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$1,200,000

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 1,992 Sq. Ft.
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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.

Full Property Details for 5433 Essex Ave S

General

  • Price: $1,200,000
  • Taxes: $11,723 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: TB8548763
  • Updated: 10/20/2026
  • Added to Site: 46 day(s) ago

Rental Information

  • Min. Lease: No Minimum

Interior

  • Number of Rooms: 4
  • 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
  • Appliances: Dishwasher, Disposal, Dryer, Electric Water Heater, Ice Maker, Microwave, Range, Refrigerator, Washer
  • Furnishings: Turnkey
  • Flooring: Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Laundry: Laundry Closet

Exterior

  • Exterior Features: Balcony
  • Deck/Patio: Deck, Front Porch
  • Porch/Patio/Deck: Deck, Front Porch

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2
  • Parking Features: Oversized

Location

  • Area: 33707 - St Pete/South Pasadena/Gulfport/St Pete Bch
  • County: Pinellas
  • Development Name: 33707 - St Pete/South Pasadena/Gulfport/St Pete Bch
  • Subdivision: BOCA CEIGA PARK
  • Driving Directions: Use GPS
  • Direction Faces: South

School Information

  • Elementary School: Gulfport Elementary-PN
  • Middle School: Azalea Middle-PN
  • High School: Boca Ciega High-PN

Community

  • Community Name: 33707 - St Pete/South Pasadena/Gulfport/St Pete Bch
  • Community Features: Dog Park, Golf Carts OK, Park
  • Management Type: Part Time
  • Mgmt. Company: Part Time

Heating & Cooling

  • Cooling Type: Central Air, Wall/Window Unit(s)
  • Heating Type: Central, Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Cable Connected, Electricity Connected, Fire Hydrant, Sewer Connected, Water Connected

Structural Information

  • Architectural Info: Coastal
  • Architectural Style: Coastal
  • Exterior Const.: Vinyl Siding, Wood Frame
  • Roof: Shingle
  • Windows: ENERGY STAR Qualified Windows
  • Stories/Levels: Three Or More
  • Square Feet: 1,992
  • Sq. Ft. Source: Builder
  • Year Built: 2011

Lot Features

  • Lot Size (Acres): 0.08
  • Lot Size (Sq. Ft.): 3,838
  • Lot Size: 3838
  • Lot Dimensions: 40 x 95
  • Frontage: Street Paved
  • Street/Road Desc.: Paved, Asphalt
  • Fencing (Description): Vinyl

Financial Considerations

  • Tax Amount: $11,723
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: BOCA CEIGA PARK, LOT 12
  • Flood Zone Info: AE
  • APN: 333116096120040120
  • Property ID: 333116096120040120
  • Block/Lot/Section: 4

Listed by Genstone Realty

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Listing agent

— 5433 Essex Ave S —

  • Genstone Realty

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with our affiliated lender
NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 5433 Essex Ave S

School District:Pinellas County School District
NameGradesDistance
Gulfport Montessori Elementary School
2014 52nd Street South, Gulfport, FL 33707
K-50.9 mi
Azalea Middle School
7855 22nd Ave N, St. Petersburg, FL 33710
6-84.5 mi
Boca Ciega High School
924 58th Street South, Gulfport, FL 33707
9-121.6 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 5433 Essex Ave S Get Price Alerts and Save Property

Date
Details
Price
Change
Source
9/19/2026
Listed
$1,200,000
185.71%
MLS
6/06/2019
Sold
$420,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 5433 Essex Ave S

Year
Property Taxes
Change
Tax Assessment
Change
2025
$11,723
-4%
$689,882
-14%
2024
$12,176
5%
$801,869
3%
2023
$11,576
23%
$778,482
47%
2021
$9,393
-10%
$528,857
-22%
2022
$10,396
11%
$673,714
48%
2021
$9,393
13%
$455,129
4%
2019
$8,302
9%
$438,504
10%
2018
$7,584
8%
$398,640
10%
2017
$6,994
2%
$362,400
4%
2016
$6,858
2%
$349,801
2%
2015
$6,721
11%
$342,272
14%
2014
$6,054
7%
$300,522
8%
2013
$5,669
—
$278,166
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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NMLS#: 1598647

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Listed by Genstone Realty

5433 Essex Avenue S, Gulfport, FL 33707 (MLS# TB8548763) is a Single Family property with 4 bedrooms, 2 full bathrooms and 1 partial bathroom. 5433 Essex Avenue S is currently listed for $1,200,000 and was received on September 19, 2026. Want to learn more about 5433 Essex Avenue S? Do you have questions about finding other Single Family real estate for sale in Gulfport? You can browse all Gulfport real estate or contact a Coldwell Banker agent to request more information.

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