Cypress Falls at The Woodlands

Cypress Falls at The Woodlands is an age-restricted, 55-plus, gated community in North Port, Sarasota County, with a genuinely distinctive and well-documented mixed development history. Construction began in 2005 under original builder Lennar Homes, with roughly 148 homes built between 2005 and 2008 before the community’s development halted entirely during the 2008-2012 national recession, a common fate for many Florida communities launched in that era. Del Webb, the active-adult brand of national homebuilder PulteGroup, took over and resumed development in 2012, eventually adding a newer "Garden Series" phase of single-family homes ranging from 1,372 to 1,968-plus square feet that opened in 2018. Because of this mixed-builder history, prospective buyers researching Cypress Falls at The Woodlands should be aware that some marketing and secondary sources refer to it simply as a "Del Webb" community without clarifying that its earliest homes, built 2005-2008, originated under Lennar rather than Del Webb; this distinction may matter for buyers evaluating construction quality, warranty history, or architectural style differences between the community’s earlier and later phases. The community’s total home count carries a genuine, unresolved discrepancy in the sources reviewed for this research: one source cites roughly 377 homes built between 2005 and 2016, while a separate source in the same research pass cited roughly 710 homes for the community. This research could not reconcile the two figures using the sources available and flags this explicitly as needing direct verification against the community’s official HOA records before being treated as settled fact; 377 is used as the primary figure here as the more specific, consistently repeated number, while acknowledging the higher figure may reflect a more complete final build-out count that this research could not confirm. Housing types include paired villas, garden villas, and single-family homes, with reported sizes of 1,372 to 3,231 square feet across all phases (2-5 bedrooms, 2-3 car garages) according to one source, though a narrower range of 1,372 to 1,968-plus square feet appears to describe specifically the newer 2018 Garden Series phase rather than the community’s full range across all builders and phases. The community’s amenities center on a substantial 23,000-square-foot clubhouse that has operated since 2007, featuring a heated resort pool and a separate resistance pool, a spa, tennis and pickleball courts, bocce courts, a putting green, a ballroom, a library, a billiards room, and a full-time activities director coordinating the community’s social calendar. Cypress Falls at The Woodlands carries a distinctive fee structure relative to many other Del Webb Florida communities: HOA fees are billed quarterly at $820 to $852 (equivalent to roughly $273 to $284 per month), rather than as a flat monthly figure, and a separate Community Development District fee of $907 to $1,438 per year is applied directly via the property tax bill. Buyers should budget for both components together as the community’s true total carrying cost, rather than quoting either figure alone as if it represented the full picture. North Port itself has no hospital located directly within city limits; the nearest facility is a Sarasota Memorial Hospital freestanding emergency room within North Port, with fuller-service hospital care available in neighboring Port Charlotte, Charlotte County. No exact mileage from the community itself to either facility was found in this research. For air travel, Punta Gorda Airport is cited at 17.2 miles, the single most concrete and reliable airport-distance figure identified anywhere in this research pass, while Southwest Florida International Airport in Fort Myers sits roughly 62 miles away; Sarasota-Bradenton International Airport is also described as "within easy reach" without a specific confirmed mileage figure. Cypress Falls at The Woodlands’ genuinely unusual, multi-builder origin story is worth understanding for any buyer evaluating a resale within the community: homes built during the original 2005-2008 Lennar phase may carry different construction specifications, warranty histories, and architectural details than homes built after Del Webb resumed development in 2012, and buyers should ask directly which phase a specific listing belongs to rather than assuming uniform construction quality across the entire, decade-plus development timeline. That said, the community’s substantial 23,000-square-foot clubhouse and its comprehensive recreational amenities, including tennis, pickleball, and bocce courts alongside a heated resort pool and separate resistance pool, give residents a genuinely full active-adult amenity package regardless of which phase their specific home was built in. North Port’s continued growth as one of Southwest Florida’s more affordable coastal-adjacent markets, combined with the community’s quarterly HOA billing structure and separate CDD assessment, makes Cypress Falls at The Woodlands a genuinely distinct option worth comparing carefully against Sarasota and Charlotte County alternatives with more conventional monthly-fee structures.

Age Restriction

Cypress Falls at The Woodlands is an age-restricted, 55-plus, gated community in North Port, Sarasota County, with a genuinely mixed development history. Construction began in 2005 under original builder Lennar Homes, with roughly 148 homes built between 2005 and 2008 before construction halted during the 2008-2012 recession; Del Webb (PulteGroup) took over and resumed development in 2012, later adding a newer "Garden Series" phase that opened in 2018. As a community with mixed-builder history, some marketing and secondary sources refer to it simply as a "Del Webb" community despite its Lennar-originated first phase; this should be clarified when researching the community’s exact ownership history for any given home. Explicit HOPA/80-20 citation by name was not found and should be verified against governing documents.

Housing Types

• Paired villas
• Garden villas
• Single-family homes

Pricing

Cypress Falls at The Woodlands’ total home count carries a genuine, unresolved discrepancy: one source cites roughly 377 homes built between 2005 and 2016, while a separate source in the same research pass cited roughly 710 homes. This research could not reconcile the two figures and flags this as needing direct verification against the community’s official HOA site before being treated as settled; 377 is used here as the more specific, commonly repeated figure, with the caveat that the higher figure may reflect a more complete final build-out count. Housing sizes are reported at 1,372 to 3,231 square feet in one source (2-5 bedrooms, 2-3 car garages) and more narrowly at 1,372 to 1,968-plus square feet in another, the latter apparently describing specifically the newer 2018 "Garden Series" phase rather than the community’s full range across all phases.

Fees & Assessments

HOA Dues: HOA fees run $820 to $852 per quarter, equivalent to roughly $273 to $284 per month, a notably different billing structure than the flat monthly figures quoted for many other Del Webb communities.

CDD Assessment: A separate Community Development District fee of $907 to $1,438 per year is applied via the property tax bill, in addition to the quarterly HOA assessment; buyers should budget for both the HOA and CDD components separately rather than treating either figure in isolation as the community’s full carrying cost.

Amenities

• A 23,000-square-foot clubhouse operating since 2007
• Heated resort pool and a separate resistance pool
• Spa
• Tennis and pickleball courts
• Bocce courts
• Putting green
• Ballroom
• Library
• Billiards room
• Full-time activities director

Getting Around

Healthcare: North Port has no hospital located directly within the city; the nearest facility is a Sarasota Memorial Hospital freestanding emergency room within North Port, with fuller-service hospitals available in neighboring Port Charlotte, Charlotte County. No exact mileage from Cypress Falls at The Woodlands itself was found in this research.

Airport: Punta Gorda Airport (PGD) is cited at 17.2 miles, the most concrete airport-distance figure found in this research. Southwest Florida International Airport (RSW) in Fort Myers is cited at 62 miles. Sarasota-Bradenton International Airport (SRQ) is also described as "within easy reach," though a specific mileage figure for SRQ was not found and should be confirmed directly.