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# A4450381 - Status: Active View Property Details Add to Favorites View Map

  • 4800 GULF OF MEXICO DR #C205
  • Price: $560,000
  • Zip Code: 34228
  • 1325 Square Feet
  • Subdivision: WINDWARD BAY CONDO AMD
  • Bedrooms: 2 Baths: 2
  • You'll fall in love with the floor plan in this totally renovated bay front residence. No expense was spared to create this masterpiece. The kitchen has been enlarged to accommodate more cabinets, a wine refrigerator, a granite island that seats 6, ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4452513 - Status: Active View Property Details Add to Favorites View Map

  • 4700 GULF OF MEXICO DR #306
  • Price: $529,800
  • Zip Code: 34228
  • 1376 Square Feet
  • Subdivision: WINDWARD BAY CONDO AMD
  • Bedrooms: 2 Baths: 2
  • Spectacular Bay Views and Luxury Finishes Adorn this Outstanding, Updated 2 Bedroom, 2 Bath Tommy Bahama Inspired End Unit. The owners recently renovated the kitchen and bathrooms. Some of the upgrades include Cherry Wood Cabinets, Wine Storage, Gra ... Read More
  • Listing courtesy of: WAGNER REALTY

MLS# A4459680 - Status: Active View Property Details Add to Favorites View Map

  • 4900 GULF OF MEXICO DR #203
  • Price: $524,000
  • Zip Code: 34228
  • 1312 Square Feet
  • Subdivision: WINDWARD BAY CONDO AMD
  • Bedrooms: 2 Baths: 2
  • This charming condominium in desirable Windward Bay on Longboat Key includes an open floor plan and first-rate appointments everywhere. Entering the home you are greeted by expansive, unobstructed views of Sarasota Bay, Intercoastal Waterway and the ... Read More
  • Listing courtesy of: PREMIER SOTHEBYS INTL REALTY

MLS# A4460638 - Status: Active View Property Details Add to Favorites View Map

  • 4700 GULF OF MEXICO DR #PH3
  • Price: $519,000
  • Zip Code: 34228
  • 1312 Square Feet
  • Subdivision: WINDWARD BAY CONDO AMD
  • Bedrooms: 2 Baths: 2
  • Easy to see and show even with social distancing. Contact us for a virtual tour or FaceTime showing of this not to be missed, fully and beautifully remodeled, chic two bedroom/two bathroom penthouse level (no one living above!) condo with fabulous Sa ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4437978 - Status: Active View Property Details Add to Favorites View Map

  • 4810 GULF OF MEXICO DR
  • Price: $499,000
  • Zip Code: 34228
  • 1344 Square Feet
  • Subdivision: WINDWARD BAY CONDO AMD
  • Bedrooms: 3 Baths: 2
  • SELLER MOTIVATED AND WANTS AN OFFER THIS SEASON! 3BED/ 2BA VILLA! Lives like a single-family home without all the work. Private covered parking right at your front door and YOUR OWN GRILL just outside the back door! This home has been completely u ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4436854 - Status: Active View Property Details Add to Favorites View Map

  • 4820 GULF OF MEXICO DR
  • Price: $494,000
  • Zip Code: 34228
  • 1334 Square Feet
  • Subdivision: WINDWARD BAY CONDO AMD
  • Bedrooms: 3 Baths: 2
  • Nestled in the Windward Bay community on Longboat Key, this villa with deeded beach access boasts three bedrooms plus two bathrooms. A beautiful pet friendly community . Get ready to enjoy the outdoor activities this beautiful community offer with ... Read More
  • Listing courtesy of: RE/MAX ALLIANCE GROUP

MLS# A4457544 - Status: Active View Property Details Add to Favorites View Map

  • 4540 GULF OF MEXICO DR #306
  • Price: $450,000
  • Zip Code: 34228
  • 1325 Square Feet
  • Subdivision: WINDWARD BAY CONDO AMD
  • Bedrooms: 2 Baths: 2
  • Imagine living on Longboat Key on the Bayfront for this price! This corner residence with 1523 sq.ft. is great value. The kitchen interior wall has been removed to bring the bay view to your fingertips. There are newer appliances in the sunny dine in ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4439434 - Status: Active View Property Details Add to Favorites View Map

  • 4600 GULF OF MEXICO DR #204
  • Price: $409,900
  • Zip Code: 34228
  • 1312 Square Feet
  • Subdivision: WINDWARD BAY CONDO AMD
  • Bedrooms: 2 Baths: 2
  • You could be the lucky owner of this turnkey furnished 2 bed/2 bath large pet friendly, bay front condo with panoramic views of Sarasota Bay, boat slips, and 3 accesses to the sugary sand beach right across the street! With consistent rental income f ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4447041 - Status: Active View Property Details Add to Favorites View Map

  • 4960 GULF OF MEXICO DR #PH5
  • Price: $375,000
  • Zip Code: 34228
  • 1352 Square Feet
  • Subdivision: WINDWARD BAY CONDO AMD
  • Bedrooms: 2 Baths: 2
  • Living at Windward Bay offers a lovely direct-bayfront lifestyle complemented by an array of amenities. This two-bedroom, top-floor residence is a flourish of views of the community marina that stretch out to Sarasota Bay's tranquil waters. The bayfr ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4459846 - Status: Active View Property Details Add to Favorites View Map

  • 4540 GULF OF MEXICO DR #301
  • Price: $360,000
  • Zip Code: 34228
  • 1561 Square Feet
  • Subdivision: WINDWARD BAY CONDO AMD
  • Bedrooms: 2 Baths: 2
  • Easy to see and show even with social distancing. Contact us for a virtual tour or FaceTime showing. The owner of this 2 bed/2 bath END UNIT condo wants an offer and will make a deal! Check out the great price of only $360,000! This condo has a lot o ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY