LandVest’s Top Places to Gather: Part 2, Thanksgiving in the Country

In late November we gather our family and friends together to celebrate, feast, and give thanks. In this three-part blog series, we’ll explore LandVest’s favorite places to celebrate Thanksgiving by the sea, in the mountains, and in the country.

These are some of our favorite country estates large enough to host the whole family. With rolling lawns to toss the pigskin around on, walk/jog trails to work up an appetite on, and large rooms to fill, these properties are Thanksgiving ready.

75 Goodnow Road

Sudbury, MA
Country Thanksgiving: 75 Goodnow Road
Set back from the road on a gentle rise, 75 Goodnow Road is a custom-designed, classic Georgian with spacious rooms perfect for family gatherings. Everyone can enjoy the lower-level entertainment room, game room, exercise room, media room, wet bar and wine cellar, and walk out to multiple patios and a fire pit.

38 Gardner Street

Hamilton, MA
Country Thanksgiving: 38 Gardner Street
Sited on over 11 private acres of lawns and meadows in the heart of Hamilton, the original 18th-century farmhouse has been gracefully expanded to be open and bright. The property has direct access to the Essex County Trail Association and is within an easy train or auto commute to Boston.

Wardwell Point

Penobscot, ME

Country Thanksgiving: Wardwell Point Country Thanksgiving: Wardwell Point

Wardwell Point features sweeping meadows and 900± feet of meandering shorefront on the Bagaduce River, a tidal estuary of Penobscot Bay. This 18± acre property offers exceptional privacy, seclusion, and a classic pastoral setting. The splendidly restored barn features a light-flooded great room, a massive stone fireplace , a bank of 30′ tall windows offering views over the flowing waters and four bedrooms providing ample room for holiday guests.

Seth Hill Homestead

In the Heart of the Green Mountains
Country Thanksgiving: Seth Hill Homestead
Seth Hill Homestead is a secluded 761-acre family compound with 3 completely private residences. 180-degree mountain views and protected woodlands that surround, are just a few of the assets of this classic Vermont Hill farm property. Located at the end of a private road, Seth Hill Homestead is not only stunningly beautiful, but enjoys complete privacy, miles of trails, streams, waterfalls, old stone walls, and lies at the southern end of a vast area of conserved land.

Southmayd Farm

Stockbridge, MA

Country Thanksgiving: Southmayd Farm Country Thanksgiving: Southmayd Farm

This 1870 Berkshires estate has been fully restored and is privately sited on 33+ acres within walking distance of town. The 8,500 sq. ft. main house includes 8 bedrooms and is complemented by a carriage house, greenhouse, guest house, studio, barn complex and paddocks, and so much more. A spectacular location brings generations of family together for the holidays.

Copper Beech Hill

Wenham, MA
Country THanksgiving: Copper Beech Hill
Located next to the world-renowned Myopia Hunt and Polo Club, this hilltop, turn-of-the-century, 24.14-acre estate is a combination of woodlands, open fields, and rolling lawns, featuring bridle trails, stone walls, and large specimen trees.

Pirate’s Cove Farm

Mount Desert, ME

Country Thanksgiving: Pirate's Cove Farm Country Thanksgiving: Pirate's Cove Farm

Set on 6.53± acres and overlooking a quiet saltwater cove in the neighborhood of Pretty Marsh, Pirate’s Cove Farm is known to be the oldest residence in the town of Mount Desert. The warm and inviting home is perfect for holiday gatherings, with three bedrooms and three and a half baths, formal living and dining rooms, a spacious family room, long outdoor terraces and a two-story barn that could be renovated to be a guest residence or studio space.

Alewive Road Farm

Kennebunk, ME
Country Thanksgiving: Alewive Road Farm
In the prettiest of Maine’s country settings, Alewive Road Farm offers 73+ acres of rolling fields, pastures, and a sparkling pond. With the rare combination of convenient access and privacy, the property consists of an authentic farmhouse, grand barns, and various outbuildings. Currently a certified organic farm, next Thanksgiving will feature your own cultivated farm-to-table feast from soup to nuts.

50 East Road

Alford, MA
Country Thanksgiving: 50 East Road A meandering drive through a hardwood forest leads to this 11,800-sq-ft family retreat in the Berkshires. The wood-shingled home was built in 2003 on a ridge near the center of the quaint village of Alford. The property is handicap accessible, includes a home theater, game room, workout room, and wine-cellar.

The Morewood

Pittsfield, MA

Country Thanksgiving: The Morewood Country Thanksgiving: The Morewood

The Morewood is a masterpiece of historical restoration, every room draws you in to a place where guests are treated like family. The 10,000+ sq.-ft. Tudor-style brick main house has plenty of room for hosting friends and family.

Upton Pond

Stoddard, NH
Country Thanksgiving: Upton Pond
Plenty of room for friends and family to gather for the holidays and enjoy meals overlooking Upton Pond,  the 9.8-acre centerpiece of this 1,318 private retreat in Southern New Hampshire. The 3-bedroom main house is built of the finest materials including mahogany, teak and cedar, thoughtfully designed for maximum solar gain, water and mountain views. Pond-side cabin, and 3 apartments provide additional space.

Upper Farm

Barnard, VT
country thanksgiving: Upper Farm
Upper Farm, is a classic 4 bedroom, c1799 center-chimney Cape on 12± acres in Barnard that has been completely renovated and is an exceptional family-friendly retreat designed to celebrate the Vermont lifestyle inside and out.

For more information on these and other LandVest luxury properties, visit or call our Boston office, (617) 723-1800.132