Rupert VT Real Estate

Rupert, Vermont is located on the border of New York and Vermont. There is plenty of history and unspoiled nature to be found in Rupert. You may also be interested in viewing listings in other Vermont towns.

Explore Homes for Sale in Rupert, VT

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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
  • Construction Existing
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,988

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: 2.96% last updated on May 6, 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.

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348 Neilson Road Rupert VT 05768

Rupert, VT348 Neilson Road

Price$1,500,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4822061

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,970

Country charm and sophistication join hands in this special home perched high on a meadow in coveted Sykes Hollow-a perfectly tranquil setting. This home sits on 69 sub dividable acres with outstanding long range mountain views to the southwest. Equine friendly with a mix of flat pastures and woodlands. Tastefully appointed with plenty of natural light throughout. Amazing outdoor venue featuring a large covered porch and an adjacent stone patio. Entering this end-of-the-road- property one immediately gets a sense of peace and tranquility. Former horse stables converted into a 3 season guest house oozes with charm. Lots of trails for recreational use. Horses, ATV, Snowmobiling right out the door. 5 minutes to the Dorset Green. A very special offering. Simply sublime. Come take a look!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 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.

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529 Antone Mountain View Road Rupert VT 05768

MLS Number 4848163

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 2,016

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: 2.96% last updated on May 6, 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.

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5491 VT Route 315 Rupert VT 05776

Rupert, VT5491 VT Route 315

Price$649,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4843731

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,654

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: 2.96% last updated on May 6, 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.

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486 Rogers Road Rupert VT 05251

Rupert, VT486 Rogers Road

Price$525,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4857908

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 2,068

Wonderful Log home with 1990's beautiful addition on 47+ acres. Creek runs right by the home. Hiking trails up behind the house. Barns. Wonderful homestead waiting for the next owner. 5 minutes to the Dorset Green.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 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.

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Foote Road Rupert VT 05768

Rupert, VTFoote Road

Price$375,000

Est. Mortgage: $/month

MLS Number 4693545

  • Land
  • Acreage 17
  • Zoning Rural Residential

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: 2.96% last updated on May 6, 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.

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595 Antone Mountain View Road Rupert VT 05768
Active With Contract

MLS Number 4841825

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,382

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: 2.96% last updated on May 6, 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.

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1205 Sandgate Road Rupert VT 05776

Rupert, VT1205 Sandgate Road

Price$249,999

Est. Mortgage: $/month

MLS Number 4846941

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,167

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 $249,999. 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 $299,999. 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: 2.96% last updated on May 6, 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.

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682 VT 30 Route Rupert VT 05768

Rupert, VT682 VT 30 Route

Price$199,900

Est. Mortgage: $/month

Active With Contract

MLS Number 4839141

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 1,989

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: 2.96% last updated on May 6, 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.

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Pawlet Mountian Road Rupert VT 05776

Rupert, VTPawlet Mountian Road

Price$119,900

Est. Mortgage: $/month

MLS Number 4828972

  • Land
  • Acreage 5
  • Utilities Telephone Available
  • Zoning residential

Listed by Nancy Liberatore of Lakes & Homes Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 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.

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Sandgate Road Rupert VT 05776

Rupert, VTSandgate Road

Price$24,999

Est. Mortgage: $/month

MLS Number 4858727

  • Land
  • Acreage 1.3
  • Zoning ARR

Vermont Brookside Retreat A special opportunity - this beautiful Brookside meadow with great frontage along White Creek, easy access off a back town gravel road and Power at hand. The Parcel is fully in the river corridor and partially in the Zone A flood zone limiting it to agricultural/recreational use and allowing for the possibility of having a site for a seasonal RV camper. A very special setting and an affordable way to have that special piece of Vermont and your getaway retreat with fishing out your back door! Also available - directly across the road at 1205 Sandgate Road is a converted barn/3 bedroom home on 3+ Acres. A perfect package for the mini brookside farm! Located just 20 minutes to Manchester/Dorset areas and just over 1/2 hour to Saratoga Springs, NY

Listed by Scott Mcchesney of McChesney RE, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 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.

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kent hollow Road Rupert VT 05776

Rupert, VTkent hollow Road

Price$24,500

Est. Mortgage: $/month

MLS Number 4815540

  • Land
  • Acreage 10
  • Zoning forest & Recreation

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: 2.96% last updated on May 6, 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

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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 May 8, 2021.