Orchard Smith Homestead From 1678 Is the Week’s Oldest Listing

If you’re yearning for a bucolic country retreat surrounded by natural beauty, we have just the tonic. Join us on a journey back through the centuries to a simpler time.

This list of the oldest properties to hit the market this week is filled with showstoppers.

For example, take the Orchard Smith Homestead. The oldest of this week’s crop dates all the way to 1678, nearly a century before the United States was formed. Located about 30 miles west of Boston, this historic retreat in Massachusetts offers plenty of nods to the home’s past glory.

Besides that rare dwelling from the 17th century, there’s also a multimillion-dollar working horse farm, a 3-acre estate overlooking the Connecticut River so beautiful it has attracted generations of landscape painters, and a downtown Charleston townhome full of Southern charm.

You also don’t want to miss a Pennsylvania property thought to have served as a stop on the Underground Railroad.

So take a moment and check out these 10 vintage escapes, for a true breath of fresh air.

1. 174 Great Rd, Maynard, MA

Price: $599,000
Year built: 1678
Orchard Smith Homestead: Described as “perfect for a history buff,” this property has been under the care of the same owner for the past 45 years.

The four-bedroom Federal farmhouse boasts wide-pine flooring, five working fireplaces, exposed wood beams, and other period details. Outside, the grounds feature an illuminated waterfall, patio, and privacy. Amenities from this century include a lower-level game room and wine cellar.

Maynard, MA



2. 255 Davis Rd, Bedford, MA

Price: $3,900,000
Year built: 1705
Turnkey farm: A thoroughly modern horse farm has been built around it, but this property’s farmhouse dates to 1705, and has been featured in Country Living magazine.

The rest of the 7-acre spread includes an owner’s barn, an indoor riding area, stalls for 25 horses, an outdoor riding ring, and two caretaker residences.

Bedford, MA



3. 39 Main St, Port Republic, NJ

Price: $379,900
Year built: 1710
Historic Colonial: Sitting on just over an acre, this four-bedroom home features original hardwood floors, handmade cabinets, and a rear addition that includes a roomy family room and office.

Soak up the fresh air outside on the wraparound porch. Nearby Mill Pond beckons, and gear for aquatic pursuits can easily be stored in the shed.

Port Republic, NJ



4. 59 Neck Rd, Old Lyme, CT

Price: $1,350,000
Year built: 1716
Artist overlook: Situated on over 3 acres overlooking the Connecticut River, this site is so beautiful that it has been a go-to spot for landscape painters. One of those artists was Allen Butler Talcott, who bought the place in 1904. He remodeled it and added a painting studio.

Today, the compound includes the 4,700-square-foot farmhouse, a two-room in-home office with a separate entrance, and a second-floor apartment. There’s also a two-car garage with an attic, a garden shed, barn, and access to kayak and canoe storage on the river.

Old Lyme, CT



5. 558 S. Canterbury Rd., Canterbury, CT

Price: $549,900
Year built: 1718
Country Colonial: Stone walls and a circular drive welcome guests to this 14-acre property, with its three-bedroom Colonial home.

The vintage residence boasts original wide-board floors, a library with a fireplace, a formal living room with another fireplace, built-ins throughout, and a walk-up attic. For additional income, the detached two-car garage has a full apartment above it.

Canterbury, CT



6. 131 Mitchell Hill Rd, Lyme, CT

Price: $895,000
Year built: 1723
Whitehall estate: Built on 4 wooded acres, this country estate features stone walls, an in-ground pool, a post-and-beam building with a workshop and a studio, plus a three-car garage with a room above.

The four-bedroom main house has a lower-level “Tavern Room,” with an oversized fireplace and beamed ceilings with walkout access.

Lyme, CT



7. 204 Limekiln Rd, New Cumberland, PA 

Price: $380,000
Year built: 1734
Ashton-Hursh House: This limestone home is listed on the National Register of Historic Places and is believed to have been part of the Underground Railroad.

The original structure now serves as a guesthouse and is believed to be the oldest occupied structure in York County. The 2.5-acre lot also includes the more modern seven-bedroom main house, with views of Yellow Breeches Creek.

New Cumberland, PA



8. 61 1/2 Tradd St, Charleston, SC

Price: $1,295,000
Year built: 1736
Downtown charmer: This townhome sits in the middle of downtown Charleston, with original heart-of-pine floors and fireplaces.

With its three stories, the three-bedroom residence offers city views, plus an updated kitchen and bathrooms. Outside, there’s a private courtyard with a garden and fountain.

Charleston, SC



9. 2545 Kingstown Rd, South Kingstown, RI

Price: $615,000
Year built: 1736
Elisha Reynolds house: Minutes from beaches and the University of Rhode Island, this half-acre property features a five-bedroom, center-hall Colonial. Lovingly restored, the 3,400-square-foot home is large enough to be used as a bed-and-breakfast or as a large family residence.

South Kingstown, RI



10. 204 Rowayton Ave, Norwalk, CT

Price: $1,099,000
Year built: 1740
Captain’s home: This antique three-bedroom home sits on a parklike quarter-acre and has been updated throughout. There’s also a newer attached barn with a loft for entertaining. Enjoy the gorgeous grounds on one of the property’s two outdoor patios.

Norwalk, CT


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