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$1,354,000
Monthly Est:$6,739
6 Beds
- 3 Baths
3 full baths
3,582sqft
1248 Osceola Dr, Fort Myers, FL 33901
$1,354,000
$6,739/moEst:
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Single Family Residence
Built in 1925
$-- HOA
0.49 acre lot
$378/sq.ft
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.
- Houzeo last checked: 53 minutes ago
- Listing updated: May 8, 2026 at 8:02 pm
- Listing Provided by: Mark Hetrick (239) 826-8037 DRE #261070196 | List In MLS Realty, LLC (239) 936-5478
- Source: Florida Gulf Coast MLS, Fort Myers-FL | MLS#: 2026006878

Property Details
Status
Active
Type
Single Family Residence
No. of Stories
2
County
City
Neighborhood
Year Built
1925
HOA Fees
-
Finished Area
3,582 sqft
Lot Size
0.49 acre lot
Basement Area
- sqft
MLS Name
Florida Gulf Coast MLS, Fort Myers
MLS Number
2026006878
MLS Status
Active
Days on Market
242
Cumulative Days on Market
89

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Location
Facts & Features
Rooms
Bedrooms & bathrooms
Bedrooms: 6
Bathrooms: 3
Interior
Cooling
Central Air, Ceiling Fans, Electric
Window Features
Single Hung
Exterior Features
Fence, None, Patio
Heating
Central, Electric
Interior Features
Bedroom On Main Level, Separate Formal Dining Room, Dual Sinks, Eat In Kitchen, French Doors Atrium Doors, Fireplace, Kitchen Island, Shower Only, Separate Shower, Cable Tv, Home Office
Sewer
Public Sewer
Flooring
Tile, Wood
Appliances
Built In Oven, Dishwasher, Disposal, Self Cleaning Oven, Warming Drawer
Construction
Year Built
Year Built: 1925
Home type
Single Family Residence
Roof
Tile
Construction Materials
Block, Concrete, Stucco
Architectural Style
Two Story
Property Condition
Resale
Utilities & Energy
Utilities
Cable Available
Laundry Features
Washer Hookup, Dryer Hookup, Inside, In Garage
Pool Features
Concrete, Electric Heat, Heated, In Ground, Pool Equipment, Screen Enclosure
Parking Features
Driveway, Detached, Garage, Paved, Rv Access Parking, Two Spaces, Garage Door Opener
Water Source
Public
Association Amenities
None
Other Features
Subdivision Name
Riverside
Community Features
Non Gated
Lot Features
Rectangular Lot
Patio And Porch Features
Lanai, Patio, Porch, Screened
Price History
| Date | Event | Price |
|---|---|---|
02/08/2026 Source: | Listed for Sale | $1,350,000 -0.30% $377/sqft |
02/08/2026 Source: | Price Decreased | $1,354,000 -9.73% $378/sqft |
06/06/2024 Source: | Listed for Sale | $1,500,000 $419/sqft |
06/06/2024 Source: | Off Market | $1,500,000 +141.94% $419/sqft |
01/08/2021 Source: | Sold | $620,000 $173/sqft |
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Based on information from the Florida Gulf Coast Multiple Listing Service, Inc. through Oct 09, 2026, 12:00PM. IDX information is provided exclusively for consumers’ personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All information provided is deemed reliable but is not guaranteed and should be independently verified. Some IDX listings have been excluded from this website. © 2026 Florida Gulf Coast Multiple Listing Service - All Rights Reserved.
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