Waterfront - Fixer Upper
Address
5251 Lake Jessamine Drive, ORLANDO, FL
Price
$ 500,000
Property Attributes
- MLS#O6433370
- TypeSingle Family
- Listing Status Pending
- CountyOrange
- CityORLANDO
- AreaOrlando/Edgewood/Pinecastle
- NeighborhoodLAKE JESSAMINE SHORES
- Zip32839
- StyleSingle Family Residence
- Year Built1960
- Taxes$ 2309
- Price$ 500,000
- Bedrooms3
- Full Bathrooms2
- Half Bathrooms0
- Sqr Footage2502
- Lot Size1.09 Acres
Data Source:
Stellar MLS
Property Description
Under contract-accepting backup offers. 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.
| Price History | |
|---|---|
| 8/13/2026 | Listed $500,000 |
General Features
| Sewer | Septic Tank |
|---|---|
| Heating | Central,Electric |
| Cooling | Central Air |
| Utilities | Electricity Connected,Water Connected |
| Possession | Close Of Escrow |
| Roof | Shingle |
| Appliances | Dishwasher,Dryer,Microwave,Range,Range Hood,Refrigerator,Washer |
| Zoning | R-1AA |
| Garage Spaces | 2 |
| Construction Materials | Block,Other,Stone,Wood Frame,Wood Siding |
| Year Built | 1960 |
| View | Park/Greenbelt,Trees/Woods,Water |
| Levels | Multi/Split |
| Property Subtype | Single Family Residence |
| Tax Year | 2025 |
| Ownership | Fee Simple |
| Waterfront Features | Lake Front |
| County | Orange |
| New Construction | false |
| Property Type | Residential |
| Attached Garage | true |
| Subdivision Name | LAKE JESSAMINE SHORES |
| Facing Direction | West |
| Garage Y/N | true |
| Other Structures | Boat House,Storage |
| Total Rooms | 3 |
| Full Baths | 2 |
| Status | Pending |
| Directions | FROM I-4, TAKE EXIT 80 TOWARD ORANGE BLOSSOM TRAIL ONTO S ORANGE BLOSSOM TRAIL, DO A UTURN TO TAKE A RIGHT ONTO WOODSMERE AVE., LEFT ONTO LAKE JESSAMINE DR., HOME AT THE END. |
| City | ORLANDO |
| Body of Water | LAKE JESSAMINE |
| Senior Community Y/N | false |
| MLS Area | 32839 - Orlando/Edgewood/Pinecastle |
| Lot Size Units | Acres |
| Lot Size Square Feet | 47664 |
| Carport Y/N | false |
| Listing Terms | Cash,Conventional |
| Land Lease Y/N | false |
| Tax Annual Amount | 2309 |
| Property Condition | Fixer |
| Additional Parcels Y/N | false |
| Lease Considered Y/N | true |
| Building Area Units | Square Feet |
| Living Area Units | Square Feet |
| Standard Status | Active Under Contract |
| Occupancy Type | Vacant |
| Tax Lot | 1 |
| 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 |
| Water View | Lake |
| Minimum Lease | No Minimum |
| Water Access Y/N | false |
| Additional Rooms | Inside Utility |
| Water View Y/N | true |
| Flood Zone Code | X |
| In Law Suite YN | false |
| Flood Zone Code X | Yes |
| DockY/N | true |
Interior Features
| Interior Amenities | Ceiling Fan(s) |
|---|---|
| Flooring | Carpet,Other,Tile |
| Furnished Y/N | Partially |
| Air Conditioning Y/N | true |
| Heating Y/N | true |
| Fireplace Y/N | false |
| Laundry Features | Inside,Laundry Room |
| Total Bedrooms | 3 |
| LivingAreaSource | Public Records |
| Total Baths | 2 |
Exterior Features
| Exterior Amenities | Storage |
|---|---|
| Vegetation | Mature Landscaping |
| Parking Features | Boat,Driveway,Garage Door Opener |
| Lot Features | Oversized Lot,Street Dead-End |
| Water Source | Public |
| Lot Size Area | 1.0942 |
| Foundation Details | Other,Slab |
| Building Area Total | 3244 |
| Lot Size Acres | 1.09 |
| Road Surface Type | Paved |
| Private Pool | false |
| Waterfront Y/N | true |
| Covered Spaces | 2 |
| Road Frontage Type | Street Dead-End,Street Paved |
Amenities
- Foreclosure
- Views
- Short Sale
- New Construction
- Adult 55+
- Lease To Own
- No HOA Fees
- Furnished
- Primary On Main
- Air Conditioning
- Seller Finance
- Green
- Fixer Upper
- Horse
- Golf
- Fireplace
- Deck
- Garage
- Basement
- Pool
Property vs Single Family Average in 32839
Price
Taxes
Year Built
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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.
Updated on September 19, 2026 11:48 AM UTC
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Data Last Updated: September 19, 2026 11:48 AM UTC
