Windward at Lakewood Ranch: Village Profile, Homes, Fees and Amenities

Where is Windward?

Windward sits at the southern gateway of Lakewood Ranch, Florida (Manatee and Sarasota counties), at the corner of Lorraine Road and Fruitville Road in Sarasota County, about 3.5 miles east of Interstate 75. Neal Communities’ sales address is 2618 Paradise Plum Drive, ZIP 34240. Because Windward is well south of University Parkway, the county line through Lakewood Ranch, homes fall under Sarasota County for property taxes, schools and county services.

Fruitville Road is the village’s main link to I-75 and to downtown Sarasota, which makes Windward one of the closer Lakewood Ranch villages to the city. Toll Brothers’ Monterey sits just to the east along Fruitville Road, and the Waterside villages and Waterside Place are to the north. For drive times, airports and the I-75 interchanges, see our guide to where Lakewood Ranch is and how the commutes work.

What is Windward like?

Windward is a gated, all-ages village of attached villas and single-family homes with a British West Indies design theme and Dutch Colonial touches. Island palms and tropical landscaping carry the theme through the streets, and the developer describes the architecture the same way in 2026.

Neal Communities bought the land in 2019. A March 2019 report put the purchase at about 450 acres for $21.55 million, with up to 900 homes planned, including villas, townhomes, affordable housing and some retail. By the time Windward held a virtual grand opening on August 27, 2020, attended online by about 1,000 people, the plan was a 540-acre gated community with 780 homes at buildout. In October 2026 the village was still on the developer’s list of villages selling new homes.

What homes are in Windward?

Neal Communities sells attached villas and single-family homes across four series, from about 1,433 to 4,443 square feet. The Coral series is the villa line; the Cruise, Celebration and Coastal series are single-family homes that step up in size and price.

Home type	Series (Neal)	Builder prices (Oct 2026)
Attached villas	Coral	$400s to $600s (developer); from the mid $300s (Neal)
Single-family homes	Cruise, Celebration, Coastal	$500s to $1M+ (developer); upper $400s to $1,056,990 (Neal)
All homes listed		$340,990 to $1,056,990 (Neal)

Sources: the developer’s Windward page and Neal Communities’ Windward page, October 2026. Prices are builder “from” prices for new construction and change often.

The developer’s page gives a size range of 1,433 to 2,907 square feet, while Neal’s page shows plans up to 4,443 square feet, so ask which plans are still available on remaining lots. Neal listed 24 quick move-in homes with completion dates from October 2026 through March 2027. Because Windward has been selling since 2020, it also has a resale market. Ask an agent to compare new prices with recent resales of the same plan, and see our quarterly Lakewood Ranch housing market report for the 34240 ZIP code.

What does Windward cost each month beyond the mortgage?

Plan for HOA dues of $200 to $400 a month, a CDD assessment, Sarasota County property tax and insurance, and check each for the exact address.

• HOA dues are published at $200 to $400 a month with maintenance included. The range likely reflects villas versus single-family homes, so ask which applies and what “maintenance included” covers, such as lawn mowing, irrigation or exterior work on the villas.
• CDD assessment. Unlike villages financed through the Lakewood Ranch Stewardship District, Windward has its own district, the Windward at Lakewood Ranch Community Development District. Sarasota County created it on December 11, 2019 (Ordinance 2019-050), and in 2020 it issued three bond series totaling about $16.9 million to pay for infrastructure, maturing between 2025 and 2050.
• Property tax is set by Sarasota County. Look up a parcel on the Sarasota County Property Appraiser site. If you will live in the home full time, see our homestead exemption guide.
• Insurance depends on the roof, construction and flood zone. See our hurricanes, flooding and insurance guide.

Windward CDD 2020 bonds	Amount
Series 2020A-1	$5,905,000
Series 2020A-2	$7,590,000
Series 2020A-3	$3,430,000
Total	About $16.9 million, at 3.0% to 4.85% interest

Source: the district’s fiscal 2020 annual financial report filed with the Florida Auditor General. The yearly assessment on any one home depends on its lot and the bond series that applies, so pull the latest tax bill for the address. Our guide to CDD fees in Lakewood Ranch explains how to read it, and our true cost of owning a home in Lakewood Ranch builds a full annual budget.

What amenities does Windward have?

Windward’s 7.8-acre amenity center has a 9,600-square-foot clubhouse, adult and children’s pools, eight pickleball courts, two tennis courts and a full-time lifestyle director. In 2020 Neal said the center would open in mid-2021.

Amenity	Details
Clubhouse	9,600 sq ft, with a fitness center
Pools	Resort-style pool and a separate children’s pool
Courts	8 pickleball courts and 2 tennis courts
Recreation	Sports fields and playgrounds
Pets and events	Two dog parks and two event lawns
Lifestyle	Full-time lifestyle director with social events

Source: Your Observer’s 2020 report on the amenity plans, and the developer’s and Neal’s 2026 pages.

Residents also share Lakewood Ranch’s parks and trails; see our guide to parks, trails and nature preserves. For dining and events, Waterside Place is a short drive north; see our Main Street and Waterside Place guide.

Which schools serve Windward?

Windward is in the Sarasota County Schools district, and Neal Communities lists Tatum Ridge Elementary, McIntosh Middle and Booker High for the village. Those are the builder’s listings, not a district guarantee. Boundaries in eastern Sarasota County change as new schools open, so confirm the zoned schools for the exact address with Sarasota County Schools before you sign.

Families also have charter and private options nearby. Construction finished in July 2026 on Sarasota Classical Preparatory Academy, a tuition-free K-8 charter school for about 900 students at 8743 Fruitville Road, with a preschool next door. Charter schools have their own application process. Our Lakewood Ranch schools guide explains zoning across the two counties and lists more options.

Who is Windward best for?

Windward suits families and retirees who want a newer gated village with a full amenity center, a Sarasota County address and prices that start well below $600,000.

If you want…	Windward is…
A villa or single-family home under about $600,000 in Sarasota County	A strong fit
A family pool, playgrounds and sports fields	A strong fit
Quick access to Fruitville Road and downtown Sarasota	A strong fit
Larger luxury homes over $1 million	A weaker fit; compare Monterey next door
A walkable town center	A weaker fit; compare Waterside
A 55+ community	Not a fit; see Del Webb Catalina or Cresswind

To compare every village side by side, see every Lakewood Ranch village compared.

What should I check before buying in Windward?

Check six things for any Windward home: the HOA budget, the CDD line on the tax bill, the flood zone, the warranty, the school zone and the home’s age.

1. Ask for the HOA budget and what “maintenance included” covers for villas and for single-family homes.
2. Pull the latest Sarasota County tax bill to see the exact Windward CDD assessment for that parcel.
3. Check the FEMA flood zone and ask for an elevation certificate, especially on lots that back onto ponds.
4. For new homes, read Neal’s warranty and hire an independent inspector. For homes built since 2020, ask how much builder warranty remains and check the AC and roof. Our guide to buying new construction vs resale explains the trade-offs.
5. Confirm the zoned schools with Sarasota County Schools.
6. Drive your commute on Fruitville Road at rush hour, ideally during tourist season.

Not ready to commit? See renting in Lakewood Ranch before you buy. When you are ready, our real estate hub explains how to choose an agent who knows the villages and can represent you with a builder.