Southport On The Bay Homes with Captain's Walk Boat access

Welcome to Southport On The Bay, a hidden gem nestled in the heart of Bonita Springs, Florida. This charming subdivision offers a unique blend of serene waterfront living and vibrant community spirit, making it an ideal destination for families, retirees, and anyone seeking a slice of paradise.

Southport On The Bay boasts an array of beautifully designed homes, each thoughtfully crafted to maximize comfort and style. One of the standout features of this community is the Captain's Walk boat access, allowing residents to embrace the Florida lifestyle to the fullest. Imagine stepping out of your back door and onto your boat, ready to explore the pristine waters of the Gulf of Mexico or enjoy a leisurely day fishing in the nearby estuaries.

The subdivision is surrounded by lush landscapes, creating a tranquil atmosphere that invites relaxation. Residents can take advantage of the community's amenities, including scenic walking paths, picnic areas, and access to local parks. Southport On The Bay is also conveniently located near Bonita Springs' vibrant shopping and dining scene, ensuring that everything you need is just a short drive away.

Whether you're looking for a weekend getaway or a permanent residence, Southport On The Bay offers a unique opportunity to experience waterfront living at its finest. With its stunning homes, boat access, and welcoming community, this subdivision is not just a place to live—it's a lifestyle waiting to be embraced. Come discover your dream home in Southport On The Bay!

Newest Southport On The Bay Homes with Captain's Walk Boat access

$2,695,000

4 Beds ⋅ 3 Baths ⋅ 226020222 MLS

One or more photo(s) has been virtually staged, AI generated or rendered. One or more photo(s) has been virtually staged, AI generated or rendered. Beautiful bayfront residence with direct Gulf-access ideally situated within the exclusive double-gated enclave of Southport on the Bay in North Naples’ highly coveted Barefoot Beach community. A true paradise for boaters and beach lovers alike, this exceptional property offers direct Gulf-access from your private boat dock with dual lifts, just minutes to open water and only a short five-minute walk to the sugar-white sands of Barefoot Beach. This beautifully maintained home features 4 bedrooms + den, 3 bathrooms, a 2019 tile roof, and tile flooring throughout. The spacious kitchen is appointed with light cabinetry and a breakfast bar for casual dining, flowing seamlessly into a bright sitting area surrounded by expansive windows that fill the home with natural light and showcase the stunning bay views. Step outside to the expansive balcony where panoramic bay views create the perfect backdrop for outdoor living and entertaining, overlooking the resort-style pool and spa with a spacious covered lounging area below. The primary suite offers private lanai access through French doors and features an ensuite bath with dual vanities, a glass-enclosed shower, and a separate soaking tub. Optional membership to the exclusive Club at Barefoot Beach provides access to tennis courts, two restaurants, and beachside and poolside food and beverage service. Ideally located near world-class dining, upscale shopping at Mercato and Waterside Shops, Southwest Florida International Airport, and just a short drive to the renowned Fifth Avenue South.

201 San Mateo DR, Bonita Springs

$4,350,000

4 Beds ⋅ 3.5 Baths ⋅ 226007032 MLS

Nestled on a peninsula in North Naples’ premier community “Barefoot Beach,” this beautiful residence sits on one of the most desirable lots with an unrivaled 352 feet of wraparound water frontage for breathtaking Bay views on three sides of the home, direct Gulf-access & Southeastern exposure. This is the ultimate beach & boaters’ delight with deeded beach-access a short walk-away & direct Gulf-access only 10 minutes from your dual boat docks/lifts. This home features hurricane impact windows & doors, new HVACs, new hot water heater, and newly renovated bathrooms. This expansive floor plan spans approximately 4,333 sq ft under air and includes 4 bedrooms + den, 3.5 bathrooms, versatile lower-level flex space, private elevator, tile flooring, and soaring high ceilings. Step outside to your spacious open-air lanai, where breathtaking bay views create a spectacular backdrop for outdoor living. The resort-style pool and spa are surrounded by lush tropical landscaping and enclosed by a fence, offering both privacy and the perfect setting for entertaining or relaxing waterfront. The primary suite serves as its own private sanctuary, featuring stunning water views, private access to an open-air balcony, a large walk-in closet, and a spa-like bath complete with dual vanities, a large glass-enclosed shower, and a standalone soaking tub. Ideally located near fine dining, Mercato, Waterside Shops, RSW International Airport, and the renowned Fifth Avenue South in Naples, this exceptional waterfront estate offers a rare opportunity to own a premier property within the exclusive Southport on the Bay at Barefoot Beach.

195 San Mateo DR, Bonita Springs

$3,375,000

4 Beds ⋅ 3 Baths ⋅ 225069562 MLS

Stunning home nestled on a tranquil peninsula in the double-gated Southport on the Bay in North Naples’ premier community of Barefoot Beach offers breathtaking bay views from nearly every window. A true paradise for boaters and beach lovers, this property boasts direct Gulf-access in minutes (no bridges) and is just a short 5-minute walk to the pristine shores of Barefoot Beach. Designed for the ultimate waterfront lifestyle, this home features a private boat dock, dual boat lifts with 16,000 lb and 10,000 lb capacities, and a dedicated fish cleaning station for avid anglers. Inside, you’ll find 4 spacious bedrooms, tile flooring, wood flooring (Bamboo), and gorgeous wood-paneled ceilings. The home is equipped with brand-new hurricane impact windows (2025), hurricane shutters, new hurricane garage doors (2022), and upcoming 32-inch Garrison Flood Panels to be installed on the garage and lower-level doors, along with new HVACs, a new water heater, and a dedicated space to add an elevator. Additional features include a versatile ground-floor flex space and a newly epoxied garage that can accommodate 4+ cars. Outside, step into your own outdoor haven, complete with a summer kitchen ideal for al fresco dining while soaking in breathtaking bay views. Perfect for entertaining, the expansive lanai features a brand-new picture screen enclosure, a newly resurfaced pool, an outdoor shower, stone waterfall, and a bar area. The beautiful chef’s kitchen features white cabinetry, soft close cabinets, granite countertops, stainless steel appliances, an eat-in area, and a breakfast bar for casual dining. The primary suite serves as a private retreat with its own balcony overlooking the water, and a spa-like bathroom complete with dual vanities, a glass-enclosed shower, and a separate jetted tub. Conveniently located near fine dining, RSW Airport, Mercato, and Waterside Shops, and just 15 miles from the renowned Fifth Avenue in Naples, this home is a true gem in the heart of Southport in Barefoot Beach.

197 San Mateo DR, Bonita Springs

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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.