USAFLWinter HavenEast View Pkwy815 Lake Jessie Dr

815 Lake Jessie Dr, Winter Haven, FL

House

For Sale

Listed price in listed location currency (USD).

$650,000

442

MLS® S5149974

Key Facts
Description
Rooms
Map

Key Facts

Type Single Family Residence

Levels Residential

Size 4128 sqft

Garage Yes

Taxes $7,136

Days Active 0

Lot Size

Approx. Age 1949

Avg. Price Per Sqft $157

MLS® Number S5149974

Property Address: 815 Lake Jessie Dr, Winter Haven, FL, 33881-1151

Average square foot calculated using Size range provided by listing agent.

Description

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.

MLS® NumberS5149974

Laundry LevelEnsuite

Central VacNo

FireplaceYes

Acreage

Exterior

GarageYes

Approx. Age1949

Basement

DrivewayDriveway, Off Street, Open, Workshop in Garage

Garage Spaces

Heat

A/C

Heating Fuel

Extras

Price History

-End Date

Not Sold YetSold Price

For Sale

May 15, 2026List Date

$650,000List Price

Commute

Commute

Starting Address

Destination Address

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