Luxury Properties for sale in the Bennington County (VT)

A rare gem and historically significant property in the picturesque setting of Manchester Village. Available for the first time in over 40 years! The embodiment of timeless...

Presented by Greg Cutler | Four Seasons Sotheby's International Realty

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...

Presented by Chris DeFelice | Four Seasons Sotheby's International Realty

Hidden at the top of one of Dorset’s quiet lanes you will discover the epitome of timeless elegance & modern luxury in this meticulously renovated 5-bedroom, 6-bathroom 1941...

Presented by Richard Slocum | Four Seasons Sotheby's International Realty

Welcome to High Fields: A Custom-Built Sanctuary in Southern Vermont. Arrive via a private, maple-canopied lane to discover tranquility & breathtaking mountain views. This home...

Presented by Andrea Kaplan | Four Seasons Sotheby's International Realty

Welcome to 376 Windward Hill: A sprawling estate with spectacular views of the Taconic and Green Mountain Ranges. Nestled in the heart of Southern vt, this extraordinary property...

Presented by Sean Dillon | Four Seasons Sotheby's International Realty

Danby Mountain Road Sanctuary - Very private estate on 23.90 level acres, includes: beautiful main house, inviting guest house, detached barn (25x20), pond, open fields/meadows,...

Presented by David A. Halligan | Four Seasons Sotheby's International Realty

Discover the perfect blend of luxury, sophistication and convenience in this stunning custom built property. Ideally situated in one of Vermont???s favorite winter and summer...

Presented by Adrienne Sherwood | Four Seasons Sotheby's International Realty

The Manchester residence on Canterbury Road is gracefully elevated on a landscaped 2.81-acre end-of-road setting, offering both tranquility and convenience to nearby amenities,...

Presented by Andrew Reed | Four Seasons Sotheby's International Realty

Classic three bedroom Post & Beam design built in 2001 by Mert Cross with open floor plan, cathedral ceilings, and reclaimed chestnut hardwood flooring offered on private 13.26...

Presented by David A. Halligan | Four Seasons Sotheby's International Realty

Nestled at the end of a quiet cul-de-sac, this iconic turn-of-the-century Vermont farmhouse exudes timeless charm and character. With its signature clerestory windows, an...

Presented by Hayley VanDerKar | Four Seasons Sotheby's International Realty

Southern Vermont offers incredible value with a wealth of outdoor activities, events, and artistic venues. Located on Bromley Mountain with Stratton, Magic, and Okemo Mountains...

Presented by Nancy Jensen | Four Seasons Sotheby's International Realty

Discover the charm of this Post and Beam style country home, designed for creating lasting memories! Nestled in a peaceful, private setting with abundant apple trees, this...

Presented by Andrew Reed | Four Seasons Sotheby's International Realty

Escape to your own private oasis with this stunning 67-acre estate nestled amidst nature's embrace. With winding trails, babbling streams, and serene woodlands, this property...

Presented by Adrienne Sherwood | Four Seasons Sotheby's International Realty

Rejuvenate your mind, body, and soul at your very own Vermont sanctuary. Over 40 acres of open meadows, rolling hills, fruit trees, berry bushes, stone walls, and a mature forest...

Presented by Carol O'Connor | Four Seasons Sotheby's International Realty

Enjoy all Vermont has to offer year-round! This sun filled home is tucked away in Peru on 10 acres of land offering beautiful mountain views and a private pond with a beach, deck,...

Presented by Tatsiana Clark | Four Seasons Sotheby's International Realty