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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999 Route 30 Rupert VT 05761

Rupert, VT999 Route 30

Price$3,995,000

Est. Mortgage: $/month

MLS Number 4904677

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 5
  • Bathroom 7

Hagarbook Farm completely restored 5034 SF C. 1767 Residence consisting of magnificent Mettowee River frontage interior to the 320 acres, Hagar Brook and Waterfall, Harmons Mint Historic Site, Pond, Agricultural Fields, Extensive Trail System and View Sites galore! The Land Straddles both East Rupert and Dorset. Add significant buildings in lovely condition: 750 SF Guest House, Barn 37 X 100, Tractor Barn 26 X 50, Horse Barn 50 X 28 and additional out buildings--24 X 18, 20 X 14, 20 X 12, 16 X 12, 40 X 24! An exemplary eighteenth century compound approximately 3 miles north of the Dorset Green. The Great-Room Kitchen with exposed post and beam framing is the welcoming hearth of the home which walks out to the wrap around porch or sun room to the west where the living extends upon a wonderful level stone walled terrace overlooking the grounds and river beyond. Crisp architectural details witnessed in every room; Dining, Living, Family, Office and 4 Wonderful Bedrooms up. There are 5 baths, 2 half baths and a guest house ... Whether it's agricultural or equine interest, stream & field, auto collector, historical appreciation or family gathering ideals, this property is a treasure. Vermont Current Use real estate tax benefits for the next steward to embrace. 320 acres in the prized Mettowee Valley nearby Dorset!!!

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

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$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* 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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166 McKeighan Road Rupert VT 05776

Rupert, VT166 McKeighan Road

Price$2,500,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4900123

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 4
  • Bathroom 5

An estate for the most discerning of buyers. Have you been looking for an estate that combines exquisite details, views, and options for unlimited uses along with privacy? Need a gentlemen's farm for your pleasure horses? An estate suitable for an established events person? If so, this property is for you! 267.5 acres of rolling hills. Here you will find a custom built owner's residence which combines the moving of two barns which were rebuilt into one post and beam, owners residence. The detailing is second to none. A few steps from this home is the most amazing of pool houses which has every upgrade imaginable and allows for swimming 365 days/year, in all weather. There are four independent living accommodations along with a tractor barn, 6 bay animal pen, an animal holding barn with a separate veterinary room with heat and water, and walk in cooler. All electrical is underground. There are four ponds. No chemicals have been used anywhere on this land for the past 17 years so organic certification is possible. This is the estate to be at if another pandemic hits. This property is perfect for destination weddings, family retreats, corporate events and so much more. Come see for yourself, everything you could possibly need is here. All measurements are approximate and are only for the main house. There is a whole farm diesel generator and a propane generator for main house and pool.

Listed by Lynn Rawson of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* 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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5932 VT Route 153 Rupert VT 05768

Rupert, VT5932 VT Route 153

Price$225,000

Est. Mortgage: $/month

MLS Number 4909605

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

Set on 2A in Rupert Vt. we have just listed this spacious (2500sf)Timber frame center hall colonial. Well maintained but in need of some aesthetic updating, this home could be a gem with generously proportioned rooms including an eat-in kitchen(with laundry),a large formal dining room complemented by a 3 season porch, a large living room with brick hearth and water jacketed wood stove, a bedroom or office, and full bath completing the main floor. Upstairs are 3 to 5 bedrooms/office space, and a second full bath. Amenities include oak and pine floors, a magnificent walk up attic(impressive timber frame), oil baseboard hot water heat, a 3 season porch, replacement thermopane windows throughout... Mettawee School pre -k thru 6, school choice 7-12

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* 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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Hebron Road Rupert VT 05776

Rupert, VTHebron Road

Price$120,000

Est. Mortgage: $/month

MLS Number 4934251

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 1
  • Square Feet 750

This is an adorably efficient camp on .25 acres in a beautiful rural location in Rupert, Vermont! Great road and gorgeous views. Wonderful little getaway! Only 15 minutes from Dorset. Come take a look!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* 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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4563 Route 315 Rupert VT 05761

Rupert, VT4563 Route 315

Rental Price$6,000

For Rent

MLS Number 4918692

  • Rentals
  • County Bennington
  • Property Type Rental
  • Bedrooms 3
  • Bathroom 2

SUGAR HILL GETAWAY...just minutes from the Dorset Green! Available Starting July 7th 2022 Newly listed for Seasonal Rentals. Vermont custom built New England style vacation home with 3 bedroom and 3 baths. Compact working kitchen with lots of natural light throughout. Sugar Hill exudes all the charm that you would expect in a Vermont vacation home. Sited on 8 private acres and nearby to the Merck Forest hiking trails, The Dorset Theatre Festival, and a bevy of fine restaurants. Minutes from the Dorset Union Store with some of the best prepared foods in Southern VT. Create vacation memories in this hidden gem.

Listed by TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* 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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Copyright 2022 New England Real Estate Network, Inc. All rights reserved. This display of listings may or may not be the entire Compilation from the NEREN database, and NEREN does not guarantee the accuracy of such information. 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 27, 2022 9:24 AM EST.