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.

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520 South Street Middletown Springs VT 05757

Price$2,950,000

Est. Mortgage: $/month

MLS Number 4771241

  • Residential Single Family
  • Bedrooms 7
  • Bathroom 7
  • Construction Existing
  • Zip 05757

Its name is Legendary. Its Reputation Renowned. Situated on 573 private acres Honey Pond Farm is a one of a kind recreational retreat. It features an unconventional USGA rated Golf Course written up in Links and Stratton Magazines and has hosted many Charity Events, Celebrations and Invitational and Pro-Am Tournaments.The course is comprised of 3 Greens, multiple Fairways and 26 tees surrounding a 25 acre area played as 18 holes, including a 584 yd. par 5 teed from a Cornfield.This Unique Country Playground features a Tennis Court, Bocce Court and 10+ miles of Hiking, Riding and Hunting trails leading to a Mountain Top Vista and Camp Site with Breathtaking views of the Adirondacks, Killington, Pico & Lake George area. Formerly a 1786 New England Tavern, the 7000 +- SF completely renovated home boasts 7 Bedrooms (attached guest house), 6½ Baths, a Wine Cellar, Full Gym,Gameroom w/Pool Table and Bar, 4 Car Garage and expansive Decks with Panoramic views. Several outbuildings dot the property, including a CaddyShack w/Party Deck. Possibilities of ownership include use as a year round Family or Corporate Retreat,a High-end summer Golf Camp, exclusive Air BnB experience,or combination thereof. Its located near the classically charming Middletown Springs village & roughly 20 Minutes from Dorset, 30 from Manchester & 45 Killington/Okemo/Stratton. Arrange a tour to see this property including an ATV ride up to the Mountain Top Vista & Camp Site (2,300 elv) with 180 degree WOW views.

Listed by Steven Bryant of Josiah Allen Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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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864 Rogers Road Rupert VT 05251

Price$2,400,000

Est. Mortgage: $/month

MLS Number 4771007

  • Residential Single Family
  • Bedrooms 4
  • Bathroom 6
  • Construction Existing
  • Zip 05251

Magnificent Country Estate property with privacy and views. Perfectly sited close to the town of Dorset and at the end of a town maintained road to capture views of the Mettowee Valley and Green Mountain National Forest. Many well maintained trails traverse the 50 acres going up to Spruce Peak. A two acre pond is surrounded by pristine fenced pasturelands. Beautifully landscaped gardens, attached barn, outdoor fireplace and covered porch are just some of the features offered. Property is managed for high quality timber production with a current standing timber value roughly at 1.2M. Also being offered with 642 acres and guest house.

Listed by Andy Reed and Elena Atwill of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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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168 South Street Middletown Springs VT 05757

MLS Number 4770731

  • Land
  • Acreage 20.38
  • Zoning ARR

The perfect parcel... 20 surveyed acres- 2/3 open, rolling meadowland, a year round brook and the balance in mature woodland. Great road frontage/access and pretty valley and mountain views. A special piece of Vermont!

Listed by Scott Mcchesney of Lee D. McChesney RE, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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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36 Prospect Lane Middletown Springs VT 05757
Open House

MLS Number 4770617

  • Residential Single Family
  • Next Open House: Sat 7th 10:00 am - 12:00 pm
  • Bedrooms 4
  • Bathroom 3
  • Construction Existing

Unique and private country charm surrounded by mother nature on all sides with picturesque mountain views from every room. The large windows allow natural lighting to flow in and bathes its open concept with warmth and charm in all three levels. Front and back covered porches to relax and take in the beautiful views. Custom built with quality materials such as solid wood doors, wood trim, granite counter tops in the kitchen and bathrooms, granite window sills in living room and dining room, tongue and groove cathedral ceiling in living room and master bedroom, exterior has concrete siding. Main level offers open concept with hardwood floors in the kitchen, dining and living room, two bedrooms and full bath with steam shower. Upper level opens to a loft/office space overlooking the living room and master bedroom suite, full bath with Jacuzzi tub and separate shower, lower level has walk in entry to living/workout area, doggy room that could be used as a bedroom, den and ½ bath. Doggy room has doggy door to exterior fenced in area. House is wired for standby generator. All of this situated on 14.24 acres with a new 24' x 36' 2 car garage/barn. Located minutes from Middletown Springs center where you can dine at Sissy's or shop at Grant's Village Store, nearby is Tinmouth Channel Wildlife and White Rocks National Recreation Area. Enjoy the private trails to the river and come see for yourself what it would be like to experience nature from the comfort of your own home.

Listed by Debra Bennett of Alison McCullough Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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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5251 Suncrest Rupert VT 05768

Price$299,000

Est. Mortgage: $/month

MLS Number 4769958

  • Land
  • Acreage 122.12
  • Zoning Rural

Extraordinary122 acre +/- land parcel with views, pastures, hayfields, stream, woodlands and multiple house sites with septic design and permits. This rare parcel is just 10 minutes to Dorset Green, yet a world away with privacy, peaceful location and a wonderful Vermont setting. Newly built driveway entry and culverts. Current owners have worked with USDA to improve wild life habitat and maintain apple orchard and hayfields. This special parcel offers a mix of pastures, orchards and woodland with timber. Opportunity abounds whether for equine, estate living with 4 house sites, agricultural, sugaring or timber. Simply a most exceptional opportunity to create and enjoy your Vermont country experience.

Listed by Kim Morgan-Wohler of Wohler Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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 4768922

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

Established in 1972 from a once cow barn, this impressive +/-5,000SF Timberframe restaurant has grown into a thriving business and destination. The unique and ideally configured 140+ seat restaurant lends itself beautifully to large and/or smaller private parties/gatherings with 4 separate spaces. 1) Main (60 seat/1,000SF) dining room with soaring cathedral ceilings, a massive stone fireplace and huge windows looking down the Mettowee Valley. 2) Loft (open to main dining room - 400SF/40 seats) 3) 45 seat/1,000SF Tavern with stone fireplace, performance platform for live music and 4)Seasonal 30 seat/360SF porch accessed from tavern with steps to lawn/garden area and views down the Mettowee Valley. The current owners/operators have made many substantial improvements/additions over their 20+ years of ownership. Including but not limited to new heating system + 5 split unit heat/AC pumps, new engineered/state approved septic, kitchen addition (over 600SF kitchen space), 130SF walk-in cooler space, and all new/updated well maintained equipment and fixtures. All in all an architecturally/aesthetically pleasing and mechanically impressive property. The business is impressive with strong figures and continued growth. Grossing close to $1,000,000 and serving over 30,000 meals in the last year - and current first quarter is up in both meals served and gross income by over 15% and in the last 10 years the business/revenue has grown by over 80%!

Listed by Scott Mcchesney of Lee D. McChesney RE, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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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115 Main Street Rupert VT 05776

Price$235,000

Est. Mortgage: $/month

MLS Number 4768556

  • Residential Single Family
  • Bathroom 2
  • Construction Existing
  • Zip 05776

Amazing opportunity! Commercially zoned Antique Center formally the J.H. Gould Company, this has serious potential. Live in the charming, one bedroom one bath cottage and renovate the front building into residential space for Rental income or set up shop and sell antiques ..... or anything else - live the good life in Vermont! Wonderful retail/craftsperson studio workspace. Open floor plan waiting for the next owner with a vision! Spring fed Pond out back is shared with the neighbor. Garage and Workshop for the Carpenter or Car enthusiast. . Cozy Cottage. Come take a look!

Listed by David Shehadi and Jennifer Redding of Josiah Allen Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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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3502 Vermont Rte 153 Pawlet VT 05775

Price$95,000

Est. Mortgage: $/month

MLS Number 4767600

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

Just outside the village of West Pawlet is this c1900 3 bedroom, 2 full bath neat and tidy home. Well maintained with a new rear deck overlooking the spacious and private back yard with 2 shed/outbuildings and even a fire pit tucked against the rear tree line. The home has a large kitchen with tile floors open to a dining room and living room with nice original hardwood floors and a wood stove with beautiful brick hearth and surround. Completing the downstairs is a bedroom or office, full bath, laundry/mudroom and great entry/front porch. Upstairs has 2 more bedrooms and a generous full bath with tile floors. Mettawee school district and school choice for grades 7-12. A great starter home and value at $95,000

Listed by Scott Mcchesney of Lee D. McChesney RE, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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 Watrous Road Rupert VT 05776

Price$267,800

Est. Mortgage: $/month

Pending

MLS Number 4767003

  • Residential Single Family
  • Bedrooms 2
  • Bathroom 2
  • Construction Existing
  • Zip 05776

This classic log home equally well suited as an idyllic vacation retreat or a comfortable year round residence! The property is located minutes from the Dorset Green, on a lovely well-maintained town road. The property is on 10.7 pristine private acres with Merck Forest on two sides. There are landscaped grounds, trails, stonewalls, mountain streams, well-established perennial flower gardens that bloom profusely through the summer and fall. The setting is idyllic. The home is meticulously maintained with a Hearthstone soapstone wood-stove anchoring the living room which opens to the dining area off the kitchen. The home offers one bedroom on each level and a large open loft upstairs perfect for office/studio/guests. Master bedroom includes vaulted ceiling and a wood-burning fireplace. Lovely screened porch at the front of the house to relax and take in the sounds of the brook. Large patio at back of house is an ideal place for BBQ's with friends and family. Large detached oversize garage with finished room upstairs. Classic two story Vermont red barn offers more storage and parking. Woodshed next to house. Two garden sheds with additional woodshed. Wooded acreage and trails offer plenty of opportunity to cross-country ski, snowshoe, mountain bike, hike and bird watch. This beautiful property is the ideal home for all seasons. All measurements approximate.

Listed by Tatsiana Clark of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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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318 Antone Mountain View Rupert VT 05768

Price$389,000

Est. Mortgage: $/month

MLS Number 4765057

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

Incredible mountain views, total privacy on 10 acres off a dead-end private road, and a great Rupert location just 5 miles to Dorset/40 minutes to Saratoga and almost adjacent to Merck Forest. A spacious 4 bedroom, 3 1/2 bath, 3,000+ sq ft home - impeccably maintained and beautifully designed to capture the views! Great space to spread out with family or house guests and set up nicely for single floor living with a new master bedroom wing on the first level and attached 2 car garage. Come enjoy cathedral ceilings, marble fireplace, new kitchen, sunroom, and stone terrace - hear the quiet and watch the sunset over the surrounding mountains! Mettawee School District- school choice- an incredible value and property!

Listed by Scott Mcchesney of Lee D. McChesney RE, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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

Price$2,400,000

Est. Mortgage: $/month

MLS Number 4764906

  • Residential Single Family
  • Bedrooms 4
  • Bathroom 3
  • Construction Existing
  • Zip 05761

This is the quintessential Vermont horse property located minutes from the Dorset green. The farm has it all: 33 acres of lush pastures, a swimming pond, brook and woodlands that run up to the edge of the property. Fantastic views of nearby mountains and Sykes Hollow. A classic horse barn with groom's apartment, 7 stalls, wash stall with heat lamps, heated tack room with washer and dryer in the grain room/work area. The hayloft has ample space for full loads of hay and shavings. Numerous sheds and outbuildings and a 2012 70 x 144 heated indoor riding arena with travel right footing. 100 x 200 outdoor ring with travel right footing. Derby field with ditch and bank. There are 2 over sized turn out fields, 2 large turn out fields... all with dry paddocks and run in sheds. 3 additional large turn out fields and 3 sand paddocks. The main 4 bedroom farmhouse was completely renovated in 2011. In addition to the main house there is a charming attached 2 bedroom guest house, which currently provides rental income. Sykes Hollow Road is right off of route 30 for easy access to Dorset, Manchester and Saratoga and all they have to offer. If you want to own and enjoy a classic Vermont horse farm property on 33 acres, this is one you need to see. Shown by appointment only. All measurements are approximate.

Listed by Tatsiana Clark of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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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57 Ike Wright Road Trail Rupert VT 05768

Price$495,000

Est. Mortgage: $/month

MLS Number 4763750

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

Built in 2005 with large addition added in 2017 this home in the country is picturesque! This 162 acre property features meadows, a pond, indian river, rail trail access and woods abundant in wildlife. Views of Mt. Antone from the master bedroom and side porch! Living room with cathedral ceiling, granite counter tops, custom tile master bath! This cozy home is close to Manchester and a short drive to Stratton, Bromley and Magic Mountain! A true Vermont paradise for nature lovers or those looking for peace and serenity!

Listed by Jason Saphire of www.EntryOnly.com

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 2019
* 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 2019 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 25, 2019.