Charming Classic on Cape Cod From 1720 Is the Week’s Oldest Home

Recent decor trends have placed a premium on an uncluttered and unassuming beige aesthetic. Maybe that’s why it’s so refreshing—dare we say thrilling!—to see colorful, centuries-old homes filled with one-of-a-kind spaces.

The oldest homes to land on the market this week include a charmer with robin’s-egg blue shutters and trim set against classic gray shingles, a couple of red barns with crisp white edges, and a bright teal door adorning a black and white Colonial beauty.

And as far as interiors go, there are nooks and crannies galore, plus formal libraries, walls of windows, and even a temperature-controlled conservatory to shake up the status quo.

Located on Cape Cod, this week’s most senior structure just celebrated its 300th birthday. Join us on a trip back through the centuries and count down all of this week’s 10 oldest homes.

1. 1866 Main Rt 6A St, West Barnstable, MA

Price: $475,000
Year built: 1720
Renovated Cape: Built before the country was founded, this charmer on Cape Cod boldly enters its fourth century in America, and it’s ready for a new owner to move right in.

The two-bedroom home has been lovingly restored, yet still maintains its original charm with wide-plank floors and a huge fireplace. It sits on an acre that includes a barn for storage and parking, specimen trees, and a garden.

West Barnstable, MA


2. 533 Weed St, New Canaan, CT

Price: $1,295,000
Year built: 1720
Seth Weed Chapman-Martin house: Renovated into a ravishing antique home, this five-bedroom prestige property is the second-oldest residence in this classic Connecticut town. It now boasts a new kitchen and bathrooms, radiant floor heating, three fireplaces, and an in-ground pool.

New Canaan, CT


3. 665 Summer St, Duxbury, MA

Price: $639,000
Year built: 1725
Airy antique: Substantially rebuilt a decade ago, this three-bedroom home is now an airy modernized family residence chock-full of history. With over an acre in property, there’s tons of room to spread out. It also sits close to the 300-plus-acre Lansing Bennett Forest trails system.

Duxbury, MA


4. 23 Altamont Rd, Millbrook, NY

Price: $3,950,000
Year built: 1728
Grace Hill Farm: Only part of this rural property in Dutchess County dates to 1728. The rest is a modern horse lover’s dream.

The 85-acre equestrian facility includes a tricked-out barn with a heated indoor arena, viewing lounge with chef’s kitchen and dining space, 14 stalls, tack room, outdoor jumping area, dressage arena, and turnout paddocks.

Millbrook, NY


5. 1905 Elm St, Dighton, MA

Price: $520,000
Year built: 1730
Contemporary Colonial: Although it was built nearly 300 years ago, the interiors of this three-bedroom home have been modernized without sacrificing an iota of vintage charm.

The structure’s roots as a tavern and church parsonage are evident in its substantial woodwork, wide-plank pine floors, and large fireplaces. Natural light and thoughtful modern updates make it ready for a 21st-century buyer.

Dighton, MA


6. 1735 Hunterbrook Rd, Yorktown Heights, NY

Price: $1,195,000
Year built: 1735
Turtle Hill: Built as a tenant farm, today this 4-plus-acre property features a lovingly restored four-bedroom home with original wide-plank floors and a custom kitchen. Outside, there’s an in-ground pool surrounded by a travertine patio, barn, one-bedroom studio with kitchenette and bath, gardens, an heirloom apple orchard, and temperature-controlled conservatory.

Yorktown Heights, NY


7. 5 High Ridge Rd, Pound Ridge, NY  

Price: $599,000
Year built: 1735
Jones Homestead: Adjacent to the 26-acre Bye Preserve and across from the Pound Ridge Golf Club, this parklike property has a four-bedroom Colonial farmhouse in need of a little love. Highlights include wide-plank floors, a brick fireplace, and exposed beams. Outside, there’s a wraparound porch, lawn, sheds, a pond, and woodlands.

Pound Ridge, NY


8. 40 N Court St, Providence, RI

Price: $860,000
Year built: 1737
College Hill: Owned by several architects over the years, this well-preserved three-bedroom home was described in early documentation as “sturdily built” and is the oldest home in the area.

Highlights include wide-plank pine floors, sidewinder staircases, exposed beams, and a brick fireplace. Outside, there’s a covered brick patio with views of the statehouse.

Providence, RI


9. 1062 North St, Walpole, MA

Price: $899,000
Year built: 1740
Tremendous teal door: Stately and stylish, this updated four-bedroom Colonial sits on nearly 2.5 acres adjacent to a 500-plus-acre conservation area. Highlights include a recently updated kitchen, fireplaces in nearly every room, and a third-floor room with skylights and loads of closet space.

Walpole, MA


10. 335 River Rd, Carlisle, MA

Price: $1,295,000
Year built: 1745
Pastoral and peaceful:  Located north of Boston, this classic four-bedroom home features gunstock beams, a center chimney, four original brick fireplaces, and multiple updates throughout. The 5-acre property is filled with gardens and fields.

Carlisle, MA

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