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: 2.97% last updated on Apr 22, 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: 2.97% last updated on Apr 22, 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: 2.97% last updated on Apr 22, 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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466 Marcia Lane Dorset VT 05251

Dorset, VT466 Marcia Lane

Price$2,900,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4744398

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

Dorset Hollow Pinnacle offering 180 trail laced acres at the height of the Dorset's Upper Hollow Road. Amazing Sunsets... Stunning Long Range Mountain Vista's are captured immediately from the impressive foyer and continues to captivate from room to room throughout this architect designed residence! With over 7500 light filled square feet this gracious residence with lovely custom cabinetry and crown moldings supports Vermont living at it's finest! Massive Stone fireplace walls grace the cherry paneled library as well as the 50 X 22 expansive Great Room Kitchen featuring an incredible breakfast room and a Honed Costa Esmeralda island, Wolf appliances and handsome coffer ceiling for the living/dining. Just off the kitchen are the well planned wet bar, wine cellar and pantries. Warm radiant heated hardwood floors lead to the 3 room primary suite that includes sitting rm/office, exercise room and luxury bath with relaxing soaking tub or shower. 4 bedrooms and baths up comfortably accommodate guests and family. A bonus room integrates nicely for full time use supporting any hobby or media interest. Full light filled basement and Carriage house offers expansion for guest quarters within the generous floor plan if desired. Over-sized garages, attached or detached offer room for all the toys! Raised stone terrace creates indoor / outdoor ease for all living areas that offers heated path to the spa, grilling area & outdoor fireplace. This property meets field and stream perfection!

Listed by Josiah Allen Real Estate, Inc.

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$/month over payments
Federal 30-year interest rate: 2.97% last updated on Apr 22, 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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871/873 Stratton Arlington Road Stratton VT 05155

MLS Number 4803359

  • Residential Single Family
  • Bedrooms 6
  • Bathroom 7
  • Construction Existing
  • Zip 05155

Spectacular Stratton, Vermont multi-home private estate on 32 acres with two sensational secluded mountain top homes. Bordered by thousands of acres of National Forest lands, this secluded setting offers serenity, relaxing tranquility and magnificent panoramic views, yet is conveniently located only 15 minutes from either Stratton or Mt. Snow ski areas. A private paved road leads up to the two fully furnished luxurious homes that offer unsurpassed quality craftsmanship, state of the art energy efficiency and high tech security systems. Each home has radiant gas heat, air conditioning and whole-house backup generators. The exquisitely designed 8,800 sq. ft. main home features 5 bedroom suites, 6-1/2 baths, 5 stone fireplaces, 2 laundry rooms, a caretaker's apartment, hot tub room, sauna room, home theater, wine room and a 3-1/2 car garage. The Vermont Energy Star 5,200 sq. ft. guest home features 5 bedrooms, 4-1/2 baths, 2 stone fireplaces, hot tub room, 12 zone distributed audio/video system and a 2-1/2 car garage. Plenty of room is available on the property for a tennis court, swimming pool and even a helicopter pad. Call today to make an appointment to see this extraordinary one of a kind private and secluded family sanctuary. These properties are individually listed as well, 871 MLS#4782252 and 873 MLS#4780640.

Listed by Richard Caplan of Deerfield Valley Real Estate

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$/month over payments
Federal 30-year interest rate: 2.97% last updated on Apr 22, 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$2,650,000

Est. Mortgage: $/month

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: 2.97% last updated on Apr 22, 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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1108 West Hill North Road Jamaica VT 05343

Jamaica, VT1108 West Hill North Road

Price$2,450,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4821154

  • Residential Single Family
  • Bedrooms 8
  • Bathroom 8
  • Construction Existing
  • Zip 05343

BETWEEN HEAVEN AND EARTH A NURTURING HAVEN FROM THE WORLD YET 3 MINUTES TO STRATTON MOUNTAIN ACCESS ROAD: Spectacular panoramic vistas of mountain ranges and country valleys under a sweeping sky from this magnificent ski country estate on 99 private acres. A scenic driveway wends its way past a lighted skating pond with warming hut and heated paddle tennis court to the timeless 8 bedroom, 8 bath main residence on a sublime serene hillside setting. A captivating 3 bedroom, 2 bath guest apartment is secluded above the detached 3-bay garage. Spaciousness, comfort , convenience define the open living areas with access onto expansive viewing porches, patios and winterized sun porch. Designed for ease of entertaining and a restorative retreat for the few or many, the main level master suite and en suite guest bedrooms provide restful privacy. Steps from the house, under the stars, is a glass enclosed gazebo with hot tub. Stone walls with perennial gardens enhance the harmonious natural landscape. A world unto itself and still close to Stratton Resort.

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

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$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Apr 22, 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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$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Apr 22, 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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455 VT Route 30 Winhall VT 05340

Winhall, VT455 VT Route 30

Price$1,995,000

Est. Mortgage: $/month

MLS Number 4844261

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

A truly one-of-a-kind property offering 175(+/-) 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 acre 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, Inc.

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$
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$/month over payments
Federal 30-year interest rate: 2.97% last updated on Apr 22, 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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Birdseye Road Castleton VT 05735

Castleton, VTBirdseye Road

Price$1,900,057

Est. Mortgage: $/month

MLS Number 4839121

  • Land
  • Acreage 607.34
  • Utilities None
  • Zoning None

This is YOUR chance to own over 600+ Acres of Vermont Paradise, Former Birdseye Mountain Ski Resort (1324' Vertical Drop). This property is perfect for back-country enthusiast such as skiers, hikers and mountain bikers, hunters and more. Castleton River access, great location. Huge Development Potential Private or Public Ski/ MTB Resort Potential Minutes to Rutland Regional Airport (RUT) AMTRAK Station (CNV) a mile away 1 Mile to Charming Castleton VT Village/ University and Major HWY VT RT 4 Let your imagination run WILD!

Listed by Tucker Adirondack Lange of KW Vermont-Killington

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$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Apr 22, 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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4263 Main Street Manchester VT 05254

Manchester, VT4263 Main Street

Price$1,850,000

Est. Mortgage: $/month

Pending

MLS Number 4786375

  • Residential Single Family
  • Bedrooms 4
  • Bathroom 6
  • Construction Existing
  • Zip 05254

"Glebelands", a 28.75 acre Manchester Village Estate, dramatically sets itself apart by a magnificent water setting, offering an extraordinary spillway cascading back into the Munson Brook that feeds a lovely swimming pond where the stream flow meanders out the property ultimately feeding the Orvis Fishing Pond. The exceptionally well proportioned 4 BR, 5.5 Ba estate residence offers beautiful architectural details throughout the Living room, Dining room and Study each with fireplace; the Danby marble kitchen with two additional wet bars/ prep areas that offer an unusual open butlers pantry set up perfectly for entertaining or peaceful cook's enjoyment. Old world meets today with an award winning architect-designed "great room" with perfectly centered fireplace, vault, window walls and built-ins, that lead to a breakfast nook. Upstairs can be approached by elevator or one of two staircases. There is a true old world master bedroom suite with balcony, dressing room, closets, dressing table alcove, and marble accented bath, three additional bedrooms each with adjacent baths. The carriage house boasts a 2 BR and 1 BR apartment each with fireplace. Playful outbuildings such as the radiant heated folly or playhouse. The unique grounds are defined by specimen plantings, orchard, and hidden gardens with reflecting pools and fountains that truly speak to an era of significance. "Glebelands" is Manchester's stroll through an opulent history.

Listed by Josiah Allen Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Apr 22, 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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East Mountain Road Killington VT 05751

Killington, VTEast Mountain Road

Price$1,650,000

Est. Mortgage: $/month

MLS Number 4853400

  • Land
  • Acreage 28.18
  • Utilities None
  • Zoning PUD

This is a unique opportunity to purchase a 28+ acre PUD offering direct ski in ski out access to Killington ski trails. Some sites would access the Great Eastern ski trail, while others would access Home Stretch. Seven homesites with individual wells to be drilled and 4-bedroom mound septic systems to be built have been designed and an 8th parcel of common area together received town and Act 250 approval in 2016. Because no building has begun, this permit would need to be renewed before work could begin. All design and permit documentation has been recorded and is publicly available. Think of the possibilities. Call now for more information and/or a tour of the property.

Listed by Heidi Bomengen of Prestige Real Estate of Killington

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Apr 22, 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 April 23, 2021.