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.
Sold for $674,000 on 08/19/25
$674,000
7445 Winding Cypress DR, NAPLES, FL 34114
3beds
2,198sqft
Single Family Residence
Built in 2016
6,969.6 Square Feet Lot
$668,200 Zestimate®
$307/sqft
$5,019 Estimated rent
Owner options
What's special
Zillow last checked: 7 hours ago
Listing updated: August 22, 2025 at 04:51am
Listed by:
Drayton Herold 239-450-2480,
KW Elevate Luxury,
Timothy Logiovino 239-319-2083,
Keller Williams Elevate Luxury
Bought with:
Maurice Cossairt
Edgewater Realty & Homes LLC
Source: SWFLMLS,MLS#: 225050266
Originating MLS: Naples

Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 2
- Full bathrooms: 2
Dining room
- Features: Breakfast Bar, Dining - Living
Kitchen
- Features: Island
Heating
- Central
Cooling
- Ceiling Fan(s), Central Air
Appliances
- Included: Gas Cooktop, Dishwasher, Disposal, Dryer, Grill - Gas, Microwave, Range, Refrigerator/Freezer, Washer
- Laundry: Inside
Features
- Foyer, Pantry, Tray Ceiling(s), Window Coverings, Den - Study, Family Room, Laundry in Residence, Other Additional Rooms, Screened Lanai/Porch
- Flooring: Carpet, Tile
- Windows: Window Coverings, Shutters
- Has fireplace: No
Interior area
- Total structure area: 3,006
- Total interior livable area: 2,198 sqft
Property
Parking
- Total spaces: 2
- Parking features: Driveway, Attached
- Attached garage spaces: 2
- Has uncovered spaces: Yes
Features
- Stories: 1
- Patio & porch: Screened Lanai/Porch
- Exterior features: Outdoor Kitchen
- Pool features: Community
- Spa features: Community
- Has view: Yes
- View description: Lake, Preserve
- Has water view: Yes
- Water view: Lake
- Waterfront features: Lake, Rip Rap
- Frontage type: Lakefront
Lot
- Size: 6,969 sqft
- Features: Regular
Details
- Additional structures: Tennis Court(s), Outdoor Kitchen
- Parcel number: 82679009722
- Other equipment: Generator
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Ranch
- Property subtype: Single Family Residence
Materials
- Block, Stucco
- Foundation: Concrete Block
- Roof: Tile
Condition
- New construction: No
- Year built: 2016
Utilities & green energy
- Gas: Natural
- Water: Central
Community & neighborhood
Security
- Security features: Gated Community
Community
- Community features: Clubhouse, Pool, Dog Park, Fitness Center, Restaurant, Sidewalks, Street Lights, Tennis Court(s), Gated
Location
- Region: Naples
- Subdivision: WINDING CYPRESS
HOA & financial
HOA
- Has HOA: Yes
- HOA fee: $6,676 annually
- Amenities included: Bike And Jog Path, Bocce Court, Clubhouse, Pool, Community Room, Spa/Hot Tub, Dog Park, Fitness Center, Pickleball, Restaurant, See Remarks, Sidewalk, Streetlight, Tennis Court(s), Underground Utility
Other
Other facts
- Road surface type: Paved
Services availability
Sell for more on Zillow
Get a Zillow Showcase℠ listing at no additional cost and you could sell for .
$668,200
2% more+$13,364
With Zillow Showcase(estimated)$681,564