Riverside, 1248 Osceola Dr

6
Beds
3
Baths
3,582
SqFt
Status
Active
Parking
3
Size
3,582 SqFt (333 m2)
Price
$378/SqFt ($4,069/m2)
Type
House
Built
1925
HOA
N/A
MLS Number
2026006878
View
Landscaped Area
Updated
119 Days ago
Page Views
0
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.

Features

Bedrooms
  • Bedrooms: 6
Bathrooms
  • Bathrooms: 3
  • Half Bathrooms: No info
Exterior and Lot Features
  • Exterior Features: Screened Lanai/Porch
  • View: Landscaped Area
Interior, Heating and Cooling
  • Interior Features: Fireplace, French Doors
  • Equipment / Appliances: Dishwasher, Disposal, Self Cleaning Oven, Wall Oven, Warming Tray
  • Heating Description: Central Electric
  • Cooling Description: Ceiling Fan(s), Central Electric
Building and Construction
  • Floor Description: Tile, Wood
  • Windows/Treatment: No info
  • Construction Type: House
  • Year Built: 1925
  • Style: Two Story, Single Family
Waterfront and Water Access
  • Waterfront Frontage: No info
School Information
    Other Property Info
    • Garage: 3
    • Pets Allowed: Yes
    Taxes, Fees & More
    • Maintenance Includes: None
    • Taxes: 12200
    • Security Information: No info
    • Parking Description: Driveway Paved, Paved, RV-Boat, Detached
    • Total Floors in Building: 2
    • Total Units in Building: 1

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    Price History

    Current
    $1.4M
    High
    $1.4M
    Low
    $1.4M
    Total Change
    0.3%
    $1.4M$1.4M$1.3MFeb 26May 26
    Date
    Event
    Price
    Change
    Price Per
    05/08/2026
    Price Increased
    $1.4M
    0.3%
    $378 ft2
    $4,069 m2
    02/08/2026
    Listed
    $1.4M
     
    $377 ft2
    $4,057 m2
    05/08/2026
    $1.4M
    Event
    Price Increased
    Change
    0.3%
    Price Per
    $378 ft2
    $4,069 m2
    02/08/2026
    $1.4M
    Event
    Listed
    Price Per
    $377 ft2
    $4,057 m2
    Price per square foot and days on website are not provided values and are calculated by Subdivisions.
    Listed by Mark Hetrick • List In MLS Realty, LLC • Buyer Agency Compensation .

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    Scores

    Walk Score®
    Car-Dependent. Almost all errands require a car
    12

    100
    Bike Score®
    Somewhat Bikeable. Minimal bike infrastructure
    31

    100
    Sound Score®
    Bearable noise
    79

    100
    Airport Score
    Close to airports. Noticeable airport activity
    0

    100
    Traffic Score
    Congested area. Frequent traffic delays
    26

    100
    Local Score
    Limited local amenities nearby
    0

    100
    Community Snapshot
    3 – 6 BR
    Bedrooms
    $881K – $1.4M
    Price Tier
    1,379 - 8,677
    SqFt Range
    1953
    Year Build
    2
    Total Floors

    Subdivision Amenities

    Fitness Center
    Guest Room
    Internet Access
    See Remarks
    Shopping
    Sidewalk
    Streetlight
    Bike And Jog Path
    Fitness Center
    Internet Access
    None
    Park
    Sidewalk
    Streetlight

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