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

Scroll down to find real estate for sale in the Rupert, VT area. Find a variety of listings including residential, condos, land lots, and more. If you have questions or would like to schedule a showing, contact TPW Real Estate.

Search smarterRegister with our site to save your favorite listings and get updates when similar properties are new to the market.

999 Route 30 Rupert VT 05761

Rupert, VT999 Route 30

Price$3,995,000

Est. Mortgage: $/month

MLS Number 4904677

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 7
  • Square Feet 5,094

Hagarbook Farm completely restored 5034 SF C. 1767 Residence consisting of magnificent Mettowee River frontage interior to the 320 acres, Hagar Brook and Waterfall, Harmons Mint Historic Site, Pond, Agricultural Fields, Extensive Trail System and View Sites galore! The Land Straddles both East Rupert and Dorset. Add significant buildings in lovely condition: 750 SF Guest House, Barn 37 X 100, Tractor Barn 26 X 50, Horse Barn 50 X 28 and additional out buildings--24 X 18, 20 X 14, 20 X 12, 16 X 12, 40 X 24! An exemplary eighteenth century compound approximately 3 miles north of the Dorset Green. The Great-Room Kitchen with exposed post and beam framing is the welcoming hearth of the home which walks out to the wrap around porch or sun room to the west where the living extends upon a wonderful level stone walled terrace overlooking the grounds and river beyond. Crisp architectural details witnessed in every room; Dining, Living, Family, Office and 4 Wonderful Bedrooms up. There are 5 baths, 2 half baths and a guest house ... Whether it's agricultural or equine interest, stream & field, auto collector, historical appreciation or family gathering ideals, this property is a treasure. Vermont Current Use real estate tax benefits for the next steward to embrace. 320 acres in the prized Mettowee Valley nearby Dorset!!!

Listed by Charles Mauro of Josiah Allen Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 5.1% last updated on May 26, 2022
* 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

166 McKeighan Road Rupert VT 05776

Rupert, VT166 McKeighan Road

Price$3,200,000

Est. Mortgage: $/month

MLS Number 4900123

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 5,956

An estate for the most discerning of buyers. Have you been looking for an estate that combines exquisite details, views, and options for unlimited uses along with privacy? If so, this property is for you! 267.5 acres of rolling hills. Here you will find a custom built owner's residence which combines the moving of two barns which were rebuilt into one post and beam, owners residence. The detailing is second to none. A few steps from this home is the most amazing of pool houses which has every upgrade imaginable and allows for swimming 365 days/year, in all weather. There are four independent living accommodations along with a tractor barn, 6 bay animal pen, an animal holding barn with a separate veterinary room with heat and water, and walk in cooler. All electrical is underground. There are four ponds. No chemicals have been used anywhere on this land for the past 17 years so organic certification is possible. This is the estate to be at if another pandemic hits. This property is perfect for destination weddings, family retreats, corporate events and so much more. Come see for yourself, everything you could possibly need is here. All measurements are approximate and are only for the main house. There is a whole farm diesel generator and a propane generator for main house and pool.

Listed by Lynn Rawson of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.1% last updated on May 26, 2022
* 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

16 Clark Road Rupert VT 05768

Rupert, VT16 Clark Road

Price$699,000

Est. Mortgage: $/month

MLS Number 4901541

  • Residential Single Family
  • Bathroom 4
  • Square Feet 2,708
  • Bedrooms 4
  • Construction Existing

Tucked into the mountains of Rupert find this light and airy colonial with a private setting showcasing mountain views, and a manicured, landscaped yard with a pond. While feeling worlds away, you are merely 6 miles to Dorset Village or 12 to Manchester. From the covered front porch entry, access a spacious living room with wood burning fireplace to one side or the cozy den on the other. At the back of the home, you will find an updated kitchen with quartz counters, stainless steel appliances, heated tile floor, tile backsplash and an island to gather around. The kitchen is open to the dining room so this home has a great flow for entertaining and moving from room to room throughout an evening with friends and family. Relax at your Vermont hideaway from a stone patio off the kitchen and dining room or rock your worries away on the classic front porch. Plenty of large windows flood the rooms with light and views of the serene setting. Four bedrooms including the master with a beautifully updated bath are on the second floor and a bonus room and another bath over the garage provide additional options for guest spaces or living configurations. Get lost in the peaceful setting of 16 Clark Road but know you are never far from finding your way back to all the area's amenities.

Listed by Andrea Kaplan of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.1% last updated on May 26, 2022
* 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

455 Pawlet Mountain Road Rupert VT 05768

Rupert, VT455 Pawlet Mountain Road

Price$599,000

Est. Mortgage: $/month

Pending

MLS Number 4911025

  • Residential Single Family
  • Construction Existing
  • Square Feet 3,955
  • Bedrooms 3
  • Bathroom 3

Tucked in the Taconic Mountains, you will discover this spacious log home situated on 20 +/- acres. The property offers mountain views and a sense of retreat, located between Dorset Village and historic Salem, NY. Available for the first time in 25 years, this home features plenty of space, natural light and warmth. The living area is highlighted by a vaulted ceiling, skylights, French doors and a cast iron wood stove that warms winter nights. The vaulted ceilings and skylights continue in the spacious kitchen which includes an island with additional prep sink, double convection ovens, built in sideboard and breakfast table. Upstairs you will find a loft with built in storage. On the west wing of the home is the primary suite, office and third floor bonus room. The entry/first floor includes two generous bedrooms and full-bath, workshop, mudroom entry with access to the heated 2+ car garage. The wrap-around deck boasts a three-season room and overlooks the mountain and meadow views. Amenities to keep you comfortable year-round include: central A/C & radiant heat for main living areas, an automatic whole house generator, security system and new hot water heater. Enjoy the splendor of each season in the Green Mountain State, with easy access to all the area has to offer. Showings begin Friday 5/20 1pm.

Listed by TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 5.1% last updated on May 26, 2022
* 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$350,000

Est. Mortgage: $/month

Pending

MLS Number 4693545

  • Land
  • Acreage 17.67
  • 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: 5.1% last updated on May 26, 2022
* 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

1000 Bear Mountain Camp Road Rupert VT 05776

MLS Number 4908121

  • Residential Single Family
  • Bedrooms 1
  • Square Feet 1,068
  • Construction Existing
  • Acreage 135

Tucked away in the hills of the southern VT town of Rupert, these 135 +/- acres offer amazing mountain views, open fields, orchards & a mature forest! Located at the end of a private, seasonal shared road, the property offers an ideal vacation getaway, hunting paradise or potential homesteader property with 2 +/- acres of open fields, 23 apple trees, 2 streams & a unique off-grid cabin with small ponds nearby. Ready for your finishing touches, the cabin was recently remodeled with a new roof, windows, kitchen, tongue & groove pine interior, hot water sink & shower, stabilized footings & an addition! Siding is not complete & will be the buyer's responsibility. Gated access posted & well-marked with blazes & pins, so you'll know exactly what you own. An excellent wood roads through the property makes ATV & foot access easy. Setup specifically for hunting with food plots, 4 permanent stands & shooting lanes. VAST snowmobile trail access just off the property to the east. Serviced by an outhouse with water brought in for the shower & sink. Heated by a woodstove with wood from the property. Satellite TV & internet with the home setup for a portable generator. Fantastic views of the near & far mountains to the north & west. Just north of Manchester, VT with great shopping, fine dining & skiing. This property may be beautifully rustic but your activities don't have to be!

Listed by Curtis Trousdale and Michael Wrobel of Preferred Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 5.1% last updated on May 26, 2022
* 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

1000 Bear Mountain Camp Road Rupert VT 05776

MLS Number 4907955

  • Land
  • Acreage 135
  • Area Rural
  • Waterfront 2400

Tucked away in the hills of the southern VT town of Rupert, these 135 +/- acres offer amazing mountain views, open fields, orchards & a mature forest! Located at the end of a private, seasonal shared road, the property offers an ideal vacation getaway, hunting paradise or potential homesteader property with 2 +/- acres of open fields, 23 apple trees, 2 streams & a unique off-grid cabin with small ponds nearby. Ready for your finishing touches, the cabin was recently remodeled with a new roof, windows, kitchen, tongue & groove pine interior, hot water sink & shower, stabilized footings & an addition! Siding is not complete & will be the buyer's responsibility. Gated access posted & well-marked with blazes & pins, so you'll know exactly what you own. An excellent wood roads through the property makes ATV & foot access easy. Setup specifically for hunting with food plots, 4 permanent stands & shooting lanes. VAST snowmobile trail access just off the property to the east. Serviced by an outhouse with water brought in for the shower & sink. Heated by a woodstove with wood from the property. Satellite TV & internet with the home setup for a portable generator. Fantastic views of the near & far mountains to the north & west. Just north of Manchester, VT with great shopping, fine dining & skiing. This property may be beautifully rustic but your activities don't have to be!

Listed by Curtis Trousdale and Michael Wrobel of Preferred Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 5.1% last updated on May 26, 2022
* 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

5932 VT Route 153 Rupert VT 05768

Rupert, VT5932 VT Route 153

Price$229,500

Est. Mortgage: $/month

Active With Contract

MLS Number 4909605

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 2,542

Set on 2A in Rupert Vt. we have just listed this spacious (2500sf)Timber frame center hall colonial. Well maintained but in need of some aesthetic updating, this home could be a gem with generously proportioned rooms including an eat-in kitchen(with laundry),a large formal dining room complemented by a 3 season porch, a large living room with brick hearth and water jacketed wood stove, a bedroom or office, and full bath completing the main floor. Upstairs are 3 to 5 bedrooms/office space, and a second full bath. Amenities include oak and pine floors, a magnificent walk up attic(impressive timber frame), oil baseboard hot water heat, a 3 season porch, replacement thermopane windows throughout... Mettawee School pre -k thru 6, school choice 7-12

Listed by Scott Mcchesney and Robin Chesnut-Tangerman of McChesney RE,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 5.1% last updated on May 26, 2022
* 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

2528 VT Route 30 Rupert VT 05761

Rupert, VT2528 VT Route 30

Price$119,500

Est. Mortgage: $/month

MLS Number 4908585

  • Residential Single Family
  • Square Feet 1,800
  • Bathroom 2
  • Construction Existing
  • Bedrooms 4

A major opportunity needing some major work! This c1805 +/-4 bedroom 1 1/2 bath Greek Revival colonial has some good bones to work with as well as a drilled well, grandfathered septic for full time residence & a great location!... Decent full basement with stone foundation and slate roof and a nice flow/floor plan. Some original moldings, doors, floor boards and some nice trim details & original clapboards on the exterior. Solid attached garage - perfect to use as the workshop during restoration. Kitchen & bath need to be gutted and the plumbing/heating needs to be repaired/replaced. A very special location and a nice level 1 A parcel surrounded by Vermont Land Trust protected farm land and just a couple miles to the Dorset Green! Mettawee School District/School choice 7-12 and state of the art fiber-optics high speed internet Your opportunity to own a special piece of the famed Mettowee Valley!

Listed by Scott Mcchesney and Robin Chesnut-Tangerman of McChesney RE,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 5.1% last updated on May 26, 2022
* 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

Broker Reciprocity

Copyright 2022 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 28, 2022.