$881,000

1249 Osceola DR, Fort Myers, FL 33901

3 beds |
4 baths |
3,467 sqft

Single-Family Home
Built in 1924
0.29acre lot
2 car garage
$254/sqft
Listed 9 months ago

Property Description

Two houses for the price of one. Old homes are unique, full of charm and history. This historic home checks all the boxes, and one the best locations as well as close to downtown, schools, hospitals, kept mostly original to its original build, with updated electrical and plumbing, roof is only 3 years old. Never any flooding from any hurricanes in 22 years of ownership. In a neighborhood known for its close-knit neighbors, kid friendly sidewalks, pet friendly sidewalks, almost Norman Rockwell like neighborhood. With a multi-family designation, the super cute guest house has many possibilities or a rental? 3-bedroom main house, and a 1-bedroom guest house. Two car garage with plenty of room to store a boat or RV. Remember this is a 100-year-old home, antique homes are known for lack of closet space, kitchen is outdated as well, all bedrooms are upstairs. Tremendous possibilities or keep as is. If you like historic old homes, this is the one. Home is featured in Pam Miners book 'River & Road' Fort Myers Architecture from Craftsman to Modern. Chapter One. This is a unique home for that unique buyer. Location, location

Listing Status:: Active
Date Added:: October 24, 2025
Data Last Updated:: August 14, 2026 at 8:08PM
Listing Office:: Flatfee.com : (954) 965-3990
MLS ID:: 2025016791

General: Other
Appliances: DishwasherDryerMicrowaveRangeRefrigeratorWasher
Dining: Dining - Living
Laundry: In Garage
Flooring: Wood
A/C: Central Electric
Heating: Central Electric

General: Awning(s)
Style: Two StorySingle Family
Parking: DetachedParking spaces: 2

Roofing: Shingle
General: Concrete BlockWood FrameBrick2Concrete Block

Road/Access: Paved
HOA Amenities: 0.0
Originating MLS: Florida Gulf Coast
County: Lee

Zoning: RS-5RIVERSIDE BLK C PB 3 PG 63 LOT 1726-44-24-P4-0290C.0170
View: View
Fencing: Fenced
Restrictions: None

Water: Central

Source: Florida Gulf Coast

This listing courtesy of Flatfee.com

Monthly Payment

$Est. Payment

Principal & Interest $
Property Taxes $
Home Insurance $
VA Funding Fee $

Ready to Start a VA Loan?

Get Started

NMLS #1907 ^†

Get Prequalified »

Interest rates used in the VA mortgage calculator are shown for illustrative purposes only. Your rate may differ based on a variety of factors, including your credit score and the current market conditions. To get your personalized interest rate, start your quote online.