Single Family Residence at 5140 WINDWARD AVE, SARASOTA
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$1,650,000

5140 WINDWARD AVE
SARASOTA, FL 34242
Listed by Judie Berger · PREMIER SOTHEBY'S INTERNATIONAL REALTY
Bedrooms
3
Bathrooms
2.5
Living area
2,308 sqft
Year built
1963

About this home

An Exceptional Opportunity for Waterfront Living. Discover a private waterfront retreat where boating, tropical gardens, and relaxed island living come together in one of Siesta Key's desirable residential neighborhoods. Set behind a gated entrance and surrounded by lush landscaping, this beautifully refreshed three-bedroom, two-and-a-half-bath residence offers an inviting blend of coastal comfort, privacy, and exceptional outdoor living. Designed to embrace the Florida lifestyle, the spacious, open living and dining areas feature easy-care tile flooring, abundant natural light, and effortless connections to the outdoors. The updated kitchen offers granite countertops, white cabinetry, stainless steel appliances, and a welcoming dining area overlooking the pool and gardens. The comfortable primary suite and two additional bedrooms provide flexibility for family, guests, or a home office. A distinctive Bali-inspired bath with an indoor-outdoor shower adds an unexpected touch of tropical character. The heart of this property is its extraordinary screened outdoor living area. An expansive swimming pool and elevated spa are surrounded by generous paver decking, multiple lounging and dining spaces, and a covered lanai, creating a wonderful setting for entertaining or simply enjoying the island breezes. Beyond the pool, a beautifully landscaped backyard unfolds toward the waterfront, offering a peaceful garden setting with mature palms, tropical foliage, and room to relax. For boating enthusiasts, the private dock and 7,000 lb. boat lift provide convenient access to Sarasota Bay, the Intracoastal Waterway, and the Gulf beyond. Spend the morning cruising the waterways, enjoy an afternoon on the water, or launch a kayak or paddleboard right from your backyard. A welcoming covered entry, gated paver driveway, and attached two-car garage with additional storage complete this distinctive island property. Just minutes from Siesta Beach's renowned quartz-white sands, Siesta Village's restaurants and boutiques, and the cultural attractions of downtown Sarasota, this residence delivers the best of coastal living in a wonderfully private setting. Whether entertaining around the pool, exploring Sarasota's waterways, or simply enjoying the tranquility of your own tropical gardens, this is an opportunity to embrace the Siesta Key lifestyle

Highlights

WaterfrontPrivate pool

Property details

MLS
Stellar MLS
MLS #
MFRA4708132
Property type
Single Family Residence
Subdivision
LOT 5 SARA SANDS UNIT 1
Status
Active
Days on market
N/A
On market date
October 23, 2026
Stories
N/A
Total bathrooms
2.5
Garage spaces
2
Parking spaces
N/A
Lot size
0.34 acres
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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card.

Elementary
PHILLIPPI SHORES ELEMENTARY SCHOOL
2.09 mi away · Grades -1-5
Nearest school -- attendance-zone data not available here
4.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
763
Student:teacher ratio
15.0:1
District
SARASOTA
Middle
BROOKSIDE MIDDLE SCHOOL
2.71 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
3.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
760
Student:teacher ratio
15.8:1
District
SARASOTA
High
RIVERVIEW HIGH SCHOOL
2.54 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
2.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
2,542
Student:teacher ratio
20.7:1
District
SARASOTA

Walkability

Blended score for SARASOTA's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

73
Walkable
out of 100
EPA National Walkability Index
14.2 / 20 -- Above average walkable
Google Places amenity density
75 / 100
Restaurants & cafes20
Grocery stores2
Parks7
Schools2
Transit stops13
Pharmacies0

Market position

How this listing compares to current activity in SARASOTA, from live MLS data.

On the market 0 days -- 168 fewer days than SARASOTA's current average of 168 days.
For reference, the median list price across 4,720 active listings in SARASOTA right now is $365,000.

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

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Est. monthly payment
$10,086/mo
$330,000 down
$1,320,000 loan
Principal & interest$8,561
Property tax (est.)$1,375
Home insurance (est.)$150

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Data source: Listing information provided by Stellar MLS (mfrmls) via Trestle/CoreLogic. Last updated 19 hr ago.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.