Castaway Key Real Estate Sold

Mid-Tier
Mid-Tier
$400 - $650 per SqFt
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Results 4 of 4
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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Pending
Castaway Key, 4481 Bartlett Pkwy, Upper Captiva, Florida 33924, image 1
$988,000 $137K
  • 6 Beds
  • 31/2 Baths
  • 2,021 SqFt
  • $489/SqFt
Mid-Tier
House for sale in Castaway Key
4481 Bartlett Pkwy, Upper Captiva, FL 33924
Rare 6-bedroom north captiva island home with screened pool area where everyone has a place, and every moment feels like a vacation! Imagine arriving with a full house... Family, friends, kids, grandparents... All under one roof, yet everyone has their own space to unwind. Mornings begin with coffee around the kitchen's breakfast bar to plan the upcoming day at the beach. Afternoons drift between the pool, bbq area, game room, and shaded porch… and by evening, everyone gathers again, sharing stories over dinner as the island breeze moves through the lanai. This beautifully designed 6-bedroom, 3.5-bath plan was made for togetherness without crowding, offering expansive open living spaces to connect with family, along with private retreats for quiet moments. The heart of the home is a large open-concept living, dining, and kitchen area where meals turn into memories and laughter carries long into the night. Outside is a large covered key west-style front porch to perfect the island vibe. Just off the great room is a media room - perfect for movies and gaming any time of day. A spacious primary bedroom offers a sunny bay-window nook and an en-suite bath with a deep-soaking tub & shower combo. Three more guest rooms are just down the hall from the kitchen with a shared full bath. Downstairs, a relaxed den and games room create a natural draw for kids & teens for late-night hangouts, or a great hangout for older parents who don't like lots of stairs. Two bedrooms and a full bath, plus a laundry center on this level, make it a second essential recreation and living hub of the house, with the screened pool area just outside. This level seamlessly blends indoor comfort with outdoor fun. Step outside and the experience only gets better. A heated, screen-enclosed pool becomes the center of the day, surrounded by generous lounging and dining areas designed for long, unhurried afternoons. Just beyond, a separate poolside cabana with a wet bar and grilling station sets the stage for effortless entertaining—whether it's a casual lunch, sunset cocktails, or a full-on bbq cookout. The exterior of the house was upgraded with a new standing seam metal roof in 2023. Conveniently located just a short golf cart ride or walk from the ferry landing, island club amenities, and beach access.  Everything you need is within easy reach. Whether hosting multiple families, creating traditions for generations, or building a high-performing vacation rental designed for large groups, this is the kind of home where people come together and never want to leave. Take a closer look and start picturing your next gathering here.

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Subdivision Amenities

Underground Utility
Beach - Private
Beach Access
None

Nearby Subdivisions

(0.01 miles)
(0.11 miles)
For Sale (4)
$485K - $1.4M
(0.26 miles)
For Sale (2)
$705K - $819K

Schools

Scores

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

100
Bike Score®
Bikeable. Some bike infrastructure
52

100
Sound Score®
Bearable noise
83

100
Airport Score
Close to airports. Noticeable airport activity
0

100
Traffic Score
Congested area. Frequent traffic delays
21

100
Local Score
Limited local amenities nearby
0

100

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