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Windward

Neighborhood Overview Video

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Windward: Caribbean-Inspired Living at Lakewood Ranch's Southern Gateway

Welcome

Welcome to Windward at Lakewood Ranch, where Caribbean-inspired charm meets the active Florida lifestyle in one of Sarasota County's most desirable locations. This Neil Communities development represents their largest project in Lakewood Ranch to date, delivering a delightful blend of tropical architecture and family-friendly amenities. Experience resort-style living with the convenience of being perfectly positioned between established Lakewood Ranch and downtown Sarasota.

Neighborhood Character

Windward stands as one of the few villages straddling the Sarasota County line, creating a unique position near both Waterside and the established Lakewood Ranch South. As Neil's largest Lakewood Ranch project, this community embodies their signature approach to building lasting neighborhood connections. The development showcases a true multi-generational appeal with no age restrictions, fostering a vibrant community where empty nesters in attached villas live alongside growing families in spacious single-family homes.

Housing Options

Windward offers an impressive range of housing options featuring distinctive British West Indies architecture with Dutch colonial touches. The signature bright white homes with dark shutters and coral doors create a tropical vacation atmosphere throughout the community. Attached villas provide approximately 1,400-1,500 square feet with two bedrooms plus a den, perfect for those seeking maintenance-free living. Single-family homes range from charming 1,600 square foot cottages to expansive 3,000+ square foot residences with four to five bedrooms, accommodating families of all sizes and entertaining needs.

Pricing and Fees

Investment in Windward represents excellent value within the Lakewood Ranch market, with villas starting in the $400,000s and single-family homes beginning in the $500,000s. The largest homes with pools extend well over $1 million, while the median price typically falls in the $600,000-$700,000 range. HOA fees range from $300-$450 monthly depending on home type, covering lawn maintenance and access to the spectacular community amenities. This fee structure provides exceptional value considering the resort-style amenities and maintenance-free lifestyle included.

Amenities & Lifestyle

Windward delivers truly spectacular amenities that create a country club atmosphere without the golf. The amenity-rich community features a spacious clubhouse with fitness center, two pools including a resort-style pool and lap pool, and an impressive sports complex with eight pickleball courts and four tennis courts. Families enjoy the pirate ship-themed playground, dog park, and meandering trails throughout the community. A full-time lifestyle director coordinates events and activities, fostering the strong community spirit Neil Communities is known for creating.

Location Advantages

Windward's geography provides fantastic accessibility as the most southern community in Lakewood Ranch, positioned at the corner of Lorraine and Fruitville Roads in the southeast section of Waterside. Residents enjoy exceptional convenience with:

• 5-minute access to Waterside Place (walkable or bikeable)

• 10-15 minutes to UTC and the entire Town Center area

• Less than 20 minutes to downtown Sarasota

• Under 30 minutes to any Sarasota beach

• Strategic positioning halfway between Lakewood Ranch proper and Sarasota

This prime location truly offers the best of both worlds, combining suburban tranquility with urban accessibility.

Local Conveniences

Living in Windward means enjoying easy access to some of Southwest Florida's premier shopping, dining, and entertainment destinations. The walkable connection to Waterside Place provides waterfront dining and boutique shopping just steps away. The proximity to UTC offers extensive retail options, fine dining, and entertainment venues. Downtown Sarasota's cultural attractions, farmers markets, and beach access are all within a short drive, while the convenience of skipping parking by biking to many destinations via connected trails adds to the community's appeal.

Unique Value Proposition

What truly distinguishes Windward is Neil Communities' signature approach to building authentic neighborhood connections combined with resort-style amenities. The community's internal web portal helps residents connect, while the integration with surrounding Waterside trails creates a larger network for outdoor enthusiasts. The British West Indies architectural theme, complete with unique features like the decorative footbridge connecting neighborhoods, creates a distinctive tropical vacation atmosphere. The thriving pickleball scene with eight courts and beginner lessons makes it easy for newcomers to immediately connect with neighbors.

Contact Us

Ready to experience the island time mentality and active living that makes Windward special? Contact the Zachos Realty & Design Group today to explore this exceptional Lakewood Ranch community. Our team of local experts understands what makes each neighborhood unique and can help you find your perfect place in paradise. Call, text, or email us anytime to begin your journey to Southwest Florida living.

Contact Us

Discover Windward

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