7445 Winding Cypress DR, NAPLES, FL 34114
Home value
$654,700
$583,000 - $733,000
$5,019/mo
Owner options
$5,019/mo
Rent Zestimate®
Find your next renter with Zillow Rental Manager. Plus, with online applications, you can quickly screen prospective tenants – for free.
$5,019/mo
Rent Zestimate®
$10,828/mo
Est. payment
Refinancing to a lower rate could help reduce your monthly payments and save thousands over the life of the loan.
$10,828/mo
Est. payment
Explore your selling options
Work with a Zillow partner agent
Leverage their expertise and Zillow's premium Showcase listings to get your home seen by more buyers.
Get startedList with your own agent
Get your home in front of millions of buyers by listing it on Zillow.
Learn how to do itSell it yourself
Take full control of how buyers see your home on Zillow by listing For Sale by Owner (FSBO).
List your homeWhat's special
Zillow last checked:
Listing updated:
Drayton Herold 239-450-2480,
KW Elevate Luxury,
Timothy Logiovino 239-319-2083,
Keller Williams Elevate Luxury
Maurice Cossairt
Edgewater Realty & Homes LLC
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 2
- Full bathrooms: 2
Rooms
- Room types: Den - Study, Family Room, Other, Screened Lanai/Porch, 3 Bedrooms Plus Den
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 Square Feet
- 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 & HOA
Community
- Features: Clubhouse, Pool, Dog Park, Fitness Center, Restaurant, Sidewalks, Street Lights, Tennis Court(s), Gated
- Security: Gated Community
- Subdivision: WINDING CYPRESS
HOA
- Has HOA: Yes
- 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
- HOA fee: $6,676 annually
Location
- Region: Naples
Financial & listing details
- Price per square foot: $307/sqft
- Tax assessed value: $687,334
- Annual tax amount: $4,968
- Date on market: 5/29/2025
- Lease term: Buyer Finance/Cash,FHA,VA
- Road surface type: Paved
Price history
| Date | Event | Price |
|---|---|---|
| 8/19/2025 | Sold | $674,000-12.9%$307/sqft |
Source: | ||
| 8/5/2025 | Pending sale | $774,000$352/sqft |
Source: | ||
| 7/7/2025 | Price change | $774,000-3.1%$352/sqft |
Source: | ||
| 5/29/2025 | Listed for sale | $799,000+69.2%$364/sqft |
Source: | ||
| 11/28/2016 | Sold | $472,250$215/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $5,196 +4.6% | $348,465 +2.9% |
| 2024 | $4,969 +66.6% | $338,644 +3% |
| 2023 | $2,982 -2.6% | $328,781 +3% |
| 2022 | $3,063 -0.9% | $319,205 +3% |
| 2021 | $3,090 +2.4% | $309,908 +1.4% |
| 2020 | $3,016 +1.9% | $305,629 +2.3% |
| 2019 | $2,960 +2.4% | $298,758 +1.9% |
| 2018 | $2,892 -31.3% | $293,187 +2.1% |
| 2017 | $4,208 +1.2% | $287,157 +1004.4% |
| 2016 | $4,157 | $26,000 |
Neighborhood: Winding Cypress
Nearby homes
- $745,0002 bd2 ba1.6k sqft7441 Winding Cypress Dr, Naples, FL 34114Sold

- $1,308,300-- bd-- ba3.9k sqft7449 Winding Cypress Dr, Naples, FL 34114Off Market
- $757,800-- bd-- ba2.6k sqft7437 Winding Cypress Dr, Naples, FL 34114Off Market
- $1,173,8003 bd3 ba2.4k sqft7453 Winding Cypress Dr, Naples, FL 34114Off Market

- $995,1003 bd3 ba2.6k sqft7433 Winding Cypress Dr, Naples, FL 34114Off Market
- $654,1004 bd2 ba2.2k sqft7446 Winding Cypress Dr, Naples, FL 34114Off Market
- $911,700-- bd-- ba3k sqft7442 Winding Cypress Dr, Naples, FL 34114Off Market
- $732,8002 bd2 ba1.6k sqft7450 Winding Cypress Dr, Naples, FL 34114Off Market
Nearby schools
GreatSchools rating
- 7/10Lely Elementary SchoolGrades: PK-5Distance: 2.8 mi
- 7/10Manatee Middle SchoolGrades: 6-8Distance: 1.5 mi
- 5/10Lely High SchoolGrades: 9-12Distance: 3.2 mi
Get pre-qualified for a loan
At Zillow Home Loans, we can pre-qualify you in as little as 5 minutes with no impact to your credit score.An equal housing lender. NMLS #10287.
Sell for more on Zillow
- Florida
- Collier County
- Naples
- 34114
- Winding Cypress
- 7445 Winding Cypress DR