5417 ESSEX AVENUE S, GULFPORT, FL, 33707
Active12 days on marketListed Sep 18, 2026MLS #TB8548759
About this home
5417 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 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.
Facts & features
The home at a glance
3
Bedrooms
3
Bathrooms
3,051
Sqft
0.1 ac
Lot size
2
Garage
2014
Year built
Three Or More
Levels
$426
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Built from this home's actual numbers — the most recent property-tax bill on record — not generic estimates.
$9,066 /mo · 10% down Conventional, 30-yr fixed at 6%
The assumptions
Above the FHA loan limit for our service areas, so Conventional is the default. VA buyers: switch below — $0 down.
These numbers assume a generic buyer — your credit, down payment and loan program change them. Get the real quote in minutes:
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Run your own numbers
FHA isn’t available at this price — the loan would exceed the $541,287 FHA limit for our service areas.
Estimated payment
$9,066/mo
Includes estimated PMI — it drops off once you reach 20% equity. Taxes reflect the most recent bill on record; insurance is a typical-Florida estimate. Your lender’s numbers will differ. CENTURY 21 Edge partners with Florida’s best lenders.
Value check
Is the price right?
The internet’s favorite home-value number comes from a single automated model that has never seen the street, the finishes, or the view — which is why it routinely misses by tens of thousands of dollars. The edgeAI estimate combines multiple independent data sources with our team’s on-the-ground expertise in this exact market.
vs edgeAI estimate
−19.8%
$/sqft vs BOCA CEIGA PARK
$426 vs $471
Days on market
12 vs 60 typical
Where $426/sqft sits among the 7 homes for sale in BOCA CEIGA PARK
The edgeAI estimate is a starting point, not an appraisal or a broker price opinion. It is generated from public records, listing data and market modeling, and is subject to change once a licensed real estate professional personally inspects the property. Condition, floor, view and lot are not fully captured by any model — ask us for a full comparative market analysis.
Where it sits
Inside Boca Ceiga Park
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Gulfport. See the full Gulfport guide →
Boca Ceiga Park — neighborhood snapshot
Population
653
Median age
62
Median income
$51,714
Median home value
$328,279
Avg household
2
Households w/ children
12%
For the school run
Pinellas County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Gulfport market
$352K → $368K
Gulfport median sold, yr/yr
94.3%
Sale-to-list ratio (12 mo)
6 of 7
BOCA CEIGA PARK have cut their price
Median sold price, Gulfport, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 314% above the GULFPORT 33707 median. See the full Gulfport market guide →
Paper trail
This home's history
Reality check
What actually sold near 5417 ESSEX AVENUE S
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Feb ’26$1,475,000
5421 ESSEX AVENUE S · same community
3 bd · 4 ba · 3,828 sqft · $385/sqft · 79 DOM
Sold · Feb ’26$690,000
2843 57TH STREET S · same community
4 bd · 3 ba · 1,990 sqft · $347/sqft · 4 DOM
Sold · Feb ’26$475,000
3020 56TH STREET S · same community
3 bd · 2 ba · 1,643 sqft · $289/sqft · 142 DOM
Closed-sale data from the MLS, last 12 months, selected for similarity in size and location. No two homes are identical — ask us for a full comparative analysis.
Your home team
The pros in your corner
Buying a home is two conversations — the home and the money. Here’s who handles each, side by side, already working together.
Your agent
Nicholas Giaccone
Director of Agent Success · CENTURY 21 Edge
Tours, negotiation, and every question about 5417 ESSEX AVENUE S — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 5417 ESSEX AVENUE S — before you fall in love.
See it in person
Schedule a tour
Live availability from Nicholas's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
5417 ESSEX AVENUE S FAQs
What would the monthly payment be for 5417 ESSEX AVENUE S?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $9,066/mo — principal and interest, the actual property-tax bill and typical Florida insurance. The payment calculator on this page lets you switch loan type (FHA, Conventional, VA) and adjust the down payment, rate and term.
What are the property taxes on 5417 ESSEX AVENUE S?+
The most recent tax bill on record (2025) was $16,841. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
Are pets allowed at 5417 ESSEX AVENUE S?+
The listing reports pets: Cats OK, Dogs OK, Yes. Communities often layer on breed or weight rules — we'll verify the specifics with the association before you commit.
How does the price compare to other homes in Gulfport?+
At $1,300,000, this home is listed about 234% above the Gulfport median of $389,000. The market section on this page shows how the area is trending.
Which schools are assigned to 5417 ESSEX AVENUE S?+
Gulfport Montessori Elementary School (elementary), Boca Ciega High School (high), Azalea Middle School (middle) — Pinellas County School District. Always verify school assignments with the district before relying on them.
Keep looking
Similar homes nearby
Listing courtesy of GENSTONE REALTY · John Blevins. MLS #TB8548759.
IDX information is 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. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
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