Fort Myers, FL 33901 1248 Osceola Drive

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Presented By: List In MLS Realty, LLC
  • MLS# 2026006878
  • 02/08/2026
  • Request Tour
  • Request Info
  • Beds • 6
  • Baths • 3
  • SQFT • 3,582
  • Garage • 3

Home Details

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.
Presented By: List In MLS Realty, LLC

Interior Features for 1248 Osceola Drive

Bedrooms

Total Bedrooms6

Bathrooms

Half Baths0
Total Baths3

Other Interior Features

LivingAreaSourceAppraiser
Air Conditioning Y/NYes
Fireplace Y/NYes
FlooringTile, Wood
Furnished Y/NUnfurnished
Heating Y/NYes
Interior AmenitiesBedroom on Main Level, Separate/Formal Dining Room, Dual Sinks, Eat-in Kitchen, French Door(s)/Atrium Door(s), Fireplace, Kitchen Island, Shower Only, Separate Shower, Cable TV, Home Office
Laundry FeaturesWasher Hookup, Dryer Hookup, Inside, In Garage
Total Stories2
Window FeaturesSingle Hung

Other Rooms

Entry Level1
Room TypeDen, Family Room, Office, Screened Porch

General for 1248 Osceola Drive

AppliancesBuilt-In Oven, Dishwasher, Disposal, Self Cleaning Oven, Warming Drawer
Architectural StyleTwo Story
Association AmenitiesNone
Association Fee IncludesNone
Attached Garage No
Carport Spaces
Carport Y/NNo
CityFort Myers
Community FeaturesNon-Gated
Construction MaterialsBlock, Concrete, Stucco
CoolingCentral Air, Ceiling Fan(s), Electric
CountyLee
DirectionsMcGregor Blvd to West on Osceola Dr to 1248 on the Left.
Facing DirectionNorth
Full Baths3
Garage Spaces3
Garage Y/NYes
HOANo
HOA Fee$
HOA Fee 2
HOA Fee 3
HeatingCentral, Electric
Land Lease Amount
Legal DescriptionRIVERSIDE BLK G PB 3 PG 63 LOT 3 + E 1/2 LOT 4
LevelsTwo
Lot Size UnitsAcres
MLS AreaFM01 - Fort Myers Area
Other StructuresGazebo
OwnershipSingle Family
Patio/Porch FeaturesLanai, Patio, Porch, Screened
Pets AllowedYes
Pool FeaturesConcrete, Electric Heat, Heated, In Ground, Pool Equipment, Screen Enclosure
PossessionClose Of Escrow
PostalCityFort Myers
Property ConditionResale
Property Sub Type AdditionalSingle Family Residence
Property SubtypeSingle Family Residence
Property TypeResidential
RoofTile
Senior Community Y/NNo
SewerPublic Sewer
Standard StatusActive
StatusActive
Stories Count2
Subdivision NameRIVERSIDE
Tax Annual Amount12200
Tax Lot3
Tax Year2025
UtilitiesCable Available
ViewLandscaped
Virtual TourClick here
Waterfront FeaturesNone
Year Built1925
Zoning DescriptionRS-5

Exterior for 1248 Osceola Drive

Building Area Total4352
Covered Spaces3
Door FeaturesFrench Doors
Exterior AmenitiesFence, None, Patio
Lot Dimensions120 x 175 x 121 x 181
Lot FeaturesRectangular Lot
Lot Size Acres0.493
Lot Size Area0.493
Lot Size SourceAppraiser
LotDimensionsSourceAppraiser
Parking FeaturesDriveway, Detached, Garage, Paved, RV Access/Parking, Two Spaces, Garage Door Opener
Private PoolYes
Road Surface TypePaved
SpaNo
Water SourcePublic
Waterfront Y/NNo

Additional Details

Price History

Schools

High School Hubert H Humphrey Middle School
Middle School N/A
Elementary School Big Hollow Elementary School

Claudia Betancur

Realtor®
Price $1,354,000
MLS#2026006878
List Date 02/08/2026
Property Type Single Family
Phone 954.397.3290
Request Tour
Request Info
Visit My Website

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