and narrow your search. If you have fewer than 200 results, you can save your search.

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 802-760-3100 or contact us online.

Create a free account to save your favorite Vermont real estate listings and get notified when similar properties become available.

You can also view all the towns in this county.

90 Snow Valley Road Winhall VT 05340

Winhall, VT90 Snow Valley Road

Price$4,950,000

Est. Mortgage: $/month

MLS Number 4826030

  • Land
  • County Bennington
  • Property Type Land
  • Acreage 447

On the slope-side of the storied Snow Valley Ski Resort, presents a truly unique development opportunity for a new vision to encompass a family-oriented, four-season community resort. Drawing from the major metropolises of New York City and Boston, this 450+ acre site is poised to draw a number of hospitality, residential and recreational uses to capture increasing demand by urban residents seeking immersion in nature and the great outdoors. A buyer or equity partner will be presented with the ability to create an authentic, architecturally significant, multifaceted venue giving nod to the great historical Adirondack camps, mountain communities and traditional Vermont homesteads. As an eco-minded boutique hotel/glamping resort, sporting club, residential community, or iconic estate property, future patrons and residents will have endless activities to enjoy in this ultimate safe haven.

Listed by TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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

135 Paddock Farm Lane Dorset VT 05251

Dorset, VT135 Paddock Farm Lane

Price$4,850,000

Est. Mortgage: $/month

MLS Number 4874056

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 6
  • Bathroom 10

This exquisite Dorset estate brings sophisticated European charm to the pristine mountains of Vermont. Nested in the exclusive Dorset Hollow, when the gates of Four Pounds part one is transported beyond New England. Reminiscent of a French château, the use of natural materials grounds this expansive stone and timber residence adorned with cedar and copper. Herringbone brickwork, magnificent Tudor chimneys, old-world shutters, and intricate terraces and stone walls add to the grandeur of this build. With multiple spring-fed ponds and glorious gardens, this lush corner of Vermont is a haven for birds and wildlife. The reclaimed 16th-century French front doors lead to the heart of this thoughtfully designed 11,500 SF home. The layout offers grand spaces for hosting, quiet corners for moments of respite, 6 ensuite bedrooms, a gym, an elevator and more. The finishes are welcoming and invigorating - rich woodworking, terra cotta tile, exposed beams, dramatic archways. With spectacular views from every window, you and your guests will revel in this refined sanctuary. Minutes to Dorset and Manchester with their beautiful shops, restaurants, and marble sidewalks, you can indulge in the best of Vermont life while enjoying complete privacy on 18.7 acres (6.7 acre being separately deeded - perfect for a guest house). Revel in the arts at the Dorset Playhouse, Manchester Music Festival and Art Center. Helicopter service to NYC and airports nearby. Make this your East Coast address.

Listed by Cheyanne Pugliese and Kim Morgan-Wohler of Wohler Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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

1048 Black Hole Hollow Road Arlington VT 05250

MLS Number 4868628

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 7
  • Bathroom 8

Ian Fleming, Famed creator of James Bond, once mused in the guest register of Black Hole Hollow Farm, "Lived here like a king - an uninvited one - in fragrant and luxurious solitude" a bucolic and timeless sanctuary. This remarkable estate located on 228 verdant acres bordering both state and national forest, offers an unparalleled backdrop to an especially private hideaway. Extensive walking and riding trails are interwoven throughout. The beautiful stone mansion overlooks lush hilled lawns, two tiered ponds and waterfalls. Original house dates from 1772, expanded and designed by the renowned architect Jerome Cerny in the 1930's. The grand living room and downstairs bedrooms open onto the gardens through French doors and master suite provides private access to a poetic walled garden. There are fireplaces throughout, attached guest house, heated greenhouse, barn, cutting and vegetable garden. The estate has entertained a cast of characters including Sir Ian Fleming, spending summers finding inspiration and writing the classics "Diamonds Are Forever," "Goldfinger" and "For Your Eyes Only." Owners were Josephine Hartford Bryce, heiress of A&P, and husband Ivar rumored to be the inspiration for Bond. Easy drive to Albany Int'l Airport, Manchester and Saratoga's thoroughbred racing. Cultural activities of theatre, art, museums and dance nearby. To hike, ride, hunt, farm, fish or drive off-road in the surrounding forest. To find inspiration in a deeply rooted sense of home.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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

275 High Fields Lane Manchester VT 05254

Manchester, VT275 High Fields Lane

Price$3,900,000

Est. Mortgage: $/month

MLS Number 4813653

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 9
  • Bathroom 12

Luxury and sophistication in the Green Mountains! Located at the base of the Equinox Mountain this property offers 13 private acres of elegant oasis with exquisite landscaping, mountain views, English garden, green house, apple orchard and access to miles of hiking trails. Architecturally traditional with contemporary features the house offers state of the art mechanicals including security system, whole house on demand generator, central air, radiant heat, 5 fireplaces, gourmet kitchen with butlers pantry to formal dining. With 9 ensuite bedrooms, home theater, recreation room, home gym, library and multiple family rooms you can entertain extended family or extra guests. Take in the sun rise on the 93 foot long covered porch overlooking the Green Mountains. Just minutes from shopping, dining, entertainment and skiing, there's no reason to ever be bored again. Truly a must see!

Listed by Adrienne Sherwood of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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

1166 West Road Manchester VT 05254

Manchester, VT1166 West Road

Price$3,395,000

Est. Mortgage: $/month

MLS Number 4863655

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

Picture Perfect Manchester Country Estate provides exceptional privacy on 16 treelined acres! This property checks the boxes: amazing views, stream, swimming pond, trout pond, beautiful barn, garden shed, green house, 6 garage bay's, expansive agricultural / perennial gardens, stone walls, orchard, outdoor gathering rooms and 2 substantial 2019-20 renovated & extended residences. Circa. 1800 post & beam colonial moved to the site given the tight concrete foundation benefit under the entire house, this is the perfect meld of "old world" architectural detail and contemporary living. Gracious comfort begins with the new kitchen-island/great room boasting finishes that suggests "this has always been" as three walls of light ensures all shall gather around the fireplace or the cooks raised hearth grilling fireplace. The appliances meet perfection while pantries and tuck away bar serve well! Dining and Living rooms offer nature's light and centered fireplaces, while the fifth fireplace in the cherry panel study provides quiet refuge. The music room would also provide a second office. The crown moldings & lovely flooring flows throughout. Upstairs, the primary suite offers three window walls, walk-in closets, and sizable bath, three other bedrooms each with private baths! Lower level rec room and wine cellar. The guest house shall amaze, accommodating a main level suite, 2 BR's up, 3 BA, comfort living: sun room, great room/FP, and walk-out rec room. Commanding Mount Equinox Views!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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

440 Marcia Lane Dorset VT 05251

Dorset, VT440 Marcia Lane

Price$3,395,000

Est. Mortgage: $/month

MLS Number 4700856

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 5
  • Bathroom 8

This extraordinary country estate will captivate you with exceptional mountain vistas, sophisticated finishes and abundance of outdoor spaces. Perched upon a knoll in Dorset's exclusive Upper Hollow, this exquisite 8700 SF residence is sited on 17.25 acres w/ post and beam barn/pool house, indoor basketball court and outdoor heated pool. Beautiful gardens, mature landscaping and meticulously created stone patios, terraces and walkways create a most inviting setting.You'll enjoy the lush amenities of this Dorset gem!With craftsmanship of the highest caliber, this classic vernacular residence features wide pine floors, crown molding, wainscoating,slate, marble and soapstone throughout. The living areas boast post and beam finishes and open to the covered wrap around porch and stone patio with outdoor kitchen.The grand main floor master en-suite is privately situated and showcases a dramatic Benson post and beam design.This private retreat is designed for entertaining &maximizes the sweeping views.The gourmet kitchen opens to the living area and a formal dining room.A billiard room &comfortable den offer multiple gathering spaces for entertaining or simply relaxing.Five bedrooms en-suite, game room, 3 fireplaces. Just 5 minutes to the Dorset Green with the Dorset Inn, Barrows House, Dorset Playhouse & the 3 Pear Gallery. With Bromley and Stratton Mountains just a short drive away, you'll enjoy Dorset and the mountains from this expansive and alluring property.

Listed by Kim Morgan-Wohler of Wohler Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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

779 Wind Hill Road Dorset VT 05251

Dorset, VT779 Wind Hill Road

Price$3,275,000

Est. Mortgage: $/month

MLS Number 4857539

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

Situated at the foot of Green Peak in Dorset, sits one of Southern Vermont's most exceptional properties that combines the design elements of a sleek Manhattan contemporary with a quintessential Vermont estate. This 3-bedroom, 3 & ½ bathroom residence is custom crafted with an impeccable selection of materials. A luminous great room with 25-foot high ceilings, floor to ceiling windows highlight the expansive mountain views. An open layout encourages entertainment & leisure. The great room seamlessly transitions to the custom kitchen, merging refined details with rich materials. Black walnut was selected for the cabinets & top-of-the-line appliances include: Thermador Cooktop, Subzero Refrigerator, Wolf Digital oven, Miele dishwasher and more. Clear cedar walls, white oak floors, black walnut in the kitchen & blackened steel on stairs & door trims. Each detail is the result of a leading-edge artistic vision, exceptional specifications and thoughtful planning & execution. The home is enveloped in ultra-dense foam insulation to create a hyper-efficient barrier against heat & cold, with a HEPA air filtration system to provide for the most comfortable environment during any season. This property has an incomparable design quality that will captivate and intrigue.

Listed by TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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

141 West Main Street Bennington VT 05201

MLS Number 4834579

  • Commercial
  • County Bennington
  • Acreage 4.29

Turn key operation, development opportunity, you decide! Large & loyal clientele. Elegant property. Owner home on site. No commute to work. First time offered. PRICED TO SELL! The Paradise Motor Inn is located in Bennington, Vermont. Don't miss on this unique opportunity to own one of the finest hospitality establishments in the heart of Southern Vermont. The property is well maintained and offers a variety of added values and experiences: extensive gardens and lawns, tennis courts, pool, pickle ball. Ski, golf, hike, all within a few miles from the Inn.

Listed by TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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

210 South Street Bennington VT 05201

MLS Number 4647611

  • Commercial
  • County Bennington

Great investment opportunity to own the coveted 210 South Street office complex in downtown Bennington, Vermont. With Church Insurance, ADECCO, and VTECH as primary tenants and available space for more, this property is a solid investment opportunity. Modern and full renovation in the past 12 years and including elevator, common restrooms, fire alarm and sprinkler system throughout.

Listed by TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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

69 Upper Taylor Hill Road Winhall VT 05340

Winhall, VT69 Upper Taylor Hill Road

Price$2,950,000

Est. Mortgage: $/month

MLS Number 4848381

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 8
  • Bathroom 9

Stunning country home only minutes to Stratton's base area. Meticulously constructed with careful attention to details and materials it is privately sited on 11 + acres with dramatic views to Bromley, Magic & Okemo. Extensive landscaping. Great room with massive stone fireplace, soaring ceiling and windows to enjoy the expansive view. Kitchen offers all the amenities for the most discerning chef. Large walk-in pantry and large 900+ refrigerated walk in wine room. Quiet space in lovely den with fireplace. 6 ensuite bedrooms and 2 ensuite bunk rooms with custom built-in beds. Master suite has propane fireplace, access to enclosed porch and spa like bath. Large family room with fireplace and access to out door patio with hot tub plus additional game room. Lovely wood floors (Hickory, Pine, walnut) Large partially covered patio with built in grill and out door fireplace. Custom built shed to store wood, tools and toys. Partially furnished list to be provided. An Exceptional property at Stratton - offered for the first time.

Listed by Betsy Cetron of Stratton Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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

1368 West Road Manchester VT 05255

Manchester, VT1368 West Road

Price$2,695,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4854545

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

Enter through the white gate winding to a lengthy circular drive to find this magnificent Manchester Estate that graciously embraces it's private surrounds! Gaze upon 19 natural park-like acres from historic stone walls, established birch groves, meadow land, reflecting pond, woodlands and sprawling lawns all with views to the great Equinox Mountain! This 5200 SF Greek Revival Expanded Cape truly captures comfortable proportions and symmetry in "high country" style. The foyer is lovely as the architectural detail of the sunken dining room opens before you, while open toward the balanced living room on the right and fabulous beamed ceiling family room on the left with center mantle fireplaces. Exemplary symmetry in additions extend toward main level master bedroom suite or soapstone cooks eat-in kitchen...also boasting fireplaces. The upstairs sun drenched landing leads to a Primary Luxury Suite and En suite guest room that also offer fireplaces. Yes, there are 6 fabulous fireplaces! The rear entry foyer is also welcoming with a separate staircase to a forth bedroom suite that also hosts private office needs or game room activities. Every living space walks in and out onto terraces or stone walled gardens that beckon strolls in the fresh air along the pathways. Private, quiet & convenient to Manchester, the attention to detail, the gracious essence, the proportions, symmetry and warmth creates timeless presence! Renovated in 2019. FURNISHED Undeniably among Vermont's Finest!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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

9 Middle Ridge Road Winhall VT 05340

Winhall, VT9 Middle Ridge Road

Price$2,675,000

Est. Mortgage: $/month

MLS Number 4865012

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

Nothing Short of Exceptional, this Luxury Custom built residence, with Stratton Mountain Club membership available, is quietly tucked across from the Base Lodge and Club with Mountain Views and complete convenience to Stratton Mountain Resort. Location, Location , Location- where amenities abound.You'll find premiere craftsmanship and a floorplan that will invite you to entertain and gather together on a grand scale. Cathedral ceilings, walls of glass, wood floors,commanding stone fireplace, custom woodwork and an open layout with great room that flows to dining where you can take in the views and enjoy a roaring fire. The large gourmet kitchen features upscale appliances, stone countertops and oversized island with breakfast bar that opens to wrap around deck and outdoor grilling where you will enjoy lunch on your spring ski days. This mountain home features multiple gathering spaces and no shortage of outdoor apres ski enjoyment. The corner sunroom/den off the great room leads to the deck. A spacious billiard and gameroom doubles as the ensuite bunkhouse for 4 with catheral ceilings and fun for all ages. A lower level family room with 2nd stone fireplace features ping pong, a wetbar/kitchenette for movie night and apres ski. All of this opens to an outdoor patio with 3rd woodburning fireplace and hot tub. You can 't beat the apres ski fun this Stratton getaway is known for. This 6 bedroom/5.5 bath home includes 4 ensuite.Master w/FP, Ski room w built-ins, oversized garage

Listed by Kim Morgan-Wohler of Wohler Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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

81 High Meadow Road Winhall VT 05340

Winhall, VT81 High Meadow Road

Price$2,400,000

Est. Mortgage: $/month

MLS Number 4861130

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

Bring your family and friends to enjoy the Stratton Mountain lifestyle. Your day starts by watching the mountain explode in a sparkling array of colors as the sun's first rays catch the groomers from your master suite. You hit the remote and the TV drops down from the ceiling with the morning weather. Time to get ready for an adventure-another bluebird day on the hill. As the sun continues to rise and fills your gourmet kitchen with day's first light, you look back upon the hill and decide: is it the gondola or the Amex chair first? You may not be able to cut the lift line but this property gives you the option to move to the front of the line and open the door to the Mountain Club. Head there for lunch and/or enjoy an Apres-Ski cocktail. After you head home, you start your outdoor fire pit and hand out the chocolate and marshmallows for a little late day boost. While you step into the hot tub to relax the body and mind, someone else is getting the fire ready. After dinner you have to decide: do you sit by that cracking fire or is to the basement for a little ping pong or air hockey? As you turn off the lights you look out at the hill one more time to check out the army of groomers diligently preparing for the next day's adventure. Tomorrow another adventure begins.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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

349 Kent Hill Road Dorset VT 05251

Dorset, VT349 Kent Hill Road

Price$2,350,000

Est. Mortgage: $/month

MLS Number 4838728

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

Remarkable Dorset Village Property with 4 Private Acres both Landscaped and Wooded available for the first time in 20 years.Constructed in 1935, this home exudes the style of the era with its welcoming foyer with curved open staircase, arched entryways, deep moldings and grand windows. The sunlit, front-to-back living room and the adjoining sun-room, features a fireplace with marble surround.It is both grand in scale for entertaining yet comfortable for relaxing afternoons. Enter into the library/office with another fireplace providing the perfect place to curl up for reading that weekend book. Continue on to the formal dining room with deep ceiling moldings and French doors that open to a marble porch overlooking the lawns and mountain views. Then onto the fully updated kitchen that features double center island, upscale appliances and designated coffee area that opens into the great room with French doors leading out the the lawns and a back staircase.A guest bedroom with bath, office and a half bath complete the first level. From the front foyer, ascend the stairs to the 2nd level that feature two ensuite masters, four guest rooms three baths and a large family room with fireplace and pool table. Spend the afternoons wandering through walking paths of the Pinnacle Town Forest, down the hill to the village for coffee, lunch or dinner or a stroll to the Dorset Playhouse. This treasure is a rare offering in the Village. It's a must see. ( all measurements approximate)

Listed by David Halligan of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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

17 West Branch Road Winhall VT 05340

Winhall, VT17 West Branch Road

Price$2,350,000

Est. Mortgage: $/month

MLS Number 4838716

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

Exceptional architectural features, craftsmanship of the highest caliber, and a location situated near Stratton Mountain Resort are the hallmarks of this distinctive 6-bedroom, 6.5-bath home. Designed for entertaining, the 6000 sq. ft. open layout features a gourmet chef's kitchen with high-end appliances, a commanding stone fireplace that rises through the center of the home, a custom apres-ski pub with mountain views, and a stunning timber-frame mountain lodge room. This ski home is nothing short of breathtaking, with great attention to detail and superior fit and finish. The mudroom rivals luxurious locker rooms of private country clubs; there is abundant storage space for all your year-round gear. Rich oak flooring can be found throughout the home. The whole house has radiant heat, providing unsurpassed warmth for your comfort. Experience living well and make this residence your private retreat. Stratton Mountain Club membership is available. Winter Resort Ski Shuttle picks you up right at the driveway and gets you to and from the slopes in no time. Located only half a mile from the base lodge, there is a year-round maintained walking path back to the North Brookwood neighborhood location.

Listed by Robert Sabol of Wohler Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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

14 Morse Road Bennington VT 05201

MLS Number 4794904

  • Commercial
  • County Bennington
  • Acreage 4.73

LONG TERM LEASE WITH $168,000 NET INCOME - 50,000 sq. ft industrial building and land for sale just off the highway, well kept and ready for a new owner. Opportunities like this don't come around often in the Bennington area. Other details include: Six - 1,000 gallon propane tanks installed 2017 (owned by the property owner - not the propane company), Two - 8' overhead loading dock doors, Six - 12' overhead doors at ground level, 1,200 amp 3 phase service, 750 KVA transformer (owned by the property owner - not the electric company), Two sprinkler / fire suppression systems, 6,000 sq. ft office/common areas, Two sets of bathrooms (4 total), 12 main offices, 1 conference room, 1 large break room, Other open / cubicle areas, RFID door lock access system at all main doors, 6,000 sq. ft mezzanine storage.

Listed by TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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

310 & 316 Church Street Dorset VT 05251

Dorset, VT310 & 316 Church Street

Price$2,200,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4872414

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 2
  • Bathroom 3

Continental Flare and innovative design are the hallmarks of this exceptional 12-acre estate in the heart of Dorset, Vermont. The graceful and complete renovation of the of the originally built 1919 main residence has been architecturally and stylishly transformed in 2011 to a luxury level. Beginning with the dramatic two-story coved ceiling entry hall leading to a 14-foot Palladium window and door overlooking a series of marble and sandstone lined reflecting pools, cascading waterfall and gardens. The formal living room has European details including the Italianate marble fireplace mantle and the book lined library offers quiet moments around the cozy fireplace. An exquisite kitchen/pantry focuses around the stunning Lacanche French stove and guests can find their places in the adjoining curved windowed formal dining room with a commanding views of the distant mountains. A master bedroom suite and guest suite bring restive nights to all. This country estate also has a new barn and a separate picturesque three bedroom and bath modernized carriage house with living, dining and kitchen rooms. All the charming amenities Dorset has to offer are in easy walking distance including: quaint country inns, regional theatre, gourmet grocer, bakery, library and close proximity to four golf courses and three ski areas. This is a rare offering for the discriminating Purchaser.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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

369 Sykes Hollow Road Rupert VT 05761

Rupert, VT369 Sykes Hollow Road

Price$2,000,000

Est. Mortgage: $/month

MLS Number 4841751

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

Situated in Southern Vermont's Mettowee Valley; minutes from Dorset/Manchester and close proximity to Albany, Saratoga, and Saugerties, you can't help but recognize the magical, calm feeling as you approach Sykes Hollow Farm. Upon turning up the tree lined drive, passing three grass paddocks, large fields with Run-In Sheds, Derby Field and a competition sized outdoor Ring (100 x 200) the charming reimagined (2011) farmhouse awaits your arrival. Consisting of four bedrooms and three baths, and a wonderful open country kitchen where there is room for guests to help with dinner preparations before adjourning to the wood beamed, candle lit dining room. After dinner you can curl up with a good book or board game in front of a roaring fire in the cozy living room. This home also enjoys a running brook, swimming and skating pond, seven stall show barn and 70 x 144 indoor ring. Add a two-bedroom guest cottage for family or guests plus a barn with a studio/groom apartment as well as space for yoga, dance or exercise in loft area. This 33-acre gem awaits the buyer who is looking to embrace all a Southern Vermont lifestyle has to offer, including golf, hiking, snow shoeing, skiing and the opportunity to make lifelong friends and memories. All measurements approximate.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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

300 Fern Hill Dorset VT 05251

Dorset, VT300 Fern Hill

Price$1,999,000

Est. Mortgage: $/month

MLS Number 4874125

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

After a magazine worthy renovation, Fern Hill is a breathtaking 1890 carriage house with state-of-the-art conveniences. The home features a gourmet eat-in kitchen, a luxurious master-suite and a spectacular view of mountains, pond and gardens. Reimagined and restored, the property offers five bedrooms, 2 ship latter lofts and 5 bathrooms (plus two half baths) in 5,000 square feet. Spanning 4 acres, the impressive property features a European swimming pond (with a sand beach) meditation garden and a mountain stream winding through the property. The blue-stone patio features a built-in grill, abundant perennial gardens, stone walls, a magical fenced garden shed/ chicken coop. The post and beam garage offers a 3 season artist studio. Pure heaven in Dorset Vermont.

Listed by Moira Spivey of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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

9 Stone House Road Winhall VT 05340

Winhall, VT9 Stone House Road

Price$1,925,000

Est. Mortgage: $/month

MLS Number 4833668

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

Spending more time at home makes you realize how much living in a place you love matters! Wouldn't you love to live at Stratton Resort? The shuttle to mountain, Sports Center membership, skiing, biking, fishing is all literally in your backyard. Ever-changing views of Stratton Mountain and golf course location add to the appeal of this outstanding 2.3 acre property. Entertain with over 6000 square feet. Living room features soaring ceilings, Rumford fireplace and oak hardwood floors.The chef's kitchen with porcelain farm sink, granite counters, stainless steel appliances and attached butler's pantry make feeding the masses simple. Rest and relax in Main bedroom sanctuary with jetted soaking tub in en suite bathroom, walk in closet/dressing room and private office. Guests enjoy 4 additional bedrooms and 6 bathrooms. Home amenities include sauna, hot tub, screened in porch, custom designed fire pit, patio for grilling and 2 car garage. Please call to experience one of the most spectacular settings in Vermont.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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

581 North Bennington Road Bennington VT 05201

MLS Number 4733230

  • Commercial
  • County Bennington
  • Acreage 18

Parcel is an established commercial zone . Area includes Home Depot Center, Hampton Inn, Hannafords Shopping Center, Chilis & several car dealerships. Highly visible from connector road to Rte 279 and US Rte 7 N & is almost directly across from entrance to both. Property includes rail siding.

Listed by Kathleen Hoisington of Hoisington Realty, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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

29 Deeryard Road Winhall VT 05340

Winhall, VT29 Deeryard Road, Unit 21

Price$1,800,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4869036

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

GREEN ACRES IS THE PLACE TO BE............................................. Unprecedented views from this amazing mountain contemporary. BIG Stratton views and beyond await you on 26 rolling acres with all the recreation at your doorstep you can possibly take in, in one day. This gorgeous property is perfect for entertaining your large family or guest gatherings with many common areas inside & out. Attractive stone patios, porches and decks allow you to enjoy the scenic outdoors while almost every interior room boasts magnificent mtn views. Over the years the current owners have renovated, updated & added additional space to accommodate their active lifestyle. The enormous recreation room on the upper level overlooking the back patio is a huge feature you will greatly appreciate. Sleek kitchen w/granite counter tops, breakfast table & island. Comfortable media room, den with additional fireplace and loft office area add extra living spaces for you & your company. Plenty of sleeping accommodations on multiple levels. Wine cellar is conveniently located below the dining/kitchen. Private screened in porch. Sunken hot tub. Solar panels on the roof. Take a walk up to the upper property & after a vigorous game of tennis on a well maintained court follow the groomed path down to a beautiful, clean swimming pond 9' deep or simply jump in the outdoor shower. Enjoy walking & snowshoeing trails already laid out for you. We can't wait for you to see this extraordinary listing!

Listed by Terry Hill of Mountain Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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

147 Green Peak Orchard North Road Dorset VT 05253

MLS Number 4850153

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

The Best of Both Worlds! This gracious Federal style Colonial farmhouse is Vermont living at its best! Super location (Manchester & Dorset each 10 minutes away) nestled in Green Peak Orchard Association, with all the privacy and seclusion that this enclave offers. Designed & constructed in 2003-4, this exquisite custom home offers many fine details & a stunning location. The main floor flows nicely from formal living room, den & dining room into a showstopper kitchen & keeping room. Mudroom with antique brick floor leads to garage, front porch & screened-in porch off kitchen area. Two working fireplaces, wide pine board flooring, local marble & soapstone countertops & custom cabinetry throughout. Upstairs offers a master bedroom, dressing room and bath 4 additional bedrooms and office/study space. Two attics and full basement with laundry, gym area and office. Grounds contain a woodland “moon” garden, mature crab apple and VT vernacular trees and shrubs and a glorious stand of white Birches. Front & back hand-hewn stone walls with rocks excavated from the property & local stone walkway stones & pavers. This lovely home sits on 11.9 acres with woods to explore & enjoy as well as a wide field off the back lawn that once housed an apple orchard. Lots of room to expand and make it your own, this home is one not to be missed! All measurements approximate.

Listed by David Halligan of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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

219 Northside Drive Bennington VT 05201

Bennington, VT219 Northside Drive

Price$1,750,000

Est. Mortgage: $/month

MLS Number 4853014

  • Land
  • County Bennington
  • Property Type Land
  • Acreage 2.82

Almost 3 acres on NORTHSIDE DRIVE, one of Bennington County's busiest roads (14K cars daily). Close to major shopping centers, hotels/motels, restaurants, etc. Easily accessed via traffic circle, Rt 279 bypass, Rt 7, 7A, and 67A. Existing successful business ready for new owner or premier location for your business opportunity. Zoning with DRB approval includes but is not limited to: retail, restaurant, indoor recreation, self storage, car wash, daycare, financial institution, gas station, hotel, medical clinic, motor vehicle sales and service, RV park, business office, and warehouse. Originally built as a bowling alley, and taken over by current owner 40 years ago, who has invested in substantial improvements. Modern interior design, new pins purchased last year, everything front & back has been computerized, including sound & security systems. Two state-of-the-art high-definition golf simulators bring in a different crowd and stream of revenue. Kitchen has gas range, fryers, flat top, proper hood ventilation, freezers, and adjacent storage room. Bar with 2 beer coolers and 8-tap kegerator. Two accessible restrooms, janitorial room, security office, utility room, mechanics workshop, attached garage. Includes most furniture, fixtures, and equipment. Oversized storage building, plus 2 rental properties: single family home $950/month and privately-owned trailer $300/month lot rent. See the potential in the existing buildings, or start over with your custom plans.

Listed by Jenifer Hoffman of Hoffman Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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

219 Northside Drive Bennington VT 05201

MLS Number 4853013

  • Commercial
  • County Bennington
  • Acreage 2.82

Almost 3 acres on NORTHSIDE DRIVE, one of Bennington County's busiest roads (14K cars daily). Close to major shopping centers, hotels/motels, restaurants, etc. Easily accessed via traffic circle, Rt 279 bypass, Rt 7, 7A, and 67A. Existing successful business ready for new owner or premier location for your business opportunity. Zoning with DRB approval includes but is not limited to: retail, restaurant, indoor recreation, self storage, car wash, daycare, financial institution, gas station, hotel, medical clinic, motor vehicle sales and service, RV park, business office, and warehouse. Originally built as a bowling alley, and taken over by current owner 40 years ago, who has invested in substantial improvements. Modern interior design, new pins purchased last year, everything front & back has been computerized, including sound & security systems. Two state-of-the-art high-definition golf simulators bring in a different crowd and stream of revenue. Kitchen has gas range, fryers, flat top, proper hood ventilation, freezers, and adjacent storage room. Bar with 2 beer coolers and 8-tap kegerator. Two accessible restrooms, janitorial room, security office, utility room, mechanics workshop, attached garage. Includes most furniture, fixtures, and equipment. Oversized storage building, plus 2 rental properties: single family home $950/month and privately-owned trailer $300/month lot rent. See the potential in the existing buildings, or start over with your custom plans.

Listed by Jenifer Hoffman of Hoffman Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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 2021 New England Real Estate Network, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate for sale on this web site comes in part from the IDX Program of NEREN. 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 July 30, 2021.