Oyster Bay Real Estate

Oyster Bay Real Estate

Welcome to Oyster Bay, a hidden gem nestled in the heart of Florida's stunning coastline. This charming subdivision offers a unique blend of serene living and vibrant community life, making it an ideal place for families, retirees, and everyone in between. With its lush landscapes and picturesque surroundings, Oyster Bay is a paradise for nature lovers and outdoor enthusiasts alike.

As you stroll through the tree-lined streets, you'll discover a variety of beautifully designed homes that cater to diverse tastes and lifestyles. From modern architectural marvels to classic coastal cottages, there's something for everyone. Many properties boast spacious yards, perfect for family gatherings, gardening, or simply soaking up the Florida sun.

Oyster Bay isn’t just about beautiful homes; it's about community. Residents enjoy a warm and welcoming atmosphere, with plenty of opportunities to connect with neighbors through local events, farmers' markets, and community gatherings. The subdivision is conveniently located near top-rated schools, shopping centers, and recreational facilities, ensuring that all your needs are just a stone's throw away.

For those who love the outdoors, Oyster Bay is surrounded by stunning parks and nature reserves, perfect for hiking, biking, and exploring Florida's unique wildlife. Plus, with the beautiful Gulf Coast beaches just a short drive away, weekend getaways to the sandy shores are always within reach.

Discover the charm and allure of Oyster Bay, where coastal living meets community spirit. Experience the perfect balance of tranquility and convenience in this idyllic Florida subdivision, and make it your forever home. Your dream lifestyle awaits!

Newest Listings in Oyster Bay

1510 Chesapeake Avenue, Naples
$3,899,000
3 Beds ⋅ 4 Baths ⋅ Oyster Bay SubDv.
No bridges between your dock and the Gulf. This Oyster Bay home sits on a canal more than 120 feet wide with direct access to Naples Bay and Gordon Pass, and a private Ipe dock with boat lift, water and power. The rear faces south over a screened, heated pool and overflow spa and a covered outdoor dining area. Inside, 3,062 square feet on one level offer 3 bedrooms plus a den and 3.5 baths in a split plan: the primary suite and one guest bedroom open to the pool, while the second guest bedroom and the den each have their own covered sitting area. The lighthouse-inspired design brings vaulted ceilings, custom millwork, painted detailing and natural light throughout. For the boat owner, the 24 by 24 garage has a 12-foot ceiling with height for car lifts, its own mini-split air conditioning and an oversized closet for tackle and gear. Concrete block construction with vinyl siding, a metal roof, and electric and manual storm shutters, with central air conditioning replaced in 2019 and the water heater in 2025. Built in 2002 and kept in its original finishes, it gives the next owner a sound waterfront home to update to their own taste. Minutes to Tin City, the Bayfront and Fifth Avenue South. Floor plan and 3D tour attached.

1510 Chesapeake Avenue, Naples
1630 Chesapeake Avenue, Naples
$2,700,000
4 Beds ⋅ 3 Baths ⋅ Oyster Bay SubDv.
One or more photo(s) has been virtually staged, AI generated or rendered. Exceptional waterfront opportunity at 1630 Chesapeake Avenue in desirable Oyster Bay, near Royal Harbor. Enjoy southern exposure on a wide, deep-water canal with direct Gulf access and no bridges. The private boat dock accommodates vessels up to about 40 feet, making it ideal for boating enthusiasts. The existing four-bedroom, three-bath home features a new roof, impact windows, and a large pool in a private waterfront setting. The home sustained flooding, and the interior has not been restored, offering an opportunity to renovate to your vision or explore building a new waterfront residence. Just minutes from downtown Naples, Fifth Avenue South’s shopping and dining, and the Gulf beaches, this property combines an outstanding location with exceptional potential.

1630 Chesapeake Avenue, Naples
1420 Jewel Box Avenue, Naples
$3,095,000
3 Beds ⋅ 3 Baths ⋅ Oyster Bay SubDv.
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 Avenue, Naples
1085 SANDPIPER Street, Naples
$7,995,000
5 Beds ⋅ 6 Baths ⋅ Oyster Bay SubDv.
Experience the ultimate in Naples living with this new contemporary water view home, minutes from Fifth Avenue South, with a deeded boat slip, oversized four-car garage and generous storage. Offered fully furnished with a curated art package and a golf cart included — arrive with a suitcase. Completed in 2026 and never lived in, this three-story residence offers approximately 4,400 square feet of elevated living area — five bedrooms, five full baths, a powder room, and a private elevator serving every floor. The primary suite sits on the main living floor, with three guest suites and a loft club room above: a home that lives easily for two, with room for a few guests or a full house. A dramatic three-story glass entry opens to an open-concept living floor with soaring ceilings, contemporary custom built-ins, and walls of glass framing expansive western views over the water and stunning sunsets. The chef’s eat-in kitchen is replete with an oversized island, custom cabinetry, walk-in pantry, and high-end appliances including a professional gas range, plus a wet bar built for entertaining. An east–west sightline carries that light through the house to the outdoor living room, where a built-in kitchen, fireplace and relaxed seating overlook the elevated heated pool and spa. Mature tropical landscaping and privacy screening make it entirely private, and the elevated terrace stays usable year-round. The primary suite is a quiet sanctuary with a spa-inspired bath and dual walk-in closets with custom built-ins. The fifth bedroom is presently appointed as a private office, an elegant work-from-home retreat that reverts to a guest suite whenever needed. Upstairs, three spacious guest suites surround a loft-style club room with wet bar, ideal for morning coffee or an evening cocktail. The lower level adds approximately 1,600 square feet of finished, fully conditioned storage with direct interior access, alongside a climate-controlled four-car garage. A reinforced perimeter wall surrounds the property, with an integrated flood panel system and backup power for genuine peace of mind. The deeded boat slip sits just out the front door, with a private lift, a City-maintained seawall and no-bridge access to Naples Bay and the Gulf. No canal turns, no clearance math, no bridge waits. An ideal lifestyle location close to Fifth Avenue South and Third Street South, renowned worldwide for fine dining, galleries and shopping. The Bayshore Arts District, the Naples Pickleball Center and the Gulf beaches are all close at hand, with Naples and Fort Myers airports an easy drive. New, elevated, west-facing, downtown-adjacent, and boat-ready on day one.

1085 SANDPIPER Street, Naples
1390 Chesapeake Avenue Unit 1390, Naples
$1,499,000
3 Beds ⋅ 2 Baths ⋅ Oyster Bay SubDv.
Completely renovated 3 bedroom, 2 bath, TURNKEY furnished BY ARHAUS, waterfront condo on Naples Bay with Direct Gulf access & 26 ft Boat Slip, NEW ROOF JULY 2026. The interior has been COMPLETELY RENOVATED and NEVER LIVED-IN with luxury finishes and elegant Arhaus furnishings throughout creating a stylish and functional living space including impact windows and doors. Second floor end unit with additional windows flood the home with natural light and stunning bay views. Outdoor living is elevated with a lanai overlooking the water perfect for enjoying spectacular sunsets from this tranquil setting. This boutique community consists of only 6 residences with low Condo Fees, offering a private exclusive atmosphere minutes to 5th Avenue, 3rd Street, the city's world class shopping, dining, arts and white sandy beaches.

1390 Chesapeake Avenue Unit 1390, Naples
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