and narrow your search. If you have fewer than 200 results, you can save your search.

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. 

820 Mountain Road, Stratton, VT 05155

Price$4,800,000

Est. Mortgage: $/month

MLS Number 4658427

  • Residential Single Family
  • Bedrooms 12
  • Bathroom 14
  • Construction Existing
  • Square Feet 9012

Snowy Pond Estate is nestled in the scenic Green Mountains of Southern Vermont and located within minutes of iconic resorts: Stratton Mountain and Mount Snow. This exceptionally pristine property with unrivaled outbuildings spans over 160 park-like acres. Surrounded by the Green Mountain National Forest, away from the daily activity of the resorts, one can find solace knowing that the area restaurants and boutique shops are just minutes away. The private gated entry welcomes all to the Main Residence and not only impresses with the quality of the finishes but the attention to every detail. Designed to be a residence that captures natural light, it also merges the mountain's profile and landscaping into its form. Manicured perennial gardens overlooking the pond reflect the setting from the custom stone patio transcending down to the dock below. The remarkable six acre pond, built by the U.S. Army Corp of Engineers, is richly stocked with an abundant inventory of lively native trout. Additional residential dwellings of Snowy Pond Estate define understated comfort yet feature all of the amenities a discerning guest would desire: the Main Residence, Carriage House, Authentic Michigan Log Home, Two Bedroom Guest House, Vintage Cabin, Custom Steel Storage Garage and Post & Beam Barn in total contain 31 rooms, 12 bedrooms and 14 bathrooms. Each of the residences have their own tranquil backdrop perfectly transposed on the property to capture a view of the pond.

Listed by Hayleyanne Van Der Kar and Andy Reed of Four Seasons Sotheby's Int'l Realty

{$office->Name}

Josiah Allen, Manchester
4532 Main Street
Manchester VT, 05254
Office: 802.362.3355

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.57% last updated on Jun 21, 2018
* 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

2356 Lovers, Chester, VT 05143

Price$4,650,000

Est. Mortgage: $/month

MLS Number 4507606

  • Residential Single Family
  • Listing Agent Name T Story Jenks
  • Bedrooms 6
  • Bathroom 5
  • Construction Existing

This 1,881.19 acre farm in Southern Vermont has been assembled over 40 years and carefully managed as a family retreat providing complete privacy and excellent views. The property includes a c1819 Farmhouse with 4,930 s.f. and 6 bedrooms, Guest House with 2 bedrooms, 2 Antique Post & Beam Barns, and a secluded Log Cabin. The diverse landscape has 60 acres of meadows suitable for agriculture, a stocked 2-acre pond, orchards, streams, and 3.5 miles of top grade access roads throughout the property. The 1,839 acres of carefully managed northern hard wood forest, predominate in Sugar Maple, has a Timber Capital Value estimated at $2.67M. Located 4 hours from NYC, and 2.5 hours from Boston.

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

{$office->Name}

Josiah Allen, Dorset
3115 Vermont Route 30
Dorset VT, 05251
Office: 802.867.5555

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.57% last updated on Jun 21, 2018
* 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

Windham, VT 05359

Price$3,990,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4653876

  • Land
  • Listing Agent Name Robert Waite
  • Acreage 3500

Londonderry/Windham, Vermont, Glebe Mountain Range. Unspoiled wilderness with mountain tops, beaver meadows, hidden ponds, brooks, forest pastures, 5+ miles of dirt roads with old historic house foundations make this a very special property and ideal family or corporate retreat. Truly a rare and very special offering in Southern Vermont

Listed by Robert Waite and Lavinia Lee Brown of Four Seasons Sotheby's Int'l Realty

{$office->Name}

Josiah Allen, Manchester
4532 Main Street
Manchester VT, 05254
Office: 802.362.3355

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.57% last updated on Jun 21, 2018
* 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

2356 Lovers, Chester, VT 05143

Price$3,750,000

Est. Mortgage: $/month

MLS Number 4634314

  • Land
  • Listing Agent Name T Story Jenks
  • Acreage 1807.49
  • Zoning Rural

One of the best investments on the market today. Chester Forest consists of 1,807.49 acres of a well-stocked and managed forest with over $2.67 million of standing timber, dominated by Sugar Maple. On the property is an easily accessible 650 square foot log home built in 1991 from logs harvested from the land and set in an apple orchard field with tremendous views to the southwest.

Listed by T Story Jenks of LandVest, Inc/Woodstock

{$office->Name}

Josiah Allen, Dorset
3115 Vermont Route 30
Dorset VT, 05251
Office: 802.867.5555

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.57% last updated on Jun 21, 2018
* 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

2356 Lovers, Chester, VT 05143

Price$3,750,000

Est. Mortgage: $/month

MLS Number 4669793

  • Residential Single Family
  • Listing Agent Name T Story Jenks
  • Bedrooms 1
  • Construction Existing
  • Square Feet 650

One of the best investments on the market today. Chester Forest consists of 1,803.79 acres of well-stocked and managed forest with over $2.6 million of standing timber, dominated by Sugar Maple. On the property is an easily accessible 650 square foot log home built in 1991 from logs harvested from the land and set in an apple orchard field with tremendous views to the southwest.

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

{$office->Name}

Josiah Allen, Dorset
3115 Vermont Route 30
Dorset VT, 05251
Office: 802.867.5555

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.57% last updated on Jun 21, 2018
* 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

1048 Black Hole Hollow Rd, Arlington, VT 05250

Price$3,700,000

Est. Mortgage: $/month

MLS Number 4502293

  • Residential Single Family
  • Listing Agent Name T Story Jenks
  • Bedrooms 8
  • Bathroom 7
  • Construction Existing

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 and Wade Weathers of LandVest, Inc/Woodstock

{$office->Name}

Josiah Allen, Manchester
4532 Main Street
Manchester VT, 05254
Office: 802.362.3355

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.57% last updated on Jun 21, 2018
* 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

864 Rogers, Rupert, VT 05251

Price$3,600,000

Est. Mortgage: $/month

MLS Number 4496096

  • Residential Single Family
  • Listing Agent Name Andy Reed
  • Bedrooms 4
  • Bathroom 6
  • Construction Existing

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 and can be offered with an additional 278 acre building lot of mixed forest and open land .

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

{$office->Name}

Josiah Allen, Dorset
3115 Vermont Route 30
Dorset VT, 05251
Office: 802.867.5555

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.57% last updated on Jun 21, 2018
* 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

1108 West Hill Rd, Jamaica, VT 05343

Price$3,290,000

Est. Mortgage: $/month

MLS Number 4470997

  • Residential Single Family
  • Listing Agent Name Diana Stugger
  • Bedrooms 8
  • Bathroom 8
  • Construction Existing

BETWEEN HEAVEN & EARTH: Spectacular panoramic vistas of mountain ranges and country valleys under a sweeping sky from this magnificent ski country estate on 99 private acres. A scenic driveway wends its way past a lighted skating pond with warming hut & heated paddle tennis court up to the timeless 8 bedroom, 8 bath main residence on a serene hillside setting. A captivating 3 bedroom, 2 bath guest apartment finds seclusion above the detached 3-bay garage. Spaciousness, comfort, convenience define the open living areas with access onto expansive viewing porches & patios & winterized sun porch. Designed for ease of entertaining & a retreat for the few or many, the main level master suite & en suite guest bedrooms provide restful privacy. Steps from the house & under the stars is a glass enclosed gazebo with hot tub. Stone walls & perennial gardens enhance the harmonious natural landscape. Self-contained & away from the world, yet 15 minutes to Stratton Resort.

Listed by Diana Stugger and Bob Maisey of Four Seasons Sotheby's Int'l Realty

{$office->Name}

Josiah Allen, Manchester
4532 Main Street
Manchester VT, 05254
Office: 802.362.3355

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.57% last updated on Jun 21, 2018
* 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

415 Uphill Lane, Dorset, VT 05253

Price$2,950,000

Est. Mortgage: $/month

MLS Number 3058863

  • Residential Single Family
  • Listing Agent Name Elena Atwill
  • Bedrooms 8
  • Bathroom 8
  • Construction Existing

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

{$office->Name}

Josiah Allen, Dorset
3115 Vermont Route 30
Dorset VT, 05251
Office: 802.867.5555

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.57% last updated on Jun 21, 2018
* 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

905 Dawley, Mount Holly, VT 05758

Price$2,900,000

Est. Mortgage: $/month

MLS Number 4395912

  • Residential Single Family
  • Listing Agent Name Frank Ellison
  • Bedrooms 3
  • Bathroom 3
  • Construction Existing

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!

Listed by Frank Ellison of Coldwell Banker Watson Realty/ Ludlow

{$office->Name}

Josiah Allen, Dorset
3115 Vermont Route 30
Dorset VT, 05251
Office: 802.867.5555

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.57% last updated on Jun 21, 2018
* 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

1418 West Jamaica, Jamaica, VT 05343

Price$2,750,000

Est. Mortgage: $/month

MLS Number 4651063

  • Residential Single Family
  • Listing Agent Name Ellen Mallia
  • Bedrooms 4
  • Bathroom 5
  • Construction Existing

A world unto itself! From the moment you enter onto this majestic property set among the maples and pines, you feel as though you have stepped into your own woodland sanctuary. Heading up the private drive, the beautifully designed four bedroom Vermont Timberpeg home sits atop the 351-acre parcel to take full advantage of the spectacular views of the Southern Vermont Green Mountains and Stratton Resort trails. The bright and open kitchen balances warmth, functionality and flow with a large black granite island, double ovens, wet bar with wine cooler. Watch the native Deer, Moose and Foxes make their journey through the lawn from expansive living and sitting room windows. Gather your family and friends around either of the brick fireplaces in the living and dining areas. The airy main floor master bedroom with inviting gas fireplace, looks out onto a pond with natural waterfall. Second floor guest suites feature private balconies with views of Stratton Mountain Sun Bowl trails. The three bay garage provides storage for all your Vermont gear; atvs, snowmobiles, canoes, paddle boards, skis and snowboards. Above the garage offers wonderful guest space featuring an open kitchen and living area with private bath. Located just three miles from Stratton Mountain Resort, this property has every space both inside and out on its land that you are looking for in owning your own private retreat and enjoying some of the best that Vermont has to offer.

Listed by Ellen Mallia and Tara van de Velde Senecal of Four Seasons Sotheby's Int'l Realty

{$office->Name}

Josiah Allen, Manchester
4532 Main Street
Manchester VT, 05254
Office: 802.362.3355

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.57% last updated on Jun 21, 2018
* 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

100 Fairbanks Road, Grafton, VT 05146

Price$2,750,000

Est. Mortgage: $/month

MLS Number 4700648

  • Residential Single Family
  • Listing Agent Name Carol Wood
  • Construction Existing
  • Bathroom 4
  • Bedrooms 4

Nestled discreetly in the hills of historic Grafton with panoramic long-range southerly views , Pine Hill Farm is a unique, totally private country estate. The understated elegance, disciplined composition and organic elements of this home invoke a tranquility that transcends throughout. The 6' high walk-in field- stone fireplace commands the great room within a massive antique hand-hewn chestnut barn frame. The open concept footprint is ideal for entertaining with a well appointed chef's kitchen complete with La Canche range with dual fuel ovens, top of the line appliances and local red slate counters.The patinaed copper and black walnut bar with integrated audio system is perfect for entertaining your guests. Enjoy the luxurious grand master suite with copper soaking tub, wet and dry sauna and private deck with hot tub. The attached four season greenhouse and potting room give you a head start on the planting season. Beautifully landscaped with copious gardens and mature plantings to offer an ever-changing palate throughout the seasons.Comprised of 69 bucolic acres and an award winning Tree Farm, Pine Hill Farm features a separate, guest house, heated swimming pool , barn with fenced pasture, equipment barn, spring fed swimming pond and extensive trail network. Large lower area offers plenty of room for expansion, media room or gym. 5 minutes from Grafton Village . Easy drive to multiple ski resorts and recreation. Escape the city's hectic life to your own zen retreat.

Listed by Carol Wood and Danny Kogut of Williamson Group Sothebys Intl. Realty

{$office->Name}

Josiah Allen, Manchester
4532 Main Street
Manchester VT, 05254
Office: 802.362.3355

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.57% last updated on Jun 21, 2018
* 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Broker Reciprocity

Copyright 2018 Northern 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. Subject to errors, omissions, prior sale, change or withdrawal without notice. This web site is updated daily.