1248 Osceola Dr, Fort Myers, FL 33901
For Sale $1,350,000
Save Property
View Virtual Tour
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.
Fireplace
French Doors
None
Taxes: $12,200.00
Tax Year: 2025
Screened Lanai/ Porch
Dishwasher
Disposal
Self Cleaning Oven
Wall Oven
Warming Tray
Y
Building Description: Two Story, Single Family
Community Type: Non- Gated
MLS Area: Riverside
Total Square Footage: 4,352
Total Floors: 2
Water: Central
Construction: Concrete Block, Stucco
Short Sale: No
Date Listed: 2026-02-08 00:00:00
Pool: Y
Pool Description: Below Ground, Concrete, Equipment Stays, Electric Heat, Screen Enclosure
Furnished: Unfurnished
Kitchen Description: Island
Parking: Driveway Paved, Paved, R V- Boat, Detached
Garage Spaces: 3
Flooring: Tile, Wood
Roof: Tile
Heating: Central Electric
Cooling: Ceiling Fan(S), Central Electric
Fireplace: Y
Storm Protection: None
Laundry: Washer/ Dryer Hookup, In Garage, Laundry In Residence
Irrigation: Central, Well
Pets: Yes
Restrictions: None
Maintenance: None
Rear Exposure: S
Lot Desc.: Regular
Amenities: None
Listing Courtesy Of: List In Mls Realty, Llc
mark@listinmls.com
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.
Property Details
Price: $1,350,000
Sq Ft: 3,582
($377 per
sqft)
Bedrooms: 6
Bathrooms: 3
City: Fort Myers
County: Lee
Type: Single Family
Development: Riverside
Acres: 0.4930
Virtual Tour/Floorplan: View
Year Built: 1925
Listing Number: 2026006878
Status Code: A-Active
Taxes: $12,200.00
Tax Year: 2025
Application Fee: $0.00
Garage:
3
Furnishings: Unfurnished
Pets Allowed: Yes
Total Recurring Fee Frequency: 0.00
Interior Features:
Fireplace
French Doors
Amenities:
None
Financial Information:
Taxes: $12,200.00
Tax Year: 2025
Exterior Features:
Screened Lanai/ Porch
Equipment:
Dishwasher
Disposal
Self Cleaning Oven
Wall Oven
Warming Tray
View:
Y
Additional Information:
Building Description: Two Story, Single Family
Community Type: Non- Gated
MLS Area: Riverside
Total Square Footage: 4,352
Total Floors: 2
Water: Central
Construction: Concrete Block, Stucco
Short Sale: No
Date Listed: 2026-02-08 00:00:00
Pool: Y
Pool Description: Below Ground, Concrete, Equipment Stays, Electric Heat, Screen Enclosure
Furnished: Unfurnished
Kitchen Description: Island
Parking: Driveway Paved, Paved, R V- Boat, Detached
Garage Spaces: 3
Flooring: Tile, Wood
Roof: Tile
Heating: Central Electric
Cooling: Ceiling Fan(S), Central Electric
Fireplace: Y
Storm Protection: None
Laundry: Washer/ Dryer Hookup, In Garage, Laundry In Residence
Irrigation: Central, Well
Pets: Yes
Restrictions: None
Maintenance: None
Rear Exposure: S
Lot Desc.: Regular
Amenities: None
Map of 1248 Osceola Dr, Fort Myers, FL 33901
Listing Courtesy Of: List In Mls Realty, Llc
mark@listinmls.com