815 LAKE JESSIE DRIVE, Winter Haven, FL 33881

  • $650,000

Overview

Property ID: HZS5149974
  • Single Family Residence, Residential
  • Property Type
  • 4
  • Bedrooms
  • 4
  • Bathrooms
  • 2
  • Garages
  • 4587 Sqft
  • Area Size

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.

  • Address: 815 LAKE JESSIE DRIVE
  • City: Winter Haven
  • State/county: FL
  • Zip/Postal Code: 33881
  • Country: US

Details

Updated on May 16, 2026 at 10:48 am
  • Property ID HZS5149974
  • Price $650,000
  • Property Size 4587 Sqft
  • Land Area 0.34 Acres
  • Bedrooms 4
  • Bathrooms 4
  • Garages 2
  • Garage Size x x
  • Year Built 1949
  • Property Type Single Family Residence, Residential
  • Property Status Active

Additional details

  • Listing Terms Cash,Conventional,FHA,VA Loan
  • Roof Metal,Other
  • Utilities Cable Available,Electricity Connected,Public
  • Sewer Septic Tank
  • Cooling Central Air
  • Heating Central
  • Flooring Laminate,Tile,Wood
  • County Polk
  • Property Type Residential
  • Pool Heated,In Ground,Salt Water
  • Parking Driveway,Off Street,Open,Workshop in Garage
  • Elementary School Auburndale Central Elem
  • Middle School Westwood Middle
  • High School Auburndale High School
  • Architectural Style Mediterranean

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