Windward Bay

Listings For SaleSold History and Market Report

Windward Bay Condos for Sale – Longboat Key, Florida 34228

Windward Bay

Windward Bay is a cozy residential complex at 4500-4980 Gulf of Mexico Drive backing up to Sarasota Bay. This property can easily endear itself to prospective buyers of Longboat Key condos for sale particularly when the Ponciana trees in its locality are in full bloom with orange flowers.

This condominium complex was developed sometime in the mid-1970s, creating the epitome of an island resort community. The Windward Bay residences are set within a palette of beautiful landscaping with flowering shrubs, tropical palms, fruit trees, and other equally charming greeneries. What’s even more, a verdant nature preserve separates the northern and southern stretches of the 25-acre property.

Midrise condos and villas

Windward Bay

Set up as a maintenance-free community, Windward Bay is comprised of some 60 units in two residential styles. Most of these condos are housed within seven four-story buildings laid out parallel to the bayside of the property. Separate clusters of bungalow-type villas account for the other residential units within this charming enclave.

The available properties in this community are quite competitive when compared with other Longboat Key condos for sale in the Sarasota real estate market. Windward Bay’s one-story villas having floor plans of around 1,000 square feet and featuring a two-bedroom layout would typically be offered at asking prices starting from the high $200s up to the $400s.

The more plentiful Windward Bay condos within the property’s midrise buildings would generally fall within the same price range. These units too come in two-bedroom designs within floor areas from 1,096 square feet up to about 1,500 square feet. The pricier among these condos and villas are those which afford commanding views of the bay and have had recent interior upgrades.

Thrilling list of amenities

Windward Bay

A bevy of convenient facilities and exciting amenities brings Windward Bay among the leading destinations for searches of Longboat Key condos for sale. Under-building parking is provided in the midrise condos, while the villas have individual covered garages. There is ample street parking as well within the Windward Bay enclave.

The in-house attractions of this condominium complex include two swimming pools, tennis and shuffleboard courts, plus a fitness facility. Other amenities within Windward Bay include a fishing pier and boat docks allowing safe and easy access to Sarasota Bay. Notably, just off east of the property’s bayside are several islets frequented by seabirds and whose waters are areas frequented by manatees. Across west of Gulf of Mexico Drive, Windward Bay condo residents likewise have convenient access to the beach.

Potential for renting

With all these superb features, an available unit at Windward Bay isn’t only suitable as a private vacation residence. A condo here can potentially generate regular rental income, as Windward Bay is right amid property developments primarily catering to the tourism and travel trade.

Right across the Windward Bay entrance, for example, the Zota Beach Resort is set to open in late 2016. Formerly known as the Longboat Key Hilton, this oceanfront property is being redeveloped to include more offerings besides its 187 new hotel rooms. In addition to these accommodations, the resort will also feature a “state-of-the art meeting space,” restaurant and wine bar, enticing social venues which could add more plus points for neighboring Windward Bay condos for sale.


Windward Bay Condos for Sale

Below are all of the current real estate listings available for sale at Windward Bay.

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

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

  • 4700 GULF OF MEXICO DR #PH6
  • Price: $849,900
  • Zip Code: 34228
  • 1523 Square Feet
  • Subdivision: WINDWARD BAY AMD
  • Bedrooms: 2 Baths: 2
  • AMAZING BONUS OFFER! SELLER IS OFFERING TO EITHER PAY OFF THE 7/1/24 SPECIAL ASSESSMENT OR BUYER MAY DEDUCT $26,490 FROM LIST PRICE. The choice is yours! This is your lucky day for an AMAZING OPPORTUNITY! BREATHTAKING BAYFRONT WATER-VIEW PENTHOUSE! W ... 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
  • SPACIOUS MAINTENANCE FREE WATERFRONT HOME - MOTIVATED SELLER - $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
  • HUGE REDUCTION PLUS THE SELLER HAS PREPAID ALL 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- CHECK IT OUT! Ente ... 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 IS MOTIVATED TO MAKE A DEAL! ALL OFFERS ENCOURAGED. 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 di ... 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# 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# A4587513 - Status: Active View Property Details Add to Favorites View Map

  • 4860 GULF OF MEXICO DR #Villa 13
  • Price: $575,000
  • Zip Code: 34228
  • 1025 Square Feet
  • Subdivision: WINDWARD BAY AMD
  • Bedrooms: 2 Baths: 2
  • MOTIVATED SELLER - NEW LOWER PRICE - PREVIOUS SPECIAL ASSESSMENT PAID IN FULL! This exquisite 2-bedroom, 2-bathroom TURNKEY FURNISHED villa has undergone a METICULOUS RENOVATION, leaving no detail overlooked nor any expense spared. The open-concept d ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY