Skip to content
Bean Group
Offered at $1,354,000Active
beds
6
baths
3
sq ft
3,582
Built
1925

1248 Osceola Drive

Fort Myers, FL 33901

About this home

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.

Listing last checked: Listing updated:

Listed by Mark Hetrick · List In MLS Realty, LLC · MLS #2026006878

Request property information

Select a document to start a request. You can add others in the form. Availability varies.

Details at a glance

Interior3 property facts
Heating
Central, Electric
Cooling
Central Air, Ceiling Fan(s), Electric
Flooring
Tile, Wood
Building4 property facts
Style
Single Family Residence
Year built
1925
Garage
3
Roof
Tile
Land & utilities3 property facts
Lot size
0.493 acres
Water
Public
Sewer
Public Sewer
Financial3 property facts
Annual taxes
$12,200
Assessment year
2025
HOA fee
$0 (billing period not supplied)

Location

Estimated monthly cost

Explore costs at the $1,354,000 asking price. Adjust the assumptions to your situation.

Known monthly costs$7,863 / monthAdjust
Principal & interest
$6,847
Property tax
$1,017
Insurance
Not entered
HOA
$0

Listing annual taxes: $12,200. Initial monthly tax is one twelfth of that amount. Listing HOA fee: $0.

Partial estimate: add insurance to include those costs. Blank amounts are unknown.

The initial 6.5% rate is illustrative, not a current rate or lender quote. Excludes utilities, maintenance, closing costs and mortgage insurance, which may apply with a down payment below 20%. Taxes and insurance can change.

Price and status timeline

  1. Sld

    $699,000 · Sold $620,000 · Aug 29, 2020

  2. Sld

    $469,000 · Sold $455,000 · Mar 12, 2013

Explore more of Fort Myers

Continue your search in Fort Myers.

Need help making sense of this home?

About 1248 Osceola Drive

Can I request a private showing?

Request a tour of 1248 Osceola Drive and a Bean Group agent will help coordinate an available time with the listing side.

Can you help me evaluate this property?

Yes. We can discuss condition, comparable sales, offer strategy and the questions worth asking before you decide whether to proceed.

Are property documents available?

Availability varies by property and source. Request the documents you need and we will help obtain what is available.