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

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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

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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

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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

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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

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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

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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

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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

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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

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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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