Wohler Realty Group company logo.
Company logo for Wohler Realty Group
Give Us A Call: 802-297-3333

Search Vermont Real Estate

Rupert & Pawlet VT Real Estate

Sign Up Here Call Our Office

Browse real estate for sale in Rupert and Pawlet, Vermont. See a listing you like? Contact Wohler Realty Group here or click to call our office at 802-297-3333 to schedule a home showing. Create a free account to save your favorite listings and receive updates when new properties come on the market.

Rupert & Pawlet VT Properties

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.   

1035 VT Rte 153 Pawlet VT 05775

Pawlet, VT1035 VT Rte 153

Price$950,000

Est. Mortgage: $/month

MLS Number 4971258

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 2,757

Welcome to Wayward Goose Farm, a serene and picturesque colonial-style farmhouse nestled in the heart of West Pawlet, Vermont. This sprawling estate offers an unparalleled opportunity to experience the quintessential Vermont dream. Situated on 28 acres of pristine land,this property is a haven for nature lovers and enthusiasts of all kinds. As you enter the home, you'll be greeted by an open and lofted floor plan, featuring 3 bedrooms and 2.5 bathrooms. The primary ensuite is conveniently located on the first floor, providing ease and comfort. The open kitchen, living, and dining area create a welcoming atmosphere, perfect for gatherings and entertaining.The second floor boasts two additional bedrooms, each offering its unique charm and character.There is also an full bathroom. Ascend to the 3rd-floor loft, a versatile space that can serve as an office, additional bedrooms, or storage, allowing you to tailor it to your needs. The property also features an attached garage with radiant heating, an art studio that can double as an office, and a fully finished studio apartment above the garage, complete with its own private entrance, full bathroom and has been successfully utilized as an AirBnB.The full concrete basement provides endless possibilities. You'll also find numerous outbuildings, including a newer farmstand, a milking parlor, a milking room, and a spacious barn for many uses. Additional adjacent land available for purchase, inquire with agent.

Listed by Annette Gallo of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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

63 Route 315 Rupert VT 05768

Rupert, VT63 Route 315

Price$225,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4971182

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 2,382

Welcome to a piece of history nestled in the picturesque town of Rupert. This circa 1850 home boasts 4 bedrooms, a spacious bonus room, and a plethora of unique features that blend the charm of yesteryears with modern amenities. With a new roof in 2015 and updated 220 electric in 2022, this home offers the perfect balance of old-world character and contemporary convenience. Step back in time as you enter this well-preserved piece of history. Many original features have been lovingly maintained, including the vintage doors, ornate door knobs, and a classic clawfoot tub. You'll be transported to a bygone era while enjoying the comforts of today. This home boasts 4 generously sized bedrooms and each room has its own unique character, with large windows that fill the rooms with natural light. A large bonus room offers versatility for a home office, playroom, or an additional living space. Its ample size allows you to customize it to fit your specific needs. Step outside to discover a world of outdoor entertainment. A deck with a built-in bar runs alongside the pool, perfect for summer gatherings and BBQs. The deck and pool area offer a seamless transition from indoor to outdoor living. The property also includes a charming carriage barn, ideal for storage, a workshop, or creative endeavors. If you've been searching for a unique blend of historical charm and modern comfort, this circa 1850 home is a must-see. First showings will be the open house Monday, Sept 25th from 11-1.

Listed by Carrie Mathews of William Raveis Winhall

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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

864 Heatherington Road Pawlet VT 05775

Pawlet, VT864 Heatherington Road

Price$589,000

Est. Mortgage: $/month

MLS Number 4969891

  • Residential Single Family
  • Bathroom 3
  • Construction Existing
  • Square Feet 2,444
  • Bedrooms 3

Welcome Home to Rush Hollow! This beautiful property boasts a lovingly restored three bedroom, three bath, 1850s farmhouse on almost 6 expansive acres of meadow and woods. Across from the house a large gambrel barn awaits with 6 horse stalls, power and water, and plenty of room for equipment, storage, projects, or warm weather events. Relax on the patio to sounds of the creek burbling past the wood fired sauna, over the small waterfall into the pond. Or just stroll among the fruit trees, berries, and perennial plantings and soak up the sunset views. Drop your coat and boots in the mudroom and step into the country kitchen with large island, tile floor and open to the inviting dining room with creek views and a brick fireplace. Cozy up in front of the big stone fireplace in the living room where large insulated windows flood the rooms with natural light picking up the glow of the wide wood floors. In the back a large slate floored studio/office/great room offers a third fireplace fitted with a crackling wood stove. Upstairs tasteful accents, plank wooden doors, and wide pine flooring continue the historic charm. The large primary suite captures the warm western light and ambience while the tiled bath offers a luxurious deep soaking tub. Two additional bedrooms and another bath complete the upstairs. This tranquil homestead offers both the privacy of a town maintained dead end road and easy access to Manchester, Lake St Catherine, and Bromley Mountain just 40 minutes away.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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

3987 Route 133 Pawlet VT 05761

Pawlet, VT3987 Route 133

Price$175,000

Est. Mortgage: $/month

MLS Number 4968308

  • Residential Single Family
  • Bathroom 1
  • Bedrooms 2
  • Construction Existing
  • Square Feet 1,873

Rarely do we see an opportunity like this come along! Take this +/-5 acre building lot with beautiful flat and rolling meadows and pasture land with incredible southeasterly mountain views; add to that the solid timber frame bones of a vintage 1.5 story c1800 cape with small barn/outbuilding and you are well on your way to becoming a Vermont Farmsteader. Located along a lightly traveled county road just minutes from Pawlet Village, Wells Village(Lake ST Catherine) and Granville, New York - you will have rural privacy with the convenience of amenities nearby. Although the house was occupied steadily until 2010 - it has been vacant since then and will need significant repairs...total rehab.. Possibly rebuild the home or salvage the hand hewn timber frame and build back on the land for additional privacy and views! There is a new wastewater disposal design for a 5 bedroom house available with a Vermont state ww permit pending. This property is ideal for some animals or simply a gorgeous country setting for your forever Pawlet home. School choice for grades 7 - 12 and high speed Fiber Optic Internet available. Showings begin Monday 9/04

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

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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

1037 Kelley Hill Road Pawlet VT 05761

Pawlet, VT1037 Kelley Hill Road

Price$579,000

Est. Mortgage: $/month

MLS Number 4963134

  • Residential Single Family
  • Bathroom 1
  • Construction Existing
  • Bedrooms 3
  • Square Feet 1,800

Set on +/-11 acres along a quiet town gravel road is this 1793 historic home, one of the oldest homes in Pawlet. Built for Pvt. Daniel Hulett, who fought in the battle of Saratoga, this center chimney cape was designed for entertaining, with high ceilings, large rooms with wide plank paneling and 3 marble fireplaces (rebuilt central chimney with new liners). Other details include original doors, moldings, and hardware plus a central paneled front door framed by a Federal surround and an intricate denticulated cornice running under the eaves. The house has been partially restored, with much new wiring, new plumbing, septic system, hot water heater, oil tank and electric panel. Also a new tile bathroom and large eat-in kitchen with marble fireplace, cathedral ceilings and small deck - great space! The remainder of the first floor has a formal dining room (or downstairs bedroom) with massive marble fireplace, a spacious living room with marble fireplace and original paneling, a small office/laundry room, and a wing with a studio/workshop space and a spacious mudroom entry. The second floor plumbing is in place with design for two bedrooms and a bath. The location is special, with 11A of open meadow land with a pond site, woodland, a stream, beautiful views from every window, and 80A of protected land across the road (VT Land Trust). Just 3 miles from Pawlet Village- Mettawee School district, school choice 7-12 and fiber optic internet. One of a kind antique gem!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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

229 Antone Mountain View Road Rupert VT 05761
Pending

MLS Number 4961457

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,580

Fantastic "Higher Ground" timber frame barn styled residence on Antone Mountain View just 10 minutes to the Dorset Green located nearby Merck Farmland Center in quiet Rupert Vermont. VIEWS include intense intimate Mountain Views to the South and Southwesterly overlook of Pastoral 12 acres leading to Long Range Mountain Views that pleases the eye from every angle! The hearth of the home centers around a stone fireplace with propane gas insert on the center wall, while the walk-out walls of windows envelope the views. The Kitchen-Great Room soars up toward the Cupola boasting breathtaking structure. The main level primary suite shall not disappoint! The house has been finished in timeless native materials such as honed slate and birch hardwood flooring throughout...all while the mortise and tenon post and beam structure is a marvel! The level features a primary suite while the second level offers 2 bedrooms, an office and loft. Walk out onto the wrap around expansive stone walled terrace which supports indoor/outdoor ease in living! Private Road association. The dry full basement offers height for finishing. This house has always been a second home residence. Appliances and equipment "as is" original 2000. Showings by appointment only. All measurements approx. No Drive By's Please. Private Road and Driveway. Closing must be no earlier than 10/16/23

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

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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$649,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4956609

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

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: 7.19% last updated on Sep 21, 2023
* 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

165 Ebenville Road Rupert VT 05776

Rupert, VT165 Ebenville Road

Price$130,000

Est. Mortgage: $/month

MLS Number 4951139

  • Land
  • Area Rural
  • Acreage 20
  • Utilities None
  • Zoning Residential

Incredible quiet and privacy off a dead-end country road. 20 acres comprised of a south facing meadow, forest land, year round brook, orchards, views and incredible wildlife. Close to Merck Forest and access to an incredible network of snowmobile/hiking trails. A 40' Pilgrim Open Road trailer comes with the property.

Listed by Paul William Carroccio and Marek Kovac of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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

4629 VT Route 30 Pawlet VT 05761

Pawlet, VT4629 VT Route 30

Price$450,000

Est. Mortgage: $/month

MLS Number 4944731

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Square Feet 2,814
  • Bathroom 1

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

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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

2391 Vermont RT 153 Pawlet VT 05775

Pawlet, VT2391 Vermont RT 153

Price$595,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4927864

  • Residential Single Family
  • Construction Existing
  • Bathroom 1
  • Square Feet 720
  • Bedrooms 1

Welcome to Rush Hollow Reserve, a truly unique 400 ACRE, one of a kind property located in southern Vermont close to Manchester, 4.5 hours to NYC, 3.40 hrs to Boston. Rush Hollows offers fresh spring fed streams, ponds and the Indian River which allows for swimming holes and water for the livestock. This lovely 1000 SF post and beam home sits in the midst of valley with long range views to the south towards Mt Equinox. The farm allows for a nearly self sufficient operation with corn and hay harvested on site throughout the seasons. The forests are full of sugar maple groves with 2500 taps and potential for aprox 10,000 taps tp produce the purest Maple Syrup. In addition to the trails cut through the fields, the D & H Rail Trail which runs through the ranch is wonderful for riding horses as well as hiking and biking. Some of the pastures and fields are prepared for future vineyards and have numerous agricultural options. Most of Rush Hollow is in current use and Vermont land trust. 600 Ft Mtn top dominates the property. Large 10,000 SF barn for livestock, 80 stalls/ 6 horse stalls, horse paddock, mile of fencing around pastures. Truly an amazing and rare opportunity in southern Vermont. Come take a look. All measurements are approximate.

Listed by Joseph Cajzer of Josiah Allen Real Estate,Manchester Branch Office

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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

2391 Vermont RT 153 Pawlet VT 05775

Pawlet, VT2391 Vermont RT 153

Price$595,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4927812

  • Land
  • Acreage 400

Welcome to Rush Hollow Reserve, a truly unique, 400 ACRE, one of kind property that rarely becomes available. Rush Hollow offers fresh spring fed streams and the Indian River with hydration for the livestock and swimming holes. Corn and hay are harvested on site allowing for a nearly self sufficient operation, the hills will bloom for three seasons with beautiful flowers and amazing fall foliage with big mountain views looking south down the valley to Mt Equinox. The partially utilized Sugar Bush currently tapped with 2500 taps and possibilities of up to 10,000 taps to produce the pure Vermont Maple Syrup. In addition to the trails cut through the fields, the D & H Rail Trail which runs through the ranch is wonderful for riding horses as well as hiking and biking. Some of the pastures and fields are prepared for future vineyards and have numerous agricultural options. Most of Rush Hollow is in current use and Vermont Land Trust. 600 ft mountain top dominates the property. Currently there is a one bedroom studio home on the property as well a manufactured home. Large 10,000 SF barn for livestock, horse paddocks, mile of fencing around grazing pastures, hunting cabin. Truly an amazing and rare opportunity in Southern Vermont, close to Manchester, 4.5 hours to NYC and 3 .40 hours to Boston. All measurements aprox. Southern VT 400 ACRES AG!

Listed by Joseph Cajzer of Josiah Allen Real Estate,Manchester Branch Office

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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

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: 7.19% last updated on Sep 21, 2023
* 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 2023 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. 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 September 27, 2023 11:53 PM EDT