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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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: 2.97% last updated on Feb 25, 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: 2.97% last updated on Feb 25, 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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1205 Sandgate Road Rupert VT 05776

Rupert, VT1205 Sandgate Road

Price$265,000

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 $265,000. 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 $319,000, 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: 2.97% last updated on Feb 25, 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 Charles Mauro of Josiah Allen Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 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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5491 VT Route 315 Rupert VT 05776

Rupert, VT5491 VT Route 315

Price$649,000

Est. Mortgage: $/month

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: 2.97% last updated on Feb 25, 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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729 Coy Hill Road Middletown Springs VT 05757
Active With Contract

MLS Number 4842647

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

This spacious log home welcomes you into a sun filled great room with both a central fireplace and a separate wood stove with hearth. The massive cathedral ceiling timbers continue into the large dining room encompassing the open plan kitchen with walk-in pantry. Twin sliding glass doors to the rear deck bring in the natural light and mountain views. One wing comprises three bedrooms and two full baths while finished rooms in the basement provide plenty of space for a family room, overnight guests, and a home office. A spacious two car garage under the house keeps your vehicles free of snow and ice. Enjoy the bounty from the back yard fruit trees and berry bushes, and stroll down to the year round brook for a peaceful retreat. Acres of mixed hardwoods will provide plenty of firewood, walking or hunting. This inviting home is located along a quiet town maintained gravel road just a few minutes outside the quaint village of Middletown Springs. Convenient twenty minute drive to Rutland, Castleton, Poultney, and Lake St. Catherine State Park. Nearby ski and recreation areas include Killington, Pico, Bromley, and Stratton.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 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: 2.97% last updated on Feb 25, 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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595 Antone Mountain View Road Rupert VT 05768

MLS Number 4841825

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

Amazing Taconic Range Views and lovely setting away from it all yet convenient to Dorset/Manchester amenities WOW! An artistically presented contemporary that offers warmth, ease and one level living. This second home residence offers a natural low maintenance wooden exterior, grounds and a gazebo over looking pond. A separate detached 40x34 (3) car garage/barn/workshop with potential for upstairs renovation included kerosene heating for an office space. Kitchen great room is 26' X 27' with stainless appliances, slate floor that is open to the living/dining with a substantial VIEW! All living walks out onto expansive wrap around decking. Wood stove for those cozy nights in. Primary suite has a great view and tile bath ... a separate guest wing offers two bedrooms with bath. Some additional clearing shall expand the views. The private road is worth the assent up to this private perch. This residence is sited at the very top of Anton Mountain View which is a steep climb. The rewards: a second home sanctuary overlooking the areas finest SUNSETS!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 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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2771 VT 153 South Route Pawlet VT 05775

Pawlet, VT2771 VT 153 South Route

Price$85,000

Est. Mortgage: $/month

Pending

MLS Number 4840868

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

Great opportunity for the handy person! Great bones - high ceilings, some original moldings, wood floors, double parlor upstairs for master bedroom, and downstairs for generous living space(currently being used as bedrooms) - beautiful original Large sliding pocket doors. House has been rewired, newer oil boiler, updated kitchen and updated baths - downstairs complete with laundry(newer Washer and Dryer, electric stove and refrigerator). Great 2 story carriage barn/garage, workshop and private back yard with frontage on the Indian River!

Listed by Scott Mcchesney of McChesney RE, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 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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682 VT 30 Route Rupert VT 05768

Rupert, VT682 VT 30 Route

Price$199,900

Est. Mortgage: $/month

MLS Number 4839141

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

A 4 bedroom, 1.5 bath c.1900 Post Beam cape located in Rupert, Vermont. A large covered back porch overlooks the beautiful level 1.10 +/- acre tree lined lot where sounds of the Hager Brook can be enjoyed. The charming 19' beamed living room features a wood stove, bringing ambiance and warmth into the room. The 17' country eat in kitchen has a great south facing window and opens into the walk in pantry. The convenient first floor master bedroom is 12'x23' and sports a half bath. A new stainless steel liner installed in chimney 2011. A great back yard with plenty of room for gardening, pets, children's play, barbecuing or just relaxing. Small garage or large storage shed.

Listed by Lori Winn of New England Lakeside Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 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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227 Garron Road Middletown Springs VT 05757
Active With Contract

MLS Number 4837863

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

Tucked back off the road is this very special turn-key home sited in a private and peaceful ten acre setting with views and easy access from a town maintained country road. Located just outside of the picturesque village of Middletown Springs, Vermont with nearby lakes, rivers and mountains offering plenty of outdoor recreational opportunities including fishing, hiking, biking, horseback riding, water sports, hunting and nearby skiing at Killington and Pico mountains. Open floor plan with plenty of natural light includes a great room offering a cozy woodstove and built ins, dining area and kitchen. Beautiful pine wood floors throughout, three bedrooms and two full baths. Lovely deck to enjoy the mountain views and listen to the birds sing and a shed in the back great for storing lawn and garden equipment. Great work at home office package includes cell service, high speed fiber optic internet access, updated security cameras as well as whole house generator keeping you automatically connected. Stay warm with 2 zone heat and Buderus boiler. Minutes to village center for Sissy's Kitchen and Grant's General Store. Thirty minute drive to Manchester, Dorset and Rutland areas and only fifteen minutes to Poultney for a quick bite to eat and hardware store, groceries and pharmacy. Escape the big city and come thrive in this small quintessential Vermont town in a wonderful neighborhood and enjoy all Vermont has to offer. All measurements are approximate.

Listed by Chris DeFelice of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 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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3923 Kent Hollow Road Rupert VT 05776

Rupert, VT3923 Kent Hollow Road

Price$279,900

Est. Mortgage: $/month

MLS Number 4835486

  • Residential Single Family
  • Bedrooms 1
  • Bathroom 1
  • Construction Existing
  • Zip 05776

Incredible surveyed 31.5 acre lot with long road frontage, beautiful open hidden fields protected by wood line perimeters would offer numerous options to build your new home or a perfect spot for a family retreat. An adorable A frame awaits the new buyer and has had recent renovations as late as 2011 and would be a perfect weekend get away or a place to stay while building your new dream home. The property also has a detached 2 car garage with additional attached room, offering a perfect conversion for your animals. The property is easy to walk, has a small pond, and beautiful mountain vistas grace the property. One of Vermont's prettiest spots and in a great recreational area as you will find the D & H bike trail in the center of Rupert and the Merck Forest hiking trails that are approximately 1.5 miles from this property. If you are looking for additional property, then the opportunity to buy an additional 191.5 across the street is possible. Let your dreams begin. Currently in land use but with the right offer seller would entertain removing. Property shares the water with the house across the street along with power but can easily be deeded or changed.

Listed by Hughes Group Team of Casella Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 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 February 25, 2021.