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    29 properties
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    Private Triplex with Pool
    Updated: Sep 10
    Private Triplex with Pool

    3476 WINTON Avenue, Sarasota, FL 34234

    $1,300,000
    3,228 sqft 0.63 AC lot
    3 detached single‑family homes on 0.63 acres
    3,228 square feet across the triplex
    Each residence has 3 bedrooms and 2 bathrooms
    Private pool with cabana spaces, fire pit, and outdoor grill
    RTD9 zoning; public water and public sewer
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    Four-Home Quadplex Property
    Updated: Jul 6
    Four-Home Quadplex Property

    1555 7TH Street, Sarasota, FL 34236

    $2,529,000
    3,705 sqft 0.14 AC lot
    Four contiguous properties with four rental homes
    Estimated 23K SF +/- land area
    3,705 square feet of total property size
    DTE zoning in Sarasota’s Rosemary District
    Current annual rentals across all 4 homes
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    Furnished Duplex with Two Residences
    Furnished Duplex with Two Residences

    2245 BAHIA VISTA Street, Sarasota, FL 34239

    $475,000
    1,652 sqft 0.13 AC lot

    Two separately configured homes include private kitchens, living areas, and dining spaces.

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    Furnished Short-Term Rental Property
    Furnished Short-Term Rental Property

    4711 HOLLINGSWORTH AVENUE, Sarasota, FL 34233

    $655,000
    1,696 sqft

    Three separately accessed furnished accommodations are complemented by on-site parking and a landscaped shared rear area.

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    Updated Duplex with Carports
    Updated Duplex with Carports

    12125 MARGARITA Avenue, North Port, FL 34287

    $375,000
    1,585 sqft 0.22 AC lot

    Two remodeled units include private laundry, full kitchens, and separate covered parking.

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    4-Unit Short-Term Rental Portfolio
    4-Unit Short-Term Rental Portfolio

    170 ROOSEVELT Drive, Sarasota, FL 34236

    $1,300,000
    294 sqft 0.90 AC lot

    Updated studio residences with private patios, community pool access, and established beach-oriented operations.

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    Three-Story Mixed-Use Building
    Three-Story Mixed-Use Building

    1345 2ND Street, Sarasota, FL 34236

    $3,750,000
    8,165 sqft 0.12 AC lot

    Downtown property combines a salon-ready first floor, treatment rooms, and a private residential penthouse with elevator access.

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    Duplex with Private Swimming Pool
    Duplex with Private Swimming Pool

    1213 Benedict Ct, Sarasota, FL 34237

    $640,000
    2,610 sqft

    Two separate addresses support a flexible two-unit configuration near Downtown Sarasota.

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    Duplex with Vaulted Lofts
    Duplex with Vaulted Lofts

    418 Narvaezi St, Venice, FL 34285

    $736,900
    2,199 sqft

    Two individually configured units offer flexible occupancy, rental, or personal-use arrangements near Venice Island amenities.

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    Four-Home Rental Portfolio
    Four-Home Rental Portfolio

    1555 7TH STREET, Sarasota, FL 34236

    $2,529,000
    3,705 sqft 0.53 AC lot

    Four contiguous rental homes in the Rosemary District are currently leased on an annual basis.

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    Custom Duplex with Three-Car Garage
    Custom Duplex with Three-Car Garage

    1755 7TH ST, Sarasota, FL 34236

    $1,895,000
    4,400 sqft

    Two independent residences support flexible living arrangements and short-term rental use near downtown Sarasota.

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    Five-Unit Short-Term Rental Building
    Five-Unit Short-Term Rental Building

    1236 13th St, Sarasota, FL 34236

    $1,600,000
    2,832 sqft

    Five-unit multifamily property zoned for short-term rental, with four one-bedroom units and one two-bedroom unit with a den.

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    Five-Bedroom Short-Term Rental With Pool
    Five-Bedroom Short-Term Rental With Pool

    B-6910 Midnight Pass Rd, Sarasota, FL 34242

    $2,895,000
    2,801 sqft

    Vacation rental residence with an elevator, resort-style pool and spa, and indoor-outdoor living areas.

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    Lido Key Income-Producing Portfolio
    Lido Key Income-Producing Portfolio

    170 Roosevelt Dr Unit 10, Sarasota, FL 34236

    $1,300,000
    294 sqft

    Turnkey short-term rental portfolio on South Lido Key.

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    Furnished Duplex with Updated Systems
    Furnished Duplex with Updated Systems

    2245 Bahia Vista St, Sarasota, FL 34239

    $475,000
    1,652 sqft

    Turnkey two-residence property with separate living areas, kitchens, furnishings, and laundry equipment.

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    Income-Generating Duplex With Updated Interiors
    Income-Generating Duplex With Updated Interiors

    993 Gary Street A & B, Sarasota, FL 34234

    $450,000
    1,679 sqft

    Duplex in flood zone X with two 2-bedroom, 1-bath units, screened lanais, private laundry, and covered carports with storage.

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    Updated Duplex Near Warm Springs
    Updated Duplex Near Warm Springs

    12125 Margarita Ave, North Port, FL 34287

    $375,000
    1,585 sqft

    Updated duplex with strong rental potential near Warm Mineral Springs.

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    Updated Short-Term Rental Portfolio
    Updated Short-Term Rental Portfolio

    10-170 Roosevelt Dr, Sarasota, FL 34236

    $1,300,000
    294 sqft

    Four studio condominiums offer managed vacation-rental operations, private patios, and access to a shared pool near the beach.

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    Duplex with Private Pools
    Duplex with Private Pools

    2125 Montclair Drive, Sarasota, FL 34231

    Contact for pricing
    5,682 sqft

    Two masonry, two-story 3BR/2.5BA units, each with screened patio, private yard, and separately metered utilities.

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    Three-Home Multifamily Property
    Three-Home Multifamily Property

    3476 WINTON, Sarasota, FL 34234

    $1,300,000

    Three detached residences share a pool and cabana setting with active rental use.

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    Mixed-Use Building with Penthouse
    Mixed-Use Building with Penthouse

    1345 2ND, Sarasota, FL 34236

    $3,750,000

    Commercial treatment space occupies the lower levels, with a four-bedroom residence above.

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    Remodeled Duplex with Furnishings
    Remodeled Duplex with Furnishings

    974 TENNESSEE LANE, Sarasota, FL 34234

    $549,000
    1,200 sqft

    Two furnished one-bedroom units offer patios, updated systems, and flexible short-term or annual rental use.

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    21-Unit Hotel with Swimming Pool
    21-Unit Hotel with Swimming Pool

    340 S Tamiami Trail, Venice, FL 34285

    Contact for pricing
    5,915 sqft

    Three single-story buildings offer a varied room mix, guest laundry, and updated roofing.

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    Furnished Two-Bedroom Vacation Rental Condo
    Furnished Two-Bedroom Vacation Rental Condo

    5673 MIDNIGHT PASS RD #202, Sarasota, FL 34242

    $479,999

    The residence includes a primary suite, guest bedroom, covered parking and access to a heated community pool and boat dock.

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    Sarasota County, FL Short Term Rental Properties Market Trends and Statistics

    Explore 29 short term rental properties for sale in Sarasota County, FL, showcased through 29 active listings on our real estate platform. These investment opportunities span a total of 59,281 square feet of properties for sale, with an estimated market value of $33,206,899.

    Sale prices for short term rental properties in Sarasota County, FL start at $375,000, averaging $1,277,188, and reaching up to $3,750,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you stay ahead with the latest data and market trends.

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    Featured Sarasota County Real Estate Agencies

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

    Anytime Realty
    2563 N. Toledo Blade Blvd #3 North Port, FL 34288
    Phone: 19417301247
    www.AnytimeRealtyFlorida.com
    Realty by Dale Thomas
    3941 Santa Ana Rd North Port, FL 34286
    Phone: 19412667906
    www.realestatebydalethomas.com
    Gulf Shores Realty
    211 Tamiami Trail S. Venice, FL 34285
    Phone: 19414886644
    gulfshoresrealty.com
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