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    • 5100 Jessie Harbor Dr

    Osprey, FL 34229

    Apartment building
    2-3 beds
    In-unit laundry (W/D)

    Available units

    This building may have units for rent or for sale. Select a unit to contact.

    What's special

    Panoramic water views

    Facts, features & policies

    Unit features

    Appliances
    • Dishwasher
    • Dryer
    • Range
    • Washer

    Neighborhood: 34229

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    • Beach Access
      Easy coastal access for swimming, sunbathing, and seaside relaxation.
      Outdoor Activities
      Ample parks and spaces for hiking, biking, and active recreation.
      Biking Trails
      Safe, accessible paths for cycling, commuting, and outdoor enjoyment.
      Water Sports
      Opportunities for kayaking, paddleboarding, and aquatic adventures.
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    Anchored by Oscar Scherer State Park and Little Sarasota Bay, Osprey’s 34229 blends relaxed coastal living with nature-forward amenities. Residents bike the Legacy Trail, launch kayaks at Blackburn Point Park, and slip over the historic one‑lane swing bridge to Casey Key for quiet Gulf beaches and sunset views. Culture leans local: the Historic Spanish Point campus of Selby Gardens tells the area’s pioneer story, while waterfront spots like Casey Key Fish House, Rosebud’s Steakhouse, Max’s Table, and The Point keep the dining scene casual but quality, with coffee spots along Tamiami Trail. Daily conveniences include Bay Street Village & Towncenter plus nearby Publix and Walmart Neighborhood Market along Tamiami Trail, with yoga and fitness studios sprinkled around. The vibe is family- and pet-friendly, with mellow nights and bigger-city arts and nightlife an easy drive in Sarasota or Venice. Expect a warm subtropical climate with sea breezes and summer thunderstorms. Recent Zillow market trends show a median asking rent around $3,000, with most listings in the past few months ranging roughly $2,100–$5,000.

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    Areas of interest

    Use our interactive map to explore the neighborhood and see how it matches your interests.

    Travel times

    Walk, Transit & Bike Scores

    22 / 100
    Car-Dependent
    36 / 100
    Somewhat Bikeable

    Nearby schools in Osprey

    GreatSchools rating

    Nearby homes for sale

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    Frequently asked questions

    What is the walk score of 5100 Jessie Harbor Dr?

    5100 Jessie Harbor Dr has a walk score of 22, it's car-dependent.

    What schools are assigned to 5100 Jessie Harbor Dr?

    The schools assigned to 5100 Jessie Harbor Dr include Laurel Nokomis School and Venice Senior High School.

    Does 5100 Jessie Harbor Dr have in-unit laundry?

    Yes, 5100 Jessie Harbor Dr has in-unit laundry for some or all of the units.

    What neighborhood is 5100 Jessie Harbor Dr in?

    5100 Jessie Harbor Dr is in the 34229 neighborhood in Osprey, FL.