Rupert Real Estate

Situated on the border of New York and Vermont is the town of Rupert, Vermont. Rupert is set in a beautiful rural setting. Rupert has a rich history you can see exemplified in its historic New England homes. Explore current real estate for sale in Rupert, Vermont. If you have any questions or if you'd like to see any of these properties in person, call 802-760-3100 or contact us online.

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369 Sykes Hollow Road Rupert VT 05761

Rupert, VT369 Sykes Hollow Road

Price$2,000,000

Est. Mortgage: $/month

MLS Number 4841751

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 4
  • Bathroom 3

Situated in Southern Vermont's Mettowee Valley; minutes from Dorset/Manchester and close proximity to Albany, Saratoga, and Saugerties, you can't help but recognize the magical, calm feeling as you approach Sykes Hollow Farm. Upon turning up the tree lined drive, passing three grass paddocks, large fields with Run-In Sheds, Derby Field and a competition sized outdoor Ring (100 x 200) the charming reimagined (2011) farmhouse awaits your arrival. Consisting of four bedrooms and three baths, and a wonderful open country kitchen where there is room for guests to help with dinner preparations before adjourning to the wood beamed, candle lit dining room. After dinner you can curl up with a good book or board game in front of a roaring fire in the cozy living room. This home also enjoys a running brook, swimming and skating pond, seven stall show barn and 70 x 144 indoor ring. Add a two-bedroom guest cottage for family or guests plus a barn with a studio/groom apartment as well as space for yoga, dance or exercise in loft area. This 33-acre gem awaits the buyer who is looking to embrace all a Southern Vermont lifestyle has to offer, including golf, hiking, snow shoeing, skiing and the opportunity to make lifelong friends and memories. All measurements approximate.

Listed by Richard Slocum of Four Seasons Sotheby's Int'l Realty

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$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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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Foote Road Rupert VT 05768

Rupert, VTFoote Road

Price$350,000

Est. Mortgage: $/month

MLS Number 4693545

  • Land
  • County Bennington
  • Property Type Land
  • Acreage 17

Last available lot of four lot subdivision. Upscale, rural, private, quiet, mountain views. Foote Road. is quiet byway off Dorset West Road. Rare opportunity for privately situated residence with views and easy access to quality schools, historic village, golf, skiing,, fishing, hunting, biking, hiking shopping, cultural attractions.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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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557 Route 153 Rupert VT 05776

Rupert, VT557 Route 153

Price$140,000

Est. Mortgage: $/month

MLS Number 4867472

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 1

Sweet c.1890's farmhouse surrounded by farmland in West Rupert, Vermont. Large, level yard perfect for gardening or just enjoy the gorgeous Vermont summer weather under one of the big ole' shade trees. Three bay barn/carport provides ample storage for vehicles and equipment as well as an attached shed just off the kitchen. Generously sized living room just a step off the front covered porch. Formal dining room, full bathroom, kitchen and office round out the first floor. Second floor offers three bedrooms. Some tlc would be necessary. The farmhouse is just around the corner from the West Rupert-Pawlet Rail Trail and the Village. So sweet.

Listed by Faith Rhodes and Melissa Genovart of Rhodes Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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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Vermont Route 315 Rupert VT 05768

Rupert, VTVermont Route 315

Price$45,000

Est. Mortgage: $/month

MLS Number 4867138

  • Land
  • County Bennington
  • Acreage 4.4

Quiet beautiful 4.4 acre parcel straddles babbling Mill Brook located close to Rupert Village approximately 1 acre cleared. Electricity available at the road. Minutes from Merck Forest and Farm Land Center with over 3,000 acres of protected land open to public for the classic Vermont outdoor activities. Located 35 minutes to Saratoga Springs, NY and just 20 minutes to Dorset/Manchester area. Enjoy the serenity of the Green Mountains with all the conveniences near by.

Listed by Elizabeth Romano of Josiah Allen Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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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Sandgate Road Rupert VT 05776

Rupert, VTSandgate Road

Price$24,999

Est. Mortgage: $/month

MLS Number 4858727

  • Land
  • County Bennington
  • Property Type Land
  • Acreage 1.3

Vermont Brookside Retreat A special opportunity - this beautiful Brookside meadow with great frontage along White Creek, easy access off a back town gravel road and Power at hand. The Parcel is fully in the river corridor and partially in the Zone A flood zone limiting it to agricultural/recreational use and allowing for the possibility of having a site for a seasonal RV camper. A very special setting and an affordable way to have that special piece of Vermont and your getaway retreat with fishing out your back door! Located just 20 minutes to Manchester/Dorset areas and just over 1/2 hour to Saratoga Springs, NY.

Listed by Scott Mcchesney of McChesney RE,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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 TourAsk A QuestionMore Details

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Copyright 2021 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 September 28, 2021.