4491 Cutlass Dr, Upper Captiva, FL 33924
For Sale $2,800,000
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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 cant 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. Its a place where memories are made, traditions begin, and time finally slows down.
Breakfast Bar
Cathedral Ceilings
Dual Sinks
Kitchen Island
Living Dining Room
Shower Only
Separate Shower
None
Taxes: $12,563.35
Tax Year: 2024
Deck
Security High Impact Doors
Built In Oven
Dryer
Electric Cooktop
Freezer
Ice Maker
Refrigerator
Refrigerator With Ice Maker
Washer
Y
Building Description: Contemporary, Florida, Multi Level
MLS Area: Ci02 - Upper Captiva Island
Total Square Footage: 3,428
Total Floors: 3
Water: Well
Construction: Other, Wood Frame
Date Listed: 2025-12-30 14:04:33
Pool: Y
Pool Description: Above Ground, Fiberglass, Electric Heat, Heated
Furnished: Partially
Den: Y
Windows: Casement Windows, Display Windows, Impact Glass
Parking: Attached, Garage
Garage Description: Y
Garage Spaces: 1
Attached Garage: Y
Flooring: Tile
Roof: Metal
Heating: Central, Electric
Cooling: Central Air, Ceiling Fans, Electric
Laundry: Inside
Irrigation: None
Pets: Yes
Sewer: Septic Tank
Lot Desc.: Rectangular Lot
Amenities: None
Listing Courtesy Of: Resort Properties Internationa
homes@northcaptiva.net
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 cant 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. Its a place where memories are made, traditions begin, and time finally slows down.
Property Details
Price: $2,800,000
Sq Ft: 2,514
($1,114 per sqft)
Bedrooms: 5
Bathrooms: 3
Unit On Floor: 1
City: Upper Captiva
County: Lee
Type: Single Family
Development: Castaway Key Unrecorded Subdivision
Acres: 0.22
Virtual Tour/Floorplan: View
Year Built: 2019
Listing Number: 2025025176
Status Code: A-Active
Taxes: $12,563.35
Tax Year: 2024
Garage:
1.00
/
Y
Furnishings: Partially
Pets Allowed: Yes
Interior Features:
Breakfast Bar
Cathedral Ceilings
Dual Sinks
Kitchen Island
Living Dining Room
Shower Only
Separate Shower
Amenities:
None
Financial Information:
Taxes: $12,563.35
Tax Year: 2024
Exterior Features:
Deck
Security High Impact Doors
Equipment:
Built In Oven
Dryer
Electric Cooktop
Freezer
Ice Maker
Refrigerator
Refrigerator With Ice Maker
Washer
View:
Y
Additional Information:
Building Description: Contemporary, Florida, Multi Level
MLS Area: Ci02 - Upper Captiva Island
Total Square Footage: 3,428
Total Floors: 3
Water: Well
Construction: Other, Wood Frame
Date Listed: 2025-12-30 14:04:33
Pool: Y
Pool Description: Above Ground, Fiberglass, Electric Heat, Heated
Furnished: Partially
Den: Y
Windows: Casement Windows, Display Windows, Impact Glass
Parking: Attached, Garage
Garage Description: Y
Garage Spaces: 1
Attached Garage: Y
Flooring: Tile
Roof: Metal
Heating: Central, Electric
Cooling: Central Air, Ceiling Fans, Electric
Laundry: Inside
Irrigation: None
Pets: Yes
Sewer: Septic Tank
Lot Desc.: Rectangular Lot
Amenities: None
Map of 4491 Cutlass Dr, Upper Captiva, FL 33924
Listing Courtesy Of: Resort Properties Internationa
homes@northcaptiva.net