5433 ESSEX AVE S — photo 1
5433 ESSEX AVE S — photo 2
5433 ESSEX AVE S — photo 3
5433 ESSEX AVE S — photo 4
5433 ESSEX AVE S — photo 5
5433 ESSEX AVE S — photo 6
5433 ESSEX AVE S — photo 7
5433 ESSEX AVE S — photo 8
5433 ESSEX AVE S — photo 9
5433 ESSEX AVE S — photo 10
5433 ESSEX AVE S — photo 11
5433 ESSEX AVE S — photo 12
5433 ESSEX AVE S — photo 13
5433 ESSEX AVE S — photo 14
5433 ESSEX AVE S — photo 15
5433 ESSEX AVE S — photo 16
5433 ESSEX AVE S — photo 17

$1,200,000

5433 ESSEX AVE S, GULFPORT, FL 33707

Active
4
Beds
2
Garage

Property details

Type Residential
MLS # MFR811104022
Listed Sep 15, 2026
Days on market 53
HOA No
Pool No
County Pinellas
Data source Stellar MLS

About this home

Welcome to a turnkey, income-producing coastal retreat in the heart of Gulfport's Historic Waterfront Arts District. This Key West-inspired residence offers 4 bedrooms, 2.5 bathrooms, and 3,804 square feet of light-filled living space with sweeping views of Boca Ciega Bay and Veterans Park just steps from the front door. Currently operating as a successful short-term rental, the home is being sold fully furnished and rental-ready — a rare opportunity to step into an established, cash-flowing vacation rental from day one. Existing bookings, guest reviews, and operating history are available to qualified buyers upon request, making this an ideal acquisition for investors, 1031 exchange buyers, or second-home owners seeking offset income. Inside, soaring cathedral ceilings, a spacious great room, warm wood flooring deliver the elevated finishes today's guests and homeowners expect. Multiple porches and balconies showcase the water views and capture Gulf breezes, while the layout comfortably sleeps a full group without sacrificing privacy. Location is everything: a one-minute walk to Veterans Park and the Gulfport waterfront, minutes to the shops, restaurants, art galleries, and live music of Beach Boulevard, and a quick drive to St. Pete Beach, downtown St. Petersburg, and Tampa International Airport — the exact walkability and lifestyle that keep this property booked. Whether you're expanding a short-term rental portfolio or looking for a coastal residence that pays for itself between visits, 5433 Essex Ave S is a rare turnkey offering in one of Florida's most sought-after small-town waterfront communities. STR certificate and licenses in place and transferable subject to city approval.

Keep exploring

Talk to the human who knows the house. Imagine that.

No spam. This goes straight to the home’s actual representative.

Create a free account to save this home and get alerts.

Data source

Stellar MLS

MLS #MFR811104022

Compare
+ Drag a home here to compare specs
+ Drag a home here to compare specs
+ Drag a home here to compare specs
Compare