Share this article


Your message has been sent.

    Send Email

    North of NYC North of NYC By Houlihan Lawrence By Houlihan Lawrence by

    America celebrates its 242nd birthday this year, and while stories of our founding fathers seem distant memories most relatable as Broadway musicals, that's considerably young on a global scale. Our affiliates across the globe at Luxury Portfolio International routinely list properties twice that, like this Belgian manor from 1571 or a 12th century Umbrian castle whose buyer inherits a Lord title.

    Nevertheless, our communities play host to a handful of homes older than the country itself, still doing the job they were built for. Here are just a few currently listed with us, waiting for you to write their next chapter:

    GREENWICH | 15 Old Mill Road | c. 1715
    On nearly four mid-country acres, the Joshua Reynolds House isn't just our oldest current listing, but carries the provenance of being built by one of Greenwich's founding families. Jonathan Reynolds arrived in 1656, and his purchase of six acres was the first deed ever recorded in the town's register. Another Reynolds led a committee that booted a local preacher for "dullness." Joshua Reynolds acquired his land from members of the Mead family (well-known for settling Waccabuc, New York), and the home went back and forth between Mead and Reynolds ownership for nearly 200 years.

    In the mid-20th century, it was moved back from the road, allowing the landmark to evolve into a thoroughbred luxury estate. More than 9,000 SF of interior, replete with a walkout lower level boasting a wine cellar and game room, are accented with original flooring, fireplaces and chestnut beams. A former stable has been converted into a guest suite, and the pool are is immersed in lush plantings. The home is among the last intact examples of a New England Center Chimney-style home in Greenwich, and among the finest anywhere.

    See more of 15 Old Mill Road

    DARIEN 40 Swifts Lane | c.1719
    Built in Southbury, CT, more than a half-century before the Second Continental Congress convened, this magnificent survivor classic spent 200 years at its original location until an owner simply wanted to be closer to New York City. Less-inclined to leave their beloved home behind, they moved it to its present 2.4-acre site on the Gold Coast of Fairfield County, packing its more delicate components in bales of hay. Recently given a 21st century remodel, the home is a sight to behold in its own right, but the setting is equally incredible: The property enjoys more than 500 feet of frontage on Gorham's Pond, which sits atop a quiet cove off Long Island Sound.

    See more of 40 Swifts Lane

    YORKTOWN HEIGHTS | 1250 Baptist Church Road | c.1741
    Set about halfway between Connecticut and the Hudson River, Yorktown has always been a convenient place to settle. While much of the area has developed into suburbia, this loving restored 18th century jewel retains the feel of how everything up here used to be. Set amidst four acres on a quiet country road, the home's spec sheet reads like a litany of swoon-worthy architectural detail. Exposed brick nogs flank the kitchen, which is brightly color-splashed and centered around a robust fireplace. A red barn and garden patio complete the package.

    See more of 1250 Baptist Church Road

    HARTSDALE 109 Ridge Road | c. 1760
    We like to think Westchester has always been revolutionary, and you could say it started in the war for our independence. An early skirmish with redcoats was waged along the Bronx River right behind what's now the Hartsdale train station. This authentic Saltbox sits just down the street from Odell House, where General Rochambeau once made his headquarters, and has been thoughtfully restored for today's living without compromise to its period integrity. Artful textures and color splashes interplay plank floors, period hearths and hand-hewn beams. The home sits immersed in blossoming gardens on a spacious half-acre, and across the street is Hart's Brook Preserve, aplenty with winding wooded trails to explore. With Metro North's Harlem Line close by, the commute to Manhattan isn't bad, either.

    See more of 109 Ridge Road

    SOUTH SALEM | 240 Kitchawan Road | c.1763
    Clarence Bouton is a neighbor most would remember by a street sign bearing his family name, but the early homesteader's house is still standing, a pristine example of Colonial-era design. The home sits on a well-appointed acre shared with an 1870s barn and outbuilding, perfect for use as a studio, workshop or guest house. There's even an automatic generator.

    See more of 240 Kitchawan Road

    CHAPPAQUA | 275 Bedford Road | c.1775
    Completed the year before John Hancock signed the scroll, this gambrel-roofed beauty is regarded as one of Chappaqua's finest estates. The spacious main residence showcases nearly 10,000 SF of sophisticated interior that speak to today's sensibilities, from formal entertaining rooms to a designer kitchen that opens to a sun-splashed atrium breakfast area. 7+ acres of grounds feature a pool and pool house, tennis court and putting green, and it might be the oldest home we've ever seen with an indoor basketball court.

    See more of 275 Bedford Road

    Explore All Listings