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 802-793-2002 or contact us online.

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100 Holly's Way Rupert VT 05768

Rupert, VT100 Holly's Way

Price$549,000

Est. Mortgage: $/month

MLS Number 5015307

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

Long driveway to a Private setting with lots of room to hike, hunt or just enjoy the peace and quite. Possible subdivision. House is warm and cozy with a large sleeping loft on the second loft. There is a foundation in place for an out building.

Listed by Charles Mauro of Josiah Allen Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* 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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259 Watrous Road Rupert VT 05776

Rupert, VT259 Watrous Road

Price$375,000

Est. Mortgage: $/month

Active With Contract

MLS Number 5019110

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

Mountain views and meadows surround this lovely cape on 2.30 acres just 6 miles from the Dorset Green. Well built two bedroom, two bath light filled home offers hardwood floors and updated kitchen with brand new stainless steel appliances. The oversized picture windows enhance the spectacular mountain views. The dining room features a gas stove or enjoying a cozy wood burning fire in the living room fireplace. Updated electrical with 200 amps and whole house generator. The attached one-car garage with new concrete floor features direct entry to the home. Don't miss the standing seam roof, 3rd gen Starlink internet, drilled well and newly graded driveway. This home is ready for you! Once a three-bedroom home and could be again. Enjoy peace of mind with this updated home. Being sold furnished. Schedule a tour today!

Listed by Margretta Fischer of Wohler Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* 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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1000 Bear Mountain Camp Road Rupert VT 05776
Active With Contract

MLS Number 5016966

  • Land
  • County Bennington
  • Square Feet 5,880,600
  • Acreage 135

An amazing get-away in the hills of the southern VT town of Rupert, these 135 +/- acres offer amazing mountain views, open fields, apple trees & a mature forest! Located at the end of a private, seasonal shared road, the property offers an ideal vacation getaway, hunting paradise or potential homesteader property with 2 +/- acres of open fields, 23 apple trees, 2 streams & a unique off-grid cabin with small ponds nearby. Ready for your finishing touches, the cabin offers a newer roof, windows, kitchen, tongue & groove pine interior, hot water sink & shower, stabilized footings & an addition! A new circuit breaker with 30-amp service has been installed for use with a portable generator. Gated access, posted & well-marked with blazes & pins, so you'll know exactly what you own. An excellent woods road through the property makes ATV & foot access easy. An excellent hunting property with food plots ready to be reclaimed, 4 older tree stands on the property & shooting lanes. VAST snowmobile trail access just off the property to the east. Serviced by water brought in for the shower & sink. Heated by a woodstove with wood from the property. A large woodshed has been framed out and is designed to support six solar panels. Satellite TV & internet with the home setup for a portable generator. Fantastic views of the near & far mountains to the north & west. Just north of Manchester, VT with great shopping, fine dining & skiing.

Listed by Curtis Trousdale and Michael Wrobel of Preferred Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* 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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1000 Bear Mountain Camp Road Rupert VT 05776
Active With Contract

MLS Number 5018628

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 2
  • Square Feet 928

An amazing get-away in the hills of the southern VT town of Rupert, these 135 +/- acres offer amazing mountain views, open fields, apple trees & a mature forest! Located at the end of a private, seasonal shared road, the property offers an ideal vacation getaway, hunting paradise or potential homesteader property with 2 +/- acres of open fields, 23 apple trees, 2 streams & a unique off-grid cabin with small ponds nearby. Ready for your finishing touches, the cabin offers a newer roof, windows, kitchen, tongue & groove pine interior, hot water sink & shower, stabilized footings & an addition! A new circuit breaker with 30-amp service has been installed for use with a portable generator. Gated access, posted & well-marked with blazes& pins, so you'll know exactly what you own. An excellent woods road through the property makes ATV & foot access easy. An excellent hunting property with food plots ready to be reclaimed, 4 older tree stands on the property & shooting lanes. VAST snowmobile trail access just off the property to the east. Serviced by water brought in for the shower & sink. Heated by a woodstove with wood from the property. A large woodshed has been framed out and is designed to support six solar panels. Satellite TV & internet with the home setup for a portable generator. Fantastic views of the near & far mountains to the north & west. Just north of Manchester, VT with great shopping, fine dining & skiing.

Listed by Curtis Trousdale and Michael Wrobel of Preferred Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* 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 Lewis Road Rupert VT 05776

Rupert, VT47 Lewis Road

Price$249,500

Est. Mortgage: $/month

MLS Number 5025821

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

Nestled along a quiet, lightly traveled town-maintained gravel road, this c1850 colonial sits on 6 plus acres of serene land, enjoying protected land and no nearby neighbors. The property includes two prime, tillable meadows ideal for animals, plus a three-car detached garage that's perfect for use as a workshop during the restoration. The house boasts an impressive hand-hewn timber frame and many original details, including wide plank flooring, moldings, doors, and hardware. Updates include some rewiring and oil hot air heat. The home has an older septic system and a spring water supply. This property is priced for those ready to embrace a renovation project, offering strong bones, a prime location, beautiful setting, and quality acreage. Conveniently located just 15 minutes from the Dorset/Manchester area, it's also served by Mettawee School for pre-k through 6th grade, school choice for grades 7-12, and fiber optic internet access.

Listed by Scott Mcchesney and Robin Chesnut-Tangerman of McChesney RE,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* 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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61 East Street Rupert VT 05776

Rupert, VT61 East Street

Price$210,000

Est. Mortgage: $/month

Active With Contract

MLS Number 5013456

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 2

Nestled in the Vermont village of Rupert this 3 bedroom, 2 bath home has all you need. Modular construction with large family room with pellet stove, large kitchen with island, dining room, living room, primary bedroom suite and more. Private back yard, front sitting porch and large unfinished basement. The attic space is insulated with a walk up and materials are left to begin finishing it if desired.

Listed by Max Squiers of KW Vermont - Brenda Jones Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* 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

27 Sandgate Road Rupert VT 05776

Rupert, VT27 Sandgate Road

Price$159,000

Est. Mortgage: $/month

MLS Number 5008100

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 2
  • Acreage 1.8

Nature and Privacy! Great opportunity is ready for you! A small house/camp hidden away on a town maintained road surrounded by green mountains and a little brook flows in a creek. The Sandgate Brook flows on the others side of the road offering trout fishing or swimming. There is a nice mix of open meadow and woods with trails on 1.80 acres. The mostly level lot has so much to offer. A two bedroom existing septic and dug well is ready for you to fix up the existing building or building a new home. The back of the lot offers trails and woods while the front of the lot is cleared. The existing building needs all new interior work, but ready for you to make your home. come have a look at this property and see the potential.

Listed by Margretta Fischer of Wohler Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* 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 2025 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 January 21, 2025 6:07 AM EST