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1248 Osceola Dr, Fort Myers, FL 33901

$1,354,000
  • 1248 Osceola Dr, Fort Myers, FL 33901 Main Photo
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BEDS6 BATHS3 full SQUARE FEET3,582 MLS#2026006878
STATUSActive PROPERTY TYPEResidential - Single Family SUBDIVISIONRIVERSIDE

Property 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.

1248 Osceola Dr | MLS# 2026006878

This single family home located at 1248 Osceola Dr, Fort Myers, FL 33901 is currently listed for sale with an asking price of $1,354,000. This property was built in 1925 and has 6 bedrooms and 3 full baths with 3582 sq. ft. Osceola Dr is located in the RIVERSIDE subdivision. Search RIVERSIDE real estate on www.realtymarkllc.com today.

Property Features

Property Type: Residential - Single Family
Cooling: Ceiling Fan(s), Central Electric
Garage: 3
Heating: Central Electric, Fireplace(s)
Lot Size: 0.49 Acres
Roof Type: Tile
Stories: 2.0
Taxes: $12,200
Year Built: 1925

Feature Descriptions

Bedroom: 6 or More
Construction: Concrete Block, Stucco
Days on Site: 158
Dining: Eat-in Kitchen, Formal
Directions: McGregor Blvd to West on Osceola Dr to 1248 on the Left.
Exterior: Concrete Block, Stucco
Flooring: Tile, Wood
Furnished: Unfurnished
GEO Area: FM01 - Fort Myers Area
Hoa Fee: $0
Home Warranty Y/N: No
Interior: Kitchen, Living Room, Den - Study, Family Room, Home Office, Wired for Data
Irrigation: Central, Well
Kitchen: Kitchen Island
Laundry: Washer/Dryer Hookup, In Garage, Inside
Lease Considered Y/N: No
Listing Terms: Buyer Finance/Cash, Consider 1st Mortgage, Consider 2nd Mortgage, Owner Will Carry
Lot: Regular
Ownership: Single Family
Parcel #: 26-44-24-P4-0290G.0030
Parking: 2+ Spaces, Driveway Paved, Paved, RV-Boat, Garage Door Opener, Detached, Garage
Pets: No Approval Needed
Pool: In Ground, Concrete, Equipment Stays, Electric Heat, Screen Enclosure
Property Attached Y/N: No
Property Sub-Type: Single Family Residence
Road Surface: Paved
Sewer: Central
Sewer: Central
SQFT Total: 4352
Swimming Pool: Yes
Transfer Fee: 0
Units in Building: Square Feet
View: Landscaped Area
Water: Central
Water: Central
Windows: Single Hung

Listed By / Shown By

Listed By

Agency Name: List In MLS Realty, LLC
Agency Phone: 239-936-5478

Shown By

Agency Title: RealtyMark
Agency Phone: 888-260-0040

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Estimated Payment

$ 4,425.00 per month $3,013.42 Principal & Interest $1,016.67 Property Tax $394.92 Homeowner's Insurance

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All commissions are negotiable Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers 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 on this site was last updated 07/16/2026. The listing information on this page last changed on 07/16/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Thu 07/16/2026 1:15:51 AM EST) or Stellar MLS (last updated Thu 07/16/2026 12:59:10 AM EST) or GSMLS (last updated Thu 07/16/2026 12:24:10 AM EST) or Emerald Coast MLS (last updated Thu 07/16/2026 12:05:25 AM EST) or Fort Myers (last updated Wed 07/15/2026 11:04:48 PM EST) or Central Panhandle Association of Realtors (last updated Thu 07/16/2026 1:07:19 AM EST) or Northeast Florida MLS (last updated Thu 07/16/2026 12:18:59 AM EST) or Beaches MLS (last updated Thu 07/16/2026 1:08:20 AM EST) or Naples MLS (last updated Wed 07/15/2026 11:40:22 PM EST) or Bright MLS (last updated Thu 07/16/2026 12:38:31 AM EST) or OneKey MLS (last updated Thu 07/16/2026 1:10:26 AM EST). Real estate listings held by brokerage firms other than RealtyMark may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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