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TOUCHSTONE REAL ESTATE

info@touchstonerealestate.com +1(352) 223-0053

$ 2,800,000

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4491 Cutlass DR Upper Captiva, FL 33924

5 Beds

3 Baths

2,514 SqFt

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 Contemporary,Florida,Multi-Level

Bedrooms 5

Full Baths 3

Construction Status Resale

HOA Y/N No

Year Built 2019

Annual Tax Amount $12,563

Tax Year 2024

Lot Size 9,374 Sqft

Acres 0.2152

Lot Dimensions Appraiser

Property Sub-Type Single Family Residence

Property 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.

Location

State FL

County Lee

Community Castaway Key Unrecorded Subdivision

Area Ci02 - Upper Captiva Island

Direction North

Rooms

Bedroom Description 5.0

Interior

Interior Features Breakfast Bar, Cathedral Ceiling(s), Dual Sinks, Kitchen Island, Living/ Dining Room, Shower Only, Separate Shower

Heating Central, Electric

Cooling Central Air, Ceiling Fan(s), Electric

Flooring Tile

Furnishings Partially

Fireplace No

Window Features Casement Window(s),Display Window(s),Impact Glass

Appliance Built-In Oven, Dryer, Electric Cooktop, Freezer, Ice Maker, Refrigerator, RefrigeratorWithIce Maker, Washer

Laundry Inside

Exterior

Exterior Feature Deck, Security/ High Impact Doors

Parking Features Attached, Garage

Garage Spaces 1.0

Garage Description 1.0

Pool Above Ground, Fiberglass, Electric Heat, Heated

Community Features Non- Gated

Utilities Available Cable Not Available

Amenities Available None

Waterfront Description None

View Y/N Yes

Water Access Desc Well

View Bay, Gulf, Landscaped, Partial, Trees/ Woods

Roof Type Metal

Porch Balcony, Deck, Lanai, Porch, Screened

Garage Yes

Private Pool Yes

Building

Lot Description Rectangular Lot

Faces North

Story 3

Foundation Pillar/ Post/ Pier

Sewer Septic Tank

Water Well

Architectural Style Contemporary, Florida, Multi-Level

Unit Floor 1

Structure Type Other,Wood Frame

Construction Status Resale

Others

Pets Allowed Yes

HOA Fee Include None

Senior Community No

Tax ID 05-45-21-17-00005.0080

Ownership Single Family

Acceptable Financing All Financing Considered, Cash

Disclosures Owner Has Flood Insurance

Listing Terms All Financing Considered, Cash

Pets Allowed Yes

Virtual Tour https://www.propertypanorama.com/instaview/fgcmls/2025025176

Listed by Resort Properties Internationa • Mark Muller

TOUCHSTONE REAL ESTATE

COMPANY OWNER PAGE | BKCQ1051231

+1(352) 223-0053

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4491 Cutlass DR Upper Captiva, FL 33924

Key Details

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Interior

Exterior

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4491 Cutlass DR