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    Summerland Key, FL
    Short Term Rental

    Summerland Key, FL Short Term Rental Properties for Sale

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    Cudjoe Key, FL Big Pine Key, FL Key West, FL Stock Island, FL Marathon, FL Conch Key, FL
    Oceanfront Resort Residence Portfolio
    Updated: Oct 13, 2025
    Oceanfront Resort Residence Portfolio

    231 E Shore Dr, Summerland Key, FL 33042

    Contact for pricing
    4,200 sqft
    Seven newly constructed oceanfront residences on the Atlantic in Summerland Key within a gated enclave
    Each residence offers 5 bedrooms, 5.5 baths, and over 4,000 SF, plus a private infinity pool and rooftop deck
    Assigned dockage with direct ocean access for every home; dockage is first come, first served for boats up to 40 ft
    No rental restrictions, allowing short‑term rental/STR and Airbnb use
    Shared resort‑style amenities include a private boat basin, pickleball and sport courts, paddleboard launch, and hammock lounge zones
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    See what stands out in Monroe County

    We check every for-sale listing in the county against comparable properties across the country. Most price about where you would expect. A few are worth a second look.

    We check every listing here. A few are worth a second look.

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    Based on your search, we've compiled 5 Potential Opportunities for your consideration. Besides 1 Active listings in Summerland Key, FL, we suggest exploring several alternatives: 4 properties in Nearby Cities

    Opportunities in Nearby Cities

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

    Waterfront Condominium Development
    Waterfront Condominium Development

    1 Kyle Way S, Marathon, FL 33050

    Contact for pricing

    Pre-construction waterfront condos in Marathon offer deeded boat slips and deeded transient rental licenses with nightly rental allowance.

    View details
    Waterfront Houseboat Rental Property
    Waterfront Houseboat Rental Property

    Rat Key Street Gulf, Key West, FL 33040

    $850,000

    Includes two custom-built houseboats operated as short-term rentals alongside guided eco tours and private charter services.

    View details
    Charter Marina Business
    Charter Marina Business

    1 Boat Rental Business, Key West, FL 33040

    $150,000

    Marine business with charter vessels, transferable wet slips, and an established short-term rental operation.

    View details
    Waterfront Short-Term Rental Community
    Waterfront Short-Term Rental Community

    2264 Overseas Hwy # 8, Marathon, FL 33050

    Contact for pricing

    Individual homes feature private pools, guest laundry, dock access, covered parking, and ocean-view balconies.

    View details

    Summerland Key, FL Short Term Rental Properties Market Trends and Statistics

    Explore 1 short term rental properties for sale in Summerland Key, FL on our real estate platform. These investment opportunities span a total of 4,200 square feet of properties for sale.

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    Top Commercial Asset Segments

    Commercial property segments ranked by active listings on the market

    Short term rental properties 1

    Demographics Overview

    Population 11K
    Population Growth (5Y) -1.0%
    Median Household Income $98,106
    College Educated 49.5%

    Taxes & Financing

    Tax Rate (average for all types) 0.81%
    Property Tax per SF $12.32 per SF
    Tax Rate vs County Average 0.07 pp above county avg
    Average Loan-to-Value 65.0%

    Listings Trend

    New vs delisted commercial listings in Monroe County

    New Delisted

    Total CRE Inventory on Market (SF)

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