14785 Leeward Drive

Off Market

14785 Leeward Drive

Naples FL 34114

5169 sq. ft.

0.31 ac.

Single-Family

Last sold for $1,395,000

Mike O'Rourke, last sold this property on 10 March 2026 after 500 days on market.

Overview

Discover unparalleled luxury and privacy in this exquisite residence crafted by renowned builder Aston Woods. Nestled on a tranquil cul-de-sac, this home boasts breathtaking long water views, offering a serene escape from the everyday hustle. Experience the allure of the Corfu model, boasting four lavish bedroom ensuites, the fifth bedroom was converted to a built-in office with ensuite. The interior impresses with its meticulous design, introducing a grand great room that features a gourmet kitchen. Here, a gas range, generous island, and ample pantry space create the perfect culinary setting. This culinary haven seamlessly transitions into a spacious dining area and an elegant living room. The primary suite is a sanctuary of comfort, complete with a luxurious bathroom and a walk-in closet, all overlooking the stunning saltwater pool and spa added in 2022. Whether hosting gatherings or enjoying quiet family moments, this outdoor oasis offers endless entertainment possibilities. Upstairs, a living room provides a versatile space for relaxation, surrounded by three additional bedroom suites, ensuring privacy and convenience for guests and family alike. The home’s strategic layout guarantees that every corner of the house balances seclusion with communal spaces. Located just moments from the clubhouse, indulge in world-class amenities including a resort-style pool, lap pool, dining options, dog parks, tennis, pickleball courts, and a children’s playground. Enhance your lakeside lifestyle with the option to drop your own boat in at the community boat ramp and explore the expansive waters of Naples with an EV boat. This home perfectly blends luxury, location, and value — a true gem that promises not to disappoint.

Features

4 bedrooms

5 bathrooms

3 carspaces

3 garage spaces

5169 sq. ft. floor area

0.31 ac. lot size

Single-Family

Estimated Value

Based on this property and similar 4 bedroom single-family properties sold in Naples over the last 12 months, the estimated median property value of 14785 Leeward Drive is $1.2m.

Median value

$1.2m

Estimated value range

$525k - $3.36m

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 14785 Leeward Drive

2026

Sold

$1,395,000

10 Mar 2026 by Mike O'Rourke, of Re/Max Affinity Plus

Happy sellers in Naples

65%

65% 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 24 reviews in Naples over the last 12 months.

Local market activity for 4 bedroom single-family properties in Naples

In the last 12 months, 113 four-bedroom single-family properties similar to 14785 Leeward Drive, have been sold.

This represents a 13% decrease in four-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.