Southport on the Bay

Found within the exclusive gated beach community of Barefoot Beach in North Naples, Southport stands as a serene and secluded enclave, boasting Gulf access homes coupled with remarkably low HOA fees. A mere stroll away from the private beach access through Barefoot Beach, residents enjoy easy access to the shimmering Gulf waters via a short boat ride. Elevating the living experience, each home is thoughtfully perched upon pilings, granting a 3-story elevation above ground level, providing captivating views. Along the palm tree-lined streets, brick pavers gracefully wind their way through the community, complemented by impeccably manicured landscaping adorning every single-family home, rendering Southport a truly picturesque coastal haven.

Real Estate Statistics

Average Price	$3.9M
Lowest Price	$2.2M
Highest Price	$5.3M
Total Listings	15
Avg. Days On Market	134
Avg. Price/SQFT	$1K

Property Types (active listings)

Browse the latest listings in Southport on the Bay, or continue reading to learn more about this beautiful community.

Browse Southport on the Bay Real Estate

• All Listings
• Over $1,000,000

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New

$2,999,000

198 Topanga Dr, Bonita Springs

6 Beds 4 Baths 3,950 SqFt Residential MLS® # 226009278

Barry DeNicola Realty Inc

$4,495,000

195 San Mateo Dr, Bonita Springs

4 Beds 4 Baths 4,333 SqFt Residential MLS® # 226007032

John R Wood Properties

Open House

$4,100,000

68 Southport Cv, Bonita Springs

4 Beds 4 Baths 4,735 SqFt Residential

Open House

Sun, Mar 8th, 2026 @ 1pm - 4pm

MLS® # 226005514

Compass Florida LLC

$3,950,000

54 Southport Cv, Bonita Springs

5 Beds 4 Baths 2,545 SqFt Residential MLS® # 226003845

John R Wood Properties

$2,990,000

↓ $510,000

94 Southport Cv, BONITA SPRINGS

3 Beds 2 Baths 1,888 SqFt Residential MLS® # 225083248

Barry DeNicola Realty Inc

$4,400,000

208 San Mateo Dr, Bonita Springs

4 Beds 5 Baths 5,079 SqFt Residential MLS® # 225080999

John R Wood Properties

$4,250,000

66 Southport Cv, Bonita Springs

3 Beds 4 Baths 3,240 SqFt Residential MLS® # 225076396

John R. Wood Properties

$2,995,000

↓ $755,000

192 Topanga Dr, Bonita Springs

6 Beds 5 Baths 3,697 SqFt Residential MLS® # 225073350

Barry DeNicola Realty Inc

$4,505,000

↓ $20,000

211 San Mateo Dr, BONITA SPRINGS

4 Beds 4 Baths 4,000 SqFt Residential MLS® # 225075343

Premier Sotheby's Int'l Realty

$4,150,000

195 Topanga Dr, Bonita Springs

4 Beds 7 Baths 4,704 SqFt Residential MLS® # 225070132

John R Wood Properties

$5,295,000

179 Topanga Dr, BONITA SPRINGS

4 Beds 5 Baths 5,563 SqFt Residential MLS® # 225071213

John R Wood Properties

$3,450,000

↓ $45,000

197 San Mateo Dr, BONITA SPRINGS

4 Beds 3 Baths 2,976 SqFt Residential MLS® # 225069562

John R Wood Properties

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Discover Southport on the Bay Homes For Sale

The community of Southport on the Bay is a tropical paradise for homebuyers. With Beach Access, Gulf access, and a central location to both Bonita Springs and Naples you’ll find no other gated Gulf access community as conveniently located and with a Naples address.

Within the gates of the private beach community of Barefoot Beach, ranked one of the top ten beaches in the USA multiple years, you’ll find one of Collier County’s best kept secrets for beachgoers. Miles of nature preserve and pristine beaches can be found within the Barefoot Beach preserve located at the Southern most pointe of the community but residents of Barefoot Beach and the subdivisions within have the availability to join the Barefoot Beach club, a private beach club offering tennis, world class dining, and 5 star service both within the restaurant and on the beach.

Homes within Southport on the Bay offer luxury finishes, 4+ garages, over 3,000 sq. ft. of living space, tranquil views of Hickory Bay and/ or natural mangrove preserves. Most homes offer a private pool, plenty of covered lanai space and high-end features and design options to impress the most discerning of buyers

Why Choose Southport on the Bay?

Real Estate is all about location and there are few locations that offer the single family Gulf access boating options with the security of a private gated community. On top of the quick access by boat to the Gulf of Mexico, Southport on the Bay offers access to one of the country’s top beaches, Barefoot Beach.

Whether you’re looking for a full time residence or second home this community is a great place to choose for all of your real estate needs. At KEY Real Estate we believe each buyer is purchasing a lifestyle and not just a home or condo. You have to feel comfortable and at ease when enjoying your home and with the assistance of KEY Real Estate and the real estate experts we employ we’ll help you find the perfect property.

Other Notable Features Include:

•        24-hour patrolling guard gate staff.
•        Luxury living at its finest.
•        Close proximity to the area’s top destinations and attractions.
•        Low homeowners association fees.
•        Numerous shopping and dining opportunities close-by in North Naples and Naples.

For best-in-class service when it comes to Southwest Florida real estate, contact Kevin Yankow and his team now. Whether you're buying or selling, we'll be there for you.