1248 Osceola DR

$1,354,000

  • 3582 sqft
  • 6 Beds
  • 3 Baths
  • 3 Garages

General Information

  • List Price : $1,354,000
  • City : FORT MYERS
  • Acres : 0.493
  • MLS Area : 4352
  • Status Type : Resale Property
  • Approx. Living Area : 3582
  • Furnished : Unfurnished
  • Date Created : 2026-02-08
  • MLS Number : 2026006878
  • State Or Province : FL
  • Subdivision : RIVERSIDE
  • County : Lee
  • Bedrooms : 6
  • Approx. Total Area : 4352
  • Year Built : 1925
  • Potential Short :
  • DOM : 89
  • Address : 1248 Osceola DR
  • Postal Code : 33901
  • Development : Array
  • Property Type : Residential
  • Bath Full : 3
  • Price per Sq Ft : $63
  • Property Id : 26-44-24-P4-0290G.0030
  • Status : Active
  • CDOM : 89

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.

Provided by List In MLS Realty, LLC

Detailed Property Information

  • Ownership : Single Family
  • Waterfront Y/N :
  • Boat Access : None
  • Cooling : Ceiling Fan(s), Central Electric
  • Kitchen : Island
  • Amenities : None
  • Restrictions : None
  • Building Design :
  • View : Landscaped Area
  • Waterfront Desc : None
  • Elementary School :
  • High School :
  • Floor Plan Type : 2 Story
  • Private Pool Y/N : 1
  • Bedroom Desc : First Floor Bedroom
  • Equipment : Auto Garage Door, Dishwasher, Disposal, Self Cleaning Oven, Wall Oven, Warming Tray, Washer/Dryer Hookup
  • Additional Rooms : Den - Study, Family Room, Home Office, Laundry in Garage, Laundry in Residence, Screened Lanai/Porch
  • Storm Protection : None
  • Building Features : DSL/Cable Available
  • Community Type : Non-Gated
  • Gulf Access Y/N :
  • Gulf Access Type :
  • Middle School :
  • Pets : Yes
  • Heating :
  • Windows :
  • Flooring : Tile, Wood
  • Private Spa Y/N :
  • Dining Desc : Eat-in Kitchen, Formal
  • Exterior Features : Screened Lanai/Porch

Unit / Building Information

  • Unit Floor : 1
  • Unit Number :
  • Construction : Concrete Block, Stucco
  • Total Floors : 2
  • Units in Building : 1
  • Elevator : None
  • Building Desc : 2 Story
  • Units in Complex : 1
  • Roof : Tile

Lot Information

  • Rear Exposure : S
  • Range :
  • Sewer :
  • Lot Unit :
  • Section :
  • Irrigation : Central, Well
  • Block : G
  • Township :
  • Water : Central
  • Lot Desc : Regular

Financial Information

  • Condo Fee : 0
  • Approval :
  • Tax Year : 2025
  • Condo Fee Freq :
  • Management : None
  • Possession : Array
  • Tax Desc : RIVERSIDE BLK G PB 3 PG 63 LOT 3 + E 1/2 LOT 4
  • Maintenance : None

Additional Details

  • Amenities : Island
  • County Or Parish : Lee
  • Foreclosed REOYN :
  • Gulf Access YN :
  • Irrigation : Central, Well
  • Legal Unit :
  • Lot Type :
  • Management : None
  • Master HOA Fee Freq :
  • Original List Price : 1350000
  • Parcel Number : 26-44-24-P4-0290G.0030
  • Planned Use :
  • Postal Code Plus :
  • Property Type : Residential
  • Restrictions : None
  • Section :
  • Source of Measurements :
  • State Or Province : FL
  • Street Dir Prefix :
  • Street Number : 1248
  • Sub Condo Name :
  • Unit Number :
  • View : Landscaped Area
  • Waterfront YN :
  • CDOM : 89
  • Close Date :
  • Community Type : Non-Gated
  • Date Created : 2026-02-08
  • Full Address : 1248 Osceola DR
  • Last Change Timestamp : 2026-05-08T20:00:03.203Z
  • List Price : $1,354,000
  • Lot Unit :
  • Mandatory Club Fee Freq :
  • MLS Area Major : FM01 - Fort Myers Area
  • Photo Count : 16
  • Possession : Array
  • Potential Short Sale YN :
  • Range :
  • Road : Paved
  • Sewer :
  • Status : Active
  • Street Dir Suffix :
  • Subdivision Info : RIVERSIDE
  • Table : Residential
  • Township :
  • Water : Central
  • Zoning Code: RS-5
  • Association Mngmt Phone : (239) 936-5478
  • Boat Access : None
  • Canal Width : $None
  • City : FORT MYERS
  • Condo Fee : 0
  • Condo Fee Freq :
  • Current Price : $1,354,000
  • DOM : 89
  • Elevation :
  • Gulf Access Type :
  • Master HOA Fee Freq : 0
  • Land Lease Fee Freq :
  • Last Change Type : Price Change
  • Legal Desc :
  • Maintenance : None
  • Mandatory HOA Y/N : 0
  • Matrix Modified DT : 2026-05-08T20:21:36.293Z
  • MLS Number : 2026006878
  • Other PI Ds :
  • Photo Modification Timestamp : 2026-02-08T14:16:29.804Z
  • Postal Code : 33901
  • Price Per Acre : 2,746,450
  • Rear Exposure : S
  • Room Count : 0
  • Source of Measure Lot Dimensions :
  • Status Type : Resale Property
  • Street Name : Osceola
  • Street Suffix : DR
  • Tax Desc : RIVERSIDE BLK G PB 3 PG 63 LOT 3 + E 1/2 LOT 4
  • Tax Year : 2025
  • Trees :
  • Utilities Available :
  • Waterfront Desc :
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1248 Osceola DR

$1,354,000