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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2910 Route 153 Rupert VT 05776

Rupert, VT2910 Route 153

Price$225,000

Est. Mortgage: $/month

MLS Number 4820243

  • Residential Single Family
  • Bedrooms 6
  • Bathroom 2
  • Construction Existing
  • Zip 05776

Classic Center Hall Colonial. 12 rooms/ 6 bedrooms/ 2 baths over 3000 square feet of charm and history waiting for you to call home. Step back in time when you are surrounded by mountain views and meadows. Slow down and relax as you enjoy one of the three porches. Upon entering the home you can feel the history. All the people and stories that have gone before us. This home once served as the Town Clerks Office and features an Authentic Timber Frame built in 1805 with hand trimmed beams. Well maintained and preserved. Needs some cosmetic updates- wall paper removal and painting.Ready for you to make it your own. A solid home with a great stone foundation, slate roof, drilled well and all the charm Vermont has to offer.

Listed by Margretta Fischer of Maple Leaf Realty

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$
%
$/month over payments
Federal 30-year interest rate: 2.99% last updated on Jul 30, 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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16 Clark Road Rupert VT 05768

Rupert, VT16 Clark Road

Price$475,000

Est. Mortgage: $/month

MLS Number 4818337

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

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.99% last updated on Jul 30, 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, this special offering features a beautifully renovated and expanded vintage residence, guesthouse, heated saltwater pool and 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 of Wohler Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.99% last updated on Jul 30, 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 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: 2.99% last updated on Jul 30, 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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369 Sykes Hollow Road Rupert VT 05761

Rupert, VT369 Sykes Hollow Road

Price$2,000,000

Est. Mortgage: $/month

MLS Number 4807072

  • Residential Single Family
  • Bedrooms 4
  • Bathroom 3
  • Construction Existing
  • Zip 05761

Traditional 1920's New England farmhouse located minutes from the Dorset Green. Property and buildings were renovated in 2010/2011 and have been meticulously maintained since. In addition to the main house, there is a guest house and studio apartment. Pond, pergola, brook, fruit trees, mature maples, porch and patios surround the farmhouse. The equine facilities are "A" show quality and include: seven stall barn (with heated tack room, wash stall with heat lamps, grain room, work area, loft for hay and shaving storage), 100 x 200 outdoor ring with TravelRight footing, 70 x 144 indoor ring with TravelRight footing, derby field, three large turn-out fields with run-in sheds and dry paddocks, three regular sized grass fields, three sand paddocks and equipment sheds. Alarm system, generator, chicken coop, and organic garden. Privacy and beautiful views. Sykes Hollow Road is right off of route 30 for easy access to Dorset, Manchester and Saratoga and all they have to offer. If you want to own and enjoy a classic Vermont horse farm property on 33 acres, this is one you need to see. Shown by appointment only. All measurements are approximate.

Listed by Tatsiana Clark of Four Seasons Sotheby's Int'l Realty

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$
%
$/month over payments
Federal 30-year interest rate: 2.99% last updated on Jul 30, 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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14 Sykes Hollow Road Rupert VT 05768

Rupert, VT14 Sykes Hollow Road

Price$469,000

Est. Mortgage: $/month

MLS Number 4801300

  • Residential Single Family
  • Bedrooms 3
  • Bathroom 2
  • Construction Existing
  • Zip 05768

Sykes Hollow renovated farmhouse. This property offers the best of both worlds; the style & charm of a vintage 1790's Vermont Farmhouse, but completely renovated and updated from the foundation up. Located on sought after Sykes Hollow road this home sits on three flat usable acres, and is surrounded by 25 acres of farm fields in Vermont Land Trust, giving the property a the sense of open space and Mountain views in several directions. Sit on your deck and enjoy the sunsets, or tend to your garden. This home offers many fine features including: 3 bedrooms and two new full baths, renovated granite kitchen with custom cabinets, center island, new chrome appliances, and deep country soapstone sink. The floors are a combination of hardwoods, softwood, ceramic tile. The great room provides a perfect place for everyone to relax, and a foundation base has been added during construction should a buyer want to add a wood burning fireplace to this room. The mudroom/entry has an attractive old brick floor laid in a vertical pattern. The heating system is baseboard hot water on the main floor and second floor, and the basement level has radiant heat in the floor should further expansion space be desired. The second floor has one bedroom and a full bath, and there is attic storage, or room for a new master bedroom suite to be added. There are some truly breath taking views from this property.

Listed by David Halligan of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.99% last updated on Jul 30, 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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926 Hebron Road Rupert VT 05768

Rupert, VT926 Hebron Road

Price$765,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4791123

  • Residential Single Family
  • Bedrooms 5
  • Bathroom 6
  • Construction Existing
  • Zip 05768

Rural work from home + quality of life experience. This elegant light-filled house was built in 2001 and offers plenty of interior space for play and study and to accommodate your work from home routine and for leisure time, a huge kitchen with space for sofas and chairs, a Wolf range for cooking and grilling then walk out to a covered porch to enjoy the view. You will find 5 bedrooms and 6 bathrooms in this roomy home, with over 9000 square feet under roof, 4950 square feet of healthy living space, with wood floors and no chipboard, 2800 square feet of walk out basement with 9 foot high ceilings and a 1500 square foot attic for a home gym. Both basement and attic are accessible by a full size, easy to use staircase. The house was designed and sited for passive solar and very self-sufficient, with plenty of firewood on the property for the 4 fire places, giant wood stove in the kitchen and the combined wood and oil furnace in the basement, a second oil furnace and a whole house water filtration system plus 2 on demand propane hot water heaters. The house will stand the test of time, with quarter sawn clapboard, 2 x 6 construction, by 2 x 12 roof supports 12 inches on center. Total privacy with a 1/2 mile long driveway in a park like setting off a town maintained gravel road, where you can practice your 5 K run to the border marker with NY State and on most runs only meet deer, turkey - and no cars.

Listed by Scott Mcchesney of McChesney RE, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.99% last updated on Jul 30, 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

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: 2.99% last updated on Jul 30, 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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115 Main Street Rupert VT 05776

Rupert, VT115 Main Street

Price$229,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4768556

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

Amazing opportunity! Commercially zoned Antique Center formally the J.H. Gould Company, this has serious potential. Live in the charming, one bedroom one bath cottage and renovate the front building into residential space for Rental income or set up shop and sell antiques ..... or anything else - live the good life in Vermont! Wonderful retail/craftsperson studio workspace. Open floor plan waiting for the next owner with a vision! Spring fed Pond out back is shared with the neighbor. Garage and Workshop for the Carpenter or Car enthusiast. . Cozy Cottage. Adjacent property ( 89 Main Street) also available as a package - both properties for $450,000 - Business and Pleasure wrapped all into one fabulous opportunity. Come take a look!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.99% last updated on Jul 30, 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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57 Ike Wright Road Rupert VT 05768

Rupert, VT57 Ike Wright Road

Price$495,000

Est. Mortgage: $/month

Pending

MLS Number 4763750

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

Built in 2005 with large addition added in 2017 this home in the country is picturesque! This 162 acre property features meadows, a pond, indian river, rail trail access and woods abundant in wildlife. Views of Mt. Antone from the master bedroom and side porch! Living room with cathedral ceiling, granite counter tops, custom tile master bath! This cozy home is close to Manchester and a short drive to Stratton, Bromley and Magic Mountain! A true Vermont paradise for nature lovers or those looking for peace and serenity!

Listed by Jason Saphire of www.EntryOnly.com

$
$
%
$/month over payments
Federal 30-year interest rate: 2.99% last updated on Jul 30, 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: 2.99% last updated on Jul 30, 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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TBD Foote Rupert VT 05768

Rupert, VTTBD Foote Road

Price$375,000

Est. Mortgage: $/month

MLS Number 4693545

  • Land
  • Acreage 17
  • Zoning Rural Residential

Last lot of four lot subdivision. Upscale, rural, private, quiet, mountain views. Foote Road. is quiet byway off Dorset West Road. Surrounding property values $500,000-3.000,000+. Rare opportunity for premium residence with privacy, views, access to golf, skiing,, fishing, hunting, biking, hiking shopping, cultural events.

Listed by R. Diedrich August of RE/MAX Four Seasons

$
$
%
$/month over payments
Federal 30-year interest rate: 2.99% last updated on Jul 30, 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 August 5, 2020.