$599,900
3 Bed Pool Home for Sale in Winding Cypress
7156 Live Oak Drive, Naples, FL, 34114
About this home
Welcome to your private paradise in the highly sought-after, resort-style community of Winding Cypress! This TURNKEY FURNISHED true 3-bedroom, 2-bathroom villa offers the ultimate blend of luxury, comfort, and effortless living is move-in ready for your immediate enjoyment. The 2-car attached garage—complete with convenient overhead storage racks and additional utility sink—offer great convenience. Discover a bright, open-concept living space featuring seamless tile flooring throughout. The spacious great room flows effortlessly into your own private outdoor oasis. The enlarged screened lanai offers you enjoyment of a private pool and outdoor grill kitchen, located on a exceptionally private lot that offers a serene, peaceful retreat for relaxation or entertaining. The owner’s suite serves as a tranquil escape, boasting elegant tray ceilings and an ensuite bath complete with a dual-sink vanity, a walk-in shower, a linen closet, and a generous walk-in closet. Two additional bedrooms provide ample space and privacy for visitors and guests. Key upgrades and features include: Brand-NEW HVAC Unit for year-round comfort and energy efficiency. Storm Smart ELECTRIC STORM SHUTTERS on the rear lanai. ACCORDION SHUTTERS on all exterior windows for ultimate peace of mind and storm protection. Winding Cypress is renowned for its world-class amenities, including a resort-style pool, a resident-only restaurant, pickleball, tennis, bocce, a state-of-the-art fitness center, two dog parks, and a vibrant social calendar. Perfectly positioned just minutes from the award-winning beaches of both Naples and Marco Island, as well as shopping, dining, and entertainment, this property is an ideal choice for a full-time residence, a seasonal retreat, or a savvy investment option. Don't miss this rare opportunity to live the Florida dream!
Property details
- Type
- Attached
- Year built
- 2015
- Interior
- 1,554 sqft
- Lot size
- 5,662.8 sqft
- Acreage
- 0.13 acres
- Garage
- 2 car
- Days on market
- 25
- Total association fees
- $5,764/yr (~$480/mo)
- CDD
- Yes
- Est. taxes (1.4%)
- $8,399/yr
- Flood zone (area est.)
- Not available
- Storm protection
- Shutters
- Exposure
- Southeast
- Waterfront
- No
- Gulf access
- No
- Gulf access type
- N/A
- Pool
- Yes
- Spa
- No
- Natural gas
- Yes
- 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 3 comparable homes sold nearby in the last 12 months. Indicative, not an appraisal.
Seeing several homes? Build a tour and we'll route it for you.
Your notes on this home
Keep private notes on this home, what you love, what to ask about, saved to your account and shared with your agent.
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 |
| 7255 Live Oak Drive | Apr 2026 | $599,900 | 2/2 | 1,659 | $362 |
| 7121 Live Oak Drive | Jun 2026 | $580,000 | 2/2 | 1,554 | $373 |
| Average | 3 comps | $591,633 | $363 |
Market trends, Winding Cypress
Live community medians from the MLS · see all listings. Indicative, not an appraisal.
The good, the trade-offs & the location
- Built 2015 — post-2002 Florida wind codes (typically lower insurance)
- Private pool
- Storm protection: Shutters
- 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.
Similar homes nearby
$575,000
MLS# 22602141514695 Edgewater Circle, Naples, FL, 34114
$699,000
MLS# 22602324215160 Sacile Street, Naples, FL, 34114
$539,000
MLS# 2260299707677 Rozzini Lane, Naples, FL, 34114
$679,000
MLS# 2260117605272 Myrtle Lane, Naples, FL, 34113
$599,900
MLS# 2260300167674 Jacaranda Lane, Naples, FL, 34114
$649,000
MLS# 2260014084198 Royal Wood Boulevard, Naples, FL, 34112
Similar communities
Matched by amenities, price tier, and location to Winding Cypress.
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.