$849,000

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
$245/sqft
Listed 3 months ago

Property Description

Historic charm, built in 1924, A unique preserved historic home that is part of Fort Myers Florida history, ready for a new caretaker, owner is downsizing and found a new home, owner states "submit offers" they are ready to move, well maintained as close to original build as possible with upgraded plumbing and electrical. Never any flooding from any of the recent storms like hurricane Ian, zero flooding. They knew where to build in 1924. Complete new roof is two years old with transferable warranty. Many consider between Gasparilla and Caloosa Drive on the riverside of McGregor the best location in Fort Myers. Active community, kid friendly and pet friendly sidewalks and streets. This is a unique home for that unique buyer that appreciates old historic warmth and charm. Room for a pool or maybe a pickleball court, quest house is one of the cutest self-contained guest houses with all new plumbing. Guest house has one bedroom, living room, dining area and small kitchen with a bathroom. With a multi-family designation, can be legally rented. Main house and guest house, you are getting two beautiful historic homes for the price of one. Two car garage and room to store RV or boat. Preserving the historical charm is something that has been admired by many. All bedrooms are upstairs. Home is featured in Pam Miners book 'River & Road' Fort Myers Architecture from Craftsman to Modern. Chapter One. Location, location, location

Listing Status:: Active
Date Added:: October 24, 2025
Data Last Updated:: February 12, 2026 at 12:07PM
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-526-44-24-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 $

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Location

Schools Nearby

Allen Park Elementary School

3345 Canelo Dr, Fort Myers, FL, 33901

Grades KG-5

0.66 miles away

Fort Myers Middle Academy

3050 Central Ave, Fort Myers, FL, 33901

Grades 6-8

1.40 miles away

Fort Myers High School

2635 Cortez Blvd, Fort Myers, FL, 33901

Grades 9-12

0.98 miles away

Disclaimer: School and School District information courtesy of the National Center for Education Statistics (NCES). School boundaries may change. Proximity to listed schools does not guarantee enrollment eligibility. Contact the school district for more information and exact boundaries.