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

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

{$office->Name}

Burlington Office
1 Steele Street
Suite 111
Burlington VT, 05401
Office: 802-318-0833

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.62% last updated on Jun 14, 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

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

{$office->Name}

Burlington Office
1 Steele Street
Suite 111
Burlington VT, 05401
Office: 802-318-0833

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.62% last updated on Jun 14, 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

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

{$office->Name}

Burlington Office
1 Steele Street
Suite 111
Burlington VT, 05401
Office: 802-318-0833

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.62% last updated on Jun 14, 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

415 Uphill Lane, Dorset, VT 05253

Price$2,950,000

Est. Mortgage: $/month

MLS Number 3058863

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

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

{$office->Name}

Burlington Office
1 Steele Street
Suite 111
Burlington VT, 05401
Office: 802-318-0833

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.62% last updated on Jun 14, 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

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

{$office->Name}

Burlington Office
1 Steele Street
Suite 111
Burlington VT, 05401
Office: 802-318-0833

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.62% last updated on Jun 14, 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

674 Dorset Hollow Road, Dorset, VT 05251

Price$2,450,000

Est. Mortgage: $/month

Pending

MLS Number 4690538

  • Residential Single Family
  • Listing Agent Name Laura Beckwith
  • Construction Existing
  • Bathroom 6
  • Bedrooms 5

Unparalleled Dorset Hollow residence, setting & location on estate lands consisting of 43 "near village" acres! Frontage on the Mettowee River stretches over 1200 feet...walk to village location endorses outdoor living; biking, hikes, snowshoeing, cross country skiing, swimming and fishing right from the doorstep! Suitable for equine or agricultural interests drawing from open meadow, stream-side paths or wooded trails accessible to the Dorset Pinnacle or the Dorset Hollow Loop! This graciously scaled residence of understated appeal is totally renovated to an undeniable level of architectural detail and infra-structure. Inviting, the house and marble cottage will have family and friends begging to return. The slate roofed 4 bedroom traditional New England Residence captivates with exterior marble facade accents which are carried through the terrace and walls stepping up to the discrete heated Gunite pool. Enter the welcoming foyer where warmth greets: Vaulted informal living features cherry paneling, a lovely centered fireplace and deep sill windows to either side, center living room extends to music room boasting a second fireplace. The formal dining room connects the butlers pantry to sunlit cooks expansive 'state of the art' kitchen-dining overlooking the river! The primary suite provides soothing river song that enjoys the view to the pool, sweeping meadow and mountains. There are 3 en-suite guest bedrooms. Add a gym/studio. Every detail ensures complete Vermont Comfort!

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

{$office->Name}

Burlington Office
1 Steele Street
Suite 111
Burlington VT, 05401
Office: 802-318-0833

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.62% last updated on Jun 14, 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

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.

{$office->Name}

Burlington Office
1 Steele Street
Suite 111
Burlington VT, 05401
Office: 802-318-0833

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.62% last updated on Jun 14, 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

67 High Meadow, Winhall, VT 05340

Price$2,225,000

Est. Mortgage: $/month

MLS Number 4467387

  • Residential Single Family
  • Listing Agent Name Stephen Coombs
  • Bedrooms 6
  • Bathroom 5
  • Construction Existing

The High Meadow Road/Stone House Road neighborhood has some of Strattons finest homes taking advantage of rare Golf Course frontage on the Forest 8 fairway and stunning Stratton views. This luxurious home, designed by noted Vermont architect Jeffery Barnes was built using a large amount of Vermont stone, brick and cedar shingles. Just completed in 2017 is a stunning master bath/bedroom/sitting area and kitchen remodel by a noted Vermont designers ID3 and Wadsworth builders. The serenely landscaped courtyard was completely redone in 2017. From the brick floored entry you see cathedral ceilings with vintage barn beam detailing, warm wood floors, and a multitude of custom windows showcasing the Stratton Mountain and Stratton Golf course Views. Now offered completely furnished (excluding the owners personal effects and the floral painting in the living room, the game table in the media room and the 10 dog figurines on the mantle), turn key for winter 2017 occupancy!

Listed by Stephen Coombs of Stratton Real Estate

{$office->Name}

Burlington Office
1 Steele Street
Suite 111
Burlington VT, 05401
Office: 802-318-0833

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.62% last updated on Jun 14, 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

704 Stonehouse, Winhall, VT 05340

Price$2,200,000

Est. Mortgage: $/month

MLS Number 4673765

  • Residential Single Family
  • Listing Agent Name Ron Marcellus
  • Bedrooms 5
  • Bathroom 7
  • Construction New Construction

Premier unique Country home on Golf Course with southeast exposure and VIEWS- of golf course ,Stratton Mountain and Stratton Lake- snowshoe,bobsled , golf out your backyard. Designed by well known RI architect- Views from dining,living,master bedroom,guest bedrooms and family room- high quality detail throughout this home and impeccabbly landscaped

Listed by Ron Marcellus of Tamarack Realty

{$office->Name}

Burlington Office
1 Steele Street
Suite 111
Burlington VT, 05401
Office: 802-318-0833

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.62% last updated on Jun 14, 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

50 Quarter Mile Road, Winhall, VT 05340

Price$2,200,000

Est. Mortgage: $/month

MLS Number 4664083

  • Residential Single Family
  • Listing Agent Name Christiane Carroccio
  • Bedrooms 4
  • Bathroom 5
  • Construction Existing

Located in one of Stratton's nicest neighborhoods, this meticulously crafted four bedroom home will thrill the most discerning buyer. Mountain contemporary with European charm, this home was rebuilt with incredible detail and finished in 2014. Giant wood beams, reclaimed lumber, and wood slabs are juxtaposed with modern elements for minimalist appeal. Poggenpohl cabinet system with Subzero fridge, Franke sink and hood, Gaggeneu steam oven, Miele coffee station, and more will please the chef in your life, or make you into one! Perks like an indoor Miele grill on stone slab and warming drawers take mountain living to a new level. Bathrooms are designed with natural light, glass subway tile, and custom sinks. Bar cellar with Poggenpohl lighting shelves is a cozy retreat. Radiant floor heat throughout the home, with backup radiator system. Stone patio and landscaping are designed for summer enjoyment while minimizing maintenance. A home with wellness in mind; giant sauna, fitness room, spa-style bathroom with oversized steam shower, and an overall sense of impeccably planned design features. Come discover this amazing escape, in the heart of Stratton!

Listed by Christiane Carroccio of TPW Real Estate

{$office->Name}

Burlington Office
1 Steele Street
Suite 111
Burlington VT, 05401
Office: 802-318-0833

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.62% last updated on Jun 14, 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

Broker Reciprocity

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.