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Castaway Estates Houses For Sale55+ Active Adult

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Castaway Estates, 5885 Pine Tree Dr, Sanibel, Florida 33957, image 1
$950,000 $100K
  • 3 Beds
  • 2 Baths
  • 1,812 SqFt
  • $524/SqFt
House for sale in Castaway Estates
5885 Pine Tree Dr, Sanibel, FL 33957
Welcome to this beautifully remodeled coastal home, ideally located just a short walk to the beach. This turnkey 3-bedroom, 2-bath property is a fisherman’s paradise, featuring a private boat dock with direct access to the gulf, a brand-new pool, and a spacious lot with a two-car garage. Inside, you'll find a cozy living area with a working fireplace—perfect for cool coastal evenings. Completely updated inside and out, the home includes a new roof installed in 2024. Spend your days fishing or boating and your evenings enjoying stunning west coast sunsets near the world-famous beaches of sanibel and captiva.
Castaway Estates, 5810 Pine Tree Dr, Sanibel, Florida 33957, image 1
$1,889,999 $10K
  • 4 Beds
  • 3 Baths
  • 2,929 SqFt
  • $645/SqFt
House for sale in Castaway Estates
5810 Pine Tree Dr, Sanibel, FL 33957
Welcome to your private island retreat on the serene and highly sought-after dinkins bayou, where breathtaking wide water views meet direct boating access to both the gulf and bay. This stunning, elevated home offers over 3, 000 square feet of luxury living across two thoughtfully designed levels, blending elegant coastal style with modern comforts. Step inside to discover a spacious 4-bedroom, 3-bath home filled with natural light, soaring ceilings, and panoramic views from nearly every room. The main level showcases a flowing open-concept design ideal for entertaining, featuring a great room with a gas fireplace, dining area, and a gourmet kitchen—all framed by expansive windows and multiple decks perfect for enjoying sunrise coffees or sunset cocktails. The split floor plan ensures privacy, with guest rooms tucked on opposite sides of the main living space. Upstairs, the expansive primary suite serves as a true sanctuary with private balconies on both sides, a spa-like bath with soaking tub and walk-in shower, and a generous walk-in closet. An additional guest bedroom or office provides flexible space for work or visitors. High-end finishes abound throughout, including brazilian cherry floors, custom woodwork, an elevator, and smart storage solutions. The outdoor living is just as impressive, with a newly resurfaced pool and deck (2023) set within a large screened enclosure—ideal for year-round florida living. Practical upgrades include a new roof (2023), new water heater, new pool pump, ample ground-level storage for your kayaks, paddleboards, and beach gear, plus electric vehicle parking. This exceptional property offers the rare blend of luxury, privacy, and direct waterfront access on the widest part of dinkins bayou—don’t miss your chance to own a slice of island paradise!
Castaway Estates, 5703 Sanibel Captiva Rd, Sanibel, Florida 33957, image 1
$1,650,000
  • 3 Beds
  • 21/2 Baths
  • 2,464 SqFt
  • $670/SqFt
House for sale in Castaway Estates
5703 Sanibel Captiva Rd, Sanibel, FL 33957
Breathtaking views of clam bayou! This waterfront near beach custom home on the west end of sanibel has incredible views, exceptional privacy, and provides an opportunity to enjoy the true majesty of the island. From your private dock, sanibel's spectacular uncrowded gorgeous beaches are accessible by water. Kayaking in the bayou is an amazing way to experience this unique setting, immersed in the untouched splendor of the island. Blind pass beach and bowman's beach are also easily accessed via the bike path. The screened two lane lap pool offers another way to enjoy the water while the expansive screened lanai extends the living space, taking full advantage of this fabulous location. With an architectural style that fully respects this natural setting, concrete, wood, stucco and metal come together to create a resilient work of art. Large rooms, high ceilings, transom windows, wood and tile flooring, and abundant storage make the spaces inviting and hugely functional. Two enclosed garages and an elevator offer convenience while the ground level open air foyer welcomes guests with a one of a kind shell fountain. Inspired by the natural environment that surrounds it, this home is perfectly sanibel.
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Castaway Estates, 5801 Sanibel Captiva Rd, Sanibel, Florida 33957, image 1
$1,500,000 $100K
  • 2 Beds
  • 21/2 Baths
  • 1,566 SqFt
  • $958/SqFt
House for sale in Castaway Estates
5801 Sanibel Captiva Rd, Sanibel, FL 33957
Fully remodeled, custom-built, and offered fully furnished turnkey, this ultimate vacation retreat captures the rare feeling of being blissfully cast away—where a long, winding driveway lined with swaying palms gently disconnects you from the outside world. Sunsets unfold beautifully over clam bayou with the gulf beyond, and direct water access makes this property exceptionally special—launch a kayak or boat from your private dock and reach one of sanibel’s most secluded beaches in minutes, a truly rare island experience. Thoughtfully rebuilt from the ground up, the home’s architecture embodies an organic coastal modern aesthetic—entirely rebuilt to perfection and stunning inside and out—with clean, intentional lines softened by warm, natural materials inspired by the surrounding coastal environment. Designed for effortless enjoyment, the property offers incredible privacy, a spacious lot approximately 360 feet in length, and mature tropical landscaping that reinforces the feeling of an instant island getaway with simple, very low-maintenance living. The backyard sparkles as the sun reflects off the bayou waters. Inside, soaring ceilings and abundant natural light create an airy, relaxed coastal ambiance, while exceptionally refined designer finishes reflect thoughtful craftsmanship throughout. All windows and doors are impact-rated, and a commercial-grade standing seam metal roof provides lasting durability and peace of mind. A screened porch sets the stage for sunset dining, while the back deck off the kitchen enjoys prized southwestern exposure—ideal for sunbathing, entertaining, or unwinding as the day fades. Wildlife sightings are part of everyday life, from bald eagles and ospreys overhead to endless fishing just steps from your door. Blissfully secluded yet just a short bike ride to captiva, this is a truly rare opportunity to own a refined organic coastal retreat where architecture, nature, and island luxury exist in effortless harmony.
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Frequently Asked Questions

The single_family_home dues at Castaway Estates cover: Street Maintenance, None, Sewer.

Castaway Estates Castaway Estates is a pet-friendly “Dogs and Cats OK” subdivision for both owners and tenants. Please note that pet policies may change at the discretion of management and/or the Homeowners' Association (HOA) and may not apply to renters. Restrictions may apply to certain breeds, and size and weight limits may be in place.

Castaway Estates Interior features include: Foyer, Laundry Tub, Pantry, Volume Ceiling, Walk-In Closet(s), Window Coverings, Built-In Cabinets, Foyer, Smoke Detectors, Vaulted Ceiling(s), Fireplace, French Doors, Cathedral Ceiling(s), Laundry Tub, French Doors, Closet Cabinets, Volume Ceiling, Vaulted Ceiling(s), Fireplace, Smoke Detectors, Built-In Cabinets

Castaway Estates unit views: Canal, Mangroves, Landscaped Area, Partial Gulf, Preserve, Basin, Canal, Water, Mangroves, Partial Gulf, Gulf, Gulf, Bay, Landscaped Area

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Scores
Walk Score®
Car-Dependent. Almost all errands require a car.
4

100
Transit Score®
Minimal Transit. It is possible to get on a bus.
0

100
Bike Score®
Bikeable. Some bike infrastructure.
62

100
Sound Score®
Very loud.
0

100
Sanibel
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