Oyster Bay Homes with Pool Amenities

Welcome to Oyster Bay, a hidden gem nestled in the heart of Florida, where coastal charm meets suburban tranquility. This picturesque neighborhood is renowned for its lush landscapes, friendly community vibe, and proximity to stunning waterfront views. Whether you’re a young professional, a growing family, or a retiree looking for a peaceful retreat, Oyster Bay offers something for everyone.

The allure of Oyster Bay doesn’t stop at its scenic beauty; it also boasts a diverse selection of homes, many of which feature coveted pool amenities. Imagine stepping out into your backyard oasis, where you can bask in the Florida sunshine, host summer barbecues, or enjoy a refreshing swim in your private pool. These homes are designed for both relaxation and entertainment, providing the perfect backdrop for creating cherished memories with family and friends.

As a resident of Oyster Bay, you'll enjoy easy access to nearby parks, nature trails, and a variety of shopping and dining options. The area is also known for its excellent schools and community events, fostering a strong sense of belonging among neighbors. With its ideal location, you can relish the best of both worlds—secluded living with the vibrant energy of nearby urban attractions.

Discover the charm of Oyster Bay today, where your dream home with a pool awaits. Experience the ultimate Florida lifestyle in this enchanting neighborhood, where every day feels like a vacation!

Newest Oyster Bay Homes with Pool Amenities

$449,900

2 Beds ⋅ 2 Baths ⋅ 226026545 MLS ⋅ Chesapeake Manor BLDG.

Experience the best of Naples waterfront living in this beautifully remodeled residence in the prestigious Royal Harbor community. Offering tranquil canal views, passing boats, and a bright contemporary design. This exceptional coastal retreat is just minutes from the white-sand Gulf beaches, world-class dining, and boutique shopping of Old Naples. Extensively remodeled throughout, this move-in-ready home features impact-resistant windows, fresh interior paint, porcelain tile flooring, and a stunning new kitchen with updated cabinetry, quartz countertops, and stainless-steel appliances. Both bathrooms have been completely renovated with elegant finishes. Ideally positioned on a desirable Chesapeake Manor the thoughtfully designed floor plan offers two spacious bedrooms, two beautifully updated bathrooms, a designated parking space, and a private storage room. Chesapeake Manor is an intimate, low-density waterfront community with only 16 residences, offering privacy, charm, and a relaxed coastal lifestyle. Located in one of Naples' most sought-after waterfront neighborhoods, Royal Harbor provides quick access to boating, downtown Naples. Whether you're searching for a full-time waterfront residence, a seasonal getaway, or an exceptional investment opportunity, this beautifully updated home offers the perfect combination of luxury, location, and carefree coastal living.

1417 Chesapeake AVE Unit 106, Naples

$550,000

2026024008 MLS

Discover a rare opportunity to own two contiguous premier marsh front homesites in the highly sought after Oyster Bay Harbour community. With two lots, buyers have the opportunity to create an expansive homesite, accommodate a larger floor plan, enhance outdoor living spaces, and preserve additional privacy. These expansive lots offer over two acres of combined waterfront living, showcasing breathtaking panoramic marsh views and spectacular sunrises over Amelia Island. Enjoy the tranquiltiy of marsh front living while remaining just minutes from historic downtown Fernandina Beach, Amelia Island's renowed beaches, championship golf, fine dining and world class boating and fishing. Residents of Oyster Bay Harbor enjoy a gated community known for its luxury homes, natural beauty and proximity to the Intracoastal waterway. One of Oyster Bay Harbour's most coveted amenities is the private Oyster Bay Yacht Club and Marina. The marina provides direct access to the Intercoastal Waterway and Atlantic Ocean, making it an ideal home base for boating enthusiasts. Property owners also have access to the Oyster Bay Yacht Club lifestyle, featuring waterfront dining, social activities, marina amenities, and a vibrant coastal community atmosphere. Whether you're looking to build your forever home, a coastal retreat, or secure a premier homesite in one of Northeast Florida's most desirable communities, this unique double-lot offering presents an exceptional opportunity.

96600 & 96588 Soap Creek, Fernandina Beach

$425,000

2 Beds ⋅ 2 Baths ⋅ 226021302 MLS ⋅ Cherrystone Court BLDG.

Strategically located end-unit waterfront condo with extra windows, canal views, and an incredible boating setup in Naples. This charming first-floor 2-bedroom, 2-bath residence includes a brand-new deeded 30-foot boat dock with electric and water, plus a new wooden dock and seawall. Enjoy direct Gulf access with no bridges through Naples Bay, making this a rare opportunity at this price point. Inside, the condo features fresh paint, granite countertops, stainless steel appliances, and inviting living space with peaceful views of the canal and boat dock. The end-unit location adds extra natural light and a more open feel. The residence is comfortable as-is while also offering the opportunity to personalize and update over time to create your ideal Naples waterfront retreat. Cherrystone Court is a 55+ community offering a community pool and BBQ/grill area in a relaxed waterfront setting. Ideally located near Royal Harbor, Naples Bay, Tin City, Bayfront, 5th Avenue, 3rd Street, dining, shopping, beaches, and all the best of the Naples lifestyle. Whether used as a permanent residence, seasonal escape, or investment opportunity, this is a rare chance to own a waterfront condo with a private deeded dock and no-bridge Gulf access in one of Naples’ most desirable boating locations.

1200 Cherrystone CT Unit B108, Naples

$649,900

2 Beds ⋅ 2 Baths ⋅ 226016825 MLS ⋅ Four Winds BLDG.

Step into this move-in-ready, well maintained, fully updated condo and experience the best of Naples waterfront living. This 2-bedroom, 2-bath home sits directly on a canal with partial Naples Bay views, overlooking the Tin City area—and offering stunning sunsets each evening from the comfort of your own space. With 5th Avenue South, 3rd Street, and multiple Gulf beach access points just 5–10 minutes away, you’ll enjoy unmatched proximity to Naples’ top boutiques, restaurants and pristine beaches. A deeded 26' boat dock is included, providing direct access to the bay. Cruise to Tin City or Bayfront for dinner, fish the nearby mangroves or open Gulf, or head to famous Keewaydin Island—just a short ride by boat. The condo features a long list of recent upgrades: brand-new hurricane-impact windows with a transferable warranty, a new roof and electrical service, updated kitchen and bathrooms, a new soaking tub, new flooring, and a 2-year-old AC system and appliances. The community pool is being fully renovated, and the assessment has already been covered. This is a rare opportunity to own a beautifully updated waterfront home in a prime Naples location—without the long commute from the outskirts. Whether you’re seeking a vacation getaway or a full-time residence, this condo offers convenience, comfort, and nightly sunsets that make every day feel like a getaway.

1100 Little Neck CT Unit F52, Naples

$649,000

3 Beds ⋅ 2 Baths ⋅ 226016242 MLS ⋅ Four Winds BLDG.

Welcome to your Waterfront Escape with BOAT LIFT - this beautifully maintained first-floor, 3-bedroom, 2-bathroom furnished condo offers the perfect blend of comfort, convenience, and coastal living. Step inside to find a bright, open layout with tasteful furnishings throughout, making this home truly move-in ready. This spacious living and dining areas flow seamlessly to a screened lanai, where you can relax and enjoy tranquil canal views and gentle breezes. The kitchen is well-dashed appointed, with ample cabinetry and counter space, ideal for both everyday living and entertaining. The primary suite features a private bath and generous closet space, while two additional bedrooms provide flexibility for guests, a home office, or family living. What truly sets this property apart is the included deeded 25ft boat dock with lift, offering direct canal access - perfect for boating enthusiasts looking to get on the water with ease. Additional highlights include convenient first-floor access, elegantly furnished for immediate enjoyment or rental potential, laundry in residence, assigned parking, and peaceful waterfront setting. Whether you're seeking a fulltime residence, seasonal retreat or investment opportunity, this condo delivers the ultimate Florida lifestyle -just minutes from open water and dining and shopping on 5th Ave, 3rd Street, and Bayshore Drive. Boat, relax, and live the waterfront Dream!

1200 Blue Point AVE Unit A2, Naples

$779,000

2 Beds ⋅ 2.5 Baths ⋅ 226008835 MLS ⋅ Escondido Marina BLDG.

Stop dreaming and start living location, elegance and boater's paradise are converged in this 1,960-square-foot Royal Harbor gem! This isn't just a condominium, it's a direct Gulf-access lifestyle with no bridges standing between you and open water. Whether you're guiding your boat from your private 28-foot dock to Keewaydin island or enjoying sunset views of Naples Bay from your south-facing balcony, the Gulf is practically your backyard. Outside, new docks and a recently renovated heated pool are featured. Inside, the two-floor condominium features travertine flooring, elegant tray ceilings, and a spacious kitchen complete with stainless steel appliances and granite countertops. Upstairs, you'll find two oversized primary en suites with their private balconies. Whether you're biking to the sugar sand beaches or dining on 5th Avenue South, this is the permanent vacation you've been waiting for.

1400 Blue Point AVE Unit 202, Naples

$1,099,000

2 Beds ⋅ 2 Baths ⋅ 226008397 MLS ⋅ Chesapeake Point BLDG.

A rare opportunity of a one-of-one property in the highly sought-after Oyster Bay enclave of Naples. Perfectly positioned on the shimmering waters of Naples Bay, this exceptional waterfront residence captures truly breathtaking, unobstructed bay views, modern elegance, and direct boating access to the Gulf. Completely renovated and thoughtfully reimagined, the home offers stunning vistas from nearly every living space — including the main living area and both bedrooms — creating a seamless and constant connection to the tranquil coastal setting. Tucked away at the end of a peaceful cul-de-sac, the property includes a deeded boat dock with immediate Gulf access, making it a boater’s dream. Coveted Southern and Western exposures flood the residence with natural light throughout the day and provide a spectacular backdrop for Naples’ renowned sunsets, best enjoyed from the comfort of two private balconies. Inside, a refined contemporary aesthetic defines the fully updated interior. Luxury flooring flows throughout the residence, complemented by a stylish chef’s kitchen featuring stainless steel KitchenAid appliances, quartz and quartzite surfaces, soft-close cabinetry, and modern designer lighting. Motorized blinds and impact-resistant windows and doors offer both convenience and peace of mind. Both bathrooms have been beautifully renovated with spa-inspired finishes, sleek vanities, and spacious walk-in showers, delivering a true retreat experience. Outdoor living is equally captivating, with two private balconies offering peaceful spaces to relax and take in the ever-changing waterfront scenery. The energy of Naples Bay comes alive daily — from dolphins and manatees gliding through the water to the mesmerizing parade of passing boats — creating a dynamic yet tranquil coastal backdrop that is uniquely Naples. Located within the intimate waterfront community of Chesapeake Point, residents enjoy a quiet and private atmosphere just minutes from the vibrant energy of downtown Naples. World-class dining, boutique shopping, and cultural attractions along Fifth Avenue South are easily accessible by foot or bicycle. Whether as a full-time residence or seasonal coastal escape, this extraordinary bayfront property embodies refined waterfront living in one of Naples’ most desirable locations.

1302 CHESAPEAKE AVE Unit A3, Naples

$425,000

2 Beds ⋅ 2 Baths ⋅ 224091962 MLS ⋅ Cherrystone Court BLDG.

NEW DEEDED BOAT DOCK with Royal Harbor condo for $425K! Amazing price point for this area of town! Condo comes with a brand new 30' deeded boat dock with direct access and no bridges to Naples Bay! Perfect for a permanent home, a peaceful escape, or use for investment purposes. This is your chance to own in a prime Naples neighborhood and wake up to your own peaceful waterfront backyard with your boat parked right below you! Captivating eastern exposure water view from your master bedroom and screened lanai overlooking the tranquil canal as well as a short stroll or bike ride to 5th Avenue. This 55+ community offers endless days of serene laid-back living with a community pool and grill area providing the perfect setting for entertaining, and the proximity to the beach and downtown hotspots such as 3rd Street, Bayfront, and Tin City means the best of Naples is right at your fingertips. It's time to live a life that truly embodies the Naples lifestyle. Do not miss this opportunity!

1200 CHERRYSTONE CT Unit B209, 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.