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4 Beds
3 Baths
1,992 sqft

$1,200,000

5433 ESSEX AVE S, GULFPORT FL, 33707

Price per sqft$602.41
Built in2011
Property size1,992 sqft
Property typeResidential
Courtesy of GENSTONE REALTY, John Blevins  Listing Contact: 833-396-0092

Overview

Active

Listed Sep 19, 2026

Updated 11 days ago

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.

$7,984/mo

Est. mortgage payment based on a $1,200,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
TB8548763

Interior Features

Bedrooms
4
Bathrooms
3
Cooling
Yes
Heating
Yes
Basement
No

Exterior Features

Lot Size
0.09 Acres

Other Property Details

Taxes
$11,723
Tax Frequency
Annually
Association Fee Frequency
Monthly
Garage
Yes
View
Yes
Pets Allowed
Yes
55+/Senior Community
No

Listings courtesy of Stellar MLS as distributed by MLS GRID

All information deemed reliable but not guaranteed and should be independently verified. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) nor Upwell Realty shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Properties displayed may be listed or sold by various participants in the MLS. 

Based on information submitted to the MLS GRID as of 4:49 AM UTC on 10/9/2026. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

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