Oyster Bay Homes with Naples High School High school

Welcome to Oyster Bay, a hidden gem nestled in the heart of Naples, Florida. This charming neighborhood offers a unique blend of coastal living and suburban tranquility, making it an ideal place for families, retirees, and anyone looking to embrace the Florida lifestyle. With its picturesque waterways and lush landscapes, Oyster Bay is a haven for nature enthusiasts and outdoor adventurers alike.

One of the standout features of this delightful community is its proximity to Naples High School, which is renowned for its academic excellence and vibrant extracurricular programs. Families will appreciate the convenience of having a top-rated school just a stone's throw away, ensuring that education is always within reach. The school’s commitment to fostering a supportive and engaging learning environment makes it an excellent choice for your children’s educational journey.

Oyster Bay is characterized by its stunning homes, many of which boast waterfront views and lush tropical gardens. Whether you’re seeking a cozy single-family residence or a luxurious waterfront estate, this neighborhood offers a diverse range of properties to suit every taste and budget. The sense of community is palpable here, with friendly neighbors and a welcoming atmosphere that makes you feel right at home.

In addition to its beautiful homes and excellent schools, Oyster Bay is conveniently located near Naples' world-class dining, shopping, and recreational options. From pristine beaches to vibrant cultural attractions, residents have endless opportunities to explore and enjoy all that this incredible region has to offer. Experience the charm and warmth of Oyster Bay—where your dream home awaits!

Newest Oyster Bay Homes with Naples High School High school

$3,095,000

3 Beds ⋅ 3 Baths ⋅ 226034349 MLS

A rare waterfront offering in Oyster Bay, 1420 Jewel Box Avenue captures the best of Naples living. With 160 feet of water frontage across two sides of the property, two private docks, two boat lifts, and bridge-free access to Naples Bay and Gordon Pass, this is an exceptional setting for those who want to spend their days on the water. Southern exposure brings natural light into the home and sets the stage for sweeping water views, sunrises, and sunsets. Inside, updated interiors and open living spaces offer an inviting setting for entertaining or a quiet retreat after a day on the boat. Meticulously maintained, the home is equally suited to year-round living, a seasonal escape, or the opportunity to create a new waterfront residence. Just minutes from downtown Naples, acclaimed dining, shopping, and the Gulf beaches, this distinctive property pairs a coveted boating location with remarkable possibilities.

1420 Jewel Box AVE, Naples

$399,000

2 Beds ⋅ 2 Baths ⋅ 225071695 MLS ⋅ Chesapeake Landings BLDG.

RENOVATED WATERFRONT CONDO – DIRECT GULF ACCESS – TURNKEY FURNISHED! Nestled on a picturesque street lined with majestic banyan trees, this fully renovated two-bedroom, two-bath residence offers modern luxury in the heart of Naples. The open-concept layout showcases brand-new finishes throughout, including 42-inch cabinetry, sleek flooring, and stylish contemporary details that create a bright, coastal feel. An oversized screened lanai overlooks a wide, tranquil canal—perfect for relaxing while watching boats pass by—with direct, no-bridge access to Naples Bay and the Gulf of Mexico. Each unit includes its own private dock slip, with boat dockage permitted for vessels up to 22 feet, making this an ideal retreat for boating enthusiasts who want quick and convenient access to open water. The condo is being sold turnkey furnished for immediate enjoyment or rental use. Washer and dryer hookups are available, with the option for future installation. Just a short stroll to iconic 5th Avenue South, you'll be immersed in Naples' vibrant downtown lifestyle with world-class dining, shopping, galleries, and entertainment at your fingertips. This prime waterfront setting combines the charm of Old Naples with unmatched boating access, making it an exceptional opportunity for a seasonal getaway, investment property, or personal coastal retreat in one of the city's most sought-after locations. Currently 3 Rental Inquiries for Jan, Feb, March, 2027, from $6800 - $8000 per month **THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.**

1517 Chesapeake AVE Unit B3, Naples

Start Your Search

The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program (BR Program) of M.L.S. of Naples, Inc. Properties listed with brokerage firms other than this company are marked with the BR Program Icon or the BR House Icon and detailed information about them includes the name of the listing brokers. The properties displayed may not be all the properties available through the BR Program. The information provided is for consumers’ personal, non-commercial use and may not be used for any other purpose.