Homes With Spine-Tingling Histories: Intriguing Abodes Replete With Character That Are Ready for a Modern Makeover

Spooky season might reach its pinnacle on Halloween, but as the winter weather approaches and fog fills the air, an eerie atmosphere will no doubt continue to cloud the coming months.

Fall is a time for embracing history—telling stories around a fire, looking back on the events around Thanksgiving, and, for house hunters and homebuyers, exploring historic properties that boast their own truly intriguing tales.

While modern mansions and new-construction homes abound on the real estate market, for those eager to seek out a dwelling with more character, there are some truly special abodes to be found, all of which are replete with personality—both in terms of their architecture and their backstories.

Whether you are on the prowl for a "haunted" home or just intrigued with the stories behind a historic property, Halloween is the perfect day to check out some spine-tingling dwellings.

While not for the faint of heart, here are five chilling abodes from Massachusetts to Louisiana that will surely get in you in the All Hallows' Eve spirit.

1. 1000 Ocean Ave, Brooklyn, NY

Price: $2,595,000

Ditmas Park: As the pictures indicate, this six-bedroom antique is "in need of a comprehensive restoration" - both inside and out.

Built in 1899 for Wall Street magnate George Van Ness and his family, the "restoration masterpiece" set in the Historic Landmark District still boasts many period details. Highlights found throughout the 5,870-square-foot residence include Corinthian pilasters, Palladian windows, an original staircase, leaded-glass windows, several parlors, a library, billiard room, and four fireplaces. A detached carriage house is also in need of a revival.

According to the New York Post, the seller, who purchased the property for $1.25 million in 2021, was "overwhelmed" with the restrictions and costs involved with renovating a landmark property and decided to sell. Even more shocking than its current state of disrepair is the request for "cash buyers only."

Laura Rozos of Compass is the listing agent.

2. 138 Amenia Rd, Sharon, CT

Price: $7,500,000

Filston: This Gilded Age estate with Italianate, Palladian, Neo-Gothic, and French Empire influences was built for the heir to the Colgate toothpaste fortune.

Designed in 1903 by architect William Cromwell, Jr. for Romulus Colgate, the neoclassical "treasure" has been impeccably preserved over the years. The 12,057-square-foot interior boasts 19 spacious rooms, including 10 bedrooms, grand living and dining areas with ornate details, and eight fireplaces.

Located on 105.94 mysterious acres, the enormous property on three parcels is surrounded by equestrian trails and "rolling hills." There is also a three-story carriage house located on a dedicated parcel.

Dan Kessler of Compass Westport is the listing agent.

3. 8 Old Conn Path, Framingham, MA 

Price: $750,000

Thomas Hasting Home: This historic home with "timeless soul" and "welcoming spirit" has been thoughtfully modernized over the years.

Built in 1750, the 2,238-square-foot residence still boasts wide-plank floors, custom millwork, exposed beams, built-ins, two staircases, and four fireplaces, including one in the kitchen with beehive oven. Four bedrooms can be found upstairs. A spacious back deck overlooks the fenced-in yard with swing set (included with the sale).

The property also has an oversized one-car garage with extra storage space.

Diane B. Sullivan of Coldwell Banker Realty - Framingham is the listing agent.

4. 2 Bedons Aly, Charleston, SC

Price: $5,950,000

Humphrey Sommers House: This charming 18th century residence originally hit the market in April for $6,450,000 and recently received another $200,000 price chop.

The four-bedroom residence with guest suite built in 1778 is located just steps away from the waterfront yet flood insurance is not required, according to the listing. The alley is said to have suffered severe damage from fires in 1740 and 1778, but this property survived.

Historic highlights found throughout the 5,197-square-foot interior include exposed brick walls, preserved hardwood floors, built-in cabinetry, and several fireplaces with ornate mantels. Designed for entertaining, the modernized kitchen now features double wall ovens, high-end appliances, and a spacious island with farmhouse sink.

A brick-walled courtyard can be found in the private backyard surrounded by magnolia and lemon trees. There are also two separate one-car garages.

Ruthie Ravenel of Daniel Ravenel Sotheby's International Realty is the listing agent.

5. 2003 Dumaine St, New Orleans, LA

Price: $350,000

Maison Vitry: This three-bedroom residence featured in American Horror Story recently sustained fire damage and is seeking a real estate revival.

Built in 1855 for Free Woman of Color Louise Arsene Vitry, the historic 3,349-square-foot home is looking for a buyer to restore its original glory. Original plaster, a mahogany staircase, hardwood floors, custom millwork, ceilings, and damaged walls are all in need of attention. Some rooms were completely destroyed by the fire while others seem to require a facelift.

A screened-in porch overlooks the fenced-in backyard.

Steve Richards of Wurth Real Estate Services is the listing agent.