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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.

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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Pawlet - Middletown Springs

5491 Vermont 315, Rupert, VT 05776

Price$399,000

Est. Mortgage: $/month

MLS Number 4705315

  • Residential Single Family
  • Listing Agent Name Terri Hathaway
  • Construction Existing
  • Bathroom 3
  • Bedrooms 6

This Vermont 1905 Farmhouse is looking for a new owner! Just along the side of the road that heads up to Rupert Mountain and merely two and a half miles from the Dorset green, with views of the Green Mountains and meadowlands she is waiting for you to love and restore her. The five-bedroom main house and out buildings including a one bedroom guest cottage, carriage barn and workshop all sit on five acres of land. Come make a special piece of Vermont your own!

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

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Josiah Allen, Dorset
3115 Vermont Route 30
Dorset VT, 05251
Office: 802.867.5555

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$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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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63 Sykes Hollow Road, Rupert, VT 05776

Price$825,000

Est. Mortgage: $/month

MLS Number 4703350

  • Residential Single Family
  • Listing Agent Name Elena Atwill
  • Construction Existing
  • Bathroom 4
  • Bedrooms 3

Sykes Hollow Contemporary residence that has been custom designed and masterfully crafted for todays open concept living. The twelve acre site takes advantage of the distant mountain and meadow views as seen from a traditional wrap around deck which leads to the light filled living room with a cozy corner fireplace. The kitchen and adjoining pantry/wet bar is a cook's dream with high end appliances, granite counter tops, custom cabinetry and a breakfast nook. A spacious master bedroom takes advantage of the views from banks of windows and features an adjoining luxurious bath and over sized walk in closet. Two guest rooms and another bath complete the second story. A lower level has potential for a media or family room. This property is minutes from Dorset and is located in the picturesque Mettowee Valley.

Listed by Elena Atwill and Chris DeFelice of Four Seasons Sotheby's Int'l Realty

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Josiah Allen, Dorset
3115 Vermont Route 30
Dorset VT, 05251
Office: 802.867.5555

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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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4451 Route 315, Rupert, VT 05768

Price$299,000

Est. Mortgage: $/month

MLS Number 4702969

  • Residential Single Family
  • Listing Agent Name David Citron
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3

Spacious 3 bedroom, 2.5 bath colonial on 35 private acres of meadows and woods is only 3.5 miles to the Dorset Village Green. Lovely hardwood floors throughout the home, combined living/dining room opens into inviting sunroom with fireplace, which opens further onto sunny deck with meadow views. Master bedroom suite plus two more bedrooms and additional full bath upstairs. 2 car attached garage is currently in use as a studio but can easily be converted back to garage.

Listed by David Citron and Julie Citron of RE/MAX Four Seasons

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Josiah Allen, Dorset
3115 Vermont Route 30
Dorset VT, 05251
Office: 802.867.5555

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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

Price$449,000

Est. Mortgage: $/month

MLS Number 4698217

  • Residential Single Family
  • Listing Agent Name Andrea Kaplan
  • Bedrooms 4
  • Bathroom 3
  • 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 and Courtney Leggett of Four Seasons Sotheby's Int'l Realty

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Josiah Allen, Dorset
3115 Vermont Route 30
Dorset VT, 05251
Office: 802.867.5555

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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 lot 3, Rupert, VT 05768

Price$189,000

Est. Mortgage: $/month

MLS Number 4694291

  • Land
  • Listing Agent Name Laura Beckwith
  • Acreage 57.2
  • Zoning rural residential

Rare, private parcel with fabulous Southern Mountain views from building site. 2000+ feet of road frontage on town maintained road. The land includes an old Homestead with apple orchard, two seasonal streams, woodland and pasture land with miles of stone walls. Good land for hunting... walking... trails... Permitted for 5 bedroom state waste water permit.

Listed by Laura Beckwith of Josiah Allen, Dorset

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Josiah Allen, Dorset
3115 Vermont Route 30
Dorset VT, 05251
Office: 802.867.5555

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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 lot 4, Rupert, VT 05768

Price$165,000

Est. Mortgage: $/month

MLS Number 4694303

  • Land
  • Listing Agent Name Laura Beckwith
  • Acreage 75
  • Zoning rural residential

75 Acre Recreation Parcel and wood lot... Seasonal dwelling only no septic. Southern exposures and lovely Green Mountain views... great all round hunting parcel from birding to white tail... Near town yet privately sited.

Listed by Laura Beckwith of Josiah Allen, Dorset

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Josiah Allen, Dorset
3115 Vermont Route 30
Dorset VT, 05251
Office: 802.867.5555

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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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Rupert, VT 05768

Price$375,000

Est. Mortgage: $/month

MLS Number 4693545

  • Land
  • Listing Agent Name R. Diedrich August
  • Acreage 17
  • Zoning Rural Residential

Two remaining lots of four lot subdivision. Sold separately. Upscale, rural, private, quiet, mountain views. Foote Rod. 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

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Josiah Allen, Dorset
3115 Vermont Route 30
Dorset VT, 05251
Office: 802.867.5555

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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 lot 1 Road, Rupert, VT 05768

Price$885,000

Est. Mortgage: $/month

MLS Number 4692899

  • Residential Single Family
  • Listing Agent Name Laura Beckwith
  • Bedrooms 5
  • Bathroom 6
  • Construction Existing

On this 44.7 acre sanctuary, the residence is impeccably designed with an eye for detail inspired by reclaimed antique architectural niches, cabinetry, lighting and amazing flooring throughout.... Gracious portions that flow easily for any lifestyle and need... The ceilings are 9 feet with vaults in the Great room, Kitchen and Master Suite of 14 feet... There are room extensions offering three window walls for the Living room, Great room and Master Suite. The Master also offers a generous three room suite with sitting room and fireplace, walk in closet creating private and luxurious quarters. The 5 fireplaces and hearths are in all the appropriate living areas... There are fabulous patchwork farming and rolling mountain views South to the Taconic Range. The remarkable fully ready for finish attic and walk out basement well lighted by windows offers auto/equipment drive-in feature as well as dumb waiter for bringing wood upstairs... A master piece in design and execution... Serenity... and all that land can give back to it's steward! 15 minutes to the Dorset Green... the 40 mile rail trail brings comfortable walks, bicycle and snow mobile access is steps away... easy access to Albany, Saratoga, Williamstown and all the greater Manchester amenities. ADDITIONAL ACREAGE AVAILABLE! Amazing estate quality offering!!!!

Listed by Laura Beckwith of Josiah Allen, Dorset

{$office->Name}

Josiah Allen, Dorset
3115 Vermont Route 30
Dorset VT, 05251
Office: 802.867.5555

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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 lots 1,2,3,and 4 Road, Rupert, VT 05768

Price$1,250,000

Est. Mortgage: $/month

MLS Number 4692800

  • Residential Single Family
  • Listing Agent Name Laura Beckwith
  • Construction Existing
  • Bathroom 6
  • Bedrooms 5

Bennington County 188 acres laced with trails that have been hand carved over the last 15 years to such vantage points that it is impossible not to appreciate every acre!!! The orchards, hidden meadows or pastures accommodate equine, wild life and lovely building sites are easily accessed... This is a sanctuary worth experiencing!!! The residence is impeccably designed with an eye for detail inspired by reclaiming antique architectural niches, cabinetry, lighting and amazing flooring through out... Gracious portions that flow easily for any lifestyle and need... The ceilings are 9 feet with vaults in the Great room, Kitchen and Master bedroom of 14 feet... There are room extensions offering three window walls for the Living room, Great room, Dining room and Master Suite which by the way offers generous three rooms of private and luxurious quarters. The fireplaces and hearths are in all the appropriate living and suite areas... The views to the Southern Taconic Range with gentle rolling mountains in the foreground. Remarkable unfinished attic and walkout windowed basement that offers auto drive in option and dumb-waiter... A masterpiece in design and execution... Serenity... and all that land can give back to it's steward! 15 minutes to the Dorset Green... 40 mile rail trail... easy access to Albany and greater Manchester amenities... Amazing Estate quality offering!

Listed by Laura Beckwith of Josiah Allen, Dorset

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Josiah Allen, Dorset
3115 Vermont Route 30
Dorset VT, 05251
Office: 802.867.5555

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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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321 Rogers Road, Rupert, VT 05251

Price$660,000

Est. Mortgage: $/month

MLS Number 4687526

  • Residential Single Family
  • Listing Agent Name Barbara Price
  • Construction Existing
  • Bathroom 4
  • Bedrooms 4

LOCATED EXACTLY 2.5 MILES FROM THE DORSET INN, DORSET GREEN & THE DORSET UNION STORE, this impeccably maintained 4-bedroom home sits privately on almost 6 1/2 acres with mountain views. Beautifully landscaped with rock gardens, pathways, oriental koi pond and plenty of room for outdoor play. From the park like setting, enter into a stunning post and beam great room with handsome detailing, cathedral ceiling, a window wall with additional transom windows and massive stone wood burning fireplace. The cherry flooring throughout the great room, dining area, breakfast nook, kitchen, foyer and mudroom has just been exquisitely refinished. The spacious, open and bright gourmet kitchen shares a very spacious breakfast room. At one end of the home are 2 bright guest bedrooms, with a full bath, a very expansive family room with a propane fireplace and another ¾ bath. Privately situated at the other end of the home is the master bedroom suite, which opens out onto a stone patio, plus an office/guest bedroom and full bath. This home is equipped with a generator. The free standing, 2 story post & beam barn/garage measuring 34' x 32', offers plenty of room for 2 cars and a workshop on the main level. Second floor is finished and heated providing endless possibilities. This property was APPRAISED IN SEPTEMBER 2015 FOR $995,000. All measurements are approximate.

Listed by Barbara Price and Courtney Leggett of Four Seasons Sotheby's Int'l Realty

{$office->Name}

Josiah Allen, Dorset
3115 Vermont Route 30
Dorset VT, 05251
Office: 802.867.5555

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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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1035 Sandgate, Rupert, VT 05776

Price$229,000

Est. Mortgage: $/month

MLS Number 4673735

  • Residential Single Family
  • Listing Agent Name Faith Rhodes
  • Bedrooms 3
  • Bathroom 2
  • Construction Existing

Everybody loves a great front porch! Enjoy the sounds of the stream or a crackling campfire in beautiful Rupert, Vermont! Situated on just under 2 acres, this wonderfully maintained 3 bedroom, 2 bath home is ready for you to move right in. Renovated in 2000. In true farmhouse style, the front porch welcomes you into a comfortable living room complete with built ins and hardwood floors. Conveniently located bedroom, laundry room, bathroom and a large eat in kitchen round out the first floor. The second floor offers an additional two bedrooms, large full bathroom, office and hardwood floors. The location is beautiful! Sit stream side on the front porch, enjoy a fire in the fire pit, pick a couple of apples or go for a hike. Out building provides great storage and large heated barn garage provides room for the big toys!

Listed by Faith Rhodes of Josiah Allen, Manchester

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Josiah Allen, Manchester
4532 Main Street
Manchester VT, 05254
Office: 802.362.3355

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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 A VisitAsk A QuestionMore Details

6958 Route 153 Drive, Rupert, VT 05768

Price$550,000

Est. Mortgage: $/month

MLS Number 4666099

  • Residential Single Family
  • Listing Agent Name Laura Beckwith
  • Bedrooms 4
  • Bathroom 4
  • Construction Existing

Phenomenal Gentleperson's Farmstead with 21 completely usable level acres that accommodates livestock, crops or equine needs... simply playful and open acreage nearby the 40 mile "rail trail" for walking, cross country skiing, snow shoeing, biking, trail riding or snowmobiling. The meticulously maintained residence is approached from the lightly traveled paved road over a substantial private bridge well lit... to a grand circular drive where the wrap around porch greets ... the attached two story garage is extra deep and the detached new barn houses all the toys! The livestock barn is off to the back... Patios and decks... fire-pit and BBQ set up amazes. The farm house has been revamped with a great protective infrastructure. The rooms flow in and out to all the out doors... There is a sunny kitchen that opens to two adjacent rooms that are noted as the study and dining room. Living Room, Family Room as well as a Bonus Room all entertain well for large or intimate gatherings... All 4 Bedrooms are on the upper level which also boasts additional sitting areas and oversized closet. A full Studio apt is located with a separate entrance over the garage. Surrounded by rural landscape with views over Rupert's rolling hills... The location is 35 minutes to Queensbury, NY at the southern end of Lake George... 15 minutes to Dorset... and 45 minutes to Saratoga...Stream side living the hammock awaits!

Listed by Laura Beckwith of Josiah Allen, Dorset

{$office->Name}

Josiah Allen, Dorset
3115 Vermont Route 30
Dorset VT, 05251
Office: 802.867.5555

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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 A VisitAsk A QuestionMore Details

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