Our mobile site is optimized for smaller screens.

TRY IT NO THANKS
Advanced Search

      Rupert Vermont Real Estate

      Bennington County
      Chartered: August 20, 1761
      Area: 28,659 Acres = 44.78 Square Miles
      Population (US Census, 2000): 704
      Population Density (persons per square mile): 15.7

      Rupert Vermont is on the western side of Vermont, next to the New York border. It is just northwest of Manchester, Vermont, west of Dorset, Vermont, and south of Pawlet, Vermont. This small, quiet Vermont town features real estate of all types, including primary residences, vacation homes, and retirement homes. Just a short drive away one can be shopping in Manchester’s famous designer outlets or enjoying a play at the Dorset Playhouse. Rupert Vermont real estate is under an hour away from some of Vermont’s most popular ski resorts, including Stratton Mountain Ski Resort, Magic Mountain Ski Resort, and Bromley Mountain Ski Resort.

      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

      Ludlow/Okemo
      156 Main street
      Ludlow VT, 05149
      Office: 802-228-5678

      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: 3.95% last updated on 2017-05-25

      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 Real Estate, Inc.

      Ludlow/Okemo
      156 Main street
      Ludlow VT, 05149
      Office: 802-228-5678

      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: 3.95% last updated on 2017-05-25

      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 Willard Watson of Josiah Allen Real Estate, Inc.

      Ludlow/Okemo
      156 Main street
      Ludlow VT, 05149
      Office: 802-228-5678

      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: 3.95% last updated on 2017-05-25

      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$1,495,000The 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 Real Estate, Inc.

      Ludlow/Okemo
      156 Main street
      Ludlow VT, 05149
      Office: 802-228-5678

      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: 3.95% last updated on 2017-05-25

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

      195 Derby Hill, Rupert, VT 05768

      Price$1,300,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 4628396

      • Residential Single Family
      • Bedrooms 7
      • Bathroom 8
      • Stories 2
      • Construction Existing

      Private 18 acre resort-type compound 20 minutes to Manchester outlet shopping or 30 minutes to skiing, perfects the multi-generational family retreat! The three dwellings integrate seamlessly into a tranquil mountain top landscape with phenomenal views of the Mettowee Valley which is captivating at all hours and in all weather for all seasons. The design of the buildings and landscaping captures casual function, comfort and convenience with easy flow to outdoor expansive decking, walkways, and heated pool. The 4000 SF main residence offers 4 master bedrooms complete with spa tubs, steam showers, and sauna. From the chefs Kitchen great-room perfectly designed for entertaining... three fireplaces, spacious living room... every comfort is available. The 1700 sf party barn offers fully equipped kitchen, media room, staging, two additional rooms and bath with extended 80X40 asphalt basketball and tennis wall. The creatively appointed 1200 sf guest house offers 3 BRS/2 BA, 2 bonus rooms, common room, loft, pantry storage and connects to the 2 bay garage in addition to a 3 bay garage on site. Play house or tree house... every hobby and creative lifestyle desire is successfully accommodated. Certainly a one of a kind opportunity for personal use...or income... or corporate retreat. This is very special.

      Listed by Laura Beckwith of Josiah Allen Real Estate, Inc.

      Ludlow/Okemo
      156 Main street
      Ludlow VT, 05149
      Office: 802-228-5678

      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: 3.95% last updated on 2017-05-25

      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$1,150,000The 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 Real Estate, Inc.

      Ludlow/Okemo
      156 Main street
      Ludlow VT, 05149
      Office: 802-228-5678

      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: 3.95% last updated on 2017-05-25

      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$795,000The 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 $200,000 BELOW APPRAISED VALUE. All measurements are approximate.

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

      Ludlow/Okemo
      156 Main street
      Ludlow VT, 05149
      Office: 802-228-5678

      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: 3.95% last updated on 2017-05-25

      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$619,000The 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 Real Estate, Inc.

      Ludlow/Okemo
      156 Main street
      Ludlow VT, 05149
      Office: 802-228-5678

      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: 3.95% last updated on 2017-05-25

      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

      Ludlow/Okemo
      156 Main street
      Ludlow VT, 05149
      Office: 802-228-5678

      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: 3.95% last updated on 2017-05-25

      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

      Price$449,000The price has recently decreased

      Est. Mortgage: $/month

      MLS Number 4638990

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

      Well proportioned, handsome colonial farmhouse sits on a very private 7 acre parcel with beautiful mountain views and a pond. The house has 4 bedrooms and 4 baths plus a finished bonus room over the garage with a bthrm, which is presently being used as an office/guest room. Recent improvements include a new roof, updated master bath and new kitchen-both kitchen and mudroom floor are heated. Sit back and enjoy the serene surroundings on the striking new stone patio. An elegant offering not far from Dorset and Manchester.

      Listed by Vivian Thomas and Katherine Zilkha of Josiah Allen R. E., Inc./Manchester

      Ludlow/Okemo
      156 Main street
      Ludlow VT, 05149
      Office: 802-228-5678

      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: 3.95% last updated on 2017-05-25

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

      Broker Reciprocity

      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.