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.
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.
Property Details
Price:
$1,200,000
MLS #:
TB8548763
Status:
Active
Beds:
4
Baths:
2.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
BOCA CEIGA PARK
Neighborhood:
33707stpetesouthpasadenagulfportstpetebch
Listed Date:
Sep 19, 2026
Finished Sq Ft:
1,992
Total Sq Ft:
3,804
Lot Size:
3,838 sqft / 0.08 acres (approx)
Year Built:
2011
See this Listing
Schools
Elementary School:
Gulfport Elementary-PN
Middle School:
Azalea Middle-PN
High School:
Boca Ciega High-PN
Interior
Appliances
Dishwasher, Disposal, Dryer, Electric Water Heater, Ice Maker, Microwave, Range, Refrigerator, Washer
Bathrooms
2 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air, Wall/Window Unit(s)
Flooring
Hardwood
Heating
Central, Electric
Interior Features
Cathedral Ceiling(s), Eating Space In Kitchen, Elevator, High Ceilings, Living Room/Dining Room Combo, Open Floorplan, PrimaryBedroom Upstairs, Split Bedroom, Stone Counters, Vaulted Ceiling(s), Walk-In Closet(s), Window Treatments
Laundry Features
Laundry Closet
Levels
Three Or More
Exterior
Accessibility Features
Accessible Elevator Installed
Architectural Style
Coastal
Attached Garage YN
1
Community Features
Dog Park, Golf Carts OK, Park
Construction Materials
Vinyl Siding, Wood Frame
Covered Spaces
2
Direction Faces
South
Exterior Features
Balcony
Fencing
Vinyl
Garage Spaces
2
Lot Features
City Lot
Parking Features
Oversized
Patio And Porch Features
Deck, Front Porch
Roof
Shingle
Window Features
ENERGY STAR Qualified Windows
Financial
Tax Year
2025
Taxes
$11,723
Map
Community
- Address5433 ESSEX AVENUE S GULFPORT FL
- SubdivisionBOCA CEIGA PARK
- CityGULFPORT
- CountyPinellas
- Zip Code33707
Subdivisions in GULFPORT
- 76392
- 78BURNS F J REALTY COS REV
- ARDMORE HEIGHTS
- BAY ESTATES
- BAY VIEW PARK SEC P
- BAYWOOD
- BAYWOOD SUB
- BAYWOOD SUB 1ST ADD
- BEACHWALK CONDO GULFPORT
- BEACHWAY PARK INC M/H UNREC
- BLACKBERRY PARK
- BOCA CEIGA PARK
- BOCA CIEGA ESTATES
- BOCA CIEGA PARK
- BRUNSON-DOWELL SUB 1
- BURNS F J REALTY COS REV
- CHASE & HOWARDS SUB REV
- CURNS W J SUB
- GOLDEN GLOW GROVE ESTATES 1ST ADD
- GOLFVIEW I CONDO
- GOLFVIEW II CONDO
- GULF GROVE
- GULFPORT HARBOR 1ST ADD
- GULFPORT HARBOR 2ND ADD
- GULFPORT SUB
- HAYNSWORTH HEIGHTS
- HEMPSTEAD ANNEX 1
- HORNERS REP
- HOYTS A A SUB
- JENKINS & BERLS REP
- KIPP’S COLONY ESTATES AT PASADENA YACHT/COUNTRY CL
- KIPPS COLONY AT PASADENA YACHT/CNTRY CLUB
- KIPPS COLONY ESTATES AT PASADENA YACHT/COUNTRY CL
- LAKE BUTLER VILLA COS ADD
- PARK VIEW HEIGHTS
- PASADENA ESTATES SEC C
- PASADENA ESTATES SEC D
- PASADENA ESTATES SEC F
- PASADENA ESTATES SEC G
- PASADENA ESTATES SEC H
- PASADENA ESTATES SECTION C
- PASADENA GARDENS GULFVIEW SEC
- PASADENA GOLF CLUB ESTATES SEC 1
- PASADENA GOLF CLUB ESTATES SEC 4
- PASADENA HEIGHTS
- PELICAN BAY ESTATES AT SKIMMER POINT PH I
- PELICAN BAY YACHT CLUB CONDO
- PELICAN BAY YACHT CLUB CONDO BLDG A
- PELICAN BAY YACHT CLUB CONDO BLDG B
- PINE GROVE
- ROEBUCK PARK
- ROGERS-SCOTT SUB
- ROYAL PALM VILLAGES
- SKIMMER POINT PH II
- SKIMMER POINT PH III
- STAMMS REP
- TANGERINE BUS CENTER SUB
- TILTON COURT
- TORRES ADD SUB OF LT 5
- TOWN SHORES
- TOWN SHORES OF GULFPORT
- VETERAN CITY
- VETERAN PARK
- VILLA DE MARIA
- VILLAS DEL VERDE
- WATERVIEW PARK SEC 1
- WILSON HEIGHTS
Market Summary
Current real estate data for Single Family in GULFPORT as of Oct 20, 2026
81
Single Family Listed
132
Avg DOM
406
Avg $ / SqFt
$840,087
Avg List Price
Property Summary
- Located in the BOCA CEIGA PARK subdivision, 5433 ESSEX AVENUE S GULFPORT FL is a Single Family for sale in GULFPORT, FL, 33707. It is listed for $1,200,000 and features 4 beds, 3 baths, and has approximately 1,992 square feet of living space, and was originally constructed in 2011. The current price per square foot is $602. The average price per square foot for Single Family listings in GULFPORT is $406. The average listing price for Single Family in GULFPORT is $840,087. To schedule a showing of MLS#tb8548763 at 5433 ESSEX AVENUE S in GULFPORT, FL, contact your CENTURY 21 Carioti agent at 2392986550.
Similar Listings Nearby
Courtesy of GENSTONE REALTY. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than CENTURY 21 Carioti include the name of the listing broker. Neither the listing company nor CENTURY 21 Carioti shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 5433 ESSEX AVENUE S
GULFPORT, FL
