$1,195,000
3 Bed 3 Bath Pool SingleFamilyResidence for Sale in WINDING CYPRESS, FL
7788 Winding Cypress Drive, Naples, FL, 34114
About this home
Nestled within an exclusive gated community and surrounded by a serene nature preserve, this elegant 3-bedroom, 3-bathroom home with a spacious den/office is the epitome of refined Florida living. The open, airy floor plan flows seamlessly, with high ceilings and large windows that capture abundant natural light and offer unobstructed views of the lush preserve behind the home. This home has natural gas, generator, upgraded oversized garage, Sentricon system, central vac system, and many more upgrades. Step into the gourmet kitchen, complete with premium appliances, custom cabinetry, and an expansive island that's perfect for entertaining or family gatherings. Each bedroom is generously sized, featuring high-end finishes and ample storage, while the den/office provides an ideal, private space for working from home or additional relaxation. The master suite is a tranquil retreat with a luxurious en-suite bathroom featuring dual vanities, and a walk-in shower. Outdoors, your private paradise awaits, with a sparkling gas heated salt water pool and spa surrounded by a spacious patio, perfect for sunbathing, al fresco dining, or evening cocktails under the stars. The 3-car garage offers plenty of room for vehicles, storage, and hobbies. Living in this community comes with exceptional amenities that rival a luxury resort. Enjoy an on-site restaurant, a spectacular resort-style pool, tennis courts, pickleball, bocce, and a dog park, all thoughtfully designed to elevate your lifestyle. The well-appointed fitness center, internet café, and an engaging calendar of year-round social events ensure that there's always something to do. Centrally located between the pristine beaches of Marco Island and Naples, this home places you just moments away from world-class shopping, dining, and entertainment, yet offers a peaceful, nature-filled escape in your own backyard. Don't miss the opportunity to make this luxurious haven yours!
Property details
- Type
- SingleFamilyResidence
- Year built
- 2019
- Interior
- 2,496 sqft
- Lot size
- 11,761.2 sqft
- Acreage
- 0.27 acres
- Garage
- 3 car
- Days on market
- 293
- Total association fees
- $6,244/yr (~$520/mo)
- CDD
- None
- Est. taxes (1.4%)
- $16,730/yr
- Flood zone (area est.)
- Not available
- Storm protection
- Impact Windows/Doors, Shutters
- Exposure
- West
- Waterfront
- No
- Gulf access
- No
- Gulf access type
- N/A
- Pool
- Yes
- Spa
- Yes
- 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 3 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 |
|---|---|---|---|---|---|
| 7597 BLACKBERRY Drive | Sep 2025 | $1,175,000 | 3/3 | 2,496 | $471 |
| 7520 Blackberry Drive | Mar 2026 | $1,100,000 | 3/3 | 2,496 | $441 |
| 14574 Regatta Lane | Apr 2026 | $1,205,000 | 3/2 | 2,663 | $452 |
| Average | 3 comps | $1,160,000 | $455 |
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 $575,000 (37.1%) from the original list price.
| Sep 9, 2025 | Sold | $975,000 |
| Aug 7, 2025 | Price reducedfrom $1,250,000 | $1,195,000 |
| Nov 5, 2024 | Listed | $1,550,000 |
The good, the trade-offs & the location
- Built 2019 — post-2002 Florida wind codes (typically lower insurance)
- Private pool
- Storm protection: Impact Windows/Doors, Shutters
- 3-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.