Cypress Ridge Homes for Sale

About Cypress Ridge Neighborhood

Cypress Ridge occupies a prime slice of northern Kissimmee between West Carroll Street, Pleasant Cypress Circle, and North Thacker Avenue — just west of John Young Parkway and within a short walk of Flora Ridge Elementary School. Ryan Homes, one of the nation's most recognized production builders, developed the community between 2018 and 2021, delivering 144 two-story townhomes across a compact, walkable footprint that has since sold out. The community's sold-out status is itself a testament to the demand for quality, gated, maintenance-free living at this location in Kissimmee.

Buyers choose from two floor plans — the Aspen-Arbor and the Ash-Arbor — both offering three bedrooms, two and a half baths, and living areas between 1,747 and 1,771 square feet. Ryan Homes incorporated a full suite of modern features into every home: stainless steel appliances, tile floors, beautiful cabinetry, pendant lighting, Wi-Fi Nest thermostats, and Wi-Fi garage door openers. The two-story open-concept layouts place gourmet kitchens with oversized islands at the heart of the main floor, while the owner's suite upstairs is accompanied by a large walk-in closet and a double-vanity bath.

The gated entrance provides security and privacy, while the absence of a Community Development District (CDD) fee is a meaningful financial advantage compared to many newer Kissimmee communities. The HOA covers exterior maintenance, giving owners the low-hassle lifestyle that townhome living is designed to deliver — without the CDD surcharge that appears on many competing communities' tax bills.

The community's location is arguably its biggest selling point: The Loop on John Young Parkway is less than a mile away, Flora Ridge Elementary School is approximately one mile from the community entrance, and access to Osceola Parkway and the Florida Turnpike makes Cypress Ridge well-positioned for commuters heading to either Orlando or the Walt Disney World corridor.

Cypress Ridge Location & Connections

Cypress Ridge sits in the northern section of Kissimmee, positioned off West Carroll Street and Pleasant Cypress Circle with a secondary entrance on North Thacker Avenue west of John Young Parkway. The community is bordered to the north and west by established neighborhoods and to the south by Osceola Parkway, giving residents fast access to both the Disney corridor and the Florida Turnpike without navigating through central Kissimmee traffic.

The location sits near the Orange County / Osceola County border, making Cypress Ridge one of the more northerly established Kissimmee addresses — a position that shortens commutes to Orlando's employment centers while retaining the cost advantages of an Osceola County address. The Loop shopping center is under a mile away, and Osceola Parkway connects residents westward to Walt Disney World or eastward to the Florida Turnpike in minutes.

Cypress Ridge Amenities & Lifestyle

Life at Cypress Ridge centers on convenience and low-maintenance living in one of northern Kissimmee's most accessible corridors. With the HOA handling exterior upkeep, residents channel their time into what the area does best: proximity to world-class entertainment, diverse dining, year-round outdoor recreation, and the kind of easy Florida lifestyle that drew them here in the first place.

The community's position near the Orange-Osceola county line gives Cypress Ridge residents an unusual combination of Osceola cost advantages and near-Orange County accessibility. Whether you work in downtown Orlando, commute to Lake Nona's medical complex, or spend weekends at theme parks, Cypress Ridge's address works for a wide range of lifestyles — from young professionals to families drawn by the proximity to Flora Ridge Elementary School.

How Cypress Ridge Compares

Cypress Ridge occupies a distinct niche in the Kissimmee townhome market: a gated, Ryan Homes-built community with no CDD fee, a true resort-style pool, and a sold-out resale market that signals strong demand. Buyers comparing Cypress Ridge against other Kissimmee townhome options will find meaningful differences in age, amenities, and cost structure.

The no-CDD advantage is particularly notable — many newer communities in this corridor carry CDD assessments that add hundreds of dollars annually to already robust HOA costs. Cypress Ridge's absence of that fee, combined with its gated security and modern smart-home features, makes it a compelling value proposition for buyers who might otherwise look further afield.

Cypress Ridge HOA & CDD Information

Cypress Ridge is governed by a mandatory Homeowners Association (HOA) that oversees the community's gated entrance, shared amenities, and exterior maintenance standards. The HOA structure is what enables the maintenance-free lifestyle that townhome buyers seek — lawn care, exterior upkeep, and community facilities are handled collectively, freeing residents from individual maintenance responsibilities.

One of Cypress Ridge's most significant financial advantages is its confirmed absence of any Community Development District (CDD) fee. Many competing new-construction communities in Kissimmee and the surrounding area carry CDD assessments that appear as a line item on the annual property tax bill. At Cypress Ridge, there is no such assessment — only the HOA fee covers community operations. Learn more about HOA structures at What's an HOA?

Frequently Asked Questions