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Bennington County Real Estate

Bennington County is located in Southwestern Vermont and encompasses the towns of Arlington, Bennington, Dorset, Glastenbury, Landgrove, Manchester, Peru, Pownal, Readsboro, Rupert, Sandgate, Searsburg, Shaftsbury, Stamford, Sunderland, Winhall, and Woodford. Bennington County is the oldest county in Vermont still in existence, and you will find evidence of this rich history throughout the region at historic sites such as the Bennington Battle Monument in Bennington. You will also find fantastic shopping options from local artisans to big name brands as well as plenty of entertainment and dining options throughout the region. Bennington County covers over 670 square miles and is home to part of the Green Mountain National Forest as well as part of the White Rocks National Forest. You will find a handful of post-secondary schools in Bennington County including Bennington College and Southern Vermont College.

Explore current real estate for sale in Bennington County, Vermont. If you have any questions or if you'd like to see any of these properties in person, call 802-793-2002 or contact us online.

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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
  • County Bennington
  • Property Type Single Family
  • Bedrooms 5
  • Bathroom 6

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: 6.65% last updated on Mar 13, 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.

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527 Benson Road Manchester VT 05255

Manchester, VT527 Benson Road

Price$4,975,000

Est. Mortgage: $/month

MLS Number 5011880

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 5
  • Bathroom 4

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: 6.65% last updated on Mar 13, 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.

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507 Benson Road Manchester VT 05255

MLS Number 5011616

  • Commercial
  • County Bennington
  • Square Feet 5,445
  • Acreage 53

Rustic simplicity. Luxury retreat. Complete privacy and surrounded by National Forest. Green Mountain Resort at Boorn Brook Farm in Manchester Center is shovel ready. All town zoning and Vermont State Act 250 permits are in place, along with all other required environmental and state approvals, for developing a 46-cabin, four-season retreat on 53+acres. With big views of Mt. Equinox and the Taconic Range and sited at the end of Benson Road, Green Mountain Resort at Boorn Brook Farm is within the Rural Agricultural zoning district, with a portion in the Forest Conservation zoning district. Just 2 miles from the center of Manchester, the property is bordered to the north by Bourn Brook and surrounded on the east, south, and west by the Green Mountain National Forest and Lye Brook Wilderness. Included in the sale are a C.1790 farmhouse and C.1820 barn, which have been extensively renovated, trout pond, meadows, woodlands threaded with trails and tennis/pickle ball court. Refer to the residential listing for more information. A significant amount of the required infrastructure and project components are already in place. Envisioned as an eco-friendly, experiential retreat, the project aims to provide guests with an opportunity to connect with nature and the community through immersive and educational experiences. Green Mountain Resort at Boorn Brook Farm is also perfect for hosting weddings, corporate retreats, cultural events, and business conferences.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 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.

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0 Terry's Loop Manchester VT 05255

MLS Number 5018667

  • Commercial
  • County Bennington
  • Acreage 3.81

Discover a prime commercial opportunity at the heart of southern Vermont! Located off Airport Road in Manchester, this well-established industrial park offers a versatile space for businesses, developers, or investors looking for a strategic location. Comprising 38,000 sq feet over 7 buildings, this site is a well-maintained industrial park that blends convenience and functionality. Currently 100% leased, the property features several large industrial buildings, flexible spaces for warehousing, manufacturing, or distribution, and ample parking. Its location offers excellent access to major routes, including Route 7, making it an ideal hub for logistics, light manufacturing, or a growing business looking to expand operations.

Listed by Paul W. Carrocio and Marek Kovac of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 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.

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73 Pine Road Dorset VT 05251

Dorset, VT73 Pine Road

Price$3,275,000

Est. Mortgage: $/month

MLS Number 4994366

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 6
  • Bathroom 4

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 Chrissy Carroccio of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 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.

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25 Mountain Haunts Road Winhall VT 05340

Winhall, VT25 Mountain Haunts Road

Price$2,999,000

Est. Mortgage: $/month

MLS Number 5029450

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 6
  • Bathroom 7

Attend the PUBLIC OPEN HOUSE Monday February 17 from 10:00-2:00. Exceptional 40.8 acre newly expanded and renovated Stratton Mountain estate with unrivaled views of Stratton just minutes from the Base Lodge or Sun Bowl. This is your own personal winter playground where you can hit the slopes or snowmobile and hike on your own land with additional acreage available.This Grand Lodge NOW BOASTS 4 ensuite bedroom, 3 stone fireplaces, huge lodge room w/ large beams and walls of glass and VIEWS VIEWS, VIEWS which is nothing short of EXTRAORDINARY. New gourmet kitchen and baths.PLUS a 2 bedroom/2bath guest house.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.This will also be your summer retreat with 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, theManchester Music Festival, The Dorset Summer Equestrian Festival. Hiking, biking, kayaking, shopping and dining. Fall foliage, first tracks on powder days and the Green Mountain Summers beckon.This one of a kind property is the essence of a true Escape

Listed by Kim Morgan-Wohler of Wohler Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 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.

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19 Old Town Road Winhall VT 05340

Winhall, VT19 Old Town Road

Price$2,780,000

Est. Mortgage: $/month

MLS Number 5031720

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 5
  • Bathroom 7

Experience Vermont luxury at 19 Old Town Road, Winhall-a stunning 5-bedroom, 7-bathroom estate on 21.53 private acres. Built in 2000, this meticulously designed retreat offers unobstructed views of both Stratton Mountain and Magic Mountain. The spacious great room is the heart of the home, featuring soaring ceilings, a grand stone fireplace, and walls of windows that frame breathtaking mountain vistas. A gourmet kitchen with high-end appliances, custom cabinetry, and ample workspace is perfect for entertaining. The den is a home office with a beautiful fireplace and built in bookcases. With five bedrooms each with their own bathroom, two half baths, thoughtfully designed living spaces, and high-end finishes throughout, this home seamlessly blends elegance and comfort. Enjoy privacy and seclusion while being just minutes from Stratton Resort, Magic Mountain, Bromley, and Manchester. This extraordinary property is a rare opportunity to own a piece of Vermont's finest landscape.

Listed by Chrissy Carroccio of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 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.

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113 Depot Street Bennington VT 05201

Bennington, VT113 Depot Street

Price$2,500,000

Est. Mortgage: $/month

MLS Number 4964839

  • Land
  • County Bennington
  • Square Feet 38,333
  • Acreage 0.88

Mixed use development site in the heart of Downtown Bennington. .88 acre site with Zoning, Preservation and Stormwater approvals for a 60,000 sq ft mixed use building with planned commercial occupancy on the first floor and three stories of residential occupancy above - 60 units total with 12 units of workforce housing.

Listed by Paul W. Carrocio and Marek Kovac of TPW Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 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.

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113 Depot Street Bennington VT 05201

MLS Number 4964861

  • Commercial
  • County Bennington
  • Acreage 0.88

Mixed use development site on the heart of Downtown Bennington. .88 acre site with Zoning, Preservation and Stormwater approvals for a 60,000 sq ft mixed use building with planned commercial occupancy on the first floor and three stories of residential occupancy above - 60 units total with 12 units of workforce housing.

Listed by Paul W. Carrocio and Marek Kovac of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 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.

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00 Vt Route 11 Peru VT 05152

Peru, VT00 Vt Route 11

Price$2,500,000

Est. Mortgage: $/month

MLS Number 5005964

  • Land
  • County Bennington
  • Square Feet 9,888,120
  • Acreage 227

Seize a once-in-a-lifetime opportunity with this stunning 227 +/- acre legacy property, nestled against the natural backdrop of the National Forest and Bromley Mountain. This expansive parcel offers development potential, making it the perfect canvas for creating a private compound or a luxury mountain retreat. Imagine waking up to breathtaking sunrise views of Stratton and the Green Mountain National Forest, with outdoor adventures right at your doorstep. The property's generous size provides ample space for multiple dwellings and private amenities, ensuring privacy and exclusivity. Whether you envision a serene family estate or a secluded sanctuary, this property is the ideal setting to bring your vision to life. Embrace the tranquility and splendor of mountain living; one could even ski back to the property from Bromley. Enjoy all that Southern Vermont has for you, while being just a short distance from, Magic, Stratton and Manchester. Don't miss out on this rare chance to own a piece of paradise that can be cherished for generations to come.

Listed by Kevin Moran of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 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.

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1251 West Road Manchester VT 05255

Manchester, VT1251 West Road

Price$2,500,000

Est. Mortgage: $/month

Pending

MLS Number 4976603

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 9
  • Bathroom 7

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: 6.65% last updated on Mar 13, 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.

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743 Green Peak Orchard Road Manchester VT 05255

MLS Number 4970555

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 5
  • Bathroom 5

Beautifully designed to capture spectacular views of mountains and sunsets, this exceptional residence has recently completed the addition of another full bath, improving the floor plan, situated on 7.9 open acres w/guest house/barn off Overlook Drive in Green Peak Orchard. With views from every gathering space; living room, billiard room and gourmet kitchen, the residence is situated to maximize the setting and access to the outdoors.Wonderful spaces for entertaining. Kitchen features oversized island, 2 dishwashers - Bosch and Wolf appliances. Formal dining opens to living area w/ wide pine floors, fireplace, walls of windows Exceptional outdoor spaces with large patio, gardens and meadow. The second floor, offers 4 bedrooms/3 full baths. 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: 6.65% last updated on Mar 13, 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.

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18 Rocky Dell Road Winhall VT 05340

Winhall, VT18 Rocky Dell Road

Price$2,450,000

Est. Mortgage: $/month

Active With Contract

MLS Number 5011900

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 7
  • Bathroom 6

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: 6.65% last updated on Mar 13, 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.

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2589 West Sandgate Road Sandgate VT 05250

Sandgate, VT2589 West Sandgate Road

Price$2,345,000

Est. Mortgage: $/month

MLS Number 4999597

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 5
  • Bathroom 6

Exceptional Country estate spanning 30 acres nestled in the heart of the Green Mountains. Magnificent panoramic mountain views, rolling meadows, mature gardens, and babbling brook encompass the Vermont lifestyle. Solar power and heated green house create a self-sustaining oasis. The main house features a wrap-around porch for breathtaking views. The stone patio offers a custom brick oven and dining space surrounded by beautiful gardens. Inside, natural light filters through expansive windows, illuminating rich hardwood floors. The kitchen exemplifies the perfect blend of classic and modern, featuring an AGA range, timeless soapstone countertops, Viking appliances, and a generous pantry. Your choice of several spacious outdoor dining areas or formal dining room. Relax in one of two living rooms, featuring wood burning stone fireplaces. The primary suite is a sanctuary with a marble ensuite bathroom and private fireplace. Four additional bedrooms provide ample accommodation for family and guests. The estate includes several outbuildings featuring a full kitchen, studio and art lounge. Below, a multi-car garage, commercial kitchen, and workshop offer space for hobbies and toys. A second building offers a 9-stall horse barn and a 6-port awning for outdoor equipment. Spend the day at your stone patio and custom infinity pool or fish in your own pond. Schedule today and make your dream of natural luxury living a reality.

Listed by Margretta Fischer of Wohler Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 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.

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3496 Main Street Manchester VT 05254

Manchester, VT3496 Main Street

Price$2,327,000

Est. Mortgage: $/month

Pending

MLS Number 5025729

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 6
  • Bathroom 5

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: 6.65% last updated on Mar 13, 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.

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1086 West Road Bennington VT 05201

Bennington, VT1086 West Road

Price$2,225,000

Est. Mortgage: $/month

MLS Number 5000598

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 9
  • Bathroom 7

Captivating French Provincial architecture is the hallmark of this 6,800 sq. ft 1866 Manor House occupying a commanding and picturesque view over 94 acres of pristine pastoral fields and the distant Taconic Mountain Range. The timeless and beautifully proportioned interiors feature extensive molding, solid oak flooring, eight fireplaces, nine bedrooms, seven baths, country kitchen and adjoining pantry, formal dining and living rooms. The private estate includes a three car garage, four bedroom caretakers cottage, artist studio and gunite heated in-ground pool. Set on the outskirts of the historic town of Bennington offering shopping, live theatre, restaurants, horseback riding and proximity to mountain and cross-country skiing. This is a rare opportunity to own an exquisite estate property with a myriad of possibilities as a family compound or country retreat. Only 45 minutes to Albany International Airport and approximately three hours to Manhattan and Boston. All measurements approximate.

Listed by Chris DeFelice and Elena Atwill of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 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.

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1228 Skiparee Road Pownal VT 05260

Pownal, VT1228 Skiparee Road

Price$2,100,000

Est. Mortgage: $/month

MLS Number 5008279

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 4
  • Bathroom 3

Welcome to Amara Farm, an equestrian paradise in Southern Vermont. This meticulously planned property offers a 13-stall barn designed with every detail in mind, ensuring comfort and efficiency for both horse and rider. The state-of-the-art indoor arena features GGT footing and a full wall of window providing top-quality conditions for training and performance. Turnout paddocks and outdoor arena greet you with remarkable mountain views, creating a picturesque backdrop for your riding sessions.Explore the extensive trails on the 30 acres equipped with cross-country jumps and hills, perfect for leisurely rides or serious training. The four bedroom home is a luxurious respite from barn time. The open layout kitchen to living and dining also offers doors to a deck with a view of the mountains and gardens, and a screened porch. Wolf cooktop, walk in pantry, wet bar, and an oversized island make up a stellar kitchen. The office has views of paddocks with run-in sheds. The master suite has dual walk in closets, spa bathroom, and balcony. Lowest level of the home is a theater room, gym, and walks out to a covered patio and firepit. After a day of riding, cool off in the 'tubs' swimming hole. Barn has 2 bedroom apartment. Located just 15 mins from Bennington, VT, and 15 mins from Williamstown, MA, Amara Farm offers the perfect balance of rural tranquility and convenient access to nearby towns and equestrian competition venues. Don't miss this rare opportunity. Inquire for more details.

Listed by Chrissy Carroccio of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 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.

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132 Landgrove Road Landgrove VT 05148

MLS Number 5007077

  • Commercial
  • County Bennington
  • Square Feet 9,730
  • Acreage 23.7

The Landgrove Inn and InView Center for the Arts is an historic, quintessential, full service country Inn set in the picturesque town of Landgrove, surrounded by the majestic Green Mountains. With over 23 acres which include the Inn, Restaurant and Tavern, Arts Center buidling, beautiful pond, and inground pool, there are numerous opportunities. Within minutes of Okemo, Bromely, Stratton and Magic ski areas as well as local cross country skiing. Summer draws guests for the beautifully lanscaped property with pool, pond, pickleball court and proximity to the Weston Theater Company and numerous lakes. The InView Center for the Arts draws over 35 groups per year with up to 15 rooms, for 5 nights with 3 meals daily, providing tremendous base business. The Arts Center building is key to this revenue stream and with over 1800 sq ft, it has potential for numerous other uses. The Inn offers 16 rooms and suites and owners quarters consisting of 3 rooms. The property has been well cared for by the current owner for over 21 years and they have increased revenues streams while reinvesting in the business including the addition of the Arts center building in 2009, new generator in 2023 and replacing the roof on half the Inn in 2022. A country gem with a solid group base revenue stream and so much potential for additional revenue growth.

Listed by Brian Gehlich and David Citron of RE/MAX Four Seasons

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$
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$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 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.

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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
  • County Bennington
  • Property Type Single Family
  • Bedrooms 4
  • Bathroom 4

This mountain home is beautifully furnished with a refined design that perfectly balances comfort and style, offering a seamless move-in ready experience. 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, including new furniture. 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, a second living room, and cozy space for 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 with all new furniture. Watch the Stratton fire works display from your living room this season!

Listed by Chrissy Carroccio of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 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.

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301-321-341 Depot Street Manchester VT 05255
Active With Contract

MLS Number 4996358

  • Commercial
  • County Bennington
  • Square Feet 17,676
  • Acreage 1.79

There are THREE BUILDINGS INCLUDED IN THIS OFFERING. Building #1, 301 Depot Street has 5,652 sq ft on two floors, includes and elevator. Building #2, 321 Depot Street has 6,108 sq ft on 2 floors and NO Elevator. Build #3, 341 Depot Street has 5,916 sq ft, on two floors with elevator and currently has a mo. to mo. tenant who occupies the entire building. The Town of Manchester who owns the land acquired the buildings as the result of the experimentation of a Land Lease the Town had with the Tenant who constructed all 3 buildings. Currently buildings 301 and 321 are vacant. Building 341 has a tenant who occupies the entire building and is currently on a month to month basis. This Tenant has expressed a desire to remain in this location and is seeking a long term lease. Based on this information, the Town of Manchester makes not representations as to the Current Tenant or conditions of the buildings, they are being sold "AS IS". Sales price is below the most recent appraisal of the property. There are 82 parking spaces according to the appraisal. All the above information was provided to the broker via the Town of Manchester based on the appraisal which also notes that the property appears to be in the flood hazard zone. The Town Center Zone allows for the most intensive commercial and mixed-use development in Manchester. Vehicle Count 7,379, 2020. Prospective Buyers will be required to sign a confidentiality agreement and show proof of funds.

Listed by Dick Palmer of Hospitality Consultants,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 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.

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3904 & 3888 Vt Route 7a Arlington VT 05250

MLS Number 5000805

  • Commercial
  • County Bennington
  • Square Feet 14,324
  • Acreage 3.76

Welcome to The Arlington Inn & Spa, nestled in the historic village of Arlington. This exceptional property is enveloped by the picturesque Green Mountains and located minutes from the legendary Battenkill River. The charming retreat spans 3.76 manicured low-maintenance acres. The well established gardens, courtyard and gazebo offer so many entertaining options. The 100-capacity event barn with new foundation is ready for weddings, or health retreats. The current owner has just installed all new underground fiber optic and power lines throughout the property. The Main Inn, features a commercial kitchen, two dining rooms, spa, tavern and five guest suites. The Carriage House offers six stately guest suites and an additional six suites in the beautifully renovated Parsonage. The property has been thoughtfully updated with new baths, furnishings, decor and utilities throughout. The recently renovated Tavern and spa adds new life and opportunity to the business. Perfect for a chef-owned property with the commercial kitchen or family retreat to create priceless memories. The possibilities are endless. An investor looking to add a historic and luxurious property to their portfolio can easily see the potential. Don't miss this opportunity! Short 3 hours from NYC, 45 min. to Saratoga and 15 minutes to Manchester's shopping. Call today for a personal tour and see the endless opportunities to be had!

Listed by Margretta Fischer of Wohler Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 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.

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3904 & 3888 Vt Route 7a Arlington VT 05250

Arlington, VT3904 & 3888 Vt Route 7a

Price$1,875,000

Est. Mortgage: $/month

MLS Number 5003040

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 17
  • Bathroom 20

Historic Family Estate. A unique and versatile opportunity is ready for you to call home! This classic landmark boasts three residences, large barn, gazebo and fenced-in garden. Perfect for a four-season family retreat or a full-time residence. The grand main building circa 1848 formerly the private estate of Martin Chester Deming famous railroad magnate, politican and businessman from the industrial era of wealth and accomplishment. Representative Deming would invite the NYC, Boston and local socialites to elaborate parties. The charm of the era is still alive in the home today. His personal tavern, the Deming Tavern has just been renovated. Real Vermont marble throughout the estate marks the quality of yesteryear. The marble steps up to the parsonage offer the perfect guesthouse for all your friends and family. And the carriage house could be a wonderful studio or office space with additional rooms. Original exposed beams, wood & gas fireplaces, grand staircase together with 30 rooms, 17 bedrooms, 19 baths on 3.76 aces. The famous Battenkill River is just down the street renown for world-famous fly fishing. Next to the river, you will discover a delightful 9-hole golf course, river trails, tennis courts, and ice skating rink. All these incredible opportunities are right here waiting for you in the historic village of Arlington. Don't miss this opportunity to own a slice of Vermont. Upgrades include 4 updated bathrooms, 5 new baths, fiber optics and new landscaping.

Listed by Margretta Fischer of Wohler Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 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.

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3309 3321 Main Street Manchester VT 05254

Manchester, VT3309 3321 Main Street

Price$1,850,000

Est. Mortgage: $/month

MLS Number 4977864

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 11
  • Bathroom 9

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: 6.65% last updated on Mar 13, 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.

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43 Pearl Buck Drive Winhall VT 05340

Winhall, VT43 Pearl Buck Drive

Price$1,850,000

Est. Mortgage: $/month

Active With Contract

MLS Number 5021694

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 5
  • Bathroom 5

Listed by Kim Morgan-Wohler of Wohler Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 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.

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36 Beaver Street Winhall VT 05340

Winhall, VT36 Beaver Street

Price$1,825,000

Est. Mortgage: $/month

MLS Number 5014019

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 4

Come and take a look at this beautifully designed custom log home and an entertainment/quest house, located less than 10 minutes from Bromley Mountain and the Stratton Mountain Access Road. This exceptional log home feels like a mountain lodge. The oversized living room with exposed timbers and cathedral ceiling features a large TV, pool table, shuffleboard, arcade games, wet bar & majestic stone fireplace! Open recently renovated kitchen with stainless-steel appliances connected with a dining area and a sunroom. You'll appreciate the thoughtful planning and attractive detailing applied in every room. This expansive residence also includes a 2250 sq feet Entertainment/quest house built in 2022 with a large living room, open contemporary kitchen, bathroom/laundry and a sizeable, covered porch for summer outside living and a full Entertainment/arcade room on the first floor with a bar. Private wooded property with new outdoor kitchen, fire pit, hot tub, lots of decking with built in seating, playground, horseshoes and basketball court. In Spring, Summer and Fall enjoy the delightful sounds of the pond fountain. All measurements are approximate. Sold furnished. Arcade machines are negotiable.

Listed by Tatsiana Clark of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 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.

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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 March 19, 2025 11:09 AM EDT