Countryside Golf & Country Club is one of East Naples' best-known golf communities. It turned 40 in 2026 and just finished a $15 million clubhouse renovation. Listing photos show the fairways. The county's public records show the rest: lien activity, lawsuits, roof permits and the age of the buildings. Here is what we found, and what it means for owners and buyers.
Countryside at a glance
Countryside is a gated community off Santa Barbara Boulevard and Davis Boulevard, a couple of miles from I-75. It has 1,133 residential units, including 221 detached single-family homes. The rest are villas and condos in separate neighborhood associations under one master association.
The master association was registered with the State of Florida in January 1987. The community opened in the late 1980s, and many buildings date from roughly 1988 to 1991. The 18-hole, par-70 course was originally designed by Arthur Hills and was redesigned in 2019.
What the HOA records show
Liens rise and fall with the economy
We counted claims of lien recorded by the master association in the Collier County Clerk's index (no owner names used):
- 2011–2015: 39 liens (peak of 13 in 2013)
- 2016–2020: 15 liens
- 2021–2026 (to date): 12 liens, 7 of them in 2025
The 2025 bump is worth noting: it overlaps the clubhouse construction years. Over the same 2011–2026 period, 46 lien releases were recorded, so most claims were eventually paid.
Lawsuits are rare
Since 2016 the index shows 7 filings by the association against owners, about one every one or two years. Lenders' foreclosure notices naming the association were concentrated in 2012–2014 (17 of 29 since 2012). Only 5 were filed in 2024–2026.
Dues: ask for the current budget
Older lien filings give a clean number. In 2016 the master assessment was $109.13 per quarter; in 2017 it was $111.00, up 1.7%. Newer liens bundle assessments with fees and club charges, so they do not give a reliable current figure. Countryside is a bundled golf community, so your total cost includes the master assessment, your neighborhood association and club dues. Ask for all three in writing.
The rules were rewritten twice
The master association recorded restated governing documents in 2017 (52 pages) and again in March 2025 (49 pages). If you last read the rules years ago, read the 2025 version.
What the permits show
A $15 million clubhouse
County permits line up with the renovation news. A building-addition permit valued at $8 million was issued for the clubhouse in February 2024. Two commercial pool permits ($250,000 and $75,000) followed in February 2025. The club reports the project cost $15 million in total.
A wave of roofs in 2023
In January–March 2023, commercial re-roof permits were issued for at least five condo buildings on Heritage Trail, valued at $43,000–$50,000 each. Older permits show shingle re-roofs from the mid-2000s on some buildings. A roof's age drives insurance today, so check the permit date for your building.
Milestone inspections for condos
Florida now requires structural milestone inspections for condo buildings of three or more stories. In Collier County, the first is due at 25 years (within three miles of saltwater) or 30 years (inland), then every 10 years. The Country Glen Four condominium in Countryside shows "Milestone Completed" in the county system, with its next inspection in 2034. Ask any condo seller for the inspection report.
Age of the homes: what to watch for
Most of Countryside was built in the late 1980s and early 1990s. That era brings a predictable list:
- Polybutylene supply pipe. It was installed from about 1978 to 1995. Chlorine in the water can make it crack and leak. Look for gray pipe marked "PB-2110".
- Original or 20-year-old roofs. Insurers often ask for the roof's age and condition.
- Older windows and shutters. Pre-2000 openings may not meet today's wind-protection expectations.
- 35-year-old A/C ductwork and water heaters. These are often replaced piecemeal, so the permit history is uneven.
Flood and evacuation zones
The Country Glen section we checked is in FEMA flood Zone X (shaded). That means a 0.2% annual chance of flooding, not a high-risk zone. It is in Collier hurricane evacuation Zone C. Zones can differ from one street to the next, so check your own address on the FEMA map and Collier's "Know Your Zone" tool.
What's nearby
From the Country Glen area, a Publix and an Aldi are about a quarter-mile away at Santa Barbara and Davis. Greater Naples Fire Stations 20 and 72 are about 2.2 miles away. Physicians Regional–Collier Blvd is about 3.9 miles away, and NCH downtown about 4.9 miles. For 2026–27, that address is zoned for Calusa Park Elementary, East Naples Middle and Lely High. Confirm zoning for your own address.
Before season or before you buy: a checklist
Paperwork
- Pull the permit history for your unit or building: roof, windows, A/C, plumbing.
- Ask for the roof's age and a wind-mitigation report for insurance.
- For condos, get the milestone inspection and reserve study.
- Get all three costs in writing: master assessment, neighborhood association, club dues.
In the home
- Look under sinks and at the water heater for gray "PB-2110" pipe.
- Test shutters, door seals and sliding-door tracks before storm season.
- Flush the A/C condensate line and change filters before you leave for summer.
- Confirm your flood zone and evacuation zone by address.
FAQ
Is Countryside in a flood zone?
The section we checked is in FEMA Zone X (shaded), which is moderate-to-low risk, not a mandatory-insurance zone. Check your own address on the FEMA Flood Map Service Center.
How old are the homes in Countryside?
The community opened in the late 1980s, and most buildings date from about 1988 to 1991. Plan for typical 35-year-old issues: older plumbing, roofs and windows.
Does the HOA file a lot of liens?
Lien filings peaked in 2013 at 13. In 2021–2026 there were 12 in total, with 7 in 2025. Lawsuits against owners are rare: 7 since 2016.
Related Naples homeowner guides
- Pelican Marsh in Naples, FL: What Buyers and Homeowners Should Know
- Village Walk Naples community guide
- October in Naples: 10 Small Home Repairs to Do Before Season
- Minor plumbing repairs in Naples · Home watch and seasonal checks
Need a hand in Countryside?
QuoteHandyman works across Naples and Collier County. We can help with pre-season checks, plumbing swaps, shutter and door repairs, and small fixes on your inspection list.
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Sources
- Golf Course Industry — Countryside renovation: 1,133 units, 221 single-family homes, 18 holes, par 70
- Greater Naples Chamber — Countryside commemorates 40 years; $15M clubhouse; 2019 course redesign
- Business Observer — Naples country club completes $15M renovation (Jan 2026)
- Naples Condo Boutique — All About Countryside
- Collier County Clerk — Official Records search (liens, lis pendens, restated declarations: OR 5394/2116, OR 6452/861)
- Florida Division of Corporations (Sunbiz) — Countryside Master Association filing, Jan 1987
- Collier County — Milestone Inspections (rules, map, status)
- Collier County GMCD public portal — permit records
- FEMA Flood Map Service Center
- Collier County Emergency Management — evacuation zones
- Collier County Property Appraiser — parcel and sales data
- Waypoint Inspection — What is polybutylene (1978–1995, PB-2110)
Lien, lawsuit and permit counts are our tally of the public Clerk and County indexes as of October 2026; no individual owners are named. Fees, rules and zones change — verify the exact property and current association documents. QuoteHandyman provides handyman and maintenance services within applicable scope; permit-required or licensed-contractor work is referred appropriately.