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Active
    • Price increase: $52K (5/27)
    $881,000

    1249 Osceola Dr, Fort Myers, FL 33901

    3beds
    3,467sqft
    : 
    $5,617/mo
    Get pre-qualified
    Single Family Residence
    Built in 1924
    0.29 Acres Lot
    $-- Zestimate®
    $254/sqft
    $-- HOA

    What's special

    Pet friendly sidewalksUpdated electrical and plumbingKid friendly sidewalksHistoric home
    Two houses for the price of one. Old homes are unique, full of charm and history. This historic home checks all the boxes, and one the best locations as well as close to downtown, schools, hospitals, kept mostly original to its original build, with updated electrical and plumbing, roof is only 3 years old. Never any flooding from any hurricanes in 22 years of ownership. In a neighborhood known for its close-knit neighbors, kid friendly sidewalks, pet friendly sidewalks, almost Norman Rockwell like neighborhood. With a multi-family designation, the super cute guest house has many possibilities or a rental? 3-bedroom main house, and a 1-bedroom guest house. Two car garage with plenty of room to store a boat or RV. Remember this is a 100-year-old home, antique homes are known for lack of closet space, kitchen is outdated as well, all bedrooms are upstairs. Tremendous possibilities or keep as is. If you like historic old homes, this is the one. Home is featured in Pam Miners book 'River & Road' Fort Myers Architecture from Craftsman to Modern. Chapter One. This is a unique home for that unique buyer. Location, location
    5 days
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    17
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    Zillow last checked:

    Listing updated:

    Listed by:

    Cliff Glansen 954-965-3990,

    Flatfee.com

    Source: Florida Gulf Coast MLS,MLS#: 2025016791MLS LogoOriginating MLS: Florida Gulf Coast

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 3
      • Bathrooms: 4
      • Full bathrooms: 4
      Heating
      • Central, Electric
      Cooling
      • Central Air, Electric
      Appliances
      • Included: Dryer, Dishwasher, Microwave, Range, Refrigerator, Washer
      • Laundry: In Garage
      Features
      • Living/Dining Room, Other, Tub Shower, Split Bedrooms
      • Flooring: Wood
      Interior area
      • Total structure area: 3,467
      • Total interior livable area: 3,467 sqft
      Video & virtual tour

      Property

      Parking
      • Total spaces: 2
      • Parking features: Detached, Garage, Two Spaces, Garage Door Opener
      • Garage spaces: 2
      Features
      • Levels: Two
      • Stories: 2
      • Patio & porch: Deck
      • Exterior features: Deck, Fence, None, Awning(s)
      • Waterfront features: None
      Lot
      • Size: 0.29 Acres
      • Dimensions: 154 x 81 x 81 x 154
      • Features: Rectangular Lot
      Details
      • Parcel number: 264424P40290C.0170
      • Lease amount: $0
      • Zoning description: RS-5

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Two Story
      • Property subtype: Single Family Residence
      Materials
      • Brick, Block, Concrete, Wood Frame
      • Roof: Shingle
      Condition
      • Resale
      • Year built: 1924

      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: $254/sqft
      • Tax assessed value: $620,391
      • Annual tax amount: $5,323
      • Date on market: 10/24/2025
      • Cumulative days on market: 284 days
      • Listing terms: All Financing Considered,Cash,FHA,VA Loan
      • Ownership: Single Family
      • Road surface type: Paved

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        5/27/2026Price change$881,000+6.3%$254/sqft
        Source: Florida Gulf Coast MLS #2025016791 Report a problem
        4/16/2026Price change$829,000-0.2%$239/sqft
        Source: Florida Gulf Coast MLS #2025016791 Report a problem
        4/1/2026Price change$831,000-0.5%$240/sqft
        Source: Florida Gulf Coast MLS #2025016791 Report a problem
        3/20/2026Price change$835,000-0.5%$241/sqft
        Source: Florida Gulf Coast MLS #2025016791 Report a problem
        3/10/2026Price change$839,000-1.2%$242/sqft
        Source: Florida Gulf Coast MLS #2025016791 Report a problem
        1/5/2026Price change$849,000-1.2%$245/sqft
        Source: Florida Gulf Coast MLS #2025016791 Report a problem
        12/12/2025Price change$859,000+0.7%$248/sqft
        Source: Florida Gulf Coast MLS #2025016791 Report a problem
        6/13/2025Price change$853,000-0.7%$246/sqft
        Source: SWFLMLS #225002680 Report a problem
        6/10/2025Price change$859,000-1.2%$248/sqft
        Source: SWFLMLS #225002680 Report a problem
        4/4/2025Price change$869,000-2.3%$251/sqft
        Source: SWFLMLS #225002680 Report a problem
        3/26/2025Price change$889,500+1.1%$257/sqft
        Source: SWFLMLS #225002680 Report a problem
        2/19/2025Price change$879,500-1.1%$254/sqft
        Source: SWFLMLS #225002680 Report a problem
        1/8/2025Listed for sale$889,000+0.2%$256/sqft
        Source: SWFLMLS #225002680 Report a problem
        11/20/2024Listing removed$887,500-0.7%$256/sqft
        Source: SWFLMLS #224047557 Report a problem
        11/15/2024Price change$893,500-0.2%$258/sqft
        Source: SWFLMLS #224047557 Report a problem
        11/8/2024Price change$895,000-0.4%$258/sqft
        Source: SWFLMLS #224047557 Report a problem
        10/28/2024Price change$898,500+0.1%$259/sqft
        Source: SWFLMLS #224047557 Report a problem
        10/10/2024Price change$897,500+0.1%$259/sqft
        Source: SWFLMLS #224047557 Report a problem
        9/7/2024Price change$896,500+0.1%$259/sqft
        Source: SWFLMLS #224047557 Report a problem
        8/7/2024Price change$895,500+0.1%$258/sqft
        Source: SWFLMLS #224047557 Report a problem
        7/17/2024Price change$895,000+0.1%$258/sqft
        Source: SWFLMLS #224047557 Report a problem
        6/29/2024Price change$894,500-0.1%$258/sqft
        Source: SWFLMLS #224047557 Report a problem
        6/20/2024Price change$895,050-0.1%$258/sqft
        Source: SWFLMLS #224047557 Report a problem
        5/30/2024Listed for sale$895,500+44.9%$258/sqft
        Source: SWFLMLS #224047557 Report a problem
        5/28/2024Listing removed--
        Source: SWFLMLS #223067125 Report a problem
        9/16/2005Sold$618,000$178/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$5,546 +1.9%$316,738 +2.9%
        2024$5,440 +2.2%$307,811 +3%
        2023$5,323 +0.5%$298,846 +3%
        2022$5,295 -1.1%$290,142 +3%
        2021$5,356 +2.2%$281,691 +1.4%
        2020$5,240 +0.8%$277,802 -36.6%
        2019$5,200 $438,470 +64.5%
        2018$5,200 -0.2%$266,493 +2.1%
        2017$5,211 +1.2%$261,012 -38.7%
        2014$5,147 $425,836
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

        Explore the cost of this home by adjusting the details. Changes won't be saved.
        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.
        See how much you could borrow to make a competitive offer.
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        Climate risks

        Neighborhood: 33901

        Getting around

        12 / 100
        Car-Dependent
        31 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: ALLEN PARK
        • Middle: FORT MYERS
        • High: FORT MYERS

        Source: Florida Gulf Coast MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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