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Rupert VT Real Estate

Located in the northwest corner of Bennington County and situated on the New York border, Rupert is a rural town in Vermont. Chartered in 1761, the town has had a long history of agriculture, serving as home to several dairy farms and maple sugar houses, many of which are still around today. Once contributing to Vermont’s reputation of “more cows than people”, Rupert now has a more lively community included in its villages of Ruper, West Rupert, and East Rupert. 

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999 Route 30 Rupert VT 05761

Rupert, VT999 Route 30

Price$3,995,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4904677

  • Residential Single Family
  • Bedrooms 5
  • Construction Existing
  • Square Feet 5,094
  • 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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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.29% last updated on 2022-09-22

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

166 McKeighan Road Rupert VT 05776

Rupert, VT166 McKeighan Road

Price$2,500,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4900123

  • Residential Single Family
  • Square Feet 5,956
  • Construction Existing
  • 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

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.29% last updated on 2022-09-22

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

4145 Route 153 Rupert VT 05768

Rupert, VT4145 Route 153

Price$995,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4929900

  • Residential Single Family
  • Bedrooms 5
  • Bathroom 4
  • Construction Existing
  • Square Feet 3,700

Historic Farmhouse located on 100+ acres in beautiful Rupert, VT! Built around 1850 or before, this home has 5 bedrooms / 4 baths, a beautifully renovated kitchen and a bright airy sunroom that looks towards the mountains. Sensational mountain views throughout the property. Originally settled by Revolutionary Veteran in 1780; known by recent generations as the C.I. Sheldon Farm, its barn was once the most "modern" in Rupert. Along with the larger barn and silo, there is a 3 car detached garage/barn with stalls and room for storage. The rail trail runs through the property which is great for walking, running or biking! There is a pond near the house and beaver ponds out by the headwaters of the Indian river next to the rail trail. There are other trails that adventure through the acres that can be used for many different activities! Equine friendly. Hunters paradise. Subdividable. Whole house generator. High end upgrades throughout. Well insulated. 5 fireplaces housing 2 beautiful VT wood stoves and 2 Regency remote/thermostat controlled high efficiency inserts. . 15 minutes to the villages of Pawlet and Dorset , 20 minutes to Manchester. Great opportunity. School Choice. Come take a look!

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

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.29% last updated on 2022-09-22

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

16 Clark Road Rupert VT 05768

Rupert, VT16 Clark Road

Price$675,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4901541

  • Residential Single Family
  • Bedrooms 4
  • Square Feet 2,708
  • Bathroom 4
  • Construction Existing

Tucked into the mountains of Rupert find this light and airy colonial with a private setting showcasing mountain views, and a manicured, landscaped yard with a pond. While feeling worlds away, you are merely 6 miles to Dorset Village or 12 to Manchester. From the covered front porch entry, access a spacious living room with wood burning fireplace to one side or the cozy den on the other. At the back of the home, you will find an updated kitchen with quartz counters, stainless steel appliances, heated tile floor, tile backsplash and an island to gather around. The kitchen is open to the dining room so this home has a great flow for entertaining and moving from room to room throughout an evening with friends and family. Relax at your Vermont hideaway from a stone patio off the kitchen and dining room or rock your worries away on the classic front porch. Plenty of large windows flood the rooms with light and views of the serene setting. Four bedrooms including the master with a beautifully updated bath are on the second floor and a bonus room and another bath over the garage provide additional options for guest spaces or living configurations. Get lost in the peaceful setting of 16 Clark Road but know you are never far from finding your way back to all the area's amenities.

Listed by Andrea Kaplan of Four Seasons Sotheby's Int'l Realty

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.29% last updated on 2022-09-22

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

5932 VT Route 153 Rupert VT 05768

Rupert, VT5932 VT Route 153

Price$229,500The price has recently decreased

Est. Mortgage: $/month

MLS Number 4909605

  • Residential Single Family
  • Construction Existing
  • Square Feet 2,542
  • Bathroom 2
  • Bedrooms 4

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.

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.29% last updated on 2022-09-22

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

4563 Route 315 Rupert VT 05761

Rupert, VT4563 Route 315

Rental Price$6,000The price has recently decreased

For Rent

MLS Number 4918692

  • Rentals
  • Bedrooms 3
  • Lease Term Monthly
  • Bathroom 2
  • Acreage 8

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 Alexandra Crowley and Elliott Nachwalter of TPW Real Estate

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.29% last updated on 2022-09-22

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Broker Reciprocity

Copyright 2022 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 27, 2022 1:10 AM EDT.

 

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