Southern Vermont Properties with Over 100 Acres

Discover current properties with over 100 acres for sale in Southern Vermont. Use the criteria to the right to narrow your results to particular towns or price ranges, etc. Save your favorites when you create an account, and you can get email updates when new properties match your search criteria. For more information and to schedule a showing, don't hesitate to contact us.

2059 Upper Cold River Road Shrewsbury VT 05738

MLS Number 4908662

  • Residential Single Family
  • Bedrooms 4
  • Bathroom 5
  • Construction Existing
  • Zip 05738

Spectacular Shrewsbury home and acreage at the edge of a forest, on the back side of Killington. The land and trails on these 197+/- acres are beautiful and have been used for country skiing and horseback riding. Horse barn with 4 stalls with hay loft above. Riding ring marked by old fencing. 12+/- acres of mostly level pasture. Imagine the trails you could develop on 197+/- acres. Enjoy exploring the pond and three streams that run through the land into Dear Brook. This solid home is expansive and has plenty of large spaces to gather and get cozy with family and friends, or find your own private nook. The kitchen has a breakfast area and an all-season sunroom, and also opens to a large dining area. The living area and library are stately, with hand-selected barn beams and grand fireplaces. The laundry area/mud room is on the main floor, off of the garage. There are four large bedrooms on the second floor: one with a fireplace, two are ensuite, and two share a bathroom. The exterior patio and the peaceful, park-like feel of the property will beg you to sit and relax or hike and explore. 14 strains of daffodils and 40 blueberry bushes! Views of Okemo, Shrewsbury Peak, and Little Killington mountains. Most views are winter from the house, but probably more from the higher part of the property. Near Killington or Okemo skiing. Only 6 miles to Rutland and equally convenient to other services and the airport.

Listed by Sue Starr-Adams of Kelley Real Estate,Inc.

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$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 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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1000 Bear Mountain Camp Road Rupert VT 05776

MLS Number 4908121

  • Residential Single Family
  • Bedrooms 1
  • Construction Existing
  • Zip 05776

Tucked away in the hills of the southern VT town of Rupert, these 135 +/- acres offer amazing mountain views, open fields, orchards & a mature forest! Located at the end of a private, seasonal shared road, the property offers an ideal vacation getaway, hunting paradise or potential homesteader property with 2 +/- acres of open fields, 23 apple trees, 2 streams & a unique off-grid cabin with small ponds nearby. Ready for your finishing touches, the cabin was recently remodeled with a new roof, windows, kitchen, tongue & groove pine interior, hot water sink & shower, stabilized footings & an addition! Siding is not complete & will be the buyer's responsibility. Gated access posted & well-marked with blazes & pins, so you'll know exactly what you own. An excellent wood roads through the property makes ATV & foot access easy. Setup specifically for hunting with food plots, 4 permanent stands & shooting lanes. VAST snowmobile trail access just off the property to the east. Serviced by an outhouse with water brought in for the shower & sink. Heated by a woodstove with wood from the property. Satellite TV & internet with the home setup for a portable generator. Fantastic views of the near & far mountains to the north & west. Just north of Manchester, VT with great shopping, fine dining & skiing. This property may be beautifully rustic but your activities don't have to be!

Listed by Curtis Trousdale and Michael Wrobel of Preferred Properties

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$
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$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 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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1000 Bear Mountain Camp Road Rupert VT 05776

MLS Number 4907955

  • Land
  • Acreage 135
  • Area Rural
  • Waterfront 2400

Tucked away in the hills of the southern VT town of Rupert, these 135 +/- acres offer amazing mountain views, open fields, orchards & a mature forest! Located at the end of a private, seasonal shared road, the property offers an ideal vacation getaway, hunting paradise or potential homesteader property with 2 +/- acres of open fields, 23 apple trees, 2 streams & a unique off-grid cabin with small ponds nearby. Ready for your finishing touches, the cabin was recently remodeled with a new roof, windows, kitchen, tongue & groove pine interior, hot water sink & shower, stabilized footings & an addition! Siding is not complete & will be the buyer's responsibility. Gated access posted & well-marked with blazes & pins, so you'll know exactly what you own. An excellent wood roads through the property makes ATV & foot access easy. Setup specifically for hunting with food plots, 4 permanent stands & shooting lanes. VAST snowmobile trail access just off the property to the east. Serviced by an outhouse with water brought in for the shower & sink. Heated by a woodstove with wood from the property. Satellite TV & internet with the home setup for a portable generator. Fantastic views of the near & far mountains to the north & west. Just north of Manchester, VT with great shopping, fine dining & skiing. This property may be beautifully rustic but your activities don't have to be!

Listed by Curtis Trousdale and Michael Wrobel of Preferred Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 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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$
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$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 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$3,200,000

Est. Mortgage: $/month

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? 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: 5.25% last updated on May 19, 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 2-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: 5.25% last updated on May 19, 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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455 VT Route 30 Winhall VT 05340

Winhall, VT455 VT Route 30

Price$1,850,000

Est. Mortgage: $/month

MLS Number 4893660

  • Land
  • Acreage 174.58
  • Utilities Cable - Available
  • Zoning Residential

A truly one-of-a-kind property offering 174+ acres, ideally located in the heart of Ski Country between Bromley and Stratton Ski Resorts. This very unique parcel consists of a Residential site on 7+ acres with Colonial farmhouse, barn and garage already in place that would make an ideal Guest house or income property. There's an additional 50+ adjoining acres and another 117+ elevated acres with two cleared building sites offering great views. The site located at the top of the 117+ acres borders National Forest and showcases amazing "top of the world" views of Stratton Mountain. This parcel would make an exceptional family compound. For those thinking about developing, we can provide preliminary plans & docs for a 6 to 7 lot subdivision and there's potential for further subdivision. A property like this doesn't come around often so don't miss out on this extraordinary opportunity to enjoy the peaceful beauty and lifestyle Vermont has to offer!

Listed by Josiah Allen Real Estate,Manchester Branch Office

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$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 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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455 VT Route 30 Winhall VT 05340

Winhall, VT455 VT Route 30

Price$1,850,000

Est. Mortgage: $/month

MLS Number 4893614

  • Residential Single Family
  • Bedrooms 3
  • Bathroom 2
  • Construction Existing
  • Zip 05340

A truly one-of-a-kind property offering 174+ acres, ideally located in the heart of Ski Country between Bromley and Stratton Ski Resorts. This very unique property consists of a Colonial with barn and garage on 7+ acres with 50+ acres next door and an additional 117+ acres in the back, bordering National Forest and showcasing top of the world views of Stratton Mountain. The residence has true Vermont charm and allows plenty of room for kids to play in the large meadow located behind the barn. It provides a unique opportunity to stay in residence while building your Vermont Dream home(s) on one or both of the adjoining lots. This would make a great Guest House for family and friends or a nice Ski Rental for additional income. For those thinking of developing this large parcel, we can provide the preliminary plans and documentation for a 6 to 7 lot subdivision. A property like this doesn't come around often so don't miss out on this extraordinary opportunity to enjoy the peaceful beauty and the lifestyle Vermont has to offer!

Listed by Josiah Allen Real Estate,Manchester Branch Office

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$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 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 of Watson Realty & Associates

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$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 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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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

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 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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484 Dawley Road Mount Holly VT 05758

Mount Holly, VT484 Dawley Road

Price$525,000

Est. Mortgage: $/month

Pending

MLS Number 4888133

  • Residential Single Family
  • Bedrooms 3
  • Bathroom 2
  • Construction Existing
  • Zip 05758

New to the market for the first in its history, we present to you The Historic Dawley Farm. If you are looking for an end-of-road location with plenty of open meadows, views and privacy, this is it. The original farmhouse was built in 1860 and has been loved by many generations since. The house consists of 3 bedrooms and 2 bathrooms. The structure is solid and has been minimally maintained but could use some modern updates and TLC. Whether you choose to renovate, move it or start from scratch, the spot cannot be beat. The land is a lovely mix of open meadows and lush woodland, and features a large sturdy barn, all located at the end of a town-maintained dirt road. The family has served this home well for generations but it is time to see what the next chapter holds for this fantastic property on 134 acres. Come take a look.

Listed by Mendi Michael and Gail Beardmore of Engel & Volkers Okemo-Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 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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59 Waite Hill Road Pawlet VT 05761

Pawlet, VT59 Waite Hill Road

Price$725,000

Est. Mortgage: $/month

MLS Number 4885232

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

Words can not describe this gorgeous property- among the most photographed classic farms in Southern Vt. ! With Haystack Mountain providing the back drop, views from every vantage point on the property are stunning! The 153+- acres support 20 acres of active agricultural land, and 16 acres of associated open land suitable for pasturing. The balance of the property is mixed hardwood, hemlock, and white pine forest bordering the North Pawlet Hills Natural Area- owned by the Nature Conservancy. On the north side of a hemlock lined trout brook is a private and spectacular upland meadow, providing more close up views of Haystack and beyond! Pockets of maturing sugar maple provide opportunity for the novice or experienced sugarmakers! The house is in need of TLC and maybe more, but what a great location for an updated farmhouse and heritage estate! Enrollment in the Vt. Current Use program provides reduced property taxes and a sound plan for management of the forest resource! A superb Vermont real estate offering just minutes to the Dorset/Manchester area and Lake St. Catherine!

Listed by Mark Riley Sr of Vermont Forest and Field,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 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 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 May 25, 2022.