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    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
    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
    View details
    Realmo Analytics Monitor Off-market properties and contact owners who are ready to sell. Many signals applied to make quality leads for you. Get Leads
    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 Duplex with Private Pool
    Waterfront Duplex with Private Pool

    219 Sombrero Beach Road, Marathon, FL 33050

    $1,395,000
    1,840 sqft 0.16 AC lot

    Waterfront residence with private dockage, beach access, and a four-bedroom, three-bath configuration.

    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
    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
    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

    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)

    Average Property Price per SF

    For-sale Residential Income pricing trends in Monroe County

    Residential Income

    How Realmo verifies these figures

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    • 33042

    Featured Summerland Key Real Estate Agencies

    Realmo connects you with licensed Summerland Key CRE brokers providing property specifications, local market pricing, and commercial transaction underwriting support.

    Internet Realty/Florida Keys Inc (KW)
    24752 Overseas Hwy Summerland Key, FL
    Phone: (305) 745-9088
    www.
    Island Welcome Real Estate LLC
    24437 Overseas Hwy Summerland Key, FL
    Phone: (305) 923-9161
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