815 LAKE JESSIE DRIVE Winter Haven, FL $ 650,000
815 LAKE JESSIE DRIVE
$ 650,000
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815 LAKE JESSIE DRIVE

Winter Haven, FL, 33881
$ 650,000
Bedrooms4 Baths4.0 Sq 4,128

Monthly Estimate*

$ 4,002

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Single Family Home for sale in Winter Haven, FL

for $650,000 with 4 bedrooms and 4 full baths. This 4,128 square foot home was built in 1949 on a lot size of 0.34.

Discover a truly one-of-a-kind Spanish/Mediterranean-inspired estate situated on an oversized lot across from beautiful Lake Jessie on the Chain of Lakes. Showcasing striking stucco architecture, elegant arched entryways, charming courtyard-style details, and mature tropical landscaping, this exceptional property offers endless possibilities for multi-generational living, short-term rental income, or long-term investment opportunities. Offering approximately 4,128 sq. ft. of living space, the property features a spacious 3-bedroom, 2-bath main residence (2,928 sq. ft.) and an attached private in-law suite/casita (1,200 sq. ft.) with 1 bedroom and 2 baths, connected by a 2-car garage with an additional workshop/man cave/storage area. The versatile floor plan provides the flexibility to function as a triplex-style investment property, vacation rental, or owner-occupied income-producing residence. Inside, the main home offers warm and inviting living spaces with vaulted ceilings, a fireplace, laminate flooring, abundant natural light, charming window seating, and extensive storage throughout. The family/sitting room flows seamlessly into a raised bonus/dining area, creating an ideal layout for entertaining. A spacious Florida room overlooks the resort-style screened pool area, while the oversized primary suite features private access to a screened porch, perfect for relaxing and enjoying the peaceful surroundings. Step outside to enjoy the beautifully updated saltwater heated pool featuring a new saltwater system, pool heater, and pool cooling system capable of heating the water up to 104 degrees for year-round enjoyment. Additional recent upgrades include a NEW roof on the main house, NEW AC, NEW water heater, NEW flooring in the casita, and much more. Located on a quiet street with no rear residential neighbors, this property offers exceptional privacy and tranquility while remaining just steps from the public/community boat ramp on Lake Jessie. With NO HOA, there is ample space to park your boat, RV, or additional vehicles. Whether you are searching for a unique waterfront-area retreat, a multi-generational estate, or an outstanding income-producing investment opportunity, this remarkable property is truly a rare find. Schedule your private showing today.

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Single Family Active

Price

$ 650,000

Bedrooms

4

Full Bath

4

Property Type

Single Family

Taxes

$ 7,136

Style

Mediterranean

Lot Size

0.34

Year Built

1949

Town/City

Winter Haven

County/Region

Polk

MLS | Web ID

S5149974

Features
General
Sewer Septic Tank
Heating Central
Cooling Central Air
Utilities Cable Available Electricity Connected Public
Roof Metal Other
Appliances Dishwasher Microwave Range Refrigerator
Zoning RM
Garage Spaces 2
Patio/Porch Features Covered Enclosed Front Porch Patio Screened Side Porch
Architectural Style Mediterranean
Pool Features Heated In Ground Salt Water
Security Features Smoke Detector(s)
Construction Materials Stucco
Pets Allowed Yes
Year Built 1949
View Water
Levels One
Property Subtype Single Family Residence
Tax Year 2025
Ownership Fee Simple
Accessibility Accessible Doors Accessible Entrance Visitor Bathroom
Additional Parcels Description 25-28-12-339500-000121
County Polk
New Construction false
Property Type Residential
Attached Garage false
Subdivision Name EAST VIEW PKWY
Facing Direction East
Garage Y/N true
Other Structures Other Shed(s)
Total Rooms 8
Full Baths 4
Status Active
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.
High School Auburndale High School
City WINTER HAVEN
Body of Water LAKE JESSIE
Senior Community Y/N false
MLS Area 33881 - Winter Haven / Florence Villa
Lot Size Units Square Feet
Lot Size Square Feet 15011
Carport Spaces 0
Carport Y/N false
Listing Terms Cash Conventional FHA VA Loan
Elementary School Auburndale Central Elem
Land Lease Y/N false
Tax Annual Amount 7136
Home Warranty Y/N false
Middle/Junior High School Westwood Middle
Property Condition Completed
Additional Parcels Y/N true
Lease Considered Y/N true
Virtual Tour https://www.propertypanorama.com/instaview/stellar/S5149974
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Active
Occupancy Type Vacant
Tax Lot 34
Legal Description EAST VIEW PARKWAY PB 13 PG 4 LOTS 34 & 35
Water View Lake Lake - Chain of Lakes
Water Access Type Lake
Minimum Lease No Minimum
Water Access Y/N true
Water View Y/N true
Flood Zone Code X
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Interior
Interior Amenities 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
Flooring Laminate Tile Hardwood
Furnished Y/N Negotiable
Fireplace Features Wood Burning
Air Conditioning Y/N true
Heating Y/N true
Fireplace Y/N true
Half Baths 0
Laundry Features Inside
Total Bedrooms 4
Total Baths 4
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Exterior
Exterior Amenities Irrigation System Other Rain Gutters Sliding Doors Storage
Fencing Fenced
Parking Features Driveway Off Street Open Workshop in Garage
Lot Features In County Oversized Lot Sidewalk
Water Source Public
Lot Size Area 15011
Foundation Details Crawlspace
Spa false
Building Area Total 4587
Lot Size Acres 0.34
Road Surface Type Paved Asphalt
Private Pool true
Waterfront Y/N false
Covered Spaces 2
Road Frontage Type Street Paved
Number of Lots 2
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* Excluded Features
List By
Meta One Realty Group Llc

Broker

alineoliveirarealtor@gmail.com

Email

Affordability Calculator

$4,597
Per Month
87%
13%
0%
Monthly Principal & Interest
$4,002
Monthly Property Taxes
$595
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
0 Elementary School
0 Middle School
Auburndale High School High School High School
Pricing History
DatePricePrice ChangeDescription
5/15/2026$650,000 Listed Price

Map


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815 LAKE JESSIE DRIVE, Winter Haven, FL, 33881 is a Single Family Home for sale at $650,000 with 4,128 sqft and a lot size of 0.34. 815 LAKE JESSIE DRIVE has 4 bedrooms, 4.0 baths, and was built in 1949. The property's zip code is 33881 which is in Winter Haven, FL