815 LAKE JESSIE DRIVE WINTER HAVEN, FL 33881

update time: 09/29/2026 10:50:19

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.

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.

Property Details

Nearby Properties

Single Family Residence Active

2608 TRINITY CIRCLE NW WINTER HAVEN, FL 33881

2 Beds0/2Baths1,608sqft1968 built

$239,900.00

Townhouse Active

7046 TOWNE LAKE ROAD RIVERVIEW, FL 33578

3 Beds1/2Baths1,400sqft2016 built

$259,999.00

Single Family Residence Active

900 LAKE JESSIE DRIVE WINTER HAVEN, FL 33881

3 Beds0/3Baths1,828sqft1948 built

$410,000.00

Single Family Residence Active

4669 OSPREY WAY WINTER HAVEN, FL 33881

4 Beds0/2Baths2,660sqft2019 built

$309,000.00

Condominium Active

12760 INDIAN ROCKS ROAD UNIT 119 LARGO, FL 33774

2 Beds0/2Baths1,304sqft1972 built

$160,000.00

Single Family Residence Active

3220 FISH HAWK DRIVE POLK CITY, FL 33868

1 Beds0/1Baths2,072sqft2019 built

$399,000.00

Single Family Residence Active

5060 STARLING DRIVE MULBERRY, FL 33860

3 Beds0/2Baths2,035sqft1975 built

$299,000.00

Condominium Active

3101 BAYSHORE BOULEVARD UNIT 2501 TAMPA, FL 33629

4 Beds1/5Baths6,739sqft2024 built

$6,499,000.00

Manufactured Home Active

212 KAYLOR DRIVE AUBURNDALE, FL 33823

2 Beds0/1Baths672sqft1986 built

$269,000.00

1/2 Duplex Active

451 CAMEO DRIVE LAKELAND, FL 33803

2 Beds0/2Baths1,890sqft1975 built

$169,900.00

Single Family Residence Active

2390 29TH STREET NW WINTER HAVEN, FL 33881

4 Beds0/2Baths1,048sqft1965 built

$209,900.00

Single Family Residence Active

3022 HICKORY STREET NW WINTER HAVEN, FL 33881

3 Beds0/1Baths1,652sqft1955 built

$265,000.00

Single Family Residence Active

803 LAKE JESSIE DR DRIVE WINTER HAVEN, FL 33881

4 Beds0/4Baths4,262sqft2023 built

$624,900.00

Single Family Residence Active

4919 ST JAMES DRIVE WINTER HAVEN, FL 33881

3 Beds0/2Baths2,180sqft2010 built

$299,900.00

Townhouse Active

4533 HERON LODGE NEW PORT RICHEY, FL 34652

3 Beds0/3Baths2,510sqft2007 built

$500,000.00

Single Family Residence Active

1230 MOTORCOACH DRIVE POLK CITY, FL 33868

2 Beds0/2Baths2,853sqft2005 built

$479,000.00

Single Family Residence Active

31 MORGAN STREET AUBURNDALE, FL 33823

4 Beds0/2Baths2,462sqft2024 built

$680,000.00

Single Family Residence Active

4750 OSPREY WAY WINTER HAVEN, FL 33881

4 Beds0/2Baths2,660sqft2017 built

$305,000.00

Single Family Residence Active

2129 W TOBAGO CIRCLE FORT MYERS, FL 33905

3 Beds0/2Baths4,671sqft1973 built

$1,499,000.00

Single Family Residence Active

6745 ENGLELAKE DRIVE LAKELAND, FL 33813

4 Beds1/2Baths2,934sqft1983 built

$430,000.00