Longboat Key · Waterfront · Condo · Townhome
Windward Bay in Longboat Key
A waterfront condominium community of condos and townhomes along the 4500 to 4900 blocks of Gulf of Mexico Drive on north Longboat Key, built in 1974 and 1975.
At a glance
Windward Bay at a glance
A waterfront condominium community of condos and townhomes along the 4500 to 4900 blocks of Gulf of Mexico Drive on north Longboat Key, built in 1974 and 1975.
- Median asking price
- $660K
- Lifestyle
- Waterfront, Condo, Townhome
The area
Living in Windward Bay
Overview of Windward Bay
About Windward Bay
Windward Bay is a waterfront condominium community on north Longboat Key, in the Manatee County part of the island, with buildings along the 4500 to 4900 blocks of Gulf of Mexico Drive. The association, Windward Bay, Inc., was formed in 1973, and the buildings date to 1974 and 1975.
Homes include condominiums and townhomes from about 910 to 1,900 square feet. Recent asking prices have run from about $585,000 to $795,000.
Anna Maria Island and St. Armands Circle are each a short drive away. I would be glad to compare buildings and views within Windward Bay with you and help you review the association documents before you buy.
What to know before you buy in Windward Bay
- I will confirm the HOA and any CDD fees, what they cover, and whether a transfer fee applies at closing.
- I will check the flood zone and elevation of the home, and we will get a flood insurance quote before your inspection period ends.
- If you may want to rent the home out, I will review the rental and lease rules with you.
- We will look at drive times to work, to SRQ, and to the beaches at the hours you would actually travel.
Buying in Windward Bay? I would be happy to walk you through everything before you make an offer. Email me or call me at (813) 394-3313.
Windward Bay FAQ
Is Windward Bay in Sarasota or Manatee County?
Windward Bay is on the Manatee County part of Longboat Key, with a Longboat Key address and ZIP 34228.
What kinds of homes are in Windward Bay?
The community has condominiums and townhomes built in 1974 and 1975, from about 910 to 1,900 square feet.
What do Windward Bay condos cost?
Recent asking prices have run from about $585,000 to $795,000, with a midpoint near $660,000, for homes of about 910 to 1,900 square feet.
Do you have a question about Windward Bay that is not answered here? I would be glad to help. Email me or call me at (813) 394-3313.
Climate
Weather, month by month
Average high and low in °F, and rain in inches, for each month.
Sarasota Bradenton International Airport (SRQ)
- Janhigh 72.5°low 52.3°2.8 in
- Febhigh 74.9°low 54.6°1.9 in
- Marhigh 78.2°low 58.1°2.9 in
- Aprhigh 82.5°low 62.7°2.5 in
- Mayhigh 87.5°low 68.2°2.6 in
- Junhigh 90.0°low 73.6°7.1 in
- Julhigh 91.1°low 75.2°7.4 in
- Aughigh 91.5°low 75.3°9.1 in
- Sephigh 90.2°low 74.1°6.0 in
- Octhigh 86.3°low 68.3°2.8 in
- Novhigh 80.0°low 60.1°1.8 in
- Dechigh 75.2°low 55.2°2.3 in
Atlantic hurricane season runs June 1 to November 30 (NOAA National Hurricane Center, https://www.nhc.noaa.gov/climo/); June through September is the rainy season, with most afternoons bringing a short thunderstorm.
NOAA climate normals, 1991 to 2020, Sarasota Bradenton International Airport (SRQ). Source: NOAA NCEI U.S. Climate Normals 1991-2020, station Sarasota Bradenton International Airport (https://www.ncei.noaa.gov/products/land-based-station/us-climate-normals), as reproduced in the Sarasota, Florida climate table (https://en.wikipedia.org/wiki/Sarasota,_Florida); read 2026-10-04.
Nearby
More communities in Longboat Key
Longboat Key
Longboat Key
Longboat Key
For sale now
Windward Bay homes for sale
I would be glad to send you new Windward Bay listings as soon as they come on the market, often before they reach the major portals. Ask Janelle
Updated October 13, 2026
Market now, as of October 13, 2026
- Homes for sale
- 7
- Median asking price
- $660K
Every quarter
Prices in Windward Bay
These are the homes sold in Windward Bay from July to September 2026, by closing date.
- Homes sold
- 3
- Median sale price
- $645K
- Median price per sq ft
- $423
- Lowest to highest sale
- $400K to $685K
| Sales | July to September 2026 | July to September 2025 |
|---|---|---|
| Homes sold | 3 | 3 |
| Median sale price | $644,950 | $520,000 |
| Median price per sq ft | $423 | $396 |
The median price per square foot was up 6.8% from July to September 2025.
On October 13, 2026, 7 homes were for sale in Windward Bay, at a median list price of $660K and a median $454 a square foot.
These figures are closed sales of homes (no land) in Stellar MLS, in the places this page's home search covers. Medians and the lowest and highest sales require at least 3 homes.
I update these figures every quarter from MLS sales. This is the July to September 2026 quarter, and the next update is in January 2027.
Keep reading
Guides from Janelle
· 7 min read
Downtown Sarasota or the Suburbs? A Lifestyle Guide to Arts and Space
Downtown Sarasota means walking from a condo to the bayfront, the opera, and the theater; Lakewood Ranch, Palmer Ranch, and Wellen Park offer more house, golf, and a drive in for a show. I compare them side by side.
· 9 min read
How to Price and Sell Your Sarasota Home in 2026: A Seller's Guide
How I price, prepare, and market homes in Sarasota and Lakewood Ranch, with September 2026 figures, the repairs worth making before you list, and gentle guidance on selling a vacation home you have owned for years.
· 8 min read
New Build or Resale, Coast or Inland: How to Choose a Sarasota Home
How to choose between a new build and a resale in Lakewood Ranch, and between coastal and inland Sarasota neighborhoods, with my September 2026 numbers and the flood and insurance checks I recommend for any home.
· 10 min read
Moving to Sarasota or Lakewood Ranch: Relocate, Downsize, Buy Remotely
How I time a sale and purchase, lead honest video tours and remote closings, and help downsizers, seasonal residents, and families find the right Sarasota or Manatee town.
New listings
Get new Windward Bay listings first
New Windward Bay listings often sell within days. Tell me what you are looking for, and I will send you new and coming-soon homes as soon as they come on the market, often before they reach the major portals. If you would rather talk, call or text me at (813) 394-3313.
Reviews
What clients say
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Janelle is fantastic. We recently were able to sell our home in one week at 1% over asking price. I believe that the professional photos and staging coupled with Janelle helping us price competitively led to this success. We closed in one month and are so very grateful for Janelle and her help with the sale of our property.
Google, October 7, 2026Sold a home
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I highly recommend Janelle Mertins She is extremely knowledgeable, honest, and incredibly helpful throughout the entire process. She is also very responsive and even made herself available after hours when needed. After working with several agents in the Sarasota area, Janelle truly stood out. Her professionalism and dedication made all the difference.
Google, April 7, 2026 -
Janelle did a great job selling our house. We have worked with 4 realtors over the past 19 years in FL, and she was by far the best. She is very knowledgeable about the real estate market, and was great at communicating with us throughout the sales process. Her responses to our emails and texts were very detailed and timely. She was also very proactive with recommendations on how to get our house ready for sale, and she went above and beyond to make sure our house was sparkling clean and staged appropriately to make sure our house stood out compared to others. The video she created for our...
RateMyAgent, July 20, 2025Sold a home in Bradenton
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Janelle Mertins · Compass
Would you like to see Windward Bay in person?
Call or text me directly whenever it suits you, or send me a note about the home, community, or move you have in mind.