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$1,300,000

5417 Essex Ave

Gulfport, FL
Active
3
Bedrooms
3
Bathrooms
4,572
Square Feet
0.1
Lot Size (acres)
2014
Year Built
16
Days On Market

Welcome to a turnkey, income-producing coastal retreat in the heart of Gulfport's Historic Waterfront Arts District. This Key West-inspired residence offers 3 bedrooms, 3 bathrooms, and 3,051 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, and a whole-house reverse osmosis system 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, 5417 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.

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Listing Information

Listing Updated
6 days ago
Listed By
John Blevins, 4432501837 · GENSTONE REALTY, 8333960092
MLS#
TB8548759
Source
Stellar MLS
Status
Active

Facts & Features

Location

Community Information

Address
5417 Essex Ave, Gulfport, FL 33707
City
Gulfport
County
Pinellas
Neighborhood
BOCA CEIGA PARK
Zip Code
33707

Architecture

Bedrooms
3
Bathrooms
3
Year Built
2014
Style
Coastal
Construction Materials
Stucco, Block
Building Area
4,572 sq. ft.
Foundation
Slab
Roof
Metal
Levels
Three Or More
Garage
Yes
Garage Spaces
2
Parking Features
Driveway, Attached

Features & Amenities

Interior Features
Cathedral Ceiling(s), Eat-in Kitchen, Walk-In Closet(s), Elevator, High Ceilings, Stone Counters
Appliances
Dryer, Dishwasher, Microwave, Refrigerator, Washer, Disposal, Tankless Water Heater, Cooktop
Flooring
Hardwood
Exterior Features
Storage, Lighting, Balcony
Patio and Porch
Covered, Patio, Wrap Around
Community Features
Sidewalks, Playground, Tennis Court(s), Park
Cooling
Central Air, Zoned
Heating
Electric, Zoned, Central

Property Features

Lot Size
0.1 Acres
Lot Features
Corner Lot
View
Water, Park/Greenbelt
Water
Public
Sewer
Public Sewer
Utilities
Cable Available, Natural Gas Available, Electricity Connected

Square Footage

Total
3,051 sq. ft.

Tax & Financial Information

List Price
$1,300,000
Annual Taxes
$16,841

Schools

100/100
Thurgood Marshall Fundamental
Middle · Grades 06–08 · 1.4 mi
City
St Petersburg
Students
895
Student body
52% White · 34% Black · 6% Asian
Free/reduced lunch
41%
Phone
(727) 522-1737
98/100
Gulfport Montessori Elementary School
Elementary · Grades PK–05 · 0.9 mi
City
Gulfport
Students
662
Parent reviews
5.0★ avg · 2 reviews
Student body
61% Black · 27% White · 8% Hispanic / Latino
Free/reduced lunch
75%
Phone
(727) 893-2643
74/100
Douglas L. Jamerson Junior Elementary
Elementary · Grades PK–05 · 2 mi
City
St Petersburg
Students
536
Parent reviews
5.0★ avg · 4 reviews
Student body
45% Black · 36% White · 10% Hispanic / Latino
Free/reduced lunch
47%
Phone
(727) 552-1703
73/100
Disston Academy
High · Grades 05–12 · 1.5 mi
City
Gulfport
Students
106
Parent reviews
5.0★ avg · 2 reviews
Student body
75% Black · 15% White · 7% Hispanic / Latino
Free/reduced lunch
80%
Phone
(727) 893-1115
64/100
Bear Creek Elementary School
Elementary · Grades PK–05 · 2.1 mi
City
St Petersburg
Students
286
Parent reviews
3.7★ avg · 6 reviews
Student body
52% Black · 25% White · 13% Hispanic / Latino
Free/reduced lunch
82%
Phone
(727) 893-2332
55/100
Charles Britt Academy
Grades M–M · 2.1 mi
City
St Petersburg
Students
26
Student body
50% Black · 31% White · 19% Hispanic / Latino
Free/reduced lunch
12%
Phone
(727) 893-2731
54/100
Extended Transition Countywide
High · Grades 12–12 · 1.5 mi
City
Gulfport
Students
182
Student body
53% White · 30% Black · 11% Hispanic / Latino
Free/reduced lunch
12%
Phone
(727) 893-1115
51/100
Disston Gifted Center
Elementary · Grades 01–05 · 1.5 mi
City
Gulfport
Phone
(727) 893-5580

School ratings are provided for informational purposes only and are subject to change. Attendance boundaries are for reference only — contact the school or district directly to verify enrollment eligibility.

Historical Data

Price History

DateEventPrice
09/18/2026Listed for sale$1,300,000

Listed by John Blevins · GENSTONE REALTY · 8333960092

Listing information provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed by the MLS. Copyright 2026, Stellar MLS. All rights reserved.

Last Updated: September 27, 2026 at 5:07 PM | Source: Stellar MLS | MLS#: TB8548759

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