7445 Winding Cypress Drive

Off Market

7445 Winding Cypress Drive

Naples FL 34114

3006 sq. ft.

0.16 ac.

Single-Family

Last sold for $674,000

Drayton Herold, last sold this property on 19 August 2025 after 81 days on market.

Overview

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.

Features

3 bedrooms

2 bathrooms

2 carspaces

2 garage spaces

3006 sq. ft. floor area

0.16 ac. lot size

Single-Family

Estimated Value

Based on this property and similar 3 bedroom single-family properties sold in Naples over the last 12 months, the estimated median property value of 7445 Winding Cypress Drive is $853.33k.

Median value

$853.33k

Estimated value range

$1k - $2.73m

Median days on market

Estimated value trend

increase over the last 12 months

Average days on market is based on recent, comparable sales in Naples. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 7445 Winding Cypress Drive

2025

Sold

$674,000

19 Aug 2025 by Drayton Herold, of Keller Williams LLC

Happy sellers in Naples

62%

62% of sellers in Naples reported that their sale price either exceeded or met their price expectations.

Naples stands out for consistently delivering exceptional satisfaction and strong market results for homeowners.

This is based on voluntary sentiment collected from 15 reviews in Naples over the last 12 months.

Local market activity for 3 bedroom single-family properties in Naples

In the last 12 months, 274 three-bedroom single-family properties similar to 7445 Winding Cypress Drive, have been sold.

This represents a 7% decrease in three-bedroom single-family properties sales when compared to the previous 12 months.

Sold

For Sale

Interested in selling?

People are reaching out to these agents in Naples for a market analysis.

Rosa Byrnes-Warfsman

at BHHS Florida Realty

(21 reviews)

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Carly Swintek

at KELLER WILLIAMS REALTY NAPLES

(10 reviews)

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ML Meade

at Premier Sotheby's International Realty - Marco Island

(27 reviews)

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Marie Orlando

at PREMIERE PLUS REALTY COMPANY

(26 reviews)

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Nearby agents

Compare and contact these top performing agents who’ve delivered exception customer service for their clients in Naples

Rosa Byrnes-Warfsman

Rosa Byrnes-Warfsman is an award winning recommended agent for Naples. They have 12 local sales and collected 18 local reviews across the last 12 months.