From a Quirky Carriage House to a Second Empire Mansion, Another Look at 5 Historic Upstate Homes


    Whether your dream home is a quaint carriage house, a charm-filled cottage or a grand estate, there are plenty of drool-worthy houses in the region beyond Brooklyn to fantasize about.

    Featuring those properties has meant rummaging through historic accounts to separate truth from folklore, hunting through 19th century newspapers for amusing anecdotes about owners, and pinpointing properties on historic maps.

    Checking in on just a few of the properties we’ve featured in the past, there are tales of a 1920s businesswoman, a doctor at Sing Sing Prison, a filming location for a Milos Forman film and an architectural style easily identifiable from a classic piece of American art. Several of the properties are in Westchester, with the others in Dutchess and Columbia counties. When we first featured them they ranged in price from $389,000 to $12.5 million. How many of these are still on the market?

    upstate homes for sale

    Three Hudson Valley Board-and-Batten Cottages, Starting at $398K

    Board-and-batten cottages became popular in the mid 19th century for their “neat and picturesque” appearance and became an iconic country home style. If you’ve seen Grant Wood’s classic “American Gothic” painting then you’ve seen a board-and-batten house, even if you didn’t realize it. Just behind the pitchfork-holding gentleman is a stark white Gothic-style house with board-and-batten siding. We found three Hudson Valley cottages on the market that exemplified the style; the least expensive of those, the Parrish-Overocker House in Poughkeepsie Township, was listed at $389,000 when we wrote about it in October. According to the broker’s site, the house is still on the market and now listed at $355,000.

    518 harris road bedford hills

    A Mix of Old England and 20th Century American Style at Little Cassiobury in Bedford Hills

    What looks like a 20th century manse in Bedford Hills actually turns out to have ties to a grand English country house. It makes sense that the original owner was an antique dealer with an eye for opportunity when the contents and building materials of the demolished Cassiobury estate in Herfordshire went up for sale. Her purchases were incorporated into her new home, which she christened Little Cassiobury and used as a clever showplace for her business. On the market for $12.5 million when we wrote about it in September, the house and its surrounding 24 acres are still available.

    36 south highland avenue

    Become the Squire of this Eclectic 19th Century Concrete Manse in Ossining

    Built as a single family home in 1872, this concrete house in Ossining has had many monikers over the years with Highland Cottage, Squire House and Grandview Sanitarium, just a few examples. There’s lots of folklore associated with this unusual property, which meant reading through 19th century newspapers and the 20th century writings of a Sing Sing Prison doctor in an attempt to track down the truth. When we wrote about the property in August it was on the market for $965,0000 and it sold in November for $925,000.

    upstate homes for sale 705 cherry alley hudson

    A Quirky Carriage House in Hudson for $925K, Menagerie Not Included

    While Hudson is known for its prime examples of 19th century architectural styles, this downtown dwelling has a more unusual quirky charm. One of the many small service buildings that once lined the alleys of the town, this stone carriage house was converted to a warehouse in the 1950s. It’s now a live/work space that has been layered with vintage character on the interior, making for an intriguing possibility if you are looking for an alternative to the traditional domestic charmers of the town. It was on the market for $925,000 when we featured it in March of last year, and it is still on the market with a new price of $875,000.

    mount kisco

    Live the American Girl Dream in the Grand Second Empire Home of Doll Samantha Parkington

    This circa 1870s Second Empire mansion in Mount Kisco has amazing street appeal with its mansard roofs, tower, bay windows, a heavy bracketed cornice and iron cresting along the roofline. Its history is just as appealing and led to some investigation into the film “Ragtime” and the American Girl Doll Samantha Parkington. On the market for $1.6 million when we wrote about it last April, it sold in July for $1.5 million. Whether it was purchased by a film buff or American Girl Doll fan, we don’t know.

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