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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3044 Vermont 153 Route Rupert VT 05768

Price$169,500

Est. Mortgage: $/month

MLS Number 4781432

  • Residential Single Family
  • Bedrooms 3
  • Bathroom 1
  • Construction Existing
  • Zip 05768

Set nicely and privately back off the road on over 2 1/2 acres is this pretty c1935 3+ bedroom cape - loaded with character and curb appeal. The land has a nice yard and some fenced hillside pasture plus a 2 story workshop outbuilding. The house has a nice sized kitchen with new cabinets and a neat old farm sink, an office or guest bedroom, spacious living/dining room with fireplace (currently with pellet stove), exposed beams and oak floors. Finishing off the first floor is an office, master bedroom and newly done tile bath with marble sink. Upstairs has 2 bedrooms with gable dormers and great walk-out attic space. Amenities include full basement, updated wiring, attached 1 car garage, oil/wood hot air heat. A special little farmstead- just 10 minutes to Dorset, Mettawee school districts and school choice 7-12!

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

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$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 17, 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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2826 Pawlet Mountain Road Rupert VT 05768

Price$225,000

Est. Mortgage: $/month

MLS Number 4780034

  • Residential Single Family
  • Bedrooms 5
  • Bathroom 2
  • Construction Existing
  • Zip 05768

STORYBOOK SETTING. Set way back off from a country town gravel road, this 5 bedroom, 2 full bath Gambrel style home sits on an amazing 5 +/- acre parcel that will take your breath away. The landscaped yard with rolling meadows, apple trees and dotted with white birch creates a magical setting. A great floor plan with eat in kitchen, a 36 foot living-dining room accented with a gorgeous stone wood burning fireplace and a conveniently located first floor master bedroom suite with another romantic stone fireplace. The second floor host 4 very spacious bedrooms with another full bath. The 52' wrap around screened porch is great for reading, puzzle building, dining, sleeping, board games or an afternoon cocktail. Many improvements include a new roof in 2012, a new furnace in 2012, repointed chimney in 2011, all new thermopane windows, oil tank and a new hot water tank . The wood stove located in the basement is included. Beautiful gleaming hardwood flooring in all bedrooms plus the living-dining area. So if you are looking for complete privacy with a story book setting - stop your search. Mettawee School District with school choice 7-12.

Listed by Lori Winn of New England Lakeside Realty

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$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 17, 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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2774 315 Route Rupert VT 05761

Price$279,000

Est. Mortgage: $/month

MLS Number 4775789

  • Residential Single Family
  • Bedrooms 3
  • Bathroom 2
  • Construction Existing
  • Zip 05761

Beautiful well maintained 3 bedroom, 2 bath ranch, on 6 Acres, large lawn, babbling back yard stream, 2 car attached garage, 2 car detached garage. Great deer camp, only a few hundred yards from the 3,200 acre Merck Forest and Farmland Preserve, allowing for public hunting. Camp comfortably sleeps 4, open floor plan, great deck, sheds, views, nice lawn. Property also has a barn, and silo. Note: Property is located in the Town of Rupert, with a Pawlet, Vt. mailing address. The deer camp is taxed separately with an assessed value at $17,800 with total net tax at $371.24.

Listed by Michael Campbell of Michael Craig Campbell Realty

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$
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$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 17, 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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426 Sandgate Road Rupert VT 05776

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 Lee D. McChesney RE, Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 17, 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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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: 3.69% last updated on Oct 17, 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: 3.69% last updated on Oct 17, 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. Adjacent property ( 89 Main Street) also available as a package - both properties for $374,000 - Business and Pleasure wrapped all into one fabulous opportunity. Come take a look!

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

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$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 17, 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

Pending

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.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Oct 17, 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: 3.69% last updated on Oct 17, 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 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: 3.69% last updated on Oct 17, 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: 3.69% last updated on Oct 17, 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: 3.69% last updated on Oct 17, 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 October 18, 2019.