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  • Price cut: $76K (7/29)
    $999,000

    1357 Osceola Dr, Fort Myers, FL 33901

    5beds
    3,928sqft
    : 
    $6,369/mo
    Get pre-qualified
    Single Family Residence
    Built in 2000
    0.64 Acres Lot
    $958,200 Zestimate®
    $254/sqft
    $-- HOA

    What's special

    Detached garageThree-and-a-half bathroomsFive bedroomsThree spacious bedroomsCharming front porchEnormous outdoor living spaceGlass-front cabinetry
    Highly motivated sellers! Welcome to this fabulous estate home located in one of the area’s most sought-after neighborhoods, just moments from the historic Edison & Ford Winter Estates. Located one block from the beautiful Caloosahatchee River. Situated outside of a designated flood zone, this property offers the added peace of mind and convenience of no required flood insurance. NO FLOOD ZONE! This expansive residence offers over 3,900 square feet of living space with five bedrooms and three-and-a-half bathrooms, designed perfectly for a large family or anyone who loves to entertain. As you enter through the elegant French glass front doors from the charming front porch, you are welcomed by a spacious and inviting layout. To the right, you’ll find a beautiful formal living room or den, while the left side features an elegant dining room perfect for gatherings and holiday dinners. The heart of the home is the stunning open-concept kitchen, showcasing glass-front cabinetry, beautiful appliances, and generous space for entertaining, all flowing seamlessly into the oversized family room. The split floor plan offers privacy and functionality. On the right side of the home, you’ll find three spacious bedrooms and two full bathrooms. On the opposite wing, the luxurious primary suite features a cozy double-sided fireplace connecting the bedroom and spa-inspired bathroom, complete with a soaking tub and separate shower. The primary suite also offers direct access to the pool area. An additional bedroom and bathroom are also located on this side of the home. Step outside to your enormous outdoor living space, featuring a sparkling pool surrounded by beautiful travertine tile, creating the perfect Florida retreat for relaxing or entertaining guests. The property also includes a detached garage with endless possibilities—ideal for a mother-in-law suite conversion, private guest retreat, antique car storage, or whatever your vision may be. An additional flex space currently serves as an impressive home gym but could easily be transformed into a studio, office, or recreational area. Additional highlights include gorgeous oak and tile flooring throughout, breathtaking mature oak trees in the front yard, and an unbeatable location just minutes from Downtown Fort Myers dining, shopping, and entertainment. Located just minutes from Downtown Fort Myers, you’ll enjoy quick access to waterfront dining, live music, shopping, breweries, art walks, and community events. Spend weekends exploring the River District, catching sunsets along the water, visiting nearby marinas, or taking a short drive to Southwest Florida’s beautiful beaches, golf courses, and nature preserves. Rarely does a home combine this much space, versatility, charm, and location in one extraordinary package. This is more than just a home—it’s a lifestyle opportunity to experience the very best of Southwest Florida living.
    69 days
    |
    542
    |
    26
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    Zillow last checked:

    Listing updated:

    Listed by:

    Tara Krueger-Rose 239-265-1739,

    RE/MAX Trend

    Source: Florida Gulf Coast MLS,MLS#: 2026022632MLS LogoOriginating MLS: Florida Gulf Coast

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 5
      • Bathrooms: 4
      • Full bathrooms: 3
      • 1/2 bathrooms: 1
      Rooms
      • Room types: Bathroom, Den, Exercise Room, Family Room, Guest Quarters, Office, Screened Porch, Great Room
      Heating
      • Central, Electric
      Cooling
      • Central Air, Ceiling Fan(s), Electric
      Appliances
      • Included: Cooktop, Dryer, Dishwasher, Electric Cooktop, Disposal, Ice Maker, Refrigerator, RefrigeratorWithIce Maker, Separate Ice Machine, Trash Compactor, Washer
      • Laundry: Inside, Laundry Tub
      Features
      • Breakfast Bar, Built-in Features, Breakfast Area, Tray Ceiling(s), Separate/Formal Dining Room, Dual Sinks, Entrance Foyer, Eat-in Kitchen, Family/Dining Room, French Door(s)/Atrium Door(s), Fireplace, Jetted Tub, Kitchen Island, Living/Dining Room, Multiple Shower Heads, Pantry, Cable TV, Walk-In Pantry, Walk-In Closet(s), High Speed Internet, Home Office, Bathroom, Den, Exercise Room, Family Room, Guest Quarters, Office, Screened Porch, Great Room
      • Flooring: Carpet, Tile, Wood
      • Doors: French Doors
      • Windows: Single Hung, Shutters
      • Has fireplace: Yes
      Interior area
      • Total structure area: 8,377
      • Total interior livable area: 3,928 sqft
      Video & virtual tour

      Property

      Parking
      • Total spaces: 3
      • Parking features: Detached, Garage, Detached Carport, Garage Door Opener
      • Garage spaces: 2
      • Carport spaces: 1
      • Covered spaces: 3
      Features
      • Stories: 1
      • Patio & porch: Balcony, Lanai, Open, Patio, Porch, Screened
      • Exterior features: Fire Pit, None, Patio, Storage
      • Has private pool: Yes
      • Pool features: In Ground
      • Has view: Yes
      • View description: Landscaped
      • Waterfront features: None, Across the Road Water Frontage
      Lot
      • Size: 0.64 Acres
      • Dimensions: 195 x 182 x 139 x 161
      • Features: Multiple lots
      Details
      • Parcel number: 264424P40290D.0080
      • Lease amount: $0
      • Zoning description: RS-5

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Ranch,One Story
      • Property subtype: Single Family Residence
      Materials
      • Block, Concrete, Stucco
      • Roof: Shingle
      Condition
      • Resale
      • Year built: 2000

      Utilities & green energy

      • Sewer: Assessment Paid, Public Sewer
      • Water: Assessment Paid, Public
      • Utilities for property: Cable Available

      Community & HOA

      Community
      • Features: Non-Gated
      • Security: Smoke Detector(s)
      • Condo and coop fee: $0
      • Membership fee: $0
      • Subdivision: RIVERSIDE
      HOA
      • Has HOA: No
      • Amenities included: Fitness Center, Guest Suites, Hobby Room, Storage
      • Services included: None
      Location
      • Region: Fort Myers

      Financial & listing details

      • Price per square foot: $254/sqft
      • Tax assessed value: $960,109
      • Annual tax amount: $10,915
      • Date on market: 5/28/2026
      • Cumulative days on market: 70 days
      • Listing terms: All Financing Considered,Cash
      • Ownership: Single Family

        Estimated market value

        $958,200

        $910,000 - $1.01M

        $4,672/mo

        Price history

        DateEventPrice
        7/29/2026Price change$999,000-7.1%$254/sqft
        Source: Florida Gulf Coast MLS #2026022632 Report a problem
        6/16/2026Price change$1,075,000-6.5%$274/sqft
        Source: Florida Gulf Coast MLS #2026022632 Report a problem
        5/28/2026Listed for sale$1,150,000-4.2%$293/sqft
        Source: Florida Gulf Coast MLS #2026022632 Report a problem
        11/24/2025Listing removed$1,200,000$305/sqft
        Source: Florida Gulf Coast MLS #225049430 Report a problem
        5/30/2025Listed for sale$1,200,000-11.1%$305/sqft
        Source: SWFLMLS #225049430 Report a problem
        10/23/2024Listing removed$1,350,333$344/sqft
        Source: SWFLMLS #224038503 Report a problem
        8/29/2024Price change$1,350,333-15.1%$344/sqft
        Source: SWFLMLS #224038503 Report a problem
        8/12/2024Price change$1,590,444-3.6%$405/sqft
        Source: SWFLMLS #224038503 Report a problem
        4/30/2024Listed for sale$1,649,222+43.4%$420/sqft
        Source: SWFLMLS #224038503 Report a problem
        9/30/2022Listing removed--
        Source: BeachesMLS #F10313085 Report a problem
        1/5/2022Price change$1,150,000-4.2%$293/sqft
        Source: Florida Gulf Coast MLS #221079606 Report a problem
        11/17/2021Listed for sale$1,200,000+1400%$305/sqft
        Source: Florida Gulf Coast MLS #221079606 Report a problem
        6/2/1999Sold$80,000$20/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$10,916 +2%$636,802 +2.9%
        2024$10,697 +1.6%$618,855 +3%
        2023$10,525 +0.5%$600,830 +3%
        2022$10,473 -2.1%$583,330 +3%
        2021$10,701 -1.2%$566,340 +1.4%
        2020$10,835 +0.5%$558,521 -32.4%
        2019$10,783 $826,059 +54.2%
        2018$10,783 -0.4%$535,784 +2.1%
        2017$10,823 +0.4%$524,764 -40.4%
        2016$10,775 +1.3%$880,773 +14.7%
        2015$10,642 -0.7%$767,714 -2%
        2014$10,712 +1%$783,504 +25.1%
        2013$10,605 +6.6%$626,519 -7.5%
        2012$9,951 +3.5%$677,505 +33%
        2011$9,617 +0%$509,215 +8.5%
        2010$9,615 +8.7%$469,200 -14.1%
        2009$8,846 +4.9%$545,970 -12.6%
        2008$8,432 +3.2%$624,720 -6.7%
        2007$8,172 +3%$669,710 +11.3%
        2006$7,934 -5.5%$601,730 +51.5%
        2004$8,398 -3.6%$397,210 +3.2%
        2003$8,711 +82%$384,940 +92.3%
        2002$4,786 $200,190 +22.5%
        2000-- $163,460
        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

        15 / 100
        Car-Dependent
        34 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

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