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Vintage Charm: The 10 Oldest Homes To Land on the Market This Week

Dating to 1700, the oldest home to hit the market this week was built a mere 80 years after the Pilgrims landed on Plymouth Rock.

It sits atop our list of the 10 oldest homes that went up for sale in the past seven days. All built in the 1700s, they’ve weathered the centuries and still stand in fine fettle today.

Now these vintage charmers are ready for a new owner to write the next chapter in their long histories. One of these properties comes with the lovely name of Tree Farm, and is filled with wildflowers to attract butterflies and birds. And then there’s Fleetwood, which comes with its own ancient cemetery. This week’s oldest homes also include a 68-acre gentleman’s farm, filled with pastures, ponds, and an herb garden and a family compound with a home dating to 1710.

Even at the 300 year mark, these properties are just getting started! Scroll down for a trip through history and a hopeful look at the memories still to be made in these remarkable residences.

Price: $269,000
Built in 1700: At the ripe, old age of 320, this three-bedroom, 1,150-square-foot Mainer is still in its prime—and it’s affordable! Perched on the east side of Boothbay Harbor, the home’s been owned by the same family for the past 50 years. It includes bay windows, built-ins, a large front porch, and a lovely backyard.

Boothbay Harbor, ME
Boothbay Harbor, ME

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Price: $579,900
Built in 1707: Consisting of 68 acres, this gentleman’s farm includes a remodeled four-bedroom farmhouse with nearly 3,000 square feet of living space. The living room features a three-story stone fireplace along with custom built-ins throughout. The main house is a short stroll to the farm’s two barns and caretaker’s quarters. The acreage includes a pond, pastures, forestland, and an herb garden.

Haddam, CT
Haddam, CT

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Price: $3,750,000
Built in 1710: This property was given a dramatic overhaul in 1989 to build a multigenerational family compound on over 10 acres. Now serving as a 1,700-square-foot guesthouse, the original farmhouse dates to 1710. The compound consists of five buildings, and the main house includes a grand living room inspired by a Yale dining hall. There’s also a caretaker’s cottage, carriage house apartment, studio, and pool house.

Lyme, CT
Lyme, CT

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Price: $724,900
Built in 1712: Tucked back on historic High Street, this restored four-bedroom home features wide-plank pine floors, beamed ceilings, and a restored central chimney for five fireplaces. According to a plaque on the grounds, the original 9-acre lot was the home of Thomas Dudley, the governor of Massachusetts Bay from 1635 to 1659. Today, the property’s large lot is filled with beautiful gardens, walking paths, and mature trees.

Ipswich, MA
Ipswich, MA

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Price: $469,900
Built in 1720: The original saltbox house was constructed in 1720, and the Federal-style house in front was added in 1840. Today, the three-bedroom home bursts with charm and key updates. There’s a new gas furnace, circular driveway with cobblestone apron, remodeled kitchen, and new concrete flooring in the basement. The property sits across from Bauer Park, a 64-acre open space with ponds, hiking trails, and community gardens.

Madison, CT
Madison, CT

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Price: $249,900
Built in 1720: Previously known as Babcock Tavern, this 3,000-square-foot home sits on a lush green acre. It was also a popular bed-and-breakfast, ranking among the top 50 in the country. Today, the five-bedroom home comes with a tavern room, and the seller is willing to include a few antiques in the purchase price.

Tolland, CT
Tolland, CT

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Price: $229,900
Built in 1727: Sitting on a full acre, this charming Cape Cod has two bedrooms and 1,200 square feet of living space. From its lemon meringue exterior to the three-season enclosed porch and huge backyard, this petite home leaves a big impression.

Windham, CT
Windham, CT

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Price: $425,000
Built in 1730: Lovingly cared for, this is one of the oldest homes in Culpeper County. The 10-acre property includes a cemetery. Known as Fleetwood, the property includes a four-bedroom main house, a stable, board-fenced pasture for horses, kennels, workshop, and garden shed. There’s also a sycamore tree believed to be hundreds of years old.

Jeffersonton, VA
Jeffersonton, VA

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Price: $400,000
Built in 1730: This three-bedroom Colonial sits on more than 2 acres. It comes with a 2,000-square-foot, Amish-built barn as well as attached sheds. The main house features five fireplaces and a children’s play area. It’s all just minutes from beaches and hiking trails.

Middleboro, MA
Middleboro, MA

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Price: $379,900
Built in 1736: Tree Farm is a spectacular property with natural beauty, including a bird and butterfly sanctuary, streams, and botanical gardens. The two-bedroom home features wide-plank flooring, a remodeled bathroom, and an in-ground pool. The current owner is an interior and architectural designer who spent the past 30 years taking impeccable care of this one-of-a-kind residence.

Plymouth, CT
Plymouth, CT

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