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. 

85 Pallottas Hill Road Ludlow VT 05149

Ludlow, VT85 Pallottas Hill Road

Price$9,995,995

Est. Mortgage: $/month

MLS Number 4955858

  • Land
  • Acreage 127
  • Zoning Mixed

127 Acres of Meadows, Forest, Trail Networks and Panoramic Views at the foot of Okemo Mountain, 2 minutes to downtown Ludlow and the Okemo ski lifts. This sprawling acreage can become single family homes, condominiums, town houses, a hotel or any combination thereof. Engineering work has identified the potential subdivision of the property. This developers dream is truly a blank canvas. Meticulously maintained, the property offers direct access to the VAST trail system. Enjoy cross country skiing, hiking and a multitude of other outdoor activities on the expansive trail network. Inspirational views in every direction including Okemo Mountain, Mount Ascutney and the Green Mountains to New Hampshire and beyond. It stands as one of the last undeveloped large parcels in Ludlow. A playground for the ultimate outdoor lover, this must see property awaits your creative vision to be transformed into the latest in luxury mountain living. The pristine four bedroom farm house can be subdivided off and sold or be used as a guest house. Endless possibilities!

Listed by Frank Provance of Diamond Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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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85 Pallottas Hill Road Ludlow VT 05149

Ludlow, VT85 Pallottas Hill Road

Price$9,995,595

Est. Mortgage: $/month

MLS Number 4955863

  • Residential Single Family
  • Bedrooms 5
  • Bathroom 2
  • Construction Existing
  • Zip 05149

Welcome home to this breathtaking 127-acre estate nestled at the foot of Okemo Mountain, just two minutes from downtown Ludlow. This extraordinary property encompasses sprawling meadows, enchanting forests, a network of scenic trails & panoramic views that will leave you in awe. Meticulously maintained, this generational farm sets the standard for perfection. The centerpiece of this remarkable estate is a beautifully renovated 4-bedroom, farmhouse. As you step onto the expansive stone patio, you'll be greeted by inspiring views in every direction, making it an ideal space for outdoor entertaining. Enter the oversized mudroom complete with laundry and custom storage designed to accommodate an abundance of gear. Inside the antique farmhouse, you'll find natural wood accents throughout, exposed natural beams, and tin ceiling, adding to its timeless charm and character. This well-appointed home can serve as your primary residence, a guest house, or sold to make way for your dream home on the surrounding acreage. The possibilities are endless. This exceptional parcel of land is one of the last remaining undeveloped properties in the area. It represents the ultimate playground for outdoor enthusiasts, unmatched in its offerings and natural beauty. Words alone cannot convey the possibilities and the sheer beauty of this unique parcel-this is a property that must be seen in person to fully appreciate its magnificence.

Listed by Frank Provance of Diamond Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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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999 Route 30 Rupert VT 05761

Rupert, VT999 Route 30

Price$3,995,000

Est. Mortgage: $/month

MLS Number 4904677

  • Residential Single Family
  • Bedrooms 5
  • Bathroom 7
  • Construction Existing
  • Zip 05761

Hagarbook Farm completely restored 5034 SF C. 1767 Residence consisting of magnificent Mettowee River frontage interior to the 320 acres, Hagar Brook and Waterfall, Harmons Mint Historic Site, Pond, Agricultural Fields, Extensive Trail System and View Sites galore! The Land Straddles both East Rupert and Dorset. Add significant buildings in lovely condition: 750 SF Guest House, Barn 37 X 100, Tractor Barn 26 X 50, Horse Barn 50 X 28 and additional out buildings--24 X 18, 20 X 14, 20 X 12, 16 X 12, 40 X 24! An exemplary eighteenth century compound approximately 3 miles north of the Dorset Green. The Great-Room Kitchen with exposed post and beam framing is the welcoming hearth of the home which walks out to the wrap around porch or sun room to the west where the living extends upon a wonderful level stone walled terrace overlooking the grounds and river beyond. Crisp architectural details witnessed in every room; Dining, Living, Family, Office and 4 Wonderful Bedrooms up. There are 5 baths, 2 half baths and a guest house ... Whether it's agricultural or equine interest, stream & field, auto collector, historical appreciation or family gathering ideals, this property is a treasure. Vermont Current Use real estate tax benefits for the next steward to embrace. 320 acres in the prized Mettowee Valley nearby Dorset!!!

Listed by Josiah Allen Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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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25 Mountain Haunts Road Winhall VT 05340

Winhall, VT25 Mountain Haunts Road

Price$3,950,000

Est. Mortgage: $/month

MLS Number 4945895

  • Residential Single Family
  • Bedrooms 6
  • Bathroom 7
  • Construction Existing
  • Zip 05340

This private setting on 40 acres is nothing short of EXTRAORDINARY! An iconic Stratton Mountain estate with a newly expanded and renovated grand lodge, a guest house - each with unrivaled views of the Stratton Mountain trails. The upscale addition & renovation of this Pearl Buck property is just minutes to the StrattonMountain Base Lodge. With commanding southerly views of Stratton Mountain and surrounding ridge lines with sunset views to the west, this dramatic 4 bedroom/ 4.5 bath lodge is without comparison and the last rare parcel of this size near the resort with a world of privacy and tranquility. Three stone fireplaces, large beams, walls of glass and VIEWS, VIEWS, VIEWS. Additional 2BR/2BA Guest House, garage, pond and tennis court. Patios, Stonework, outdoor spaces.enhance the stunning location.Additional building sites available. Situated in the heart of everything the region has to offer throughout the seasons. World Class professional theater at Weston and Dorset, the Manchester Music Festival, The Dorset Summer Equestrian Festival. Hiking, biking, kayaking, shopping and dining. Fall foliage, first tacks on powder days and the glorious Green Mountain Summers beckon. This one of a kind property has the essence of a true mountain lodge, set into its surroundings with a tranquil and peaceful vantage point. Adventure is at your doorstep.Additional parcels available. Make plans to visit this newly expanded and renovated property. You'll be enthralled!

Listed by Kim Morgan-Wohler of Wohler Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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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207 Brooks Lane Londonderry VT 05148

Londonderry, VT207 Brooks Lane

Price$3,195,000

Est. Mortgage: $/month

MLS Number 4971327

  • Residential Single Family
  • Bedrooms 9
  • Bathroom 9
  • Construction Existing
  • Zip 05148

This extraordinary, fully furnished property boasts an abundance of amenities and natural splendor. Revel in the awe-inspiring views and the tranquil swimming pond spread across these extensive 69 acres. Delight in the winding trails that lead to 1,235 feet of pristine West River frontage, providing year-round outdoor activities for all. With three distinct residences and a charming cabin, it offers ample space for everyone to convene while relishing their individual, private retreats. The main house, steeped in history dating back to 1820, is a delightful 3-bedroom brick farmhouse showcasing a generous 45-foot-long great room that seamlessly extends to a covered patio adorned with an awning-an idyllic setting for outdoor gatherings. The newly renovated kitchen, with granite countertops, serves as the heart of the home, combining modern elegance with timeless charm. The guest cottage features an additional three bedrooms, a cozy living room, and a well-appointed kitchen with an adjoining dining area. Adjacent to the guest cottage, a spa facility awaits, boasting a ground-level private gym, sauna, and an outdoor hot tub. Ascend to the second floor to discover two bedrooms, each with a private bathroom and a shared balcony. Nestled at the property's edge, overlooking the serene swimming pond with a beach, is a rustic cabin complete with a welcoming wood-burning stove and a lofted sleeping area. Ideally suited as a family compound, this retreat offers both separation and privacy

Listed by Timothy Apps of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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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528 & 540 Nichols Hill Road Dorset VT 05251

Dorset, VT528 & 540 Nichols Hill Road

Price$2,400,000

Est. Mortgage: $/month

MLS Number 4965438

  • Residential Single Family
  • Bedrooms 8
  • Bathroom 6
  • Construction Existing
  • Zip 05251

On an Eastern hillside, between two ridgelines of the Taconic Range, is Goodman Farm. It is reminiscent of an earlier time with two cottages and an antique red barn set at the edge of a spacious hay meadow just outside the village of Dorset. The 187 acres abuts Rupert State Forest with panoramic views, perennial gardens, stone walls and a small pond. Crossing the stone bridge over Goodman Brook and continuing along a carriage width trail to an upper meadow, there is an exceptional building site, which offers complete privacy and spectacular mountain views. The houses include a 2,026 s/f farmhouse built in 1850 with 4 bedrooms and a 2,160 s/f cape built in the 1980s with 4 bedrooms. May Goodman, a former owner and the namesake, was one of the founders of the Dorset Players in 1927. Over the last half century, the owners have lovingly managed the land and created an extensive trail network through the woodlands suitable for walking, riding, mountain biking, or snow shoeing. The large and majestic trees, mostly maple, are a result of a soil rich in lime. According to the forester, these Eastern facing slopes of the Taconic are some of the most productive timberland in the state. Wild elderberries, black walnuts and apple trees abound, and it is an important wildlife corridor. The property is in current use and has a conservation easement with the Vermont Land Trust. 12 miles from Bromley and 24 miles from Stratton. 4 h from New York and 3 h 18 m from Boston.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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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282 Peace Street Dorset VT 05251

Dorset, VT282 Peace Street

Price$2,350,000

Est. Mortgage: $/month

Pending

MLS Number 4959778

  • Residential Single Family
  • Bedrooms 5
  • Bathroom 4
  • Construction Existing
  • Zip 05251

Just outside the quiet village of Dorset and set against the backdrop of the Taconic mountains, this 20+ acre property reflects the pursuit of a slow, intentional existence with a connection between the living space and the outdoors. Charles Sawyer, the architect, drew from an Adirondack stylebook, integrating Douglas fir and native stone to create a sophisticated 5 bedroom dwelling. Sited at the water's edge of a large pond; the design takes in the views from the Great Room's expansive windows, from the spacious screened-in porch and from the first floor primary bedroom. Outside the upper stone terrace provides a lovely setting for summer suppers and the lower stone terrace, a hub for pond activities. The pond, generously fed by a well and spring, is stocked with trout, and is big enough for a paddle in a canoe and refreshing daily swims. A path runs along the Mettawee River on the NE border, another loops around the pond and there are adjoining trails to explore including into the village. Gather friends and family for a spirited game of hockey on the pond or snowshoe on the trails. Everyone can warm up beside a crackling fire in the stone fireplace in the Great Room, a perfect setting to reflect on the day's adventures. In addition to perennials, there's an edible landscape of asparagus, blueberries, apples and pears. Rounding out this slice of heaven is a greenhouse, sauna, rec room, office, gym, 2 bay garage and barn. High speed internet. Delayed Showings until 07.07.23.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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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95 Winhall Hollow Road Winhall VT 05340

Winhall, VT95 Winhall Hollow Road

Price$2,350,000

Est. Mortgage: $/month

Pending

MLS Number 4968392

  • Residential Single Family
  • Bedrooms 7
  • Bathroom 10
  • Construction Existing
  • Zip 05340

Nestled on 23 acres of secluded natural beauty with breathtaking mountain vistas, this custom-crafted estate offers a blend of comfort and leisure. Equestrian enthusiasts will appreciate the horse facilities, including a three-stall barn and a fenced paddock. The barn's versatility allows it to serve as a party space or extra storage as needed. A spacious three-car attached garage complements the property, while a charming stone patio and perennial gardens create an outdoor oasis where relaxation and functionality harmonize. Step indoors, and you'll find a home filled with exquisite features. The kitchen is a culinary masterpiece, the great room boasts a stone fireplace, and the billiard room invites friendly competition. The residence features high ceilings throughout and boasts seven ensuite bedrooms, ensuring maximum comfort and privacy for residents and guests alike. The inviting three-season porch hints at opportunities for entertaining in this private retreat. Conveniently located near Stratton, Bromley, and Magic resorts, this property is a dream for winter sports enthusiasts. It embodies a tranquil mountain lifestyle, seamlessly blending natural beauty with the comforts of upscale living.

Listed by Kevin Moran of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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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1176 Sandgate Road Arlington VT 05250

Arlington, VT1176 Sandgate Road

Price$2,250,000

Est. Mortgage: $/month

MLS Number 4962768

  • Residential Single Family
  • Bedrooms 6
  • Bathroom 5
  • Construction Existing
  • Zip 05250

Enchanting 1810 riverside estate featuring 6 bedrooms/ 5 baths set high on 21.85 park-like acres. Take in the majestic clear waters and the mountain vistas of the green river valley while relaxing on the veranda. Exquisitely updated farmhouse, expansive renovated barn with guest suites, office and studios, three-car heated garage, dreamy tree house and so much more. Meadows and fields to gaze upon, while you breathe the fresh Vermont air, allow for every day to be exceptional. The custom kitchen offers a Viking gas range and refrigerator, marble countertops, large pantry and open woodfire oven for the catch of the day. Easy flow from the kitchen, dining, living, patio, study, first-floor bedroom and bath. The second level offers two suites and a fourth bedroom. An impressively renovated barn with original vaulted ceilings features two additional guest suites with kitchens, two large studios or office spaces, and large lower-level workshop with French doors. The heated garages and other outbuildings make for easy living. Escape from the hustle and bustle of life is found in the vastness of open space and the serene presence of lush green mountains. Alternatively, one can opt to work from home alongside a tranquil river, enjoying the convenience of high-speed internet. New to market and ready for the next stewards. Don't miss the rare opportunity to make this magnificent estate your own.

Listed by Margretta Fischer of Wohler Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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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1086 West Road Bennington VT 05201

Bennington, VT1086 West Road

Price$2,225,000

Est. Mortgage: $/month

MLS Number 4952077

  • Residential Single Family
  • Bedrooms 9
  • Bathroom 7
  • Construction Existing
  • Zip 05201

Captivating French Provincial architecture is the hallmark of this 6,800 sq. ft 1866 Manor House occupying a commanding and picturesque view over 94 acres of pristine pastoral fields and the distant Taconic Mountain Range. The timeless and beautifully proportioned interiors feature extensive molding, solid oak flooring, eight fireplaces, nine bedrooms, seven baths, country kitchen and adjoining pantry, formal dining and living rooms. The private estate includes a three car garage, four bedroom caretakers cottage, artist studio and gunite in-ground pool. Set on the outskirts of the historic town of Bennington offering shopping, live theatre, restaurants, horseback riding and proximity to mountain and cross-country skiing. This is a rare opportunity to own an exquisite estate property with a myriad of possibilities as a family compound or country retreat. Only 45 minutes to Albany International Airport and approximately three hours to Manhattan and Boston. All measurements approximate.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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 Road Castleton VT 05735

Castleton, VTBirdseye Road

Price$2,100,000

Est. Mortgage: $/month

MLS Number 4888926

  • Land
  • Acreage 607.34
  • Utilities Other
  • Water View
  • Zoning RESD

A Sportsman's Paradise located in a college town! This is an amazing opportunity to bring back to life an old "Lost Ski Area" that opened in 1962! Formerly known as Birdseye Mountain Ski Resort with over 600+ acres located on three connected properties featuring a 1324' vertical drop offering unlimited potential from skiing to a huge campground. Only minutes to three major ski area, Castleton University, Lake Bomoseen & Lake St. Catherine, major highway of Route 4, and just 20 minutes to Rutland, Amtrack and CapeAir. This property is surrounded by thousands of acres of State Forest property- never to be developed for complete privacy and a hunters paradise. The mountain range offers views of the northern end of the Taconics. The north face starts off gradually near the base and rises dramatically near the summit. Castleton river runs through the property with a pond that served the west facing slope which used to offer night skiing as well as day skiing. ATV trails and VAST trail close by. A camping area was built in the 1970's with an in-ground swimming pool which is no longer in use. Huge development opportunity with some creative ideas are unlimited. "An exciting opportunity to own your own Mountain in the heart of Vermont's most famous ski country and develop a "Vermont Mountain Park"

Listed by Nancy Greenwood of Watson Realty & Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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$2,000,000

Est. Mortgage: $/month

MLS Number 4939595

  • Land
  • Acreage 387
  • Utilities None
  • Zoning Rec

Discover the potential of an alpine escape beyond compare in Snow Valley. Once a beloved winter destination in gorgeous Southern Vermont, Snow Valley operated largely under the radar from 1939 to approximately 1982, with a proud reputation as one of the nations very first ski areas and the very first snowboard area. The stunning 390+ acre property forms an ideal blank canvas for potential future home or family compound with all of the benefits of a resort experience. The region boasts over 120 inches of snowfall per year, truly perfect for the downhill and cross-country skiing Snow Valley was once renowned for, with its north-facing configuration of mountains that funnel snow well into the spring season. Picture-perfect vistas of Vermont countryside stretch in every direction, Snow Valley is ready to exceed every expectation. Additional 60 acre lot available - PID 00489 - Span 771-245-1019 owned by Prospect Rock LLC.

Listed by Timothy Apps of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* 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 2023 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. 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 28, 2023 10:40 AM EDT