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For Sale - Active
1248 Osceola Dr, Fort Myers, FL 33901 - 6 Bedroom Pool Home in Riverside
$1,354,000
MLS Number
2026006878
Bedrooms
6 or More
Bathrooms
3 Baths
Living Area
3,582 sq ft
Total Area
4,352 sq ft
Garage Spaces
3
Year Built
1925
Days on Market
101
home 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 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.
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.
fact_check The Basics
Property Type
Single Family
Gulf Access
No
Private Pool
Yes
Private Spa
No
Acres
0.493
Furnished
Unfurnished
Last Modified
1 week ago
roofing Building Features
Building Features
DSL/Cable Available
Building Style
2 Story
Construction Materials
Concrete Block, Stucco
Cooling
Ceiling Fan(s), Central Electric
Covered Spaces
3
Elevator
None
Floor Plan
2 Story
Floors
2
Garage Spaces
3
Patio and Porch
Patio
Other Structures
Gazebo
Rear Exposure
South
Roof
Tile
Storm Protection
None
View
Landscaped Area
Water Source
Central
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chair Interior Features
Appliances & Equipment
Auto Garage Door, Dishwasher, Disposal, Self Cleaning Oven, Wall Oven, Warming Tray, Washer/Dryer Hookup
Interior Features
Fireplace, French Doors
Additional Rooms
Den - Study, Family Room, Home Office, Laundry in Garage, Laundry in Residence, Screened Lanai/Porch
Kitchen Features
Island
Flooring
Tile, Wood
Gas
No
Laundry
Washer/Dryer Hookup, In Garage, Laundry in Residence
holiday_village Neighborhood and Community
Pets Allowed
Yes
Amenities
None
Neighborhood
Riverside
Neighborhood Type
Non-Gated
Included in Fees
None
HOA Restrictions
None
Chris Farrugia, M.B.A.
Realtor® at The Listing Naples Group
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The source of this real property information is the copyrighted and proprietary database compilation of the Southwest Florida MLS organizations. Copyright 2026 Southwest Florida MLS organizations. All rights reserved. The accuracy of this information is not warranted or guaranteed. This information should be independently verified if any person intends to engage in a transaction in reliance upon it.
Listing provided by List In MLS Realty, LLC.
