815 LAKE JESSIE DRIVE, WINTER HAVEN, FL, 33881
Active82 days on marketListed May 15, 2026MLS #S5149974
About this home
815 LAKE JESSIE DRIVE
Step into timeless elegance with this stunning Mediterranean-style estate in the heart of Winter Haven. Offering over 4,100 square feet of living space, this one-of-a-kind property features a private casita, private pool, and endless possibilities for multi-generational living, guest accommodations, or a home office. Recent updates include a new roof and new AC, giving buyers peace of mind while preserving the home's unique character and charm. Enjoy spacious living areas, beautiful architectural details, and plenty of room for entertaining both indoors and outdoors. With no HOA, ample parking for boats, RVs, and recreational vehicles, and a prime location near Winter Haven's famous Chain of Lakes, this property combines flexibility, privacy, and convenience. Whether you're looking for a family retreat, a home with income potential, or a distinctive property that stands out from the ordinary, this exceptional residence is a must-see. Schedule your private tour today and discover everything this remarkable home has to offer!
Facts & features
The home at a glance
4
Bedrooms
4
Bathrooms
4,128
Sqft
0.34 ac
Lot size
2
Garage
1949
Year built
One
Levels
$143
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.
$4,160 /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
$4,160/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.
$/sqft vs Winter Haven actives
$143 vs $170
Days on market
82 vs 47 typical
Where $143/sqft sits among the 400 Winter Haven actives
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 Winter Haven
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Winter Haven. See the full Winter Haven guide →
WINTER HAVEN 33881 — neighborhood snapshot
Population
39,189
Median age
43.6
Median income
$53,867
Median home value
$177,400
Avg household
2.61
Households w/ children
3,730
For the school run
Polk County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Winter Haven market
$283K → $280K
Winter Haven median sold, yr/yr
97.2%
Sale-to-list ratio (12 mo)
197 of 400
Winter Haven actives have cut their price
Median sold price, Winter Haven, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 141% above the WINTER HAVEN 33881 median. See the full Winter Haven market guide →
Paper trail
This home's history
Reality check
What actually sold near 815 LAKE JESSIE DRIVE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Jun ’26$265,000
908 LAKE JESSIE DRIVE · same community
3 bd · 2 ba · 1,200 sqft · $221/sqft · 14 DOM
Sold · Apr ’26$195,000
2007 40TH STREET NW
3 bd · 2 ba · 3,304 sqft · $59/sqft · 359 DOM
Sold · Mar ’26$360,000
10 PILOT PLACE
3 bd · 3.5 ba · 2,798 sqft · $129/sqft · 191 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 815 LAKE JESSIE DRIVE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 815 LAKE JESSIE DRIVE — 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
815 LAKE JESSIE DRIVE FAQs
What would the monthly payment be for 815 LAKE JESSIE DRIVE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $4,160/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 815 LAKE JESSIE DRIVE?+
The most recent tax bill on record (2025) was $7,136. 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 815 LAKE JESSIE DRIVE?+
The listing reports pets: 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 Winter Haven?+
At $590,000, this home is listed about 107% above the Winter Haven median of $285,000. The market section on this page shows how the area is trending.
Which schools are assigned to 815 LAKE JESSIE DRIVE?+
Lake Alfred Polytech Academy (middle), Fred G. Garner Academy (elementary), Winter Haven Senior High School (high) — Polk County School District. Always verify school assignments with the district before relying on them.
The brief
Three things that matter here
01Positioned at the premium end
$590,000 runs 141% above the WINTER HAVEN 33881 median — but at 4,128 sqft it's also nearly 2 times the size of the typical Winter Haven listing.
02Your own pool
A private pool — the feature Florida buyers ask for first, already in the ground and included in the price.
03The price has already moved
Listed at $650,000, now $590,000 — a $60K cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of META ONE REALTY GROUP LLC · Aline Oliveira. MLS #S5149974.
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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