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. 

1699-1743 Spring Hill Road Londonderry VT 05155

MLS Number 4822484

  • Residential Single Family
  • Bedrooms 9
  • Bathroom 11
  • Construction Existing
  • Zip 05155

Luxury just 10 minutes from Stratton or Bromley Mountains! The serene beauty of Vermont beckons you while you stroll through your orchard, fish the trout stocked stream-fed pond, take a dip in the hot tub, or cool off in the natural stone pool or swimming hole on the river that features a sleeping cabin. For entertainment there is a 3-hole golf course on the property, a shooting barn with an automatic clay thrower and a motocross track. This private oasis offers views of both Stratton and Bromley while also featuring several outbuildings to include a hay barn with workshop and a 6-bay pole barn. The possibilities are endless as is the beauty and charm of this property.

Listed by Carrie Mathews of William Raveis Winhall

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$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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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90 Snow Valley Road Winhall VT 05340

Winhall, VT90 Snow Valley Road

Price$4,950,000

Est. Mortgage: $/month

MLS Number 4826030

  • Land
  • Acreage 447

On the slope-side of the storied Snow Valley Ski Resort, presents a truly unique development opportunity for a new vision to encompass a family-oriented, four-season community resort. Drawing from the major metropolises of New York City and Boston, this 450+ acre site is poised to draw a number of hospitality, residential and recreational uses to capture increasing demand by urban residents seeking immersion in nature and the great outdoors. A buyer or equity partner will be presented with the ability to create an authentic, architecturally significant, multifaceted venue giving nod to the great historical Adirondack camps, mountain communities and traditional Vermont homesteads. As an eco-minded boutique hotel/glamping resort, sporting club, residential community, or iconic estate property, future patrons and residents will have endless activities to enjoy in this ultimate safe haven.

Listed by Paul William Carroccio and Marek Kovac of TPW Real Estate

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$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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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1048 Black Hole Hollow Road Arlington VT 05250

MLS Number 4868628

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

Ian Fleming, Famed creator of James Bond, once mused in the guest register of Black Hole Hollow Farm, "Lived here like a king - an uninvited one - in fragrant and luxurious solitude" a bucolic and timeless sanctuary. This remarkable estate located on 228 verdant acres bordering both state and national forest, offers an unparalleled backdrop to an especially private hideaway. Extensive walking and riding trails are interwoven throughout. The beautiful stone mansion overlooks lush hilled lawns, two tiered ponds and waterfalls. Original house dates from 1772, expanded and designed by the renowned architect Jerome Cerny in the 1930's. The grand living room and downstairs bedrooms open onto the gardens through French doors and master suite provides private access to a poetic walled garden. There are fireplaces throughout, attached guest house, heated greenhouse, barn, cutting and vegetable garden. The estate has entertained a cast of characters including Sir Ian Fleming, spending summers finding inspiration and writing the classics "Diamonds Are Forever," "Goldfinger" and "For Your Eyes Only." Owners were Josephine Hartford Bryce, heiress of A&P, and husband Ivar rumored to be the inspiration for Bond. Easy drive to Albany Int'l Airport, Manchester and Saratoga's thoroughbred racing. Cultural activities of theatre, art, museums and dance nearby. To hike, ride, hunt, farm, fish or drive off-road in the surrounding forest. To find inspiration in a deeply rooted sense of home.

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

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$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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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358 Andover Ridge Road Andover VT 05143

Andover, VT358 Andover Ridge Road

Price$3,200,000

Est. Mortgage: $/month

MLS Number 4864436

  • Residential Single Family
  • Bedrooms 7
  • Bathroom 6
  • Construction Existing
  • Zip 05143

Tucked away on Andover Ridge Rd you will find one of the most spectacular properties in Southern VT. This remarkable log home features 7 bedrooms and over 7,000 sq ft of finished living space. The main floor is an open floor plan that features, a large kitchen with granite counters, custom cabinetry, top end appliances and an full length of kitchen island. The kitchen opens up to the dining area and a living room that boasts a custom stone wood burning fireplace, vaulted ceilings and floor to ceiling windows that give you breathtaking westerly views for picturesque sunsets and year round enjoyment of all the changing seasons. The main floor also features a den study and an owners en suite bedroom with gas fireplace. The main floor includes multiple accesses to the large wrap around deck looking down to the pond and property. On the second floor you'll find a game room loft and 3 more bedrooms including another en suite master. Down below the finished basement has a large family/ rec room for gathering, 3 more bedrooms with another en-suite master. The lower floor is a walkout to the stone patio that leads down to the amazing lined pond surrounded by incredible stone work, walls and perennial gardens giving you a truly breathtaking setting. The pond even features a waterfall incorporated into the stone work. 72.8 acres with accessible road frontage on Weston-Andover Rd. Possible future development. Just a short distance to Weston, several ski resorts, and VAST trails.

Listed by Gary Coger of Four Seasons Sotheby's Int'l Realty

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$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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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905 Dawley Road Mount Holly VT 05758

Mount Holly, VT905 Dawley Road

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: 2.8% last updated on Jul 29, 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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2210 Sugar Hill Road Wallingford VT 05742

Wallingford, VT2210 Sugar Hill Road

Price$2,750,000

Est. Mortgage: $/month

MLS Number 4863567

  • Residential Single Family
  • Bedrooms 4
  • Bathroom 6
  • Construction Existing
  • Zip 05742

TIMBERS IN THE SKY. This 2012 custom Davis Frame Timber home is a true masterpiece. The awe-inspiring methods and delicate balance of building this post and beam structure, high level of finishings, rich details, and skilled craftsmanship are incredible. A collaboration of builder and owner put extraordinary effort into making an efficient home and was awarded a five-star plus rating. Sited perfectly on 27 private acres and stunning mountain views is this quintessential Vermont Estate. Four-bedroom, five-bath, 5600 Sq. Ft. home features a great room and staircase that is a work of art. The Douglas Fur timbers, floor-to-ceiling granite fireplace, windows that highlight the mountain views, are spectacular. The custom kitchen hosts Vermont stone products and beautiful cabinetry. Enjoy the adjacent three-season porch, dining room with raised panel wainscoting, and a built-in buffet. First-floor master suite, luxury bath, and walk-in closet. The second floor features two bedrooms, a home office, and a loft area. Enter a mudroom, laundry room, and access up to a bonus room off the heated three-car garage. The lower walkout level family room, wet bar, entertainment room, and fourth bedroom are light-filled. Climate-controlled wine room for the connoisseur too. Stay at home and enjoy the 20'x40' saltwater heated pool. 12'x24' pool house is a dream with its beverage kitchen, ice machine, and half bath. Detached two-car garage for your VT. toys. Fantastic location, 12 mile to Okemo

Listed by Freddie Ann Bohlig of Four Seasons Sotheby's Int'l Realty

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$
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$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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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636 Fowler Brook Road Mount Holly VT 05758

Mount Holly, VT636 Fowler Brook Road

Price$2,490,000

Est. Mortgage: $/month

Active With Contract

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. See property video. The property is conveniently located near Okemo between Woodstock and Manchester and close to Rutland, Rutland Southern Vermont Regional Airport (RUT) and Weston.

Listed by John Snyder of Snyder Donegan Real Estate Group

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$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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

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$
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$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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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2198 Shunpike Road Mount Holly VT 05758

Mount Holly, VT2198 Shunpike Road

Price$1,995,000

Est. Mortgage: $/month

MLS Number 4861001

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

Fern Hill - A Gracious Estate that Lives Large! This stately five-bedroom, seven-bath home is situated on 207 acres with 32 acres of open meadow and a private 1.5 acre pond. This lovely estate provides loads of privacy. Once inside, the mud room draws you in with elegant country charm. The Great Room which features a stone fireplace and 103 inch, drop-down TV screen to view your favorite sporting events & movies is the perfect spot to bring everyone together. The open kitchen includes Energy Star, stainless appliances and an informal option for dining, with views of the stone courtyard plus it opens to the inviting family room with fireplace. The formal dining room offers a fireplace and built-ins. The main level deluxe master suite has a walk-in closet, gas fireplace and spacious bathroom with Jacuzzi-style tub and steam shower. Step down the hall for a relaxing sauna. The second level offers four charming bedrooms, each with en-suite baths (some with steam showers). Above the 2-car attached garage is an 800-square foot game room with pool table and bath. The stone courtyard includes a privately-placed hot tub - perfect for gazing at the amazing stars. Take a short walk to the trout pond and walking trails. The VAST snowmobile trail runs along the far end of the property. Enjoy hiking, riding, cross-country skiing and snow shoeing on your own private trails. Ten minutes to Okemo Mountain Resort, airport and shopping.

Listed by Gail Beardmore and Rachael Hyjek of Engel & Volkers Okemo-Woodstock

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$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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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29 Deeryard Road Winhall VT 05340

Winhall, VT29 Deeryard Road, Unit 21

Price$1,800,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4869036

  • Residential Single Family
  • Bedrooms 4
  • Bathroom 4
  • Construction Existing
  • Zip 05340

GREEN ACRES IS THE PLACE TO BE............................................. Unprecedented views from this amazing mountain contemporary. BIG Stratton views and beyond await you on 26 rolling acres with all the recreation at your doorstep you can possibly take in, in one day. This gorgeous property is perfect for entertaining your large family or guest gatherings with many common areas inside & out. Attractive stone patios, porches and decks allow you to enjoy the scenic outdoors while almost every interior room boasts magnificent mtn views. Over the years the current owners have renovated, updated & added additional space to accommodate their active lifestyle. The enormous recreation room on the upper level overlooking the back patio is a huge feature you will greatly appreciate. Sleek kitchen w/granite counter tops, breakfast table & island. Comfortable media room, den with additional fireplace and loft office area add extra living spaces for you & your company. Plenty of sleeping accommodations on multiple levels. Wine cellar is conveniently located below the dining/kitchen. Private screened in porch. Sunken hot tub. Solar panels on the roof. Take a walk up to the upper property & after a vigorous game of tennis on a well maintained court follow the groomed path down to a beautiful, clean swimming pond 9' deep or simply jump in the outdoor shower. Enjoy walking & snowshoeing trails already laid out for you. We can't wait for you to see this extraordinary listing!

Listed by Terry Hill of Mountain Realty

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$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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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111 Prospect Point Road Castleton VT 05735

Castleton, VT111 Prospect Point Road

Price$1,800,000

Est. Mortgage: $/month

MLS Number 4874878

  • Land
  • Acreage 60.28

One-of-a-kind premier waterfront property on Lake Bomoseen! Bomoseen Golf Club is a 9 hole public golf course nestled alongside beautiful Lake Bomoseen. The course allows golfers to soak in the lake views and the breathtaking rolling hills that surround it. The course is conveniently located on the lake with dock spaces available for those traveling by boat. Following a round of nine, golfers can enjoy a meal or cocktail on the property at the restaurant (currently closed) and located in the same building you will find the pro shop. Come see this amazing opportunity right next to the water and take a tour of the grounds and buildings, you are sure to fall in love! RC (recreational Commercial zone)

Listed by Carrie Mathews of William Raveis Winhall

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$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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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330 Rupert Mountain Road Pawlet VT 05761

Pawlet, VT330 Rupert Mountain Road

Price$1,750,000

Est. Mortgage: $/month

MLS Number 4866985

  • Residential Single Family
  • Bedrooms 4
  • Bathroom 6
  • Construction Existing
  • Zip 05761

'The Hill' is a special 54 -acre Alpaca farm compound with multiple outbuildings that is privately sited high with spectacular north views of Haystack Mountain, south views to the valley below and rolling pasture and woodlands to the 900 feet frontage on the Mettawee River. This unique property is conveniently located to the historic village of Pawlet. With the advantage of views throughout the four en-suite bedrooms, open living spaces. loft office, country kitchen and dining area there is always the theatre of dramatic vistas. The full living/working ground level spaces with spacious bath complete the main house. Follow the compound road to a cottage with stone fireplace, a 'fishing club house' on the Mettawee River and multiple barns along the way. 'The Hill' dominating the valley is a gem with functioning revenue.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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 August 2, 2021.