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Castaway Key Real Estate Sold

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Entry-Level — Below $300 per SqFt
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Results 29 of 64
Castaway Key, 4540 Conch Shell Dr, Upper Captiva, Florida 33924, image 1
$1,595,000
  • 4 Beds
  • 4 Baths
  • 2,084 SqFt
  • $765/SqFt
Mid-Tier
House for sale in Castaway Key
4540 Conch Shell Dr, Upper Captiva, FL 33924
Just completed in 2019, this new custom-designed and crafted 4 bedroom, 4 bath home with a private pool on one of the quietest sandy lanes of the island. Built to later codes with hardie board siding, metal roof, impact-resistant doors/windows, hurricane strapping & composite decking. This gorgeous 2, 000+ sq ft home is finished luxuriously with a large peninsula kitchen that offers stainless steel appliances, off-white painted wood cabinetry, granite countertops, and a dining bar. The covered screen porch spans the entire width of the house. Upstairs, just off the largest bedroom with en suite bath, is a pergola-covered sun deck perfect for watching the sunset. Delightful meandering tropical gardens surround the house, plus a dining & outdoor entertainment area under the first floor with a built-in grill station and kids playground. Heated pool & spa, perfect for relaxing in the sun, close to the beach access points, and the state preserve entrance for miles of sandy gulf beaches and nature trails to explore. If you are looking for a newer home on the island with lower maintenance & insurance costs, and high-performance rental potential, this home is a must-see!
Castaway Key, 4450 Schooner Dr, Upper Captiva, Florida 33924, image 1
$190,000
  • 0.21 Acres
  • $904,762/Acre
Mid-Tier
Land for sale in Castaway Key
4450 Schooner Dr, Upper Captiva, FL 33924
A great lot located on north captiva island to build your perfect tropical retreat! A true barrier island with no bridges, only accessible by boat, ferry, or plane. Just a quick walk to miles of pristine beaches, ferry landing, restaurants and resort area. Included with purchase of the lot is the captiva castaway llc. Membership, which allows access to a deeded gulf front lot.
Castaway Key, 4440 Schooner Dr, Upper Captiva, Florida 33924, image 1
$150,000
  • 0.21 Acres
  • $714,286/Acre
Mid-Tier
Land for sale in Castaway Key
4440 Schooner Dr, Upper Captiva, FL 33924
Best value in an upper captiva homesite. The vegetation front and back provide excellent privacy. The existing mound for drain-field adds value and provides a jumpstart for building a fine home here. Walking distance to north captiva island club makes recreation and dining convenient.
Castaway Key, 4500 Smugglers Dr, Upper Captiva, Florida 33924, image 1
$150,000
  • 0.22 Acres
  • $681,818/Acre
Mid-Tier
Land for sale in Castaway Key
4500 Smugglers Dr, Upper Captiva, FL 33924
Excellent close to beach location in the castaway key neighborhood on north captiva. This lot is located within a close walk of beautiful wide sandy beaches and resort-style amenities & a ferry landing.
Castaway Key, 4460 Schooner Dr, Upper Captiva, Florida 33924, image 1
$151,000
  • 0.21 Acres
  • $719,048/Acre
Mid-Tier
Land for sale in Castaway Key
4460 Schooner Dr, Upper Captiva, FL 33924
North captiva island building lot within short walking distance of ferry landing, restaurants, club amenities. Some peeks of a bay view may be possible from a lookout level. Just a golf cart ride away from beach access points and acres of wildlife preserve/walking trails and uninhabited beaches.
Castaway Key, 516 Pirate Dr, Upper Captiva, Florida 33924, image 1
$885,000
  • 4 Beds
  • 3 Baths
  • 1,624 SqFt
  • $545/SqFt
Mid-Tier
House for sale in Castaway Key
516 Pirate Dr, Upper Captiva, FL 33924
Stunning 4 bed 3 bath home with a private pool on beautiful north captiva island. The floor plan is ideal for entertaining, maximizing views and access to the observation deck. Great room and open floorplan on upper level opens to the large screened lanai giving you extra entertaining space and the ability to truly enjoy the florida lifestyle year round. Kitchen is updated and features granite counters and stainless appliances. The entire main level features stylish vinyl plank flooring, a spacious master suite and 3 generous guest bedrooms and 2 full baths, all nicely appointed with coastal decor and flat screen tvs. The private heated pool is a secluded retreat with a large deck for sunning and entertaining and flows nicely to the covered outdoor entertaining space complete with ping pong, bean bag toss and bbq area. Rinse off from the beach in the huge custom outdoor shower with hot and cold water. The 4th floor observation deck is one of the highest on the island giving you panoramic gulf to bay views, ospreys, eagles and sunsets like no other. Your new island getaway is situated in the heart of north captiva- just steps to beach and restaurants.
Castaway Key, 4431 Conch Shell Dr, Upper Captiva, Florida 33924, image 1
$125,000
  • 0.32 Acres
  • $390,625/Acre
Mid-Tier
Land for sale in Castaway Key
4431 Conch Shell Dr, Upper Captiva, FL 33924
Oversized high and dry corner lot, just a quick hop to the preserve trails and widest beaches on the island. View corridor to the wildlife preserve. Already partially cleared, with many mature tropical trees still in tact. The perfect spot to build your dream beach house. This lot is priced to sell. Great value!
Castaway Key, 4500 Conch Shell Dr, Upper Captiva, Florida 33924, image 1
$175,000
  • 0.22 Acres
  • $795,455/Acre
Mid-Tier
Land for sale in Castaway Key
4500 Conch Shell Dr, Upper Captiva, FL 33924
Come and enjoy true island living in a brand new home. Buying this lot will give you a jump-start on the process. Survey , clearing, and septic permits in place. House plans and engineering are ready to submit for permitting.
Castaway Key, 4540 Cutlass Dr, Upper Captiva, Florida 33924, image 1
$184,000
  • 0.25 Acres
  • $736,000/Acre
Mid-Tier
Land for sale in Castaway Key
4540 Cutlass Dr, Upper Captiva, FL 33924
High & dry oversized island building lot with potential gulf views from the lookout level.
Castaway Key, 4581 Cutlass Dr, Upper Captiva, Florida 33924, image 1
$495,000
  • 0.5 Acres
  • $990,000/Acre
Mid-Tier
Land for sale in Castaway Key
4581 Cutlass Dr, Upper Captiva, FL 33924
Fantastic oversized lot with gulf & beach views just one row from the sugar sand beach of north captiva! High elevation land and large enough to build your dream estate-sized home. The top living floor and lookout of a well-designed home will encompass panoramic & expansive water views, and bring the sparkling colors of the sea to every corner of your sunset-facing rooms and porches. With this oversized lot of over 1/2 acre, you will have plenty of space for a large private pool, outdoor entertainment area, and landscaping with tropical gardens. Create an heirloom property near the beach. Access to the gulf beach is just a short walk or drive from the property along gulf lane.
Castaway Key, 4481 Cutlass Dr, Upper Captiva, Florida 33924, image 1
$125,000
  • 0.21 Acres
  • $595,238/Acre
Mid-Tier
Land for sale in Castaway Key
4481 Cutlass Dr, Upper Captiva, FL 33924
Excellent opportunity to own your own piece of paradise! This lot has higher land elevations and is located on a quiet sandy island lane, within a short distance of the beach.
Castaway Key, 4521 Bartlett Pkwy, Upper Captiva, Florida 33924, image 1
$162,000
  • 0.49 Acres
  • $330,612/Acre
Mid-Tier
Land for sale in Castaway Key
4521 Bartlett Pkwy, Upper Captiva, FL 33924
This double-sized corner lot on north captiva island offers plenty of space to build your island dream estate! Almost 1/2 acre of land. Conveniently located a short distance to the nearby beach access and the island club pool, bar & marina, ferry landing, dining, boat rentals, and shopping. If you are looking for an oversized lot in this price range, this is the one!
Castaway Key, 671 Rum Rd, Upper Captiva, Florida 33924, image 1
$529,000
  • 0.33 Acres
  • $1,603,030/Acre
Mid-Tier
Land for sale in Castaway Key
671 Rum Rd, Upper Captiva, FL 33924
Very rare opportunity to purchase a vacant land parcels on the southernmost north captiva island canal bordering the state preserve! A well-designed home's upper levels will offer unobstructed views across the state wildlife reserve to pine island sound, plus vistas over the entire preserve and island to the gulf for beautiful sunsets. It is located adjacent to a neighborhood hoa double-sized parcel at the end of the canal, which offers extra green space to the south. If you are looking for great views, private dockage for multiple boats, and privacy while close to the beach, this lot may be the one for you!
Castaway Key, 546, 552 & 558 Coral Cir, Upper Captiva, Florida 33924, image 1
$449,700
  • 0.68 Acres
  • $661,324/Acre
Mid-Tier
Land for sale in Castaway Key
546, 552 & 558 Coral Cir, Upper Captiva, FL 33924
Three-lot package deal on north captiva island! These parcels are so close to the beach! Just a short golf cart ride from club amenities, shopping, dining, and ferry landing. With potential views of the gulf from lookout levels, this bundle of properties gives you the opportunity to build a massive estate-sized home with extra privacy or up to three homes for a family compound.
Castaway Key, 4511 Schooner Dr, Upper Captiva, Florida 33924, image 1
$929,000
  • 3 Beds
  • 31/2 Baths
  • 1,608 SqFt
  • $578/SqFt
Mid-Tier
House for sale in Castaway Key
4511 Schooner Dr, Upper Captiva, FL 33924
Charming north captiva island getaway with a fully upgraded exterior! Thoughtfully crafted with a reverse floorplan that maximizes light, space, and beautiful tropical surroundings. The open-concept living area seamlessly extends to a spacious screened lanai, perfect for indoor-outdoor living. The galley-style kitchen features a large dining bar & walk-in pantry. Two primary suites with en suite baths offer private walk-in showers. A versatile den serves as the bunk room, providing a fourth sleeping area for guests. The fully upgraded exterior combines convenience with peace of mind. This home boasts impact-resistant doors & sliding glass doors, new pgt energy-efficient, argon-filled, low e glass impact-resistant windows, maintenance-free composite decking, aluminum railings, a new composite vinyl siding rated for 150-mph winds with a lifetime color warranty, and a top-of-the-line highly durable fiberglass/epoxy lanai deck. Other recent upgrades include a new roof with a transferable premium warranty, new energy-efficient hvac units with wi-fi programable thermostats, and new kitchen appliances. The adjacent vacant lot is also available for purchase - offering an opportunity for added privacy, expanded outdoor space, or even a future guest house. Plus, a share in a private beach lot is available for exclusive beach access. Convenient home location, just a short walk to the beach, ferry, and resort amenities. There is plenty of room to add a pool. Excellent rental potential. Priced well below reconstruction cost, this is an exceptional value for island living! Don't miss this chance to own an affordable island retreat - schedule your showing today!
Castaway Key, 621 Rum Rd, Upper Captiva, Florida 33924, image 1
$1,590,000$110K
  • 3 Beds
  • 31/2 Baths
  • 2,481 SqFt
  • $641/SqFt
Mid-Tier
House for sale in Castaway Key
621 Rum Rd, Upper Captiva, FL 33924
Upper captiva home. This gorgeous home, 3 bedroom + den & 4 baths, has everything you would want for an island home. Gulf access canal home with a large dock. Room for 2 boats on a navigable canal. A large pool when the kids want to swim "now." come see the wonderful views overlooking the wildlife preserve that go on for miles which gives the feeling of being far away from the rest of the busy world. The living area is on the upper floor to more enjoy the views of the state wildlife preserve. All hurricane impact glass windows. Cedar shiplap exterior siding. Wood burning fireplace. And the views are even better from the upper mezzanine area above the living room which could be another sleeping area. Plenty of room for guests with 3 bedrooms, a den and 3.5 bathrooms. Enjoy a beautiful kitchen. The decks wrap around the house for easy maintenance. Enjoy the large pool completely screened in. The beach is just down the road to a parking area with access to the widest beach on the island. New roof. Elevator! Could be an exceptional income producing property. Make an appointment to see this wonderful home.
Castaway Key, 4561 Smugglers Dr, Upper Captiva, Florida 33924, image 1
$624,900$75K
  • 2 Beds
  • 11/2 Baths
  • 891 SqFt
  • $701/SqFt
Mid-Tier
House for sale in Castaway Key
4561 Smugglers Dr, Upper Captiva, FL 33924
Adorable island cottage on beautiful north captiva island with classic beach style. This bungalow offers three sleeping rooms, making great use of the space. The living room and kitchen area are full of charm with tongue-and-groove wood walls, an authentic coastal retreat style. The two levels of decking are great for watching sunsets and gathering with the family. The home is located on a valuable oversized lot, just a short stroll or golf cart ride to the nearest beach access. Plenty of room to add on or install a large pool and outdoor entertainment area. Impact windows and sliders throughout, plus new hardie-board siding. Don't miss out on the chance to affordably obtain your beach house dream goal on this one-of-a-kind island!
Castaway Key, 4470 Conch Shell Dr, Upper Captiva, Florida 33924, image 1
$139,500
  • 0.22 Acres
  • $634,091/Acre
Mid-Tier
Land for sale in Castaway Key
4470 Conch Shell Dr, Upper Captiva, FL 33924
Beautiful island building in a high & dry area of north captiva. Enjoy resort-style amenities and the convenience of a location close to the ferry landing and yet a short golf cart or bike ride takes you to the nature preserve trails and breathtaking gulf beaches. The adjacent lot is also available, perfect for building one larger square footage home, two homes next to each other, or combining the two for a single residence with a large privacy buffer on every side of the property.
Castaway Key, 4490 Conch Shell Dr, Upper Captiva, Florida 33924, image 1
$139,900
  • 0.22 Acres
  • $635,909/Acre
Mid-Tier
Land for sale in Castaway Key
4490 Conch Shell Dr, Upper Captiva, FL 33924
High and dry lot on beautiful north captiva island! Surrounded by stunning natural beauty, this lot offers easy access to the beach, restaurants, and various island amenities, all within a short golf cart ride partially cleared. The perfect spot to build your new dream home!
Castaway Key, 4431 & 4441 Schooner &4430 Smugglers Dr, Upper Captiva, Florida 33924, image 1
$469,000
  • 0.88 Acres
  • $532,955/Acre
Mid-Tier
Land for sale in Castaway Key
4431 & 4441 Schooner &4430 Smugglers Dr, Upper Captiva, FL 33924
Three lot combo deal on north captiva island! Two oversized corner lots bordering rum rd, plus an adjacent lot on schooner dr.  Just steps from club amenities, shopping, dining, and the ferry landing. Bay and harbor views from the highest levels!  This bundle of properties allows you to build your family compound and/or have lots of space around your home.  Make an offer today!
Castaway Key, 4441 Schooner Dr, Upper Captiva, Florida 33924, image 1
$134,500
  • 0.22 Acres
  • $611,364/Acre
Mid-Tier
Land for sale in Castaway Key
4441 Schooner Dr, Upper Captiva, FL 33924
Priced to sell! Fantastic north captiva island lot located close to the island club resort amenities and pool/bar, shopping, and ferry landing. Just a quick golf cart ride to the nearby beach access point. Views of harbor may be possible from the lookout level. Don't miss this one!
Castaway Key, 4490 Schooner Dr, Upper Captiva, Florida 33924, image 1
$148,000
  • 0.21 Acres
  • $704,762/Acre
Mid-Tier
Land for sale in Castaway Key
4490 Schooner Dr, Upper Captiva, FL 33924
Tropical interior lot on the private and serene north captiva island, with miles of pristine beaches and vacation amenities. This location is conveniently located within a short golf cart ride or walk to the resort hub area with pools, dining, shopping, boat rentals, and the ferry landing. Just 1600 feet to the nearby state-owned beach access. It is time for you to start planning your new island beach retreat!
Castaway Key, 621 Rum Rd, Upper Captiva, Florida 33924, image 1
$1,950,000
  • 3 Beds
  • 31/2 Baths
  • 2,481 SqFt
  • $786/SqFt
Mid-Tier
House for sale in Castaway Key
621 Rum Rd, Upper Captiva, FL 33924
Rare canal home offered for sale on a protected canal with about 80 feet of dock possibly for larger boats. Its a beautiful home with a reverse floor plan with the living area on the upper floor. The views of the wildlife preserve are wonderful. And the views are even better from the upper mezzanine area above the living room which could be another sleeping area. Plenty of room for guests with 3 bedrooms, a den and 3.5 bathrooms. The third full bathroom is downstairs by the screened pool. The beach is just down the road to a public parking area with access to the widest beach on the island. New roof. Make an appointment to see this wonderful home.
Castaway Key, 4541 Conch Shell Dr, Upper Captiva, Florida 33924, image 1
$1,495,000
  • 3 Beds
  • 31/2 Baths
  • 1,646 SqFt
  • $908/SqFt
Mid-Tier
House for sale in Castaway Key
4541 Conch Shell Dr, Upper Captiva, FL 33924
An island masterpiece!  This elegant, custom-designed island estate blends traditional island-style charm with contemporary sophistication.  The home's exquisite detailing and bold roof lines create a unique and timeless design.  Sited on an oversized lot close to gulf beaches on a quiet sandy lane.  Hardie board siding, pella impact windows, and electric storm shutters provide peace of mind.  The private heated pool and screened outdoor entertainment area offer relaxation and island fun.  Perfectly designed for high-volume vacation rentals.  A grand two-story foyer welcomes you inside with an elegant winding wood staircase. Two spacious primary suites on the first level offer en suite baths with custom tile walk-in showers. The third guest bedroom enjoys its adjacent upgraded bath with a tub/shower. On the next level, the luxurious custom kitchen sparkles with granite countertops & stainless steel appliances. Deep dark wood cabinetry throughout the kitchen space offers elegantly curved corner cupboards for a sleek and functional appeal. Built-in yacht-style dining that seats 12+ in a three-side banquette uses the space ideally for entertaining. The living area meanders from the cozy tv/media area to covered screen porches and three levels of outdoor sundecks. Upstairs, the vaulted natural wood ceiling loft is a stunning focal point and versatile fourth sleeping space, offering gorgeous gulf views through expansive sliding glass doors.  Step up to the top lookout deck, where panoramic vistas of the gulf and the island's natural beauty unfold.  A rare blend of refined elegance and island serenity, this exceptional home is a magical seaside spot to enjoy your new island beach lifestyle.
Pending
Castaway Key, 4560 Conch Shell Dr, Upper Captiva, Florida 33924, image 1
$1,595,000$300K
  • 4 Beds
  • 31/2 Baths
  • 2,388 SqFt
  • $668/SqFt
Mid-Tier
House for sale in Castaway Key
4560 Conch Shell Dr, Upper Captiva, FL 33924
Elegant gulf view estate with pool on oversized lot! Located just one roof line from the gulf, this impressive north captiva island home is spacious & luxurious. Its 4 bedrooms & 3.5 baths provide plenty of room for family & friends. This island getaway is situated on an extra-large corner lot, offering enhanced privacy and excellent view corridors. The upper level offers the ultimate open-concept floor plan, anchored by a designer chef's kitchen featuring a large storage-and-prep island, a full dining bar, expansive custom cabinetry, quartz countertops, and stainless steel appliances. The great room is wrapped in bright, crisply painted shiplap, evoking the breezy elegance of a true island-style beach home. The large, covered connecting porch with gulf-facing views is perfect for watching sunsets and sipping margaritas. This thoughtfully designed home offers two private master suites, each with its own walk-in shower, double vanities, and spacious layout for peaceful retreats. On the first level, two additional bedrooms and a shared bath provide ample space for guests; one could be considered a mini-primary bedroom with access to a large covered porch facing the pool, and the other a spacious bunk room that sleeps 5+, perfect for large families or rental groups. Other highlights include a package lift/elevator for effortless luggage and grocery transport to the upper floors, unique wood-grain tile floors, beautifully appointed bathrooms, and charming coastal décor throughout. This home is exceptionally well-designed and ready to be tailored to your style and rental needs. Outside, the lower-level lounge, dining, entertaining, and sundeck areas cover most of the home's footprint, offering fantastic opportunities for shady spots and sunny perches. The private heated pool resides amongst mature tropical trees with plenty of room for all to lounge the day away in the sun! Updated in 2021 with new impact windows/doors & hardie board siding. The ferry landing, club pool, tennis courts, dining, and shops are all just a quick golf cart ride away. With its prime location, gulf views, high-end finishes, extra-large lot size, and character, this home offers a rare opportunity to own an estate home on the south side of the island near the sparkling gulf waters, where you can watch the stunning sunsets every night from your dream home!
Castaway Key, 4430 Smugglers Dr, Upper Captiva, Florida 33924, image 1
$85,000
  • 0.33 Acres
  • $257,576/Acre
Mid-Tier
Land for sale 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!
Castaway Key, 4561 Smugglers Dr, Upper Captiva, Florida 33924, image 1
$719,900
  • 2 Beds
  • 11/2 Baths
  • 891 SqFt
  • $808/SqFt
Mid-Tier
House for sale in Castaway Key
4561 Smugglers Dr, Upper Captiva, FL 33924
Adorable island cottage on beautiful north captiva island with classic beach style. This bungalow offers three sleeping rooms, making great use of the space. The living room and kitchen area are full of charm with tongue-and-groove wood walls, an authentic coastal retreat style. The two levels of decking are great for watching sunsets and gathering with the family.  The home is located on a valuable oversized lot, just a short stroll or golf cart ride to the nearest beach access. Plenty of room to add on or install a large pool and outdoor entertainment area. Impact windows and sliders throughout, plus new hardie-board siding. Don't miss out on the chance to affordably obtain your beach house dream goal on this one-of-a-kind island!
Castaway Key, 534 Longboat Cir, Upper Captiva, Florida 33924, image 1
$159,900
  • 0.33 Acres
  • $484,545/Acre
Mid-Tier
Land for sale in Castaway Key
534 Longboat Cir, Upper Captiva, FL 33924
Nestled in the heart of north captiva's vibrant resort area, this oversized island building lot offers harbor and bay views from the highest levels. Just a short stroll to the island club ferry landing, pool & dining/bar, island market, as well as all the recreational activities offered at boats & fun. Beach access points are a short walk or golf cart ride from the house, with miles of pristine shoreline for beachcombing, shelling, and sunsets.
Castaway Key, 4511 Schooner Dr, Upper Captiva, Florida 33924, image 1
$929,000
  • 3 Beds
  • 31/2 Baths
  • 1,608 SqFt
  • $578/SqFt
Mid-Tier
House for sale in Castaway Key
4511 Schooner Dr, Upper Captiva, FL 33924
Charming north captiva island getaway with a fully upgraded exterior! Thoughtfully crafted with a reverse floorplan that maximizes light, space, and beautiful tropical surroundings. The open-concept living area seamlessly extends to a spacious screened lanai, perfect for indoor-outdoor living. The galley-style kitchen features a large dining bar & walk-in pantry. Two primary suites with en suite baths offer private walk-in showers.  A versatile den serves as the bunk room, providing a fourth sleeping area for guests. The fully upgraded exterior combines convenience with peace of mind. This home boasts impact-resistant doors & sliding glass doors, new pgt energy-efficient, argon-filled, low e glass impact-resistant windows, maintenance-free composite decking, aluminum railings, a new composite vinyl siding rated for 150-mph winds with a lifetime color warranty, and a top-of-the-line highly durable fiberglass/epoxy lanai deck. Other recent upgrades include a new roof with a transferable 50-year warranty, new energy-efficient hvac units with wi-fi programable thermostats, and new kitchen appliances.   The adjacent vacant lot is also available for purchase - offering an opportunity for added privacy, expanded outdoor space, or even a future guest house. Plus, a share in a private beach lot is available for exclusive beach access. Convenient home location, just a short walk to the beach, ferry, and resort amenities. There is plenty of room to add a pool. Excellent rental potential. Priced well below reconstruction cost, this is an exceptional value for island living! Don't miss this chance to own an affordable island retreat - schedule your showing today!
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