Home in 5251 Lake Jessamine Dr Orlando for sale with MLS# O6433370

FIXER-UPPER ON LAKE JESSAMINE with character, waterfront and plenty of potential! This Orlando home has the kind of personality that only comes with decades of history, from vintage finishes and retro details to terrazzo flooring waiting underneath portions of the existing flooring. This home is going to need work. There are known settling/structural concerns, along with repairs and updating needed throughout. The current condition may also present challenges for traditional financing and insurance, making this a property best suited for a buyer who understands the scope of a fixer-upper and is ready to take on a project. Inside, the home offers generous living spaces, multiple bedrooms and baths, a spacious kitchen, large laundry/utility area and an oversized garage with room for vehicles, storage, hobbies and projects. There is plenty of existing character to work with and plenty of opportunity to put your own stamp on it. Outside, the waterfront setting adds another layer to this unique property. The long lot extends from the canal to Lake Jessamine, offering both canal and direct lake frontage. At the lake, a private boathouse features two boat slips. And tucked beneath the house is something you don't see every day-an additional boat garage with direct canal access. A hatch in the laundry room opens to a ladder leading down to the boat area below, allowing access directly from the house to the canal when water levels permit. This property isn't polished or perfect, and it isn't pretending to be. It's a true fixer-upper with history, character, an unusual waterfront setup and a Lake Jessamine lot ready for someone with the vision to take on what comes next.

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5251 Lake Jessamine Dr, Orlando, FL 32839

Price
Price:
$500,000.00
Original List Price:
$500,000.00
List Price per Sq Ft (Calculated, Approx.):
$199.84
Property Status and Type
Listing Type:
For Sale
Status:
Active
Listing Category:
Residential
Property Type:
Single Family House
MLS Number:
O6433370
Rooms Distribution
Bedrooms:
3
Bathrooms Total:
2
Full Bath:
2
Additional Rooms:
Inside Utility
Measures
Living Area:
2,502 Sqft
Built-Up Area:
3,244 Sqft
Lot Area:
47,664 Sqft
Building Area Source:
Public Records
Living Area Source:
Public Records
Lot Features:
Oversized Lot, Paved, Street Dead-end
Lot Size Acres:
1.09
Property Features
View from the Property:
Water, Park/greenbelt, Trees/woods
Waterfront:
Yes
Waterfront Features:
Lake Front
Furnished:
Partially
Appliances:
Dryer, Dishwasher, Microwave, Refrigerator, Washer, Range, Range Hood
Interior:
Ceiling Fans(s)
Exterior:
Storage
Other Structures:
Storage, Boat House
Laundry:
Inside, Laundry Room
Air Conditioning System:
Central Air
Heating System:
Central, Electric
Vegetation and Trees:
Mature Landscaping
Property Entrance Faces:
West
Water Extras
Water Extra Details:
Boathouse, Lift - Covered
Water View
Water View Details:
Lake
Construction
Year Built:
1960
Roof:
Shingle
Levels:
Multi/Split
Construction Materials:
Block, Frame, Other, Wood Siding, Stone, Wood Siding
Flooring:
Carpet, Tile, Other
Foundation Details:
Slab, Other
Flood Zone Code:
X
Property Condition:
Fixer
Taxes and Expenses
Homestead Property
Tax Annual Amount:
$2,309.00
Tax Year:
2025
Parking
Garage
Garage Spaces:
2
Attached Garage
Parking Features:
Driveway, Garage Door Opener, Boat
Utilities
Sewer:
Septic Tank
Utilities Available:
Electricity Connected, Water Connected
Water Source:
Public
Community
Minimum Lease Term:
No Minimum
Subdivision Name:
LAKE JESSAMINE SHORES
Senior Community:
No
Terms
Listing Terms Considered by Seller:
Cash, Conventional
Occupant Type:
Vacant
Buyer Possession:
Close Of Escrow
Lease Considered:
Yes
Zoning and Legal
Tax Legal Description:
BEG NW COR OF LOT 1 BLK A LAKE JESSAMINESHORES R/41 RUN E 880 FT N 40 FT W 665FT NWLY 241.8 FT TO PT 150 FT N OF POB STO POB IN SEC 14-23-29
Real Estate Folio Number (Parcel Number):
14-23-29-0000-00-037
Zoning:
R-1AA
Title to the property is held by owner as:
Fee Simple
Listing History
Originally published on:
August 13, 2026 6:08 pm
Active on the market since:
August 13, 2026
Listing Agreement executed on:
August 10, 2026
Listing Status Last Changed On:
August 13, 2026 6:08 pm
Photos updated on:
August 13, 2026 7:45 pm
Last Modified:
August 14, 2026 10:48 am
Additional Information
Courtesy of:
BLUE MARLIN REAL ESTATE
Attribution:
321-877-2902
Road Surface Type:
Paved
Location
Street Name:
LAKE JESSAMINE
Street Number:
5251
City:
ORLANDO
State:
Florida
Zip Code:
32839
County:
Orange
Latitude:
N28° 29' 4.2''
Longitude:
W82° 36' 35.3''
Property Map

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Neighborhood Stats

Source: U.S. Census Bureau, ACS 5-Year Estimates

Median Household Income $50,814
Median Home Value $250,800
Median Rent $1,429/mo
Median Age 32
Population 51,807
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Association of REALTORS®
Disclaimer: IDX listing information is presented by Rebonus Brokerage LLC for consumer informational purposes only. Listings courtesy of Stellar MLS, as distributed by MLS GRID. IDX information is provided exclusively 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. All data is obtained from various sources and may not have been verified by the broker or MLS GRID. Supplied Open House information, if any, is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office or agent presenting the information. The data is deemed reliable but is not guaranteed by MLS GRID. Use of MLS GRID data may be subject to an end user license agreement prescribed by the applicable MLS and as amended from time to time. Some IDX listings have been excluded from this website. This page presents structured listing information sourced directly from the MLS via the RESO Web API feed. Rebonus prioritizes maximum field coverage and data completeness, displaying the most granular MLS-provided attributes available. Based on information submitted to MLS GRID as of August 14, 2026, 10:48 AM.