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$500,000

5251 Lake Jessamine Drive

Orlando, FL 32839

Listing updated: October 1, 2026 at 4:10 PM ET

Active

Listing courtesy of Blue Marlin Real Estate · Dana Vander Meer · MLS #O6433370 · Active · 321-877-2902

Beds

Baths

2,502

Sq Ft

1.09

Acres

1960

Built

◆Waterfront◆1.09 acres◆$200/sqft

Single Family Residence

Property type

1960

Year built

47,664 sqft

Lot size

$200

Price / sq ft

No HOA

HOA dues

Days on market

Garage spaces

Flood zone

About this home

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.

Estimated monthly payment

Principal & interest$2,528

Property taxes$192

Home insurance (est.)$229

Down payment

20%

$100,000 downRate

6.5%

Term

Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.

Price & listing history12 days on market

Status: Active
Oct 1, 2026
Listed$500,000
Aug 13, 2026
Price increased$500,000

Facts & features

Property type: Residential
Sub type: Single Family Residence
Status: Active
Days on market: 12
Subdivision: Lake Jessamine Shores
County: Orange
Year built: 1960
Living area: 2,502 sq ft
Price/sq ft: $200
Building area: 3,244 sq ft (Public Records)
Lot size: 47,664 sq ft
Lot category: 1 to less than 2
Flood zone: X (12095C0410F)
Garage: 2 spaces
Annual taxes: $2,309 (2025)
Parcel #: 14-23-29-0000-00-037
Zoning: R-1AA
MLS #: O6433370

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Interior Details

Bedrooms: 3
Full bathrooms: 2
Flooring: Carpet, Other, Tile
Appliances: Dishwasher, Dryer, Microwave, Range, Range Hood, Refrigerator, Washer
Interior features: Ceiling Fans(s)
Laundry: Inside, Laundry Room
Stories / Levels: Multi/Split
Direction faces: West

Heating & Cooling

Heating: Central, Electric
Cooling: Central Air

Parking

Garage spaces: 2
Attached garage: Yes
Parking features: Boat, Driveway, Garage Door Opener

HOA & Financial

Total monthly fees: $0/mo
Total annual fees: $0
CDD: No
Homestead exemption: Yes
Min lease term: No Minimum
Listing terms: Cash, Conventional
Ownership: Fee Simple
Available for lease: Yes
Lease restrictions: No
Additional lease restrictions: VERIFY ANY LEASE/RENTAL RESTRICTIONS WITH ORANGE COUNTY, FL.

Exterior & Construction

Exterior features: Storage
Construction materials: Block, Other, Stone, Frame, Wood Siding
Roof: Shingle
Foundation: Other, Slab
Waterfront: Yes
Water view: Yes
Road surface: Paved

Utilities

Sewer: Septic Tank
Water source: Public
Utilities: Electricity Connected, Water Connected

Room Details

Room	Level	Dimensions
Living Room	First	26x24
Kitchen	Second	11x13
Primary Bedroom	Second	13x13

Listing Details

Listing date: 2026-08-10
On market date: 2026-08-13
Original list price: $500,000
Occupant type: Vacant
MLS area: 32839 - Orlando/Edgewood/Pinecastle
Listing AOR: Orlando Regional
Status changed: 2026-10-01
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

Flood risk

Minimal riskFEMA Zone XPanel 12095C0410F

Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.

Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.

Location

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.

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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.

Based on information submitted to the MLS GRID as of October 1, 2026 at 4:10 PM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information 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/agent presenting the information.

All or a portion of the multiple listing information is provided by Stellar MLS, from a copyrighted compilation of listings. The compilation of listings and each individual listing are © 2026 Stellar MLS. All rights reserved.

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