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$615,000
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Property Description
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!
Full Property Details
Full Property Details for 815 Lake Jessie Dr
General
- Price: $615,000
- Taxes: $7,136 (2025)
- Status: Active
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: S5149974
- Updated: 6/24/2026
- Added to Site: 51 day(s) ago
Rental Information
- Min. Lease: No Minimum
Interior
- Number of Rooms: 8
- Interior Features: Cathedral Ceiling(s), Ceiling Fan(s), Eating Space In Kitchen, High Ceilings, Open Floorplan, Primary Bedroom Main Floor, Split Bedroom, Vaulted Ceiling(s), Walk-In Closet(s), Window Treatments
- Fireplace: Yes
- Fireplace(s): Wood Burning
- Appliances: Dishwasher, Microwave, Range, Refrigerator
- Furnishings: Negotiable
- Flooring: Laminate, Tile, Hardwood
Rooms
Bathrooms
- Total Bathrooms: 4
- Full Bathrooms: 4
Bedrooms
- Total Bedrooms: 4
Other Rooms
- Laundry: Inside
Additional Information
- Pool: Yes
- Private Pool: Yes
- Pool Description: Heated, In Ground, Salt Water
- Security/Safety: Smoke Detector(s)
Exterior
- Exterior Features: Irrigation System, Other, Rain Gutters, Sliding Doors, Storage
- Deck/Patio: Covered, Enclosed, Front Porch, Patio, Screened, Side Porch
- Porch/Patio/Deck: Covered, Enclosed, Front Porch, Patio, Screened, Side P
Parking
- Garage: Yes
- Garage Spaces: 2
- Covered Spaces: 2
- Parking Features: Driveway, Off Street, Open, Workshop in Garage
Location
- Area: 33881 - Winter Haven / Florence Villa
- County: Polk
- Development Name: 33881 - Winter Haven / Florence Villa
- Subdivision: EAST VIEW PKWY
- Driving Directions: From 1st Street North, left on Hwy 544/Havendale Blvd., turn right onto Jersey Road, right onto E. Derby Avenue, left onto Lake Jessie Drive, property will be on your left.
- Direction Faces: East
School Information
- Elementary School: Auburndale Central Elem
- Middle School: Westwood Middle
- High School: Auburndale High School
Community
- Community Name: 33881 - Winter Haven / Florence Villa
- Pet Restrictions: No restrictions
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Central
Utilities
- Sewer: Septic Tank
- Water District: LAKE JESSIE
- Water: Public
- Utility Description: Cable TV Available, Electricity Connected, Public
Structural Information
- Architectural Info: Mediterranean
- Architectural Style: Mediterranean
- Exterior Const.: Stucco
- Roof: Metal, Other
- Stories/Levels: One
- Square Feet: 4,128
- Sq. Ft. Source: Estimated
- Year Built: 1949
Additional Structures
- Other Structures: Other, Shed(s)
Lot Features
- Property View: Water
- Lot Size (Acres): 0.34
- Lot Size (Sq. Ft.): 15,011
- Lot Size: 15011
- Frontage: Street Paved
- Street/Road Desc.: Paved, Asphalt
- Fencing (Description): Fenced
Water Features
- Water View: Yes
- Water Access: Yes
- Water Access Desc: Lake
- Water Front Name: LAKE JESSIE
Financial Considerations
- Tax Amount: $7,136
- Tax Year: 2025
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: EAST VIEW PARKWAY PB 13 PG 4 LOTS 34 & 35
- Flood Zone Info: X
- APN: 252812338500000340
- Property ID: 252812338500000340
Listed by Meta One Realty Group Llc
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Schools
Schools serving 815 Lake Jessie Dr
School District:Polk County School District
| Name | Grades | Distance |
|---|---|---|
Auburndale Central Elementary School 320 Lemon Street, Auburndale, FL 33823 | PK-5 | 1.2 mi |
Auburndale Senior High School 1 Bloodhound Trail, Auburndale, FL 33823 | 9-12 | 1.5 mi |
Westwood Middle School, Winter Haven, FL 3520 Avenue J Northwest, Winter Haven, FL 33881 | 6-8 | 1.8 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 815 Lake Jessie Dr
Date
Details
Price
Change
Source
6/24/2026
Price Reduced
$615,000
-0.81%
MLS
6/12/2026
Price Reduced
$620,000
-4.62%
MLS
5/15/2026
Listed
$650,000
44.44%
MLS
1/25/2022
Sold
$450,000
—
Public Record
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Tax History
Tax History for 815 Lake Jessie Dr
Year
Property Taxes
Change
Tax Assessment
Change
2025
$98
-11%
$4,006
-63%
2024
$110
45%
$10,964
231%
2023
$76
58%
$3,311
29%
2021
$48
-19%
$2,559
-8%
2022
$59
23%
$2,784
16%
2021
$48
—
$2,408
—
2019
$48
2%
$2,408
3%
2017
$47
—
$2,333
11%
2017
$47
7%
$2,107
—
2016
$44
-2%
$2,107
5%
2015
$45
7%
$2,004
10%
2014
$42
5%
$1,822
10%
2013
$40
—
$1,656
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 815 Lake Jessie Dr
815 Lake Jessie Drive, Winter Haven, FL 33881 (MLS# S5149974) is a Single Family property with 4 bedrooms and 4 full bathrooms. 815 Lake Jessie Drive is currently listed for $615,000 and was received on May 15, 2026. Want to learn more about 815 Lake Jessie Drive? Do you have questions about finding other Single Family real estate for sale in Winter Haven? You can browse all Winter Haven real estate or contact a Coldwell Banker agent to request more information.

