Captiva Residential Houses Sold

Ultra Luxury
Ultra Luxury
Above $1,000 per SqFt
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Sold - Apr 9, 2026
Captiva Residential, 16891 Captiva Dr, Captiva, Florida 33924, image 1
$3,125,000 $875K
  • 3 Beds
  • 31/2 Baths
  • 3,028 SqFt
  • $1,032/SqFt
Ultra Luxury
House sold in Captiva Residential
16891 Captiva Dr, Captiva, FL 33924
Discover the ultimate artist retreat with this exceptional 1.4-acre bay front estate parcel on captiva’s coveted roosevelt channel. Nestled among lush, mature vegetation, this property offers breathtaking waterfront views, abundant wildlife, and a private dock with direct access to the intracoastal waterway and gulf of mexico. Your picturesque estate also offers a deeded beach access through a scenic walkway to the gulf of mexico across captiva drive. Main residence: • fully remodeled 3-bedroom, 3-bath home • impact glass windows & metal roof for modern safety & efficiency • private pool & spa for island-style relaxation • charming coastal-inspired interiors with elegant finishes art studio & guest retreat: • distinctive architectural design • second-level space with potential for future expansion • a tranquil creative space or additional guest quarters surrounded by nature, this estate offers a serene sanctuary where you can experience manatees, dolphins, and incredible birdlife right in your backyard. A rare opportunity to embrace the captiva island lifestyle with privacy, charm, and endless waterfront adventures. Ground level home that did not flood in any of the recent storms........Schedule your private showing today!
Sold - Jul 7, 2025
Captiva Residential, 15155 Wiles Dr, Captiva, Florida 33924, image 1
$1,600,000 $140K
  • 3 Beds
  • 2 Baths
  • 1,600 SqFt
  • $1,000/SqFt
Ultra Luxury
House sold in Captiva Residential
15155 Wiles Dr, Captiva, FL 33924
Welcome to "wade on in, " a beautifully remodeled captiva island retreat and prime investment opportunity with proven success in weekly rentals. Previously known as "on the wiles side, " this home features lush, tropical landscaping that complements the island setting. Just a 2-minute stroll to captiva beach, the open floor plan boasts vaulted ceilings, an inviting kitchen, and a spacious master suite with well-appointed guest rooms. Outside, the large pool area is a private oasis with lounge seating, a dining area, and grill. Enjoy corn hole or relax on pool floats, then transition to the screened front porch for a cool drink. It’s equipped for a turnkey beach experience, including beach chairs, umbrellas, a wagon, and toys for the kids. With shops and restaurants a short walk or golf cart ride away, "wade on in"embodies the best of captiva living and offers exceptional rental income potential.
Pending
Captiva Residential, 16475/95 Captiva Dr, Captiva, Florida 33924, image 1
$4,995,000
  • 3 Beds
  • 31/2 Baths
  • 6,398 SqFt
  • $781/SqFt
Ultra Luxury
House for sale in Captiva Residential
16475/95 Captiva Dr, Captiva, FL 33924
For the first time ever, two contiguous bayfront parcels are being offered together to create an extraordinary 5-acre waterfront compound along the coveted roosevelt channel on captiva island. Boasting nearly 350 feet of water frontage, three private docks, direct gulf access, and exceptional privacy, this is one of the largest and most significant residential offerings to come to market on captiva island in generations. Set behind a gated entrance and surrounded by unspoiled island beauty, the custom-built residence, recently freshly painted, captures the warmth and character of refined island living. Soaring beamed ceilings, rich wood flooring, and a dramatic beacon tower fill the great room with natural light, while thoughtfully designed living spaces create an atmosphere equally suited for elegant entertaining and relaxed waterfront living. The home features an inviting kitchen designed for gathering and entertaining, a formal dining room, private study, flexible guest accommodations, and two expansive ensuite retreats. A dedicated wellness wing elevates the lifestyle experience with a travertine-lined indoor pool, fitness room, and sauna. Outdoors, the estate unfolds into a truly resort-inspired setting with three private docks, direct gulf access, a tennis court, bocce court, rooftop hot tub, bayfront firepit, and expansive tropical grounds designed for recreation, privacy, and connection to the water. A spacious three-car air-conditioned garage with workshop provides ample room for vehicles, storage, and waterfront essentials. Included in the offering is the adjacent 1.5-acre bayfront parcel, bringing the total property size to nearly 5 contiguous acres and creating a rare opportunity to enjoy the estate as it exists today or further elevate the property into a truly world-class legacy compound. Concept plans by mhk architecture have already been prepared, presenting the opportunity to thoughtfully expand the existing residence or design an entirely new architectural estate. In addition to the plans, recent surveys have been completed along with an updated elevation certificate for the residence, located in desirable flood zone x. The property has never flooded, enhancing peace of mind while offering meaningful time and cost savings throughout the planning and design process. With no hoa restrictions, extraordinary scale, direct gulf access, and unmatched privacy, this is a truly irreplaceable captiva island estate offering.
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Subdivision Amenities

Bike Storage
Internet Access
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Storage
Tennis Court(s)
Beach - Private
Beach Access
Bocce Court
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Nearby Subdivisions

(0.45 miles)
For Sale (6)
$995K - $33.9M
(0.69 miles)
For Sale (1)
$1.6M - $1.6M
(0.83 miles)
For Sale (1)
$3.2M - $3.2M

Schools

Scores

Walk Score®
Car-Dependent. Almost all errands require a car
10

100
Bike Score®
Somewhat Bikeable. Minimal bike infrastructure
44

100
Sound Score®
Bearable noise
83

100
Airport Score
Close to airports. Noticeable airport activity
0

100
Traffic Score
Congested area. Frequent traffic delays
20

100
Local Score
Limited local amenities nearby
0

100

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