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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Perkins Hollow Road Rupert VT 05776

Price$59,900

Est. Mortgage: $/month

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.

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$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 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

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$
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$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 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 05251

Price$565,000

Est. Mortgage: $/month

MLS Number 4751932

  • Residential Single Family
  • Bedrooms 3
  • Bathroom 2
  • Construction Existing
  • Zip 05251

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

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$
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$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 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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1035 Sandgate Rd Rupert VT 05776

Price$199,000

Est. Mortgage: $/month

Pending

MLS Number 4750453

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

Privately set off a town gravel road along babbling White Creek on almost 2 acres is this lovingly and thoroughly remodeled and renovated (2000) 3 bedroom, 2 bath home. A full length front porch takes full advantage of the magical setting. A spacious living room, eat-in kitchen, bedroom, laundry room 3/4 bath, and utility room make up the first floor. The second floor has a huge full bath, guest room and master bedroom with adjoining sitting or dressing room. Open the windows and enjoy the sounds of the babbling creek. A gorgeous yard with detached 2 car garage/shop (wood stove and coal stove for heat) and garden shed. An impeccable and special property.

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

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$
%
$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 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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3606 Kent Hollow Rd Rupert VT 05778

Price$167,500

Est. Mortgage: $/month

Active With Contract

MLS Number 4747604

  • Residential Single Family
  • Bedrooms 2
  • Bathroom 1
  • Construction Existing
  • Zip 05778

The details, craftsmanship and enchanting +/-8 surveyed acre setting is right out of a fairy tale. A perfect Vermont getaway retreat with the sounds of Oven Brook at your door- complete with foot bridge to your own back meadow where you can take in the views overlooking the gorgeous Kent Hollow setting. The c1865 antique cabin is loaded with character - wide-plank “bow-tie” floors, log doors and stairs, and stone fireplace/wood stove… Simple but perfect with generous living/dining room (FP and sliding door to patio/brook), ample kitchen, full bath and two low ceilinged cozy bedrooms upstairs. Amenities include 2007 installed septic, (Artesian) drilled well, oil hot air heat, 100 amp electric, etc

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

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$
%
$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 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.

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$
%
$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 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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60 Route 315 Rupert VT 05768

Price$219,000

Est. Mortgage: $/month

MLS Number 4735317

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

Beautifully restored and updated c1850 Victorian gem. Gorgeous woodwork throughout. Kitchen with soapstone sink and counters, stainless steel appliances and antique bead board cabinets. Also, bath with clawfoot tub, marble sink, tile shower, mudroom with slate floor, separate one car garage and front porch to enjoy the tranquil setting in the heart of Rupert. Great location, only 10 minutes to Dorset!

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

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$
%
$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 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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195 Derby Hill Road Rupert VT 05768

Price$695,000

Est. Mortgage: $/month

MLS Number 4732648

  • Residential Single Family
  • Bedrooms 7
  • Bathroom 9
  • Construction Existing
  • Zip 05768

A truly special property with loads of room including the 3700 square foot main house with 5 bedrooms, 1800 square foot 2 bedroom guest cottage, 1700 square foot party barn, two detached garages, additional outbuildings, flowing multi-level deck with long views down the valley, leading to the in-ground pool. Numerous features including wide pine floors, natural woodwork, spa-like bathrooms, sauna, radiant heat, multiple fireplaces and more. Must be seen to be appreciated, the possibilities are endless.

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

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$
%
$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 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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61 East Street Rupert VT 05776

Price$165,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4725626

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

Three Bedroom, Two Bath move in ready home. Beautiful open kitchen with maple cabinet and nice appliances. Very low maintenance home and property. Nestled in a peaceful Vermont village walking distance to country store, town office and post office. Easy 40 min. commute to Saratoga or Albany. Adorable Front porch. Huge unfinished basement and insulated attic space waiting for you to make your own. This modular home is comfortable and energy efficient. Come see it today! Priced to sell under assessment value!

Listed by Margretta Fischer of Maple Leaf Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 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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2438 VT Route 30 Rupert VT 05761

Price$209,900

Est. Mortgage: $/month

Active With Contract

MLS Number 4722545

  • Residential Single Family
  • Bedrooms 4
  • Bathroom 1
  • Construction Existing
  • Zip 05761

Nestled within the natural beauty of the Mettowee Valley sits this 1800's farmhouse that still inhabits old farm charm. The main house offers large open rooms for the growing family or those special gatherings. Each room is accented by the wood floors. A vintage style wood stove and traditional farm sink become the focal point of the first entry dining room. The kitchen is of its own separate room with plenty of alluring cupboards and counter space along with a fine crafted wood floor. The claw foot tub in the bathroom adds to the country charisma. There is a front room parlor, large living room and a formal dining room. Upstairs showcases 4 bedrooms with one bedroom offering direct access to the large storage space above the garage area. The mud room/entry room offers a washer/dryer hook up, stairs to the garage second level storage, direct entry to the garage and rear private deck. The lush trees along with the conserved farmland surrounding the property give a deep sense of privacy. The detached barn has been used as a professional woodworking shop over the years. The heat and electric are in place making it easy for the next owner to enjoy the 1200 sf space. Conveniently located between the villages of Pawlet and Dorset.

Listed by Rebecca Cramer of Watson Realty & Associates, PLC

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$
%
$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 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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89 Main Street Rupert VT 05768

Price$295,000

Est. Mortgage: $/month

MLS Number 4719939

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

Great opportunity! Village commercial historic 1850 Colonial. Four barns, spring fed pond, equestrian ready with all sorts of options and possibilities. Five bedroom/2 baths this charming property is located on Main St in the center of this quintessential New England village. Come be part of the Rupert Renaissance! Plenty of space for animals, gardens and farming,stalls,workshops, gym,etc. All flat meadow terrain with curb cuts on both routes 315 and 153. 10 minutes to Dorset Green and 20 minutes to Manchester Please see non public comments for several options concerning adjoining antique center and possible subdivision.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 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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5491 Vermont Route 315 Rupert VT 05776

Price$350,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4705315

  • Residential Single Family
  • Bedrooms 6
  • Bathroom 3
  • Construction Existing
  • Zip 05776

Have you looked at homes and wondered if you could move a wall to make an open floor plan or create a bigger mudroom or master? Here is your chance! Due to a freeze up this winter this wonderful property is ready for you to let your imagination take flight! Just heading up to Rupert Mountain's Merck Forest, 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 outbuildings include a one bedroom guest cottage, carriage barn, and workshop sited on five acres of land. Come make a special piece of Vermont your own!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.82% last updated on Jun 13, 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.

Virtual TourSave 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 June 15, 2019.