4491 Cutlass DR, Upper Captiva FL 33924

$2,800,000

  • 2514 sqft
  • 5 Beds
  • 3 Baths
  • 1 Garages

General Information

  • List Price : $2,800,000
  • City : Upper Captiva
  • Acres : 0.2152
  • MLS Area : 3428
  • Status Type : Resale Property
  • Approx. Living Area : 2514
  • Furnished : Partially
  • Date Created : 2025-12-30
  • MLS Number : 2025025176
  • State Or Province : FL
  • Subdivision : CASTAWAY KEY UNRECORDED SUBDIVISION
  • County : Lee
  • Bedrooms : 5
  • Approx. Total Area : 3428
  • Year Built : 2019
  • Potential Short :
  • DOM : 0
  • Address : 4491 Cutlass DR, Upper Captiva FL 33924
  • Postal Code : 33924
  • Development : Array
  • Property Type : Residential
  • Bath Full : 3
  • Price per Sq Ft : $299
  • Property Id : 05-45-21-17-00005.0080
  • Status : Active
  • CDOM : 0

Description

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.

Provided by Resort Properties Internationa

Detailed Property Information

  • Ownership : Single Family
  • Waterfront Y/N :
  • Boat Access : None
  • Cooling : Ceiling Fan(s), Central Electric
  • Kitchen : Island
  • Amenities : None
  • Restrictions : No Commercial
  • Building Design :
  • View : Landscaped Area, Partial Bay, Partial Gulf, Trees/Woods
  • Waterfront Desc : None
  • Elementary School :
  • High School :
  • Floor Plan Type : Great Room
  • Private Pool Y/N : 1
  • Bedroom Desc :
  • Equipment : Cooktop - Electric, Dryer, Refrigerator/Freezer, Refrigerator/Icemaker, Wall Oven, Washer
  • Additional Rooms : Balcony, Den - Study, Guest Bath, Guest Room, Laundry in Residence, Screened Lanai/Porch
  • Storm Protection : Impact Resistant Doors, Impact Resistant Windows
  • Building Features :
  • Community Type : Non-Gated
  • Gulf Access Y/N :
  • Gulf Access Type :
  • Middle School :
  • Pets : Yes
  • Heating :
  • Windows :
  • Flooring : Tile
  • Private Spa Y/N :
  • Dining Desc : Breakfast Bar, Dining - Living
  • Exterior Features : Balcony, Screened Lanai/Porch

Unit / Building Information

  • Unit Floor : 1
  • Unit Number :
  • Construction : Wood Frame
  • Total Floors : 3
  • Units in Building : 1
  • Elevator : None
  • Building Desc : Contemporary, Florida, Multi-Story Home
  • Units in Complex : 1
  • Roof : Metal

Lot Information

  • Rear Exposure : S
  • Range :
  • Sewer : Septic Tank
  • Lot Unit :
  • Section :
  • Irrigation : None
  • Block : 5
  • Township :
  • Water : Well
  • Lot Desc : Regular

Financial Information

  • Condo Fee : 0
  • Approval :
  • Tax Year : 2024
  • Condo Fee Freq :
  • Management : None
  • Possession : Array
  • Tax Desc :
  • Maintenance : None

Additional Details

  • Amenities : Island
  • County Or Parish : Lee
  • Foreclosed REOYN :
  • Gulf Access YN :
  • Irrigation : None
  • Legal Unit :
  • Lot Type :
  • Management : None
  • Master HOA Fee Freq :
  • Original List Price : 2800000
  • Parcel Number : 05-45-21-17-00005.0080
  • Planned Use :
  • Postal Code Plus :
  • Property Type : Residential
  • Restrictions : No Commercial
  • Section :
  • Source of Measurements :
  • State Or Province : FL
  • Street Dir Prefix :
  • Street Number : 4491
  • Sub Condo Name :
  • Unit Number :
  • View : Landscaped Area, Partial Bay, Partial Gulf, Trees/Woods
  • Waterfront YN :
  • CDOM : 0
  • Close Date :
  • Community Type : Non-Gated
  • Date Created : 2025-12-30
  • Full Address : 4491 Cutlass DR, Upper Captiva FL 33924
  • Last Change Timestamp : 2025-12-30T19:04:33.583Z
  • List Price : $2,800,000
  • Lot Unit :
  • Mandatory Club Fee Freq :
  • MLS Area Major : CI02 - Upper Captiva Island
  • Photo Count : 50
  • Possession : Array
  • Potential Short Sale YN :
  • Range :
  • Road :
  • Sewer : Septic Tank
  • Status : Active
  • Street Dir Suffix :
  • Subdivision Info : CASTAWAY KEY UNRECORDED SUBDIVISION
  • Table : Residential
  • Township :
  • Water : Well
  • Zoning Code: RS-1
  • Association Mngmt Phone : (239) 395-2214
  • Boat Access : None
  • Canal Width : $None
  • City : Upper Captiva
  • Condo Fee : 0
  • Condo Fee Freq :
  • Current Price : $2,800,000
  • DOM : 0
  • Elevation :
  • Gulf Access Type :
  • Master HOA Fee Freq : 0
  • Land Lease Fee Freq :
  • Last Change Type : New Listing
  • Legal Desc :
  • Maintenance : None
  • Mandatory HOA Y/N : 0
  • Matrix Modified DT : 2025-12-30T19:46:32.132Z
  • MLS Number : 2025025176
  • Other PI Ds :
  • Photo Modification Timestamp : 2025-12-30T19:20:48.551Z
  • Postal Code : 33924
  • Price Per Acre : 13,011,152
  • Rear Exposure : S
  • Room Count : 0
  • Source of Measure Lot Dimensions :
  • Status Type : Resale Property
  • Street Name : Cutlass
  • Street Suffix : DR
  • Tax Desc :
  • Tax Year : 2024
  • Trees :
  • Utilities Available :
  • Waterfront Desc :
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4491 Cutlass DR, Upper Captiva FL 33924

$2,800,000