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815 Lake Jessie Drive, Winter Haven, FL 33881

$650,000
  • 815 Lake Jessie Drive, Winter Haven, FL 33881 Main Photo

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New to the Market Active
BEDS4 BATHS4 full SQUARE FEET4,128 MLS#S5149974
STATUSActive PROPERTY TYPEResidential - Single Family SUBDIVISIONEAST VIEW PKWY

Property 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.

815 Lake Jessie Drive | MLS# S5149974

This single family home located at 815 Lake Jessie Drive, Winter Haven, FL 33881 is currently listed for sale with an asking price of $650,000. This property was built in 1949 and has 4 bedrooms and 4 full baths with 4128 sq. ft. Lake Jessie Drive is located in the EAST VIEW PKWY subdivision. Search EAST VIEW PKWY real estate on andersonbarbosa.realty100.com today.

Property Features

Property Type: Residential - Single Family
Cooling: Central Air
Fenced: Yes
Garage: 2
Heating: Central
Home Style: Mediterranean
Lot Size: 0.34 Acres
Roof Type: Metal, Other
Stories: 1.0
Taxes: $7,136
Year Built: 1949

Amenities

Cathedral Ceiling(s)
Ceiling Fans(s)
Eat-in Kitchen
High Ceilings
Open Floorplan
Primary Bedroom Main Floor
Split Bedroom
Vaulted Ceiling(s)
Walk-In Closet(s)
Window Treatments
Other
Rain Gutters
Sliding Doors
Storage

Feature Descriptions

Accessibility Features: Accessible Doors, Accessible Entrance, Visitor Bathroom
Appliances: Dishwasher, Microwave, Range, Refrigerator
Body of Water: LAKE JESSIE
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.
Exterior: Stucco
Fencing: Fenced
Fireplace: Wood Burning
Fireplace Y/N: Yes
Flood Zone Code: X
Flooring: Laminate, Tile, Wood
Foundation: Crawlspace
Garage Dimensions: 20X30
Home Warranty Y/N: No
Listing Terms: Cash, Conventional, FHA, VA Loan
Lot: In County, Oversized Lot, Sidewalk, Paved
Lot Dimensions: 0.34
Other Equipment: Irrigation Equipment
Other Structures: Other, Shed(s)
Ownership: Fee Simple
Parking: Driveway, Off Street, Open, Workshop in Garage
Parking Notes: Driveway, Off Street, Open, Workshop in Garage
Patio/Porch: Covered, Enclosed, Front Porch, Patio, Screened, Side Porch
Pets Allowed: Yes
Pets Restrictions: No restrictions
Pool: Heated, In Ground, Salt Water
Property Attached Y/N: No
Property Sub-Type: Single Family Residence
Security: Smoke Detector(s)
Sewer: Septic Tank
Showing Instructions: Combination Lock Box
Special Sale Provisions: None
Special View Info: Water
Swimming Pool: Yes
Utilities: Cable Available, Electricity Connected, Public
Water: Public
Water Access: Lake
Water Access Y/N: Yes
Water View: Lake, Lake - Chain of Lakes
Zoning: RM

Room Sizes

Living Room: 20x11
Family Room: 33.5x12
Primary Bedroom: 19x13
Bedroom 2: 14x12
Bedroom 3: 12x10
Bedroom 4: 19x15
Kitchen: 11x10
Dining Room: 14x11

Local Schools

High School: Auburndale High School
Middle School: Westwood Middle
Elementary School: Auburndale Central Elem

Listed By / Shown By

Listed By

Agency Name: META ONE REALTY GROUP LLC
Agency Contact: 407-223-3678

Shown By

Agent Name: Anderson Barbosa
Agent Phone: Cell: (954) 621-7273
Agency Title: Realty 100

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Estimated Payment

$ 2,230.87 per month $1,446.62 Principal & Interest $594.67 Property Tax $189.58 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided 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. Information on this site was last updated 05/16/2026. The listing information on this page last changed on 05/16/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Sat 05/16/2026 3:37:08 AM EST) or Miami MLS (last updated Sat 05/16/2026 12:28:58 AM EST) or Stellar MLS (last updated Sat 05/16/2026 1:59:17 AM EST) or Beaches MLS (last updated Sat 05/16/2026 2:39:04 AM EST). Real estate listings held by brokerage firms other than Realty 100 may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

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