4491 Cutlass Drive, Upper Captiva, FL 33924

$2,800,000

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.… Read More 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. Read Less

Courtesy of Mark Muller, Resort Properties Internationa.

Listing Snapshot

Days Online

Last Updated

Jan 8, 2026

Property Type

SingleFamilyResidence

Beds

Full Baths

Square Ft.

2,514

Lot Size

0.22 Acres

Year Built

2019

MLS Number

2025025176

Additional Details

Property Access

Road frontage type: PrivateRoad, Road responsibility: PrivateMaintainedRoad

Appliances & Equipment

BuiltInOven, Dryer, ElectricCooktop, Freezer, IceMaker, Refrigerator, RefrigeratorWithIceMaker, Washer

Building

Built in 2019, Architectural style: Contemporary, Florida, MultiLevel, Construction materials: Other, WoodFrame, 3 total stories, Toal building area: 3428

Community

NonGated

Cooling

CentralAir, CeilingFans, Electric

Exterior Features

Deck, SecurityHighImpactDoors

Floors

Tile

Garage

1 space

Water Features

None

Heating

Central, Electric

Home Owner's Association

Association amenities: None

Interior Features

Furnished: Partially, BreakfastBar, CathedralCeilings, DualSinks, KitchenIsland, LivingDiningRoom, ShowerOnly, SeparateShower

Laundry

Inside

Lot

0.2152 acres, RectangularLot

Parking

1 covered space, Attached, Garage

Pets Policy

Yes

Pool

AboveGround, Fiberglass, ElectricHeat, Heated

Property

Patio and porch features: Balcony, Deck, Lanai, Porch, Screened, Bay, Gulf, Landscaped, Partial, TreesWoods

Roof

Metal

Sewer

SepticTank

Taxes

Year: 2024

Utilities

CableNotAvailable

Windows

CasementWindows, DisplayWindows, ImpactGlass

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