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Perched atop this week’s list of oldest homes on the market is an exquisitely preserved Colonial in Massachusetts dating to 1690. Right next to the waters of Gloucester Harbor, this beautiful old-timer has been updated in all the right places.

The rest of the week’s 10 oldest homes also have a claim to pre-Revolutionary War history, but thanks to strategic face-lifts, many are looking better than ever in 2021.



But if you’re in search of a renovation project, there are a couple of opportunities. A 14-acre estate with a farmhouse and stocked pond dating to 1750 is headed to the auction block with a low opening bid. There’s also a Colonial in Pennsylvania sitting on land that dates to the original William Penn land grant.

So take a stroll back in time and tour this week’s 10 oldest homes.
1. 1 Old Salem Rd, Gloucester, MA
Price: $699,000
Year built: 1690
New England treasure: This Colonial just up the road from Boston strikes a wonderful balance between smart preservation and modern updates.

Many of the home’s original features are still intact, including the floorboards and a parson’s cabinet. More recent updates to the three-bedroom residence include a modern kitchen and bathroom, central air conditioning, and fenced garden.
Gloucester, MA


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2. 719 Prince District St, Georgetown, SC
Price: $657,500
Year built: 1721
Thomas Bolem home: One of the oldest taverns still standing in South Carolina, this home has been extensively renovated and now boasts a modern kitchen and bath.

Additional highlights of the four-bedroom home include front porches on both levels, an outdoor piazza for gathering, and close proximity to shopping and dining. Currently used as a vacation rental, the home maintains a five-star rating among guests.
Georgetown, SC


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3. 313 Umpawaug Rd., Redding, CT
Price: $1,199,000
Year built: 1723
Horsefeathers: Once home to Revolutionary War Col. Aaron Barlow, this graceful saltbox sits on a knoll and is surrounded by 2 acres that hold a pool, gardens, stone walls, and terraces. Indoors, the four-bedroom home still has its original wide-board chestnut floors and antique beams, modern baths, and two unfinished bonus spaces.
Redding, CT


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4. 161 Wallis Rd, Rye, NH
Price: $1,595,000
Year built: 1725
Rand family homestead: Minutes from downtown Portsmouth and beaches, this property includes a lovingly maintained four-bedroom home that has had only three owners over the past three centuries.

Period highlights include wide-plank pine floors, kings pine shiplap wainscoting, and a wood-burning fireplace. Updated areas are highlighted by a modern country kitchen, loft, and private yard with outdoor shower.
Rye, NH


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5. 521 Elsie St, Reading, PA 
Price: $479,900
Year built: 1745
Picture-perfect: Situated on more than an acre—on part of the original William Penn land grant—this five-bedroom Colonial has been modernized with a new kitchen and bathrooms.

It also includes throwback touches like an original bake oven fireplace, workshop, as well as a root cellar converted into a wine cellar. There’s also a third-floor area that would make an excellent studio or guest accommodations.
Reading, PA


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6. 31 Old State Rd, Epping, NH
Price: $641,500
Year built: 1745
Rockingham County: This classic post-and-beam New England Colonial has been expanded twice: once in the 1800s, and again in 2006.

Today, the four-bedroom home offers a spacious 3,953 square feet of living space. Standout features include the beehive double-sided fireplace in the living room and a two-story attached barn.
Epping, NH


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7. 16541 Dolf Rd., Stewartstown, PA
Price: $175,000
Year built: 1750
Auction-ready: Get your paddle ready, and put in a bid on this three-bedroom antique sitting on just over 14 country acres. It boasts a covered front porch, wood stove, renovated kitchen, and walk-up attic. The acreage offers plenty of room to expand.

And there’s still time to get your finances together—the auction is scheduled for May 7, and the current list price is just a suggested opening bid.
Stewartstown, PA


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8. 122 Walker Rd, Washington Crossing, PA
Price: $1,450,000
Year built: 1750
Pre-Revolutionary in Bucks County: The owner of this five-bedroom classic updated the interiors while maintaining timeless touchstones.

You’ll see original wide-plank floors, lovely high ceilings, exposed beams, and beveled-glass windows. The 3-acre property also includes a barn with a second-floor entertainment space equipped with air conditioning and heating.
Washington Crossing, PA


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9. 1369 Old Chapel Rd., Boyce, VA
Price: $480,000
Year built: 1750
Clarke County: One of the most historic homes in the area, this lovely Federal Georgian–style residence has a rich history, including service as a local tavern.

Nowadays, this three-bedroom home comes with a renovated kitchen, four wood-burning fireplaces, heart pine flooring, and original hardware. There’s also a lush lawn, fire pit, and two porches for outdoor living and entertaining on over a full acre.
Boyce, VA


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10. 6089 Lower York Rd, New Hope, PA
Price: $895,000
Year built: 1750
Mixed use: Zoned for commercial or residential use, this three-bedroom fieldstone home could be transformed into a gallery, office, or retail space. Or a buyer could simply opt to live here and forgo the commercial opportunities. A period restoration has preserved all of the home’s original warmth with modern necessities like high-speed internet and plenty of parking.
New Hope, PA


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