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1249 Osceola Drive

Fort Myers, FL 33901
  • $849,000
  • STATUS: Active
  • ON SITE: 117 Days
  • MLS #: 2025016791
UPDATED: 123 min ago
$849,000
  • 3
    BEDS
  • 0.29
    ACRES
  • 4
    BATHS
  • 0
    1/2 BATHS
  • 3,467
    SQFT
  • $245
    $/SQFT
Neighborhood:
Type:
Single-Family Home
Built:
1924
County:
Lee

School Information

Elementary School:
Middle School:
High School:

Description

Location, Location, Location, Historic charm, built in 1924, A unique preserved historic home that is part of Fort Myers Florida history, ready for a new caretaker, owner is downsizing and ready to move, well maintained as close to original build as possible with upgraded plumbing and electrical. Never any flooding from any of the recent storms like hurricane Ian, zero flooding. They knew where to build in 1924. Complete new roof is two years old with transferable warranty. Many consider between Gasparilla and Caloosa Drive on the riverside of McGregor the best location in Fort Myers. Active community, kid friendly and pet friendly sidewalks and streets. This is a unique home for that unique buyer that appreciates old historic warmth and charm. Room for a pool or maybe a pickleball court, quest house is one of the cutest self-contained guest houses with all new plumbing. Guest house has one bedroom, living room, dining area and small kitchen with a bathroom. With a multi-family designation, can be legally rented. Main house and guest house, you are getting two beautiful historic homes for the price of one. Two car garage and room to store RV or boat. Preserving the historical charm is something that has been admired by many. All bedrooms are upstairs. Home is featured in Pam Miners book 'River & Road' Fort Myers Architecture from Craftsman to Modern. Chapter One. Location, location, location

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© 2026 Florida Gulf Coast Multiple Listing Service, Inc. All rights reserved. The data relating to real estate for sale or lease on this web site comes in part from FGCMLS. Data deemed reliable but not guaranteed.IDX information is provided exclusively 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 is deemed reliable but is not guaranteed accurate by the MLS or Wentworth Realty Group. Data last updated 2026-02-19T00:23:52.44.
www.wentworthrealty.com/homes/169207587
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1249 Osceola Drive Fort Myers, FL 33901

  • Price: $849,000
  • Status: Active
  • On Site: 117 Days
  • Updated: 123 min ago
  • MLS #: 2025016791
3
Beds
4
Baths
0
½ Baths
0.29
Acres
3,467
SQFT
$245
$/SQFT
1924
Built
Neighborhood:
Riverside
County:
Lee
Area:
Fm01 - Fort Myers Area
Elementary School:
Allen Park
Middle School:
Fort Myers
High School:
Fort Myers
Property Description
Location, Location, Location, Historic charm, built in 1924, A unique preserved historic home that is part of Fort Myers Florida history, ready for a new caretaker, owner is downsizing and ready to move, well maintained as close to original build as possible with upgraded plumbing and electrical. Never any flooding from any of the recent storms like hurricane Ian, zero flooding. They knew where to build in 1924. Complete new roof is two years old with transferable warranty. Many consider between Gasparilla and Caloosa Drive on the riverside of McGregor the best location in Fort Myers. Active community, kid friendly and pet friendly sidewalks and streets. This is a unique home for that unique buyer that appreciates old historic warmth and charm. Room for a pool or maybe a pickleball court, quest house is one of the cutest self-contained guest houses with all new plumbing. Guest house has one bedroom, living room, dining area and small kitchen with a bathroom. With a multi-family designation, can be legally rented. Main house and guest house, you are getting two beautiful historic homes for the price of one. Two car garage and room to store RV or boat. Preserving the historical charm is something that has been admired by many. All bedrooms are upstairs. Home is featured in Pam Miners book 'River & Road' Fort Myers Architecture from Craftsman to Modern. Chapter One. Location, location, location
Exterior Features

Architectural Style Two Story Attached Garage YN No Carport Spaces 0 Carport YN No Construction Materials Brick Block Concrete Wood Frame Covered Spaces 2 Direction Faces South Entry Level 1 Exterior Features Deck Fence None Awning(s) Garage YN Yes Levels Two Parking Features Detached Garage Two Spaces Garage Door Opener Patio And Porch Features Deck Pool Private YN No Road Surface Type Paved Roof Shingle Spa YN No

Interior Features

Appliances Dryer Dishwasher Microwave Range Refrigerator Washer Cooling Central Air Electric Cooling YN Yes Flooring Wood Furnished Unfurnished Heating Central Electric Heating YN Yes Interior Features Living / Dining Room Other Tub Shower Split Bedrooms Laundry Features In Garage

Property Features

Association Amenities None Association Fee 0 Association Fee Includes None Association Fee2 0 Association Fee3 0 Association YN No Building Area Total 3467 Community Features Non- Gated Development Name RIVERSIDE Gulf Access YN False Irrigation Source None Land Lease Amount 0 Listing Terms All Financing Considered Cash FHA VA Loan Lot Features Rectangular Lot Ownership Single Family Pets Allowed Yes Possession Close Of Escrow Potential Short Sale YN No Property Condition Resale Property Sub Type Single Family Residence Property Sub Type Additional Single Family Residence Restrictions No Restrictions Senior Community YN No Sewer Public Sewer Tax Annual Amount 5323.21 Tax Year 2023 Unit Location 1 Utilities Cable Available Water Access Description None Water Source Public Waterfront Features None Waterfront YN No Zoning Description RS-5

Listing courtesy of Flatfee.com.


© 2026 Florida Gulf Coast Multiple Listing Service, Inc. All rights reserved. The data relating to real estate for sale or lease on this web site comes in part from FGCMLS. Data deemed reliable but not guaranteed.IDX information is provided exclusively 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 is deemed reliable but is not guaranteed accurate by the MLS or Wentworth Realty Group. Data last updated 2026-02-19T00:23:52.44.
 
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Wentworth Realty Group
12995 S Cleveland Ave #9
Fort Myers FL, 33907