Listing Provided Courtesy of Flatfee.com
New price, Awesome possibilities, Historic charm, built in 1924, unique preserved historic home that is part of Fort Myers Florida history, ready for a new owner caretaker, current owner is ready to move, owner is no longer requesting a contingency of finding a replacement home, can close quickly, well maintained as close to original historic build as possible with upgraded plumbing and electrical. Never any flooding from any of the recent storms like hurricane Ian, zero flooding. Complete new roof is three years new. Many consider between Gasparilla and Caloosa Drive on the riverside of McGregor the best location in Fort Myers. Socially active community, Quiet, kid friendly and pet friendly sidewalks and streets. Norman Rockwell like. This is a unique home for that unique buyer that appreciates old historic warmth and charm. Room for a pool, 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. Priced to sell
Property Details
Price:
$829,000
MLS #:
2025016791
Status:
Active
Beds:
3
Baths:
4
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
RIVERSIDE
Neighborhood:
riverside
Listed Date:
Oct 24, 2025
Finished Sq Ft:
3,467
Total Sq Ft:
3,467
Lot Size:
12,589 sqft / 0.29 acres (approx)
Year Built:
1924
See this Listing
Schools
Elementary School:
ALLEN PARK
Middle School:
FORT MYERS
High School:
FORT MYERS
Interior
Appliances
Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
Bathrooms
4 Full Bathrooms
Cooling
Central Electric
Flooring
Wood
Heating
Central Electric
Interior Features
Other
Laundry Features
In Garage
Levels
2
Exterior
Architectural Style
Two Story, Single Family
Association Amenities
None
Construction Materials
Concrete Block, Wood Frame, Brick
Covered Spaces
2
Exterior Features
Awning(s)
Fencing
Fenced
Garage Spaces
2
Lot Features
Regular
Parking Features
Detached
Parking Spots
2
Parking Total
2
Patio And Porch Features
Awning(s), Deck
Roof
Shingle
Waterfront Features
None
Financial
Tax Year
2023
Taxes
$5,323
Map
Community
- Address1249 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 18, 2026
1,718
Single Family Listed
121
Avg DOM
290
Avg $ / SqFt
$713,412
Avg List Price
Property Summary
- Located in the RIVERSIDE subdivision, 1249 Osceola DR FORT MYERS FL is a Single Family for sale in FORT MYERS, FL, 33901. It is listed for $829,000 and features 3 beds, 4 baths, and has approximately 3,467 square feet of living space, and was originally constructed in 1924. The current price per square foot is $239. The average price per square foot for Single Family listings in FORT MYERS is $290. The average listing price for Single Family in FORT MYERS is $713,412. To schedule a showing of MLS#2025016791 at 1249 Osceola DR in FORT MYERS, FL, contact your CENTURY 21 Carioti agent at 800-783-8847.
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