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Rupert & Pawlet VT Real Estate

Pawlet and Rupert are tucked to the North and West of Dorset surrounded by mountains and agrarian property. Home to Merck Forest & Farmland; 3,200 acres of sustainably managed forest and farmlands open to the public. Explore the 60 Acre farm, where pigs, sheep, chickens and horses roam free on sun-kissed green pastures. Unwind with a scenic hike on one of the over 30 miles of well-marked trails that wind through lush Vermont forest.  

Residents can enjoy the privacy Rupert and Pawlet have to offer while enjoying proximity to the area’s world-class activities. Take a short drive to Dorset Village and enjoy professional theatre at the Dorset Playhouse. Visit Manchester Center to indulge in a variety of excellent restaurants, shops and visit Lincoln’s Hildene, The Southern Vermont Arts Center and the Equinox Pond. 

Locals grab a slice of pie at Max’s General Store serving delicious woodfired pizza, and taste ethically harvested wild game at the Rupert Game Supper, a yearly event hosted at the Fire House featuring ethically harvested game from the mountains of Vermont.   

Chartered in 1761 and home to Reuben Harmon, a metalsmith given the right to mint coins called Vermont Coppers, Pawlet and Rupert have a rich chapter in Vermont’s history. Small and agrarian, the area still resembles its character from when it was first founded.   

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: 5.7% last updated on Jun 30, 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.

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166 McKeighan Road Rupert VT 05776

Rupert, VT166 McKeighan Road

Price$2,950,000

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? Need a gentlemen's farm for your pleasure horses? An estate suitable for an established events person? 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: 5.7% last updated on Jun 30, 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.

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330 Rupert Mountain Road Pawlet VT 05761

Pawlet, VT330 Rupert Mountain Road

Price$1,750,000

Est. Mortgage: $/month

MLS Number 4866985

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 6
  • Square Feet 6,748

This 55 acre family compound with fabulous views can accommodate alpacas, sheep, goats and horses. The home takes advantage of views throughout the four en-suite bedrooms, open living spaces and country kitchen. This property has been totally renovated, with a new standing seam roof, radiant heat, and new septic, windows, and doors. It has six outbuildings for housing animals, including one Morton building. All facilities are equipped with automatic waterers with immersible heaters. There is a large barn capable of housing four vehicles and 1,000 bales of hay. It also serves as the workplace on the farm. The pastures are fenced allowing for different size paddocks, depending on which gates are open/closed. The views are magnificent, with 900 feet on the Mettawee River, a lovely trout stream, and a fishing lodge. The home takes advantage of gorgeous views, open living spaces and a country kitchen. A piece of heaven in Pawlet, Vermont, just waiting to put your touch on it.

Listed by Moira Spivey of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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.

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5581 VT Route 30 North Pawlet VT 05761

MLS Number 4877774

  • Commercial
  • Year Built 1900
  • Acreage 2
  • Area In Town, Village

Established in 1972 from an 1800's barn, this impressive +/-5,000SF Timber frame restaurant has grown into a thriving business and destination. The unique and ideally configured 100+ seat restaurant lends itself beautifully to large or smaller private parties/gatherings with 4 separate dining areas. 1) Main Dining room (36+ seat/1,400SF) with soaring cathedral ceilings, a massive stone fireplace and huge windows looking down the Mettowee Valley. 2) Loft - open to/overlooking the main dining room - (400SF/ 25+ seats) 3) Tavern (30+ seat/850SF) with stone fireplace, performance platform for live music and 4) Seasonal Porch (20+ seat/360SF) accessed from the Tavern with steps to lawn/garden area and views down the Mettowee Valley. The current owners/operators have made many substantial improvements over their 20+ years of ownership. Including but not limited to new heating system(2 new boilers 2021), 5 split unit heat/AC pumps, installed an engineered/state approved septic, kitchen addition (over 600SF kitchen space), w/ 130SF walk-in cooler space, and all updated well maintained equipment. Architecturally&aesthetically pleasing, this "quintessential Vermont” Restaurant is truly a magnificent property. And the business is impressive as well with strong figures and continued growth and profitability! In 2019, the Gross revenue was close to $1,000,000 with over 30,000 meals served! And currently, revenue and profitability have both increased since then with fewer operating hours.

Listed by Scott Mcchesney of McChesney RE,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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.

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59 Waite Hill Road Pawlet VT 05761

Pawlet, VT59 Waite Hill Road

Price$725,000

Est. Mortgage: $/month

MLS Number 4885232

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Square Feet 1,466
  • Acreage 153.92

Words can not describe this gorgeous property- among the most photographed classic farms in Southern Vt. ! With Haystack Mountain providing the back drop, views from every vantage point on the property are stunning! The 153+- acres support 20 acres of active agricultural land, and 16 acres of associated open land suitable for pasturing. The balance of the property is mixed hardwood, hemlock, and white pine forest bordering the North Pawlet Hills Natural Area- owned by the Nature Conservancy. On the north side of a hemlock lined trout brook is a private and spectacular upland meadow, providing more close up views of Haystack and beyond! Pockets of maturing sugar maple provide opportunity for the novice or experienced sugarmakers! The house is in need of TLC and maybe more, but what a great location for an updated farmhouse and heritage estate! Enrollment in the Vt. Current Use program provides reduced property taxes and a sound plan for management of the forest resource! A superb Vermont real estate offering just minutes to the Dorset/Manchester area and Lake St. Catherine!

Listed by Mark Riley Sr of Vermont Forest and Field,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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.

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59 Waite Hill Road Pawlet VT 05761

Pawlet, VT59 Waite Hill Road

Price$725,000

Est. Mortgage: $/month

MLS Number 4884967

  • Land
  • Acreage 153.92
  • Utilities Other
  • Zoning ARR

Words can not describe this gorgeous property- among the most photographed classic farms in southern Vt.! With Haystack Mountain providing the backdrop, views from every vantage point on the property are stunning! The 153 +-acres support 20 acres of active agricultural land, and 16 acres of associated open land provide great potential for pasturing. The balance of the property is mixed hardwood, hemlock, and white pine forest bordering the North Pawlet Hills Natural Area-owned by the Nature Conservancy. On the north side of a hemlock lined trout brook is a private and spectacular upland meadow, providing more close up views of Haystack and beyond! Pockets of maturing sugar maple provide opportunity for the novice or experienced sugarmakers! The house is in need of TLC and maybe more, but what a great location for an updated farmhouse and heritage estate! Enrollment in the Vt. Current use program provides reduced property taxes and a sound plan for management of the forest resource! A superb Vermont real estate offering!

Listed by Mark Riley Sr of Vermont Forest and Field,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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.

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5491 VT Route 315 Rupert VT 05776

Rupert, VT5491 VT Route 315

Price$725,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4912861

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

Move in ready three bedroom center hall farmhouse, cozy detached cottage, detached garage and outbuilding, frontage on head waters to Mettowee river, big 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 renovated interior including kitchen and bath remodels, hardwood floors throughout, updated windows, wiring and plumbing. Further interior improvements include a master with master bath and huge walk-in closet. Exterior improvements include the renovated wood deck and covered porch both positioned to take in the stunning mountain views. 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 cottage is bright and cheerful, with a cathedral ceiling, exposed beams, and separate driveway access. Recent cottage improvements include sheetrock, interior paint and electrical upgrades. Come see all the improvements, walk down to the river - it's stunning, and make this 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: 5.7% last updated on Jun 30, 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.

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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: 5.7% last updated on Jun 30, 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.

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4599 Route 30 Pawlet VT 05761

Pawlet, VT4599 Route 30

Price$675,000

Est. Mortgage: $/month

MLS Number 4897958

  • Land
  • Acreage 48.33
  • Utilities Cable - Available
  • Zoning RR

Amazing Views !!!!!! Build your dream home. Also included is a small house and detached two car garage with living space above. Good for rental or care taker. Live in it while you build. SMALL PORTION OF LAND HAS A NO BUILD RESTRICTION

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

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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

4599 Route 30 Pawlet VT 05761

Pawlet, VT4599 Route 30

Price$675,000

Est. Mortgage: $/month

MLS Number 4911216

  • Residential Single Family
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 1,428
  • Construction Existing

Nice parcel with great views. Charming house with a separate two car garage with living space above-738 sq ft with a sleeping loft. This space needs to be completed. Small part of property restricted from building. Presently listed as land also.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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.

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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
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 3,955

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 Kristin Comeau of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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.

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296 Tadmer Road Pawlet VT 05761

Pawlet, VT296 Tadmer Road

Price$439,000

Est. Mortgage: $/month

MLS Number 4907881

  • Residential Single Family
  • Square Feet 2,340
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3

Quiet location on a little traveled town rd. Nice views over farm meadows and mountains. Family room with lots of glass. 18 mostly wooded acres that could be cleared for horses or out buildings. Recent new heating system and roof work. 48 hour notice to show. Existing tenant until 8/31/2022. Rent has been paid in advance and will be prorated to purchaser. Subject to a walking easement at the rear of the property by the neighbor

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

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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

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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 July 4, 2022.