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Rupert Vermont Real Estate

Bennington County
Chartered: August 20, 1761
Area: 28,659 Acres = 44.78 Square Miles
Population (US Census, 2000): 704
Population Density (persons per square mile): 15.7

Rupert Vermont is on the western side of Vermont, next to the New York border. It is just northwest of Manchester, Vermont, west of Dorset, Vermont, and south of Pawlet, Vermont. This small, quiet Vermont town features real estate of all types, including primary residences, vacation homes, and retirement homes. Just a short drive away one can be shopping in Manchester’s famous designer outlets or enjoying a play at the Dorset Playhouse. Rupert Vermont real estate is under an hour away from some of Vermont’s most popular ski resorts, including Stratton Mountain Ski Resort, Magic Mountain Ski Resort, and Bromley Mountain Ski Resort.

864 Rogers Road Rupert VT 05251

Price$3,600,000

Est. Mortgage: $/month

MLS Number 4496096

  • Residential Single Family
  • Construction Existing
  • Bathroom 6
  • Bedrooms 4
  • Square Feet 6,837

Magnificent Country Estate property with privacy and views. Perfectly sited close to the town of Dorset and at the end of a town maintained road to capture views of the Mettowee Valley and Green Mountain National Forest. Many well maintained trails traverse the 642 acres going up to Spruce Peak. A two acre pond is surrounded by pristine fenced pasturelands. Beautifully landscaped gardens, attached barn, outdoor fireplace and covered porch are just some of the features offered. Property also has separate guest house and caretaker quarters. Property is managed for high quality timber production with a current Standing timber value at 1.2M.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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

Price$2,400,000

Est. Mortgage: $/month

MLS Number 4764906

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 2,988

This is the quintessential Vermont horse property located minutes from the Dorset green. The farm has it all: 33 acres of lush pastures, a swimming pond, brook and woodlands that run up to the edge of the property. Fantastic views of nearby mountains and Sykes Hollow. A classic horse barn with groom's apartment, 7 stalls, wash stall with heat lamps, heated tack room with washer and dryer in the grain room/work area. The hayloft has ample space for full loads of hay and shavings. Numerous sheds and outbuildings and a 2012 70 x 144 heated indoor riding arena with travel right footing. 100 x 200 outdoor ring with travel right footing. Derby field with ditch and bank. There are 2 over sized turn out fields, 2 large turn out fields... all with dry paddocks and run in sheds. 3 additional large turn out fields and 3 sand paddocks. The main 4 bedroom farmhouse was completely renovated in 2011. In addition to the main house there is a charming attached 2 bedroom guest house, which currently provides rental income. Sykes Hollow Road is right off of route 30 for easy access to Dorset, Manchester and Saratoga and all they have to offer. If you want to own and enjoy a classic Vermont horse farm property on 33 acres, this is one you need to see. Shown by appointment only. All measurements are approximate.

Listed by Tatsiana Clark of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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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864 Rogers Road Rupert VT 05251

Price$2,400,000

Est. Mortgage: $/month

MLS Number 4771007

  • Residential Single Family
  • Construction Existing
  • Bathroom 6
  • Bedrooms 4
  • Square Feet 6,837

Magnificent Country Estate property with privacy and views. Perfectly sited close to the town of Dorset and at the end of a town maintained road to capture views of the Mettowee Valley and Green Mountain National Forest. Many well maintained trails traverse the 50 acres going up to Spruce Peak. A two acre pond is surrounded by pristine fenced pasturelands. Beautifully landscaped gardens, attached barn, outdoor fireplace and covered porch are just some of the features offered. Property is managed for high quality timber production with a current standing timber value roughly at 1.2M. Also being offered with 642 acres and guest house.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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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334 Dole Road Rupert VT 05776

Price$1,295,000

Est. Mortgage: $/month

MLS Number 4336932

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 3,300

Mountain View Farm is a horseman's paradise. Panoramic far reaching views. Center chimney reproduction saltbox home with tunnels to the four plus garage garage barn and greenhouse. Brand new five stall horse barn with tack room that could easily be expanded to ten stalls. Two ten acre corrals with heated water troughs overlooks swimmimg pond. Restored cape cod caretaker's or guest home with 5 fireplaces, second pond, mature fruit trees all bordering lands of Merck Forest. Fantastic breathtaking property, a must see! Internet is available through Consolidated Communications. The owner would consider dividing the properties.

Listed by Willard Watson of Josiah Allen Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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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926 Hebron Road Rupert VT 05768

Price$995,000

Est. Mortgage: $/month

MLS Number 4754368

  • Residential Single Family
  • Construction Existing
  • Bathroom 6
  • Bedrooms 5
  • Square Feet 4,950

Within 15 minutes of Dorset, Stone Ridge Farm offers complete privacy and commanding views of the Taconic Mountains. The owners, purveyors of fine Scandinavian antiques, built the 4,950-square-foot residence in 2001 at the end of a ½-mile drive. The home is a New England farmhouse with a distinct Scandinavian influence, which reflects the timeless lineage of two cultures with its high craftsmanship and attention to detail. The interior design includes antique pickled pine floors, built in antique Scandinavian wall cabinets and four fireplaces. The Great Room with its gourmet kitchen, informal dining and sitting area is cozy with its defining Norwegian woodstove, and spacious with its 14-foot ceilings and endless views to the South and East. The living spaces are light filled and flexible in use. There are four en suite bedrooms with a master bedroom and generous 1st floor guest suite. A 2-story barn and 4-bay equipment shed complete the farmstead. Threaded through the 130 acres of meadows, ponds, orchards and woodlands are miles of trails to snow shoe, x/c ski, hike, bike or ride horses. The 40 mile D & H rail trail is close by, providing additional trails to enjoy. 16 miles from Manchester's fine dining and shopping, 22 miles to Bromley and 34 miles to Stratton.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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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63 Sykes Hollow Road Rupert VT 05776

Price$825,000

Est. Mortgage: $/month

MLS Number 4703350

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 3
  • Square Feet 4,464

Sykes Hollow Contemporary residence that has been custom designed and masterfully crafted for todays open concept living. The twelve acre site takes advantage of the distant mountain and meadow views as seen from a traditional wrap around deck which leads to the light filled living room with a cozy corner fireplace. The kitchen and adjoining pantry/wet bar is a cook's dream with high end appliances, granite counter tops, custom cabinetry and a breakfast nook. A spacious master bedroom takes advantage of the views from banks of windows and features an adjoining luxurious bath and over sized walk in closet. Two guest rooms and another bath complete the second story. A lower level has potential for a media or family room. This property is minutes from Dorset and is located 4 miles north of the Dorset Village Green in the picturesque Mettowee Valley.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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

195 Derby Hill Road Rupert VT 05768

Price$640,000

Est. Mortgage: $/month

MLS Number 4732648

  • Residential Single Family
  • Construction Existing
  • Bathroom 9
  • Bedrooms 7
  • Square Feet 5,541

A truly special property with loads of room including the 3700 square foot main house with 5 bedrooms, 1800 square foot 2 bedroom guest cottage, 1700 square foot party barn, two detached garages, additional outbuildings, flowing multi-level deck with long views down the valley, leading to the in-ground pool. Numerous features including wide pine floors, natural woodwork, spa-like bathrooms, sauna, radiant heat, multiple fireplaces and more. Must be seen to be appreciated, the possibilities are endless.

Listed by David Citron and Julie Citron of RE/MAX Four Seasons

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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

14 Sykes Hollow Road Rupert VT 05768

Price$535,000

Est. Mortgage: $/month

MLS Number 4751932

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 1,845

A Small Slice of Heaven. This property offers the best of both worlds; the style & charm of a vintage 1790's Vermont Farmhouse, but completely renovated and updated from the foundation up. Located on sought after Sykes Hollow road this home sits on three flat usable acres, and is surrounded by 25 acres of farm fields in Vermont Land Trust, giving the property a the sense of open space and Mountain views in several directions. Sit on your deck and enjoy the sunsets, or tend to your garden. This home offers many fine features including: 3 bedrooms and two new full baths, renovated granite kitchen with custom cabinets, center island, new chrome appliances, and deep country soapstone sink. The floors are a combination of hardwoods, softwood, and ceramic tile. The great room provides a perfect place for everyone to relax, and a foundation base has been added during construction should a buyer want to add a wood burning fireplace to this room. The mudroom/entry has an attractive old brick floor laid in a vertical pattern. The heating system is baseboard hot water on the main floor and second floor, and the basement level has radiant heat in the floor should further expansion space be desired. The second floor has one bedroom and a full bath, and there is attic storage, or room for a new master bedroom suite to be added. There are some truly breath taking views from this property looking both south down the Mettowee Valley and north toward a neighboring fenced horse pastures.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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

57 Ike Wright Road Trail Rupert VT 05768

Price$495,000

Est. Mortgage: $/month

MLS Number 4763750

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 1,800

Built in 2005 with large addition added in 2017 this home in the country is picturesque! This 162 acre property features meadows, a pond, indian river, rail trail access and woods abundant in wildlife. Views of Mt. Antone from the master bedroom and side porch! Living room with cathedral ceiling, granite counter tops, custom tile master bath! This cozy home is close to Manchester and a short drive to Stratton, Bromley and Magic Mountain! A true Vermont paradise for nature lovers or those looking for peace and serenity!

Listed by Jason Saphire of www.EntryOnly.com

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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

251 Youlin Rd Rupert VT 05776

Price$399,000

Est. Mortgage: $/month

MLS Number 4620565

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 3
  • Square Feet 3,033

Total privacy set back amidst 60 acres of woods and gorgeous rolling meadowland is this 3+ bedroom, 3.5 bath beautifully built and maintained home. The setting is incredible with a brook, pond and 25 acres of open meadowland (great for horses, etc.) The home takes full advantage of the setting with distant views overlooking the property. Great living space with open kitchen and dining area boasting french doors to the deck with awning that overlooks the pond. The living room has lots of glass, soaring cathedral ceiling and massive stone fireplace. Other amenities include 1st floor master suite, 28x28 attached, heated garage, laundry/mud room with tile floor, skylights and detached tractor/garden shed. Great location - less than 10 minutes to Dorset and a truly special Vermont setting. A great location - less than 10 minutes to Dorset and a truly special Vermont setting.

Listed by Scott Mcchesney of Lee D. McChesney RE, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Aug 15, 2019
* 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 2019 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 20, 2019.