Features & Amenities

Interior

  • Other Interior Features

    Eat-in Kitchen, Open Floorplan, Stone Counters, Walk-In Closet(s)

  • Total Bedrooms

    2

  • Bathrooms

    2

  • Cooling YN

    YES

  • Cooling

    Central Air

  • Fireplace YN

    NO

  • Heating YN

    YES

  • Heating

    Electric

  • Pet friendly

    No

Exterior

  • Garage

    No

  • Other Exterior Features

    Lighting, Outdoor Grill, Rain Gutters, Storage, Tennis Court(s)

  • Parking

    Covered, Driveway, Guest

  • Patio and Porch Features

    Patio

  • Pool

    Yes

  • Pool Features

    Heated, In Ground

  • Waterfront YN

    NO

  • View

    Water

Area & Lot

  • Lot Features

    Cul-De-Sac, Landscaped, Level, Near Golf Course, Near Public Transit, Private, Paved

  • Lot Size(acres)

    26.67

  • Property Type

    Residential Lease

  • Property Sub Type

    Townhouse

Price

  • Sales Price

    $7,000

  • Sq. Footage

    1, 256

  • Price/SqFt

    $5

HOA

  • Association

    Yes

  • Association Fee Includes

    N/A

School District

  • Elementary School

    Anna Maria Elementary

  • Middle School

    Martha B. King Middle

  • High School

    Bayshore High

Property Features

  • Stories

    1

  • Association Amenities

    Trail(s)

  • Senior Community YN

    NO

  • Sewer

    Public Sewer

  • Water Source

    Public

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Location

County

Manatee

Elementary School

Anna Maria Elementary

Middle School

Martha B. King Middle

High School

Bayshore High

Listing Courtesy of Debby McCaig , COLDWELL BANKER REALTY

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Looking for the perfect vacation getaway? Lucky you! This stunning, light-filled end-unit beach and bay villa is now available for January and February 2026! An opportunity that won’t last long. Enjoy views of unforgettable morning sunrises on Sarasota Bay and breathtaking Gulf Sunsets directly across the street, with three beach access points — including private deeded beach access. Appreciate the convenience of pulling directly into your private carport with no steps or elevators and relish the peace and privacy of having no neighbors above or below during your stay. This beautifully appointed coastal villa features two bedrooms, two bathrooms, a spacious open concept living area, and an opulent interior design that is soaked in sunlight. The brand new remodeled and fully equipped kitchen is ideal for preparing meals with fresh local ingredients from nearby farmers' markets or head out to dine at one of the delectable nearby restaurants. Windward Bay is a low-density, wildlife-rich community nestled mid-Longboat Key on 26 acres, offering resort-style amenities including two heated pools, two tennis/pickleball courts, two marinas, kayak racks, shuffleboard, a clubhouse with kitchen, library, fitness room, two saunas, and multiple fire pits and barbecue areas throughout the property. Enjoy half a mile of scenic waterfront trails and direct access to the Gulf or Bay for boating, fishing, or simply soaking up the sun. Located just minutes from Downtown Sarasota, St. Armands Circle, Bridge Street, Historic Cortez Fishing Village, championship golf courses, shopping, dining, and vibrant cultural attractions. This is a rare opportunity to create lasting memories in a home that guests return to year after year. This villa is more than a vacation rental — it’s a tradition. One couple has returned every March and April for over a decade, drawn by the comfort, beauty, and unbeatable location.

4780 GULF OF MEXICO DR. VILLA 5

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