4491 Cutlass DR Upper Captiva, FL 33924
UPDATED:
Key Details
Property Type Single Family Home
Sub Type Single Family Residence
Listing Status Active
Purchase Type For Sale
Square Footage 2,514 sqft
Price per Sqft $1,113
Subdivision Castaway Key Unrecorded Subdivision
MLS Listing ID 2025025176
Style Resale Property
Bedrooms 5
Full Baths 3
HOA Y/N Yes
Min Days of Lease 7
Leases Per Year 52
Year Built 2019
Annual Tax Amount $12,563
Tax Year 2024
Lot Size 9,374 Sqft
Acres 0.2152
Property Sub-Type Single Family Residence
Source Florida Gulf Coast
Land Area 3428
Property Description
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.
Location
State FL
County Lee
Community Non-Gated
Area Castaway Key Unrecorded Subdivision
Zoning RS-1
Rooms
Dining Room Breakfast Bar, Dining - Living
Kitchen Island
Interior
Interior Features Cathedral Ceiling(s)
Heating Central Electric
Flooring Tile
Equipment Cooktop - Electric, Dryer, Refrigerator/Freezer, Refrigerator/Icemaker, Wall Oven, Washer
Furnishings Partially
Fireplace No
Appliance Electric Cooktop, Dryer, Refrigerator/Freezer, Refrigerator/Icemaker, Wall Oven, Washer
Heat Source Central Electric
Exterior
Exterior Feature Balcony, Screened Lanai/Porch
Parking Features Attached
Garage Spaces 1.0
Pool Above Ground, Fiberglass, Electric Heat
Amenities Available None
Waterfront Description None
View Y/N Yes
View Landscaped Area, Partial Bay, Partial Gulf, Trees/Woods
Roof Type Metal
Porch Deck
Total Parking Spaces 1
Garage Yes
Private Pool Yes
Building
Lot Description Regular
Story 3
Sewer Septic Tank
Water Well
Architectural Style Contemporary, Florida, Multi-Story Home, Single Family
Level or Stories 3
Structure Type Wood Frame
New Construction No
Others
Pets Allowed Yes
Senior Community No
Tax ID 05-45-21-17-00005.0080
Ownership Single Family
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