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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864 Rogers Road Rupert VT 05251

Price$2,400,000

Est. Mortgage: $/month

MLS Number 4771007

  • Residential Single Family
  • Bedrooms 4
  • Bathroom 6
  • Construction Existing
  • Zip 05251

Magnificent Country Estate property with privacy and views. Perfectly sited close to the town of Dorset and 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 50 acres going up to Spruce Peak. A two acre pond is surrounded by pristine fenced pasturelands. Beautifully landscaped gardens, attached barn, outdoor fireplace and covered porch are just some of the features offered. Property is managed for high quality timber production with a current standing timber value roughly at 1.2M. Also being offered with 642 acres and guest house.

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

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$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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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5251 Suncrest Rupert VT 05768

Price$299,000

Est. Mortgage: $/month

MLS Number 4769958

  • Land
  • Acreage 122.12
  • Zoning Rural

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

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$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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

Price$235,000

Est. Mortgage: $/month

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. Come take a look!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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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119 Watrous Road Rupert VT 05776

Price$267,800

Est. Mortgage: $/month

Pending

MLS Number 4767003

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

This classic log home equally well suited as an idyllic vacation retreat or a comfortable year round residence! The property is located minutes from the Dorset Green, on a lovely well-maintained town road. The property is on 10.7 pristine private acres with Merck Forest on two sides. There are landscaped grounds, trails, stonewalls, mountain streams, well-established perennial flower gardens that bloom profusely through the summer and fall. The setting is idyllic. The home is meticulously maintained with a Hearthstone soapstone wood-stove anchoring the living room which opens to the dining area off the kitchen. The home offers one bedroom on each level and a large open loft upstairs perfect for office/studio/guests. Master bedroom includes vaulted ceiling and a wood-burning fireplace. Lovely screened porch at the front of the house to relax and take in the sounds of the brook. Large patio at back of house is an ideal place for BBQ's with friends and family. Large detached oversize garage with finished room upstairs. Classic two story Vermont red barn offers more storage and parking. Woodshed next to house. Two garden sheds with additional woodshed. Wooded acreage and trails offer plenty of opportunity to cross-country ski, snowshoe, mountain bike, hike and bird watch. This beautiful property is the ideal home for all seasons. All measurements approximate.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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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318 Antone Mountain View Rupert VT 05768

Price$389,000

Est. Mortgage: $/month

MLS Number 4765057

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

Incredible mountain views, total privacy on 10 acres off a dead-end private road, and a great Rupert location just 5 miles to Dorset/40 minutes to Saratoga and almost adjacent to Merck Forest. A spacious 4 bedroom, 3 1/2 bath, 3,000+ sq ft home - impeccably maintained and beautifully designed to capture the views! Great space to spread out with family or house guests and set up nicely for single floor living with a new master bedroom wing on the first level and attached 2 car garage. Come enjoy cathedral ceilings, marble fireplace, new kitchen, sunroom, and stone terrace - hear the quiet and watch the sunset over the surrounding mountains! Mettawee School District- school choice- an incredible value and property!

Listed by Scott Mcchesney of Lee D. McChesney RE, Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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

Price$2,400,000

Est. Mortgage: $/month

MLS Number 4764906

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

This is the quintessential Vermont horse property located minutes from the Dorset green. The farm has it all: 33 acres of lush pastures, a swimming pond, brook and woodlands that run up to the edge of the property. Fantastic views of nearby mountains and Sykes Hollow. A classic horse barn with groom's apartment, 7 stalls, wash stall with heat lamps, heated tack room with washer and dryer in the grain room/work area. The hayloft has ample space for full loads of hay and shavings. Numerous sheds and outbuildings and a 2012 70 x 144 heated indoor riding arena with travel right footing. 100 x 200 outdoor ring with travel right footing. Derby field with ditch and bank. There are 2 over sized turn out fields, 2 large turn out fields... all with dry paddocks and run in sheds. 3 additional large turn out fields and 3 sand paddocks. The main 4 bedroom farmhouse was completely renovated in 2011. In addition to the main house there is a charming attached 2 bedroom guest house, which currently provides rental income. 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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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 Trail Rupert VT 05768

Price$495,000

Est. Mortgage: $/month

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: 3.55% last updated on Aug 22, 2019
* 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 Rd Rupert VT 05776

Price$49,000

Est. Mortgage: $/month

MLS Number 4761634

  • Land
  • Acreage 26

Set privately in the hills of West Rupert is this special +/-26 acre parcel with gorgeous mountain views and nice open meadow complete with a pond... Accessed by right of way- the land is comprised of 1/3 open meadow/pasture (ideal for horses/cattle) with balance in woodland (mostly steep). There is no site for septic for year-round home. This land would be limited to a seasonal camp or cabin permit only. Enjoy the peace and quiet- conveniently located +/- 20 minutes to Dorset/Manchester area and +/-45 minutes to Saratoga Springs, NY area- great for a Vermont cabin retreat!

Listed by Scott Mcchesney of Lee D. McChesney RE, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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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Perkins Hollow Road Rupert VT 05776

Price$59,900

Est. Mortgage: $/month

Active With Contract

MLS Number 4757079

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

Located in Perkins Hollow, Rupert Vermont, this seasonal camp has been owned by the same family for many generations. This is a beautiful area and the camp is at the absolute dead-end of the Hollow. Enjoy solitude, hunting, endless trails and fishing in the beautiful brook, with cascading waterfalls that runs along the front of the property.

Listed by Sara Buckley of Josiah Allen Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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

Price$995,000

Est. Mortgage: $/month

MLS Number 4754368

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

Within 15 minutes of Dorset, Stone Ridge Farm offers complete privacy and commanding views of the Taconic Mountains. The owners, purveyors of fine Scandinavian antiques, built the 4,950-square-foot residence in 2001 at the end of a ½-mile drive. The home is a New England farmhouse with a distinct Scandinavian influence, which reflects the timeless lineage of two cultures with its high craftsmanship and attention to detail. The interior design includes antique pickled pine floors, built in antique Scandinavian wall cabinets and four fireplaces. The Great Room with its gourmet kitchen, informal dining and sitting area is cozy with its defining Norwegian woodstove, and spacious with its 14-foot ceilings and endless views to the South and East. The living spaces are light filled and flexible in use. There are four en suite bedrooms with a master bedroom and generous 1st floor guest suite. A 2-story barn and 4-bay equipment shed complete the farmstead. Threaded through the 130 acres of meadows, ponds, orchards and woodlands are miles of trails to snow shoe, x/c ski, hike, bike or ride horses. The 40 mile D & H rail trail is close by, providing additional trails to enjoy. 16 miles from Manchester's fine dining and shopping, 22 miles to Bromley and 34 miles to Stratton.

Listed by Dia Jenks and T Story Jenks of LandVest, Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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

Price$535,000

Est. Mortgage: $/month

MLS Number 4751932

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

A Small Slice of Heaven. 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, and 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 looking both south down the Mettowee Valley and north toward a neighboring fenced horse pastures.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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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363 Ebenville Rupert VT 05776

Price$395,000

Est. Mortgage: $/month

MLS Number 4757489

  • Residential Single Family
  • Bedrooms 3
  • Bathroom 2
  • Construction Existing
  • Zip 05776

Charming restored antique cape home with five fireplaces. Lovely stone patio that overlooks the pond. Nice eat in kitchen with fireplace, den with fireplace, living room with fireplace and 3/4 bath on first floor. Three bedrooms and full bath with soaking tub overlooking the pond on the second story. Master bedroom has a fireplace as well as the walk out basement. Property is currently part of a larger parcel, see MLS 4336932. Owner will subdivide.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

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Copyright 2019 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 25, 2019.