Listing Provided Courtesy of List In MLS Realty, LLC
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.
Property Details
Price:
$1,350,000
MLS #:
2026006878
Status:
Active
Beds:
6
Baths:
3
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
RIVERSIDE
Neighborhood:
riverside
Listed Date:
Feb 8, 2026
Finished Sq Ft:
3,582
Total Sq Ft:
4,352
Lot Size:
21,475 sqft / 0.49 acres (approx)
Year Built:
1925
See this Listing
Schools
Interior
Appliances
Dishwasher, Disposal, Self Cleaning Oven, Wall Oven, Warming Tray
Bathrooms
3 Full Bathrooms
Cooling
Ceiling Fan(s), Central Electric
Flooring
Tile, Wood
Heating
Central Electric
Interior Features
Fireplace, French Doors
Laundry Features
Washer/Dryer Hookup, In Garage, Laundry in Residence
Levels
2
Exterior
Architectural Style
Two Story, Single Family
Association Amenities
None
Building Features
DSL/Cable Available
Construction Materials
Concrete Block, Stucco
Covered Spaces
3
Exterior Features
Screened Lanai/Porch
Fencing
Fenced
Garage Spaces
3
Lot Features
Regular
Other Structures
Gazebo
Parking Features
Driveway Paved, Paved, RV-Boat, Detached
Parking Spots
3
Parking Total
3
Patio And Porch Features
Patio
Roof
Tile
View
Landscaped Area
Waterfront Features
None
Financial
Tax Year
2025
Taxes
$12,200
Map
Community
- Address1248 Osceola DR FORT MYERS FL
- SubdivisionRIVERSIDE
- CityFORT MYERS
- CountyLee
- Zip Code33901
Subdivisions in FORT MYERS
- 7 LAKES CONDO
- ACREAGE & UNREC
- ALABAMA GROVE TERRACE
- ANIELS PLACE
- ARLINGTON
- AVALON PRESERVE
- BEAU RIVAGE
- BERMUDA CLUB CONDO
- BOTANICA LAKES 1
- BOWLING GREEN
- BRISTOL PARC
- BROOKSHIRE VILLAGE I
- CITRUS RIVER ESTATE
- COACH HOMES AT CONCORD POINT
- COCONUT CREEK PH 01
- COLONIAL CC PRCL 112
- COLONIAL TERRACE SUB
- COLONNADE/FORUM
- COLONY POINTE PH 01
- CORONADO
- COTTAGE POINT
- COTTONWOOD BEND/VERANDAH
- COVE/SIX MILE CYPRESS CONDO
- CYPRESS LAKE COUNTRY CLUB
- CYPRESS LAKE GARDENS CONDO
- CYPRESS TERRACE
- CYPRESS WOODS RV RESORT
- DANIELS PRESERVE
- DAVIS WOODS CONDO
- DEANS SUB
- DEEP LAGOON ESTATES
- DOS RIOS EXT UNR SUB
- EDISON PARK
- ENCLAVE/COLLEGE POINTE
- ENCLAVE/LAKES/THREE OAKS
- ENCLAVE/LKS/THREE OAKS PH 1
- FIDDLESTICKS COUNTRY CLUB
- FOREST LAKE TWNHMS PH I
- FORT MYERS SHORES
- FT MYERS SHORES
- FT MYERS VILLAS
- GATEWAY PH 04
- GATEWAY PH 14
- GLADIOLUS GARDENS CONDO
- GLADIOLUS PRESERVE
- GOVERNORS ISLAND CONDO
- GREEN TEE VILLAGE
- GREENGATE CONDO 01
- HAMLET
- HARBOR CLUB
- HARLEM LAKE
- HART TRUCK FARMS
- HEATHER RIDGE 02 BROOKSHIRE
- HENDRY ESTATES
- HERITAGE FARMS UNREC
- HERITAGE PALMS ESTATES
- HIDDEN HARBOR ESTATES
- HIGH POINT PLACE
- HIGH POINT PLACE PH 01
- IDLEWILD/VERANDAH
- ISLAND PARK
- ISLAND PARK VILLAGE HOMES SEC IV
- JAMES EVANS HOMESTEAD
- KELLY GREENS
- KELLY GREENS VERANDAS 01-07
- KELLY GREENS VERANDAS III
- KELLY GREENS VERANDAS V
- LAGUNA CARIBE
- LAGUNA CARIBE RV RESORT
- LAGUNA LAKES A B C D E G K & L
- LAKESIDE PARKER LAKES
- LAKEWOOD VILLAGE
- LAND MARK PROFESSIONAL CONDO
- LAS PALMAS
- LEE COUNTY UNINCORPORATED – L
- LEHIGH ACRES
- LEHIGH ACRES E 01/2
- LINDSFORD PH 2A
- LINDSFORD PH 3
- LINNDSFORD PHASE 2A
- MASTIQUE I
- MATERA
- MC GREGOR GROVES
- MCGREGOR MOBILE MANOR
- MERION VILLAGE CONDO
- MILL CREEK AT COLONIAL SEC V
- MIRROR LAKES
- MYSTIC GARDENS CONDO
- MYSTIC GARDENS DESC
- NATOMA PARK
- OAKMONT VILLAGE CONDO
- OASIS TOWER 01
- OASIS TOWER 1
- ORANGE HARBOR MOBILE HOME & RV
- PALAZZO III
- PALMER P A TR
- PALMETTO COVE
- PALMETTO PALMS RV RESIDENCE PH III
- PALMETTO PALMS RV RESIDENCE PH IV
- PALMLEE PARK
- PARADISE SHORES
- PARKWOODS I TWNHS COMMUNITY
- PASEO
- PEBBLE BEACH
- PINE MANOR
- PINES AT EAGLE RIDGE 01-11
- PINEWOOD VILLAS PH 02
- POINTE ROYALE CONDO A
- PORTICO
- PORTICO PH I
- PORTOFINO SPGS
- PORTOFINO V
- PROMENADE EAST/FORUM
- PROVINCETOWN CONDO
- RIO VISTA
- RIVA DEL LAGO CONDO
- ROYAL GREENS/GATEWAY CONDO
- ROYAL WOODS PH 01
- ROYAL WOODS PH 02
- RUSSELL PARK
- SABAL POINTE/MAJESTIC PALMS PH
- SABAL SPRINGS GOLF & RACQUET CLUB
- SAIL HARBOUR/HEALTH PARK
- SAIL HARBOUR/HEALTHPARK
- SAN CARLOS GROVE
- SAN CARLOS PARK
- SANDY KEY
- SEA BREEZE 01
- SEMINOLE PARK
- SIENA/PELICAN PRESERVE CONDO
- SOUTH GATE
- SOUTHWIND SUB
- ST TROPEZ
- STONEYBROOK/GATEWAY
- SUMMERLIN WOODS CONDO 1
- SUTTON WALK
- TERRA PALMA
- THE RESIDENCE
- TIMBER CREEK
- TIMBER CRK
- TIMBER CRK PH 4
- TIMBER CRK-PH 4
- TIMBERLAKE CONDO 02
- TIMBERLINE VILLAGE 02
- TOWN & RIVER ESTATES
- TRAILWINDS
- TRAVERS & HENDRYS
- VAL WARD CADILLAC INC
- VICTORIA COVE CONDO
- VILLA CAPRI/PELICAN PRESERVE
- VILLA CAPRI/PELICAN PRESERVET
- VILLAGE CEDARBEND CONDOVISION
- VILLAS CROSS CREEK PH 03
- WATERWAY BAY
- WESTBROOK PH 2
- WESTCHESTER CONDO I & 02
- WHISKEY CREEK CLUB ESTATE
- WHISKEY CREEK VILL GRN SEC 04
- WHISPERING PINES PH 2
- WHITEHEAD CREEK SUB
- WILDBLUE PH 1A
- WINDSONG
Market Summary
Current real estate data for Single Family in FORT MYERS as of May 07, 2026
1,765
Single Family Listed
117
Avg DOM
292
Avg $ / SqFt
$723,139
Avg List Price
Property Summary
- Located in the RIVERSIDE subdivision, 1248 Osceola DR FORT MYERS FL is a Single Family for sale in FORT MYERS, FL, 33901. It is listed for $1,350,000 and features 6 beds, 3 baths, and has approximately 3,582 square feet of living space, and was originally constructed in 1925. The current price per square foot is $377. The average price per square foot for Single Family listings in FORT MYERS is $292. The average listing price for Single Family in FORT MYERS is $723,139. To schedule a showing of MLS#2026006878 at 1248 Osceola DR in FORT MYERS, FL, contact your CENTURY 21 Carioti agent at 800-783-8847.
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