Southport On The Bay Homes with Multi-Story Home Style

Welcome to Southport On The Bay, a hidden gem nestled in the heart of Bonita Springs, Florida, within the picturesque Collier County. This enchanting subdivision offers a harmonious blend of tranquility and luxury, making it the perfect place to call home. With its prime location, residents enjoy easy access to stunning beaches, vibrant shopping districts, and delectable dining options, all while being surrounded by the natural beauty that Florida is renowned for.

One of the standout features of Southport On The Bay is its exquisite multi-story homes. These architectural masterpieces not only provide ample living space but also offer breathtaking views of the lush landscapes and serene waterways that characterize the area. Each home is thoughtfully designed with modern amenities and elegant finishes, ensuring a comfortable and stylish living experience. Whether you're hosting family gatherings or enjoying quiet evenings at home, the spacious layouts of these multi-story residences cater to all lifestyles.

The community itself fosters a sense of camaraderie among residents, with opportunities for socializing and enjoying the great outdoors. Take advantage of the nearby parks, walking trails, and recreational facilities that are perfect for families and individuals alike. Southport On The Bay is not just a place to live; it’s a lifestyle where every day feels like a vacation.

Discover the charm of Southport On The Bay and experience the perfect blend of luxury, comfort, and community in Bonita Springs. Your dream home awaits!

Newest Southport On The Bay Homes with Multi-Story Home Style

$4,250,000

4 Beds ⋅ 3 Baths ⋅ 226026511 MLS

Located within the exclusive, double-gated enclave of Southport on the Bay, just 15 minutes north of Naples, this recently renovated waterfront residence offers a rare combination of close Gulf proximity and direct Bay frontage—a lifestyle pairing that is highly sought after and rarely available. With just a short walk to deeded beach access and direct boating access via private lifts, the property delivers the best of both worlds: beach and boating. Southwestern rear exposure provides optimal sunlight and stunning sunset views over the Bay. • One of the closest homes to the Gulf in Southport • Private homesite with no neighbors on three sides • Direct Gulf access via private boat lifts • Recently renovated condition (move-in ready) • New dock, dock poles and two new electric boat lifts • New sprinkler system • Newly sodded lawn • New $150K of Landscaping • New kitchen cabinets and countertops (quartz) • New refrigerator, cooktop, and built in ovens • New washer and dryer • New HVAC on the ground floor • New pool surfacing • New natural stone pool decking • New fence around the pool. • New pool heater- electric • New patio and pavers leading down to the dock • New landscape lighting • New tile on the entire 2nd floor (living space) • New Hunter Douglas power blinds in family room and master bedroom. • New iSpring water filter under sink • New kitchen faucet, sink, dishwasher and disposal • House painted 2 years ago inside and out • 5 year old metal roof • All pavers just power washed and sealed • New elevator

98 Southport CV, Bonita Springs

$2,249,999

4 Beds ⋅ 4 Baths ⋅ 226025219 MLS

This immaculate 3 story “Florida Beach Style” home is located in the double gated community of Southport on the Bay within beautiful Barefoot Beach and although it is the lowest priced single family home in all of Barefoot Beach it offers everything for the best in Florida beach and boating lifestyle including: over 7,000 Sq Ft of total living area that includes a tropical swimming pool & spa overlooking the landscaped yard, lake with fountain and preserve area for privacy, 3,600 Sq Ft of A/C interior that has been reimagined and completely up-dated with a private elevator to all levels, an open floor plan with fabulous kitchen, large dining and 2 living areas, 4 bedrooms, 4 baths including the ultimate master suite/bath, large covered deck within the screened lanai, walk around porches for easy cleaning and maintenance and two garages with large storage areas left and right (perfect for your kayaks, paddle boards and bikes). Boat docks are available for lease with lifts and no bridges and short distances to the Gulf for premier boating. The beach access is right out the Gate across the street. Finally, to make your move in smooth and easy this property is being offered furnished! Barefoot Beach, Collier County’s premier gated beach to bay community, amenities include 24 hour guards and patrols, private beach, brick pavered Royal Palm lined streets and more. Option to join the Club at Barefoot Beach (located in the community - Note: waitlist) which offers casual & fine dining restaurants, pool & beachside food, drinks, chair service, indoor & outdoor bars, ice cream & coffee shop, tennis courts with pro & a full events calendar. Minutes to Mercato, Coconut Point Mall, Promenade & Waterside, the airports and golfing.

200 Topanga DR, Bonita Springs

$4,505,000

4 Beds ⋅ 4 Baths ⋅ 226025188 MLS

211 San Mateo Drive is a newer constructed luxury beach home in Barefoot Beach, offering refined coastal living just moments from the sand. Designed with architectural detail and modern craftsmanship, this residence captures the relaxed sophistication of one of Southwest Florida's desirable beachside communities. Upon entry, a custom-built floating staircase makes an immediate statement and sets the tone for the quality found throughout. The great room features a floor-to-ceiling temperature-controlled glass wine cellar designed to showcase a 210-bottle collection. The gourmet kitchen is finished with hand-selected quartzite surfaces, a designer chevron mosaic backsplash, bespoke custom cabinetry and a Thermador appliance suite with an induction cooktop. The expansive primary suite offers a private sitting room and a serene balcony overlooking the lake. The spa-inspired primary bath features dual vanities, a Jacuzzi soaking tub, and a multi-functional shower with dual shower heads, a rain shower, three body jets and a hand wand. Outdoor living embraces the Barefoot Beach lifestyle with a gas-heated saltwater pool, raised spa, fully equipped outdoor kitchen and alfresco fireplace. Motorized retractable lanai screens, landscape lighting, a clusia privacy hedge and a Swat mosquito spray system add comfort for year-round enjoyment. 211 San Mateo Drive is a sophisticated beach home where modern design, coastal elegance and Barefoot Beach living come together beautifully.

211 San Mateo DR, Bonita Springs

$2,995,000

6 Beds ⋅ 4.5 Baths ⋅ 226018027 MLS

This one owner Barefoot Beach 6 bedroom/5-1/2 bath home is located in the double gated community of Southport on The Bay in convenient North Naples/Collier County. It is situated on a large lakefront lot just a short walk to beautiful Barefoot Beach via a dedicated beach access and to your own boat dock & lift on the bay with direct Gulf of America access and no bridges. This home’s floor plan is perfect for large family gatherings and entertaining and lilies on one level. Main living level has a large great room, dining room, in-eat kitchen, with direct access to the large outdoor areas plus the master bedroom suite separate shower & bath, walk in closets, den/office, 2 guest bedrooms, and large storage areas. The 2nd floor offers guest bedrooms and baths. There is a large walk-out to the landscaped yard and pool area that overlooks the lake and fountain. There is a separate work area on the lower level, a 2 car garage and private elevator to all 3 levels. The outdoor landscaping provides privacy surrounding the property and for your enjoyment of the pool, spa, and 2 story screened lanai. This home is in its original condition and ready for your to transform it into your own piece of paradise. Nestled in Collier County’s gated Barefoot Beach community amenities include 24 hour guards and patrols. Option to join the Club at Barefoot Beach (located in the community) which offers casual & fine dining restaurants, pool & beachside food, drinks, chair service, indoor & outdoor bars, ice cream & coffee shop, tennis courts with pro & a full events calendar. (waitlist with usage during wait period). Minutes to Mercato, Promenade & Waterside, the airports, dining, entertainment and golfing.

192 Topanga DR, Bonita Springs

$3,895,000

4 Beds ⋅ 3.5 Baths ⋅ 225079842 MLS

Beautiful Gulf-access estate with breathtaking bay views in the exclusive, double-gated Southport on the Bay, located within North Naples’ highly sought-after Barefoot Beach community. With coveted Southern exposure, you’ll enjoy spectacular sunsets and prime sun over the pool. A true paradise for boaters and beach lovers, this property offers direct Gulf-access (no bridges) in minutes from your private dock with dual lifts and is just a short 5-minute walk to the pristine sands of Barefoot Beach. Offering 4,927 sq ft of living space, this coastal retreat features 4 bedrooms + den, 3.5 baths, tile and wood flooring, hurricane-impact windows, storm shutters, new HVACs (2023 & 2020), BRAND-NEW FLOOD BARRIER SYSTEM, and a NEW 2025 TILE ROOF. The open-concept chef’s kitchen showcases white cabinetry, granite countertops, high-end appliances including a gas & electric range, an oversized island with breakfast bar seating, and flows seamlessly into a bright sitting/dining area with expansive windows that fill the space with natural light. Step outside to a spacious balcony with panoramic bay views overlooking the large pool—an ideal setting for outdoor living and entertaining. The primary suite features elegant French doors to the upper balcony and a generous en-suite bath with dual vanities, a soaking tub, and frameless glass shower. Additional highlights include a ground-floor flex space, private elevator, 4-car garage (with a lift), wet bar with built-in beverage cooler, wine storage room, and a cozy gas fireplace. Optional membership to the exclusive "Club at Barefoot" provides access to tennis, two restaurants, beachside food and beverage service, and more. 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 Barefoot Beach.

80 Southport CV, 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.