Behold the 5 Oldest Homes for Sale in America


As we prepare our Thanksgiving table, our thoughts might turn to the very first people who started the American holiday. There’s one fascinating fact you might not think about: The settlers sure knew how to build a shelter back then.

In fact, some of the homes that were built during the 1600s are still standing, and some are even on the market.

In the spirit of the season, we did some sleuthing and found the five oldest homes for sale in America right now, in good living condition, despite being built not too long after the first Thanksgiving in the 1600s!

One is a grand riverfront estate, another is a quick commute by boat to Boston, and still another has a tavern on the property. How fun is that?

Whether they encourage you to be grateful for your own, more modern living accommodations or inspire you to explore living in a Colonial-era dwelling, you’ll have fun feasting your eyes on these unique properties.

1224 Main St, Glastonbury, CT

Price: $369,999
Terrific transplant: Constructed in 1682 in Bradford, MA, by John Hall as a house of refuge against attacks, this two-bedroom, center-chimney Colonial was moved to its present location near the historic village of Glastonbury in 1974.

The property includes a barn that is currently in use as a garage, a smokehouse, and the original Colchester Tavern, built in 1705, which was relocated to the property in the 1970s.

The main house, which measures 1,774 square feet, has original features that have been preserved and restored, including millwork, flooring, diamond-paned windows with leaded glass, and three working fireplaces.

Although there is new electrical, plumbing, and HVAC and the bathrooms have been updated, the home is still in need of some restoration. With a little elbow grease, you’ll have a home like no other.

Glastonbury, CT(


661 Main St, Medfield, MA

Price: $569,000
Lucy Bran House: It’s hard to believe this cozy cottage has been standing since 1670, especially when you set foot inside and see a large, beautifully updated kitchen with a granite-topped dining island and stainless-steel appliances.

The three-bedroom, two-bath cottage still has plenty of Colonial-era charm. Details include original ceiling beams, beautiful wide-plank hardwood floors, wood paneling, and granite steps and stone walls on the 8,716-square-foot lot.

The detached, two-level barn fits one car on the lower level.

To accommodate modern living, all of the bathrooms have been redone and the place comes with a laundry room with a washer and dryer, a separate study, and a wood-burning stove.

The charming downtown of Medfield is only a half-mile away.

Medfield, MA(


162 Cherry St, Wenham, MA

Price: $1,050,000
Newman-Fiske-Dodge House: Standing since 1658, the 4,000-square-foot Newman-Fiske-Dodge House has oak wood beams, paneled walls, brick fireplaces, and a barn from the era.

This landmark home is listed on the National Register of Historic Places. It includes five bedrooms and 3.5 baths, plus a bright kitchen (thanks to a newer skylight) where you can cook on a modern gas stove or an older pot-bellied stove.

Bonus rooms include a flexible third-floor loft, which could be used as an office. There’s also a formal dining room and an enclosed porch.

Wenham, MA(


46788 Glen Mary Farm Rd, Park Hall, MD

Price: $3,999,000
Glen Mary Farm: This nearly 400-year-old beauty certainly doesn’t show its age. The original Colonial builders would be astounded to see what the 200-acre, waterfront property has become since its origin as part of the first permanent settlement in Maryland in 1654.

This unique estate offers 13,691 square feet of living space, a deep-water pier, a pool, a full mile of shoreline on St. Mary’s River, five barns with 30 horse stalls, and more than 100 acres of fenced pasture land.

The six-bedroom grand manor retains some Colonial elements, including brick imported from England, fireplaces, some doors, and paneling.

There are six more residences on the property, including an annex, two barn apartments (fully furnished), plus the Duck House, a cottage, and a log cabin—which need to be renovated. Possibilities for the property include farming, ranching, rental income, and holding special events.

The price has been reduced by over $1 million since it was initially listed in 2021.

Park Hall, MD(


116 Spring St, Hull, MA

Loring House: Built circa 1633, the Loring House is the oldest U.S. home on the market. Features that appear to be original include its four fireplaces, paneling, wide-board pine floors, and beamed ceilings.

The Cape-style cottage features two bedrooms and 1.5 baths, plus a small study, a living room, a dining room, an open kitchen with an island, two staircases, and a newer furnace, to keep you warm during those harsh New England winters.

There’s also a two-car garage with a loft that could be converted into a workroom or studio.

This place is located within walking distance of a pier where you can catch the commuter boat to Boston.

Hull, MA(

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