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  • $1,354,000

    1248 Osceola Dr, Fort Myers, FL 33901

    6beds
    3,582sqft
    : 
    $8,378/mo
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    Single Family Residence
    Built in 1925
    0.49 Acres Lot
    $-- Zestimate®
    $378/sqft
    $-- HOA

    What's special

    Center islandCharming private courtyardRecessed ovenBright inviting family roomExpansive kitchenRestored hardwood floorsOversized pool
    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.
    181 days
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    382
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    13
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    Zillow last checked:

    Listing updated:

    Listed by:

    Mark Hetrick 239-826-8037,

    List In MLS Realty, LLC

    Source: Florida Gulf Coast MLS,MLS#: 2026006878MLS LogoOriginating MLS: Florida Gulf Coast

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 6
      • Bathrooms: 3
      • Full bathrooms: 3
      Rooms
      • Room types: Den, Family Room, Office, Screened Porch
      Heating
      • Central, Electric
      Cooling
      • Central Air, Ceiling Fan(s), Electric
      Appliances
      • Included: Built-In Oven, Dishwasher, Disposal, Self Cleaning Oven, Warming Drawer
      • Laundry: Washer Hookup, Dryer Hookup, Inside, In Garage
      Features
      • Bedroom 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, Den, Family Room, Office, Screened Porch
      • Flooring: Tile, Wood
      • Doors: French Doors
      • Windows: Single Hung
      • Has fireplace: Yes
      Interior area
      • Total structure area: 4,352
      • Total interior livable area: 3,582 sqft
      Video & virtual tour

      Property

      Parking
      • Total spaces: 3
      • Parking features: Driveway, Detached, Garage, Paved, RV Access/Parking, Two Spaces, Garage Door Opener
      • Garage spaces: 3
      • Has uncovered spaces: Yes
      Features
      • Levels: Two
      • Stories: 2
      • Patio & porch: Lanai, Patio, Porch, Screened
      • Exterior features: Fence, None, Patio
      • Has private pool: Yes
      • Pool features: Concrete, Electric Heat, Heated, In Ground, Pool Equipment, Screen Enclosure
      • Has view: Yes
      • View description: Landscaped
      • Waterfront features: None
      Lot
      • Size: 0.49 Acres
      • Dimensions: 120 x 175 x 121 x 181
      • Features: Rectangular Lot
      Details
      • Additional structures: Gazebo
      • Parcel number: 264424P40290G.0030
      • Lease amount: $0
      • Zoning description: RS-5

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Two Story
      • Property subtype: Single Family Residence
      Materials
      • Block, Concrete, Stucco
      • Roof: Tile
      Condition
      • Resale
      • Year built: 1925

      Utilities & green energy

      • Sewer: Public Sewer
      • Water: Public
      • Utilities for property: Cable Available

      Community & HOA

      Community
      • Features: Non-Gated
      • Condo and coop fee: $0
      • Membership fee: $0
      • Subdivision: RIVERSIDE
      HOA
      • Has HOA: No
      • Amenities included: None
      • Services included: None
      Location
      • Region: Fort Myers

      Financial & listing details

      • Price per square foot: $378/sqft
      • Tax assessed value: $764,966
      • Annual tax amount: $12,200
      • Date on market: 2/8/2026
      • Cumulative days on market: 182 days
      • Listing terms: All Financing Considered,Cash,Owner May Carry,Owner May CarrySecond
      • Ownership: Single Family
      • Road surface type: Paved

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        5/8/2026Price change$1,354,000+0.3%$378/sqft
        Source: Florida Gulf Coast MLS #2026006878 Report a problem
        2/8/2026Listed for sale$1,350,000-10%$377/sqft
        Source: Florida Gulf Coast MLS #2026006878 Report a problem
        6/5/2025Listing removed$1,500,000$419/sqft
        Source: SWFLMLS #224049313 Report a problem
        6/6/2024Listed for sale$1,500,000+141.9%$419/sqft
        Source: SWFLMLS #224049313 Report a problem
        1/20/2021Sold$620,000-11.3%$173/sqft
        Source: Public Record Report a problem
        1/2/2021Pending sale$699,000$195/sqft
        Source: Compass Florida LLC #220057060 Report a problem
        10/10/2020Price change$699,000+2.8%$195/sqft
        Source: Compass Florida LLC #220057060 Report a problem
        9/30/2020Listed for sale$679,900$190/sqft
        Source: Compass Florida LLC #220057060 Report a problem
        9/27/2020Pending sale$679,900$190/sqft
        Source: Compass Florida LLC #220057060 Report a problem
        9/17/2020Listed for sale$679,900$190/sqft
        Source: Compass Florida LLC #220057060 Report a problem
        3/20/2020Listing removed$679,900$190/sqft
        Source: Riverside Realty Group, LLC #220002247 Report a problem
        6/14/2019Listed for sale$679,900+49.4%$190/sqft
        Source: Riverside Realty Group, LLC #219042010 Report a problem
        10/22/2013Sold$455,000$127/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$12,200 +1.6%$704,011 +2.9%
        2024$12,008 +1.5%$684,170 +3%
        2023$11,835 +0.5%$664,243 +3%
        2022$11,779 +6.2%$644,896
        2021$11,095 +3.1%--
        2020$10,763 -2.6%$507,926 -1.1%
        2019$11,052 $513,583 -0.3%
        2018$11,052 -2.5%$515,179 -0.3%
        2017$11,330 -2.3%$516,787 -0.2%
        2016$11,600 +1.9%$517,992 +16.2%
        2015$11,379 +10.2%$445,887 +5%
        2014$10,329 +5%$424,521 +32.9%
        2013$9,836 +92%$319,392 +24.7%
        2012$5,124 -6.3%$256,172 -5.9%
        2011$5,470 -1%$272,302 -13.2%
        2010$5,524 +0.2%$313,854 -24.7%
        2009$5,514 -7.9%$416,530 -21.2%
        2007$5,989 -11%$528,280 +6.2%
        2006$6,727 +19.7%$497,670 +63.9%
        2004$5,618 -1.5%$303,560 +6.5%
        2003$5,705 +12.2%$285,020 +12%
        2002$5,084 $254,520 +11.6%
        2000-- $228,050
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

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        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
        Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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        Climate risks

        Neighborhood: 33901

        Getting around

        8 / 100
        Car-Dependent
        30 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

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