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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384 Neilson Road Rupert VT 05768

Rupert, VT384 Neilson Road

Price$1,800,000

Est. Mortgage: $/month

MLS Number 4822061

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

Country charm and sophistication join hands in this special home perched high on a meadow in coveted Sykes Hollow-a perfectly tranquil setting. This home sits on 69 sub dividable acres with outstanding long range mountain views to the southwest. Equine friendly with a mix of flat pastures and woodlands. Tastefully appointed with plenty of natural light throughout. Amazing outdoor venue featuring a large covered porch and an adjacent stone patio. Entering this end-of-the-road- property one immediately gets a sense of peace and tranquility. Former horse stables converted into a 3 season guest house oozes with charm. Lots of trails for recreational use. Horses, ATV, Snowmobiling right out the door. 5 minutes to the Dorset Green. A very special offering. Simply sublime. Come take a look!

Listed by David Shehadi of Josiah Allen Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* 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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625 Sykes Hollow Road Rupert VT 05776

Rupert, VT625 Sykes Hollow Road

Price$1,300,000

Est. Mortgage: $/month

MLS Number 4816405

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 8
  • Bathroom 6

Situated just minutes from the Dorset Village Green along a quiet country road w/ fiber optic , this special offering features a beautifully renovated& expanded vintage residence, guesthouse, heated saltwater pool, barn with studio, situated with 122 acres of pasture and woodlands. The pastoral setting and charm of the residence cannot be overstated with a lovely stream, pond, beautiful stone walls and gardens. This unique property offers something for everyone throughout the year. Whether you seek a pasture for horses or mountainside recreation, the woodlands are ideal for hiking, mountain biking, snowshoeing, snowmobiling, hunting or tapping the maple trees. Well designed to work remotely with the full studio/guest suite above the barn. The beautifully expanded and updated 1778 main house has a breathtaking great room with wood burning fireplace, a formal dining room, a spacious open kitchen and a family room with second fireplace that opens to a screened porch and patio. Two masters en-suite and 3 additional bedrooms on the second floor provides ample room for friends and family. Enjoy a view of the pond, adjacent stream, heated saltwater pool and guest house from the screened in porch and patio. Your guests will never want to leave the 2 bedroom /2 bath guest house with living room and kitchen. The 3 car heated garage/barn includes a studio apartment with a large great room, kitchen & bath.The property exudes charm and peaceful country living yet convenience to Dorset.

Listed by Kim Morgan-Wohler and Trent Stephens of Wohler Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* 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$375,000

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: 2.72% last updated on Nov 25, 2020
* 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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3923 Kent Hollow Road Rupert VT 05776

Rupert, VT3923 Kent Hollow Road

Price$279,900

Est. Mortgage: $/month

Active With Contract

MLS Number 4835515

  • Land
  • County Bennington
  • Property Type Land
  • Acreage 31.5

Incredible surveyed 31.5 acre lot with long road frontage, beautiful open hidden fields protected by wood line perimeters would offer numerous options to build your new home or a perfect spot for a family retreat. An adorable A frame awaits the new buyer and has had recent renovations as late as 2011 and would be a perfect weekend get away or a place to stay while building your new dream home. The property also has a detached 2 car garage with additional attached room, offering a perfect conversion for your animals. The property is easy to walk, has a small pond, and beautiful mountain vistas grace the property. One of Vermont's prettiest spots and in a great recreational area as you will find the D & H bike trail in the center of Rupert and the Merck Forest hiking trails that are approximately 1.5 miles from this property. If you are looking for additional property, then the opportunity to buy an additional 191.5 across the street is possible. Let your dreams begin. Currently in land use but with the right offer seller would entertain removing. Property shares the water with the house across the street along with power but can easily be deeded or changed.

Listed by Hughes Group Team of Casella Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* 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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3923 Kent Hollow Road Rupert VT 05776

Rupert, VT3923 Kent Hollow Road

Price$279,900

Est. Mortgage: $/month

Active With Contract

MLS Number 4835486

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

Incredible surveyed 31.5 acre lot with long road frontage, beautiful open hidden fields protected by wood line perimeters would offer numerous options to build your new home or a perfect spot for a family retreat. An adorable A frame awaits the new buyer and has had recent renovations as late as 2011 and would be a perfect weekend get away or a place to stay while building your new dream home. The property also has a detached 2 car garage with additional attached room, offering a perfect conversion for your animals. The property is easy to walk, has a small pond, and beautiful mountain vistas grace the property. One of Vermont's prettiest spots and in a great recreational area as you will find the D & H bike trail in the center of Rupert and the Merck Forest hiking trails that are approximately 1.5 miles from this property. If you are looking for additional property, then the opportunity to buy an additional 191.5 across the street is possible. Let your dreams begin. Currently in land use but with the right offer seller would entertain removing. Property shares the water with the house across the street along with power but can easily be deeded or changed.

Listed by Hughes Group Team of Casella Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* 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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89 Main Street Rupert VT 05768

Rupert, VT89 Main Street

Price$279,000

Est. Mortgage: $/month

MLS Number 4719939

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 5
  • Bathroom 2

Great opportunity! Village commercial historic 1850 Colonial. Four barns, spring fed pond, equestrian ready with all sorts of options and possibilities. Five bedroom/2 baths this charming property is located on Main St in the center of this quintessential New England village. Come be part of the Rupert Renaissance! Plenty of space for animals, gardens and farming,stalls,workshops, gym,etc. All flat meadow terrain with curb cuts on both routes 315 and 153. 10 minutes to Dorset Green and 20 minutes to Manchester. Adjacent Antique Center ( 115 Main Street) also available - both properties included for $450,000. Endless Possibilities !

Listed by David Shehadi of Josiah Allen Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* 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

682 VT 30 Route Rupert VT 05768

Rupert, VT682 VT 30 Route

Price$225,000

Est. Mortgage: $/month

MLS Number 4839141

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 4
  • Bathroom 2

A 4 bedroom, 1.5 bath c.1900 Post Beam cape located in Rupert, Vermont. A large covered back porch overlooks the beautiful level 1.10 +/- acre tree lined lot where sounds of the Hager Brook can be enjoyed. The charming 19' beamed living room features a wood stove, bringing ambiance and warmth into the room. The 17' country eat in kitchen has a great south facing window and opens into the walk in pantry. The convenient first floor master bedroom is 12'x23' and sports a half bath. A new stainless steel liner installed in chimney 2011. A great back yard with plenty of room for gardening, pets, children's play, barbecuing or just relaxing. Small garage or large storage shed.

Listed by Lori Winn of New England Lakeside Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* 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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Pawlet Mountian Road Rupert VT 05776

Rupert, VTPawlet Mountian Road

Price$119,900

Est. Mortgage: $/month

MLS Number 4828972

  • Land
  • County Bennington
  • Property Type Land
  • Acreage 5

Listed by Nancy Liberatore of Lakes & Homes Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* 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

kent hollow Road Rupert VT 05776

Rupert, VTkent hollow Road

Price$24,500

Est. Mortgage: $/month

MLS Number 4815540

  • Land
  • County Bennington
  • Property Type Land
  • Acreage 10

Affordable 10A wooded parcel with babbling stream. Great for recreation, camping, hunting.. just up the road from trail head to Merck Forest (over 3000 acres of protected land open to public for hunting, hiking, cross country skiing). Possible potential to get seasonal camp permit (cabin with no interior plumbing). There is a section in the front along the road that is gently sloping/cleared - otherwise front of land is steep/difficult to access top/back portion other than hiking back. Beautiful quiet setting along town maintained back country gravel road.

Listed by Scott Mcchesney of McChesney RE, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* 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

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Copyright 2020 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 November 30, 2020.