#225049275, Alex O'Neill, Listing office: Gulf Coast Properties Group
$799,000 List price
7445 Winding Cypress Dr Naples, FL 34114
3 beds
2 full
2,198 sqft
0.2 acres
$364 / sqft
House
Property details
About 7445 Winding Cypress Dr
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, and a fully equipped outdoor kitchen—ideal for entertaining or enjoying peaceful evenings overlooking the lake. 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.
Highlights
Home typeSingle Family Residence
HeatingCentral, Electric
StatusActive
CoolingCentral Air, Ceiling Fan(s), Electric
Size2,198 sqft
Lot size0.16 Acres
Year built2016
ParkingAttached, Driveway, Garage, Paved, Garage Door Opener
MLS #225050266
Attached garage2 spaces
WaterfrontLake Front, Rocky Shoreline
ViewLake, Other
Summary
- Full Bathrooms: 2
- Appliances: Dryer, Dishwasher, Freezer, Gas Cooktop, Disposal, Microwave, Range, Refrigerator, Washer
- Flooring Type: Carpet, Tile
- Interior: Breakfast Bar, Tray Ceiling(s), Dual Sinks, Entrance Foyer, Kitchen Island, Living/Dining Room, Pantry, Shower Only, Separate Shower, Window Treatments, Split Bedrooms
- Total Bedroom Count: 3
- Garage Space: 2 spaces
- Attached Garage: Yes
- Private Pool: No
- Parking: Attached, Driveway, Garage, Paved, Garage Door Opener
- Waterfront: Lake Front, Rocky Shoreline
- View: Lake, Other
- Exterior: Sprinkler/Irrigation, Outdoor Kitchen, Room For Pool, Gas Grill
- Architectural Style: Ranch, One Story
- Heating: Central, Electric
- Cooling: Central Air, Ceiling Fan(s), Electric
- List Price: $799,000
- Price/SqFt: $363
- HOA Amount: $0 Quarterly
- Annual Tax Amount: $4,980
- Tax Year: 2023
- Lot: Rectangular Lot, Sprinklers
- Directions: From Collier Blvd turn into Winding Cypress subdivision (Winding Cypress Blvd). Turn left onto Winding Cypress Dr. Follow as the road curves around; the home will be on your left, after you pass Blackberry Dr.
- Year Built: 2016
- Stories: 1
- Living Area: 2,198 SqFt
- Lot Size: 0.16 Acres
- MLS Number: 225050266
- MLS Name: SWFL
- Office Name: KW Elevate Luxury
- Office Phone: (239) 330-1217
- Office Email: jonesnaples@kw.com
- Listing Agent: Drayton Herold
The data relating to real estate for sale on this website comes in part from the Southwest Florida Multiple Listing Service. The information being provided is for consumers` personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information has not been verified, is not guaranteed, and is subject to change. Real estate listings held by other brokerage firms other are marked with the IDX logo and detailed information about them includes the name of the listing brokers.
Data displayed may be a portion of, and not a complete set of all listings published in the MLS.
Last updated on: 7/2/2025, 6:45:28 AM Eastern. If you have any questions regarding the accuracy of this data, please contact us at help@rockethomes.com.
Price information
Property sales
| Date | Event | Price |
|---|---|---|
| Nov 28, 2016 | Home Sold | $472,250 |
Tax history
| Year | Assessment | Property Tax |
|---|---|---|
| 2023 | $328,781 | $4,980 |
| 2022 | $319,205 | $4,479 |
| 2021 | $309,908 | $4,479 |
| 2020 | $305,629 | $4,502 |
| 2018 | $293,187 | $4,208 |
| 2017 | $287,157 | $4,156 |
History based on county public records data.
Nearby schools
7
Manatee Elementary School
Public District PK-5
1.5 mi
•1880 Manatee Rd
6
Lely Elementary School
Public District PK-5
2.9 mi
•8125 Lely Cultural Pkwy
6
Parkside Elementary School
Public District PK-5
3.0 mi
•5322 Texas Ave
School ratings are a score out of 10, where 10 is the highest and 1 is the lowest.
Neighborhood
The neighbors living near this home have an average income of $63,446. Residents of Naples, FL typically earn between $35k-100k each year. The most common type of family is married, no kids. The majority of residents in this area have high school diploma education.
How much money do the neighbors make?
21%
<35k
58%
35k-100k
18%
100k-200k
3%
200k+
What level of education do the neighbors have?
High School Diploma
Post Secondary Degree
Masters Degree
Doctorate
What types of families live nearby?
36%
Single, No Kids
7%
Single, with Kids
46%
Married, No Kids
11%
Married, with Kids
Are the neighbors home owners or renters?
Home Owners
Renters
How old are people in this area?
10%
<11 yrs old
4%
12-17 yrs old
17%
18-34 yrs old
40%
35-64 yrs old
29%
65+ yrs old
What do the neighbors do for fun?
NASCAR
Hunting
Figure Skating
Where do the neighbors shop?
Bass Pro Shops
Academy Sports & Outdoors
Wal-Mart
Where do the neighbors go to eat?
Hardee's
Jimmy Johns
Applebees
What do the neighbors drive?
GMC
Chevrolet
Ram
What do the neighbors listen to?
Classic Country
New Country
Oldies
All data provided by Home Junction and Claritas
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Frequently asked questions
Living in Naples, FL
Naples provides a range of transportation options, including local bus services with established routes and schedules. The city's layout and infrastructure support a comfortable driving experience, with well-maintained roads and easy access to major highways. While Naples is known for its walkable downtown area, the city also has areas that are more car-dependent. Ride-sharing services are readily available, offering an alternative mode of transportation for residents and visitors alike.
The city is served by a number of educational institutions, including public and private schools that cater to a range of educational needs. Healthcare is well-represented with several hospitals and clinics offering a variety of services from emergency care to specialized treatments. Naples also boasts a rich assortment of retail and dining options, with an emphasis on luxury shopping and gourmet cuisine that mirrors the city's affluent culture.
Naples is celebrated for its upscale ambiance and relaxed coastal living. The community prides itself on its pristine beaches, world-class golf courses, and vibrant arts scene. Annual events such as the Naples Winter Wine Festival and the Mercato Wine & Food Festival highlight the city's appreciation for fine living and culinary excellence.
Naples offers a diverse array of housing options, with a significant emphasis on single-family homes that make up a large portion of the market. These homes often feature Mediterranean and coastal architectural styles, reflecting the city's seaside heritage. Luxury condominiums and villas are also prevalent, providing alternatives for those seeking a maintenance-free lifestyle. The housing market here is dynamic, with a mix of both historic homes and newer developments.
About 7445 Winding Cypress Dr
The listing price of 7445 Winding Cypress Dr property is $799,000.
The property 7445 Winding Cypress Dr is a house located in Naples, Florida, 34114.
Active Listing: 7445 Winding Cypress Dr is For Sale (Active/New) which means the seller is accepting offers.
The nearby schools for 7445 Winding Cypress Dr are: Manatee Elementary School (GreatSchools Rating 7/10), Lely Elementary School (GreatSchools Rating 6/10), Parkside Elementary School (GreatSchools Rating 6/10), Manatee Middle School (GreatSchools Rating 6/10), East Naples Middle School (GreatSchools Rating 7/10), New Beginnings - Naples (GreatSchools Rating 5/10), Lely High School (GreatSchools Rating 5/10), Golden Gate High School (GreatSchools Rating 6/10), Beacon High School (GreatSchools Rating 2/10).
According to the records, the last property tax for 2023 is $4,980 (source: MLS/based on county public records data).
The last sale was on November 28, 2016 for $472,250 (source: MLS/tax record).
The property at 7445 Winding Cypress Dr has 3 bedrooms and 2 bathrooms.
The property 7445 Winding Cypress Dr is 2,198 SqFt (source: MLS/tax record).
The year of construction for 7445 Winding Cypress Dr is 2016.
This home is located at 7445 Winding Cypress Dr in Naples, FL and zip code 34114. This 2,198 square foot home, which was built in 2016, sits on a 0.16 acre lot. Features: 3 bedrooms, 2 bathrooms. It has been listed on Rocket Homes since May 29, 2025 and is currently priced at $799,000.
In June 2025 more than 24 listings in Naples, FL were sold above the asking price. During the same period more than 47 listings were sold at asking price, while more than 580 were sold below. Between May and June 2025, Naples, FL real estate market has seen decrease in the number of listings by 2.4%. In June 2025, listings were on the market for 99 days. During the same period, the median list price in this real estate market was $627,689.
From Rocket Homes Real Estate and based on county public records data.