$599,900
2 Bed 2 Bath SingleFamilyResidence for Sale in WINDING CYPRESS, FL
7255 Live Oak Drive, Naples, FL, 34114
About this home
This home has just been freshly painted inside and out. professionally painted kitchen and bath cabinets, nice private south waterview , screened lanai able to enlarge or expand with a pool. Previous owner had a great workshop in garage with 8 overhead lights, addition dual media cat5/rg6 charging station for a Tesla , framed peg boards for hanging tools , custom storage cabinets and a pull down staircase for added storage. Home features 2 bedrooms 2 baths plus den a whole house generator and attached manual and electric storm shutters. Remaining furniture in home is staying. Live Oak is a beautiful mature tree lined street on cul de sac and just a short walk to the amenity center, dog park or community garden .Rarely will you find a single family home at this price in Winding Cypress . Great Value ! Winding Cypress amenity center offers so much within its gates, its own Shady Palm restaurant, resort pool , gym , bocci and pickleball courts, dog park , walking trails and so much more. Winding Cypress is a gated community located just mins to 75, downtown and Marco Island. Photos to be uploaded on 1/24
Property details
- Type
- SingleFamilyResidence
- Year built
- 2015
- Interior
- 1,659 sqft
- Lot size
- 7,187.4 sqft
- Acreage
- 0.17 acres
- Garage
- 2 car
- Days on market
- 73
- Total association fees
- $6,648/yr (~$554/mo)
- CDD
- None
- Est. taxes (1.4%)
- $8,399/yr
- Flood zone (area est.)
- Not available
- Storm protection
- None listed
- Exposure
- South
- Waterfront
- No
- Gulf access
- No
- Gulf access type
- N/A
- Pool
- No
- Spa
- No
- Natural gas
- Yes
- Water
- Public
- Sewer
- Public Sewer
- New construction
- No
- Pets
- Yes
- 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 5 comparable homes sold nearby in the last 12 months. Indicative, not an appraisal.
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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 |
|---|---|---|---|---|---|
| 7248 Live Oak Drive | May 2026 | $595,000 | 2/2 | 1,685 | $353 |
| 7121 Live Oak Drive | Jun 2026 | $580,000 | 2/2 | 1,554 | $373 |
| 7370 Mockingbird Court | Dec 2025 | $645,000 | 2/2 | 1,805 | $357 |
| 8612 Genova Court | May 2026 | $599,000 | 3/2 | 1,542 | $388 |
| 7659 Jacaranda Lane | Jan 2026 | $575,000 | 2/2 | 1,544 | $372 |
| Average | 5 comps | $598,800 | $369 |
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 $120,000 (16.7%) from the original list price.
| Apr 30, 2026 | Sold | $599,900 |
| Mar 25, 2026 | Price reducedfrom $639,900 | $599,900 |
| Jan 23, 2026 | Listed | $719,900 |
The good, the trade-offs & the location
- Built 2015 — post-2002 Florida wind codes (typically lower insurance)
- 2-car garage
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.