Properties Over 20 Acres

Below you will find all properties in southern Vermont that include more than 20 acres of land. Contact us if you have any questions or if you would like to schedule a showing. Create an account to save your favorite properties and to receive email notifications when similar properties become available. 

1048 Black Hole Hollow Road Arlington VT 05250

MLS Number 4502293

  • Residential Single Family
  • Bedrooms 8
  • Bathroom 7
  • Construction Existing
  • Zip 05250

The serene setting of Black Hole Hollow Farm in a quiet valley on the border of Vermont and New York is threaded by the White Creek brook, tiered ponds and 30 miles of trails on 948 acres. The 6-bedroom, 8,143-square-foot main house is surrounded by English-style country gardens with the mountains as backdrop. The original 1772 farmhouse was expanded and designed by noted architect Jerome Cerny. Living room, dining room and downstairs bedrooms open to the gardens and the recently updated kitchen is a welcoming hub with its AGA stove. The farm has a rich history including visits from author Ian Fleming who gained inspiration for several of his James Bond books, and former owner Josephine Hartford Bryce, heir to the A&P dynasty. There is a large greenhouse with sitting area and Koi pond. Other buildings include 4 additional residences, a 2-bedroom apartment, horse & hay barns and a sugar house. Only 7 miles from Cambridge, NY, 30 miles to Saratoga, and 26 miles to Bennington, VT.

Listed by T Story Jenks of LandVest, Inc/Woodstock

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$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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$3,600,000

Est. Mortgage: $/month

MLS Number 4496096

  • 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 642 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 also has separate guest house and caretaker quarters. Property is managed for high quality timber production with a current Standing timber value at 1.2M.

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

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$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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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466 Marcia Lane Dorset VT 05251

Price$3,500,000

Est. Mortgage: $/month

MLS Number 4744398

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

Dorset Hollow Pinnacle offering 180 trail laced acres at the height of the Dorset's Upper Hollow Road. Amazing Sunset Color... Stunning Long Range Mountain Vista's are captured immediately from the impressive foyer and continues to captivate from room to room throughout this architect designed residence! With over 7500 light filled square feet this gracious residence with lovely custom cabinetry and crown moldings supports Vermont living at it's finest! Massive Stone fireplace walls grace the cherry paneled library as well as the 50 X 22 expansive Great Room Kitchen featuring an incredible breakfast room and a Honed Costa Esmeralda island, Wolf appliances and handsome coffer ceiling for the living/dining. Just off the kitchen are the well planned wet bar, wine cellar and pantries. Warm radiant heated hardwood floors lead to the 3 room primary suite that includes sitting rm/office, exercise room and luxury bath with relaxing soaking tub and shower. Four bedrooms and baths up comfortably accommodate guests and family. The bonus room integrates nicely for full time use supporting any hobby or media interest. Full light filled basement and Carriage house offers expansion for guest quarters within the generous floor plan if desired. Over-sized garages either attached or detached offer room for all the toys! Raised stone terrace creates indoor / outdoor ease for all living areas that offers heated path to the spa and grilling area. This property meets field and stream perfection!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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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1420-1424 West Road Manchester VT 05255

Price$3,500,000

Est. Mortgage: $/month

MLS Number 4769327

  • Residential Single Family
  • Bedrooms 5
  • Bathroom 5
  • Construction Existing
  • Zip 05255

Perched on a hillside with outstanding panoramic Green Mountain and Equinox views. This contemporary residence and guesthouse are exceptional in every way. Custom crafted with native stone and clapboard, the exterior of the home hints to the quality found throughout. Large windows, custom mill work, vaulted ceilings, and oak floors highlight the interior. The handsome two-story entrance opens to the dining room, great room with stone fireplace and a cooks kitchen with custom cabinets and stainless appliances and stone tops. The first-floor master suite, additional bedroom suite, and handsome den with custom cabinets counterbalance the public areas. Two additional large bedroom suites complete the second floor. A separate guest house built in 2015 includes two-bedroom suites and an attached four-car garage. A large 4 car over-sized equipment garage and basketball court complete the property. Stone walls, terraces, and screened porches are complemented by perennial gardens and plantings.

Listed by Moira Spivey of Four Seasons Sotheby's Int'l Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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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415 Uphill Lane Dorset VT 05251

Price$2,950,000

Est. Mortgage: $/month

MLS Number 4761453

  • Residential Single Family
  • Bedrooms 8
  • Bathroom 8
  • Construction Existing
  • Zip 05251

A simply outstanding opportunity, this private, 47 acre Country Estate with a 11,000 SF Colonial residence, a three-bedroom guest house, a four-car garage with caretaker's apartment, equipment barn, swimming pool and two build-able lots is now offered at less than 30% if its original construction cost. With expansive living spaces, a three-floor elevator, 9 fireplaces, a true cook's kitchen with hand painted cabinets and stone tops, a media room and library with custom butternut cabinetry, elegant bedroom suites and outdoor spaces that include a screened porch, stone terraces and covered porches that flank the view side, the additional amenities include a 2 bath pool house, large dog run, greenhouse, formal gardens, 2-story barn and a 3-car carport and generator room. Highlighted by exquisite landscaping in the heart of Southern Vermont, equidistant from NYC and Boston, Birchmeadow is perfect for use as a family compound or multi-generational gathering place.

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

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$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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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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.Unique Country Playground features a Tennis Court, Bocce Court and 10+ miles of Hiking, Riding, pastures and 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.

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$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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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905 Dawley Road Mount Holly VT 05758

Price$2,900,000

Est. Mortgage: $/month

MLS Number 4395912

  • Residential Single Family
  • Bedrooms 3
  • Bathroom 3
  • Construction Existing
  • Zip 05758

On the National Register of Historic Places, this home provides a retreat on over 300 acres of land with its own pond and hiking trails. Unique design giving a prime example of mid-twentieth century International style. Built mostly of cement offering 3 bedrooms, 3 baths and living areas designed to incorporate nature into your home. A special home for that special Buyer! Note: Property in Vt. Land Use, Subject to: Protective Covenants, Velco Power Line Easement, & Class 4 roadway. Aprox. 9.9 acres in Town of Shrewsbury.

Listed by Frank Ellison of Coldwell Banker LIFESTYLES - Ludlow

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$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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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904 Reilly Road Londonderry VT 05148

Price$2,850,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4762997

  • Residential Single Family
  • Bedrooms 8
  • Bathroom 8
  • Construction Existing
  • Zip 05148

The romance of a classic Vermont farmstead with all modern conveniences - Maple Tree Farm evokes the pastoral calm of old Vermont with a beautiful 1996 reimagination of a white clapboard farmhouse in a 92- acre setting of fenced meadows, towering pines, and a pond. Privacy, views, close to major ski areas and restaurants, post and beam barns and equestrian amenities: ten stalls, indoor riding arena, and a newly renovated three-bedroom apartment. The 7,700-square-foot, 8-bedroom main house is open and bright with high ceilings, wide pine floors and beautiful detail.

Listed by T Story Jenks and Dia Jenks of LandVest, Inc/Woodstock

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$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

636 Fowler Brook Road Mount Holly VT 05758

Price$2,850,000

Est. Mortgage: $/month

MLS Number 4748940

  • Residential Single Family
  • Bedrooms 5
  • Bathroom 7
  • Construction Existing
  • Zip 05758

Spectacular compound/estate property privately situated on approximately 216 acres with sweeping long-range mountain views. The land component is comprised of 20-30 acres of open pasture, a gorgeous swimming pond below the house, beautiful landscaping, and seemingly endless trails for riding and recreation. The 8,169 s.f. main residence - perfectly sited on a knoll overlooking the compound - was custom-built by the present owners and features a fabulous vaulted ceiling great room with massive stone fireplace, a large, fully outfitted gourmet kitchen that opens to a wrap-around porch leading down to the 51 foot in-ground heated swimming pool & hot tub. All 5 bedrooms have ensuite baths. Additionally, there are two well-maintained guest houses on the property, one with 4 bedrooms and 2 baths and the other with 2 bedrooms and 2 baths. Mechanicals are top-flight with whole house air conditioning, radiant heat, two propane backup generators and multiple drilled wells. Chance Hill Farm is currently setup for a variety of equestrian uses with a regulation size outdoor riding arena, a well-built 10-stall horse barn, two run-in sheds and a storage barn for a tractor and storage of other motorized toys. Horse riding/hiking/biking trails weave throughout the property. The property is conveniently located within 10-20 minutes of Okemo/Ludlow, Rutland, Rutland Southern Vermont Regional Airport (RUT) and Weston, and just 50 minutes from the Village of Woodstock.

Listed by John Snyder of Snyder Donegan Real Estate Group

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$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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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4263 Main Street Manchester VT 05254

Price$2,750,000

Est. Mortgage: $/month

MLS Number 4766421

  • Residential Single Family
  • Bedrooms 4
  • Bathroom 6
  • Construction Existing
  • Zip 05254

Glebelands is an extraordinary estate property hidden away in the center of Manchester Village.i A private circa 1900's colonial main house with multiple outbuildings, 2 apartments, 4 garages, trails and more. Set back on +/-28.5 private acres with 2 ponds including a waterfall on Munson Brook- Incredible private setting! Formal gardens, specimen plantings and trees/orchard throughout the property. The main house has 4 bedrooms, 6 bathrooms, great room, 1st floor master suite, library all with beautiful original details. A great village location and incredible opportunity. First time on the market in 35 years!

Listed by Eric Nathan of Nathan Auction & Real Estate Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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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Birdseye Castleton VT 05777

Price$2,699,995

Est. Mortgage: $/month

MLS Number 4776416

  • Land
  • Acreage 607.34
  • Zoning None

Now is your chance to own this pristine property on 600+ acres - formerly the Birdseye Ski Resort! This property is perfect for back-country enthusiast such as skiers, hikers and mountain bikers, hunters and more. Castleton River access, great location.

Listed by Tucker Adirondack Lange and Hergenrother Realty Group of KW Vermont

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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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474 Horton Road Londonderry VT 05155

Price$2,495,000

Est. Mortgage: $/month

MLS Number 4764745

  • Residential Single Family
  • Bedrooms 6
  • Bathroom 8
  • Construction Existing
  • Zip 05155

Newly priced-Hidden Meadows is a magnificent mountain estate nestled on 90 acres in the heart of ski country with views, meadows, ponds, beautiful stonewalls, woodlands & miles of trails for your outdoor enthusiast.The property exudes world class amenities: pool & open air pavilion with 360 degree views, a clubhouse with gym, sports bar, billiards, spa and covered porch that overlooks the sunken stone walled tennis courts, well appointed 2 bedroom guesthouse and an extraordinary residence.Masterfully designed, this classic Georgian Federal offers gracious but comfortable living with rooms that are inviting and capture the splendor of its surroundings with vistas from every vantage point.Grand and open gathering rooms ideal for spending time with family and friends, entertaining summer and winter guests. Refined architectural features, exceptional decor, multiple fireplaces, multiple bedroom suites, lovely patios. Don't overlook this extraordinary Property and Price.

Listed by Kim Morgan-Wohler of Wohler Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 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 September 23, 2019.