1249 Osceola DR, Fort Myers, FL 33901

• 3 beds |
• 4 baths |
• 3,467 sqft

Property Description

Two houses for the price of one. This historic home checks all the boxes, and one the best locations, close to downtown, schools, hospitals, kept mostly original to its original build, with updated electrical and plumbing, roof is only 3 years old. Never any flooding from any hurricanes in 22 years of ownership. In a neighborhood known for its close-knit neighbors, kid friendly sidewalks, pet friendly sidewalks. With a multi-family designation, the super cute guest house has many possibilities let a caretaker live in the guest house while you leave for the summer and have no worries, rent the guest house? 3-bedroom main house, and a 1-bedroom guest house. Two car garage with plenty of room to store a boat or RV. Remember this is a 100-year-old home, antique homes are known for lack of closet space, kitchen is outdated, all bedrooms are upstairs. Tremendous possibilities or keep as is. Most historic homes have been altered and changed many times over the years, this home has been kept and maintained as original as possible. Hence the new owner with have an original canvas to work with. Keep as is, or? If you like historic old homes, this is the one. Home is featured in Pam Miners book 'River & Road' Fort Myers Architecture from Craftsman to Modern. Chapter One. This is a unique home for that unique buyer. Location, location.

Listing Status:

Active

Date Added:

November 5, 2026

Data Last Updated:

November 14, 2026 at 7:17AM

Listing Office:

Flatfee.com : 954-965-3990

Listing Agent:

Cliff Glansen : 954-965-3990

MLS ID:

2026046609

Interior

• General: Living/Dining RoomOtherTub ShowerSplit Bedrooms
• Appliances: DryerDishwasherMicrowaveRangeRefrigeratorWasher
• Laundry: In Garage
• Flooring: Wood
• A/C: Central AirElectric
• Heating: CentralElectric

Exterior

• General: DeckFenceNoneAwning(s)
• Style: Two Story
• Other Structures: Deck
• Parking: DetachedGarageTwo SpacesGarage Door Opener

Construction

• Roofing: Shingle
• General: BrickBlockConcreteWood Frame2

Location

• Road/Access: Paved
• HOA Amenities: 0.0
• Originating MLS: FGC_FORT
• County: Lee

Lot

• Zoning: RIVERSIDE BLK C PB 3 PG 63 LOT 1726-44-24-P4-0290C.0170

Utilities

• Utilities: Cable Available
• Water: Public
• Sewer: Public Sewer

Financial

• Source: FGC_FORT
• Ownership: Single Family