About 5433 Essex Avenue S
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.
Features of 5433 Essex Avenue S
| MLS® # | TB8548763 |
|---|---|
| Price | $1,200,000 |
| Bedrooms | 4 |
| Bathrooms | 3.00 |
| Full Baths | 2 |
| Half Baths | 1 |
| Square Footage | 1,992 |
| Acres | 0.08 |
| Year Built | 2011 |
| Type | Residential |
| Sub-Type | Single Family Residence |
| Style | Coastal |
| Status | Active |
Community Information
| Address | 5433 Essex Avenue S |
|---|---|
| Area | St Pete/South Pasadena/Gulfport/St Pete Bch |
| Subdivision | BOCA CEIGA PARK |
| City | GULFPORT |
| County | Pinellas |
| State | FL |
| Zip Code | 33707 |
Amenities
| Parking | Oversized |
|---|---|
| # of Garages | 2 |
| Is Waterfront | No |
| Has Pool | No |
Interior
| 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 |
| Heating | Central, Electric |
| Cooling | Central Air, Wall/Window Unit(s) |
| Fireplace | No |
| # of Stories | 3 |
Exterior
| Exterior Features | Balcony |
|---|---|
| Lot Description | City Lot |
| Roof | Shingle |
| Foundation | Block |
School Information
| Elementary | Gulfport Elementary-PN |
|---|---|
| Middle | Azalea Middle-PN |
| High | Boca Ciega High-PN |
Additional Information
| Date Listed | September 19th, 2026 |
|---|---|
| Days on Market | 1 |
| Zoning | SFR |
| Foreclosure | No |
| Short Sale | No |
| RE / Bank Owned | No |
Listing Details
| Office | GENSTONE REALTY |
|---|