Splurge vs. Steal Resort Edition: Woodstock, Vermont

Our Steal: 327 Fletcher Schoolhouse Road, Woodstock, Vermont, is currently listed by Carol Wood of Williamson Group Sotheby’s International Realty for $2.7 million.

What’s better than a year-round destination offering picturesque beauty and timeless New England charm? How about being centrally located on the banks of the Ottauquechee River and at the crossroad of the Vermont Scenic Byway? Add some Windsor County Green Mountain views, and it’s easy to see why today’s Splurge vs. Steal is situated in idyllic Woodstock, Vermont. We’ve located two incredible Woodstock retreats, both with impressive acreage and stunning architectural styles but with price points that are miles apart. Which one would you choose? The hilltop classic splurge or the charming Bybrook Farm steal? Be sure to let us know in the comments!

Splurge: Luxurious 30-Acre Hilltop Home With Mountain Views For $5.45M

Nestled at the peak of a private road on a hilltop with long-range views of Vermont’s Green Mountains sits this impeccable six-bedroom, eight-bathroom estate on 30.39 rolling acres. The land itself is a real stunner with lush woodlands and miles of John Morton trails. Natural foliage surrounds the home to create the ultimate in privacy, met by a landscaped lawn and sparkling swimming pool.

Fully renovated in 2016, we are in love with the gorgeous interiors.

Starting with the stunning sun room and working our way in, it’s easy to be swept away by the abundance of natural light that fills the home.

A loaded gourmet kitchen anchors the home, bringing together a classic clean color palette with modern appliances. Double ovens, a gas range, wine cooler, walk-in pantry, and mountain views make this the place to entertain family and friends or host a romantic night in for two.

Nearby, walls of picture windows illuminate an inviting living room with cozy stone fireplace.

A private office with custom built-ins offers a secure space for those who work from home, while the personal gym is a convenient retreat when you need to relieve the stresses of a long day.

Each of the property’s six bedrooms are warm and inviting, including the spa-like bathrooms which will keep all your guests comfortable during their stay.

An added bonus? The entire house is wired with smart-home technology featuring the ability to control lights, temperature, shades, and more from an iPad.

If you’re looking for a Vermont vacation home or private residence, this seasonal beauty is tough to beat.

Chris Lang with Landvest Inc. has listed 0 Westerdale Rd, Woodstock, Vermont  for $5.45 million.

Steal: Picturesque Country Estate For $2.7M


For half the price of our splurge you could be living on Bybrook Farm. This historic country estate — originally built in 1797 — has since been fully renovated and transformed into the perfect retreat.

Sited on 26 acres, the property is surrounded by a tranquil combination of brook, pond, rolling hills, forests, and mature gardens.

A quick walk from the historic hamlet of South Woodstock and acclaimed Green Mountain Horse Association equestrian center are just a few of the incredible amenities the estate has to offer! Nearby golf, tennis, skiing, and more, means you’ll never run out of things to do.

Historic integrity played a significant role in the property’s complete restoration and is apparent in the custom cabinetry and finishes, hand-hewn beams, reclaimed wood floors, and deluxe amenities.

We love the two separate kitchens with warm woods, bead board, ample shelving, and stainless steel appliances. Each room on the estate offers endless entertainment options with family and friends.

Wide open dining areas offer plenty of space to host memorable dinner parties, while a separate wine room with storage is available for serving your favorite vintage on special occasions. In the formal dining, a striking decorative painting comes complements of renowned artist Kevin Paulsen.

You’ll also enjoy five bedrooms in the main house, all bedecked in gorgeous windows with breathtaking nature views. A free-standing tub and separate shower complete the master suite, allowing for modern luxury in this historic retreat.

And a separate guest house means ample space without the slightest chance of getting crowded! The hardest part will be choosing which part of the property you love the most. Light and airy, or warm and rustic? It has both!

Relax on the stone terraces or open-air porches and take in the sounds of the rolling brook that flows throughout the property. Take a dip in the accompanying pond or have your pick of numerous entrancing nature walks to wind down.

Complete with charming farmhouse, a classic wooden bridge, and Vermont red barns, this estate is the epitome of elegant New England-style living.

Carol Wood of Williamson Group Sotheby’s International Realty has listed 327 Fletcher Schoolhouse Road, Woodstock, Vermont for $2.7 million.