$595,000
815 LAKE JESSIE DRIVE, WINTER HAVEN, FL 33881
Beds
4
Baths
4
Sq Ft
4,128 sq ft
Year Built
1949
Lot Size
0.34 acres
Garage
2
About This Property
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. Enjoy your own private outdoor oasis featuring a beautiful saltwater pool with a new heating and cooling system, complemented by a poolside cabana, perfect for relaxing and entertaining 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.
Property Overview
Interior Features
Exterior & Lot
Pool & Spa
Utilities
Parking
HOA & Community
Financial Details
Schools
Directions
rom 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.
Location
815 LAKE JESSIE DRIVE, WINTER HAVEN, FL 33881
Listing Information
Schedule a Tour
Pick a Day
Preferred Time
Home Price
$595,000
Loan Term
Nearby Schools
How to Buy This Home
Multiple financing options available for this $595,000 home in WINTER HAVEN.
🏛️
FHA Loan
$20,825 Down
Government-backed, low down payment. Credit scores as low as 580.
🎖️
VA Loan
$0 Down
Zero down for eligible veterans, active duty, and military families.
🏦
Conventional
$29,750 Down
Traditional financing. As low as 3-5% down with good credit.
Florida Down Payment Assistance Programs
You may qualify for up to $35,000 in assistance to cover your down payment and closing costs.
Florida Hometown Heroes
Up to $35,000
First-time buyers working in FL
FL Assist
Up to $10,000
FHA, VA, or USDA borrowers
FL HLP Second Mortgage
Up to $10,000
First-time buyers, 0% deferred
Polk County SHIP
Varies
Income-qualifying Polk residents
Can You Afford This Home?
Quick check based on the 28% debt-to-income rule. Not a guarantee — just a starting point.
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Listing information is deemed reliable but not guaranteed. All measurements and data should be independently verified. This information is provided by the Stellar MLS. The listing broker's offer of compensation is made only to participants of the MLS where the listing is filed. 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 last updated: October 1, 2026.