Rupert Real Estate

Situated on the border of New York and Vermont is the town of Rupert, Vermont. Rupert is set in a beautiful rural setting. Rupert has a rich history you can see exemplified in its historic New England homes. 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.

Create a free account to save your favorite Vermont real estate listings and get notified when similar properties become available.

369 Sykes Hollow Road Rupert VT 05761

Rupert, VT369 Sykes Hollow Road

Price$2,000,000

Est. Mortgage: $/month

MLS Number 4841751

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

Situated in Southern Vermont's Mettowee Valley; minutes from Dorset/Manchester and close proximity to Albany, Saratoga, and Saugerties, you can't help but recognize the magical, calm feeling as you approach Sykes Hollow Farm. Upon turning up the tree lined drive, passing three grass paddocks, large fields with Run-In Sheds, Derby Field and a competition sized outdoor Ring (100 x 200) the charming reimagined (2011) farmhouse awaits your arrival. Consisting of four bedrooms and three baths, and a wonderful open country kitchen where there is room for guests to help with dinner preparations before adjourning to the wood beamed, candle lit dining room. After dinner you can curl up with a good book or board game in front of a roaring fire in the cozy living room. This home also enjoys a running brook, swimming and skating pond, seven stall show barn and 70 x 144 indoor ring. Add a two-bedroom guest cottage for family or guests plus a barn with a studio/groom apartment as well as space for yoga, dance or exercise in loft area. This 33-acre gem awaits the buyer who is looking to embrace all a Southern Vermont lifestyle has to offer, including golf, hiking, snow shoeing, skiing and the opportunity to make lifelong friends and memories. All measurements approximate.

Listed by Richard Slocum of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.02% last updated on Mar 4, 2021
* 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 TourAsk A QuestionMore Details

625 Sykes Hollow Road Rupert VT 05776

Rupert, VT625 Sykes Hollow Road

Price$1,300,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4816405

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 8
  • Bathroom 6

Situated just minutes from the Dorset Village Green along a quiet country road w/ fiber optic , this special offering features a beautifully renovated& expanded vintage residence, guesthouse, heated saltwater pool, barn with studio, situated with 122 acres of pasture and woodlands. The pastoral setting and charm of the residence cannot be overstated with a lovely stream, pond, beautiful stone walls and gardens. This unique property offers something for everyone throughout the year. Whether you seek a pasture for horses or mountainside recreation, the woodlands are ideal for hiking, mountain biking, snowshoeing, snowmobiling, hunting or tapping the maple trees. Well designed to work remotely with the full studio/guest suite above the barn. The beautifully expanded and updated 1778 main house has a breathtaking great room with wood burning fireplace, a formal dining room, a spacious open kitchen and a family room with second fireplace that opens to a screened porch and patio. Two masters en-suite and 3 additional bedrooms on the second floor provides ample room for friends and family. Enjoy a view of the pond, adjacent stream, heated saltwater pool and guest house from the screened in porch and patio. Your guests will never want to leave the 2 bedroom /2 bath guest house with living room and kitchen. The 3 car heated garage/barn includes a studio apartment with a large great room, kitchen & bath.The property exudes charm and peaceful country living yet convenience to Dorset.

Listed by Kim Morgan-Wohler and Trent Stephens of Wohler Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.02% last updated on Mar 4, 2021
* 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 TourAsk A QuestionMore Details

529 Antone Mountain View Road Rupert VT 05768

MLS Number 4848163

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

First time to market in 40 years: Architecturally striking 3 bedroom, 2 bath California Contemporary with unobstructed 180 panoramic mountain views. Sunsets are a painter's dream! The surrounding 43 acres offer both meadows and woodlands; streams; waterfalls; picnic spots; and trails for hiking, XC skiing, snowshoeing, and snowmobiling. The interior offers a two-level open floor-plan. The upper level features living, dining, and kitchen with beamed cathedral ceiling and two-story fireplace. Floors are TN distressed redwood and VT slate. The kitchen has elaborate Italian tile, plenty of cabinetry, and an authentic professional butcher block prep island. Two bedrooms have open views and hidden storage areas above closets with a bath in between. Lower level features a large family room with mountain views, a floor-to-ceiling fireplace, another bedroom, full bath, and separate entrance. Outdoor living space includes a large deck, hot tub, and railing seats for guests to enjoy dining and mountain views. In addition, there is an oversized 2-car garage and a shed for summer/winter toys. Land is in two parcels. The larger parcel has separate road frontage, so a few acres can be sold for a building site. Location is excellent: very close to Merck Forest (hiking/skiing) and nearby artistic Dorset/Manchester, yet only 35 miles from Saratoga Spring's famous racetrack/cultural activities & Lake George boating and water sports. Come see one of the most spectacular views anywhere in VT!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.02% last updated on Mar 4, 2021
* 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 TourAsk A QuestionMore Details

5491 VT Route 315 Rupert VT 05776

Rupert, VT5491 VT Route 315

Price$649,000

Est. Mortgage: $/month

MLS Number 4843731

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

Recently renovated three bedroom farmhouse, cozy one bedroom guest house, and detached garage with mountain views on 5+ acres. Located along the side of the road that heads up Rupert Mountain to Merck Forrest and merely two and a half miles from the Dorset green. It is now picture perfect with all new interior including kitchen and bath remodels, hardwood floors throughout, updated windows, wiring and plumbing. Further interior improvements include a master with master bath and walk in closet, new walls, ceilings and trim-work. Exterior improvements include the new renovated wood deck and covered porch. The main level consists of a formal living room (25 x 14) with wood burning fireplace, large country kitchen with dining area, half bath, family room (19 x 17) with wood stove inset/fireplace, and a combination mudroom & laundry. The second level consists of three good size bedrooms, two full baths, and a bonus room. There is a full attic accessed from a pull down ladder in hallway. The detached one bedroom cottage is bright and cheerful, with a cathedral ceiling, exposed beams, private sun deck, and separate driveway access. Come see all the improvements and make the special piece of Vermont your own!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.02% last updated on Mar 4, 2021
* 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 TourAsk A QuestionMore Details

Foote Road Rupert VT 05768

Rupert, VTFoote Road

Price$375,000

Est. Mortgage: $/month

MLS Number 4693545

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

Last available lot of four lot subdivision. Upscale, rural, private, quiet, mountain views. Foote Road. is quiet byway off Dorset West Road. Rare opportunity for privately situated residence with views and easy access to quality schools, historic village, golf, skiing,, fishing, hunting, biking, hiking shopping, cultural attractions.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.02% last updated on Mar 4, 2021
* 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 TourAsk A QuestionMore Details

595 Antone Mountain View Road Rupert VT 05768

MLS Number 4841825

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

Amazing Taconic Range Views and lovely setting away from it all yet convenient to Dorset/Manchester amenities WOW! An artistically presented contemporary that offers warmth, ease and one level living. This second home residence offers a natural low maintenance wooden exterior, grounds and a gazebo over looking pond. A separate detached 40x34 (3) car garage/barn/workshop with potential for upstairs renovation included kerosene heating for an office space. Kitchen great room is 26' X 27' with stainless appliances, slate floor that is open to the living/dining with a substantial VIEW! All living walks out onto expansive wrap around decking. Wood stove for those cozy nights in. Primary suite has a great view and tile bath ... a separate guest wing offers two bedrooms with bath. Some additional clearing shall expand the views. The private road is worth the assent up to this private perch. This residence is sited at the very top of Anton Mountain View which is a steep climb. The rewards: a second home sanctuary overlooking the areas finest SUNSETS!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.02% last updated on Mar 4, 2021
* 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 TourAsk A QuestionMore Details

3923 Kent Hollow Road Rupert VT 05776

Rupert, VT3923 Kent Hollow Road

Price$279,900

Est. Mortgage: $/month

MLS Number 4835486

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

Incredible surveyed 31.5 acre lot with long road frontage, beautiful open hidden fields protected by wood line perimeters would offer numerous options to build your new home or a perfect spot for a family retreat. An adorable A frame awaits the new buyer and has had recent renovations as late as 2011 and would be a perfect weekend get away or a place to stay while building your new dream home. The property also has a detached 2 car garage with additional attached room, offering a perfect conversion for your animals. The property is easy to walk, has a small pond, and beautiful mountain vistas grace the property. One of Vermont's prettiest spots and in a great recreational area as you will find the D & H bike trail in the center of Rupert and the Merck Forest hiking trails that are approximately 1.5 miles from this property. If you are looking for additional property, then the opportunity to buy an additional 191.5 across the street is possible. Let your dreams begin. Currently in land use but with the right offer seller would entertain removing. Property shares the water with the house across the street along with power but can easily be deeded or changed.

Listed by Hughes Group Team of Casella Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.02% last updated on Mar 4, 2021
* 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 TourAsk A QuestionMore Details

3923 Kent Hollow Road Rupert VT 05776

Rupert, VT3923 Kent Hollow Road

Price$279,900

Est. Mortgage: $/month

MLS Number 4835515

  • Land
  • County Bennington
  • Property Type Land
  • Acreage 31.5

Incredible surveyed 31.5 acre lot with long road frontage, beautiful open hidden fields protected by wood line perimeters would offer numerous options to build your new home or a perfect spot for a family retreat. An adorable A frame awaits the new buyer and has had recent renovations as late as 2011 and would be a perfect weekend get away or a place to stay while building your new dream home. The property also has a detached 2 car garage with additional attached room, offering a perfect conversion for your animals. The property is easy to walk, has a small pond, and beautiful mountain vistas grace the property. One of Vermont's prettiest spots and in a great recreational area as you will find the D & H bike trail in the center of Rupert and the Merck Forest hiking trails that are approximately 1.5 miles from this property. If you are looking for additional property, then the opportunity to buy an additional 191.5 across the street is possible. Let your dreams begin. Currently in land use but with the right offer seller would entertain removing. Property shares the water with the house across the street along with power but can easily be deeded or changed.

Listed by Hughes Group Team of Casella Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.02% last updated on Mar 4, 2021
* 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 TourAsk A QuestionMore Details

89 Main Street Rupert VT 05768

Rupert, VT89 Main Street

Price$279,000

Est. Mortgage: $/month

Active With Contract

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. Adjacent

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.02% last updated on Mar 4, 2021
* 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 TourAsk A QuestionMore Details

1205 Sandgate Road Rupert VT 05776

Rupert, VT1205 Sandgate Road

Price$265,000

Est. Mortgage: $/month

MLS Number 4846941

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

This antique three bedroom, 1.5 bath home is set along a town gravel road on over 3 acres with almost 800' frontage on White Creek. Originally converted from a c1805 barn (claimed to be one of the oldest remaining structures in West Rupert) this home has great character. The main floor has an eat-in kitchen with a large deck, and opens to the living room with exposed hewn beams, wood stove & cathedral ceiling, a full bath with laundry (W&D) and an office or bedroom. Upstairs has a large bedroom overlooking the beautiful, private yard and brook, a ½ bath and a second (double room) bedroom with views of the mountains across the road. The land and setting are truly magical - with about ½ open flat lawn/meadow land (great for critters & gardens) and the balance in hardwoods, a smaller stream and babbling White Creek for swimming and fishing! Some beautiful plantings, lilacs and mature landscaping. The house needs some TLC, but is a great space with good bones and a special setting; a solid value at $265,000. Additionally, there is a separately deeded 1 bedroom home/rustic cabin with existing drilled well and septic. The home needs major foundation repairs and fixing up (maybe a tear down- rebuild) but “pre-existing” for great use as guest house, rental, or airBnB on almost ½ acre. Package Price of $319,000, with total of +/-3.76A. Mettawee Community School pre-k thru 6, school choice 7 -12 and just 15 to 20 minutes to Dorset/Manchester areas

Listed by Scott Mcchesney of McChesney RE, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.02% last updated on Mar 4, 2021
* 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 TourAsk A QuestionMore Details

682 VT 30 Route Rupert VT 05768

Rupert, VT682 VT 30 Route

Price$199,900

Est. Mortgage: $/month

MLS Number 4839141

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 4
  • Bathroom 2

A 4 bedroom, 1.5 bath c.1900 Post Beam cape located in Rupert, Vermont. A large covered back porch overlooks the beautiful level 1.10 +/- acre tree lined lot where sounds of the Hager Brook can be enjoyed. The charming 19' beamed living room features a wood stove, bringing ambiance and warmth into the room. The 17' country eat in kitchen has a great south facing window and opens into the walk in pantry. The convenient first floor master bedroom is 12'x23' and sports a half bath. A new stainless steel liner installed in chimney 2011. A great back yard with plenty of room for gardening, pets, children's play, barbecuing or just relaxing. Small garage or large storage shed.

Listed by Lori Winn of New England Lakeside Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.02% last updated on Mar 4, 2021
* 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 TourAsk A QuestionMore Details

Pawlet Mountian Road Rupert VT 05776

Rupert, VTPawlet Mountian Road

Price$119,900

Est. Mortgage: $/month

MLS Number 4828972

  • Land
  • County Bennington
  • Property Type Land
  • Acreage 5

Listed by Nancy Liberatore of Lakes & Homes Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.02% last updated on Mar 4, 2021
* 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 TourAsk A QuestionMore Details

kent hollow Road Rupert VT 05776

Rupert, VTkent hollow Road

Price$24,500

Est. Mortgage: $/month

MLS Number 4815540

  • Land
  • County Bennington
  • Property Type Land
  • Acreage 10

Affordable 10A wooded parcel with babbling stream. Great for recreation, camping, hunting.. just up the road from trail head to Merck Forest (over 3000 acres of protected land open to public for hunting, hiking, cross country skiing). Possible potential to get seasonal camp permit (cabin with no interior plumbing). There is a section in the front along the road that is gently sloping/cleared - otherwise front of land is steep/difficult to access top/back portion other than hiking back. Beautiful quiet setting along town maintained back country gravel road.

Listed by Scott Mcchesney of McChesney RE, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.02% last updated on Mar 4, 2021
* 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 TourAsk A QuestionMore Details

Broker Reciprocity

Copyright 2021 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 March 7, 2021.