Windward Bay

Listings For SaleSold History and Market Report

Windward Bay Condos for Sale – Longboat Key, Sarasota, Florida 34228

Windward Bay

An open invitation for viewing an available unit at Windward Bay is an opportunity that prospective buyers of Longboat Key condos for sale shouldn’t miss out. There are close to 60 units in this complex, but sales listings here aren’t very frequent.

Their superb location along the northern stretch of the 12-mile Gulf of Mexico Drive fronting Sarasota Bay is one of the primary reasons why the current owners of units at Windward Bay would want to hang on to their properties. This area is one of the popular vacation rental destinations in Longboat Key.

As a matter of fact, the Longboat Key Hilton Hotel opposite the entrance of Windward Bay has embarked on a $25-million renovation. This major makeover is expected to be completed toward the last quarter of 2015 and add some 85 rooms to the original 102 rooms in this hotel.

Great residential mix

Windward Bay

Developed around the mid-1970s, Windward Bay goes with all the features that make its residences a wise choice among Longboat Key condos for sale whether as a private seasonal home or a rental property. This community’s residences consist of a cluster of bungalow-type villas and condo units in mid-rise buildings within a 25-acre enclave.

The condominium complex offers a pair of swimming pools, a fitness facility, tennis courts and shuffleboard courts for the exclusive use of residents and rental clients. In addition to deeded beach access and a fishing dock, protected boat slips are also among the amenities at Windward Bay. Additionally, a nature preserve provides as a refreshing backdrop for the southern boundary of the property.

As winsome, the Windward Bay complex is nestled amid lush landscaping, with banyan trees, tropical palms, fruit trees and flowering shrubs among the greeneries. All these features come as maintenance-free for the community’s homeowners.

Attractive price ranges

Windward Bay

The pricing of available units at Windward Bay can be very reasonable compared to other listings in the Sarasota real estate market. The beach bungalow type villas in this community are typically sales-listed in the $300s, featuring two bedrooms within their floor areas measuring 800-plus square feet. Updated features, such as new sliding doors and windows rated for wind and impact, could further spur buying interest on these units.

The asking prices of units in Windward Bay’s midrise buildings could be quite attractive as well. These residences are typically in the $300s–$400s price range and have floor plans of between 1,096 and 1,325 square feet, all designed with two bedrooms. The pricier units are the community’s bayfront penthouse condos which afford a sweeping panorama the Sarasota skyline and flaunt recent interior upgrades.

Impressive renting potential

Likely to impress vacation rental property investors, a Windward Bay unit can yield as much as $3,500 per month during the peak tourist season.The sustained popularity of life and leisure venues in Sarasota, Anna Maria Island and in Longboat Key itself tremendously helps in continuously growing the rental clientele of Windward Bay.

The travel attractions near Windward Bay include the historic Village of Longboat Key which is a short distance north of the condominium complex. Southward, local dining and shopping venues also abound,with the merchants at St. Armands Circle and downtown Sarasota among them.


Windward Bay Condos for Sale

Below are the current real estate listings available at Windward Bay

Please contact me if you would like to schedule a tour of any of the listed properties below.

MLS# A4420391 - Status: Active View Property Details Add to Favorites View Map

  • 4800 GULF OF MEXICO DR #205
  • Price: $560,000
  • Zip Code: 34228
  • 1325 Square Feet
  • Subdivision: WINDWARD BAY CONDO AMD
  • Bedrooms: 2 Baths: 2
  • It doesn't get much better than this-----superb renovation, unique kitchen redesign, serene location! Step into this Bayfront residence and experience sweeping bay views, blue sky and lush landscaping. You will see an enlarged kitchen (17 x 10) with ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4421009 - Status: Active View Property Details Add to Favorites View Map

  • 4900 GULF OF MEXICO DR #PH5
  • Price: $538,000
  • Zip Code: 34228
  • 1335 Square Feet
  • Subdivision: WINDWARD BAY CONDO AMD
  • Bedrooms: 2 Baths: 2
  • Spectacular! You will love the gorgeous, unobstructed views of Sarasota Bay from this beautifully decorated/updated, Turn-Key Furnished, 2 Bed/2 Bath Penthouse. Entering your new home, your first word will be WOW. The open concept allows a wonderful ... Read More
  • Listing courtesy of: COLDWELL BANKER RES R E

MLS# A4422211 - Status: Active View Property Details Add to Favorites View Map

  • 4700 GULF OF MEXICO DR #PH3
  • Price: $525,000
  • Zip Code: 34228
  • 1325 Square Feet
  • Subdivision: WINDWARD BAY CONDO AMD
  • Bedrooms: 2 Baths: 2
  • Imagine looking at unobstructed full bay views from downtown Sarasota waterfront to the south, continuing along the bay to northwest Bradenton, nearly 20 miles of shoreline. Sunrises from every room! Enjoy mornings from the enclosed lanai while viewi ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4418795 - Status: Active View Property Details Add to Favorites View Map

  • 4500 GULF OF MEXICO DR #PH6
  • Price: $515,000
  • Zip Code: 34228
  • 1523 Square Feet
  • Subdivision: WINDWARD BAY CONDO AMD
  • Bedrooms: 2 Baths: 2
  • TREEHOUSE.. PENTHOUSE...BOATHOUSE! Fabulous opportunity for a fully remodeled, 2bed/2bath top floor condo, end location, that appears as if it sits atop lush trees yet is situated overlooking the boat harbor and vast Bay of Sarasota. This is a tru ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4415060 - Status: Active View Property Details Add to Favorites View Map

  • 4700 GULF OF MEXICO DR #303
  • Price: $419,900
  • Zip Code: 34228
  • 1312 Square Feet
  • Subdivision: WINDWARD BAY CONDO AMD
  • Bedrooms: 2 Baths: 2
  • Here is the perfect peaceful place to call home. This delightfully updated condominium features a wall of windows ideal for viewing the lovely canvas upon which sunrises and sunsets reveal their bounty of birds, dolphins, abundant fish and wildlife f ... Read More
  • Listing courtesy of: PREMIER SOTHEBYS INTL REALTY

MLS# A4422164 - Status: Active View Property Details Add to Favorites View Map

  • 4700 GULF OF MEXICO DR #305
  • Price: $415,000
  • Zip Code: 34228
  • 1312 Square Feet
  • Subdivision: WINDWARD BAY CONDO
  • Bedrooms: 2 Baths: 2
  • Gorgeous Sarasota Bay views are yours from every room in this 2 bed/2 bath, Turn-Key Furnished condo with Beach access right across the street! With 25+ feet of waterfront windows and a great location, the expansive Bay views make this perfect for re ... Read More
  • Listing courtesy of: COLDWELL BANKER RES R E

MLS# O5756822 - Status: Active View Property Details Add to Favorites View Map

  • 4540 GULF OF MEXICO DR #206
  • Price: $410,000
  • Zip Code: 34228
  • 1152 Square Feet
  • Subdivision: WINDWARD BAY CONDO AMD
  • Bedrooms: 2 Baths: 2
  • Wow!Your search has ended with this Amazing 2BD/2BA front end unit at WINDWARD BAY, offered turnkey furnished for your convenience or income investment purposes. Take in the beautiful serene views of your 2BD/2BA home quietly nestled at the edge of a ... Read More
  • Listing courtesy of: COLDWELL BANKER RESIDENTIAL RE

MLS# A4419076 - Status: Active View Property Details Add to Favorites View Map

  • 4600 GULF OF MEXICO DR #202
  • Price: $409,000
  • Zip Code: 34228
  • 1312 Square Feet
  • Subdivision: WINDWARD BAY CONDO AMD
  • Bedrooms: 2 Baths: 2
  • LARGE PET FRIENDLY FOR OWNERS AND TENANTS! MOVE-IN READY PROPERTY! BUY THIS PLACE IN PARADISE AND ESCAPE THE NORTHERN FREEZE! This 2BD/2BA condominium home, with picturesque water views, has an updated and open kitchen that shares sunrise views w ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4422082 - Status: Active View Property Details Add to Favorites View Map

  • 4540 GULF OF MEXICO DR #201
  • Price: $405,000
  • Zip Code: 34228
  • 1337 Square Feet
  • Subdivision: WINDWARD BAY CONDO AMD
  • Bedrooms: 2 Baths: 2
  • Stunning waterfront residence has undergone a gorgeous renovation, with views of the inter coastal and mangrove estuary. Highlighted updates include porcelain tile floors, a bright open kitchen which offers wood cabinetry, granite counter tops, stain ... Read More
  • Listing courtesy of: COLDWELL BANKER RES R E