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# A4595149 - Status: Active View Property Details Add to Favorites View Map

  • 4800 GULF OF MEXICO DR #PH4
  • Price: $910,000
  • Zip Code: 34228
  • 1312 Square Feet
  • Subdivision: WINDWARD BAY AMD
  • Bedrooms: 2 Baths: 2
  • ASTONISHING WATER VIEWS! Behold this "Must See" beautifully renovated from floors to raised ceilings, fully furnished 2-bedroom/2-bathroom luxurious Penthouse Condo. Experience from every room, unsurpassed embracing vistas of sparkling turquoise blue ... 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: $899,000
  • Zip Code: 34228
  • 1325 Square Feet
  • Subdivision: WINDWARD BAY AMD
  • Bedrooms: 2 Baths: 2
  • 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 Sarasota Bay, offering unparalleled vie ... 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: $892,000
  • Zip Code: 34228
  • 1900 Square Feet
  • Subdivision: WINDWARD BAY AMD
  • Bedrooms: 2 Baths: 2
  • OPPORTUNITY IS KNOCKING - OVER A $100,000 PRICE REDUCTION! Welcome to easy living, island style! This waterfront villa offers gorgeous Sarasota Bay and canal views plus the spaciousness of a single-family home (1900 SF), yet it is Maintenance-Free! I ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4584633 - Status: Active View Property Details Add to Favorites View Map

  • 4540 GULF OF MEXICO DR #PH1
  • Price: $860,000
  • Zip Code: 34228
  • 1561 Square Feet
  • Subdivision: WINDWARD BAY AMD
  • Bedrooms: 2 Baths: 2
  • DREAMS DO COME TRUE! SUNNY DELUXE CORNER END-UNIT REMODELED PENTHOUSE! Rare two bedroom/two bath end-unit Penthouse condominium, boasting 1561 square feet of "Gulf to Bay" Coastal Living. Sensational Sunrise and Sunset views await. Each day you have ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4581629 - Status: Active View Property Details Add to Favorites View Map

  • 4900 GULF OF MEXICO DR #PH5
  • Price: $859,900
  • Zip Code: 34228
  • 1312 Square Feet
  • Subdivision: WINDWARD BAY AMD
  • Bedrooms: 2 Baths: 2
  • JAW-DROPPING VIEW WITH A JAW-DROPPING PRICE IMPROVEMENT! THIS IS YOUR OPPORTUNITY TO OWN THIS SPECIAL PENTHOUSE ON LONGBOAT KEY WITH MULTI-MILLION DOLLAR WATER VIEWS! Step inside this 2-bedroom/2 bath Luxurious Penthouse Condo and instantly be captiv ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4569448 - Status: Active View Property Details Add to Favorites View Map

  • 4500 GULF OF MEXICO DR #206
  • Price: $839,900
  • Zip Code: 34228
  • 1523 Square Feet
  • Subdivision: WINDWARD BAY AMD
  • Bedrooms: 2 Baths: 2
  • AMAZING PRICE IMPROVEMENT OF $41,000! CORNER-END DELUXE SPECIAL CONDO ON LONGBOAT KEY! BEHOLD THE SPLENDOR! Imagine viewing joyous frolicking Dolphins from the comfort of your sparkling remodeled two-bedroom and two-bathroom condominium. Experience t ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4587598 - Status: Active View Property Details Add to Favorites View Map

  • 4500 GULF OF MEXICO DR #PH6
  • Price: $809,000
  • Zip Code: 34228
  • 1545 Square Feet
  • Subdivision: WINDWARD BAY AMD
  • Bedrooms: 2 Baths: 2
  • 40 FEET of DIRECT WATERFRONT VIEWS of Sarasota Bay! This FURNISHED CORNER PENTHOUSE offers the LARGEST square footage available within Windward Bay, the QUIETEST setting in the complex, and the MOST ACCESSIBILITY to the WATER for kayaking, grilling, ... Read More
  • Listing courtesy of: INVESTMENTS IN SARASOTA

MLS# A4595168 - Status: Active View Property Details Add to Favorites View Map

  • 4500 GULF OF MEXICO DR #305
  • Price: $799,000
  • Zip Code: 34228
  • 1325 Square Feet
  • Subdivision: WINDWARD BAY AMD
  • Bedrooms: 2 Baths: 2
  • Enjoy unobstructed bay views over the marina and mangrove islands in this recently updated 2-bedroom, 2-bathroom residence in the sought-after community of Windward Bay on Longboat Key. The third floor location offers panoramic views from every room. ... Read More
  • Listing courtesy of: COMPASS FLORIDA LLC

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
  • LOCATION, LOCATION, LOCATION - DON'T MISS THIS OPPORTUNITY! 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 d ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4591579 - Status: Active View Property Details Add to Favorites View Map

  • 4960 GULF OF MEXICO DR #A 205
  • Price: $735,000
  • Zip Code: 34228
  • 1325 Square Feet
  • Subdivision: WINDWARD BAY AMD
  • Bedrooms: 2 Baths: 2
  • You'll enjoy million-dollar bay views in this updated, fully furnished 2-bedroom, 2-bathroom residence in the sought-after community of Windward Bay on Longboat Key. The second-floor location is not only convenient and easily accessible by stairs or ... 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: $675,000
  • Zip Code: 34228
  • 1561 Square Feet
  • Subdivision: WINDWARD BAY AMD
  • Bedrooms: 2 Baths: 2
  • Welcome to your dream home on Sarasota Bay, a unique haven that defines the concept of an active yet peaceful lifestyle on Longboat Key. Step into a fresh floor plan that breaks away from the ordinary, where the layout captivates with the space you h ... 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: $648,000
  • Zip Code: 34228
  • 1025 Square Feet
  • Subdivision: WINDWARD BAY AMD
  • Bedrooms: 2 Baths: 2
  • OPPORTUNITY IS KNOCKING - REDUCED $27,000! NOW OFFERED FOR $648,000!! Welcome to your TurnKey Furnished dream home. This exquisite 2-bedroom, 2-bathroom villa has undergone a meticulous renovation, leaving no detail overlooked nor any expense spared. ... 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: $615,000
  • Zip Code: 34228
  • 1312 Square Feet
  • Subdivision: WINDWARD BAY AMD
  • Bedrooms: 2 Baths: 2
  • $35,000 PRICE REDUCTION! Showcasing serene, nature filled views of Sarasota Bay and a pristine Mangrove Preserve, you're sure to enjoy coastal living in this bright, airy two-bedroom, two-bathroom condo. Nestled in one of the most private and exclusi ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

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

  • 4770 GULF OF MEXICO DR #V-6
  • Price: $540,000
  • 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

MLS# A4589845 - Status: Active View Property Details Add to Favorites View Map

  • 4870 GULF OF MEXICO DR #V-12
  • Price: $449,000
  • Zip Code: 34228
  • 1025 Square Feet
  • Subdivision: WINDWARD BAY AMD
  • Bedrooms: 2 Baths: 2
  • As a new bonus incentive, seller will credit buyer $26,490.00 at closing to cover the special assessment which is due July 1, 2024. This is an effective value of $234/month to the buyer over a 15-year period, meaning the buyer's HOA will remain $234 ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4573674 - Status: Active View Property Details Add to Favorites View Map

  • 4720 GULF OF MEXICO DR #Villa 2
  • Price: $388,999
  • Zip Code: 34228
  • 912 Square Feet
  • Subdivision: WINDWARD BAY AMD
  • Bedrooms: 1 Baths: 1
  • PRICE IMPROVEMENT OF $46,000! GREAT OPPORTUNITY! Live in paradise in this charming one-bedroom, one-bath villa boasting 912 square feet to enjoy and unwind after a day spent soaking up the sun on the beach or kayaking on the bay. Perfect for couples ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY