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# A4604266 - Status: Active View Property Details Add to Favorites View Map

  • 4700 GULF OF MEXICO DR #PH6
  • Price: $850,000
  • Zip Code: 34228
  • 1523 Square Feet
  • Subdivision: WINDWARD BAY AMD
  • Bedrooms: 2 Baths: 2
  • BREATHTAKING BAYFRONT WATER-VIEW PENTHOUSE! WELCOME TO PARADISE! Rare opportunity to own this beautiful END-UNIT, one of a kind two-bedroom, two-bathroom penthouse. The Best Bayfront Water Views with direct panoramic viewing of Sarasota Bay, the Inte ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4589073 - Status: Active View Property Details Add to Favorites View Map

  • 4976 GULF OF MEXICO DR #Villa 18
  • Price: $800,000
  • Zip Code: 34228
  • 1900 Square Feet
  • Subdivision: WINDWARD BAY AMD
  • Bedrooms: 2 Baths: 2
  • MOTIVATED SELLER - SPACIOUS MAINTENANCE FREE WATERFRONT HOME - $200,000 PRICE REDUCTION! This waterfront villa offers gorgeous Sarasota Bay and canal views plus the spaciousness (1900 SF) of a single-family home with 2 bedrooms, a den, 2 bathrooms, l ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4601556 - Status: Active View Property Details Add to Favorites View Map

  • 4540 GULF OF MEXICO DR #205
  • Price: $795,000
  • Zip Code: 34228
  • 1325 Square Feet
  • Subdivision: WINDWARD BAY
  • Bedrooms: 2 Baths: 2
  • WOOHOO - BIG PRICE REDUCTION PLUS THE SELLER HAS PREPAID ALL OF THE 2024 HOA FEES AND THE UPCOMING $26,490 SPECIAL ASSESSMENT IN FULL. THESE WILL BE CREDITS TO THE BUYER AT CLOSING! ALSO THIS COMMUNITY IS ELIGIBLE FOR FINANCING VIA PORTFOLIO LOANS- C ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4593777 - Status: Active View Property Details Add to Favorites View Map

  • 4500 GULF OF MEXICO DR #PH4
  • Price: $795,000
  • Zip Code: 34228
  • 1325 Square Feet
  • Subdivision: WINDWARD BAY AMD
  • Bedrooms: 2 Baths: 2
  • MOTIVATE SELLER! ENCOURAGES ALL OFFERS! Welcome to Windward Bay, where the allure of waterfront living meets the epitome of luxury on Longboat Key, Florida. This exquisite 2-bedroom, 2-bath condo is a haven nestled directly on the shores of sparkling ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4600211 - Status: Active View Property Details Add to Favorites View Map

  • 4600 GULF OF MEXICO DR #PH2
  • Price: $785,000
  • Zip Code: 34228
  • 1312 Square Feet
  • Subdivision: WINDWARD BAY AMD
  • Bedrooms: 2 Baths: 2
  • SELLER ENCOURAGES ALL OFFERS AND IS MOTIVATED TO MAKE A DEAL! The stunning, unobstructed views of Sarasota Bay from every room of this 2 BR/2 BA bay front, top floor, penthouse beauty are a dream come true. With wide water views, three beach accesses ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4606923 - Status: Active View Property Details Add to Favorites View Map

  • 4900 GULF OF MEXICO DR #204
  • Price: $749,000
  • Zip Code: 34228
  • 1312 Square Feet
  • Subdivision: WINDWARD BAY AMD
  • Bedrooms: 2 Baths: 2
  • MUST SEE! Prized Waterfront Location! A sparkling remodeled two bedroom, two bath condominium with SPECTACULAR WATER VIEWS from every room. Attention to detail, resplendent in both design and livability is apparent. Imagine preparing delicious meals ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4580528 - Status: Active View Property Details Add to Favorites View Map

  • 4540 GULF OF MEXICO DR #204
  • Price: $600,000
  • Zip Code: 34228
  • 1312 Square Feet
  • Subdivision: WINDWARD BAY AMD
  • Bedrooms: 2 Baths: 2
  • MOTIVATED SELLER - MAKE AN OFFER! Bright and airy two-bedroom, two-bathroom condo, showcasing views of Sarasota Bay and a pristine Mangrove Preserve. Nestled in one of the most private and exclusive parts of the community, this home offers three conv ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4587513 - Status: Active View Property Details Add to Favorites View Map

  • 4860 GULF OF MEXICO DR #Villa 13
  • Price: $590,000
  • Zip Code: 34228
  • 1025 Square Feet
  • Subdivision: WINDWARD BAY AMD
  • Bedrooms: 2 Baths: 2
  • WOOHOO...OPPORTUNITY IS KNOCKING - MOTIVATED SELLER REDUCED THE PRICE AND PAID THE PREVIOUS SPECIAL ASSESMENT IN FULL! This exquisite 2-bedroom, 2-bathroom TURNKEY FURNISHED villa has undergone a METICULOUS RENOVATION, leaving no detail overlooked no ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4594909 - Status: Active View Property Details Add to Favorites View Map

  • 4540 GULF OF MEXICO DR #201
  • Price: $575,000
  • Zip Code: 34228
  • 1561 Square Feet
  • Subdivision: WINDWARD BAY AMD
  • Bedrooms: 2 Baths: 2
  • One or more photo(s) has been virtually staged. NEWLY PAINTED INTERIOR! BRIGHT FRESH WALLS and BRAND NEW CARPET JUST INSTALLED. Welcome to your dream home on Sarasota Bay, a unique haven that defines the concept of an active yet peaceful lifestyle on ... Read More
  • Listing courtesy of: PREMIER SOTHEBYS INTL REALTY

MLS# A4592314 - Status: Active View Property Details Add to Favorites View Map

  • 4770 GULF OF MEXICO DR #V-6
  • Price: $499,000
  • Zip Code: 34228
  • 911 Square Feet
  • Subdivision: WINDWARD BAY AMD
  • Bedrooms: 2 Baths: 1
  • Enjoy the bay breeze and life of ease, yes please! Welcome to this spacious, newly remodeled, single story villa in Windward Bay on Longboat Key. The home's coastal style renovation features an airy, open plan kitchen perfect for entertaining, with w ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY