Pawlet, Rupert and Middletown Springs VT Real Estate

The rural farming towns of Pawlet, Rupert and Middletown Springs encapsulate the romantic image of Vermont with its rolling hills, cow pastures and friendly residents. The areas small population enjoys a quiet, pleasant lifestyle. The heart of the Mettowee Valley is in Pawlet, a sweeping valley surrounded by beautiful mountains. Middletown Springs lies just east at elevation, with amazing views revealed at every corner. Just south and west of Pawlet is the town of Rupert which borders Dorset and gives residents the easiest access to Manchester and it's surrounding ski resorts.  While all three towns are a great place to live year round, they should also be considered by those looking for a vacation home, due to their close proximity to Manchester, the mountain ski resorts and great hiking trails.

Discover current real estate for sale in Pawlet, Rupert and Middletown Springs VT. 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.

Pawlet, Rupert and Middletown Springs VT Real Estate For Sale

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793 Three Sisters Drive Pawlet VT 05761

Pawlet, VT793 Three Sisters Drive

Price$615,000

Est. Mortgage: $/month

MLS Number 4926253

  • Residential Single Family
  • Bedrooms 4
  • Bathroom 2
  • Construction Existing
  • Zip 05761

James Hilton's definition of Shangri-La was "a remote idyllic hide away." We now offer such a place. Nestled in the hills of Pawlet on +/-64 surveyed acres is this serene paradise abounding with wildlife and natural beauty. You enter on a beautiful winding drive coursing through hardwoods and are immediately drawn by the splendor of this unique and special compound with a large spring fed pond, streams and a waterfall with bridges and walkways, gardens and views. The main log home, 2 bedroom guesthouse, and small bunkhouse are situated to take full advantage of the distant, inspiring views over the Mettawee Valley. The main home has a kitchen with island, bay window (views), cathedral ceiling breakfast nook, a cathedral ceiling living room with wood stove, cathedral ceiling sunroom with marble floor and circular marble terrace overlooking pond, a bedroom and full bath down. Upstairs there is the primary bedroom and bath with cathedral ceiling and sliders to a balcony to take in the views. There is also a 2 story guest house with a large open room with wide plank floors with a wood stove and 1/2 bath on the first level and 2 bedrooms, a full bath and a large cathedral ceiling eat-in kitchen with deck overlooking the pond on the second level. Seldom do we offer a property that captures Vermont's natural beauty to the degree as does this artfully created retreat. The wildlife and total serenity of this magical world have to be seen to be believed!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 5.13% last updated on Aug 18, 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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180 North Road Middletown Springs VT 05757

MLS Number 4925252

  • Residential Single Family
  • Bedrooms 4
  • Bathroom 2
  • Construction Existing
  • Zip 05757

Circa 1850 home with detached two car garage on 9.9 acres of open and wooded land located on a scenic country road in Middletown Springs. Downstairs you will find a spacious kitchen, formal dining room, large living room with fireplace/woodstove insert , bath, laundry room, mud room and enclosed porch to watch deer and sunsets. Upstairs are four bedrooms and a bath. Recent upgrades include replacement window inserts, heat pump and basement insulation. This property is within a 30 minute drive to Lake St. Catherine State Park-Country Club and the Dorset-Manchester area.

Listed by Alan Gombosi of Northland Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 5.13% last updated on Aug 18, 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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526 Beaver Brook Road Pawlet VT 05761-9401

Pawlet, VT526 Beaver Brook Road

Price$450,000

Est. Mortgage: $/month

MLS Number 4921185

  • Residential Single Family
  • Bedrooms 4
  • Bathroom 2
  • Construction Existing
  • Zip 05761-9401

Remarkable views from this 3 bedroom contemporary! Light filled and open living with a wraparound deck to take in the captivating views of the town below and Woodlawn Mountain and Mount Equinox. Brick hearth with a wood stove keeps you warm on the ground floor and a magnificent stone fireplace on the first floor. Minutes from one of Vermont's best country stores and two restaurants. Add your own touches to make this an enchanting place to call home.

Listed by Josiah Allen Real Estate,Manchester Branch Office

$
$
%
$/month over payments
Federal 30-year interest rate: 5.13% last updated on Aug 18, 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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119 Dayton Hill Road Middletown Springs VT 05757
Pending

MLS Number 4920607

  • Residential Single Family
  • Bathroom 1
  • Construction Existing
  • Zip 05757

With a small waterfall murmuring in the background this rustic getaway is just waiting for you. This stream-side seasonal cabin is set at the end of a dead end town road with water piped down from a hillside spring (there is also a drilled well), an existing septic system with a 1000 gallon tank, and power and internet at the adjacent property. A new shed provides additional storage space. Add a little elbow grease and a wood stove for ambiance to make this the perfect Vermont getaway. The road continues as a Class 4 road (not maintained and not passable by most trucks even, but usable by ATV or mountain bike, and connects through to the incredible mountain bike trail system of Slate Valley Trails.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 5.13% last updated on Aug 18, 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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155 School Street Pawlet VT 05761

Pawlet, VT155 School Street

Price$349,000

Est. Mortgage: $/month

Open House

MLS Number 4918530

  • Residential Single Family
  • Next Open House: Sat 08/20 4:00 pm. to 7:00 pm.
  • Bedrooms 3
  • Bathroom 2
  • Construction Existing

Historical colonial home that has been lovingly restored with river frontage in the heart of Pawlet village. The current owner has been featured on Restoration Road on the Magnolia Network and created a historically accurate replica 1800's tavern for entertaining. Many updates done including, opening the floorplan, new second floor bathroom, exterior paint, with a sump pump and vapor barrier added in basement. First floor has formal entry, living room, updated full bathroom, dining and kitchen with office space and den with lofted ceiling and cozy brick hearth. Oil fueled boiler baseboard heat can be supplemented with wood stove insert or pellet stove. Second level features three bedrooms with an open space between, shared bathroom and a small loft. This half acre nestled next to the Pawlet Public Library and protected public lands has a shady outdoor patio framed with lilacs from Robert Frost's residence in Bennington, a chicken coop, a veggie garden and wide open lawn that abuts the Metawee River. Centrally located, The Station, Mach's Market, The Barn, the post office and town office are located within 3 tenths of a mile. Less than 15 miles to the conveniences of Manchester. School choice for grades 7 through 12.

Listed by Andie Fusco of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.13% last updated on Aug 18, 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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1 North Street Middletown Springs VT 05757

MLS Number 4916231

  • Residential Single Family
  • Bedrooms 3
  • Bathroom 2
  • Construction Existing
  • Zip 05757

Walk into another time and place and just relax in this beautiful historic home! Wonderfully landscaped, spacious rooms looking out onto the lovely garden area with a private backyard make this a perfect retreat or fulltime residence for you to enjoy! The home is complete with pristine period details including formal entry hallway, high ceilings, large windows, original wood floors and French doors leading into elegant rooms. Feel rejuvenated on the shaded porch with mahogany wood flooring and listen to the birdsong! The home features space for 3 bedrooms, 2 full bathrooms, with modern kitchen with indoor grill, dining room, living room, sitting room, office and or space for a pantry. The brick from the home was actually made from the earth right on property!! And they used to smoke hams in the basement!! A true piece of Vermont History!!

Listed by Bonnie Chandler of RE/MAX Four Seasons

$
$
%
$/month over payments
Federal 30-year interest rate: 5.13% last updated on Aug 18, 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

Pending

MLS Number 4912861

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

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: 5.13% last updated on Aug 18, 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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3632 Route 153 Pawlet VT 05775

Pawlet, VT3632 Route 153

Price$147,500

Est. Mortgage: $/month

Pending

MLS Number 4913050

  • Residential Single Family
  • Bedrooms 4
  • Bathroom 1
  • Construction Existing
  • Zip 05775

Edge of the Village Homestead- Nicely located on the outskirts of the village of West Pawlet is this spacious Old homestead set on a generous 3/4A village lot - lots of space for gardening etc. Much has been done over the years including vinyl siding, newly built furnace chimney, A newer shed outbuilding, in addition to an older shed, and most recent renovations in the house which include the gutting of the living room area and installation of tongue and groove pine(mostly completed). A very spacious home with 4 or more bedrooms upstairs, and an eat-in kitchen, large full bath/laundry, and the large living room (not completed) with wood stove downstairs. Other details include An almost full basement (5ft crawl space), a great walk up attic, and the attached drive thru heated garage housing the oil baseboard hot water boiler and fuel tank. A beautiful yard, great open space for gardening and critters with ample shed space. High speed Comcast xfinity internet and Mettawee School district pre-k thru 6th with school choice 7-12 A solid value at 147,500

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

$
$
%
$/month over payments
Federal 30-year interest rate: 5.13% last updated on Aug 18, 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 4911216

  • Residential Single Family
  • Bedrooms 3
  • Bathroom 2
  • Construction Existing
  • Zip 05761

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 Josiah Allen Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 5.13% last updated on Aug 18, 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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989 Herrick Brook Road Pawlet VT 05761

Pawlet, VT989 Herrick Brook Road

Price$319,500

Est. Mortgage: $/month

Pending

MLS Number 4911236

  • Residential Single Family
  • Bedrooms 4
  • Bathroom 2
  • Construction Existing
  • Zip 05761

Brookside Haven - The soothing murmur of the brook is the backdrop for this spacious contemporary home with its secluded waterside deck running the full length of the house. The slate floor sunroom invites the outdoors in, while the pellet stove, baseboard hot water heating system, with optional pellet stove, marble fireplace, and additional wood stove hook-up keep the house cozy and warm. A long central balcony overlooking the living room provides both an open feeling and second floor water views. Multiple bedrooms and a full bath on each level, and a two car garage provide plenty of space for people and vehicles. The room with the marble fireplace can continue as a formal dining room or convert easily to a home office or library. Outside, established gardens, fruit trees, and stately red maples create a classic rural Vermont homestead. A whole house standby generator, blazing fast fiber optic internet, and an efficient pellet stove ensure 21st century comfort. This is a private location set back from Herrick Brook Road while being convenient to Manchester, Dorset, Ski Areas and the lakes. School choice grades 7-12.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 5.13% last updated on Aug 18, 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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1292 State Route 149 Pawlet VT 05775

Pawlet, VT1292 State Route 149

Price$185,000

Est. Mortgage: $/month

Pending

MLS Number 4910471

  • Residential Single Family
  • Bedrooms 5
  • Bathroom 2
  • Construction Existing
  • Zip 05775

This home has been in this family since 1960. It has been used as a one family home since 1972, even though it has a 2nd kitchen and other rooms that could be used for separate living quarters. It has an interior stairway as well as a 2nd one that leads to outside from the 2nd level. This spacious home sits right on the NY/VT border. 2 car detached garage in back. Driveway is owned by these people, but the neighbor has a ROW across it and therefore the driveway can't be blocked by anyone. Take a look at the photos to get a better idea of the set up. Soonest Occupancy is currently October 15. This may be able to be changed if their new house gets finished sooner.

Listed by Rebecca Dittmeier of Country Horizon Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 5.13% last updated on Aug 18, 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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5932 VT Route 153 Rupert VT 05768

Rupert, VT5932 VT Route 153

Price$229,500

Est. Mortgage: $/month

MLS Number 4909605

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

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: 5.13% last updated on Aug 18, 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

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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 August 20, 2022 2:08 AM EDT.