, 2025
* 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

454 Mountain Road Stratton VT 05155

Stratton, VT454 Mountain Road

Price$6,700,000

Est. Mortgage: $/month

MLS Number 5005058

  • Residential Single Family
  • Full Bath 5
  • Address 454 Mountain Road
  • Construction Existing
  • Bedrooms 6

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* 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

64 Tamarack Road Stratton VT 05155

Stratton, VT64 Tamarack Road

Price$5,250,000

Est. Mortgage: $/month

Active With Contract

MLS Number 5021231

  • Residential Single Family
  • Full Bath 10
  • Address 64 Tamarack Road
  • Construction Existing
  • Bedrooms 9

Discover this Extraordinary Stratton Mountain Resort Tamarack Heights premier trailside residence. Situated on a sprawling 1.4-acre trailside lot, this property exudes unassuming grandeur from the moment you enter its magnificent great room with a soaring two-story fireplace and floor-to-ceiling windows that frame breathtaking panoramic views of Stratton Village and the surrounding mountains. Architecturally inspired by Vermont's historic covered bridges, the design seamlessly blends with its natural surroundings, snow covered trails and exceptional views from every vantage point. The use of natural materials with custom stonework and woodwork throughout features impeccable craftsmanship. The dining area and gourmet kitchen with stone countertops, oversized island and superior appliances is surrounded by long range views and a front row seat to seasonal fireworks. Expertly designed, this home offers an unrivaled 9+bedroom suite floorplan with unmatched gathering spaces. The primary suite is privately situated with fireplace and substantial walk-in closet, private deck and views, views, views, and remaining suites are located throughout the 7498SF design. Most importantly, you'll ski out onto the trails and back from your own ski lodge room; complete with fireplace, ski lockers, boot dryers, 2nd kitchen and tables for lunch and apres ski! No detail in planning for a mountain lifestyle has been overlooked. This is the epitome of Stratton Mountain living in Vermont's Green Mtns.

Listed by Kim Morgan-Wohler and Britt Wohler of Wohler Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* 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

62 Moon Shadow Drive Ludlow VT 05149

Ludlow, VT62 Moon Shadow Drive

Price$4,999,000

Est. Mortgage: $/month

MLS Number 5027315

  • Residential Single Family
  • Full Bath 4
  • Address 62 Moon Shadow Drive
  • Construction Existing
  • Bedrooms 5

This unique SKI-ON, SKI-OFF mountain home is a one of a kind; an icon of slope side living on Okemo since it was constructed on the Moon Shadow ski trail in 2003. With its seven wood burning fireplaces and extensive stonework both inside and out, this home is as comfortable as it is extraordinary. The overall impressive design delivers an unparalleled, genuine log construction with its wide chinking and broad hewn timbers. Walking through this home is an exploration of grand spaces as well as intimate and luxurious niches such as the great room with soaring timber ceilings and the elevated soaking tub in the primary bath with its magnificent view. There are three private ensuites, including guest quarters with its own private entrance and great room as well as an king-sized bedroom, of course, with another fireplace. This home is a perfect allocation of space and light and every inch has been thoughtfully considered. The contrast of rustic and refinement is perfectly represented in the Gourmet kitchen with its wood burning stone fireplace and high-end appliances. This GREAT home is all set-up for income producing, year-round luxury rentals. There is no shortage of fun to be had with the oversized hot tub on the stone patio overlooking the ski trail, the open and airy loft with billiard table and the generous game room. Too many upgrades, renovations to mention. This home is gorgeous and ready for you to enjoy! This is a very impressive MUST SEE property.

Listed by Elissa Scully of Mary W. Davis Realtor & Assoc.,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* 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

527 Benson Road Manchester VT 05255

Manchester, VT527 Benson Road

Price$4,975,000

Est. Mortgage: $/month

MLS Number 5011880

  • Residential Single Family
  • Full Bath 1
  • Address 527 Benson Road
  • Construction Existing
  • Bedrooms 5

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* 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

318 Spring Hill Lane Dorset VT 05251

Dorset, VT318 Spring Hill Lane

Price$4,875,000

Est. Mortgage: $/month

MLS Number 4971483

  • Residential Single Family
  • Full Bath 6
  • Address 318 Spring Hill Lane
  • Construction Existing
  • Bedrooms 5

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* 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 Morning Star Drive Ludlow VT 05149

Ludlow, VT4 Morning Star Drive

Price$3,850,000

Est. Mortgage: $/month

MLS Number 5017498

  • Residential Single Family
  • Full Bath 2
  • Address 4 Morning Star Drive
  • Construction Existing
  • Bedrooms 5

One of the most coveted homes on Okemo is ready for its new owner. Welcome to a spectacular, Montana lodge-style retreat nestled in a prime slopeside location on Okemo Mountain, adjacent to Solitude Village Day Lodge. This breathtaking ski-in/ski-out home sits at the top of Daybreak Trail, offering unrivaled mountain views in every direction. Crafted from Montana lodge pole pine and Vermont stone, this five-bedroom estate blends rugged elegance with luxurious comfort. Step inside to a spacious haven, complete with two grand stone fireplaces and an open-concept design. The chef's kitchen, with high-end appliances and a commercial hood, has access to the stone fireplace featuring a pizza oven. The open concept allows a seamless flow into the living and dining areas, creating the ideal apres-ski gathering space. This home offers endless relaxation with its expansive decking, six-person salt water hot tub, Danish sauna, steam room, and an outdoor fireplace. Each bedroom is an oasis of privacy, and all have an en-suite bath. The primary bedroom has dual walk-in closets and views both up Okemo and to the valley below. With immediate access to the Solitude chairlift and steps from Solitude Village's amenities and seasonal restaurant, this one-of-a-kind home delivers the ultimate mountain lifestyle. Experience unparalleled luxury, convenience, and craftsmanship at this slopeside residence. Visit the Okemo real estate community today. Taxes are based on current town assessment.

Listed by Joseph Karl of William Raveis Vermont Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* 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

348 Turtle Hill Road Ludlow VT 05149

Ludlow, VT348 Turtle Hill Road

Price$3,650,000

Est. Mortgage: $/month

MLS Number 5020831

  • Residential Single Family
  • Full Bath 3
  • Address 348 Turtle Hill Road
  • Construction Existing
  • Bedrooms 5

This custom timber frame home, is a stunning embodiment of traditional barn-style construction that seamlessly blends modern comforts with rustic charm. The private 13.58 acres is perched at the end of a secluded road, offering breathtaking 180-degree mountain views over to Okemo. Visiting this property in person is the only way to appreciate its intricate construction and the magic of its view. Every hour is like having a birds eye view of mother nature at work. The beating heart of the home is a magnificent freestanding fieldstone fireplace, creating a warm cozy spot for gatherings after a day spent on the slopes. All chefs, young and old, will love the open exhibition style kitchen equipped with high-end appliances and the massive granite island perfect for everyone to gather around and pitch in. The open loft area provides a unique vantage point overlooking the expansive living space below, enhancing the home's airy feel. Discover the hidden gem of a cupola-reminiscent of a barn's hayloft-that serves as a serene getaway, ideal for yoga, meditation, or simply curling up with a good book. Complete with a three-car oversized garage, this remarkable property is an unparalleled escape that harmonizes luxury and tranquility. Enjoy ultimate comfort with the convenience of a whole-house generator and the peace of mind that comes with underground utilities. Consider this your invitation to experience this gorgeous home

Listed by Suzanne Garvey and Matthew Bellantoni of Mary W. Davis Realtor & Assoc.,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* 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

73 Pine Road Dorset VT 05251

Dorset, VT73 Pine Road

Price$3,275,000

Est. Mortgage: $/month

MLS Number 4994366

  • Residential Single Family
  • Full Bath 3
  • Address 73 Pine Road
  • Construction Existing
  • Bedrooms 6

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: 6.89% last updated on Feb 6, 2025
* 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
  • Full Bath 2
  • Address 4 Gold Medal Circle
  • Construction Pre-Construction
  • Bedrooms 6

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* 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

1199 Okemo Ridge Road Ludlow VT 05149

MLS Number 5028825

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

Within the picturesque landscape of Solitude Village at Okemo, this three-level home offers a blend of comfort and style with easy ski/on ski/off access. As you enter, you are greeted by an open concept living space that exudes warmth and sophistication. The living area features a beautiful stone fireplace, perfect for gathering around after a day on the slopes, while large windows flood the space with natural light. The well-appointed kitchen is complete with modern appliances, ample counter spaces and a charming dining area that invites family and friends to share memorable meals together. Whether you are whipping up a hearty breakfast or preparing an evening dinner, this kitchen is designed for functionality and ease. The upper level boasts 2 bedrooms, an ensuite private primary bedroom/bath (ensuring a sanctuary for relaxation), and a bonus room that could be used as an office, all overlooking the ski trail. The lower level of the home is an entertainment haven. This space is perfect for unwinding after a long day whether enjoying a movie night or soaking in the inviting hot tub. Two additional bedrooms, bath and laundry area await your guests on this level.The main level mudroom with direct slope access is large with custom benches and cubbies.The attached 2 car garage has plenty of room for storage which allows extra parking spaces when the home is filled with friends. With its thoughtful design and inviting ambiance this home is a true escape where memories are made.

Listed by Elissa Scully of Mary W. Davis Realtor & Assoc.,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* 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

19 Old Town Road Winhall VT 05340

Winhall, VT19 Old Town Road

Price$2,780,000

Est. Mortgage: $/month

MLS Number 5012831

  • Residential Single Family
  • Full Bath 3
  • Address 19 Old Town Road
  • Construction Existing
  • Bedrooms 5

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* 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

113 North Village Road Ludlow VT 05149

MLS Number 5012032

  • Residential Single Family
  • Full Bath 1
  • Construction Existing
  • Bedrooms 5
  • Bathroom 6

This beautiful and very spacious newly constructed home, with energy efficient upgrades, has over 6,000 square feet of living space on three levels. Within walking distance to the slopes, located close to the Base Lodge area, this home has everything a ski home needs. Enter through the carefully crafted front door into one of the two mudrooms, or through the two car garage or by the side mudroom and you will see walls of three-pane glass picture windows (for insulation and acoustics) looking at your mountain range view. An open floorplan with vaulted ceilings, large chef's kitchen with an island, hickory flooring, dining and living room with a fireplace that has a metal insert with internal blowing. There are 5 and a half bathrooms, plenty of spacious bedrooms, and a beautiful media/recreation room with a wall of windows, vaulted ceiling and view, which will be a fun space for entertaining guests! A hot tub, and covered porch/deck add to the exterior ambiance. Radiant heat on the ground floor, air recuperation system, 2x8 walls, foam insulation in walls and roof and more!

Listed by Elissa Scully of Mary W. Davis Realtor & Assoc.,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* 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$2,500,000

Est. Mortgage: $/month

MLS Number 4976603

  • Residential Single Family
  • Full Bath 4
  • Address 1251 West Road
  • Construction Existing
  • Bedrooms 9

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: 6.89% last updated on Feb 6, 2025
* 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
  • Full Bath 4
  • Construction Existing
  • Bedrooms 5
  • Bathroom 5

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, offers 4 bedrooms/3 full baths, one newly added and under construction. A wonderful ensuite primary features spacious walk in closet dressing room and views. The oversized media room doubles as an in house work-out space but could also become a bunk room/playroom. 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. Quintessential Vermont, location, beautiful home, barn guest house and and year round views.

Listed by Kim Morgan-Wohler of Wohler Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* 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

18 Rocky Dell Road Winhall VT 05340

Winhall, VT18 Rocky Dell Road

Price$2,450,000

Est. Mortgage: $/month

MLS Number 5011900

  • Residential Single Family
  • Full Bath 5
  • Address 18 Rocky Dell Road
  • Construction Existing
  • Bedrooms 7

Welcome to this stunning Contemporary Mountain Estate on 26 acres where luxury, privacy and nature converge.Offering more than a home-It's a lifestyle with the perfect blend of sophistication, comfort & natural surroundings. Ideally located just minutes to the Stratton Mountain Resort or the Green Mountain National Forest, easily accessed from Kendall Farm Road. Enjoy the mountains & the outdoors from your doorstep. The main residence is nothing short of dramatic w/open spaces, cathedral and vaulted ceilings, walls of windows, wood floors &4 masonry fireplaces.The use of natural materials creates a contemporary and warm ambiance. Multiple gathering spaces on the main level open to a wonderful gourmet kitchen with island and multiple dining areas bringing ease to entertaining friends and families during any season.Floorplan offers 5 bedrooms/4.5 baths with multiple bedroom suites privately situated on three levels.The primary suite boasts complete privacy with office area, walk in closet and expansive stone and tile baths.A lower level media and game room is designed for billiards or ping pong with fireplace and apres ski wet bar.Recently renovated, the Carriage House features striking 1260SF guest quarters with 2 bedrooms and bath. Situated within the acreage is a separately deeded 10 acre building lot and pond. Expansive deck, stone patio, multiple garages, landscaped and naturally wooded, this property is complete for you Vermont Getaway! Hike, swim, ski, and snowmobile.

Listed by Kim Morgan-Wohler and Britt Wohler of Wohler Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* 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

662 Howe Farm Road Jamaica VT 05343

Jamaica, VT662 Howe Farm Road

Price$2,399,000

Est. Mortgage: $/month

MLS Number 4972272

  • Residential Single Family
  • Full Bath 1
  • Address 662 Howe Farm Road
  • Construction Existing
  • Bedrooms 4

Discover this renovated timber frame home nestled on 366 acres of private land. Offering a seamless blend of historic character and modern comfort, this 4 bedroom plus office, 4 and a half bathroom home showcases attention to detail. The gourmet kitchen, inviting living spaces, bonus game room and home gym are complemented by a sunlit dining space with a greenhouse sunroom, adding a touch of nature to your daily life. Multiple bedrooms give everyone in your party a private space to relax after a long day exploring the outdoors. Step outside to witness dramatic views of the rolling hills that surround the property. A tranquil pond with gazebo graces the landscape. A well-appointed barn with 5 stalls and a paddock caters to equestrian enthusiasts. Miles of trails crisscross the property, providing endless opportunities for outdoor activities. This property is in Vermont Current Use Program, securing its natural beauty for the future. Whether you are relaxing on the porch or hosting gatherings in the spacious bonus room, this estate balances seclusion and convenience. Situated in bucolic Jamaica, it is 20 minutes from Stratton and 25 minutes from Mount Snow. Let this be your four season retreat, close to the mountains in the winter, swimming holes in the summer, and stunning views all year round!

Listed by Andie Fusco and Tara van de Velde of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* 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

3496 Main Street Manchester VT 05254

Manchester, VT3496 Main Street

Price$2,327,000

Est. Mortgage: $/month

Pending

MLS Number 5025729

  • Residential Single Family
  • Full Bath 4
  • Address 3496 Main Street
  • Construction Existing
  • Bedrooms 6

Situated in the heart of the historic village of Manchester, Vermont, this 6-bedroom, 5-bathroom Victorian offers timeless charm paired with modern luxury. Completely renovated in 2021, the home seamlessly blends historic character with contemporary design. Perfectly situated, it abuts both the prestigious Ekwanok Golf Club and Equinox Golf Course, offering proximity to world-class golfing while maintaining a tranquil and private atmosphere and just steps away from Equinox Hotel and Spa. The home's architectural beauty is evident from the moment you arrive, with a sweeping wraparound porch that provides breathtaking mountain views. A full wall of doors opens to the porch, creating a seamless connection between indoor and outdoor spaces-perfect for entertaining or quiet relaxation. Inside, the home has been meticulously updated to include a chef's kitchen with state-of-the-art appliances, a spacious dining area, and a cozy living room featuring exposed beams and a wood-burning fireplace. Thoughtful details abound, including local Vermont marble used for the sidewalk and foundation stones, paying homage to the region's rich heritage. The primary suite offers mountain views, a spa-like ensuite bath, and abundant natural light, while four additional bedrooms provide ample space for family and guests. The lower level includes a fully appointed 1-bedroom apartment, ideal for extended family, and guests. Upgrades include radiant floor heating system and central air.

Listed by Betsy Wadsworth of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* 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

330 Rupert Hill Road Pawlet VT 05761

Pawlet, VT330 Rupert Hill Road

Price$2,300,000

Est. Mortgage: $/month

MLS Number 5018436

  • Residential Single Family
  • Full Bath 1
  • Address 330 Rupert Hill Road
  • Construction Existing
  • Bedrooms 5

Amazing Agricultural Package: 54 Bucolic Acres, 360 degree hill-top views, 1407 feet Mettowee River frontage, Complete 2023 Renovation of 5343 SF contemporary farm house, Barns and Run-in sheds, Guest house, Walk to Pawlet Village convenience! That's just the tip of the iceberg... the winding drive overlooks open pastures and rolling terrain through hardwood forests as it approaches the hill top farm that is surrounded by the most impressive view perspectives. A sophisticated gentle farm perched over the Mettowee Valley offers a wonderful open concept with all resurfaced 4+BR homestead that boasts amazing views from every window! Yes, this house was designed to take full advantage of the location! The handsome wide plank floors flow seamlessly from one kitchen/dining/family/sun Greatroom with brick fireplace to the Cathedral Post and Beam Greatroom with raised hearth stone fireplace. Comfort expressed in a lovely main level primary suite with balcony and luxury bath, soaking tub and shower, while there's a second main level suite. Upstairs two more en-suite bedrooms and nanny room. Lower level rec rm, bunk rm, bath. There are so many quality components to mention: barns, studio space, vehicle space, animal shelters, stalls, chicken coop, fishing studio, and run-in sheds. Outbuildings are in great condition with power. The Log house makes memories for guests, rents or services help. When one looks outward from the kitchen sink and can see 3 silo's, it doesnt get better!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* 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

18 Timber Creek Road Ludlow VT 05149

Ludlow, VT18 Timber Creek Road

Price$2,300,000

Est. Mortgage: $/month

MLS Number 5026376

  • Residential Single Family
  • Full Bath 3
  • Address 18 Timber Creek Road
  • Construction Existing
  • Bedrooms 4

Timber Creek on Okemo - A Mountain Retreat Like No Other. Discover the perfect blend of privacy and convenience with this stunning Timber Creek home, nestled on 3.31 serene acres at SouthFace Village on Okemo Mountain. Just steps from the Sunshine Quad, you'll enjoy unparalleled mountain access alongside exclusive amenities. This 4-bedroom, 5-bathroom, 3-level timber frame home offers an inviting open floor plan, ideal for hosting family and friends. Soaring cathedral ceilings showcase the craftsmanship of the timber frame design, while the crackling wood-burning fireplace serves as the centerpiece of the cozy living area making this the perfect mountain retreat. The chef's kitchen, featuring a large island, encourages lively gatherings, conveniently open to the dining room perfect for shared meals and many memories. The main level boasts an en suite bedroom, while upstairs you'll find three additional bedrooms, two with private baths making for great guest quarters. The lower level is designed for fun, with a spacious family room perfect for movie or game nights. With a two-car garage, mudroom for all your gear, and access to SouthFace Village amenities-including easy access to the Sunshine Quad located within Southface Village offering you great mountain access, a recently constructed clubhouse, heated outdoor pool and spa, fitness center, locker, and private parking-you'll have everything you need for a luxurious mountain lifestyle!

Listed by Katherine Burns of William Raveis Vermont Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* 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

20 West Ridge Road Stratton VT 05155

Stratton, VT20 West Ridge Road

Price$2,250,000

Est. Mortgage: $/month

MLS Number 5002928

  • Residential Single Family
  • Full Bath 4
  • Address 20 West Ridge Road
  • Construction Existing
  • Bedrooms 5

OPEN HOUSE. Friday July 5th, 2-4pm. All Welcome. The exquisite craftsmanship of this stunning Austrian-style chalet evokes the lure of Stratton's early days. A location that was selected for incredible views, and close ski trail access. This true mountain haus has been thoughtfully updated to preserve its charm and authenticity. Imagine waking up to incredible mountain views every morning and enjoying cozy evenings by the fire in your timeless alpine escape. Air conditioned, updated kitchen, updated windows, and a three car garage. Three en suite bedrooms on the second floor, and two additional bedrooms and a full bathroom in another part of the house. The great room is complete with a bar, amazing acoustics, and a breathtaking view. The library has its own fireplace, and secret wine room accessed by a discreet buzzer. The Appalachian/Long Trail crosses nearby for year round hiking and backcountry adventures. This is the place you'll never want to leave.

Listed by Christiane Carroccio of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* 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

380 Ghia Farm Road Ludlow VT 05149

Ludlow, VT380 Ghia Farm Road

Price$2,200,000

Est. Mortgage: $/month

MLS Number 5001760

  • Residential Single Family
  • Full Bath 1
  • Village Ludlow
  • Address 380 Ghia Farm Road
  • Construction Existing

Welcome to Phelps Barn on Sachem. This home is a replica of the famous Phelps Barn, part of the historic Grafton Inn and currently used as the Inn's pub. There are large gathering spaces, perfect for entertaining, with two wood-burning fireplaces and a fun loft area. The kitchen has been redesigned and flows nicely into the dining room. The ski room entry has all the space you need to store your gear or prepare for the next run. The location is highly sought after and right on the green Sachem ski trail for true ski on - ski off. You can watch the skiers swoosh by from the large windows in the great room, seats on the deck, or from the trailside hot tub. The lower level is great for games, movies, or relaxing. You will find the primary bedroom on the main level and three more bedrooms on the upper levels. The front porch is welcoming and the side deck leads you to the back lawn with stone wall features. There's plenty of parking because all your friends and family will want to visit. Visit the Okemo Valley real estate community today. Taxes are based on current town assessment. ROFR.

Listed by Kevin Barnes of William Raveis Vermont Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* 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

1328 Chandler Road Chester VT 05143

Chester, VT1328 Chandler Road

Price$1,995,000

Est. Mortgage: $/month

Active With Contract

MLS Number 5002063

  • Residential Single Family
  • Full Bath 2
  • Address 1328 Chandler Road
  • Construction Existing
  • Bedrooms 4

Design inspired by Frank Lloyd Wright this mid-century modern home is a beacon of tranquility for those looking for privacy. Surrounded by 193 acres including 13 acres of open pasture traced with ancient stone walls. Enjoy more than 2 miles of trails crossing brooks and fields. This magnificent haven for lots of wildlife has apple trees, raspberry bushes and more than 50 blueberry bushes. Inside a wide-open main living area and great room overlooks the 10 foot deep swimming pond, and the nearby stream can be heard from the deck or kitchen with the windows open. Step into the luxurious primary suite, a sanctuary with large windows and a spa inspired bath with a free-standing tub that boasts one of the best views from the house. Enjoy the newly renovated lower level with additional bedrooms and expansive family room. This area is ready for your touch and enjoys walkout access to the yard and pond. The 2nd level of the barn is currently a wood shop with wood-stove and a 2nd access from the road allows for storing large pieces or equipment on this upper level. The ground level of the barn has traditional sliding barn doors and extensive parking in front. Underground power and water lines travel from the house to a nearby site where another barn or horse arena could be built. A unique home treasure and like its organic architectural design the land has its own special quality of character and beauty. 191 acres are in the VT Land Use program. There is a 6 bedroom septic.

Listed by Suzanne Garvey and Elissa Scully of Mary W. Davis Realtor & Assoc.,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.89% last updated on Feb 6, 2025
* 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 2025 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 February 11, 2025 3:52 AM EST