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Bennington County

Browse all available real estate in Bennington County, Vermont. 

Find Homes for Sale in Bennington County VT

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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
  • Square Feet 12,126
  • Bathroom 10
  • Bedrooms 6
  • Construction Existing

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 ch√Ęteau, 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

$
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%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* 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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999 Route 30 Rupert VT 05761

Rupert, VT999 Route 30

Price$3,995,000

Est. Mortgage: $/month

MLS Number 4904677

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 7
  • Square Feet 5,094

Hagarbook Farm completely restored 5034 SF C. 1767 Residence consisting of magnificent Mettowee River frontage interior to the 320 acres, Hagar Brook and Waterfall, Harmons Mint Historic Site, Pond, Agricultural Fields, Extensive Trail System and View Sites galore! The Land Straddles both East Rupert and Dorset. Add significant buildings in lovely condition: 750 SF Guest House, Barn 37 X 100, Tractor Barn 26 X 50, Horse Barn 50 X 28 and additional out buildings--24 X 18, 20 X 14, 20 X 12, 16 X 12, 40 X 24! An exemplary eighteenth century compound approximately 3 miles north of the Dorset Green. The Great-Room Kitchen with exposed post and beam framing is the welcoming hearth of the home which walks out to the wrap around porch or sun room to the west where the living extends upon a wonderful level stone walled terrace overlooking the grounds and river beyond. Crisp architectural details witnessed in every room; Dining, Living, Family, Office and 4 Wonderful Bedrooms up. There are 5 baths, 2 half baths and a guest house ... Whether it's agricultural or equine interest, stream & field, auto collector, historical appreciation or family gathering ideals, this property is a treasure. Vermont Current Use real estate tax benefits for the next steward to embrace. 320 acres in the prized Mettowee Valley nearby Dorset!!!

Listed by Charles Mauro of Josiah Allen Real Estate,Inc.

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$
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$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* 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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1048 Black Hole Hollow Road Arlington VT 05250

MLS Number 4868628

  • Residential Single Family
  • Bedrooms 7
  • Bathroom 8
  • Square Feet 8,154
  • Construction Existing

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

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$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* 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$3,950,000

Est. Mortgage: $/month

MLS Number 4911369

  • Residential Single Family
  • Bedrooms 6
  • Bathroom 7
  • Construction Existing
  • Square Feet 6,703

Stratton Mountain Estate-Rarely does one have the opportunity to acquire an iconic estate with a newly expanded and renovated grand lodge and guest house with extraordinary views of Stratton Mountain trails. This exceptional renovation of a Frank Lloyd Wright designed Pearl Buck property on 35+/- acres is just minutes to the Stratton Mountain Base Lodge. With commanding southerly views of Stratton Mountain, and surrounding ridge lines with sunset views to the west, this dramatic 4 bedroom/ 4.5 bath lodge is without comparison and the last rare parcel of this size near the resort with a world of privacy and tranquility. Three stone fireplaces, large beams, walls of glass and VIEWS, VIEWS, VIEWS. Additional 2BR/2BA Guest House, garage, pond and tennis court. Patios, Stonework, outdoor spaces.enhance the stunning location. Additional building sites available. Situated in the heart of everything the region has to offer througout the seasons. World Class professional theater at Weston and Dorset, the Manchester Music Festival, The Dorset Summer Equestrian Festival, Hiking, biking, kayaking, shopping and dining. Fall foliage, first tacks on powder days and the glorious Green Mountain Summers beckon. This one of a kind property has the essence of a true mountain lodge, set into its surroundings with a tranquil and peaceful vantage point. Adventure is at your doorstep.Additional parcels available. Make plans to visit this newly expanded and renovated property. You'll be enthralled!

Listed by Kim Morgan-Wohler of Wohler Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* 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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160 Benmont Avenue Bennington VT 05201
Pending

MLS Number 4888929

  • Commercial
  • Year Built 1865
  • Acreage 10.7

Opportunity of a lifetime! Imagine owning one of America's largest historic mills? Built in 1865 additions into 1935 and strategically placed in the heart of the thriving Bennington town, this mill began with Civil war uniforms, then continued as a woolen mill for decades, went on to become a knitting factory and a paper mill too. In the early 1900's over 1/3 of the area was employed here. Since the current owner invested in the 1980's and 90's, it has continued to grow and is now a booming mixed use building nearly at full occupancy creating space for medical and counseling offices, College classrooms, Gyms and health oriented spaces, Manufacturing companies, design studios, attorney offices, retails stores, auto work, graphic designers, artist studios, storage spaces and even housing! You name it, it can be done here. The potential is unlimited. There is a huge need for housing in our area and the prospect for condo units in this place is viable. To rebuild this incredible structure with the wood beams, steel infrastructure and brick construction would cost over 25 million in today's dollars. The entire building has been updated with electrical, plumbing, heating and an elevator system. With all the new, there is still so much character from the many lifetimes this property has traveled through. With 10+ acres and plenty of parking plus river frontage!

Listed by Lillian West of Maple Leaf Realty

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$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* 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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90 Snow Valley Road Winhall VT 05340

Winhall, VT90 Snow Valley Road

Price$3,650,000

Est. Mortgage: $/month

MLS Number 4924477

  • Land
  • Acreage 387
  • Utilities None
  • Zoning Rec

AUCTION: BID 09-15 SEPTEMBER. Buy now for $3.65M. $2.05M Reserve. Showings Daily 1-4pm & by Appointment. Discover the potential of an alpine escape beyond compare in Snow Valley. Once a beloved winter destination in gorgeous Southern Vermont, Snow Valley operated largely under the radar from 1939 to approximately 1982, with a proud reputation as one of the nation's very first ski areas and the very first snowboard area. The stunning 390+ acre property forms an ideal blank canvas for potential future home or family compound with all of the benefits of a resort experience. The region boasts over 120 inches of snowfall per year, truly perfect for the downhill and cross-country skiing Snow Valley was once renowned for, with its north-facing configuration of mountains that “funnel” snow well into the spring season. Picture-perfect vistas of Vermont countryside stretch in every direction, Snow Valley is ready to exceed every expectation.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* 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$3,495,000

Est. Mortgage: $/month

MLS Number 4912881

  • Residential Single Family
  • Construction Existing
  • Bedrooms 7
  • Bathroom 5
  • Square Feet 4,866

Do you like to entertain and host large crowds? Forever Farm is the setting! Have a sit down holiday dinner for many in the spacious cooks kitchen, retire by the wood paneled fireplace with an after dinner drink, or enjoy the covered porches during foliage. This Manchester compound situated conveniently to town shopping, restaurants, the Equinox resort and area ski mountains is a great year round gem! Work out daily in your home gym, skate on the pond during the winter months while family and friends hit the slopes! Bring one and all! The main home offers four guest bedrooms, two en-suite masters and a tastefully appointed three bedroom/two bath guest house above fully restored barn. This home is equipped with horse stalls, riding area and close to area trail systems. This is a rare offering.

Listed by Andrea Kaplan of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* 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$3,200,000

Est. Mortgage: $/month

MLS Number 4905858

  • Residential Single Family
  • Construction Existing
  • Bedrooms 9
  • Bathroom 7
  • Square Feet 6,956

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 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. 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: 5.22% last updated on Aug 11, 2022
* 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$3,000,000

Est. Mortgage: $/month

MLS Number 4915207

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 8
  • Square Feet 8,700

This exceptional secluded country estate with breathtaking mountain views sits on a rolling hill in Dorset's exclusive Upper Hollow with 17.25 acres to explore. Showcasing the best in craftsmanship, sophisticated finishes, manicured stone patios, terraces, and walkways, makes this a beautifully refined residence. A custom wood beamed barn hosts an exclusive indoor basketball court and pool house that is beyond compare. Plans to renovate the current floor plan to open the spacious and welcoming gathering and entering space is underway. Whether you prefer a classically designed New England home or a more contemporary flow, the home boasts wide pine floors, crown molding, wainscoting, slate, marble and soapstone throughout. The living areas feature post and beam finishes and open to a covered wrap around porch and stone patio with an outdoor kitchen. The grand Master suite displays a dramatic Benson wood post and beam architecture warming the private retreat. You'll enjoy this special property for its ability to host all of your guests with 5 en-suite bedrooms, 3 wood burning fireplaces, and game room, you'll have plenty of room to gather, entertain or just lounge by the pool. 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: 5.22% last updated on Aug 11, 2022
* 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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674 Dorset Hollow Road Dorset VT 05091

Dorset, VT674 Dorset Hollow Road

Price$2,995,000

Est. Mortgage: $/month

Pending

MLS Number 4921271

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 6
  • Square Feet 4,711

Quiet seclusion, view of the mountains, sounds of the Mettawee River and less than a mile to the Dorset village green. This beautifully maintained property has a recently renovated four bedroom main house, one bedroom guest cottage and studio set on a pastoral landscape of 43 acres. Located in the highly desirable Dorset Hollow, it has some of the best trails and walking loops out the back door. Throughout the house, the rich patina of antique wood floors and attention to detail brings the past and the present into harmony. The screened in porch and stone terrace connect the inside with the outside. The spacious, light-filled kitchen has room for twelve people to eat comfortably and plenty of workspace to prepare the meals. The kitchen is a favorite spot to congregate and watch birds at the winter feeders and features a full view of the Mettawee. Part of the recent renovations include the addition of the Primary Bedroom Suite on the main level. Designed by Bennington architect, Michael Baker, it blends seamlessly with the main house, while adding height, exposed beams and easterly views of the Green Mountains. The over-sized window frames magnificent views of the garden, pool, back pasture and Netop Mountain. This includes a redesign of the library with an extensive addition of bookshelves, slate floor and access to the heated, salt-water pool. High speed internet & A/C. 1,000 ft of river frontage for fishing and swimming, walking/hiking paths, berry bushes.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* 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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166 McKeighan Road Rupert VT 05776

Rupert, VT166 McKeighan Road

Price$2,950,000

Est. Mortgage: $/month

MLS Number 4900123

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 5,956

An estate for the most discerning of buyers. Have you been looking for an estate that combines exquisite details, views, and options for unlimited uses along with privacy? Need a gentlemen's farm for your pleasure horses? An estate suitable for an established events person? If so, this property is for you! 267.5 acres of rolling hills. Here you will find a custom built owner's residence which combines the moving of two barns which were rebuilt into one post and beam, owners residence. The detailing is second to none. A few steps from this home is the most amazing of pool houses which has every upgrade imaginable and allows for swimming 365 days/year, in all weather. There are four independent living accommodations along with a tractor barn, 6 bay animal pen, an animal holding barn with a separate veterinary room with heat and water, and walk in cooler. All electrical is underground. There are four ponds. No chemicals have been used anywhere on this land for the past 17 years so organic certification is possible. This is the estate to be at if another pandemic hits. This property is perfect for destination weddings, family retreats, corporate events and so much more. Come see for yourself, everything you could possibly need is here. All measurements are approximate and are only for the main house. There is a whole farm diesel generator and a propane generator for main house and pool.

Listed by Lynn Rawson of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* 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
  • Year Built 1963
  • Acreage 4.29

Turn-key operation or development opportunity, you decide! Large and 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 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, and pickle ball. Ski, golf, or hike, all within a few miles from the Inn.

Listed by Marek Kovac and Paul William Carroccio of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* 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 2022 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 August 14, 2022 5:39 AM EDT.

 
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