# 102 WINDWARD Drive, Osprey, FL 34229 > **TL;DR:** 3bd/3ba single family, $1,047,000 ($491/sqft), built 1986, 2,134 sqft. > Pool, A/C, 2-car garage. Est. $5,599/mo. Listed 20 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $1,047,000 | | Price/sqft | $491 | | Bedrooms | 3 | | Bathrooms | 2 full, 1 half | | Square Feet | 2,134 | | Year Built | 1986 | | Lot Size | 15,682 sqft (0.36 acres) | | Stories | 1 | | Garage | 2-car | | Property Type | Single Family (Single Family Residence) | | Status | Active | | Days on Market | 20 | ## Why This Home Stands Out - **Pool** - Pool listed; type not specified ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $5,294 | | Estimated Insurance | $305 | | **Total** | **$5,599** | ## Nearby Schools - **Elementary:** Laurel Nokomis Elementary - **Middle:** Laurel Nokomis Middle - **High:** Venice Senior High ## Key Amenities - Pool - A/C - 2-car garage ## Property Highlights - Built in 1986 - 0.36 acre lot - Private pool ## Description ### Agent Description Experience refreshed coastal living in Southbay Yacht and Racquet Club. This beautifully updated pool home pairs inviting interiors with outdoor spaces made for relaxing and entertaining. Fresh exterior paint and refreshed landscaping with new sod and palm trees create a welcoming arrival. Inside, new vinyl flooring flows through the living spaces and bedrooms, complemented by large format tile in the bathrooms. High ceilings and a decorative beam add character to the open living area. The redesigned kitchen features new cabinetry, quartz countertops with a waterfall detail, stainless steel appliances, a range hood, pendant lighting, illuminated shelving and a walk in pantry. The home offers three bedrooms, two full bathrooms and one half bathroom. The primary retreat offers two newly built closets and a beautifully remodeled bathroom with a spacious double vanity, freestanding soaking tub, separate shower, new fixtures and mirrors. The remodeled guest bathroom features a large double vanity, coordinating tile and updated shower fixtures. The layout features dual primary bedrooms, with the second offering a generous walk in closet, an attached half bathroom and exterior access. Practical updates complement the refreshed interiors, with hurricane rated windows throughout the home and hurricane shutters for added storm protection. New ceiling fans in the bedrooms, an interior laundry room with a new washer and dryer combo, and an oversized garage with an epoxy painted finish add everyday convenience. Step outside to the screened pool and covered lanai, with a new outdoor shower for rinsing off after a swim. An expanded paver area beyond the lanai with a built in outdoor fireplace offers another inviting space to relax and entertain. Enjoy Southbay Yacht and Racquet Club's waterfront lifestyle, featuring a community marina with Intracoastal access, a community pool, tennis, pickleball, a fitness center and clubhouse. From time on the water to relaxing evenings by your own pool, this home brings together beautifully updated spaces and an active coastal lifestyle. No CDD. ## Location - **Address:** 102 WINDWARD Drive, Osprey, FL 34229 - **County:** Sarasota - **Neighborhood:** SOUTHBAY YACHT & RACQUET CLUB - **Coordinates:** 27.179328, -82.484207 - **Google Maps:** https://www.google.com/maps?q=27.179328,-82.484207 ## Virtual Tour & Media - **Video Tour:** https://www.propertypanorama.com/instaview/stellar/TB8556740 ## Listing Agent - **Name:** Adam Leinwand - **Brokerage:** Future Home Realty, Inc - **Broker Phone:** (727) 409-3368 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/102-Windward-Dr_Osprey_FL_34229_M66747-84624?f=listhub&s=MFRMLSFL&m=TB8556740&c=propsimple) ## Photos ![102 WINDWARD Drive - Photo 1](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f2675923531r.jpg) ![102 WINDWARD Drive - Photo 2](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f737859111r.jpg) ![102 WINDWARD Drive - Photo 3](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f292941016r.jpg) ![102 WINDWARD Drive - Photo 4](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f1501895365r.jpg) ![102 WINDWARD Drive - Photo 5](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f3421770955r.jpg) ![102 WINDWARD Drive - Photo 6](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f2883620903r.jpg) ![102 WINDWARD Drive - Photo 7](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f2443702349r.jpg) ![102 WINDWARD Drive - Photo 8](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f3705318022r.jpg) ![102 WINDWARD Drive - Photo 9](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f367806083r.jpg) ![102 WINDWARD Drive - Photo 10](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f1677531696r.jpg) ![102 WINDWARD Drive - Photo 11](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f1844048977r.jpg) ![102 WINDWARD Drive - Photo 12](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f3541250508r.jpg) ![102 WINDWARD Drive - Photo 13](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f2886625707r.jpg) ![102 WINDWARD Drive - Photo 14](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f462243118r.jpg) ![102 WINDWARD Drive - Photo 15](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f1066373927r.jpg) ![102 WINDWARD Drive - Photo 16](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f2658203090r.jpg) ![102 WINDWARD Drive - Photo 17](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f1550077070r.jpg) ![102 WINDWARD Drive - Photo 18](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f2886625707r.jpg) ![102 WINDWARD Drive - Photo 19](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f78356797r.jpg) ![102 WINDWARD Drive - Photo 20](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f127096453r.jpg) ![102 WINDWARD Drive - Photo 21](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f78356797r.jpg) ![102 WINDWARD Drive - Photo 22](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f150163877r.jpg) ![102 WINDWARD Drive - Photo 23](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f1012257396r.jpg) ![102 WINDWARD Drive - Photo 24](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f31911165r.jpg) ![102 WINDWARD Drive - Photo 25](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f2234555538r.jpg) ![102 WINDWARD Drive - Photo 26](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f2234555538r.jpg) ![102 WINDWARD Drive - Photo 27](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f3014471953r.jpg) ![102 WINDWARD Drive - Photo 28](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f1425030714r.jpg) ![102 WINDWARD Drive - Photo 29](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f3118116786r.jpg) ![102 WINDWARD Drive - Photo 30](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f1425030714r.jpg) ![102 WINDWARD Drive - Photo 31](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f1542817059r.jpg) ![102 WINDWARD Drive - Photo 32](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f2011294309r.jpg) ![102 WINDWARD Drive - Photo 33](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f2448672775r.jpg) ![102 WINDWARD Drive - Photo 34](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f2297532223r.jpg) ![102 WINDWARD Drive - Photo 35](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f591282780r.jpg) ![102 WINDWARD Drive - Photo 36](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f2297532223r.jpg) ![102 WINDWARD Drive - Photo 37](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f591282780r.jpg) ![102 WINDWARD Drive - Photo 38](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f2339872066r.jpg) ![102 WINDWARD Drive - Photo 39](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f1207766344r.jpg) ![102 WINDWARD Drive - Photo 40](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f2929591610r.jpg) ![102 WINDWARD Drive - Photo 41](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f1207766344r.jpg) ![102 WINDWARD Drive - Photo 42](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f2929591610r.jpg) ![102 WINDWARD Drive - Photo 43](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f803316232r.jpg) ![102 WINDWARD Drive - Photo 44](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f624322915r.jpg) ![102 WINDWARD Drive - Photo 45](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f4128130887r.jpg) ![102 WINDWARD Drive - Photo 46](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f1501392209r.jpg) ![102 WINDWARD Drive - Photo 47](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f3757108717r.jpg) ![102 WINDWARD Drive - Photo 48](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f1501392209r.jpg) ![102 WINDWARD Drive - Photo 49](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f1661871764r.jpg) ![102 WINDWARD Drive - Photo 50](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f2699997822r.jpg) ![102 WINDWARD Drive - Photo 51](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f109726961r.jpg) ![102 WINDWARD Drive - Photo 52](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f12882479r.jpg) ![102 WINDWARD Drive - Photo 53](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f109726961r.jpg) ![102 WINDWARD Drive - Photo 54](http://lh.rdcpix.com/2fc84ad6d085ea4233b6e3cc5e1a74aal-f12882479r.jpg) --- **MLS#:** TB8556740 | **Updated:** 2026-10-24 **Source:** listhub *Copyright © 2026 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.* [View on PropertySimple](https://www.propertysimple.ai/listing/102-windward-drive-osprey-fl-34229-14c244ca35c94f90bc4b5d4e2c9e42a1) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://www.propertysimple.ai/listing/102-windward-drive-osprey-fl-34229-14c244ca35c94f90bc4b5d4e2c9e42a1#listing", "url": "https://www.propertysimple.ai/listing/102-windward-drive-osprey-fl-34229-14c244ca35c94f90bc4b5d4e2c9e42a1", "name": "102 WINDWARD Drive, Osprey, FL 34229", "description": "Experience refreshed coastal living in Southbay Yacht and Racquet Club. This beautifully updated pool home pairs inviting interiors with outdoor spaces made for relaxing and entertaining. Fresh exterior paint and refreshed landscaping with new sod and palm trees create a welcoming arrival. 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