5429 ESSEX AVENUE S, GULFPORT, FL, 33707
Active154 days on marketListed Mar 17, 2026MLS #TB8457726
About this home
5429 ESSEX AVENUE S
JUST REDUCED $90,000! Exceptional Value Meets Income-Producing Potential in Gulfport's Historic Waterfront District. A rare opportunity to own a fully furnished, Key West-inspired coastal retreat offering short-term vacation rental potential, breathtaking Boca Ciega Bay views, and one of the most walkable locations in Gulfport's Historic Art District. Whether you're searching for a high-performing Airbnb/VRBO investment, second home, or full-time waterfront residence, this turnkey property delivers an unmatched combination of lifestyle, luxury, and exceptional value. Just steps from Gulfport's charming downtown, you'll enjoy award-winning restaurants, art galleries, boutique shopping, waterfront parks, marinas, live entertainment, and the beloved Tuesday Fresh Market. This is Florida coastal living at its finest. Designed to maximize indoor-outdoor living, the home features multiple private balconies and expansive outdoor entertaining spaces overlooking Veterans Park and Boca Ciega Bay—perfect for morning coffee, sunset cocktails, or simply soaking in the waterfront atmosphere. Inside, an open-concept floor plan is filled with natural light and thoughtfully designed for entertaining. The gourmet kitchen showcases stone countertops, abundant cabinetry, generous prep space, and premium finishes that make hosting effortless. The luxurious primary suite offers a peaceful retreat with a professionally designed walk-in closet and a spa-inspired ensuite featuring dual vanities, a whirlpool soaking tub, and an oversized walk-in shower. Two additional guest bedrooms each enjoy private balconies with beautiful water views and refreshing coastal breezes. Built for long-term durability and low-maintenance ownership, this exceptional home includes an elevator, impact-rated windows, Hardie plank siding, Trex decking, synthetic turf landscaping, and a whole-home solar system that helps keep utility costs remarkably low. The oversized two-car garage offers abundant storage for vehicles, kayaks, paddleboards, golf carts, bicycles, and all your beach gear. Located just minutes from Downtown St. Petersburg, award-winning Gulf beaches, championship golf, marinas, and Tampa Bay's premier attractions, this move-in-ready residence is equally suited as a luxury primary home, seasonal escape, or income-producing investment. With a recent $90,000 price improvement, this is an exceptional opportunity to own one of Gulfport's premier waterfront homes at an incredible new value. Schedule your private showing today.
Facts & features
The home at a glance
4
Bedrooms
3
Bathrooms
2,340
Sqft
0.09 ac
Lot size
2
Garage
2012
Year built
Three Or More
Levels
$517
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.
$8,372 /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
$8,372/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
+40.2%
$/sqft vs BOCA CEIGA PARK
$517 vs $466
Days on market
154 vs 64 typical
Where $517/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 298% above the GULFPORT 33707 median. See the full Gulfport market guide →
Paper trail
This home's history
Reality check
What actually sold near 5429 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$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
Sold · Aug ’26$600,000
2921 DUPONT STREET S · same community
2 bd · 2 ba · 1,350 sqft · $444/sqft · 81 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
David Ramirez
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 5429 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 5429 ESSEX AVENUE S — before you fall in love.
See it in person
Schedule a tour
Pick a day that works — this goes straight to David's phone and CRM.
Straight answers
5429 ESSEX AVENUE S FAQs
What would the monthly payment be for 5429 ESSEX AVENUE S?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $8,372/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 5429 ESSEX AVENUE S?+
The most recent tax bill on record (2024) was $14,749. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
How does the price compare to other homes in Gulfport?+
At $1,210,000, this home is listed about 223% above the Gulfport median of $375,000. The market section on this page shows how the area is trending.
Which schools are assigned to 5429 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.
The brief
Four things that matter here
01Positioned at the premium end
$1,210,000 runs 298% above the GULFPORT 33707 median — but at 2,340 sqft it's also nearly twice the size of the typical Gulfport listing.
02Water views
The water view is part of what you're buying — views hold value independently of the structure.
03Time on market is leverage
154 days on market against a Gulfport median of 64 — sellers in this position are usually ready to negotiate.
04The price has already moved
Listed at $1,300,000, now $1,210,000 — a $90K cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of KELLER WILLIAMS ST PETE REALTY · Tricia Dooley. MLS #TB8457726.
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.
Never miss a listing
New Gulfport homes, in your inbox
Like 5429 ESSEX AVENUE S but not quite? A daily digest of every new listing in Gulfport — straight from the MLS, hours after it goes live. Unsubscribe anytime.
Just watching this one home? Ask David to ping you on any price or status change →