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

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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! Also available - directly across the road at 1205 Sandgate Road is a converted barn/3 bedroom home on 3+ Acres. A perfect package for the mini brookside farm! 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: 2.96% last updated on May 6, 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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9 School House Road Middletown Springs VT 05757

MLS Number 4859444

  • Land
  • Acreage 1.04
  • Zoning Village

Charming +/- 1.04 acre building lot located in the Village of Middletown Springs. Vermont State approved wastewater design available for 2 bedroom home. Power near building site and a water well that is already drilled. Come and build your dream home in a lovely intimate Vermont town.

Listed by Eric Hier of Northland Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 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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486 Rogers Road Rupert VT 05251

Rupert, VT486 Rogers Road

Price$525,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4857908

  • Residential Single Family
  • Bedrooms 3
  • Bathroom 2
  • Construction Existing
  • Zip 05251

Wonderful Log home with 1990's beautiful addition on 47+ acres. Creek runs right by the home. Hiking trails up behind the house. Barns. Wonderful homestead waiting for the next owner. 5 minutes to the Dorset Green.

Listed by Josiah Allen Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 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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2709 VT Route 153 Pawlet VT 05775

Pawlet, VT2709 VT Route 153

Price$39,500

Est. Mortgage: $/month

MLS Number 4857497

  • Residential Single Family
  • Bedrooms 3
  • Bathroom 2
  • Construction Existing
  • Zip 05775

Incredible opportunity in the heart of West Pawlet! c1890 built 3 bedroom, 1 & 3/4 bath colonial with frontage on the Indian River. Possibilities abound with great high ceilings and light filled space waiting to be renovated. Home needs electrical work, plumbing and heating, flooring, drywall, foundation work, etc and is being sold in as is condition.

Listed by Melissa Genovart of Rhodes Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 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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2772 VT Route 153 Pawlet VT 05775

Pawlet, VT2772 VT Route 153

Price$187,300

Est. Mortgage: $/month

Pending

MLS Number 4852832

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

Nicely renovated village colonial set on a generous almost 1/2 A lot! Nice flat usable yard offering space for a garden, chickens, pets, playing ball and great privacy in the back complete with a fire pit. Also a detached garage with electric and side car port. The spacious house has 4 plus bedrooms, 3 up, 1 down and a separate 22 x 20 in-law suite/efficiency apartment - ideal for Air B&B, or a great entertainment space - complete with its own kitchen and full bath! The first floor of the main house offers an eat-in kitchen with entry laundry/mudroom, a 1/2 bath, a generous living/dining room, and a downstairs bedroom/office with full bath. The three spacious upstairs bedrooms are enhanced by wonderful large arched windows and a huge full bath. Amenities include good usable full basement, all updated wiring, thermopane windows, new high efficiency propane hot water boiler, new electric hot water heater - move right in! Mettawee school pre-k thru 6, choice 7-12 and x-finity high speed internet. Just 20 minutes from Dorset/Manchester area. A great opportunity and value

Listed by Scott Mcchesney of McChesney RE, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 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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1143 North Pawlet Road Pawlet VT 05761

Pawlet, VT1143 North Pawlet Road

Price$549,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4849757

  • Residential Single Family
  • Bedrooms 5
  • Bathroom 2
  • Construction Existing
  • Zip 05761

Incredible 3,000+ SF restored c1890 antique farmhouse. 5 Bedrooms, 2 full baths, walk-up attic and generous living space! Great for entertaining and gatherings with Formal DR, living Rm, spacious family rm with huge entry back porch, side screen porch and rear deck! Gorgeous views over the pond and into the surrounding mountains! Beautiful details throughout - antique wide and narrow board floors, red slate entry hall, tiled baths, gorgeous original woodwork/moldings, built in cabinets, 2 wood stoves with beautiful stone hearths. Nicely remodeled kitchen with granite counters and custom cabinets with walk in pantry/laundry and first floor office. All on 10 Acres of rolling fenced meadowland, huge flat lawn/back yard with large pond, small orchard and mountain views over surrounding protected lands (VT Land Trust)! Incredible outbuildings: 5,000+ SF (partially heated) barn workshop(needs some TLC) with 5 bays - great opportunity for the auto mechanic, car collector or wood worker... other buildings include 2 car garage/barn, greenhouse and 2 story "party/game" barn complete with outdoor Bocce court! A special building A homestead that feels like "home" and perfect for large gatherings. Ideal location just a mile or two south of Lake St Catherine, convenient to Granville, Ny for shopping and 25 minutes to Manchester area. Mettawee School district pre-k to 6, school choice 7-12 and state of the art fiber optic high speed internet! Come home to this beautiful VT farmstead!

Listed by Scott Mcchesney of McChesney RE, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 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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529 Antone Mountain View Road Rupert VT 05768

MLS Number 4848163

  • Residential Single Family
  • Bedrooms 3
  • Bathroom 2
  • Construction Existing
  • Zip 05768

First time to market in 40 years: Architecturally striking 3 bedroom, 2 bath California Contemporary with unobstructed 180 panoramic mountain views. Sunsets are a painter's dream! The surrounding 43 acres offer both meadows and woodlands; streams; waterfalls; picnic spots; and trails for hiking, XC skiing, snowshoeing, and snowmobiling. The interior offers a two-level open floor-plan. The upper level features living, dining, and kitchen with beamed cathedral ceiling and two-story fireplace. Floors are TN distressed redwood and VT slate. The kitchen has elaborate Italian tile, plenty of cabinetry, and an authentic professional butcher block prep island. Two bedrooms have open views and hidden storage areas above closets with a bath in between. Lower level features a large family room with mountain views, a floor-to-ceiling fireplace, another bedroom, full bath, and separate entrance. Outdoor living space includes a large deck, hot tub, and railing seats for guests to enjoy dining and mountain views. In addition, there is an oversized 2-car garage and a shed for summer/winter toys. Land is in two parcels. The larger parcel has separate road frontage, so a few acres can be sold for a building site. Location is excellent: very close to Merck Forest (hiking/skiing) and nearby artistic Dorset/Manchester, yet only 35 miles from Saratoga Spring's famous racetrack/cultural activities & Lake George boating and water sports. Come see one of the most spectacular views anywhere in VT!

Listed by David Halligan of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 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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Zorn Drive Middletown Springs VT 05757

Middletown Springs, VTZorn Drive

Price$100,000

Est. Mortgage: $/month

MLS Number 4847447

  • Land
  • Acreage 50
  • Area Rural
  • Utilities None
  • Zoning none

Idyllic 50 acres in rural Middletown Springs. Mostly wooded sidehill with an enchanting little meadow at the bottom of the hill that would be the view out your front door. Small old pond and views across the valley to high ridges. Easy access from VT Route 140 on a shared gated [to enclose farm animals] right of way with one other owner. Prior soil testing ensures the ability to locate a septic system for a residence. Electricity on the adjacent property with a right of way to connect to install underground electric and phone. The property is enrolled in the VT Current Use Forestry Program to reduce the real estate taxes. Property being sold with the Current Use Tax Program in place and with the purchaser agreeing to cooperate with the seller in a 1031 tax free exchange at the time of sale.

Listed by Jim Watson of Watson Realty & Associates, PLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

1205 Sandgate Road Rupert VT 05776

Rupert, VT1205 Sandgate Road

Price$249,999

Est. Mortgage: $/month

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.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 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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4629 Vermont 30 Route Pawlet VT 05761

Pawlet, VT4629 Vermont 30 Route

Price$425,000

Est. Mortgage: $/month

MLS Number 4845216

  • Residential Single Family
  • Bedrooms 5
  • Bathroom 1
  • Construction Existing
  • Zip 05761

Listed by Josiah Allen Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on May 6, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

5491 VT Route 315 Rupert VT 05776

Rupert, VT5491 VT Route 315

Price$649,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4843731

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

Recently renovated three bedroom farmhouse, cozy one bedroom guest house, and detached garage with 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 all new interior including kitchen and bath remodels, hardwood floors throughout, updated windows, wiring and plumbing. Further interior improvements include a master with master bath and walk in closet, new walls, ceilings and trim-work. Exterior improvements include the new renovated wood deck and covered porch. 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 one bedroom cottage is bright and cheerful, with a cathedral ceiling, exposed beams, private sun deck, and separate driveway access. Come see all the improvements and make the 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: 2.96% last updated on May 6, 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: 2.96% last updated on May 6, 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 May 13, 2021.