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$1,350,000

  • For Sale
  • Active
  • Single Family
  • 6 Beds
  • 3 Full Baths
  • 3,582 Sq. Ft.
  • Updated 13 days ago
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Step into a piece of history with this captivating 1925 Spanish Colonial home, thoughtfully updated for modern living while preserving its timeless charm. OWNER FINANCING available with a substantial down payment, providing an excellent opportunity to make this dream home yours. Situated in the heart of the historic McGregor District in Old Fort Myers, this exceptional property offers an unmatched blend of elegance and comfort. Nestled on nearly half an acre just a stone's throw from the river, this beautiful residence boasts 4 spacious bedrooms, 2 bathrooms, a den, and a bright, inviting family room. The expansive kitchen is a chef's delight, featuring a center island, double sinks, recessed oven, wood cabinets with stained glass accents, and an eat-in breakfast nook. French doors open to an extensive lanai and an oversized pool, perfect for entertaining or relaxing. Enjoy formal dinners in the stately dining room or unwind in the cozy sitting room by the wood-burning fireplace. A charming private courtyard adds to the home's unique appeal. The property also includes a separate guest house with 2 bedrooms, 1 bath, a kitchen, and living areas above an oversized 3-car garage, ideal for visitors or in-laws. Recent updates include new roofs and plumbing in 2020, restored hardwood floors, and hurricane-rated windows, ensuring both beauty and peace of mind. The location offers easy access to Fort Myers Country Club, the Edison-Ford Winter Estates, hospitals, top-rated public and private schools, diverse dining and shopping options, RSW Airport, and the pristine beaches of the Gulf of Mexico. Enjoy evening strolls in this wonderful neighborhood with sidewalks lined with mature trees. Don't miss your chance to own a piece of Fort Myers history in a highly sought-after community. Schedule your private showing today! No water intrusion or storm damage from Ian.

Full Property Details for 1248 Osceola Dr

General

  • Price: $1,350,000
  • Taxes: $12,200 (2025)
  • Status: Active
  • Type: Single Family
  • Source: Bonita_Springs
  • MLS ID: 2026006878
  • Updated: 2/11/2026
  • Added to Site: 17 day(s) ago

Interior

  • Interior Features: Kitchen, Living Room, Den - Study, Family Room, Home Office, Wired for Data
  • Fireplace: Yes
  • Appliances: Dishwasher, Disposal, Self-Cleaning Oven, Wall Oven, Warming Drawer
  • Furnishings: Unfurnished
  • Flooring: Tile, Wood

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 3
  • Primary Bathroom: Dual Sinks, Shower Only

Bedrooms

  • Total Bedrooms: 6

Other Rooms

  • Kitchen: Kitchen Island
  • Dining Room: Eat-in Kitchen, Formal
  • Laundry: Washer/Dryer Hookup, In Garage, Inside

Additional Information

  • Shared Amenities: None, Non-Gated
  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: In Ground, Concrete, Equipment Stays, Electric Heat, Screen Enclosure

Exterior

  • Porch/Patio/Deck: Screened Lanai/Porch, Patio

Parking

  • Garage: Yes
  • Garage Spaces: 3
  • Covered Spaces: 3
  • Parking Features: 2+ Spaces, Driveway Paved, Paved, RV-Boat, Garage Door Opener, Detached, Garage

Location

  • Area: FM01 - Fort Myers Area
  • County: Lee
  • Subdivision: RIVERSIDE
  • Building Name: RIVERSIDE
  • Driving Directions: McGregor Blvd to West on Osceola Dr to 1248 on the Left.
  • Direction Faces: North

Community

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

Heating & Cooling

  • Air Conditioning: Yes
  • Cooling Type: Ceiling Fan(s), Central Electric
  • Heating Type: Central Electric, Fireplace(s)

Utilities

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

Structural Information

  • Description/Design: Single Family Residence
  • Exterior Const.: Concrete Block, Stucco
  • Roof: Tile
  • Windows: Single Hung
  • Doors: French Doors
  • Entry Floor Number: 1
  • Stories/Levels: 2
  • Stories in Building: 2
  • Square Feet: 3,582
  • Sq. Ft. Source: Property Appraiser Office
  • Living Area: 3,582 Sq. Ft.
  • Year Built: 1925

Additional Structures

  • Other Structures: Guest House, Gazebo

Lot Features

  • Property View: Landscaped Area
  • Lot Size (Acres): 0.493
  • Lot Size (Sq. Ft.): 21,475
  • Lot Size Source: Property Appraiser Office
  • Lot Dimensions: 120 x 121 x 175 x 181
  • Frontage Feet: 120
  • Street/Road Desc.: Paved
  • Fence: Yes
  • Irrigation System: Central, Well
  • Lot Features: Regular
  • Zoning: RS-5
  • Lot Description: Regular
  • Fencing (Description): Fenced

Water Features

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

Financial Considerations

  • Tax Amount: $12,200
  • Tax Year: 2025
  • Terms: Buyer Finance/Cash, Consider 1st Mortgage, Consider 2nd Mortgage, Owner Will Carry

Disclosures and Reports

  • Ownership: Single Family
  • Legal Description: RIVERSIDE BLK G PB 3 PG 63 LOT 3 + E 1/2 LOT 4
  • Property ID: 26-44-24-P4-0290G.0030
  • Section: 26
  • Block: G
  • Lot Number: 3

Listed by List In MLS Realty, LLC

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— 1248 Osceola Dr —

  • List In MLS Realty, LLC

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NMLS#: 1598647

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Be ready to buy your new home!

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NMLS#: 1598647

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Schools serving 1248 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-51.4 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
Fort Myers High School
2635 Cortez Boulevard, Fort Myers, FL 33901
9-121 mi
Dunbar High School
3800 Edison Avenue, Fort Myers, FL 33916
9-123.4 mi
Cypress Lake High School
6750 Panther Lane, Fort Myers, FL 33919
9-125.3 mi
Franklin Park Elementary School
2323 Ford Street, Fort Myers, FL 33916
K-52.8 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 1248 Osceola Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
2/08/2026
Listed
$1,350,000
117.74%
MLS
1/08/2021
Sold
$620,000
—
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 1248 Osceola Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$10,835
-10%
$704,011
3%
2024
$12,008
1%
$684,170
3%
2023
$11,835
7%
$664,243
24%
2021
$11,095
-6%
$534,570
-17%
2022
$11,779
6%
$644,896
27%
2021
$11,095
-2%
$507,926
-1%
2018
$11,330
-2%
$515,179
—
2017
$11,600
2%
$516,787
—
2016
$11,379
10%
$517,992
16%
2015
$10,329
5%
$445,888
5%
2014
$9,836
-11%
$424,521
-17%
2019
$11,052
99%
$513,583
61%
2013
$5,554
—
$319,393
—
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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1248 Osceola Dr, Fort Myers, FL 33901 (MLS# 2026006878) is a Single Family property with 6 bedrooms and 3 full bathrooms. 1248 Osceola Dr is currently listed for $1,350,000 and was received on February 08, 2026. Want to learn more about 1248 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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