319 Oakland Beach Avenue

Experience the best of Rye living in this beautifully updated four-bedroom Tudor, where timeless architectural character meets modern comfort just moments from the Long Island Sound, Rye Beach, downtown Rye and the train to NYC. Bright, spacious and filled with charm, the home offers an exceptionally flexible floor plan ideal for both everyday living and entertaining. The main level features hardwood floors, elegant arched entryways and a gracious living room anchored by a striking stone wood-burning fireplace and original ceiling beams. A sun-filled family room with oversized windows provides a wonderful place to relax, while the formal dining room is perfect for gatherings and special occasions. The fully updated kitchen features quartz countertops, modern appliances and direct access to the outdoor patio, creating an effortless indoor-outdoor flow. Two well-proportioned bedrooms are conveniently located on the main level along with a beautifully renovated full bathroom and laundry. Upstairs, two additional bedrooms offer privacy and flexibility, complemented by a newly designed marble bathroom and a generous cedar walk-in closet. The walk-out lower level adds even more usable living and entertaining space and includes one of the home's most unique features—an original 1920s speakeasy bar with its own separate entrance. Whether used as a recreation room, lounge, media room or entertaining space, it adds remarkable character and versatility. A second oversized laundry area is also located on this level. Outside, enjoy a private fenced-in yard, patio, detached one-car garage and a large driveway with additional parking. An EV charging station is available. The home has also been thoughtfully updated with central air conditioning, gas heat, newer windows and roof. Located in the highly sought-after Rye City School District and moments from Milton Elementary School, this exceptional home offers convenient access to Rye Town Park and Beach, the marina, boardwalk, parks, golf, pool, YMCA, shops, restaurants and Metro-North. Available furnished or unfurnished, for short- or long-term rental, with pets welcome. Offering space, style, flexibility and an unbeatable coastal Rye location, this is an exceptional rental opportunity designed to feel like home from the moment you arrive.