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 can 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.
Cathedral Ceiling(s)
None
Taxes: $12,563.35
Tax Year: 2024
Balcony
Screened Lanai/Porch
Cooktop - Electric
Dryer
Refrigerator/Freezer
Refrigerator/Icemaker
Wall Oven
Washer
Landscaped Area
Partial Bay
Partial Gulf
Trees/Woods
Building Design: Single Family
Community Type: Non-Gated
MLS Area: Ci02 - Upper Captiva Island
Price per Square Feet: $1,113.76
Total Floors: 3
Water: Well
Construction: Wood Frame
Foreclosure: No
Short Sale: No
Date Listed: 2025-12-30 00:00:00
Pool: Yes
Pool Type: Above Ground, Fiberglass, Electric Heat
Pool Description: Above Ground, Fiberglass, Electric Heat
Private Spa: No
Furnished: Partially
Kitchen Description: Island
Parking: Attached
Garage Description: Attached
Garage Spaces: 1
Flooring: Tile
Roof: Metal
Heating: Central Electric
Cooling: Ceiling Fan(S), Central Electric
Fireplace: No
Storm Protection: Impact Resistant Doors, Impact Resistant Windows
Laundry: Laundry In Residence
Irrigation: None
55+ Community: No
Pets: Yes
Restrictions: No Commercial
Maintenance: None
Rear Exposure: S
Sewer: Septic Tank
Lot Desc.: Regular
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 can 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
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
/
Attached
Furnishings: Partially
Pets Allowed: Yes
Interior Features:
Cathedral Ceiling(s)
Amenities:
None
Financial Information:
Taxes: $12,563.35
Tax Year: 2024
Exterior Features:
Balcony
Screened Lanai/Porch
Equipment:
Cooktop - Electric
Dryer
Refrigerator/Freezer
Refrigerator/Icemaker
Wall Oven
Washer
View:
Landscaped Area
Partial Bay
Partial Gulf
Trees/Woods
Additional Information:
Building Design: Single Family
Community Type: Non-Gated
MLS Area: Ci02 - Upper Captiva Island
Price per Square Feet: $1,113.76
Total Floors: 3
Water: Well
Construction: Wood Frame
Foreclosure: No
Short Sale: No
Date Listed: 2025-12-30 00:00:00
Pool: Yes
Pool Type: Above Ground, Fiberglass, Electric Heat
Pool Description: Above Ground, Fiberglass, Electric Heat
Private Spa: No
Furnished: Partially
Kitchen Description: Island
Parking: Attached
Garage Description: Attached
Garage Spaces: 1
Flooring: Tile
Roof: Metal
Heating: Central Electric
Cooling: Ceiling Fan(S), Central Electric
Fireplace: No
Storm Protection: Impact Resistant Doors, Impact Resistant Windows
Laundry: Laundry In Residence
Irrigation: None
55+ Community: No
Pets: Yes
Restrictions: No Commercial
Maintenance: None
Rear Exposure: S
Sewer: Septic Tank
Lot Desc.: Regular
Amenities: None
Map of 4491 Cutlass Dr, Upper Captiva, FL 33924
Listing Courtesy Of: Resort Properties Internationa
homes@northcaptiva.net