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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.

      864 Rogers Road, Rupert, VT 05768

      Price$3,600,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 4496096

      • Residential Single Family
      • Bedrooms 4
      • Bathroom 6
      • Area Abuts Conservation
      • Stories 2

      Country estate property with privacy and views. Perfectly sited at the end of a town maintained road to capture views of the Mettowee Valley and Green Mountain National Forest. Many well maintained trails traverse the 642 acres going up to Spruce Peak. A two acre pond is sounded by pristine fenced pasturelands. Beautifully landscaped gardens, attached barn, outdoor fireplace and covered porch are just some of the features offered. Property also has separate guest house and caretaker quarters. Property is managed for high quality timber production with a current Standing timber value at 1.2M and can be offered with an additional 278 acre building lot of mixed forest and open land .

      Listed by Andy Reed and Elena Atwill of Four Seasons Sotheby's Int'l Realty

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

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      Price Down Payment Interest Rate Years
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      Est. Mortgage: $/month

      Federal 30-year interest rate: 4.03% last updated on 2017-07-13

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

      792 Route 153, Rupert, VT 05768

      Price$2,250,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 4438207

      • Residential Single Family
      • Bedrooms 4
      • Bathroom 5
      • Stories 2
      • Construction Existing

      Stunning Vermont Vernacular on 284 acres! Incredible views, newly constructed(2010)legacy estate built with attention to detail and the highest quality materials. Long private drive to the top of the world! Recreation opportunity abounds! Hunt, fish White Creek or the Battenkill, ATV or snowmobile. Or relax by the 50 ft in ground resort quality pool and take in the view. Great equestrian potential. Four en-suite bedrooms, two fireplaces, gourmet kitchen with Viking range and Liebherr fridge, covered porch, two fireplaces. Finished basement with game room. Beautiful 33 x 28 ft storage barn and lovely grounds. Timber producing property in Current Use Program. Kohler Generator. 30 minutes to Saratoga and 15 minutes to Dorset. Incredible place. Must see.

      Listed by David Shehadi of Josiah Allen Dorset Office

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

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      Do not fill in this field:

      Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 4.03% last updated on 2017-07-13

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

      334 Dole Road, Rupert, VT 05776

      Price$1,595,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 4336932

      • Residential Single Family
      • Bedrooms 3
      • Bathroom 3
      • Area Rural
      • Stories 2

      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!

      Listed by Chip Watson of Josiah Allen Dorset Office

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

      Do not fill in this field:

      Do not fill in this field:

      Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 4.03% last updated on 2017-07-13

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

      926 Hebron, Rupert, VT 05768

      Price$1,395,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 4634662

      • Residential Single Family
      • Bedrooms 5
      • Bathroom 6
      • Stories 2.5
      • Construction Existing

      Bennington County 265 acres laced with over ten miles of open and trails which have been hand carved over the last 15 years to such vantage points that it is impossible not to appreciate every acre!!! The ponds, orchards, hidden meadows or pasture with equine run in and fencing, 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 reclaimed antique architectural niches, cabinetry, lighting and amazing flooring through out... Gracious Proportions 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 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 foreground. Remarkable unfinished attic and walk out 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 and Adrienne Sherwood of Josiah Allen Dorset Office

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

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      Do not fill in this field:

      Save FavoriteSchedule A VisitAsk A QuestionMore Details

      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 4.03% last updated on 2017-07-13

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

      926 B Hebron, Rupert, VT 05768

      Price$995,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 4635643

      • Residential Single Family
      • Bedrooms 5
      • Bathroom 6
      • Stories 2.5
      • Construction Existing

      Southern Vermont's "Stone Ridge" privately sited on 124 Serene acres laced with miles of trails that navigate to vantage points by foot, ski, all terrain vehicle or horseback... there's ponds, orchards, pasture and hidden meadows through hardwood forests. Wildlife lists grouse, woodcock, turkey, deer and beyond. The residence is nothing short of simple elegance with spacious proportions and 9 foot ceilings as well as vaulted kitchen great room and primary suite. Reclaimed antique architecture cupboards, hardware, flooring and mantels tell the story of intention that is meant for centuries past and to come... Extended primary rooms offer three window walls for vistas and southern light while fireplace hearths are noted in all the appropriate federal style locations... stone front foundation walls... steps...stone walls that create a low maintenance landscape against the Taconic Range with rolling hills in the foreground. Lower level light filled and drive in basement or finish the attic to expand options. This property located 15 minutes to Dorset and Manchester amenities beyond also is nearby airports... Getting away from it all is right here at your service!

      Listed by Laura Beckwith of Josiah Allen Dorset Office

      {$agent->Name}

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

      Do not fill in this field:

      Do not fill in this field:

      Save FavoriteSchedule A VisitAsk A QuestionMore Details

      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 4.03% last updated on 2017-07-13

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

      321 Rogers Road, Rupert, VT 05251

      Price$695,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 4607260

      • Residential Single Family
      • Bedrooms 4
      • Bathroom 4
      • Stories 1
      • Construction Existing

      Situated exactly 2.5 miles from the Dorset Green and the Dorset Union store, this impeccably maintained 4 bedroom home sits on almost 6 1/2 acres with stunning views. Beautiful landscaping with rock gardens, pathways, oriental koi pond and plenty of room for children and/or grandchildren to play. From the park like setting, enter into a stunning post and beam framed great room with exquisite detailing, cathedral ceiling, a window wall with additional transom windows and massive stone wood burning fireplace. The spacious, open and bright gourmet kitchen shares an equally spacious breakfast room. At one end of the home are 2 beautifully designed guest bedrooms with a full bath plus a very expansive family room with a propane fireplace and an additional ¾ bath. Situated privately 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 plus 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. ASKING PRICE IS $300,000 BELOW APPRAISED VALUE. All measurements are approximate.

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

      {$agent->Name}

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

      Do not fill in this field:

      Do not fill in this field:

      Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 4.03% last updated on 2017-07-13

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

      484 Herrick Brook Road, Rupert, VT 05768

      Price$595,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 4430316

      • Residential Single Family
      • Bedrooms 5
      • Bathroom 2
      • Stories 2
      • Construction Existing

      Incredible Mettowee Valley views from a special setting perched up on a hillside. Spacious Colonial Cape Offers Fine Country Living Just 5 miles To Dorset Green.Land Offered W/40 Acres (add. 21 avail w/2nd pond/stream) Fantastic private location yet close to both Manchester and Dorset. Rare find.

      Listed by David Shehadi of Josiah Allen Dorset Office

      {$agent->Name}

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

      Do not fill in this field:

      Do not fill in this field:

      Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 4.03% last updated on 2017-07-13

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

      863 Rogers Road, Rupert, VT 05768

      Price$499,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 4507513

      • Land
      • Zoning RR/FC
      • Acreage 278

      Escape to the hidden meadow protected by forest all around and build your dream home. Property has 278 acres with trails throughout. Currently being managed for Recreational use and Timber production. The location doesn't get any better, private yet only minutes from Dorset Village and the Dorset Field club.

      Listed by Andy Reed and Elena Atwill of Four Seasons Sotheby's Int'l Realty

      {$agent->Name}

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

      Do not fill in this field:

      Do not fill in this field:

      Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 4.03% last updated on 2017-07-13

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

      TBD Foote Rd., Rupert, VT 05768

      Price$375,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 4458080

      • Land
      • Area Rural
      • Zoning RR
      • Acreage 17.6

      Two contiguous 17+/- acre lots $375,000 each. Soils work, site plan, septic plan, road access plan all state and town approved. Fabulous sweeping East, Northeast and Southerly views of Green Mountains from elevated building sites. Meadow along road frontage (300 ft. per lot) and light woods rising to building sites. The two 17* AC. lots will be served by a planned single street access drive, curving to private drives on each lot to building envelopes. Underground Electric, Cable/Internet/phone are installed to entrance.Opportunity for buyer to purchase one or both lots. The quiet by-way Foote Rd neighborhood has handsome, well-spaced and designed colonial style homes. These lots offer a sense of community along with great privacy.

      Listed by R. Diedrich August of Dorset Village Properties

      {$agent->Name}

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

      Do not fill in this field:

      Do not fill in this field:

      Save FavoriteSchedule A VisitAsk A QuestionMore Details

      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 4.03% last updated on 2017-07-13

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

      5251 Suncrest Road, Rupert, VT 05768

      Price$349,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 4641850

      • Land
      • Zoning Rural
      • Acreage 122

      Extraordinary122 acre +/- land parcel with views, pastures,hayfields, stream, woodlands and multiple house sites with septic design and permits. This rare parcel is just 10 minutes to Dorset Green, yet a world away with privacy, peaceful location and a wonderful Vermont setting. Newly built driveway entry and culverts. Current owners have worked with USDA to improve wild life habitat and maintain apple orchard and hayfields. This special parcel offers a mix of pastures, orchards and woodland with timber. Opportunity abounds whether for equine, estate living with 4 house sites, agricultural, sugaring or timber. Simply a most exceptional opportunity to create and enjoy your Vermont country experience.

      Listed by Kim Morgan-Wohler of Wohler Realty Group

      {$agent->Name}

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

      Do not fill in this field:

      Do not fill in this field:

      Save FavoriteSchedule A VisitAsk A QuestionMore Details

      Price Down Payment Interest Rate Years
      %

      Est. Mortgage: $/month

      Federal 30-year interest rate: 4.03% last updated on 2017-07-13

      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 2017 Northern 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. Subject to errors, omissions, prior sale, change or withdrawal without notice. This web site is updated daily.