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$849,000

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 4 Full Baths
  • 3,467 Sq. Ft.
  • Updated 13 days ago
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Historic charm, built in 1924, A unique preserved home that is part of Fort Myers Florida history, ready for a new caretaker for the next 100 years, well maintained as close to original build as possible with upgraded plumbing and electrical. 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

Full Property Details for 1249 Osceola Dr

General

  • Price: $849,000
  • Taxes: (2023)
  • Status: Active
  • Type: Single Family
  • Source: Bonita_Springs
  • MLS ID: 2025016791
  • Updated: 1/4/2026
  • Added to Site: 86 day(s) ago

Interior

  • Interior Features: Split Bedrooms, Living Room, Other
  • Appliances: Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
  • Furnishings: Unfurnished
  • Flooring: Wood

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 4
  • Primary Bathroom: Combo Tub And Shower

Bedrooms

  • Total Bedrooms: 3

Other Rooms

  • Dining Room: Dining - Living
  • Laundry: In Garage

Additional Information

  • Shared Amenities: None, Non-Gated

Exterior

  • Exterior Features: Awning(s)
  • Porch/Patio/Deck: Deck

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2
  • Parking Features: 2+ Spaces, Garage Door Opener, Detached

Location

  • Area: FM01 - Fort Myers Area
  • County: Lee
  • Subdivision: RIVERSIDE
  • Building Name: RIVERSIDE
  • Driving Directions: McGregor Blvd to Osceola Drive turn towards the river house is on the right
  • Direction Faces: South

School Information

  • Elementary School: ALLEN PARK
  • Middle School: FORT MYERS
  • High School: FORT MYERS

Community

  • Assoc. Fees Include: None
  • Units Assoc/Comm: 1
  • Pets Allowed: Yes
  • Management Type: None

Heating & Cooling

  • Air Conditioning: Yes
  • Cooling Type: Central Electric
  • Heating Type: Central Electric

Utilities

  • Sewer: Central
  • Water: Central
  • Cable Available: Yes
  • Utility Description: Cable Available

Structural Information

  • Description/Design: Single Family Residence
  • Exterior Const.: Concrete Block, Wood Frame, Brick
  • Roof: Shingle
  • Entry Floor Number: 1
  • Stories/Levels: 2
  • Stories in Building: 2
  • Square Feet: 3,467
  • Sq. Ft. Source: Property Appraiser Office
  • Living Area: 3,467 Sq. Ft.
  • Year Built: 1924

Additional Structures

  • Other Structures: Guest House

Lot Features

  • Property View: None/Other
  • Lot Size (Acres): 0.289
  • Lot Size (Sq. Ft.): 12,588
  • Lot Size Source: Property Appraiser Office
  • Lot Dimensions: 154 x 81 x 81 x 154
  • Frontage Feet: 154
  • Street/Road Desc.: Paved
  • Fence: Yes
  • Irrigation System: None
  • Lot Features: Regular
  • Zoning: RS-5
  • Lot Description: Regular
  • Fencing (Description): Fenced

Water Features

  • Water Front Desc.: None
  • Canal Width: None

Financial Considerations

  • Tax Year: 2023
  • Terms: Buyer Finance/Cash, FHA, VA Loan

Disclosures and Reports

  • Ownership: Single Family
  • Legal Description: RIVERSIDE BLK C PB 3 PG 63 LOT 17
  • Property ID: 26-44-24-P4-0290C.0170
  • Section: 26
  • Block: C
  • Lot Number: 17

Listed by Flatfee.com

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— 1249 Osceola Dr —

  • Flatfee.com

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NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 1249 Osceola Dr

School District:Lee County School District, Fort Myers, FL
NameGradesDistance
Allen Park Elementary School
3345 Canelo Drive, Fort Myers, FL 33901
K-50.7 mi
Orangewood Elementary School
4001 Deleon Street, Fort Myers, FL 33901
K-51.2 mi
Edison Park Creative And Expressive Arts School
2401 Euclid Avenue, Fort Myers, FL 33901
K-51.3 mi
Fort Myers Middle Academy
3050 Central Avenue, Fort Myers, FL 33901
6-81.4 mi
Paul Laurence Dunbar Middle School
4750 Winkler Avenue, Fort Myers, FL 33966
6-84.6 mi
Cypress Lake Middle School
8901 Cypress Lake Drive, Fort Myers, FL 33919
6-85 mi
Fort Myers High School
2635 Cortez Boulevard, Fort Myers, FL 33901
9-120.9 mi
Cypress Lake High School
6750 Panther Lane, Fort Myers, FL 33919
9-125.3 mi
South Fort Myers High School
14020 Plantation Road, Fort Myers, FL 33912
9-125.9 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 1249 Osceola Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
1/04/2026
Price Reduced
$849,000
-1.16%
MLS
12/12/2025
Price Increased
$859,000
0.7%
MLS
10/24/2025
Listed
$853,000
38.03%
MLS
9/14/2005
Sold
$618,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 1249 Osceola Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$4,526
-17%
$316,738
3%
2024
$5,440
2%
$307,811
3%
2023
$5,323
-1%
$298,846
-36%
2021
$5,356
1%
$466,420
61%
2022
$5,295
-1%
$290,142
4%
2021
$5,356
3%
$277,802
4%
2018
$5,211
1%
$266,493
2%
2017
$5,175
1%
$261,012
2%
2016
$5,101
-2%
$255,643
-6%
2019
$5,200
1%
$271,556
-31%
2015
$5,147
—
$392,693
-8%
2014
$5,150
5%
$425,836
33%
2013
$4,902
—
$320,259
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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1249 Osceola Dr, Fort Myers, FL 33901 (MLS# 2025016791) is a Single Family property with 3 bedrooms and 4 full bathrooms. 1249 Osceola Dr is currently listed for $849,000 and was received on October 24, 2025. Want to learn more about 1249 Osceola Dr? Do you have questions about finding other Single Family real estate for sale in Fort Myers? You can browse all Fort Myers real estate or contact a Coldwell Banker agent to request more information.

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