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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 802-760-3100 or contact us online.

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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: 2.94% last updated on May 13, 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.

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275 High Fields Lane Manchester VT 05254

Manchester, VT275 High Fields Lane

Price$4,200,000

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 sunsets 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: 2.94% last updated on May 13, 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.

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779 Wind Hill Road Dorset VT 05251

Dorset, VT779 Wind Hill Road

Price$3,500,000

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, VT 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 home is custom crafted with an impeccable selection of materials throughout. There is a luminous great room with 25-foot high ceilings featuring floor to ceiling windows that highlight the expansive mountain views. In an open layout that encourages entertainment & leisure, the great room seamlessly transitions to the custom kitchen, merging refined detail with rich materials. Black walnut was selected for the cabinets & the top-of-the-line appliances include Thermador Cooktop, Subzero Refrigerator, Wolf Digital oven, Miele dishwasher and more. All of the materials were meticulously chosen, including clear cedar walls, white oak floors, black walnut in the kitchen & blackened steel on the stairs & door trims. Every detail is the result of a leading-edge artistic vision, exceptional specifications and thoughtful planning & execution. The entire house is enveloped in ultra-dense foam insulation to create a hyper-efficient barrier against heat & cold and with a HEPA air filtration system to provide for the most comfortable environment during any season. This home has an incomparable design quality that will captivate and intrigue you.

Listed by TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 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.

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440 Marcia Lane Dorset VT 05251

Dorset, VT440 Marcia Lane

Price$3,500,000

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: 2.94% last updated on May 13, 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.

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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: 2.94% last updated on May 13, 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.

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230 School Street Bennington VT 05201

MLS Number 4831584

  • Commercial
  • County Bennington
  • Acreage 5.7

This is your chance to own an established multi-sport training/camp facility in downtown Bennington, Vermont. The former Catamount School has been converted and refurbished as a sports training complex. Fully permitted with over 67,000 square feet of space including several indoor turf facilities, full cafeteria, 120 dorm rooms, parking, and outdoor fields - this facility is ready and turn key! Whether you want to run a soccer, lacrosse, basketball, baseball, or any other sport camp or training operation - this is the place for you. In addition, there is unused indoor space ready for expansion! Formerly the Catamount School with street footage on Route 7 and School Street and plenty of off-street parking - this property awaits your visit! Also included in sale is all kitchen equipment, furnishings, sporting equipment, and facility maintenance tools/equipment.

Listed by TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 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.

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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: 2.94% last updated on May 13, 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.

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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: 2.94% last updated on May 13, 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.

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727 North Road Manchester VT 05255

Manchester, VT727 North Road

Price$2,950,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4815982

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

Serene 10 acre Manchester Splendor is surrounded by 360 degree pastoral mountain views that speaks to all who gather with an indoor - outdoor embrace! This exceptional, ideally located 7700 SF sunlit residence offers rich architectural detail that is evident from walnut flooring, crown moldings and 9 plus foot ceilings to three wonderful marble fireplaces and extraordinary stone & marble terracing that seamlessly transitions from room to fresh air. The gourmet's kitchen features top of the line appliances, native soap stone counter tops, wet bar, butlers pantry, dining, a generous marble island all open to the magnificent step down family room with airy vault ceiling. The living room offers a marble fireplace centered and open either side to the generous sun room beyond hosting natural light all day until the sun sets! The practical aspects of the house boasts a large laundry mud room area, beverage bar salon, storage, and front/back stair cases to the second level! The primary suite promotes every benefit of luxury: closets, soaking tub with view, large shower, fireplace seating, and an exceptional balcony taking in sunset views over the lush landscaped grounds. Every bedroom offers ample baths & lounging areas. Lower walk out level offers enormous climate control storage, large gym & play room with steam shower and hot tub spa! Steps away the 40 X 20 Gunite saltwater heated pool, cabana, pergola, gas fire pit,outdoor shower & guest house, Barn for toys or horses! Sublime!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 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.

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1368 West Road Manchester VT 05255

Manchester, VT1368 West Road

Price$2,900,000

Est. Mortgage: $/month

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...creating timeless presence...Renovated in 2019...Undeniably among Vermont's Finest!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 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.

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466 Marcia Lane Dorset VT 05251

Dorset, VT466 Marcia Lane

Price$2,900,000

Est. Mortgage: $/month

Pending

MLS Number 4744398

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

Dorset Hollow Pinnacle offering 180 trail laced acres at the height of the Dorset's Upper Hollow Road. Amazing Sunsets... Stunning Long Range Mountain Vista's are captured immediately from the impressive foyer and continues to captivate from room to room throughout this architect designed residence! With over 7500 light filled square feet this gracious residence with lovely custom cabinetry and crown moldings supports Vermont living at it's finest! Massive Stone fireplace walls grace the cherry paneled library as well as the 50 X 22 expansive Great Room Kitchen featuring an incredible breakfast room and a Honed Costa Esmeralda island, Wolf appliances and handsome coffer ceiling for the living/dining. Just off the kitchen are the well planned wet bar, wine cellar and pantries. Warm radiant heated hardwood floors lead to the 3 room primary suite that includes sitting rm/office, exercise room and luxury bath with relaxing soaking tub or shower. 4 bedrooms and baths up comfortably accommodate guests and family. A bonus room integrates nicely for full time use supporting any hobby or media interest. Full light filled basement and Carriage house offers expansion for guest quarters within the generous floor plan if desired. Over-sized garages, attached or detached offer room for all the toys! Raised stone terrace creates indoor / outdoor ease for all living areas that offers heated path to the spa, grilling area & outdoor fireplace. This property meets field and stream perfection!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 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.

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21 West Road Bennington VT 05201

MLS Number 4851427

  • Commercial
  • County Bennington
  • Acreage 11.1

This landmark inn has a stellar reputation as a premier lodging and dining venue that spans 60 years. Each of the 11 guest rooms is creatively decorated and attractively furnished with an artistic flair for color and texture in fabrics and wall coatings. 7 of the guest rooms have gas or wood-burning fireplaces. The present owners have extensively renovated the inn over the past 16 years taking great care to maintain the integrity of the inn's historic architectural features. The result is an exceptional blending of vintage architectural features and contemporary guest room and bath design. Manager's apartment onsite. Owners' 7 bedroom Greek Revival home located across the road is available for purchase separately. This inn has a long, successful track record of being a reliably strong financial performer with an annualized occupancy rate over 60%. Currently operated as a high end Bed & Breakfast Inn, a successful, fine dining restaurant was operated onsite for decades. All licenses, fixtures and equipment are in place to reopen the restaurant should new owners choose to maximize the use of this superb facility.

Listed by Pamela Long of East Coast Inn Brokers

$
$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 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.

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21 West Road Bennington VT 05201

Bennington, VT21 West Road

Price$2,495,000

Est. Mortgage: $/month

MLS Number 4849646

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 12
  • Bathroom 16

This exquisitely appointed circa 1913 mansion is privately situated in the prestigious Historic District of Old Bennington amidst 11 acres of parklike grounds. The mansion has been masterfully restored and updated with an eye to preserving its period architectural features. The first floor features an intimate living room with wet bar and wood-burning fireplace, a spacious formal dining room with wood-burning fireplace, a stunning conservatory with brick floor and two walls of divided glass windows and French doors. This property boasts a fully equipped commercial grade kitchen with a spacious footprint. A great space to create your dream kitchen. The 7 of the 12 bedrooms have gas or wood-burning fireplaces and individually controlled heat. En suite bathrooms are tastefully updated. An in-law apartment and 2 cottage suites offer the opportunity for multi-generational living. The property has operated as a highly successful inn for decades providing new owners the opportunity to continue the lucrative inn business or to rent the cottage suites and in-law apartment for supplemental income. Large out-building has possibility to be an oversized, two-car garage with structural upgrades. The stylish furnishings are included in the sale subject to a short list of exclusions. This property can also be purchased together with the Greek Revival home located directly across the road. See MLS #4840013.

Listed by Pamela Long of East Coast Inn Brokers

$
$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 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.

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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 open layout features a gourmet chef's kitchen with high-end appliances, a commanding stone fireplace which rises through the center of the home, an apres' ski custom pub with views to the mountain, 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. There is rich oak flooring throughout the home. The whole house has radiant heat providing unsurpassed warmth for your comfort. Experience living well and come make this residence your private retreat. The Seller can transfer their private Stratton Alpine Club membership to the buyer with the buyer paying club fees.

Listed by Robert Sabol of Wohler Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 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.

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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: 2.94% last updated on May 13, 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.

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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: 2.94% last updated on May 13, 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.

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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: 2.94% last updated on May 13, 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.

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455 VT Route 30 Winhall VT 05340

Winhall, VT455 VT Route 30

Price$1,995,000

Est. Mortgage: $/month

MLS Number 4844261

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

A truly one-of-a-kind property offering 175(+/-) acres, ideally located in the heart of Ski Country between Bromley and Stratton Ski Resorts. This very unique property consists of a Colonial with barn and garage on 7+ acres with 50+ acres next door and an additional 117+ acres in the back, bordering National Forest and showcasing top of the world views of Stratton Mountain. The residence has true Vermont charm and allows plenty of room for kids to play in the large meadow located behind the barn. It provides a unique opportunity to stay in residence while building your Vermont Dream home(s) on one or both of the adjoining lots. This would make a great Guest House for family and friends or a nice Ski Rental for additional income. For those thinking of developing this large parcel, we can provide the preliminary plans and documentation for a 6 to 7 acre lot subdivision. A property like this doesn't come around often so don't miss out on this extraordinary opportunity to enjoy the peaceful beauty and the lifestyle Vermont has to offer!

Listed by Tammy Dillman and Joseph Cajzer of Josiah Allen Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 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.

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97 North Branch Road Winhall VT 05155

Winhall, VT97 North Branch Road

Price$1,975,000

Est. Mortgage: $/month

MLS Number 4855856

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

One of the Stratton resort's iconic homes. Nestled along the shore of Stratton Lake with direct water access on one side and Stratton Mountain Golf Course on the other. Five bedrooms and six full baths, plus common space galore. Family room, den, loft, two car garage. Great for large family or two families. Exceptional property insuring privacy, views and convenience! Stratton ski shuttle comes right to the foot of your driveway. Finnish Fireplace a unique feature, warming the core of the home during the winter months.

Listed by John Sikes of Stratton Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 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.

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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: 2.94% last updated on May 13, 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.

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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: 2.94% last updated on May 13, 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.

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348 Neilson Road Rupert VT 05768

Rupert, VT348 Neilson Road

Price$1,800,000

Est. Mortgage: $/month

Pending

MLS Number 4822061

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

Country charm and sophistication join hands in this special home perched high on a meadow in coveted Sykes Hollow-a perfectly tranquil setting. This home sits on 69 sub dividable acres with outstanding long range mountain views to the southwest. Equine friendly with a mix of flat pastures and woodlands. Tastefully appointed with plenty of natural light throughout. Amazing outdoor venue featuring a large covered porch and an adjacent stone patio. Entering this end-of-the-road- property one immediately gets a sense of peace and tranquility. Former horse stables converted into a 3 season guest house oozes with charm. Lots of trails for recreational use. Horses, ATV, Snowmobiling right out the door. 5 minutes to the Dorset Green. A very special offering. Simply sublime. Come take a look!

Listed by David Shehadi of Josiah Allen Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 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.

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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!On the market for the first time, this gracious Federal style colonial farmhouse is Vermont living at its finest!The location is super - with Manchester and Dorset each 10 minutes away, yet nestled into Green Peak Orchard with all of the privacy and seclusion that this enclave offers.Designed and built in 2005 by RH Adams, this custom home offers many fine details, a stunning location, and views at every turn.The main floor offers great flow from formal living room, study, and dining room leading to the showstopper kitchen and keeping room.An antique brick floor mudroom leads to garage as well as the front porch; a screened-in porch is off the keeping room.Two working brick fireplaces, wide board floors, local marble and soapstone countertops and custom cabinetry throughout.Upstairs offers a master bedroom with adjoining bath,4 additional bedrooms and an office/study space.Two attics and a full basement with laundry, gym area and office complete this exceptional offering. Grounds contain a custom designed woodland “moon” garden, mature crab apple trees, Vermont vernacular trees and shrubs.Front and back hand-hewn stonewalls with rocks excavated from this property and local stone walks.Views to Mount Aeolus and Equinox.This lovely home sits on 11.9 acres with woods to explore and enjoy as well as a wide field off the lawn, that once housed an apple orchard.Lots of room to expand and make it your own, this home is one not to miss. (Measures approx.)

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 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.

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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: 2.94% last updated on May 13, 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.

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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: 2.94% last updated on May 13, 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

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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 May 15, 2021.