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4491 Cutlass Drive, 
Upper Captiva, FL 33924

$2,800,000


5

Beds


3

Baths


2,514

Sq Ft


Single Family


Virtual Tour

Active

Listed by

Mark Muller

Resort Properties Internationa

Last updated:

January 14, 2026, 05:00 PM

MLS#

2025025176

Source:

FL GFMB

About This Home

4491 Cutlass Drive

A Legacy Island Estate Designed for La Buena Vida ("the good life").  Some homes impress, and then some homes change your rhythm. Villas in the Air is a spectacular luxury estate created for effortless island living, unforgettable gatherings, and moments that linger long after the sun slips below the horizon. Set on North Captiva Island, this expansive retreat offers a rare balance of scale, privacy, and resort-style amenities—where life slows down and every day feels intentional. From sunrise to sunset, the home unfolds in layers of connection and calm. Mornings begin on the screened terrace with coffee and the sound of distant waves. Afternoons drift by poolside, floating beneath blue skies or gathering at the outdoor bar as laughter carries on the breeze. Evenings rise to the rooftop porch, where a panorama of island views stretches endlessly with sunsets and stars that feel like a private performance just for you. Designed for both togetherness and retreat, the home offers multiple indoor and outdoor living spaces that allow everyone to spread out - yet always reconnect. The main living level stuns with soaring double-story ceilings and an open-concept great room, wrapped in refined contemporary coastal finishes. A restaurant-inspired kitchen anchors the space, connected to multiple dining areas that flow seamlessly indoors and out. Accommodations are generous and thoughtfully planned, offering five distinct sleeping retreats. The primary suite feels like a private sanctuary, complete with a spa-style bath and walk-in rain shower. Two additional king guest rooms share a beautifully appointed bath, while a detached poolside guest suite offers privacy and independence with its own en-suite bath. The third-floor retreat, featuring two queen beds and access to a spacious loft lounge, provides flexibility for guests, media space, or a relaxed sleeping haven. Outdoor living here is nothing short of exceptional. A heated pool, an expansive outdoor bar with TV, a rooftop terrace with panoramic water and preserve views, a grilling area, a wellness space, and multiple entertainment zones transform the property into a true private resort—designed for both quiet escapes and unforgettable celebrations.  Built to later codes with lasting materials like Hardie board siding, impact-resistant windows, a metal roof, composite decking, and aluminum railings. Located on North Captiva Island, a boat-access-only barrier island celebrated for its pristine beaches, shelling, fishing, birdlife, and miles of preserve trails, this estate offers a lifestyle that can't be replicated on the mainland. Villas in the Air is a legacy-quality island estate that is difficult to replicate - ideal as a private family retreat, a high-end luxury rental, or both. This is much more than just your average island home. It's a place where memories are made, traditions begin, and time finally slows down.

Home Facts

Single Family

3 Baths

5 Bedrooms

Built in 2019

Price Summary

2,800,000

$1,113 per Sq. Ft.

MLS #:

2025025176

Last Updated:

January 14, 2026, 05:00 PM

Added:

22 day(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

5

Bathrooms

Total Bathrooms:

3

Full Bathrooms:

3

Interior

Living Area:

2,514 Sq. Ft.


Structure

Structure

Architectural Style:

Contemporary, Florida, MultiLevel

Building Area:

3,428 Sq. Ft.

Year Built:

2019


Finances & Disclosures

Finances

Price:

$2,800,000

Price per Sq. Ft:

$1,113 per Sq. Ft.

Source:FL GFMB
The source of the information about real property available for sale or rent is the copyrighted and proprietary database of the Florida Gulf Coast Multiple Listing Service, Inc.. Copyright 2026 Florida Gulf Coast Multiple Listing Service, Inc.; all rights reserved. The data is provided by the IDX Program, and the Information is Deemed Reliable But Not Guaranteed.

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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.