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. 

Falls Brook Road Killington VT 05751

Killington, VTFalls Brook Road

Price$5,900,000

Est. Mortgage: $/month

MLS Number 4888551

  • Land
  • Acreage 256.29
  • Utilities None
  • Zoning PRD-PUD

Killington CHERRY KNOLL (KCK) is 256 acres of privately held land characterized by diverse terrain with dramatic 'front & center' views sweeping over the face of Bear Mountain. An extraordinary opportunity for 'ski on and off' homesites is afforded by Killington's Sunrise Triple Chair ski lift terminal & trails covered by snowmaking located on KCK land. Killington Ski Resort has been a site for World Class events from the days of the legendary Mahre brothers & Ingemar Stenmark to the Audi FIS Women's World Cup. In addition to recreational options at Killington--KCK adjoins thousands of acres of protected land with miles of trails for year round outdoors activity; hiking, mountain biking, XC skiing, horseback riding, snowmobiling & ATV rambling. The parcel surrounds Sunrise Village complex & Falls Brook Commons with its family-friendly Cafe' at the base of Bear Mountain. Tremendous energy & optimism has been generated by $29 million dollars of improvements underway at Killington and S&P Land's "ski village" has received permits for construction. A complete revitalization of the Bear Mountain Lodge is moving forward. The Town Plan & Zoning allows for a variety of uses ranging from a Ski Village complex with hotel & restaurants to very private homesites or a generational family compound. Engineering enabling some of the options has been done. Killington CHERRY KNOLL is an unequaled opportunity to invest in Vermont with possibilities limited only by imagination.

Listed by Laird Bradley of Williamson Group Sothebys Intl. Realty

$
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%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* 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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1699-1743 Spring Hill Road Londonderry VT 05155

MLS Number 4896058

  • Residential Single Family
  • Bedrooms 9
  • Bathroom 12
  • Construction Existing
  • Zip 05155

Just minutes to Stratton and Bromley, this exquisite property on 115 acres places you in the center of ski country, but that is just the start of your Vermont adventure. For those seeking excitement and proximity to nature this home offers the lifestyle you have been looking for. Snowmobile out of your barn and across the fields, swim in the natural stone pool, make tracks on the motocross course, fish from your own spring-fed pond, golf on the 3-hole course, practice your aim from the skeet shooting barn and camp in the cabin. Back at the main house, revel in luxury and host with ease. Crafted from reclaimed barnwood, the lodge style great room features a magnificent stone fireplace and handsome bar. The adjacent all season room with fireplace and walls of glass offer stunning views. Prime for entertaining, the dining room with wood burning hearth opens to a cozy gathering room for after dinner liquors and dessert around a roaring fire. Kitchen designed with stations for breakfast/coffee, food prep, après ski cocktails and hors d'oeuvres is equipped with upscale state of the art appliances; Thermador range, double oven, Sub-Zero refrigerator & dual wine coolers. When the day comes to a close, unwind in the serene master ensuite with its stone fireplace, balcony, and copper soaking tub. Featuring 8 additional bedrooms, 11 beautifully tiled baths, a game room with bunks, stone pool and hot tub & multiple barns. Experience a lifestyle that matches the caliber of this property.

Listed by Cheyanne Pugliese and Kim Morgan-Wohler of Wohler Realty Group

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$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* 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.

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$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* 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 4911369

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

Stratton Mountain Estate-Rarely does one have the opportunity to acquire an iconic estate with a newly expanded and renovated grand lodge and guest house with extraordinary views of Stratton Mountain trails. This exceptional renovation of a Frank Lloyd Wright designed Pearl Buck property on 35+/- acres is just minutes to the Stratton Mountain 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 througout 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

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$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* 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$3,200,000

Est. Mortgage: $/month

MLS Number 4905858

  • 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. All measurements approximate.

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

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$
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$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* 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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2989 Under The Mountain Road Londonderry VT 05155

MLS Number 4930276

  • Residential Single Family
  • Bedrooms 4
  • Bathroom 6
  • Construction Existing
  • Zip 05155

A breathtaking view of Bromley Mountain and Stratton resort surrounds this Adirondack-inspired mountain retreat on 120 private acres above Under The Mountain Road. Custom maple entry welcomes you to a magnificent split-level layout that leads you to the great room, dining room, chef's kitchen, breakfast nook, den, office, and first-floor bedroom suite with space for a gym or spa. Large indigenous stone fireplaces and floor-to-ceiling windows highlight the spacious great room and long range views from the office redefine working remotely. Large mudroom with separate entry has access to the attached heated three bay garage. The second floor has three large bedrooms, each with on suite bathrooms. On the lower level there is an additional bedroom and bathroom, as well as a recreational room with a wet bar. Summertime entertainment and outdoor dining are made possible by the generous patio surrounded by hydrangeas on the western side of the home. There is abundant storage and potential in the detached 1,500sq ft barn that has parking for two. In warmer months, cool off with a swim in the crystal-clean pond fed by one of the three wells on the property. Also included are a whole house generator and an irrigation system for the lawn. Green Mountain living is refined and elevated in this meticulously maintained South Londonderry getaway! Additional 20 acre subdivison with two wastewater permits across Under The Mountain Road is included in the sale.

Listed by Andie Fusco of Four Seasons Sotheby's Int'l Realty

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$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* 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$2,950,000

Est. Mortgage: $/month

MLS Number 4924477

  • 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

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$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* 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$2,500,000

Est. Mortgage: $/month

MLS Number 4917068

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

Magnificent Offering... Quintessential Dorset Farm! 187 pristine acres in the heart of Dorset on coveted Nichols Hill! Mixture of beautifully managed meadows, sugarbush, woods, stream and pond in Current Use and The Vermont Land Trust. Equine or agriculture friendly with access to all lands through myriad of groomed trails. Incredible panoramic views are distant and intimate. Lovely Goodman Brook meanders thru the property and there is a small pond. Two very well appointed homes include the original farmhouse, a newer constructed cape, a large P&B antique barn and outbuilding in a picturesque tranquil setting. A 1850 2026 SF Colonial and a 1980 2160 SF Cape totals 4,186 finished square feet offering 8 bedrooms between the two homes. Understated elegance. Healthy Forestry Plan. Sellers have gone to great lengths to preserve the property and habitat. Vermont Land Trust owns the development rights but there is the ability for one more homestead within the property. Perfect for a family compound or off-set income potential. Forestry and Land Trust Docs available upon request. Superb View Setting... Bike Ride to Dorset Village... this is the ultimate offering base toward an amazing Dorset Compound!

Listed by Josiah Allen Real Estate,Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* 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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166 McKeighan Road Rupert VT 05776

Rupert, VT166 McKeighan Road

Price$2,500,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4900123

  • Residential Single Family
  • Bedrooms 4
  • Bathroom 5
  • Construction Existing
  • Zip 05776

An estate for the most discerning of buyers. Have you been looking for an estate that combines exquisite details, views, and options for unlimited uses along with privacy? Need a gentlemen's farm for your pleasure horses? An estate suitable for an established events person? If so, this property is for you! 267.5 acres of rolling hills. Here you will find a custom built owner's residence which combines the moving of two barns which were rebuilt into one post and beam, owners residence. The detailing is second to none. A few steps from this home is the most amazing of pool houses which has every upgrade imaginable and allows for swimming 365 days/year, in all weather. There are four independent living accommodations along with a tractor barn, 6 bay animal pen, an animal holding barn with a separate veterinary room with heat and water, and walk in cooler. All electrical is underground. There are four ponds. No chemicals have been used anywhere on this land for the past 17 years so organic certification is possible. This is the estate to be at if another pandemic hits. This property is perfect for destination weddings, family retreats, corporate events and so much more. Come see for yourself, everything you could possibly need is here. All measurements are approximate and are only for the main house. There is a whole farm diesel generator and a propane generator for main house and pool.

Listed by Lynn Rawson of Four Seasons Sotheby's Int'l Realty

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$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* 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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305 Birch Hill Drive Manchester VT 05255

Manchester, VT305 Birch Hill Drive

Price$2,200,000

Est. Mortgage: $/month

MLS Number 4927884

  • Residential Single Family
  • Bedrooms 4
  • Bathroom 4
  • Construction Existing
  • Zip 05255

Peacefully relax on your back deck and enjoy the views of Mount Equinox from your own 28 acre oasis privately located off Manchester West Road. This unique property has everything you have been looking for in Vermont. The property features a main residence with air conditioning, 4 bedrooms; one being a first floor suite and a second floor primary with updated bath and walk in closet, a great room, two fireplaces, covered porch and back deck with outdoor grilling area. Many outbuildings and a detached 1 bedroom guest suite. You can enjoy a network of meticulous trails and manicured grounds, numerous garages and all with the convenience of Manchester Dorset and the Mountains. Snowmobile, hike, ski or ATV right out your back door to the trails. There is a cleared private gazebo area with a oversized fire pit. The expansive yard has a clubhouse, basketball/ pickle ball court, shooting rage and bocce ball court. Acreage also has access off of Three Maple Drive and can be further subdivided to suit the buyers needs in many different ways. A must see-- not often does property with so much to offer and potential come around in Manchester.

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

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$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* 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 and Tammy Howard Davis of Watson Realty & Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* 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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1300 Mountain Road Ludlow VT 05149

Ludlow, VT1300 Mountain Road

Price$2,000,000

Est. Mortgage: $/month

MLS Number 4898526

  • Residential Single Family
  • Bedrooms 4
  • Bathroom 5
  • Construction Existing
  • Zip 05149

One-of-a-kind location on Okemo Mountain. This property enjoys direct Slopeside access on Okemo's Mountain Road Trail. Land runs down adjacent to the Sidewinder Trail. Above Solitude Village. Northern boundary is the Coleman Brook. Fantastic views to the east with clearing. Current winter access is via ski lift only. Off season access is via the Mountain Road. If you have a vision, this could be anything you want it to be - think outside the box - a unique investment property or family compound. There is a lot you can do with 27 acres on Okemo Mountain. Home is in need of restoration. Home has been vandalized and is in disrepair. All utilities/systems formerly in place are unknown at this time. Three levels of living space plus basement and five marble bathrooms. Sold "as is". So many possibilities here!

Listed by Teresa DiNapoli of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* 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 2022 New England Real Estate Network, Inc. All rights reserved. This display of listings may or may not be the entire Compilation from the NEREN database, and NEREN does not guarantee the accuracy of such information. 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 November 30, 2022 2:24 AM EST.