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

$439,900

2 Beds ⋅ 2 Baths ⋅ 226023946 MLS ⋅ Chesapeake Landings BLDG.

Beautiful Waterfront condo completely remodeled and ideally situated on the Bay, offering Gulf access with no bridges. This stunning 2/2-unit features high-end appliances, an in-unit washer and dryer, hurricane impact windows and doors, and breathtaking water views. Located just 5 minutes from downtown 5th Avenue, you'll enjoy world-class dining, shopping, entertainment, and Naples white sand beaches. An exceptional opportunity to experience the ultimate Southwest Florida waterfront lifestyle.

1537 Chesapeake AVE Unit A-4, Naples

$3,395,000

3 Beds ⋅ 3 Baths ⋅ 226018001 MLS

Discover an exceptional waterfront retreat in the highly desirable location of Oyster Bay. This unique property offers a total of 160 feet of water frontage, 80 ft on the southern side and 80 feet on the northern side with two private boat docks, two lifts and bridge free access to Naples Bay and Gordon Pass- ideal for avid boaters and adventure seekers. This coastal charmer offers a perfect blend of timeless style, updated interior and open living spaces perfect for entertaining. Stunning water views and endless sunrises and sunsets with preferred southern exposure. This home has been meticulously maintained throughout the years making it an ideal full time/part time residence or an incredible opportunity for redevelopment. Enjoy close proximity to Downtown Naples, world class dining, shopping and beaches.

1420 Jewel Box AVE, Naples

$399,900

2 Beds ⋅ 2 Baths ⋅ 226012606 MLS ⋅ Clam Court BLDG.

Experience boutique waterfront living in this rare 6-unit condo association, perfectly situated in the heart of Naples. Just minutes from the world-famous 5th Avenue shops and dining—and a short stroll to Naples’ white sandy beaches—this residence blends charm, convenience, and coastal lifestyle. Enjoy tranquil canal views and direct Gulf access with no bridges—a true boater’s paradise. Inside, the light-filled layout is designed for comfort and ease, offering the perfect retreat after a day on the water or exploring downtown . With a rental policy allowing 12 rentals per year, this property is also an ideal opportunity for investors or AirBnB hosts , offering both personal enjoyment and strong income potential

1195 Clam CT Unit 202, 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

$7,777,000

5 Beds ⋅ 6.5 Baths ⋅ 225065690 MLS

Winner of the 2025 Sand Dollar award for Product Design of the Year for Single Family. Welcome to a visionary newly built 2025 contemporary trophy where Architectural Art Meets Waterfront Living. At 1100 Sandpiper design, nature, outdoor living, and technology converge in to timeless elegance. Just one mile from iconic 5th Avenue South and 1.8 miles from the Gulf Beaches, this modern waterfront marvel fuses bold architectural artistry with effortless indoor-outdoor living. With nearly 200 feet of direct Oyster Bay corner frontage, a 60-foot dock already in place (with room for more), and a sculptural form that commands attention from every angle, this is Naples’ ultimate statement home. Rooted in the five natural elements: water, air, earth, fire, and stone -the residence exists in perfect harmony with its environment. Water shimmers from every perspective. Bright light and air drifts through vast glass walls and open terraces. Earth blooms in the lush rooftop lawn and tropical gardens. Fire glows through eight fireplaces across the home. Over 7,500 square feet of natural stone, including 40+ full marble slabs, anchors the structure in enduring sophistication. Outdoor living rivals the interior with nearly equal finished square footage: fully screened waterfront lounges, sunrise and sunset terraces, and secluded open-air zones. The newly completed 1,500-square-foot rooftop sanctuary - complete with sunrise and sunset lounges framed by glass railings—creates a sky-level retreat beyond compare. Inside, nearly 4,000 square feet under air offer five bedrooms, five full baths and two custom half baths. Dual maste suites: one on each level - serve as spa-like havens with luxurious en suites and double vanities as well as a steam shower. 1500 square-foot wraparound terrace seamlessly merges the main living space with the outdoors. Nicknamed The Modern Taj Mahal designed by reendowed Stoff Cooney, this home’s gallery-like glass architecture and structural integrity are unmatched. Built with solid stainless-steel engineered commercial flood panels, it stands among Naples’ most resilient and forward-thinking waterfront builds. Sustainability and innovation shine through a high-output solar roof system with Tesla Powerwalls, a 30+ speaker high-fidelity audio network, and eight fireplaces, including a dramatic centerpiece framing the 12×14 hot tub. The grounds evoke a private resort—three poolside fire bowls, six sculptural water features, and 25+ rare exotic palms illuminated by 100+ warm custom landscape lights. This is far more than a luxury residence: it’s a living masterpiece where art, nature, and modern engineering coexist in perfect balance. Quite simply, Naples’ most visionary home with unprecedented levels of modern luxury & technology in every detail.

1100 Sandpiper ST, Naples

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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.