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Bennington VT Real Estate

Bennington is the oldest county in Vermont.  Bennington not only has abundant cultural resources like the Bennington Museum and Southern Vermont Art Center, but is also served by well respected  instutions such as Southern Vermont College and Bennington College.

The largest towns in Bennington County are Bennington and Shaftsbury.

1048 Black Hole Hollow Rd, Arlington, VT 05250

Price$3,700,000

Est. Mortgage: $/month

MLS Number 4502293

  • Residential Single Family
  • Listing Agent Name T Story Jenks
  • Bedrooms 8
  • Bathroom 7
  • Construction Existing

The serene setting of Black Hole Hollow Farm in a quiet valley on the border of Vermont and New York is threaded by the White Creek brook, tiered ponds and 30 miles of trails on 948 acres. The 6-bedroom, 8,143-square-foot main house is surrounded by English-style country gardens with the mountains as backdrop. The original 1772 farmhouse was expanded and designed by noted architect Jerome Cerny. Living room, dining room and downstairs bedrooms open to the gardens and the recently updated kitchen is a welcoming hub with its AGA stove. The farm has a rich history including visits from author Ian Fleming who gained inspiration for several of his James Bond books, and former owner Josephine Hartford Bryce, heir to the A&P dynasty. There is a large greenhouse with sitting area and Koi pond. Other buildings include 4 additional residences, a 2-bedroom apartment, horse & hay barns and a sugar house. Only 7 miles from Cambridge, NY, 30 miles to Saratoga, and 26 miles to Bennington, VT.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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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111 Marcia Lane, Dorset, VT 05251

Price$3,500,000

Est. Mortgage: $/month

MLS Number 4711215

  • Residential Single Family
  • Listing Agent Name Lisa Sullivan
  • Construction Existing
  • Bathroom 7
  • Bedrooms 4

Rarely does a property of this scale and quality come on the market. Set on 18 acres in beautiful Dorset Hollow, it features the main house, a separate 4,470 square foot guest house, large pond and breath taking mountain views that include Owl's Head and Mount Equinox. The custom designed and beautifully built main house offers a country "tavern" kitchen of antique wood, an exceptional great room opening to an expansive covered porch, and stone terraces. The oversized master suite includes his and hers walk-in closets with custom cabinetry, mountain views and a separate sitting/bedroom with its own bath and vistas. Two ensuite second floor guest rooms each enjoy captivating views. The guest house rivals the main house with an open kitchen and living area with a large brick fireplace. There are three ensuite bedrooms, covered deck, stone patio and astounding views. The lower level "magic kingdom" bunk room drops the jaws of the young. Two, two car heated garages flank both ends of the main house. Landscaping, mature gardens and gorgeous stonework throughout the property add to the magnificent setting. Beautifully maintained, this country estate is truly one of a kind.

Listed by Lisa Sullivan of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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

Price$3,500,000

Est. Mortgage: $/month

MLS Number 4700856

  • Residential Single Family
  • Listing Agent Name Kim Morgan-Wohler
  • Construction Existing
  • Bathroom 8
  • Bedrooms 5

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: 4.65% last updated on Sep 20, 2018
* 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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135 Paddock, Dorset, VT 05251

Price$2,995,000

Est. Mortgage: $/month

MLS Number 4674690

  • Residential Single Family
  • Listing Agent Name Elena Atwill
  • Bedrooms 6
  • Bathroom 10
  • Construction Existing

This extraordinary gated country estate is surrounded by Four Ponds and waterfalls with absolute privacy in an outstanding Dorset location. The stone, brick and timber exterior is complemented by expansive stone terraces and exquisite landscaping. Lavish interior design and amenities (elevator and communications) including the finest finishes and features with fully integrated technology. The acreage includes a 6 acre parcel permitted for use as a guest house or recreation pavilion. Completely rare in scale and detail framed by gardens, terraces and stonework, Four Ponds represents the epitome of country living.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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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415 Uphill Lane, Dorset, VT 05253

Price$2,950,000

Est. Mortgage: $/month

MLS Number 3058863

  • Residential Single Family
  • Listing Agent Name Elena Atwill
  • Construction Existing
  • Bathroom 8
  • Bedrooms 8

A simply outstanding opportunity, this private, 47 acre Country Estate with a 11,000 SF Colonial residence, a three-bedroom guest house, a four-car garage with caretaker's apartment, equipment barn, swimming pool and two build-able lots is now offered at less than 30% if its original construction cost. With expansive living spaces, a three-floor elevator, 9 fireplaces, a true cook's kitchen with hand painted cabinets and stone tops, a media room and library with custom butternut cabinetry, elegant bedroom suites and outdoor spaces that include a screened porch, stone terraces and covered porches that flank the view side, the additional amenities include a 2 bath pool house, large dog run, greenhouse, formal gardens, 2-story barn and a 3-car carport and generator room. Highlighted by exquisite landscaping in the heart of Southern Vermont, equidistant from NYC and Boston, Birchmeadow is perfect for use as a family compound or multi-generational gathering place.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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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190 Turkey Run Lane, Dorset, VT 05251

Price$2,500,000

Est. Mortgage: $/month

MLS Number 4508467

  • Residential Single Family
  • Listing Agent Name Elena Atwill
  • Construction Existing
  • Bathroom 7
  • Bedrooms 5

This stunning and exceptional 13 acre Dorset Hollow estate offers all the amenities of a magnificent and peaceful private retreat. Spectacular, sweeping and soaring views looking out to the pristine wooded mountain ranges and pastoral vistas define breathtaking. Designed to complement an active family, friends and entertaining this elegant 9 room residence has been masterfully crafted throughout for contemporary living, with seamless access to the spacious three season screened in porch and outdoor features including the 50' swimming pool and spa, outdoor shower, changing room, bocce court, pergola and extensive stone terraces set amid perennial gardens and naturalized landscaping. "Sleepy Hollow" is the separate and charming guest cottage with two bedrooms and baths plus full exercise room. This property encompasses the most desirable aspects of country living indoors and out.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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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237 Lily Pond Lane, Dorset, VT 05251

Price$2,350,000

Est. Mortgage: $/month

MLS Number 4648119

  • Residential Single Family
  • Listing Agent Name Laura Beckwith
  • Construction Existing
  • Bathroom 5
  • Bedrooms 5

Exquisite Dorset Hollow 100 acre Country Side Residence that inspires... the air breathes... the skies promise... the lush gardens protect or open for four season's pleasure... a sense of permanent presence through reclaimed architectural antiquities: hand selected native ash flooring... an 18th C. Belgium limestone mantel surrounds the oversized Count Rumford fireplace... Three Barn Frames & board unite... Slate Roofs... Period Greek stone tile floored entry & morning room! This 2005 collaborate effort of an artist and architect approached with the sense of Summer Greenery creating summer rooms under distinctive perspectives... while Winter opens to vast mountain views! The gourmet chef's kitchen offers custom cabinetry that sets the frame for AGA and Island cookery boasting easy clean up and appropriate storage. OPEN Living / Dining focus on amazing fireplace... a spiral staircase leads to the Primary Family suite boasts breathtaking mountain views... Separate guest wing of bedrooms...Private Office Grandeur... the baths plush in fine fixture & tile detail, steam shower & separate tubs. Lower level family, media and gym areas... oversized three bay attached barn ... raised bed vegetable gardens and utility barn. East and West screened summer rooms. Textured stone leading to ancient boards... each creative step opens to unmatched vistas over spring fed ponds and trails meandering. Geothermal efficiency for 5 plus bedrooms... Representing Dorset Hollow Life Perfection!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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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435 West Fields Road, Manchester, VT 05254

Price$2,325,000

Est. Mortgage: $/month

MLS Number 4715509

  • Residential Single Family
  • Listing Agent Name Laura Beckwith
  • Construction Existing
  • Bathroom 5
  • Bedrooms 4

Manchester Village perfection is obtained where nature's quietly sculpted 5 acre setting meets finely detailed custom design encouraging gatherings, yet preserving refined personal living! Dramatically poised on a promontory where a commanding view of Mount Equinox greets upon arrival. The backdrop frames a trout pond, circular drive and the Equinox Pond Trail system. Enter this sensational house from the welcoming front porch to the gracious 2+ story foyer capturing views through an expansive window wall beyond, absorbing the East Mountain Range. Immediate mountain views and light impacts the senses while "Old World" architectural detail are dramatic showcasing the staircase, balcony, deep moldings and doors disappearing into paneled walls. Flawless execution at every turn in the exceptional 32 X 26 living room with 12 foot coffer ceiling and great Count Rumford Fireplace. Passage wet bar leads to formal Dining while the cherry paneled study beckons an evening read. The sun filled cooks island kitchen walks onto terrace and is well lit from east & south... there's a breakfast area, window seating yet function as the pantry or laundry recede. A family room steps away boasts a window wall to the Equinox Mountain. The luxurious master offers built-ins and bath meeting every need and view! Three guest rooms are positioned for privacy. Still, a bonus room for hobby, lower level recreation space and workshop. There's a 2 car garage & 2 car detached barn. Exceptional!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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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67 High Meadow, Stratton Mountain Road, Winhall, VT 05340

MLS Number 4706503

  • Residential Single Family
  • Listing Agent Name Ellen Mallia
  • Construction Existing
  • Bathroom 5
  • Bedrooms 6

The first thing you notice at Cottage on the Green is the peaceful quiet of the surroundings and the incredible view of Stratton Mountain. Designed by noted Architect Jeffrey Barnes, the use of natural elements; wood, stone and brick seamlessly blends this home into the landscape. The interior envelops you with an elegant warmth, a retreat from the busyness of everyday life. Revel in the four-season splendor of sweeping views from every room. The quality of the craftsmanship is evident throughout the home. Designed for mingling, the masterly renovated cooks kitchen and dining room open onto a screened porch, a lovely space to enjoy summer mornings and cool evenings. Soaring stone fireplace in the vaulted living room warms you on cold winter nights. Designed to welcome guests, Jeffrey Barnes designed the family room and bedroom suites addition for all ages to relax, recreate and nod off after a busy day enjoying Vermonts many activities. Renovated in 2017, the master bedroom and bath is an elegant, peaceful respite from the days activities. Soak your cares away as you look onto the Mountain vistas. Cottage on the Green is a Stratton Mountain treasure.

Listed by Ellen Mallia of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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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2028 Lower Hollow Road, Dorset, VT 05251

Price$2,250,000

Est. Mortgage: $/month

MLS Number 4711444

  • Land
  • Listing Agent Name Andy Reed
  • Acreage 582.1
  • Zoning RR/ F1

Once in a lifetime opportunity to own over 500 acres of prime developmental, recreational or agricultural/ timberland in Dorset Hollow. Unbelievable views throughout the property. Property features brooks, pond trails, sugar maple potential and many possible house sites all with breathtaking views. Property is being managed with long term timber potential. Borders U.S. National Forest, conservation land and has its own gravel pit.

Listed by Andy Reed of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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 A VisitAsk A QuestionMore Details

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Copyright 2018 Northern 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. Subject to errors, omissions, prior sale, change or withdrawal without notice. This web site is updated daily.