Castaway Key Real Estate Sold

Mid-Tier
Mid-Tier
$400 - $650 per SqFt
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Sold - Sep 26, 2025
Castaway Key, 4460 Smugglers Dr, Upper Captiva, Florida 33924, image 1
$1,350,000 $145K
  • 4 Beds
  • 3 Baths
  • 2,358 SqFt
  • $573/SqFt
Mid-Tier
House sold in Castaway Key
4460 Smugglers Dr, Upper Captiva, FL 33924
Just move right in to this fully remodeled, turn-key, luxury north captiva estate home with pool!  This four-bedroom, three-bath island gem offers elegance, space, comfort, and modern design.  The great room features an expansive tv area, dining area, luxury kitchen, and a large sundeck with grilling/dining areas overlooking the huge private heated pool.   Reminding you of every shade of blue shimmering in the waters along the beach and sunny captiva skies, this chef's kitchen will impress you with all new stainless steel appliances, custom-designed cabinetry, glistening white solid surface countertops, and an island layout with a built-in dining bar. Just off the living space is a convenient guest bedroom surrounded by windows and beautiful views of the swaying palm trees. A full bath with a custom tile shower and glass door enclosure is just around the corner for convenient access from the living room and upstairs guests. The primary suite is a true retreat with a private sun deck, spa-like en suite bath, a stunning freestanding oval soaking tub set in a bay window alcove, a custom mosaic-tiled walk-in shower, and dual vanities. The other two guest bedrooms and guest bath on that level offer plenty of sleeping spaces for large families or groups.  The outdoor entertainment area is a true oasis, boasting a giant pool, poolside tv area, pool bar, and outdoor shower.  Perfect for entertaining or just unwinding in paradise. Clad with hardie board and upgraded with new impact-resistant windows, sliding glass doors, and a standing seam aluminum roof, this home is built for beauty and resilience. It is just a short walk or golf cart ride from pristine beaches, the ferry, and the resort area.  This home feels like a new home and is priced far below construction value.  Fantastic potential to generate high rental revenue.  This house is a must-see if you have been looking for a newer, larger pool home.  An excellent opportunity to combine family vacation fun with high rental revenue while you are away!
Sold -
Castaway Key, 4430 Smugglers Dr, Upper Captiva, Florida 33924, image 1
$85,000
  • 0.33 Acres
  • $257,576/Acre
Mid-Tier
Land sold in Castaway Key
4430 Smugglers Dr, Upper Captiva, FL 33924
Oversized corner lot bordering rum rd.  Just steps from club amenities, shopping, dining, and the ferry landing. Bay and harbor views from the highest levels!    2 adjacent lots on schooner dr. Also available. Make an offer today!
Pending
Castaway Key, 631 Rum Rd, Upper Captiva, Florida 33924, image 1
$1,495,000 $100K
  • 3 Beds
  • 4 Baths
  • 1,920 SqFt
  • $779/SqFt
Mid-Tier
House for sale in Castaway Key
631 Rum Rd, Upper Captiva, FL 33924
Your private island waterfront escape — where every sunrise feels like it’s just for you! Imagine waking up to the first blush of sunrise spilling over pine island sound, the sky glowing pink and gold, while you sip coffee on your upper deck with panoramic views over a protected nature preserve. Just the soft rustle of palm fronds, the call of shorebirds, and the quiet lapping of water against your private dock. This isn’t just a house — it’s a 4-sleeping room, 4-bath sanctuary built in 2020 to the highest storm and structural codes, so you can relax knowing your island retreat is as strong as it is beautiful. Inside, light pours in through vaulted ceilings onto airy, coastal-inspired living spaces. The designer kitchen — quartz countertops, stainless appliances, and custom cabinetry — was made for both sunset dinner parties and barefoot brunches after a morning swim. Built with impact windows, hardie board siding, and a metal roof, this home is built to withstand the elements. Step outside, and your world opens to a screened, heated pool surrounded by lush native landscaping that melts into the untouched preserve. When the day calls for adventure, your dock on a peaceful canal is ready for your boat, with quick access to some of the best fishing waters in florida. Whether you’re searching for a top-performing vacation rental or a personal hideaway that earns its keep when you’re away, this home is already a proven income generator — and it comes turnkey, so you can start living (or renting) the dream on day one. Opportunities for move-in waterfront properties don’t pop up on north captiva island very often — especially ones that offer this level of privacy, views, and modern construction. The only question is: will you let someone else watch your sunrise? Call today before this one disappears over the horizon.
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Subdivision Amenities

Underground Utility
Beach - Private
Beach Access
None

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(0.11 miles)
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$485K - $1.4M
(0.26 miles)
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$705K - $819K

Schools

Scores

Walk Score®
Car-Dependent. Almost all errands require a car
13

100
Bike Score®
Bikeable. Some bike infrastructure
52

100

Upper Captiva
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