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Bennington County 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 institutions such as Southern Vermont College and Bennington College. The largest towns in Bennington County are Bennington and Shaftsbury. Browse available Bennington County real estate below. 

Bennington County VT Homes for Sale

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Owl's Head Lane South Dorset VT 05251

Dorset, VTOwl's Head Lane South

Price$350,000

Est. Mortgage: $/month

MLS Number 4946394

  • Land
  • Acreage 12.4
  • Utilities None
  • Zoning ARR

Picture perfect 12.4 acre Dorset building lot tucked away at the end of a cul-de-sac is the perfect setting to build your next home. The large, level, and partially cleared lot offers a new owner open meadow, picturesque mountain views in two directions, accessed by private driveway with bridge over a babbling stream, and the possibility to create your own walking trails through the wooded portion. This lot is permitted for a 5 bedroom home with a mound septic design available. There are mountain views to the west of Mt. Equinox and mountain views east as well. The annual road maintenance costs approximately $700/yr for plowing and grading. Conveniently located between the center of Manchester and the Dorset town green.

Listed by Katherine Zilkha of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.73% last updated on Mar 16, 2023
* 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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47 Burnt Hill Road Winhall VT 05340

Winhall, VT47 Burnt Hill Road

Price$489,000

Est. Mortgage: $/month

Open House

MLS Number 4946319

  • Residential Single Family
  • Next Open House: Sat 03/25 11:00 am. to 1:00 pm.
  • Bedrooms 3
  • Square Feet 2,160
  • Bathroom 3

Nestled on 1.5 acres (+/-) of idyllic surroundings, this well-maintained 3-bedroom chalet is a true gem. Located in the exclusive Strattonwald community, it offers a private escape just minutes from the Stratton Mountain ski resort. The Strattonwald community features amenities such as a swimming pond, and access to tennis courts with the purchase of a $5000 bond, you'll also have access to a shuttle service to the resort. This is the perfect opportunity to own a beautiful property in a sought-after location with fantastic amenities. Don't miss out on the chance to make this incredible chalet your new home! Showings are delayed until 3/24/23.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.73% last updated on Mar 16, 2023
* 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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53 River Road Winhall VT 05340

Winhall, VT53 River Road

Price$529,000

Est. Mortgage: $/month

MLS Number 4946019

  • Land
  • Acreage 27
  • Zoning Residential

This is your opportunity to own a spectacular 27+/- acre property, only minutes from Stratton Resort. This parcel is primed for building - house site cleared, driveway in place, 3-bedroom septic installed, and underground power and high speed internet run. With this as your home base, adventure is as simple as stepping into the backyard and exploring the the walking trails, private pond, peaceful woods, tranquil brook, and sculpture gardens. High-efficiency modern cabin on site. Seller willing to remove cabin prior to sale. Seller is a licensed real estate agent.

Listed by Cheyanne Pugliese of Wohler Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.73% last updated on Mar 16, 2023
* 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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3155 VT Route 30 Dorset VT 05251

Dorset, VT3155 VT Route 30

Price$565,000

Est. Mortgage: $/month

MLS Number 4946003

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 2
  • Square Feet 1,920

Note:Deadline for offers is Monday, March 27, 2023 - 5 pm. Also please note that seller reserves the right ti accept any offer at any time and this does not guarantee that buyer will be able to submit an offer prior to seller acceptance of another offer. Rare Dorset Village offering in historic district. Residential or Commercial use. Large 1+ ACRE LOT accessed from Rt 30 with additional deeded ROW access from Meadow Lane. Two story frame building currently office space, previously residential duplex. Large level yard. Serviced by Town water, private on-site septic. Mountain. views, private, rural feel yet walking distance to local inns, theatre, shops, recreation. Property and first floor available for showing on short notice. 24 hr. advance notice required for showing second floor offices.

Listed by R. Diedrich August of RE/MAX Four Seasons

$
$
%
$/month over payments
Federal 30-year interest rate: 6.73% last updated on Mar 16, 2023
* 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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5420 Main Street Manchester VT 05255

Manchester, VT5420 Main Street

Price$599,000

Est. Mortgage: $/month

MLS Number 4945857

  • Multifamily
  • Units 3
  • Acreage 0.5
  • Square Feet 2,657
  • Utilities Cable - Available

Intact period details are the focus of this historic Italianate home centrally located in downtown Manchester. A wrap-around front porch that features chamfered columns with carved millwork brackets lends charm to this 1860s beauty. Inside, you'll find 2,657 square feet of living space with 3 units that could be restored to a single-family home. The front unit is a 2 bedroom duplex with a full bath. In the rear, there is an unfinished efficiency studio on the ground floor with a one-bedroom unit with a full bath above. Out back there is a barn with space for a workshop or home office. On the market for the first time in 50 years, this is a gem just waiting for the right steward.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.73% last updated on Mar 16, 2023
* 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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5420 Main Street Manchester VT 05255

Manchester, VT5420 Main Street

Price$599,000

Est. Mortgage: $/month

MLS Number 4945856

  • Residential Single Family
  • Bedrooms 2
  • Bathroom 2
  • Construction Existing
  • Square Feet 2,657

Intact period details are the focus of this historic Italianate home centrally located in downtown Manchester. A wrap-around front porch that features chamfered columns with carved millwork brackets lends charm to this 1860s beauty. Inside, you'll find 2,657 square feet of living space with 3 units that could be restored to a single-family home. The front unit is a 2 bedroom duplex with a full bath. In the rear, there is an unfinished efficiency studio on the ground floor with a one-bedroom unit with a full bath above. Out back there is a barn with space for a workshop or home office. On the market for the first time in 50 years, this is a gem just waiting for the right steward.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.73% last updated on Mar 16, 2023
* 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 4945895

  • Residential Single Family
  • Construction Existing
  • Bedrooms 6
  • Bathroom 7
  • Square Feet 6,500

This private setting on 40 acres is nothing short of EXTRAORDINARY! An iconic Stratton Mountain estate with a newly expanded and renovated grand lodge, a guest house - each with unrivaled views of the Stratton Mountain trails. The upscale addition & renovation of this Pearl Buck property is just minutes to the StrattonMountain 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 throughout 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: 6.73% last updated on Mar 16, 2023
* 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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3228 Route 30 Dorset VT 05251

Dorset, VT3228 Route 30

Price$1,500,000

Est. Mortgage: $/month

MLS Number 4945892

  • Residential Single Family
  • Bedrooms 5
  • Construction Existing
  • Square Feet 4,764
  • Bathroom 7

Dorset Village Traditional & a most Desirable Guest House that offers a very appealing open floor plan ideal for modern lifestyles boasting an expansive 40'X20' multi-use Great Room Kitchen that also opens onto a private marble, stone walled terrace. All 5 ensuite Bedrooms in the Main house offer fireplaces creating an incredibly inviting residence to entertain family and guests. There is an attached direct entry 2 car garage, a mudroom, while new pine floors flow throughout Great room, the Living room with Fireplace and additional Library with Fireplace. The Gracious Foyer offers architectural interest of a substantial staircase. Multiple options exist in choosing an owner's suite as all the bedrooms offer substantial comfort. A fantastic, village-wide coveted Guest House supports single floor living, one Bedroom, guest Loft, bath, Galley Kitchen and vaulted living area. This residence easily accommodates mixed use, office or rental. A handsome stone wall along the marble village sidewalks supporting strolls to the Dorset Inn, Barrows House, Dorset Union Store, Library, Dorset Bakery, Flowerbrook Pottery, Dorset Green, Dorset Field Club, Dorset Theater and the Dorset Historical Society. This is a very special location and parcel with a generous, yet manageable level tree-lined half acre. Southern exposure Side and Front Porches offer Views to the West where the Sunsets prove magical! There's 4764 SF of Living: Main house, 4044 SF & Guest House, 720 SF/deck, Dorset Landmark!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.73% last updated on Mar 16, 2023
* 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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Lot 6.1 Pearl Buck Drive Winhall VT 05340

Winhall, VTLot 6.1 Pearl Buck Drive

Price$275,000

Est. Mortgage: $/month

MLS Number 4945898

  • Land
  • Acreage 11.28
  • Utilities Cable - Available
  • Zoning Residential

Views Views Views- one of the last view lots available- 11.28 acres. Perched near the top of Pearl Buck Drive and capturing extraordinary southerly views from east to west and morning sun to sunset, this lot is begging for you to create that wow mountain residence that brings the awe inspiring setting and views of Stratton Mountain into the design! Stratton Mountain Base and Sun Bowl Lodges are just 7 minutes and you'll have an abundance of year round recreation and events at your doorstep. Purchaser shall be responsible for obtaining a state septic permit. Pearl Buck is a Town Maintained Road. Electric and cable at road.

Listed by Kim Morgan-Wohler of Wohler Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.73% last updated on Mar 16, 2023
* 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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Lot 7.3 &Lot 82 Sugarbush Extension Winhall VT 05340

MLS Number 4945896

  • Land
  • Acreage 11
  • Utilities Cable - Available
  • Zoning residential

Wonderful opportunity to create a private mountain escape! Stratton views are possible with clearing from this 11 acre parcel on the outer perimeter of the Forest Farms neighborhood adjacent to the Winhall Town Forest. You'll have the convenience of location, yet you'll be able to enjoy 11 acres of solitude and privacy from your homesite Purchaser will be responsible for obtaining a state wastewater permit. Sugarbush is a town maintained road.South Westerly exposure. The forest offers a mix of hardwoods along this moderate sloping parcel. You'll be at the Stratton Mountain Base Lodge in under 10 minutes and the Golf course is just 5 minutes away. Wow, you probably didn't know you could still have this much acreage so close to your favorite mountain resort! Create your perfect mountain house on a most desirable parcel!

Listed by Kim Morgan-Wohler of Wohler Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.73% last updated on Mar 16, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

Broker Reciprocity 

Copyright 2023 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. 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 March 24, 2023 2:53 AM EDT