$659,900
3 Bed 2 Bath Pool SingleFamilyResidence for Sale in COUNTRYSIDE, FL
256 Countryside Drive, Naples, FL, 34104
About this home
Live the Dream in Countryside Golf & Country Club! One of Naples’ premier gated communities with a rare blend of privacy, luxury, and convenient coastal living. This property features one of Countryside's largest pool/lanai entertaining areas (over 1,400 sq. ft.) with plenty of privacy thanks to lush vegetation surrounding the pool cage. The rear of this property is adjacent to the golf course, so no worries about a neighboring home backing up to your pool/entertainment area. This property also includes a private, enclosed, pool shower. The home has been lovingly cared for, with attention to detail evident in every corner. Over the past few years, the club has undergone a sweeping transformation: the 18-hole Arthur Hills / Kipp Schulties course was thoughtfully renovated, and the 21,000-square-foot clubhouse was fully refurbished both inside and out. The revamped amenities include indoor and alfresco dining, bars both inside and on the terrace, a resort-style pool with outdoor tiki dining, wellness center and full social calendar. There is no food minimum requirement at the clubhouse, a rare find in country-club living. Countryside is a bundled golf community. The dues structure is known to be among the most affordable in Southwest Florida. And then there’s Naples itself; a city beloved for its sugar-sand beaches, world-class dining, art galleries, championship golf, and vibrant cultural scene. Imagine beach afternoons, strolling elegant Fifth Avenue (just minutes away), and returning home to this private haven. This home is ideally located for proximity to Downtown 5th Avenue, grocery stores, pharmacies, high-end dining and entertainment. You won’t compromise on convenience: you’re just a short drive from the Gulf, I-75, Marco Island, and all the best of Collier County while enjoying a retreat-like residence behind the gates. This is more than just a home - it’s a lifestyle. A place where privacy, elegance, and the very best of Naples converge.
Property details
- Type
- SingleFamilyResidence
- Year built
- 1990
- Interior
- 1,812 sqft
- Lot size
- 7,405.2 sqft
- Acreage
- 0.17 acres
- Garage
- 2 car
- Days on market
- 107
- Total association fees
- $7,504/yr (~$625/mo)
- CDD
- None
- Est. taxes (1.4%)
- $9,239/yr
- Flood zone (area est.)
- Not available
- Storm protection
- None listed
- Exposure
- East
- Waterfront
- No
- Gulf access
- No
- Gulf access type
- N/A
- Pool
- Yes
- Spa
- No
- Natural gas
- No
- Water
- Public
- Sewer
- Public Sewer
- New construction
- No
- Pets
- Call, Conditional
- County
- Collier
Total association fees sums the core association dues the MLS feed provides (HOA, condo/master association, and land lease), normalized to a yearly figure. These are separate from and additional to specialty charges — mandatory club or food-and-beverage minimums, special assessments, and rec-lease fees — which the IDX feed does not carry. Always confirm the full fee schedule with the HOA or listing agent.
Maintenance included in the fee
What the association dues cover, per the MLS. Confirm the full schedule with the HOA.
Amenities
Based on the $/sqft of 9 comparable homes sold nearby in the last 12 months. Indicative, not an appraisal.
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Your notes on this home
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Recently sold nearby
Closed comparable sales within ~1 mile in the last 12 months — similar price, size, beds/baths, and age.
| Address | Sold | Sold price | Beds/Baths | Sq ft | $/sqft |
|---|---|---|---|---|---|
| 96 Glen Eagle Circle | Jul 2026 | $510,000 | 3/2 | 1,992 | $256 |
| 6827 Darby Court | Jun 2026 | $560,000 | 3/2 | 1,629 | $344 |
| 522 COUNTRYSIDE Drive | Apr 2026 | $700,000 | 3/2 | 1,869 | $375 |
| 7809 Stratford Drive | Jul 2026 | $515,000 | 3/2 | 1,675 | $307 |
| 1408 Athol Way | May 2026 | $535,000 | 2/2 | 1,670 | $320 |
| 7750 Haverhill Court | Oct 2025 | $519,900 | 2/2 | 1,813 | $287 |
| Average | 6 comps | $556,650 | $315 |
Market trends — Naples
Median of closed MLS sales each month over the available window. Months with too few sales are omitted; the range extends automatically as more sales close.
Live area medians from the MLS · see all listings. Indicative, not an appraisal.
Price & status history
Down $34,900 (5.2%) from the original list price.
| Jun 30, 2026 | Sold | $640,000 |
| Apr 27, 2026 | Price reducedfrom $674,900 | $659,900 |
| Feb 14, 2026 | Listed | $674,900 |
The good, the trade-offs & the location
- Private pool
- 2-car garage
- Built 1990 — pre-2002 construction may carry older wind codes and higher insurance
Straight-line distances to major SWFL amenities — approximate; actual drive times vary.
Nearby schools
Get more information on their programs, scores, and extracurriculars on each school's page · browse the full schools directory.
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Listing information is provided in part by the Florida Gulf Coast Multiple Listing Service (MLS) through its Broker Reciprocity / Internet Data Exchange (IDX) program. Properties displayed may be listed by brokerages other than SWFL Relocation Team. Data is deemed reliable but is not guaranteed accurate by the MLS or this brokerage and should be independently verified. Fees, flood zones, taxes, square footage, and school assignments are estimates from the feed and must be confirmed. © 2026 SWFL Relocation Team. All rights reserved.