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    Islamorada, FL Residential Income Properties for Sale

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    Two Cottages in Islamorada
    $990,000
    1,766 SF

    Two Cottages in Islamorada

    219 Preston St Upper Matecumbe Ky, Islamorada, FL 33036

    Two cottages on one property in the heart of Islamorada.

    • Prime Downtown Islamorada Location: Steps to the ocean, walkable to restaurants, festivals, the Arts District, and key attractions.
    • Two Cottages on One Property: Offers flexibility to live in one and rent the other, or rent both for maximum income.
    • Investment Opportunity: Exceptional investment potential in a highly desirable, walkable area.
    • Versatile Property: Can be used as a single‑family home or a duplex/multifamily property.
    • Cottage Sizes: Front cottage with 2 bedrooms/1 bath (+/- 866 sq. ft.) and back cottage with 2 bedrooms/1 bath (+/- 900 sq. ft.).
    Updated: Jan 16
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    Islamorada Redevelopment Opportunity
    $5,500,000

    Islamorada Redevelopment Opportunity

    82929 Overseas Hwy Upper Matecumbe Ky, Islamorada, FL 33036

    Prime Islamorada property with redevelopment potential in a desirable location.

    • Prime Redevelopment Opportunity: Three parcels zoned Village Center offer broad redevelopment possibilities.
    • 8 Market Rate Development Rights: Islamorada Village Planning Department recognizes 8 development rights.
    • High‑Traffic Location: Situated at the gateway to Islamorada on Overseas Highway.
    • Existing Commercial Building: Includes a 3,312 SF commercial building with attached work yard.
    • Mix of Existing Structures: Currently features mobile homes, apartments, and a commercial building.
    Updated: Oct 16, 2025
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    Based on your search, we've compiled 11 Potential Opportunities for your consideration. Besides 2 Active listings in Islamorada, FL, we suggest exploring several alternatives: 4 properties in Nearby Cities, and similar 2 Off-Market properties to explore as potential leads, plus 3 Land Listings that present a potential for development.

    Explore Opportunities in Nearby Cities

    Here are 4 Similar properties we found in Nearby Locations for your consideration.

    Islamorada Mixed-Use Commercial Property
    $1,899,000

    Islamorada Mixed-Use Commercial Property

    Luxury commercial property with highway frontage and residential unit.

    87847 Overseas Hwy, Plantation Key, FL 33036
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    Waterfront Restaurant & Marina Investment
    $6,999,999

    Waterfront Restaurant & Marina Investment

    Waterfront restaurant, marina, and residential property in Plantation Key, FL.

    90311 Old Hwy, Plantation Key, FL 33070
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    Cozy Studio Apartment in Tavernier
    Contact for pricing
    400 SF

    Cozy Studio Apartment in Tavernier

    Private studio apartment available for rent immediately in Key Largo.

    91865 Overseas Hwy, Key Largo, FL 33070
    View details
    Updated Duplex Near Oceanfront Park
    $829,000
    1,496 SF

    Updated Duplex Near Oceanfront Park

    Legal duplex near Harry Harris Park, updated interiors, strong rental income.

    102 Harry Harris Dr, Key Largo, FL 33070
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    Potential Development Sites for Consideration

    Can't find the perfect fit? These Land listings present an alternative path: the potential to develop a property for your specific goals.

    Important: These AI-suggestions are a starting point, not a guarantee of permitted use. All zoning, permitting, and land use information must be independently verified by you with the appropriate local authorities before making any commitments.

    Islamorada Oceanfront Acreage Opportunity
    $6,750,000

    Islamorada Oceanfront Acreage Opportunity

    7+ acres of pristine upland with 700ft beachfront.

    82900 Old Hwy Upper Matecumbe Ky, Islamorada, FL 33036
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    Islamorada Land with Restaurant/Bar
    $6,995,000

    Islamorada Land with Restaurant/Bar

    Exceptional investment opportunity with restaurant/bar and development potential.

    81910 Overseas Hwy Upper Matecumbe Ky, Islamorada, FL 33036
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    Craig Key Bayfront Legacy Estate
    $10,500,000

    Craig Key Bayfront Legacy Estate

    Rare 1.62-acre bayfront property with deep-water access and dockage.

    72100 Overseas Hwy, Islamorada, FL 33036
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    Explore Off-Market Properties in Islamorada, FL

    Consider similar Off-Market properties in Islamorada, FL. You may contact the owners directly to inquire about their potential intentions to sell. To help you make a strong first impression, we can assist by reaching out to these owners with compelling proposals created using our AI tool.

    207 Russell St

    207 Russell St

    Multifamily properties
    Value Estimation by Request
    207 Russell St, Islamorada, FL 33036
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    Islamorada, FL Residential Income Properties Investment Opportunities Market Analysis

    Explore 3 residential income properties for sale in Islamorada, FL on our real estate platform. These investment opportunities span a total of 8,276 square feet of properties for sale, with an estimated market value of $990,000.

    Prices for residential income properties in Islamorada, FL start at $990,000, averaging $990,000, and reaching up to $990,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you have the most current data.

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    Browse Residential income properties for Sale Near Islamorada, FL

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    Most Searched ZIP Codes in Islamorada, FL

    • 33036

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