$1,350,000

1248 Osceola DR, Fort Myers, FL 33901

6 beds |
3 baths |
3,582 sqft

Single-Family Home
Built in 1925
0.49acre lot
3 car garage
$377/sqft
Listed 4 days ago

Property Description

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.

Listing Status:: Active
Date Added:: February 8, 2026
Data Last Updated:: February 12, 2026 at 7:07AM
Listing Office:: List In MLS Realty, LLC : (239) 936-5478
MLS ID:: 2026006878

General: FireplaceFrench Doors
Kitchen: Island
Appliances: DishwasherDisposalSelf Cleaning OvenWall OvenWarming Tray
Dining: Eat-in KitchenFormal
Laundry: Washer/Dryer HookupIn GarageLaundry in Residence
Flooring: TileWood
A/C: Ceiling Fan(s)Central Electric
Heating: Central Electric
Fireplace: Fireplace

General: Screened Lanai/PorchGazebo
Style: Two StorySingle Family
Pool: Below GroundConcreteEquipment StaysElectric HeatScreen Enclosure
Parking: Driveway PavedPavedRV-BoatDetachedParking spaces: 3

Roofing: Tile
General: Concrete BlockStucco2Concrete Block

Road/Access: Paved
HOA Amenities: 0.0
Originating MLS: Florida Gulf Coast
County: Lee

Zoning: RS-526-44-24-P4-0290G.0030
View: Landscaped AreaView
Fencing: Fenced
Restrictions: None

Water: Central

Source: Florida Gulf Coast

This listing courtesy of List In MLS Realty, LLC

Monthly Payment

$Est. Payment

Principal & Interest $
Property Taxes $
Home Insurance $
VA Funding Fee $

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Location

Schools Nearby

Allen Park Elementary School

3345 Canelo Dr, Fort Myers, FL, 33901

Grades KG-5

0.67 miles away

Coronado High School

3057 Cleveland Ave, Fort Myers, FL, 33901

Grades 7-12

1.05 miles away

Fort Myers High School

2635 Cortez Blvd, Fort Myers, FL, 33901

Grades 9-12

1.01 miles away

Disclaimer: School and School District information courtesy of the National Center for Education Statistics (NCES). School boundaries may change. Proximity to listed schools does not guarantee enrollment eligibility. Contact the school district for more information and exact boundaries.