Rupert VT Real Estate

Situated in the Taconic mountains of western Vermont, Rupert is a picturesque rural community with a small, friendly population of about 1000 year-round residents. The beauty of this town is realized with each passing season, as the lush green summer landscape turns a fiery red-orange in the fall, eventually covered by winter's sparkling snow. Learn More About the Rupert Area!

Discover current real estate for sale in Rupert, VT below. Search through a variety of listings including acres of land, residential homes, and more. Use the criteria to the right to narrow your results to particular towns or price ranges, etc. Save your favorites when you create an account, and you can get email updates when new properties match your search criteria. For more information and to schedule a showing, don't hesitate to contact us.

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3923 Kent Hollow Road Rupert VT 05776

Rupert, VT3923 Kent Hollow Road

Price$279,900

Est. Mortgage: $/month

MLS Number 4835515

  • Land
  • Acreage 31.5
  • Zoning unknown

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: 2.81% last updated on Oct 29, 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

MLS Number 4835486

  • Residential Single Family
  • Bedrooms 1
  • Bathroom 1
  • Construction Existing
  • Zip 05776

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: 2.81% last updated on Oct 29, 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
  • Acreage 5
  • Zoning residential

Listed by Nancy Liberatore of Lakes & Homes Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 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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5388 VT 315 Route Rupert VT 05768

Rupert, VT5388 VT 315 Route

Price$865,000

Est. Mortgage: $/month

Pending

MLS Number 4827232

  • Residential Single Family
  • Bedrooms 3
  • Bathroom 4
  • Construction Existing
  • Zip 05768

This 2017 Custom Build Modern Farmhouse is located just outside of Dorset Vermont and overlooks Farmland and beautiful mountain views. Designed by its current owners this very unique home has a main floor master suite, and two guests rooms and two baths on the second floor. The property also has a barn and an additional outbuilding, deck, partially fenced yard, and a detached 2 car garage. Understated elegance is a proper description for this special home.

Listed by Sara Buckley of Josiah Allen Real Estate, Manchester Branch Office

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 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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384 Neilson Road Rupert VT 05768

Rupert, VT384 Neilson Road

Price$1,800,000

Est. Mortgage: $/month

MLS Number 4822061

  • Residential Single Family
  • Bedrooms 3
  • Bathroom 3
  • Construction Existing
  • Zip 05768

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: 2.81% last updated on Oct 29, 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
  • Bedrooms 8
  • Bathroom 6
  • Construction Existing
  • Zip 05776

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: 2.81% last updated on Oct 29, 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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kent hollow Road Rupert VT 05776

Rupert, VTkent hollow Road

Price$24,500

Est. Mortgage: $/month

MLS Number 4815540

  • Land
  • Acreage 10
  • Zoning forest & Recreation

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: 2.81% last updated on Oct 29, 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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426 Sandgate Road Rupert VT 05776

Rupert, VT426 Sandgate Road

Price$119,900

Est. Mortgage: $/month

Pending

MLS Number 4775386

  • Residential Single Family
  • Bedrooms 2
  • Bathroom 1
  • Construction Existing
  • Zip 05776

The perfect Vermont getaway retreat. Set privately along a quiet town gravel road on +/-4 acres is this 50 year old (cedar shake sided) log home overlooking a crystal clear pond. The single floor cabin of about 1,000 sq ft has 2 vaulted ceilinged bedrooms, a cathedral ceiling spacious kitchen/dining area complete with stone fireplace, a living room wing with Vermont castings woodstove with hearth and 3/4 bath. Rustic, but nicely maintained and upgraded - spring water supply, OFHA for heat and a detached one car garage with shop space. Being sold furnished, +/- 20 minutes to Dorset/Manchester area.

Listed by Scott Mcchesney of McChesney RE, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 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
  • Bedrooms 5
  • Bathroom 2
  • Construction Existing
  • Zip 05768

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: 2.81% last updated on Oct 29, 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
  • Acreage 17
  • Zoning Rural Residential

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: 2.81% last updated on Oct 29, 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 Mountain Road Rupert VT 05776

Rupert, VTPawlet Mountain Road

Price$44,500

Est. Mortgage: $/month

MLS Number 4677491

  • Land
  • Acreage 6
  • Zoning TBD

Set along Pawlet Mountain Road this mostly wooded +/-6 acre parcel offers privacy, a babbling brook with waterfall and some nice views of Mount Antone with some minimal clearing. There is good access with over 350' road frontage and power right at hand. Mostly hardwoods- enough sugar maples for a “backyard sugarbush.” Great possible building lot subject to satisfactory soil tests and subdivision approval. A special parcel in a great location nearby Merck Forest- within 15 minutes to Dorset/Manchester area and less than an hour to Saratoga Springs. A solid value and opportunity at $44,500!

Listed by Scott Mcchesney of McChesney RE, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 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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334 Dole Road Rupert VT 05776

Rupert, VT334 Dole Road

Price$995,000

Est. Mortgage: $/month

Pending

MLS Number 4336932

  • Residential Single Family
  • Bedrooms 3
  • Bathroom 3
  • Construction Existing
  • Zip 05776

Mountain View Farm is a horseman's paradise. Panoramic far reaching views. Center chimney reproduction saltbox home with tunnels to the four plus garage garage barn and greenhouse. Brand new five stall horse barn with tack room that could easily be expanded to ten stalls. Two ten acre corrals with heated water troughs overlooks swimmimg pond. Restored cape cod caretaker's or guest home with 5 fireplaces, second pond, mature fruit trees all bordering lands of Merck Forest. Fantastic breathtaking property, a must see! Internet is available through Consolidated Communications.

Listed by Chip Watson of Josiah Allen Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.81% last updated on Oct 29, 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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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 October 31, 2020.