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1248 Osceola DR FORT MYERS, FL 339011 / 16

$1,354,000

1248 Osceola DR

location_onFORT MYERS, FL 33901 · Lee County

6Beds3Baths3,582Sq Ft1925Built

About This Property

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.

infoProperty Details

Property Type
Single Family Residence
Year Built
1925
Living Area
3,582 sqft
Lot Size
0.49 acres
Bedrooms
6
Bathrooms
3
Garage Spaces
3
Ownership
Single Family
Days on Market
89
List Date
Feb 8, 2026
Annual Taxes
$12K (2025)
HOA Fee
$0

chairInterior Features

Appliances

DishwasherDisposalSelf Cleaning OvenWall OvenWarming Drawer

Flooring

TileWood

Cooling

Ceiling Fan(s)Central Electric

Heating

Central ElectricFireplace(s)

yardExterior & Lot

Construction

Concrete BlockStucco

Roof

Tile

Parking

2+ SpacesDriveway PavedPavedRV-BoatGarage Door OpenerDetachedGarage

Pool

In GroundConcreteEquipment StaysElectric HeatScreen Enclosure

Waterfront

None

View

Landscaped Area

Listed By

List In MLS Realty, LLC

239-936-5478