A time of sustained economic growth and prosperity, it’s no wonder that “The Roaring ‘20s” saw a wealth of magnificently built homes. From charming Tudors to classic Colonials, residences built in the 1920s exude a genuine sense of character that is not to be missed. Here are three outstanding homes, all built with the strong foundation of their shared era, that have been meticulously renovated to meet the demands of today, while staying true to the exquisite qualities of their time.

It’s called Fairfield County’s “Best Kept Secret” for a reason! 17 Shagbark Road, located in the private waterfront community of Wilson Point in Norwalk, CT, is a truly magnificent home. Wilson Point is a peninsula of about 150 coastal acres, bordered on the east by the Long Island Sound and on the west by Wilson Cove. There are over 80 houses in the area ranging in age and size from an original farmhouse built in 1749 to recently constructed, larger properties. The neighborhood is also home to The Norwalk Yacht Club.


The 1920s Tudor, which is listed with Darien agent Bruce Baker at $1,989,000, has since been updated, making sure to stay true to its historic integrity. One aspect of this home that is especially interesting is its great room, which was once an artist’s studio. The room maintains various original features including 22-foot, vaulted ceilings, wide-planked wood floors, a large fieldstone fireplace and French doors that lead out to a back stone patio. A large loft additionally overlooks this spacious room, which is rumored to have once housed an organ used to entertain the artist’s guests as they viewed his work. Other highlights include an up-to-date chef’s kitchen, large sun-filled windows with spectacular vistas, an elevated deck and more. In total, the home includes five bedrooms and four baths.


Over in Westchester County, yet another updated 1920s home resides on 1.38 acres of park-like grounds in the exclusive Hillandale neighborhood of Rye Brook, N.Y., a community situated in the heart of the town. Represented by Rye agent Melissa Kaminsky for $2,075,000, the classic Colonial residence, which was completely renovated in 2008, epitomizes fine suburban living. Whether one is looking for ample space, top-notch amenities or a prime location, 14 Beechwood Boulevard has it all. Numerous features grace the interior of this freshly expanded, six-bedroom, five and a half-bath home, including stunning hardwood floors, an updated, state-of-the-art eat-in kitchen, three fireplaces and vaulted ceilings. There is also an oversized family room, bonus room and an expansive deck, providing ideal opportunities for home entertainment.

14 Beechwood-214 Beechwood

6 Overdale Road, located in the highly sought after coastal community of Greenhaven in Rye, N.Y., boasts traditional 1920s Tudor details, combined with a renovated contemporary interior. Listed with Rye agent Fiona Dogan at $2,775,000, the enchanting 1929 home contains a two-story addition, which includes a new, oversized walk-in master closet, second floor balcony and an in-home office. While numerous original details such as its beamed ceilings, diamond-pane windows, slate roof with a beautiful gabled roofline and interior moldings do remain, the residence also offers the convenience of an open floor plan with a kitchen and family room combination that caters to modern demand. Needless to say, there is no doubt that this Westchester County gem feels brand new and is in pristine move in-ready condition. Existing furniture is also available with the sale of the home, and is to be purchased separately.


For more information on 17 Shagbark Road, please visit our website here. You can also contact Darien agent Bruce Baker by phone at 203.912.7061, or by email at Details on 14 Beechwood Boulevard can be found here. You can also reach out to Rye agent Melissa Kaminsky by phone at 917.748.8880, or by email at Please click here for additional information on 6 Overdale Road, or contact Rye agent Fiona Dogan by phone at 914.414.5147, or by email at

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