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1248 Osceola Drive Fort Myers FL 33901

$1,350,000
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1248 Osceola Drive, Fort Myers, FL 33901 - MLS#2026006878 1248 Osceola Drive, Fort Myers, FL 33901 - MLS#2026006878 1248 Osceola Drive, Fort Myers, FL 33901 - MLS#2026006878 1248 Osceola Drive, Fort Myers, FL 33901 - MLS#2026006878

Zev Freidus Broker / President
Zev Freidus
Broker / President
561-235-2161
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Overview of 1248 Osceola Dr

6 Bedrooms
3 Bathrooms
3 Car Garage
4,352 Square Feet
3,582SF Living Area
Pool:
Yes
Water: None
Year Built 1925
Listed For 27 Days

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 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. The property also 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 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 with sidewalks 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.

This luxury single family home was built in 1925 and features 6 bedrooms, and 3 full bathrooms. This home for sale is 4,352 square feet, with 3,582 sq ft being air conditioned living space. The home has a 3 car garage and has a private swimming pool.

Directions to this property are as follows: Mcgregor Blvd To West On Osceola Dr To 1248 On The Left.

Please contact your ZFC agent for more information about MLS# 2026006878 or any other homes for sale in Fort Myers or elsewhere in the Lee County area.

Features & Amenities

Appliances

Built In Oven, Dishwasher, Disposal, Self Cleaning Oven, Warming Drawer

Architecture

Two Story

Cooling

Central Air, Ceiling Fans, Electric

Heating

Central, Electric

Flooring

Tile, Wood

Parking

Driveway, Detached, Garage, Paved, Rv Access Parking, Two Spaces, Garage Door Opener

Lot Dimensions

120 x 175 x 121 x 181

Lot Size

Acres

View

Landscaped view

Construction Materials

Block, Concrete, Stucco

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

Furnished

Unfurnished

Exterior Features

Fence, None, Patio

Lot Features

Rectangular Lot

Property Condition

Resale

Patio And Porch Features

Lanai, Patio, Porch, Screened

Pool Features

Concrete, Electric Heat, Heated, In Ground, Pool Equipment, Screen Enclosure

Door Features

French Doors

Roof

Tile

Window Features

Single Hung

Utilities

Cable Available

Waterfront Features

None

Irrigation Source

Municipal, Well

Laundry

Washer Hookup, Dryer Hookup, Inside, In Garage

Number Of Stories

2

Year Built

1925

Pets Allowed

Yes

Annual Real Estate Taxes

$12,200 (2025)

Legal Description

Riverside Blk G Pb 3 Pg 63 Lot 3 + E 1/2 Lot 4

Property Type

Single Family Home

Association Fee Includes

None

Association Amenities

None

Other Structures

Gazebo

Community Features

Non Gated

Direction Faces

North

MLS Number

2026006878

Universal Property Id

U S-12071-N-264424 P40290 G0030-R-N

Days On Market

27

Community Name

Riverside

1248 Osceola Dr Price Calculator

Get Mortgage Quote For This Home

The payment calculator figures for 1248 Osceola Dr should be used as an estimate only. Loan terms including interest rate, and required downpayment will vary with each lender and/or individual. RE taxes for this home for sale are estimated based on the actual property taxes for this property for the tax year 2025 which are $12,200 but will likely change when this home sells. These estimations are calculated from a list price of $1,350,000 and a 25% down payment and do not include homeowners insurance which will vary greatly depending on the home characteristics and location.

Recent Home Sales near 1248 Osceola Dr

Address Sale Price Bed Bth Size Location Sale Date
1263 Caloosa DR $Log in to view 4 4/0 4,506SF Riverside 10/09/2025
1434 Alhambra DR $Log in to view 4 3/1 5,118SF Fort Myers 10/08/2025
1245 Gasparilla DR $Log in to view 5 3/1 4,911SF Stuart Subdivision 10/07/2025
1691 McGregor Reserve DR $Log in to view 4 3/0 4,271SF Mc Grefor Reserve 06/02/2025
1320 Alcazar AVE $Log in to view 5 3/1 4,229SF Valencia Terrace 07/23/2025
1751 Marlyn RD $Log in to view 3 3/1 3,897SF Edison Park Historic District 08/29/2025
1717 Whittling CT $Log in to view 3 3/0 3,841SF Mc Grefor Reserve 04/29/2025
1256 Morningside DR $Log in to view 4 3/0 3,763SF Seminole Estates 06/16/2025
1375 Barcelona AVE $Log in to view 5 3/1 3,340SF Valencia Terrace 08/08/2025
1324 Rio Vista AVE $Log in to view 4 3/0 3,327SF Rio Vista 06/27/2025
1313 Gasparilla DR $Log in to view 5 4/1 5,277SF York Manor 12/30/2025
1295 Wales DR $Log in to view 4 4/2 4,978SF Burtwood 03/14/2025

MLS# 2026006878 Listing History

02/08/2026 Listed for sale by List In MLS Realty, LLC with MLS# 2026006878 with a list price of $1,350,000.

Lee County Schools

Elementary School

Middle School

This listing of 1248 Osceola Dr Fort Myers FL 33901 was last updated on 2026-02-11 11:34:33. Listing courtesy of List In MLS Realty, LLC.
MLS

Map of 1248 Osceola Dr Fort Myers FL 33901

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Zev Freidus Broker / President
Zev Freidus
Broker / President
561-235-2161
Call Me
Text Me
Email Me
When clicking Submit Request, you are registering to this website and agreeing that ZFC Real Estate, its affiliates or associated third parties may contact you, including with calls or texts by automated means. You also agree to our Terms of Use and Privacy Policy

The data relating to homes for sale or lease or other real estate for sale or for rent on the ZFC website comes in part from a cooperative data exchange program of the MLS in which this Broker participates. The real estate displayed may not be all of the homes in the database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Homes for sale that are listed by Brokers other than this Broker are marked with either the listing Broker's name or the MLS name or a logo provided by the MLS and the details page about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. ZFC, the Florida Association of Realtors and its cooperating Multiple Listing Services do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law including the fair housing act prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

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