Built in 1690, a Colonial on a Famous Road Is the Week’s Oldest Home

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Situated on Boston Post Road—the first mail delivery route between Boston and New York City—this week’s oldest home on Realtor.com® dates to 1690. Built nearly 90 years before the start of the Revolutionary War, this Connecticut Colonial still possesses many of its antique charms. With a price well below the national median, it’s also affordable.

It occupies a prime slice of commuter access to major city centers, and includes a barn. It also offers the opportunity to reimagine the rural retreat as either a retail or a residential space, depending on what the buyer has in mind.

Other vintage highlights this week included a home used as an antique shop in Pennsylvania and a beautiful brick house in New Jersey with reported ties to the nation’s first president, George Washington.

In the top 10, you’ll find a choice of ranches, renovation projects, and even mixed-use possibilities to ring in the new year. Scroll down and have a look.

1. 427 Boston Post Rd, East Lyme, CT

Price: $325,000
Year built: 1690
Restorationist wanted: Loaded with history and potential, this four-bedroom, 2,445-square-foot Colonial sits on just under 5 acres on the historic Boston Post Road.

A slice of the country life, the antique residence comes with a barn and ample potential for transformation into a modern gem. Zoned for everything from residential to commercial and agricultural use, the property is surrounded by family farms and orchards.

2. 298 Boston Rd, Palmer, MA

Price: $189,900
Year built: 1740
Unregistered historic: Available for less than $200,000, this 14.6-acre property is being sold as is and ready for improvements.

The four-bedroom, 2,354-square-foot farmhouse still has some original woodwork and sits in the middle of a wooded area that was once used as farmland. Plenty of work awaits a buyer: there’s a failed septic system, a detached barn without a roof, and unlined chimneys.

3. 351 Wiese Albert Rd, Haddam, CT

Price: $275,000
Year built: 1743
Antique Cape: The first floor of this two-bedroom,1,511-square-foot home has been fully remodeled. Updates include a modern kitchen and a bright-red front door.

The second floor awaits completion by new owners. Upstairs, the bedrooms and bathroom are filled with unique spaces ready to be reimagined.

4. 6230 Lower York Rd, New Hope, PA

Price: $575,000
Year built: 1750
Jones Antiques: The antique shop sign out front indicates this 1.23-acre property’s residential and commercial potential. It’s being sold as is, and there are no signs of any antiques beyond the buildings themselves.

A buyer will acquire a three-bedroom fieldstone bank house that includes two stone fireplaces and pumpkin-pine, random-width floors. There’s also a 1,150-square-foot barn with a heated and air-conditioned workshop.

5. 108 Maple Ave, Chestertown, MD

Price: $329,000
Year built: 1782
Bolton-Anderson House: Just a block from the Chester River, this two-story fixer-upper is being sold as is, with many of its original features and fixtures. It’s a historic project for a preservation-minded buyer.

The five-bedroom, 2,460-square-foot home sits on a little less than a half-acre, and a renovation is already underway. The listing notes that about half the walls are open and ready for new electrical wiring.

6. 208 S. Loudoun St, Winchester, VA

Price: $650,000
Year built: 1783
Downtown historic: Opportunity knocks on this old front door. This six-bedroom, 5,514-square-foot property could be used for commercial or residential use, or for some combination of the two.

It comes with a backyard, five off-street parking spots, and a two-car garage with a workshop. It’s located right on the Downtown Walking Mall, and its interior highlights include original hardwood floors and woodwork, as well as a handsome banister that links all three stories.

7. 206B Pinnacle Rd, Lyndeborough, NH

Price: $750,000
Year built: 1784
Refreshed ranch: This 20-acre ranch comes with two updated homes.

The first is a farmhouse from 1784 with an enticing secret closet beneath the stairs. The second home on the property has been totally remodeled, and includes a new dream kitchen and walls of windows.

Surrounding acreage includes ponds and plenty of room for hiking and skiing.

8. 414 Grove Ave, Petersburg, VA

Price: $244,000
Year built: 1785
Mary Mann House: The home is zoned for mixed use and sits close to shopping, dining, and the Appomattox River.

Inside, this three-bedroom home features four fireplaces, 12-foot ceilings, and an extra room downstairs with its own door, for use as an office or studio.

Updates include a new rear deck, fresh bathrooms, and a new security system.

9. 330 Cohansey Friesburg Rd, Bridgeton, NJ

Price: $389,000
Year built: 1790
Col. Jacob Hitchner House: The listing says this stately home has direct ties to George Washington. Over the centuries, it’s served as a tavern, stagecoach stop, town center, farm, and family home.

Today, the five-bedroom, 4,450-square-foot home sits on 2 acres and includes wide pine floors, exposed beams, period hardware, wood paneling, chair rails, and five fireplaces. Outside, there’s a brick patio with a pergola and mature landscaping.

10. 185 Lonetown Rd, Redding, CT

Price: $775,000
Year built: 1790
Country Colonial: This home belongs to an interior designer, a fact that comes across clearly in the gorgeous listing photos.

You’ll see a new kitchen with top-of-the-line appliances, lovely chestnut floors, vaulted ceilings, and delightful decor throughout. The private, 3.21-acre lot also includes a detached garage.

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