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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 $881,000 ($254 per sqft). Built in 1924, the home offers 3,467 sqft of living space on a 0.29 acres lot.

Agent Description

New price, Awesome possibilities, Historic charm, built in 1924, unique preserved historic home that is part of Fort Myers Florida history, ready for a new owner caretaker, current owner is ready to move, owner is no longer requesting a contingency of finding a replacement home, can close quickly, well maintained as close to original historic build as possible with upgraded plumbing and electrical.

Never any flooding from any of the recent storms like hurricane Ian, zero flooding. 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. Socially active community, Quiet, kid friendly and pet friendly sidewalks and streets.

Norman Rockwell like. This is a unique home for that unique buyer that appreciates old historic warmth and charm. Room for a pool, 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

$4,712/mo

20% down · 6.5% · 30 years

Principal$637
Interest$3,818
Insurance$257

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

OpenGarage

Heating

CentralElectric (Heating)

Cooling

Central AirElectric

Appliances

DryerDishwasherMicrowaveRangeRefrigeratorWasher

Questions & Answers

This 3-bedroom, 4-bathroom single family at 1249 Osceola Drive is listed at $881,000 ($254/sqft). The estimated monthly payment is $3,818 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.

CG

Cliff Glansen

Agent at Flatfee.com

(954) 965-3990

Listed by Flatfee.com · View on Broker Site

MLS# 2025016791· Source: listhub· Updated 220 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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