4 Bed Pool Home for Sale in Winding Cypress
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For SaleMLS# 226024563

$1,400,000

4 Bed Pool Home for Sale in Winding Cypress

7759 Winding Cypress Drive, Naples, FL, 34114

4 beds4.5 baths3,464 sqft3 garage
GatedPickleballTennisBocceFitness CenterClubhouseDog ParkCommunity PoolOn-site DiningWaterfront

Upcoming open house

  • Sun, Sep 61:00 PM, 3:00 PM

About this home

Welcome to one of the most prestigious, stately, and expansive offerings throughout the entire, always-desirable community of Winding Cypress. This exclusive Stonewater Model, with a full 2nd floor of living space, is a DiVosta Builder's flagship luxury home and a very rare find. This property sits on the most exceptional 1/4 acre lot with a spectacular large lake view and full preserve backdrop across the water. Quiet, serene privacy is what you should expect all day long, especially as you witness the incredible early morning sunrises. As soon as you enter the home's grand 2 story foyer via the front double doors, you can't help but notice the opulent main gathering area highlighted by soaring 13 foot ceilings with stylish tray surrounds. With luxury detail, convenience features, and ownership peace of mind everywhere you look, this property has it all. The waterfront, 4+ bedroom, 4 1/2 bath, and 3 car garage with 4 foot extension residence is loaded with custom upgrades. Builder and owner added features include: HURRICANE RESISTANT/IMPACT WINDOWS DOORS & SLIDERS, WHOLE HOUSE GENERATOR, HEATED BUILT-IN POOL W/INTEGRAL SPA, CUSTOM KITCHEN CABINETS W/ABOVE & UNDER CABINET LIGHTING, QUARTZ COUNTERTOPS, UPGRADED APPLIANCE PACKAGE, WALK-IN PANTRY, UPGRADED LANAI W/PICTURE WINDOW SCREEN, HURRICANE RESISTANT ELECTRIC SHADES, POOL BATH, POOL STORAGE ROOM & SUMMER KITCHEN, CUSTOM PLANK TILE THROUGHOUT ENTIRE 1ST FLOOR, EXPANSIVE OWNER'S SUITE W/SITTING AREA, TRAY CEILING, FRENCH DOORS TO HUGE OWNER'S BATH W/DUAL VANITY, EXTENDED WALK-IN SHOWER, MAKEUP VANITY, LARGE WALK-IN CLOSET, BREAKFAST AREA W/CABINETS & BEVERAGE COOLER, DESIREABLE OPEN FIRST FLOOR GATHERING SPACE W/SPECTACULAR HIGH CEILINGS ENCOMPASSING GREAT ROOM, DINING AREA, KITCHEN & BREAKFAST NOOK, GLASS WALL OF DOUBLE SLIDERS THAT OPENS OUT TO LANAI & OUTDOOR LIVING SPACE, UPGRADED LIGHTING AND PLUMBING FIXTURES, 2 OTHER DOWNSTAIRS BEDROOMS CONVERT TO ENSUITES, LAUNDRY CENTER W/CABINETS & CUSTOM TUB, EXPANSIVE 2ND FLOOR LIVING SPACE INCLUDING THE 4TH BEDROOM & FULL BATHROOM, HUGE THEATER/MEDIA ROOM SPACE W/ ADDITIONAL SITTING AREA & WALK-IN CLOSET, BONUS ADDED DEN/OFFICE W/FRENCH DOORS, DUAL ZONED COOLING/HEATING W/2 HVAC UNITS, DESIRABLE 3 CAR EXTENDED GARAGE WITH RUBBER TILE FLOORING & 6 CEILING MOUNTED STORAGE RACKS. Winding Cypress is a most sought after, newer gated community renowned for it's amazing amenities at a great value. Of the total 1250 acres making up the community, Winding Cypress boasts over 825 acres of green space, mature landscape, lakes and preserve. Conveniently located just 15 minutes to downtown Olde Naples, 10 minutes to Marco Island, and 10 minutes to I75, you are close to the best beaches, dining, and boutique shopping that Southwest Florida has to offer.

Property details

Type
SingleFamilyResidence
Year built
2020
Interior
3,464 sqft
Lot size
10,018.8 sqft
Acreage
0.23 acres
Garage
3 car
Days on market
43
Total association fees
$6,583/yr (~$549/mo)
CDD
Yes
Est. taxes (1.4%)
$19,600/yr
Flood zone (area est.)
Yes · High risk (AE)
Storm protection
Impact Windows/Doors, Shutters
Exposure
Northeast
Waterfront
Yes
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

AssociationManagementInternetIrrigationWaterLegalAccountingMaintenanceGroundsMaintenanceStructureRecreationFacilitiesReserveFundRoadMaintenanceStreetLightsSecurity

What the association dues cover, per the MLS. Confirm the full schedule with the HOA.

Amenities

BocceCourtCabanaClubhouseDogParkFitnessCenterLibraryPickleballPoolRestaurantSpaHotTubSidewalksTennisCourts

Flood risk shown is an area-level estimate and can differ from a specific unit's actual FEMA designation (which varies by structure and elevation). Look up this address on the FEMA Flood Map and verify with a licensed insurance agent before relying on it.

At marketThis home is priced in line with comparable recent sales.
This home
$404/sqft
Comp median
$431/sqft
Difference
-6%

Based on the $/sqft of 4 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.

AddressSoldSold priceBeds/BathsSq ft$/sqft
14844 Dockside LaneDec 2025$1,425,0004/43,516$405
9322 Chiasso Cove CourtJul 2026$1,325,0003/33,265$406
3279 Dorado Lane 202Nov 2025$1,527,3253/33,347$456
3290 Dorado Lane 201Jan 2026$1,570,0003/33,347$469
Average4 comps$1,461,831$434

Market trends, Winding Cypress

Median list
$949,900
Median $/sqft
$430
Median sold (90d)
$757,500
Avg days on market
56
Active listings
9
Median sold price · Winding Cypress
$757,500last 3 months19.3% vs $635,000 prior 3 months

Live community medians from the MLS · see all listings. Indicative, not an appraisal.

The good, the trade-offs & the location

Pros
  • Built 2020 — post-2002 Florida wind codes (typically lower insurance)
  • Private pool
  • Waterfront
  • Storm protection: Impact Windows/Doors, Shutters
  • 3-car garage
Consider
  • In a higher-risk flood zone (AE) — flood insurance likely required
Location convenienceHigh
Hospital
9.1 mi
Physicians Regional (Naples)
Beach
10 mi
Naples Pier / Beach
Airport
9.2 mi
Naples Airport
Shopping
10.4 mi
Coastland Center (Naples)

Straight-line distances to major SWFL amenities, approximate; actual drive times vary.

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Nearby schools

Get more information on their programs, scores, and extracurriculars on each school's page · browse the full schools directory.

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.