$774,000
3 Bed 2 Bath Waterfront SingleFamilyResidence for Sale in WINDING CYPRESS, FL
7445 Winding Cypress Drive, Naples, FL, 34114
About this home
Welcome to this beautifully appointed 3-bedroom, 2-bathroom + den home in the vibrant and sought-after community of Winding Cypress in Naples. Perfectly positioned on a prime lakefront lot, this residence offers serene, long water views that extend to the untouched beauty of the preserve beyond. Thoughtfully designed for both comfort and style, this home features tall interior doorways, an extended screened-in lanai, a fully equipped outdoor kitchen—ideal for entertaining or enjoying peaceful evenings overlooking the lake, and Enjoy the convenience of an extended garage — perfect for extra storage, a workshop space, or oversized vehicles.. Storm shutters provide added security and peace of mind, while the open and versatile layout includes a den perfect for a home office or flex space. The well-appointed kitchen boasts a gas range, catering to culinary enthusiasts, and a natural gas whole-home generator ensures uninterrupted comfort during any weather event. Additional conveniences include an HOA that covers landscaping and irrigation water, allowing for low-maintenance living. Winding Cypress is a gated, resort-style community offering an exceptional array of amenities. Residents enjoy a luxurious clubhouse, a tropical pool with waterfall features, a soothing spa, and a state-of-the-art fitness center. Recreational and social opportunities abound with pickleball, tennis, bocce, and a full calendar of community events. The Shady Palm Café serves delicious food and drinks poolside, while a scenic boardwalk winds through the community’s pristine natural surroundings. A spacious, secure dog park makes this neighborhood perfect for pet lovers as well. Conveniently located just off US-41, Winding Cypress offers easy access to world-class dining, shopping, entertainment, and the white-sand beaches that define Naples living. Experience the perfect blend of privacy, luxury, and vibrant community life in this exceptional home.
Property details
- Type
- SingleFamilyResidence
- Year built
- 2016
- Interior
- 2,198 sqft
- Lot size
- 6,969.6 sqft
- Acreage
- 0.16 acres
- Garage
- 2 car
- Days on market
- 68
- Total association fees
- $6,236/yr (~$520/mo)
- CDD
- None
- Est. taxes (1.4%)
- $10,836/yr
- Flood zone (area est.)
- Not available
- Storm protection
- Shutters
- Exposure
- Northeast
- Waterfront
- Yes
- Gulf access
- No
- Gulf access type
- N/A
- Pool
- No
- 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.
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 |
|---|---|---|---|---|---|
| 7451 Blackberry Drive | Aug 2025 | $885,000 | 3/2 | 2,188 | $404 |
| 7355 Mockingbird Court | Dec 2025 | $875,000 | 3/2 | 2,198 | $398 |
| 7211 Live Oak Drive | Mar 2026 | $835,000 | 3/2 | 2,230 | $374 |
| 6902 Winding Cypress Drive | May 2026 | $835,000 | 3/2 | 2,084 | $401 |
| 7049 Live Oak Drive | Nov 2025 | $800,000 | 3/2 | 2,230 | $359 |
| 14486 STERN Way | Dec 2025 | $750,000 | 4/2 | 2,046 | $367 |
| Average | 6 comps | $830,000 | $384 |
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 $125,000 (15.6%) from the original list price.
| Aug 19, 2025 | Sold | $674,000 |
| Jul 7, 2025 | Price reducedfrom $799,000 | $774,000 |
| May 29, 2025 | Listed | $799,000 |
The good, the trade-offs & the location
- Built 2016 — post-2002 Florida wind codes (typically lower insurance)
- Waterfront
- 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
$623,000
MLS# 2260126208438 Volaro Way, Naples, FL, 34114
$660,000
MLS# 225071390322 Indies Drive 102, Naples, FL, 34114
$650,000
MLS# 225071355309 Indies Drive 102, Naples, FL, 34114
$850,000
MLS# 2250844253123 Aviamar Circle 201, Naples, FL, 34114
$644,683
MLS# 2260034381833 Summerlit Avenue, Naples, FL, 34114
$699,319
MLS# 2260063481845 Summerlit Avenue, Naples, FL, 34114
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.