Rupert

Explore current real estate for sale in Rupert, Vermont. If you have any questions or if you'd like to see any of these properties in person, call 802-760-3100 or contact us online.

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864 Rogers Road Rupert VT 05251

Price$3,600,000

Est. Mortgage: $/month

MLS Number 4496096

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 4
  • Bathroom 6

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 642 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 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.

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

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$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 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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334 Dole Road Rupert VT 05776

Price$1,295,000

Est. Mortgage: $/month

MLS Number 4336932

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 3

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! Internet is available through Consolidated Communications. The owner would consider dividing the properties.

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

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$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 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 Road Rupert VT 05768

Price$995,000

Est. Mortgage: $/month

MLS Number 4692800

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 5
  • Bathroom 6

Bennington County 131 acres laced with trails that have been hand carved over the last 15 years to such vantage points that it is impossible not to appreciate every acre!!! The orchards, hidden meadows or pastures accommodate equine, 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 reclaiming antique architectural niches, cabinetry, lighting and amazing flooring through out... Gracious portions 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 room 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 the foreground. Remarkable unfinished attic and walkout 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 of Josiah Allen Real Estate, Inc.

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%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 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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63 Sykes Hollow Road Rupert VT 05776

Price$825,000

Est. Mortgage: $/month

MLS Number 4703350

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 4

Sykes Hollow Contemporary residence that has been custom designed and masterfully crafted for todays open concept living. The twelve acre site takes advantage of the distant mountain and meadow views as seen from a traditional wrap around deck which leads to the light filled living room with a cozy corner fireplace. The kitchen and adjoining pantry/wet bar is a cook's dream with high end appliances, granite counter tops, custom cabinetry and a breakfast nook. A spacious master bedroom takes advantage of the views from banks of windows and features an adjoining luxurious bath and over sized walk in closet. Two guest rooms and another bath complete the second story. A lower level has potential for a media or family room. This property is minutes from Dorset and is located 4 miles north of the Dorset Village Green in the picturesque Mettowee Valley.

Listed by Elena Atwill and Chris DeFelice of Four Seasons Sotheby's Int'l Realty

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$
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$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 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$769,000

Est. Mortgage: $/month

MLS Number 4732648

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 7
  • Bathroom 9

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 David Citron and Julie Citron of RE/MAX Four Seasons

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$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 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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6958 Route 153 Drive Rupert VT 05768

Price$475,000

Est. Mortgage: $/month

MLS Number 4666099

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 4
  • Bathroom 4

Phenomenal Gentleperson's Farmstead with 21 completely usable level acres that accommodates livestock, crops or equine needs... simply playful and open acreage nearby the 40 mile "rail trail" for walking, cross country skiing, snow shoeing, biking, trail riding or snowmobiling. The meticulously maintained residence is approached from the lightly traveled paved road over a substantial private bridge well lit... to a grand circular drive where the wrap around porch greets ... the attached two story garage is extra deep and the detached new barn houses all the toys! The livestock barn is off to the back... Patios and decks... fire-pit and BBQ set up amazes. The farm house has been revamped with a great protective infrastructure. The rooms flow in and out to all the out doors... There is a sunny kitchen that opens to two adjacent rooms that are noted as the study and dining room. Living Room, Family Room as well as a Bonus Room all entertain well for large or intimate gatherings... All 4 Bedrooms are on the upper level which also boasts additional sitting areas and oversized closet. A full Studio apt is located with a separate entrance over the garage. Surrounded by rural landscape with views over Rupert's rolling hills... The location is 35 minutes to Queensbury, NY at the southern end of Lake George... 15 minutes to Dorset... and 45 minutes to Saratoga...Stream side living the hammock awaits!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 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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TBD Foote Rupert VT 05768

Price$375,000

Est. Mortgage: $/month

MLS Number 4693545

  • Land
  • County Bennington
  • Property Type Land
  • Acreage 17

One of two remaining lots of four lot subdivision. Sold separately. Upscale, rural, private, quiet, mountain views. Foote Rod. is quiet byway off Dorset West Road. Surrounding property values $500,000-3.000,000+. Rare opportunity for premium residence with privacy, views, access to golf, skiing,, fishing, hunting, biking, hiking shopping, cultural events.

Listed by R. Diedrich August of RE/MAX Four Seasons

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$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 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

MLS Number 4705315

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 6
  • Bathroom 3

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

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$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 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$349,000

Est. Mortgage: $/month

MLS Number 4641850

  • Land
  • County Bennington
  • Property Type Land
  • 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

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$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 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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4451 Route 315 Rupert VT 05768

Price$299,000

Est. Mortgage: $/month

MLS Number 4702969

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 3

Spacious 3 bedroom, 2.5 bath colonial on 35 private acres of meadows and woods is only 3.5 miles to the Dorset Village Green. Lovely hardwood floors throughout the home, combined living/dining room opens into inviting sunroom with fireplace, which opens further onto sunny deck with meadow views. Master bedroom suite plus two more bedrooms and additional full bath upstairs. 2 car attached garage is currently in use as a studio but can easily be converted back to garage.

Listed by David Citron of RE/MAX Four Seasons

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$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 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
  • County Bennington
  • Property Type Single Family
  • Bedrooms 5
  • Bathroom 2

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: 4.17% last updated on Apr 18, 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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2824 Route 153 Route Rupert VT 05768

Price$225,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4659889

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 1

Unbelievable opportunity to own a cherished landmark in Rupert, Vermont that has been renovated into a home - the Sheldon Store. The store has been renovated into a 3 bedroom home with new insulation, heating system, well, plumbing, windows, various doors, and many other features and all while preserving the authentic finishes of the original store. And, if that's not enough, there is a house and a barn that goes with the property and ready for your finishing touches!

Listed by Paul W. Carrocio of TPW Real Estate Manchester Office

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 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

Pending

MLS Number 4735317

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 2

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.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 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

MLS Number 4722545

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 4
  • Bathroom 1

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 Coldwell Banker Watson Realty/Rutland

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 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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1127 Route 153 Rupert VT 05776

MLS Number 4728661

  • Commercial
  • County Bennington
  • Acreage 0.54

Here is a special opportunity to acquire and continue the legacy of one of Vermont's oldest country stores. The unique mansard roofed store's history can be traced back to c1858 and has hosted a masonic lodge ("Odd Fellows Hall") a theater known as Sheldon Hall, Grist Mill/Granary (with original huge wooden wheel and spindles in attic!) as well as the store through various owners and generations of Shermans .. It currently houses the West Rupert post office as well generating a monthly rental income. The store has had many upgrades and renovations and has +/-4,000 sq ft of store/office/kitchen space all on the main level. The cavernous basement and huge 2nd floor(the old theater) offers much additional space for expansion. Septic was redone c2005, drilled well, 4 leased split unit electric heat pumps for heating and cooling along with propane hot air furnace... The original antiquity and architectural details have been carefully preserved along with the addition of a commercial kitchen and outdoor rear porch with booths for seating. Such great character and myriad possibilities! Offered inclusive of store business, gas pumps and some kitchen equipment at $189,000

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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 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
  • County Bennington
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 2

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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 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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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 April 20, 2019.