Oakland Beach Avenue – Rye, NY
Stretching from the heart of Rye down toward the Long Island Sound, Oakland Beach Avenue is more than just a street—it’s a gateway to some of the city’s most scenic, convenient, and community-driven living. Whether you’re commuting, heading to the beach, or taking a casual walk to town, Oakland Beach Avenue connects you to everything that makes Rye such a sought-after place to live.
A Street That Has It All
Oakland Beach Avenue begins near Boston Post Road and runs southeast all the way to Playland Parkway, where it curves around to Rye Town Park, Playland Beach, and Milton Harbor. Along the way, it passes tree-lined residential areas, beautiful homes, recreational spaces, and even some historic churches and civic buildings.
The diversity of the street is part of its charm—offering a mix of single-family homes, classic Colonials, Tudors, and more recently updated properties, all reflecting the charm and elegance Rye is known for.
Close to Nature, Parks, and the Sound
One of the defining features of Oakland Beach Avenue is its proximity to Rye’s coastal beauty. From anywhere on the street, you’re only minutes from:
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Rye Town Park and Beach – ideal for sunny afternoons, evening walks, and dog-friendly outings.
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Playland Park – a historic amusement park and boardwalk offering fun for all ages.
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Milton Harbor – a peaceful spot to kayak, paddleboard, or just admire the view.
Living here means you can have a beach day any day—or enjoy the calm of harbor breezes in the evening.
Community & Convenience
Oakland Beach Avenue is also close to Milton Elementary School, making it a popular choice for families. It's walkable or bikeable to downtown Rye, where you’ll find charming shops, cafes, the library, and the Metro-North train to NYC.
Despite being one of Rye’s more traveled streets, it maintains a quiet, residential vibe—especially in the stretch between Milton Road and the shoreline. Neighbors tend to know each other, and the homes are often beautifully maintained with pride of ownership on full display.
A Perfect Blend
What makes Oakland Beach Avenue special is its balance of energy and tranquility. It's central, scenic, and social—yet still offers plenty of peace and privacy for those who live along it. Whether you’re looking for coastal access, neighborhood feel, or everyday convenience, this street checks all the boxes.
Oakland Beach Avenue is a true Rye treasure—a scenic corridor that offers classic charm, beach-town energy, and suburban comfort all in one. For those looking to enjoy the best of Rye’s lifestyle, it’s a street worth watching—and living on.