5433 ESSEX AVENUE S, Gulfport, FL 33707

• 4 beds |
• 3 baths |
• 1,992 sqft

Property Description

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.

Listing Status:

Active

Date Added:

September 19, 2026

Data Last Updated:

September 28, 2026 at 5:21AM

Listing Office:

GENSTONE REALTY : 833-396-0092

Listing Agent:

John Blevins : 443-250-1837

Contact:

833-396-0092

MLS ID:

TB8548763

Interior

• General: Cathedral Ceiling(s)Eat-in KitchenElevatorHigh CeilingsLiving Room/Dining Room ComboOpen FloorplanPrimaryBedroom UpstairsSplit BedroomStone CountersVaulted Ceiling(s)Walk-In Closet(s)Window Treatments
• Rooms: Inside UtilityInterior In-Law Suite w/No Private Entry
• Appliances: DishwasherDisposalDryerElectric Water HeaterIce MakerMicrowaveRangeRefrigeratorWasher
• Laundry: Laundry Closet
• Flooring: Wood
• A/C: Central AirWall/Window Unit(s)
• Heating: CentralElectric
• Disability Feature: Accessible Elevator Installed

Exterior

• General: Balcony
• Style: Coastal
• Other Structures: Front PorchDeck
• Parking: Oversized

Construction

• Roofing: Shingle
• Windows: ENERGY STAR Qualified Windows
• General: Vinyl SidingFrameThree Or MoreBlock

Location

• Road/Access: AsphaltPaved
• Originating MLS: Stellar MLS
• County: Pinellas

Lot

• Zoning: SFRBOCA CEIGA PARKLOT 1233-31-16-09612-004-0120
• View: Gulf/Ocean - Partial
• Fencing: Vinyl

Utilities

• Utilities: Cable ConnectedElectricity ConnectedFire HydrantSewer ConnectedWater Connected
• Water: Public
• Sewer: Public Sewer

Financial

• Source: Stellar MLS
• Ownership: Fee Simple