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About This Home

This 3-bedroom, 4-bathroom single family at 1249 Osceola Drive in Fort Myers, FL is listed for $831,000 ($240 per sqft). Built in 1924, the home offers 3,467 sqft of living space on a 0.29 acres lot.

Agent Description

New price, Location, Location, Location, 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 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 three years new. 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. Priced to sell

Key Features

  • Built in 1924
  • 0.29 acre lot
  • 2 stories

Property Details

2 stories
4 full
1924

Amenities

A/C

Monthly Cost Estimate

$4,444/mo

20% down · 6.5% · 30 years

Principal$601
Interest$3,601
Insurance$242

Estimates only. Actual payments may vary.

Location

1249 Osceola Drive

Fort Myers, FL 33901

RIVERSIDE

Features & Amenities

Interior Features

LivingDiningRoomTubShowerSplitBedrooms

Exterior Features

DeckFenceAwnings

Property Details

Flooring

Wood

Construction

Brick Block Concrete WoodFrame

Pool Features

Deck

Parking

GarageOpen

Heating

Electric (Heating)Central

Cooling

Central AirElectric

Appliances

DryerDishwasherMicrowaveRangeRefrigeratorWasher

Questions & Answers

This 3-bedroom, 4-bathroom single family at 1249 Osceola Drive is listed at $831,000 ($240/sqft). The estimated monthly payment is $3,601 based on 20% down at 6.5% interest.

Key features include: Built in 1924, 0.29 acre lot, 2 stories. Interior Features: LivingDiningRoom, TubShower, SplitBedrooms. Exterior Features: Deck, Fence, Awnings.

This property is listed by Cliff Glansen and can be reached at 9549653990 or info@flatfee.com.

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CG

Cliff Glansen

Agent at Flatfee.com

(954) 965-3990

Listed by Flatfee.com

MLS# 2025016791· Source: listhub· Updated 168 days ago

Copyright © 2026 Florida Gulf Coast Multiple Listing Service, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

1249 Osceola Drive, Fort Myers, FL 33901

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