About Highland Woods
Highland Woods is a gated community of 799 homes in Bonita Springs. Day to day, the nearest golf course, Highland Woods Golf & Country Club, is about 0.1 miles straight-line from the community's center; the nearest library, Bonita Springs Public Library, is about 1.6 miles away; the nearest hospital, NCH Healthcare Bonita, about 2.7 miles.
Amenities — amenities compiled from Highland Woods Golf & Country Club and Bonita Springs market materials (confirm current amenities and membership terms with the club); Highland Woods is a member-owned BUNDLED golf community — include a gated entry, an 18-hole championship golf course designed by Gordon Lewis (bundled — golf membership comes with every home), a clubhouse with casual and formal dining, Har-Tru tennis courts, plus pickleball and bocce, a resort-style community pool, plus satellite pools serving the villages, a fitness center, an active social and events calendar.
On paper, the community sits in evacuation zone A. The average assessed just value across its 842 residential parcels was $509,216 in the county's 2026 roll.
Two features define Highland Woods more than the amenity list. The first is cost structure. Unlike the CDD-financed communities that fill much of the newer Bonita Springs and Estero market, Highland Woods carries no community development district — the sampled 2025 tax bill on an in-community parcel shows only a City of Bonita Springs stormwater assessment and a Lee County solid waste assessment (about $38 combined on that condo unit), not a multi-thousand-dollar CDD line. The second is bundled golf, and it cuts both ways. Because this is a member-owned community where club membership comes with the home rather than being sold as an optional tier, every owner has guaranteed access to the 18-hole Gordon Lewis-designed championship course, which suits people who intend to play; it also means you help fund the member-owned club whether or not you ever tee off. That trade-off is what a prospective buyer should weigh first.
It also helps to understand how Highland Woods is assembled, because the names get confusing on a listing search. Rather than a single subdivision, it is an umbrella of neighborhoods — single-family homes alongside villa, veranda and condominium villages such as the Terrace, the St Andrews Verandas and Heathermoor, roughly 799 residences in all — governed by one master, Highland Woods Golf & Country Club, Inc., whose principal office and common tracts sit inside the community on Highland Woods Blvd. Note that a separately registered "Highland Woods Homeowners Association, Inc." out of Tampa does not own the community's common tracts; the club is the entity whose terms actually apply.
A couple of practical notes for anyone getting serious: the community sits in Evacuation Zone A, so run the county's zone lookup before you commit, and confirm current membership terms, dues, cart options and rules directly with the club before signing anything. This page is an independent, records-based starting point, not affiliated with the HOA, club, or developer.
HOA & community contacts
Southwest Florida Gated Communities is not affiliated with the Highland Woods homeowners’ association or club. Something out of date? Report a correction →
