HEAT/COOL SALT WATER POOL - 815 LAKE JESSIE DR, WINTER HAVEN
Single Family Residence at 815 LAKE JESSIE DR, WINTER HAVEN, photo 2 of 30
HEAT/COOL SALT WATER POOL - 815 LAKE JESSIE DR, WINTER HAVEN
LAKE JESSIE - CHAIN OF LAKES - 815 LAKE JESSIE DR, WINTER HAVEN
Single Family Residence at 815 LAKE JESSIE DR, WINTER HAVEN, photo 5 of 30
VIRTUALLY STAGED - MAIN HOUSE ENTRANCE - 815 LAKE JESSIE DR, WINTER HAVEN
VIRTUALLY STAGED - MAIN HOUSE LIVING/WOOD FIREPLACE ROOM - 815 LAKE JESSIE DR, WINTER HAVEN
VIRTUALLY STAGED - MAIN HOUSE LIVING/WOOD FIREPLACE ROOM - 815 LAKE JESSIE DR, WINTER HAVEN
VIRTUALLY STAGED - MAIN HOUSE - 815 LAKE JESSIE DR, WINTER HAVEN
CASITA - LEFT SIDE - 815 LAKE JESSIE DR, WINTER HAVEN
HOUSE 2 - 815 LAKE JESSIE DR, WINTER HAVEN
MAIN HOUSE - 815 LAKE JESSIE DR, WINTER HAVEN
BATHROOM MAIN HOUSE - 815 LAKE JESSIE DR, WINTER HAVEN
KITCHEN 1 - 815 LAKE JESSIE DR, WINTER HAVEN
VIRTUALLY STAGED - HOUSE 2 LIVING ROOM - 815 LAKE JESSIE DR, WINTER HAVEN
VIRTUALLY STAGED - KITCHEN 2 - 815 LAKE JESSIE DR, WINTER HAVEN
VIRTUALLY STAGED - MASTER BEDROOM - 815 LAKE JESSIE DR, WINTER HAVEN
MASTER BATHROOM - 815 LAKE JESSIE DR, WINTER HAVEN
MASTER BATHROOM - 815 LAKE JESSIE DR, WINTER HAVEN
COVERED SCREENED FRONT PORCH - 815 LAKE JESSIE DR, WINTER HAVEN
COVERED SCREENED FRONT PORCH - 815 LAKE JESSIE DR, WINTER HAVEN
CORTYARD / COVERED PORCH - 815 LAKE JESSIE DR, WINTER HAVEN
CORTYARD / WORKSHOP / COVERED GARAGE - 815 LAKE JESSIE DR, WINTER HAVEN
BACKYARD - 815 LAKE JESSIE DR, WINTER HAVEN
VIRTUALLY STAGED - CASITA LIVING ROOM - 815 LAKE JESSIE DR, WINTER HAVEN
CASITA KITCHEN 3 - 815 LAKE JESSIE DR, WINTER HAVEN
VIRTUALLY STAGED - CASITA BEDROOM - 815 LAKE JESSIE DR, WINTER HAVEN
VIRTUALLY STAGED - POOL CABANA - 815 LAKE JESSIE DR, WINTER HAVEN
Single Family Residence at 815 LAKE JESSIE DR, WINTER HAVEN, photo 29 of 30
Single Family Residence at 815 LAKE JESSIE DR, WINTER HAVEN, photo 30 of 30
30 photos

$595,000

815 LAKE JESSIE DR
WINTER HAVEN, FL 33881
Listed by Aline Oliveira
Bedrooms
4
Bathrooms
4
Living area
4,128 sqft
Year built
1949

About this home

Virtually Staged. Mediterranean-Style Estate with Private Casita, Pool, Covered 2-Car Garage, Spacious Workshop & NO HOA in Winter Haven. Welcome to a truly unique Mediterranean-style estate offering over 4,100 square feet of living space, exceptional versatility, and the freedom of no HOA. This spacious property features a main residence plus a private casita, creating an ideal setup for multi-generational living, extended family, guests, a private home office, or flexible additional living space. Inside, you'll find generous living areas, beautiful architectural details, and plenty of room for both everyday living and entertaining. Recent improvements include a NEW ROOF and NEW AC, offering added peace of mind for the next owner. Step outside to your own private Florida retreat featuring a screened pool and spacious outdoor living areas, perfect for relaxing, entertaining, and enjoying Florida living year-round. The property also features a covered 2-car garage and an ample workshop, providing excellent space for vehicles, hobbies, projects, tools, storage, or recreational equipment. Need even more room for your toys? With no HOA and ample parking for boats, RVs, and recreational vehicles, this property offers the space, flexibility, and freedom that can be difficult to find. Conveniently located near Winter Haven's famous Chain of Lakes, you'll be close to boating, fishing, recreation, shopping, dining, and everything the area has to offer. Whether you're searching for a family estate, multi-generational home, private guest accommodations, a home with income potential, or simply a distinctive property with plenty of space and privacy, this home offers endless possibilities. Can't tour in person? Virtual tours are also available! Contact us today to schedule your private showing or virtual tour and experience everything this exceptional Winter Haven property has to offer.

Highlights

Private poolFireplace

Property details

MLS #
MFRS5158452
Property type
Single Family Residence
Subdivision
EAST VIEW PKWY
Status
Active
Days on market
1
On market date
September 28, 2026
Stories
N/A
Total bathrooms
4
Garage spaces
2
Parking spaces
N/A
Lot size
0.34 acres
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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card (e.g. NC Dept. of Public Instruction, SC Report Card).

Elementary
FRED G. GARNER ELEMENTARY SCHOOL
1.07 mi away · Grades -1-5
Nearest school -- attendance-zone data not available here
3.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
868
Student:teacher ratio
17.7:1
District
POLK
Middle
JERE L. STAMBAUGH MIDDLE
1.53 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
2.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
983
Student:teacher ratio
19.3:1
District
POLK
High
AUBURNDALE SENIOR HIGH SCHOOL
1.51 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
1.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
1,680
Student:teacher ratio
23.3:1
District
POLK

Walkability

Blended score for WINTER HAVEN's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

70
Walkable
out of 100
EPA National Walkability Index
11.2 / 20 -- Above average walkable
Google Places amenity density
90 / 100
Restaurants & cafes20
Grocery stores7
Parks1
Schools5
Transit stops20
Pharmacies4

Market position

How this listing compares to current activity in WINTER HAVEN, from live MLS data.

On the market 1 days -- 93 fewer days than WINTER HAVEN's current average of 94 days.
For reference, the median list price across 1,252 active listings in WINTER HAVEN right now is $245,000.

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

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Est. monthly payment
$3,733/mo
$119,000 down
$476,000 loan
Principal & interest$3,087
Property tax (est.)$496
Home insurance (est.)$150

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Data source: Listing information provided by Stellar MLS (mfrmls) via Trestle/CoreLogic. Last updated 2 days ago.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.