
900 LAKE JESSIE DRIVE, WINTER HAVEN, FL, 33881
Active130 days on marketListed Mar 28, 2026MLS #S5146723
About this home
900 LAKE JESSIE DRIVE
One or more photo(s) has been virtually staged. Welcome to a place where everyday life feels like a getaway. Set along the peaceful shores of Lake Jessie, part of Winter Haven’s renowned Chain of Lakes, this lakefront retreat is more than just a home, it’s a lifestyle defined by water, sunshine, & unforgettable experiences. Start your mornings with breathtaking sunrises shimmering across the lake, coffee in hand from your private dock or patio. Spend your days exactly how you choose, cruising the Chain of Lakes by boat, casting a line in some of Central Florida’s best freshwater fishing, or enjoying world-class watersports like skiing, wakeboarding and paddleboarding right from your backyard. With nearby slalom courses & open water, this is truly a paradise for water enthusiasts. Lake Jessie is especially cherished for its tranquil atmosphere, offering a rare sense of calm while still being full of life. One of its most unique features is the seaplane activity, where you can watch planes gracefully land and take off across the water, an experience that never gets old and adds to the charm of lakeside living. Nature lovers will also appreciate the frequent sightings of all kinds of birds & other beautiful wildlife. The home itself offers a thoughtfully designed single-story layout with over 1,800 square feet, featuring 3 bedrooms & 3 bathrooms. An open-concept living space is filled with natural light and showcases stunning lake views, while a split-bedroom design provides comfort & privacy. A private in-law suite with its own entrance adds flexibility for guests, multi-generational living, or additional income potential. This residence offers plenty of parking space with its oversized driveway & an additional carport providing covered parking as well. The home has been updated with modern finishes and includes a metal roof installed in 2019. This home would make a perfect full time residence, investment property or second home. Beyond the water, the location is just as appealing. You’re right around the corner from a brand new Publix store and minutes from the heart of Winter Haven, where you’ll find charming local restaurants, shops, parks, and community events. Legoland Florida Resort is just a short drive away and there is convenient access to both Tampa and Orlando, so world-class attractions, dining & entertainment are always within reach. Whether you're seeking adventure, relaxation, or a smart investment, this Lake Jessie property delivers it all, offering the rare opportunity to live, play & unwind in one of Florida’s most iconic lakefront settings. Book your showing today!
Facts & features
The home at a glance
3
Bedrooms
3
Bathrooms
1,828
Sqft
0.38 ac
Lot size
1948
Year built
One
Levels
$232
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.
$3,185 /mo · 3.5% down FHA, 30-yr fixed at 6%
The assumptions
FHA is the default here because it gets you in the door with just 3.5% down. Switch to Conventional or VA below.
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
Estimated payment
$3,185/mo
Includes FHA mortgage insurance and the financed 1.75% upfront premium. 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
+42.7%
$/sqft vs Winter Haven actives
$232 vs $170
Days on market
130 vs 47 typical
Where $232/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 75% 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 900 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 · Feb ’26$260,000
1663 W LAKE CANNON DRIVE NW
2 bd · 2 ba · 1,850 sqft · $141/sqft · 351 DOM
Sold · Dec ’25$265,000
2634 TRINITY CIRCLE NW
3 bd · 2 ba · 1,859 sqft · $143/sqft · 99 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 900 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 900 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
900 LAKE JESSIE DRIVE FAQs
What would the monthly payment be for 900 LAKE JESSIE DRIVE?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $3,185/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 900 LAKE JESSIE DRIVE?+
The most recent tax bill on record (2025) was $4,023. 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 900 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 $425,000, this home is listed about 49% above the Winter Haven median of $284,990. The market section on this page shows how the area is trending.
Which schools are assigned to 900 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
Four things that matter here
01Positioned at the premium end
$425,000 runs 75% above the WINTER HAVEN 33881 median.
02Waterfront living
This home sits directly on the water — the single scarcest feature in Florida inventory and the strongest long-term value anchor.
03Time on market is leverage
130 days on market against a Winter Haven median of 47 — sellers in this position are usually ready to negotiate.
04The price has already moved
Listed at $469,900, now $425,000 — a $45K cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of RE/MAX HERITAGE PROFESSIONALS · Patricia De Graaff, Llc. MLS #S5146723.
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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