Windward Bay

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

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

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

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

• 4976 GULF OF MEXICO DR #Villa 18
• Price: $1,000,000
• Zip Code: 34228
• 1900 Square Feet
• Subdivision: WINDWARD BAY AMD
• Bedrooms: 2 Baths: 2
• 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! It's the best of both worlds...the size of a house yet the e ... Read More
• Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4579070 - Status: Active View Property Details Add to Favorites View Map

• 4700 GULF OF MEXICO DR #201
• Price: $999,999
• Zip Code: 34228
• 1561 Square Feet
• Subdivision: WINDWARD BAY AMD
• Bedrooms: 2 Baths: 2
• This beautiful, spacious, 1561 square foot 2 bedroom 2 full bath end unit condo was completely renovated down to the studs in 2022. EVERYTHING IS NEW! LED lights throughout. The large gourmet chef's kitchen includes quartz countertops, subway tile ba ... Read More
• Listing courtesy of: KEYS REALTY REDEFINED LLC

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

• 4900 GULF OF MEXICO DR #PH5
• Price: $940,555
• Zip Code: 34228
• 1312 Square Feet
• Subdivision: WINDWARD BAY AMD
• Bedrooms: 2 Baths: 2
• PRICE IMPROVEMENT AND JAW-DROPPING! 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 captivated by the seamless ... 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: $899,000
• 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# A4587598 - Status: Active View Property Details Add to Favorites View Map

• 4500 GULF OF MEXICO DR #PH6
• Price: $890,000
• Zip Code: 34228
• 1545 Square Feet
• Subdivision: WINDWARD BAY AMD
• Bedrooms: 2 Baths: 2
• 40 FEET of DIRECT WATERFRONT VIEWS of Sarasota Bay from EVERY room! This updated 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 kayak ... Read More
• Listing courtesy of: INVESTMENTS IN SARASOTA

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

• 4960 GULF OF MEXICO DR #A 205
• Price: $779,500
• 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# A4576362 - Status: Active View Property Details Add to Favorites View Map

• 4540 GULF OF MEXICO DR #201
• Price: $771,000
• Zip Code: 34228
• 1561 Square Feet
• Subdivision: WINDWARD BAY AMD
• Bedrooms: 2 Baths: 2
• NATURE'S DREAM HOME! LONGBOAT KEY! This Beautiful and Spacious 1561 square foot 2-bedroom, 2-bath corner deluxe end unit condo, offers a peaceful retreat for nature lovers and beach enthusiasts alike. As you step inside, you'll be greeted by a bright ... Read More
• Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4589158 - Status: Active View Property Details Add to Favorites View Map

• 4974 GULF OF MEXICO DR #Villa 19
• Price: $750,000
• Zip Code: 34228
• 1621 Square Feet
• Subdivision: WINDWARD BAY AMD
• Bedrooms: 3 Baths: 2
• Welcome to your waterfront paradise! This 3 Bedroom, 2 Bathroom villa home beckons the discerning Buyer with the promise of a blissful waterfront lifestyle and the potential for a luxury living experience. With a new interior to be custom designed by ... 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: $675,000
• Zip Code: 34228
• 1025 Square Feet
• Subdivision: WINDWARD BAY AMD
• Bedrooms: 2 Baths: 2
• Welcome to your dream home! This exquisite 2-bedroom, 2-bathroom villa has undergone a meticulous renovation, leaving no detail overlooked nor any expense spared. The open-concept design welcomes you with a spacious and modern feel, boasting a neutra ... 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: $650,000
• Zip Code: 34228
• 1312 Square Feet
• Subdivision: WINDWARD BAY AMD
• Bedrooms: 2 Baths: 2
• Showcasing serene, nature filled views of Sarasota Bay and a pristine Mangrove Preserve, you're sure to enjoy coastal living in this bright and airy two-bedroom, two-bathroom condo. Nestled in one of the most private and exclusive parts of the commun ... Read More
• Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4568180 - Status: Active View Property Details Add to Favorites View Map

• 4760 GULF OF MEXICO DR #Villa 7
• Price: $390,000
• Zip Code: 34228
• 912 Square Feet
• Subdivision: WINDWARD BAY AMD
• Bedrooms: 1 Baths: 1
• Price Improvement! The Longboat Key square foot price is UNBELIEVABLE! This bright and spacious remodeled Villa is the largest Longboat Key one-bedroom Villa on the market at 912 square feet. Relaxation and tranquility await as you gaze from your Liv ... Read More
• Listing courtesy of: COLDWELL BANKER REALTY

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