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. Learn More About the Rupert Area!

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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4075 Kent Hollow Road Rupert VT 05776

Rupert, VT4075 Kent Hollow Road

Price$450,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4869262

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

West Rupert Classic Vermont Farmstead Set along a quiet town maintained gravel road on +/-35 surveyed acres of gorgeous land is this c1826 3 bedroom, 2 bath classic colonial. The land and setting are truly magical with 5 to 10 acres of rolling meadowland, Oven Brook (a year-round babbling brook) coursing down through the hardwoods, incredible views and a few acres of land across the road from the home to ensure total protection of privacy. The home with its generously proportioned rooms consists of a large eat-in kitchen with wood stove, a study/den with brick wood burning fire place, a huge dining/living room with exposed beams and wood burning fireplace(wood stove insert)and a 3/4 bath with laundry. Adding to the generous living space is a spacious screened porch with distant views to the north and a sun room/green house on the south side. Upstairs are 3 bedrooms, a large landing/sitting area w/ built-ins and full bath. Amenities include a walk-up attic with gorgeous hand hewn beams, a full basement, whole house propane generator and detached 2 car garage with lean-to wood shelter. The house needs a bit of polishing/updating but is mechanically and structurally impressive with a newer oil furnace and oil tanks, all rewired, and has been well maintained. Come hear the sounds of the brook out your window.. Tucked in the hills of Rupert in Kent hollow - 20 minutes to the Dorset/Manchester areas and 35 min to the Saratoga Springs area Mettawee school and School choice 7-12

Listed by Scott Mcchesney of McChesney RE, Inc.

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$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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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Vermont Route 315 Rupert VT 05768

Rupert, VTVermont Route 315

Price$45,000

Est. Mortgage: $/month

MLS Number 4867138

  • Land
  • Acreage 4.4
  • Utilities None
  • Zoning RR

Quiet beautiful 4.4 acre parcel straddles babbling Mill Brook located close to Rupert Village approximately 1 acre cleared. Electricity available at the road. Minutes from Merck Forest and Farm Land Center with over 3,000 acres of protected land open to public for the classic Vermont outdoor activities. Located 35 minutes to Saratoga Springs, NY and just 20 minutes to Dorset/Manchester area. Enjoy the serenity of the Green Mountains with all the conveniences near by.

Listed by Josiah Allen Real Estate, Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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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557 Route 153 Rupert VT 05776

Rupert, VT557 Route 153

Price$170,000

Est. Mortgage: $/month

MLS Number 4867472

  • Residential Single Family
  • Bedrooms 3
  • Bathroom 1
  • Construction Existing
  • Zip 05776

Sweet c.1890's farmhouse surrounded by farmland in West Rupert, Vermont. Large, level yard perfect for gardening or just enjoy the gorgeous Vermont summer weather under one of the big ole' shade trees. Three bay barn/carport provides ample storage for vehicles and equipment as well as an attached shed just off the kitchen. Generously sized living room just a step off the front covered porch. Formal dining room, full bathroom, kitchen and office round out the first floor. Second floor offers three bedrooms. Some tlc would be necessary. The farmhouse is just around the corner from the West Rupert-Pawlet Rail Trail and the Village. So sweet.

Listed by Faith Rhodes and Melissa Genovart of Rhodes Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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! 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: 2.8% last updated on Jul 29, 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

Active With Contract

MLS Number 4846941

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

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.

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$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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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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
  • Bedrooms 4
  • Bathroom 3
  • Construction Existing
  • Zip 05761

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: 2.8% last updated on Jul 29, 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 Route 30 Rupert VT 05768

Rupert, VT682 VT Route 30

Price$199,900

Est. Mortgage: $/month

Pending

MLS Number 4839141

  • Residential Single Family
  • Bedrooms 4
  • Bathroom 2
  • Construction Existing
  • Zip 05768

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: 2.8% last updated on Jul 29, 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: 2.8% last updated on Jul 29, 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$350,000

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: 2.8% last updated on Jul 29, 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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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 August 2, 2021.