Built in 1700, an Affordable Connecticut Classic Is The Week’s Oldest Home

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Located in northwest Connecticut, the oldest home to hit the market on Realtor.com® is priced well below the national median and was around during the Revolutionary War. For a buyer in search of a history on a budget, just make your way to the Nutmeg State!

This vintage dwelling is located in the town of Winchester, which is known the “Gateway to the Berkshire Mountains.” The quaint area is known for its period architecture and also boasts one of the state’s largest lakes.

Other highlights from the 18th century this week include a Pennsylvania stone home that is now surrounded by an events business, an updated beauty on the Connecticut River, and a Colonial-Federal style farmhouse in the town of Roxbury, CT.

For more antique home dreams, have a look at all 10 of this week’s oldest homes.

1. 205 Torringford St, Winchester, CT

Price: $349,900
Year built: 1700
Revolutionary War history: This antique Colonial in northwest Connecticut survived the Revolutionary War and has centuries of tales to go along with it.

There are four fireplaces in this spacious home, which has historical charm everywhere—from the built-ins to the high ceilings. Updates over the years include an eat-in kitchen with a gas stove, a primary suite with a whirlpool tub, and updated windows.

2. 50 Weaver Rd, Denver, PA

Price: $3,250,000
Year built: 1739
Bear Mill Estate: A stone Colonial from 1739 is only one part of this compound, designed for big parties. In East Cocalico Township, the parcel also comes with a two-story events facility, currently being used to host weddings for up to 150 guests, as well as a flower shop and a separate home for the owners.

This Colonial’s classic history is preserved in its formal walkways, covered porches, slate roof, beamed ceilings, and its stone fireplace. Modern appointments in the main residence include an updated kitchen with stainless-steel appliances and granite countertops, walk-in showers, and a soaking tub.

The event space—formerly the first gristmill in Lancaster County—has a two-story glass elevator.

3. 61 Nottingham Rd, Deerfield, NH

Price: $495,000
Year built: 1750
Antique charm: This classic wood-frame structure with clapboard cladding was renovated in 2015, and now features a custom kitchen with quartz countertops.

Charming elements of this Colonial’s history can be seen in the exposed post-and-beam ceilings, built-ins, natural woodwork, wide pine floors, and corner cabinetry. The primary bedroom is located on the first floor and features radiant flooring, while the second and third floors offer three more bedrooms and a full bathroom.

4. 10 Allison Ln, Thornwood, NY

Price: $1,450,000
Year built: 1750
Old World charm: This classic Colonial combines Old World charm with modern amenities like a custom chef’s kitchen, whole house generator, marble en suite primary bath, and a detached garage with loft.

Well-preserved original details include wide-plank hardwood flooring, four fireplaces, traditional millwork, and hand-notched, beamed ceilings.

All the bedrooms are located on the second floor, and the spacious primary suite has a separate dressing area and office, while the third floor features a great room with a wet bar.

5. 2 South St, Cromwell, CT

Price: $345,000
Year built: 1760
Riverfront location: At this delightful home, which has been carefully maintained throughout the centuries, the bathrooms have been updated, a new roof was installed last year, and a ductless central air system has been added.

In the historic district of North Cromwell, this waterfront Colonial is just steps from the Connecticut River, with views that can be enjoyed from the enclosed porch.

Its historic charm can still be found in the exposed beams, hardwood floors, and five fireplaces. A modern kitchen has been updated to include a double-oven, stainless-steel range, granite countertops, a farm sink, and modern cabinetry.

6. 679 South St, Southbridge, MA

Price: $200,000
Year built: 1772
Westville Recreation Area: This historic four-bedroom farmhouse was relocated several years ago from the Westville Recreation Area to a private hillside lot across the street.

Its proximity to the Recreation Area means easy access to hiking, fishing, and boating. Heating and electrical systems have been updated, but the budget-friendly structure needs a new owner to transform it into a home.

7. 1501 Monk Rd, Gladwyne, PA

Price: $1,275,000
Year built: 1780
Ideal location: With a coveted Monk Road address, this 18th-century stone farmhouse is complemented by a modern addition.

There are two fireplaces, a covered balcony, and original pine floors in this four-bedroom home. Inside are a mix of Old World details and modern updates.

Highlights include a lovely kitchen with a side-by-side Sub-Zero refrigerator and a primary suite with a covered balcony and separate dressing area. If a buyer wants to create a compound, the adjacent lot is also available.

8. 65 Meeting St, Charleston, SC

Price: $3,565,000
Year built: 1789
South of Broad home: This classically elegant, five-bedroom house features luxe amenities like a built-in refrigerator, six-burner Thermador gas stove, and a primary suite with a marble bathroom.

A covered outdoor porch just off the kitchen lends itself to hosting a big party, and a den space at the back of the house has a bar. For comfort, central HVAC units and ductwork were installed recently on the second and third floors. A spectacular primary suite has a private screened-in porch and a spacious, dual walk-in closet.

9. 149 Main St, Essex, CT

Price: $379,900
Year built: 1790
John Clark Homestead: This notable home is listed in the “Houses of Essex, Vol. II,” for its ties to the piano-making Comstock family.

A separate cabin on the property with private access could be used to accommodate visiting family and friends or alternatively, rented out for additional income.

The main house has been updated with softwood flooring, new paint, and stainless-steel appliances in the kitchen. For even more space, it has a two-story heated barn in the private backyard.

10. 88 Old Roxbury Rd, Roxbury, CT

Price: $2,785,000
Year built: 1790
Colonial-Federal style farmhouse: This four-bedroom home sits on nearly 24 acres and features a 19th-century former smokehouse, an English, U-shaped barn, and a stream that runs through it.

Abutting Roxbury Land Trust, the residence, only 90 miles from New York City, is close to nature trails and preserves. Its period details include exposed beams, four fireplaces, and original hardwood flooring.

Modern amenities are evident in the country kitchen, with a butler’s pantry and a formal dining room with a cathedral ceiling.

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