Windmill Point Homes for Sale

About Windmill Point Neighborhood

Windmill Point is a family-friendly residential community located in the Pleasant Hill corridor of southwestern Kissimmee, within the 34746 zip code. Developed in multiple phases from 1993 through 2003 by Maronda Homes — one of Central Florida's most prolific production builders — the neighborhood encompasses several hundred single-family residences arranged along Windmill Point Boulevard and its interior cul-de-sacs. The community sits just south of the US 17-92 (John Young Parkway) and Pleasant Hill Road intersection, providing direct access to two of Osceola County's major commuter corridors.

Homes in Windmill Point are predominantly concrete block construction with stucco exteriors, designed in traditional Florida ranch and two-story floor plans. Living areas range from approximately 1,300 to 2,400 square feet, offering three to five bedrooms and two to three bathrooms. Many properties sit on oversized lots of roughly 0.25 to 0.30 acres, which is notably larger than what newer Kissimmee subdivisions typically offer. Homeowners enjoy spacious fenced backyards, two-car garages, and split-bedroom layouts that provide privacy for family living.

A defining characteristic of Windmill Point is its network of community ponds and conservation buffers that weave through the subdivision. Numerous homesites back up to scenic retention ponds, providing waterfront views, visiting wading birds, and a natural buffer between neighboring properties. Mature landscaping — including tropical fruit trees such as mango, avocado, and guava — gives the community a lush, established feel that newer developments cannot replicate. The neighborhood's location near the Valencia College Poinciana Campus also brings convenient higher-education access for residents pursuing degrees or professional certifications.

Windmill Point Location & Connections

Windmill Point is located in the Pleasant Hill area of southwestern Kissimmee, directly accessible from Pleasant Hill Road just south of its intersection with John Young Parkway (US 17-92). The community sits in a residential pocket surrounded by established neighborhoods and conservation lands, providing a quiet suburban setting while remaining connected to Kissimmee's primary retail and commuting corridors.

John Young Parkway runs north to The Loop shopping center and onward to Orlando, while Pleasant Hill Road connects south toward the Poinciana corridor. The Florida Turnpike entrance at US 17-92 is approximately 5 miles north, providing statewide highway access for commuters. Valencia College Poinciana Campus sits within a short drive, and Pleasant Hill Commons Shopping Center provides everyday grocery and retail needs just minutes away.

Windmill Point Amenities & Lifestyle

Life in Windmill Point revolves around the easygoing character of a mature, established neighborhood. The community's spacious lots and quiet cul-de-sacs create an environment well suited to families, first-time homebuyers, and anyone who values yard space and a relaxed pace of living. The Pleasant Hill corridor provides essential shopping, dining, and services within a short drive, while Kissimmee's broader entertainment and outdoor recreation scene is readily accessible.

Windmill Point's location in the heart of the Pleasant Hill area places residents near Valencia College Poinciana Campus, multiple school options in the Osceola County system, and the expanding retail options along John Young Parkway. Whether you are looking for weekend fishing at the Granada Public Boat Ramp, a round of golf at one of Kissimmee's championship courses, or a day at the theme parks, Windmill Point provides a convenient home base without the premium price tags of resort-corridor communities.

How Windmill Point Compares

Windmill Point occupies a compelling value position in the Pleasant Hill corridor. Its established Maronda-built homes on oversized lots, combined with the absence of CDD fees, create meaningful savings compared to both newer master-planned communities and similar-era neighborhoods with more extensive amenity packages and correspondingly higher fees.

Windmill Point HOA & CDD Information

Windmill Point has a mandatory homeowners association that oversees community standards and common area maintenance. The HOA fee is structured as an annual assessment and is widely recognized as one of the more affordable HOA fees in the Pleasant Hill area — consistent with the community's no-frills, value-focused character.

Windmill Point does not have a Community Development District (CDD) fee. This is a significant financial advantage over many newer subdivisions in southern Kissimmee and the Poinciana corridor, where CDD assessments can add $1,500 to $4,000 or more annually to a homeowner's carrying costs. The absence of a CDD means lower total monthly expenses for Windmill Point residents. To learn more about how CDDs work, see our guide to understanding CDD fees.

Frequently Asked Questions