1248 Osceola Drive $1,354,000

Updated
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 home is located in a quiet, highly desirable community known for its socially active lifestyle, with sidewalks and streets that are both kid and pet friendly. 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. A downstairs bedroom provides added flexibility for guests or multigenerational living. The property also offers abundant parking, ideal for a boat, RV, or additional recreational toys. The property 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 front of the property is scheduled for a full re-landscaping, designed to further enhance curb appeal and create an even more impressive, picturesque estate entrance. 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 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.
General Amenities
Interior Amenities
Exterior Amenities
Landscape Amenities
Community Amenities
Appliance Amenities
Accessibility Amenities
Beds
6
Baths
3.00
Ft2
3,582
Lot Acres
0.49
Year Built
1925
Cooling
CentralAir,CeilingFans,Electric
Roof
Tile
Virtual Tour
1248 Osceola Drive
Fort Myers, Florida 33901
United States
Subdivision: RIVERSIDE
County: Lee
Sale Type: For Sale
Ref #: 2026006878
Last Updated: Friday, 08 May 2026 08:02
Listed by List In MLS Realty, LLC [For Sale]
Beds
6
Baths
3.00
Ft2
3,582
Lot Acres
0.49
Heat
Central,Electric
Cooling
CentralAir,CeilingFans,Electric
Roof
Tile
Year Built
1925
Garage Size
3
Beds
6
Baths
3.00
Ft2
3,582
Lot Acres
0.49
Year Built
1925
Cooling
CentralAir,CeilingFans,Electric
Roof
Tile
Virtual Tour
1248 Osceola Drive
Fort Myers, Florida 33901
United States
Subdivision: RIVERSIDE
County: Lee
Sale Type: For Sale
Ref #: 2026006878
Last Updated: Friday, 08 May 2026 08:02
Listed by List In MLS Realty, LLC [For Sale]