4 Historic Homes You’ll Fall in Love With

You don’t necessarily have to be a history buff or a vintage enthusiast to have a soft spot for historic homes. The beautiful and intricate details, impressive craftsmanship, striking architectural styling, and bygone-era charm are enough to win over nearly any potential homebuyer. 

If you have your heart set on living in a cozy Victorian, Colonial-era farmhouse, or picket-fence charmer, the Connecticut/Massachusetts region is a great place to house hunt. Historic homes are frequently on the market in this area — and many of them pair those great historic exteriors with renovated interiors that have been updated for modern living. 

 Here are four listings currently on that market that will satisfy your historic home craving:

A Berkshires “Grande Dame”
17 Prospect Hill Rd | Stockbridge, MA | $4,450,000

Built in 1900 as one of the “cottages” in the Prospect Hill area, this Federal-style stunner is magical in the fall. Leaf peeping is a breeze from the wraparound glass porch and south- and west-facing views throughout the home, and it’s easy to get cozy in front of the home’s four fireplaces, complete with antique details. Boasting 4 bedrooms and 4.1 baths with 6,000 sq. ft. of space on 15+ acres, the home offers plenty of room to roam. The interior spaces perfectly combine historic charm with modern conveniences such as an updated chef’s kitchen as well as bonus spaces like a large game room. A massive circular staircase descends from the home’s back exterior to an outdoor entertaining area that includes a Gunite pool, golf tee/driving area, and a walled stone garden.

A Very Fine Farmhouse
24 & 30 Berkshire Heights Rd | Great Barrington, MA | $4,900,000

Historic farmhouse enthusiasts will rejoice at this nearly 50-acre historic estate with jaw-dropping views in Great Barrington. Designed by Charles Platt for Charles Freer of the renowned Freer Gallery in Washington, DC, this 4 bedroom, 3.1 bath home was constructed in 1918 of stone quarried from the property. Its rambling, one-floor layout offers 6,240 sq. ft. of living space, including a large, comfortable living room with views from massive windows, a book-lover’s dream of a library, and an elegant dining room — all with fireplaces. A lovely stone patio is the perfect spot to enjoy the luscious views. The property also includes a stable and riding ring, pool, orchard, vineyard, and two fully equipped guest houses plus caretaker’s home.

A “Ten” on the Town Green
878 Longmeadow | Longmeadow, MA | $1,300,000

Built in 1795, but completely redone for today’s tastes, this spectacular 7 bedroom, 3.1 bath, 5,100 sq. ft.  home on the town green looks like it stepped right out of a movie set. Classic floor-to-ceiling windows and shutters articulate the to-die-for wrap-around front porch, flanked by columns with decorative millwork. Period details continue throughout the exterior and interior: dental trim, tray ceilings, leaded glass cabinet fronts, and wood-burning fireplaces. The beautifully renovated interior boasts a stellar kitchen with Wolf appliances, granite countertops and a Carrera marble island plus many other stylish rooms.

Picket-Fence Picture-Perfect
25 Main St | Essex, CT | $2,750,000

The ultimate in Americana living, this picket-fenced home right on Main Street embodies the small-town charm of days gone by. The 4,507 sq. ft. 1820 Colonial with 5 bedrooms and 4.2 baths delights at every turn with fun flourishes like Zebra-patterned wallpaper in the powder room, a diamond-paned wood floor in the sun room, and a sunny breakfast nook in the kitchen. A recent renovation joined the main home and the carriage home for full modern living with standout spaces including a double-height living room, library, remodeled kitchen, and private courtyard terrace. This true historic dream home is located close to town and the water.

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