1248 Osceola Dr, Fort Myers, FL 33901
$1,354,000 - For Sale
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Property Details
Price: $1,354,000
Sq Ft: 3,582
($378 per sqft)
Bedrooms: 6
Bathrooms: 3
City:Fort Myers
County:Lee
Type:Single Family
Development:Riverside
Subdivision: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
/ N
Furnishings: Unfurnished
Pets Allowed: Yes
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Equipment:
Dishwasher
Disposal
Self Cleaning Oven
Wall Oven
Warming Tray
Interior Features:
Fireplace
French Doors
Exterior Features:
Screened Lanai/ Porch
View:
Y
Waterfront Description:
None
Amenities:
None
Financial Information:
Taxes: $12,200.00
Tax Year: 2025
Room Dimensions:
Laundry: Washer/ Dryer Hookup, In Garage, Laundry in Residence
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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 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.
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 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.
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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
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John R. Wood Properties
3255 Tamiami Trail North
Naples, FL 34103
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(239) 821-5162
The data relating to real estate for sale on this Website comes in part from the Broker Reciprocity Program (BR Program) of these sources: M.L.S. of Naples, Inc., Bonita Springs-Estero Association of REALTORS®, Southwest Florida MLS (Gulf Coast), My Florida Regional MLS DBA Stellar MLS, Sanibel and Captiva Island Association of Realtors®. Properties listed with brokerage firms other than Featured Home Listings are marked with the BR House Icon and detailed information about them includes the name of the Listing Brokers. The properties displayed may not be all the properties available through the BR Program. The data is updated every 4 hours, but can be influenced by delays from various real estate companies entering data in MLS. Some properties that appear for sale on this website may subsequently have sold or may otherwise no longer be available. All properties are subject to price or other changes without notice. For the most current information, please contact us using this form, or click on the "Request Info or Appointment" button on the search results and detailed property pages.
The source of this real property information is the copyrighted and proprietary database compilation of the © 2026 M.L.S. of Naples, Inc., © 2026 Bonita Springs-Estero Association of REALTORS®, © 2026 Southwest Florida MLS (Gulf Coast), © 2026 My Florida Regional MLS DBA Stellar MLS and © 2026 Featured Home Listings, a Florida Real Estate Brokerage. 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. Information last refreshed: 2026-06-06 23:39:57
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