Mid-Tier Real Estate For Sale in 33924 Zip Code

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Safety Harbor Club, 370 Townhouse Ln #60, Upper Captiva, Florida 33924, image 1
Safety Harbor Club, 370 Townhouse Ln #60, Upper Captiva, Florida 33924, image 2
$475,000 $4K
  • 3 Beds
  • 2 Baths
  • 954 SqFt
  • $498/SqFt
Mid-Tier
Townhouse for sale in Safety Harbor Club
370 Townhouse Ln #60, Upper Captiva, FL 33924
End unit with harbor views & dock access! Experience the tropical island waterfront lifestyle! This value-priced townhome offers shared dockage for your boat, and an unbeatable location just steps from the dockage, ferry landing, and club restaurant… because sometimes the outside is doing all the heavy lifting. Let’s be clear: the interior is authentically, unapologetically vintage. We’re talking original finishes, original fixtures, and décor. The kitchen and baths? Classic. The vibe? Beach retro. The opportunity? Endless. But here’s the thing—this townhome is livable, functional, and ready for its next chapter. Whether you’re dreaming of a full renovation, a creative reimagining, or simply embracing the throwback charm (we won’t judge), this is your chance to start with a light-and-airy plan in an even better location. And what a location it is—end unit, harbor views, steps to dockage and kayak beach... And just a short distance to everything safety harbor club has to offer. Enjoy access to a heated pool, tennis and pickleball courts, clubhouse dining, and private gulf beach access where the sunsets are always in style (no renovation required). Bring your vision. Bring your contractor. Or bring your love for 1985. Either way, this is your chance to secure a waterfront foothold in an end unit at a price that leaves room for transformation. Don’t miss this unique before-and-after opportunity.
Safety Harbor Club, 370 Townhouse Ln #66, Upper Captiva, Florida 33924, image 1
Safety Harbor Club, 370 Townhouse Ln #66, Upper Captiva, Florida 33924, image 2
$490,000 $39K
  • 3 Beds
  • 2 Baths
  • 953 SqFt
  • $514/SqFt
Mid-Tier
Townhouse for sale in Safety Harbor Club
370 Townhouse Ln #66, Upper Captiva, FL 33924
Priced to sell! Positioned directly on the harbor in safety harbor club, this waterfront townhome offers one of the most convenient dockside locations on north captiva island. With the boat docks less than 50 feet from your door, this home is ideal for those who want immediate access to boating and waterfront living. The layout is designed to capture excellent harbor views while providing comfortable island living. Light-filled interior spaces flow naturally to the outdoor covered screen porch, where you can watch boats come and go and enjoy the serene waterfront setting. As part of safety harbor club, owners enjoy a full suite of amenities including a community pool, tennis & pickleball courts, clubhouse, on-site dining, & gulf beach access. The nearby ferry landing makes travel simple while maintaining the peaceful, car-free charm of north captiva. Whether used as a personal retreat or investment property, this harborfront townhome offers an exceptional combination of location, lifestyle, and boating convenience on one of florida’s most unique barrier islands. There is a tenant currently in place until july 31, 2026.
Safety Harbor Club, 370 Townhouse Lane 61, Upper Captiva, Florida 33924, image 1
Safety Harbor Club, 370 Townhouse Lane 61, Upper Captiva, Florida 33924, image 2
Safety Harbor Club, 370 Townhouse Lane 61, Upper Captiva, Florida 33924, image 3
$510,000 $40K
  • 3 Beds
  • 2 Baths
  • 989 SqFt
  • $516/SqFt
Mid-Tier
Townhouse for sale in Safety Harbor Club
370 Townhouse Lane 61, Upper Captiva, FL 33924
Steps from the water! You can hear the bay waters gently sloshing against the shoreline from the front deck. Enjoy beautiful bay views from the front screened-in deck and watch the boats come and go from safety harbor. Relax to the sounds of the cheerful sea birds that soar over safety harbor and watch the dolphins swim in the bay. This meticulously maintained townhouse has gorgeous views of safety harbor. New roof in 2023. The master suite has an updated bathroom with walk-in shower, and there is a peaceful screened-in sitting area right off the master bedroom. Two adorable bedrooms are upstairs, with sweeping bay views from one of the upstairs bedrooms. The lower area has brand new flooring, a laundry area, and full golf cart garage to park your golf cart (included). The community dockage is just steps away from the front door, with additional slips available at the community wharf where you will find a fish cleaning station and plenty of docks to fish from. Also steps away from the front door is a lovely bay beach where you can launch your kayak (included) or go fishing. Membership with safety harbor club includes a community heated pool, tennis and pickle ball, private beach access, a restaurant on the water, clubhouse, and miles of pristine, uncrowded, white sugar-sand gulf beaches. North captiva is an island with no roads to it, so ride the bi-hourly island girl ferry from pineland marina to north captiva and get around the island on golf carts. This unique feature of the island makes it particularly peaceful and attractive.
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Castaway Key, 621 Rum Rd, Upper Captiva, Florida 33924, image 1
Castaway Key, 621 Rum Rd, Upper Captiva, Florida 33924, image 2
Castaway Key, 621 Rum Rd, Upper Captiva, Florida 33924, image 3
$1,299,000 $100K
  • 3 Beds
  • 31/2 Baths
  • 2,481 SqFt
  • $524/SqFt
Mid-Tier
House for sale in Castaway Key
621 Rum Rd, Upper Captiva, FL 33924
Upper captiva canal home. Room for two boats. Needs some updating. Beautiful private views across the state park to pine island from this gorgeous 3 bedroom plus a den & 3.5 bathroom home. It has everything you would want from an island home including protected docking for your boats on a navigable canal which leads out to the gulf of mexico and the intracoastal waterway, an elevator to bring groceries and supplies up to the kitchen, all windows are hurricane impact windows, cedar ship-lap exterior siding, wood burning fireplace, an upper mezzanine area above the living room which could be a studio or office, plenty of room for guests, a beautiful kitchen with big windows showing the view to the state park, wide decks wrap around the house on both floors, a large screened-in pool with a shower and bathroom, new electric system inside and out, new roof, newly painted decks, newly painted exterior. Also, recent maintenance check on the elevator. The beach is just down the sandy path to a parking area with access to the widest beach on the island. This island home could be an exceptional income producing property. Please make an appointment to see this wonderful home soon.
Safety Harbor Club, 4491 Escondidio Ln #73, Upper Captiva, Florida 33924, image 1
Safety Harbor Club, 4491 Escondidio Ln #73, Upper Captiva, Florida 33924, image 2
Safety Harbor Club, 4491 Escondidio Ln #73, Upper Captiva, Florida 33924, image 3
$599,000
  • 3 Beds
  • 2 Baths
  • 1,064 SqFt
  • $563/SqFt
Mid-Tier
Townhouse for sale in Safety Harbor Club
4491 Escondidio Ln #73, Upper Captiva, FL 33924
Experience the best of coastal living in one of the premier townhomes in safety harbor club! This beautifully updated end-unit offers 3 bedrooms, 2 full baths, and is filled with natural light thanks to additional impact windows, creating a bright and airy interior throughout. Exceptional outdoor living awaits with two screened lanais plus a third balcony. Thoughtfully renovated, recent improvements include impact-resistant windows, a newer roof, newer hvac system, and an on-demand tankless water heater, providing years of worry-free ownership. The finished lower level offers versatile space for a home office, fitness area, laundry room or guest accommodations, along with garage storage and a golf cart for added convenience. Offered fully furnished and turnkey, this move-in-ready residence is an outstanding full-time home, seasonal retreat, or income-producing investment with excellent rental history and opportunity for seller financing. Safety harbor club residents enjoy resort-style amenities including a heated community pool, tennis and pickleball courts, clubhouse, convenient beach access, and dockage for boating enthusiasts. Enjoy the perfect combination of updated coastal elegance, abundant indoor-outdoor living, and an unbeatable waterfront lifestyle.
Bayside Villas, 5323 Bayside Villas #24, Captiva, Florida 33924, image 1
Bayside Villas, 5323 Bayside Villas #24, Captiva, Florida 33924, image 2
Bayside Villas, 5323 Bayside Villas #24, Captiva, Florida 33924, image 3
$875,000 $50K
  • 3 Beds
  • 3 Baths
  • 1,496 SqFt
  • $585/SqFt
Mid-Tier
Condo for sale in Bayside Villas
5323 Bayside Villas #24, Captiva, FL 33924
Highly sought-after, updated 3 bed, 3 bath two-story villa stands apart with rare features not found in other bayside units, overlooking the tranquil waters of pine island sound, where unchanging estuary views and native wildlife create a peaceful, elevated backdrop—just moments from the best of captiva island. Rare features of this top-floor unit include a walk-in pantry—an uncommon luxury in bayside 3-bedroom villas—all-new hurricane-impact windows and sliders, and a residence that has been gently used as a private second home and never enrolled in a rental program—an added advantage in condition and care. Whether enjoyed as a private island retreat or leveraged as a high-performing investment, this residence offers rare flexibility within a renter-friendly community and stands as one of the least expensive 3-bedroom opportunities on captiva. The interior is anchored by an updated kitchen with quartz countertops, glass-front upper cabinetry, and matching appliances, flowing seamlessly into the main living area. Three generously sized bedrooms and three full baths include two primary suites—one on the main level and one upstairs—each with its own ensuite, offering ideal separation for guests or extended stays. A third guest bedroom also enjoys a private bath, while an in-unit washer and dryer adds everyday convenience. The screened lanai feels like your own private perch above pine island sound, where it’s just you, the water, and the rhythm of nature. From both the kitchen and lanai, morning sunrises unfold over the sound, setting the tone for slow mornings, passing wildlife, and uninterrupted calm. Set within south seas island resort in the desirable bayside villas enclave, just a stone’s throw from the sugar-white gulf beaches, the village of captiva, and captiva landing. Residents and guests enjoy a bayside pool and spa with generous lounging areas, along with under-building parking for added ease. Where time slows, views remain untouched, and every return feels like coming home—this is captiva at its finest.
Safety Harbor Club, 4481 Escondidio Ln #80, Upper Captiva, Florida 33924, image 1
Safety Harbor Club, 4481 Escondidio Ln #80, Upper Captiva, Florida 33924, image 2
Safety Harbor Club, 4481 Escondidio Ln #80, Upper Captiva, Florida 33924, image 3
$565,000
  • 3 Beds
  • 2 Baths
  • 954 SqFt
  • $592/SqFt
Mid-Tier
Townhouse for sale in Safety Harbor Club
4481 Escondidio Ln #80, Upper Captiva, FL 33924
Wake up in paradise at sunrise bay on north captiva island! Picture this: the first light of dawn glistens across pine island sound as you sip coffee on your screened porch, watching the world wake up in perfect peace. A gentle sea breeze slips through palm fronds, and within minutes, you can be out the door and onto your docked boat, sandy gulf shoreline, or quiet nature trail. Sunrise bay isn't just a townhome - it's your front-row seat to island life. This 3-bedroom, 2-bath townhome has been stylishly updated to deliver modern coastal comfort with a dose of old florida charm. Inside, sunlit living spaces, tasteful furnishings, and thoughtful upgrades create a warm, effortless retreat. The townhouse is entirely turnkey, with thoughtfully updated décor and furnishings so you can settle in and start enjoying your new island retreat immediately. Outside, you're just a short hop to the ferry landing, dock slips, over the waterfront dining, and endless opportunities to fish, shell, kayak, or relax in total tranquility. For boaters, this property is a dream come true, with community docks that provide easy access to the gulf for fishing trips, sunset cruises, or island-hopping adventures. If you prefer to keep your toes in the sand, pristine gulf-side beaches are just a short golf cart ride away, making spontaneous beach visits part of your everyday life. Safety harbor club's included resort-style amenities, including the recently updated sparkling heated community pool, tennis & pickleball courts, a clubhouse, and waterfront dining, give you the best of vacation living right at home. Perfect for a personal island hideaway or an income-generating rental, sunrise bay blends laid-back luxury with unbeatable convenience. Properties with this level of charm, boat dockage, & water views don't usually last long at this price. Schedule a showing today and claim your place in paradise!
Bayside Villas, 5321 Bayside, Captiva, Florida 33924, image 1
Bayside Villas, 5321 Bayside, Captiva, Florida 33924, image 2
Bayside Villas, 5321 Bayside, Captiva, Florida 33924, image 3
$950,000
  • 3 Beds
  • 3 Baths
  • 1,496 SqFt
  • $635/SqFt
Mid-Tier
Townhouse for sale in Bayside Villas
5321 Bayside, Captiva, FL 33924
Sw fl has it all-- sunshine, culture, and endless recreation! From the red sox & twins stadiums, beaches, boating, tours, and convenient access to an international airport, this is a perfect getaway destination. While you're enjoying everything sw fl has to offer, don't miss the chance to own a top floor, 3-bed/3-bath townhouse retreat in bayside villas, located within the gated south seas island resort on captiva island. The private lanai showcases breathtaking, direct views of sunrise over the bay, pine island sound & beyond. Low green mangroves provide natural erosion protection and serve as a thriving habitat for local wildlife--beautiful, serene, and uniquely florida. Watch boats glide in and out of the canal leading to the marina, adding a touch of coastal charm to your daily view. Take a short walk to the beach, feel the sand between your toes, and enjoy unforgettable sunsets. You're also just steps from the post office, bank, atm, captiva shops, and restaurants.
Bayside Villas, 5132 Bayside Villas, Captiva, Florida 33924, image 1
Bayside Villas, 5132 Bayside Villas, Captiva, Florida 33924, image 2
Bayside Villas, 5132 Bayside Villas, Captiva, Florida 33924, image 3
$445,000 $30K
  • 1 Beds
  • 2 Baths
  • 684 SqFt
  • $651/SqFt
Mid-Tier
Condo for sale in Bayside Villas
5132 Bayside Villas, Captiva, FL 33924
At 5132 bayside villas, each day is written in light, water, and breeze. Dawn begins on the lanai, where pine island sound awakens with color—sunrise glows across the horizon, pelicans skim the waves, and fishing boats slip toward open water. The bay becomes your backdrop, alive with sails, seabirds, and the shifting palette of the sky. The villa itself balances coastal charm with modern ease. A 1bd/2ba first-floor retreat, it offers granite counters, stainless appliances, crisp cabinetry, wide-plank tile flooring, and crown molding. The living spaces flow naturally to the lanai, where the outdoors remains the centerpiece. The primary suite offers a calm retreat, while a second bath mirrors the same fresh finishes. Yet what makes this villa extraordinary is not just the design—it’s the rhythm of captiva life outside its doors. Within minutes, you can sink your feet into the gulf sands, celebrated for their shells and sunlit shallows. Island pathways invite golf cart rides and bike cruises into captiva village, where the hum of music, dining, and laughter sets a different tempo. Afternoons bring choices: a swim in the bayside pool, a paddle through calm waters where dolphins are frequent companions, or a wander through palm-lined trails. As the day winds down, the stage shifts once more. Perhaps you’ll gather with neighbors for cocktails while the boats return across the channel or cross the island to witness sunset blaze into the gulf. And when evening deepens, stars scatter above the mangroves, promising another sunrise to come. With amenities like under-building parking, private storage, and a bayside pool and spa, 5132 bayside villas offers not just a home but an island way of life—measured in sunrises, sails, and timeless captiva moments.
Tennis Villas, 3233 Tennis Villas, Captiva, Florida 33924, image 1
Tennis Villas, 3233 Tennis Villas, Captiva, Florida 33924, image 2
Tennis Villas, 3233 Tennis Villas, Captiva, Florida 33924, image 3
$595,000
  • 2 Beds
  • 2 Baths
  • 894 SqFt
  • $666/SqFt
Mid-Tier
Condo for sale in Tennis Villas
3233 Tennis Villas, Captiva, FL 33924
Tucked within the gated setting of south seas resort, 3233 tennis villas presents an inviting island escape in the intimate captiva resort villascommunity. Residents enjoy access to a private pool, expansive sun deck, gazebo with outdoor dining space, and grilling area, all just moments from the gulfshoreline. Positioned in the desirable southern enclave and only a short stroll to the beach, this top-floor, two-level villa overlooks a tranquil courtyard framed bymature tropical landscaping. The interior has been thoughtfully updated with quartzite surfaces, crisp shaker-style cabinetry, and tile flooring throughout the mainliving areas. The open living and dining space is filled with natural light from impact-rated sliding glass doors and an oversized picture window, while the screenedlanai offers a peaceful setting to capture coastal breezes. The floor plan is designed for comfort and privacy, featuring a guest suite on the main level and agenerous primary suite upstairs. Ideal for personal enjoyment or investment, this well-appointed residence blends refined finishes with effortless island living withinone of captiva’s most sought-after resort communities.
Tennis Villas, 3132 Tennis Villas, Captiva, Florida 33924, image 1
Tennis Villas, 3132 Tennis Villas, Captiva, Florida 33924, image 2
Tennis Villas, 3132 Tennis Villas, Captiva, Florida 33924, image 3
$624,000 $15K
  • 2 Beds
  • 2 Baths
  • 906 SqFt
  • $689/SqFt
Mid-Tier
Condo for sale in Tennis Villas
3132 Tennis Villas, Captiva, FL 33924
Imagine slipping away to captiva and discovering the villa that redefines your idea of an island escape. Welcome to captiva resort villas 3132—freshly renamed for 2025 and tucked behind the gates of south seas resort. This two-bedroom, two-bath, dual-level villa blends comfort with coastal charm in all the right ways. Step inside to bright, airy living with granite counters, impact sliders, ceilings tall enough to make your shoulders drop, and an extended lanai that adds extra room to lounge, dine, or simply daydream. Upstairs, a loft-style primary suite feels like an adults-only treehouse—private, calm, and made for slow mornings. The main level offers a sun-filled living area, guest bedroom, and full bath, all opening to peaceful courtyard views with prized northern exposure. Life here comes with easy perks: a sparkling pool, bbq gathering spots, and elevators for convenience. Stroll to the village of captiva for boutiques, a morning starbucks, or iconic island dining. Wander the other direction and you’re on the beach in minutes—perfect for those legendary captiva sunsets.
Castaway Key, 4561 Smugglers Dr, Upper Captiva, Florida 33924, image 1
Castaway Key, 4561 Smugglers Dr, Upper Captiva, Florida 33924, image 2
$634,900 $15K
  • 2 Beds
  • 11/2 Baths
  • 891 SqFt
  • $713/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!
Bayside Villas, 4216 Bayside Villas, Captiva, Florida 33924, image 1
Bayside Villas, 4216 Bayside Villas, Captiva, Florida 33924, image 2
Bayside Villas, 4216 Bayside Villas, Captiva, Florida 33924, image 3
$489,000 $41K
  • 1 Beds
  • 2 Baths
  • 684 SqFt
  • $715/SqFt
Mid-Tier
Condo for sale in Bayside Villas
4216 Bayside Villas, Captiva, FL 33924
This beautifully appointed one-bedroom, two-bathroom villa at bayside villas is not only a stunning coastal retreat but also a fantastic investment property with daily rental capabilities. Offering breathtaking views of the marina and bay, leading to open waters, this villa features luxurious wood-like tile flooring, granite countertops, and coastal-inspired decor throughout. Nestled in the heart of the bayside villas community, residents enjoy convenient access to captiva's pristine beaches, vibrant village, and unforgettable sunsets. Community amenities include a pool, spa, under-building parking, and an assigned storage locker. Whether for personal enjoyment or investment purposes, this property is sure to delight. Your slice of paradise awaits!
Bayside Villas, 5232 Bayside Villas, Captiva, Florida 33924, image 1
Bayside Villas, 5232 Bayside Villas, Captiva, Florida 33924, image 2
Bayside Villas, 5232 Bayside Villas, Captiva, Florida 33924, image 3
$494,900 $50K
  • 1 Beds
  • 2 Baths
  • 684 SqFt
  • $724/SqFt
Mid-Tier
Condo for sale in Bayside Villas
5232 Bayside Villas, Captiva, FL 33924
Start each day surrounded by the sights and sounds of island life from this second-floor, one-bedroom, two-bath furnished condo overlooking pine island sound. Sunlight pours through wide sliders that open to a private lanai, where gentle breezes carry the scent of salt air and the call of seabirds. Watch dolphins play and boats drift by—a constant reminder you’re living on island time. Located within the southern enclave of south seas resort blends comfort and convenience with an easygoing captiva lifestyle. Tile flooring throughout creates a cool, carefree atmosphere, while the kitchen features stainless-steel appliances and open sightlines to the bay. The guest bath provides added flexibility for visitors, and the bedroom offers a peaceful retreat after a day in the sun. Owners participating in the resort rental program and club captiva enjoy access to full resort amenities, including sunset beach, pools, lounges, umbrellas, and chairs for relaxed days along the gulf—all just a short stroll away. A ground-level storage locker in the 5000 building is perfect for keeping beach gear, sup, or fishing gear! From this ideal location, it’s easy to enjoy all that captiva has to offer—bike along palm-lined roads, kayaking through mangroves, or watching the sunset over the gulf. Explore the island by golf cart, or unwind with cocktails as the sun dips below the horizon. The bayside villas community also features a waterfront pool, spa, and under-building parking. 5232 bayside villas offers a front-row seat to captiva’s natural beauty and a laid-back rhythm that makes every day feel like vacation.
Safety Harbor Club, 4490 Harbor Bend Dr, Upper Captiva, Florida 33924, image 1
Safety Harbor Club, 4490 Harbor Bend Dr, Upper Captiva, Florida 33924, image 2
$1,397,000 $53K
  • 3 Beds
  • 2 Baths
  • 1,841 SqFt
  • $759/SqFt
Mid-Tier
House for sale in Safety Harbor Club
4490 Harbor Bend Dr, Upper Captiva, FL 33924
The perfect boater's retreat! This charming three-bedroom waterfront home on the harbor is fully remodeled. Excellent water views from both levels. Dock permits are in place to build a dock for your dream boat. Enjoy the custom-crafted kitchen with marble countertops and stainless steel appliances, with fantastic views across the living area to the harbor. Watch the wildlife and passing boats while relaxing on the deck or screened porch. Two large guest bedrooms share a fully upgraded hall bath with a custom tile walk-in shower. The east-facing bedroom enjoys views of the harbor and another screen porch access sliding glass door, perfect for catching the fresh seaside breezes. To the west is another guest bunk room. On the second level, the spacious primary suite with dual closets & a deluxe tiled bathroom offers a huge waterfront sun porch with composite decking. Just off the primary suite is a versatile sitting room that makes a great office, media room, or extra sleeping space. Impact windows & doors, as well as a newer aluminum standing seam roof, ensure durability and peace of mind. It is just steps from community dock slips with full membership to the safety harbor club amenities, pool, tennis, pickleball, and gulf beach access. This rare waterfront gem won't last. Schedule your private showing today!
Safety Harbor Club, 484 Gulf Bend Dr, Upper Captiva, Florida 33924, image 1
Safety Harbor Club, 484 Gulf Bend Dr, Upper Captiva, Florida 33924, image 2
Safety Harbor Club, 484 Gulf Bend Dr, Upper Captiva, Florida 33924, image 3
$1,850,000
  • 3 Beds
  • 3 Baths
  • 2,435 SqFt
  • $760/SqFt
Mid-Tier
House for sale in Safety Harbor Club
484 Gulf Bend Dr, Upper Captiva, FL 33924
Great opportunity! This is your chance for a large prime gulf front beach home! This amazing home is right on the beach with private beach access just steps out the door. Simply spectacular oceans views from the entire beach side of this property! This large beach home is located in the fantastic safety harbor club offering the availability of shared boat dockage for it’s members – a commodity that boaters will love! Safety harbor also features a community pool, clubhouse, tennis/pickleball courts etc. Located on an oversized lot on the wide sugar sand of butterfly beach - this 2400 sq ft+ beach house with a great room floor plan offers three bedrooms, three full baths, over 2400 plus square interior footage, plus a loft and interior storage room. With its' bright huge main living area with soaring ceilings, beautiful recess lighting, coffered ceilings, large kitchen and breath-taking oceans views you can envision the full potential of this beach front beauty right upon your entry! Two brs have ensuite full baths. There is also a fantastic screened balcony with access off of the primary br and living room, a large open balcony off of the loft offering superb gulf views and unforgettable sunsets and a nice side deck! Great under house area offers plenty of enclosed storage and covered carport areas. All new recent upgrades include: new roof and gutters. Three new ac units. New water heater. New hurricane shutters with hand cranks and motors. New hurricane door(s) loft, both sets of sliders in the living room, sliders in the primary bedroom and refrigerator. Windows are all hurricane impact rated per seller. New hunter fans in the main living area - sitting area, dining and kitchen plus new fans in the loft, guest and primary br. New lighting primary br. The home’s interior is freshly painted and there is new exterior paint. Two baths are remodeled with all new showers, vanities, faucets, mirrors etc. New kitchen faucet, fan, microwave. New dehumidifiers with custom drains to exterior. Etc. Schedule your showing today to see all that this beach home has to offer! It is a must see!
Bayside Villas, 5122 Bayside Villas, Captiva, Florida 33924, image 1
Bayside Villas, 5122 Bayside Villas, Captiva, Florida 33924, image 2
Bayside Villas, 5122 Bayside Villas, Captiva, Florida 33924, image 3
$549,000
  • 1 Beds
  • 2 Baths
  • 684 SqFt
  • $803/SqFt
Mid-Tier
Condo for sale in Bayside Villas
5122 Bayside Villas, Captiva, FL 33924
Just renovated bayside villa located in the gated private south seas resort. New kitchen and bathrooms to include granite countertops, shaker cabinets, new flooring, gorgeous walk-in shower all set in a soothing sea salt palette. Wake up to sunrise over pine island sound. The bayside amenities include an oversized sun-drenched pool and spa, under building parking, on site laundry, pool baths, marina side grills and picnic areas. No rental commitments so all options open. Move in and enjoy or place your property in a rental program. Just footsteps to the beach for a dip in the gulf of mexico. Easy access to village of captiva's shops, restaurants, boating and water sports. Enjoy south seas world class amenities with membership. Immerse yourself in the luxury of this stunning property. This exclusive opportunity enhances your living experience, offering a range of premium amenities and services tailored for members and guests. With this exceptional membership, enjoy unparalleled access to facilities that elevate your lifestyle.
Safety Harbor Club, 406 Gulf Bend Dr, Upper Captiva, Florida 33924, image 1
Safety Harbor Club, 406 Gulf Bend Dr, Upper Captiva, Florida 33924, image 2
$1,970,000 $30K
  • 3 Beds
  • 3 Baths
  • 2,454 SqFt
  • $803/SqFt
Mid-Tier
House for sale in Safety Harbor Club
406 Gulf Bend Dr, Upper Captiva, FL 33924
Rare opportunity to purchase luxurious gulf front estate on north captiva island a rare opportunity has arisen to purchase a luxurious gulf front estate located within the prestigious community of safety harbor club on north captiva island. This stunning coastal property boasts beach frontage with breathtaking sunsets and panoramic views of the gulf. Recently renovated and remodeled with the highest quality craftsmanship and attention to detail, this estate is truly one-of-a-kind. The interior of the property features a striking custom staircase, quartz countertops, and custom solid wood cabinetry in the kitchen. Beautiful oak and porcelain floors run throughout the home, creating a sense of elegance and luxury. The estate includes two guest bedrooms. One ensuite. The highlight of the property is the exquisite master bedroom, located on the second floor with private decks offering stunning views of the gulf. The master bedroom also features a fireplace and a large bathroom with a jet tub and separate shower. The spacious kitchen is equipped with an island cooktop, downdraft ventilation, subzero refrigerator/freezer, microwave with convection, wall oven, and dishwasher. The property offers gorgeous views of the beach from the master bedroom, kitchen, dining area, and great room. This custom home is truly a gem and must be seen to be fully appreciated. Schedule an appointment today to view this beautiful estate and make it your own.
Jose's Hideaway, 4500 Seair Ln, Upper Captiva, Florida 33924, image 1
Jose's Hideaway, 4500 Seair Ln, Upper Captiva, Florida 33924, image 2
$1,499,000 $96K
  • 3 Beds
  • 3 Baths
  • 1,808 SqFt
  • $829/SqFt
Mid-Tier
House for sale in Jose's Hideaway
4500 Seair Ln, Upper Captiva, FL 33924
One of the newest homes recently built on north captiva! Just completed in 2022, this home still feels pristine and like brand new! Built to the latest wind codes and with upgraded interior fixtures, decor, and finish. This 3 bedroom and 3 bath home is located directly on north captiva's private airstrip, offering excellent access for pilots as well as scenic views of the gulf and bay. The reverse floorplan of this home even offers views from the lower bedroom level as you gaze across the green space of the airstrip to the beaches at either end. The master suite offers a full en suite bath with a walk-in shower, private commode room, double sinks, and a large dressing room/closet. A large laundry space is conveniently located between the bedrooms. Two more exquisitely decorated guest bedrooms share a hallway bath with a deep soaking tub/shower combo. The upper level will impress with its large open-concept kitchen, dining, and living space open to the large covered and screened outdoor porch. The kitchen's central island will become the heart of your home, with dining spots on each side of the island. This kitchen offers a full pantry, quartz countertops, stainless steel appliances, large amounts of storage space, seating, and more. You have views of the bay right from a cozy coffee corner table, while the sparkling waters of the gulf are just outside your sliding glass doors. Enjoy the sunsets from your top-level lookout tower just off the living area. The private elevator rises from your ground-level entrance space and storage garage to the first and second levels of the home for your convenience and comfort. If you have been looking for a newer, move-in home on north captiva, this is the one! Don't miss it!
Castaway Key, 4541 Conch Shell Dr, Upper Captiva, Florida 33924, image 1
Castaway Key, 4541 Conch Shell Dr, Upper Captiva, Florida 33924, image 2
Castaway Key, 4541 Conch Shell Dr, Upper Captiva, Florida 33924, image 3
$1,395,000 $100K
  • 3 Beds
  • 31/2 Baths
  • 1,646 SqFt
  • $848/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.
Castaway Key, 660 Gulf Ln, Upper Captiva, Florida 33924, image 1
Castaway Key, 660 Gulf Ln, Upper Captiva, Florida 33924, image 2
Castaway Key, 660 Gulf Ln, Upper Captiva, Florida 33924, image 3
$3,895,000 $100K
  • 4 Beds
  • 41/2 Baths
  • 3,340 SqFt
  • $1,166/SqFt
Mid-Tier
House for sale in Castaway Key
660 Gulf Ln, Upper Captiva, FL 33924
Beauty & the beach is one of the most extraordinary gulf-front estate homes ever offered for sale on north captiva island! This custom-crafted contemporary residence sits on the central portion of the island's widest stretch of beach, providing greater long-term shoreline security and uninterrupted panoramic gulf views. A proven luxury vacation rental leader, this home generated over $360k in gross rentals in 2021.  The property booked over $250k in gross rentals in 2025, even with downtime for repairs and upgrades.  This is a rare opportunity to acquire both a premier vacation retreat and a top-tier rental asset. Designed with a striking stucco exterior, impact-resistant glass throughout, and a private interior elevator serving all three levels, the home delivers refined coastal architecture paired with modern convenience. The ground-level area provides a bonus room & bunk area, plus an extensive outdoor entertainment space with a pool, patio, outdoor kitchen & poolside bar, all connected by a private walkway to the island's most pristine sugar-sand beach. Inside, every space is meticulously planned & designed for elevated entertaining & relaxed luxury. Highlights include a gourmet chef's kitchen, a dramatic dining room crowned by soaring barrel-vaulted ceilings, and a formal living area wrapped in panoramic glass. A built-in fireplace with television above the hearth anchors the living space with warmth and elegance.  The two primary living levels were designed to capture the spectacular gulf and sunset views.   The 4 elegant bedroom suites provide marvelous spaces for you and your guests to experience five-star resort-style luxury sleeping accommodations. The top-level primary suite boasts panoramic beach views, an en suite bath with a walk-in shower, a dual-sink vanity, and a lockable owners' closet.  Imagine relaxing in the extra-deep soaking tub while you stare at the shimmering waters lapping the shoreline. The second primary suite, located just off the entertainment den/media room, offers excellent beach views & a luxury en suite bath with a walk-in shower. Two more north-facing guest suites create "family-suite-style" guest zones with a gulf-facing king bed suite & en suite bath, plus an adjacent bedroom & bath.  Opportunities to acquire a gulf-front estate of this caliber, location, and proven income performance are exceedingly rare on north captiva island. Beauty & the beach represents the very best of luxury island living!
Gold Coast Of Captiva Island, 16512 Captiva Dr, Captiva, Florida 33924, image 1
Gold Coast Of Captiva Island, 16512 Captiva Dr, Captiva, Florida 33924, image 2
$7,950,000 $2M
  • 6 Beds
  • 51/2 Baths
  • 5,813 SqFt
  • $1,368/SqFt
Mid-Tier
House for sale in Gold Coast Of Captiva Island
16512 Captiva Dr, Captiva, FL 33924
Nestled along captiva island’s most coveted stretch of the gold coast, this exceptional beachfront private estate is surrounded by lush tropical landscaping, offering the ultimate blend of serenity and sophistication. Behind its unassuming beach house exterior lies a strikingly modern, european-inspired interior that radiates style and comfort. The main residence and guest house combine to offer 7 bedrooms and 5.5 baths, designed with expansive open living spaces and refined finishes throughout. Soaring ceilings, rich hardwood and shell stone flooring, and stunning custom woodwork create a timeless coastal ambiance. Walls of glass showcase panoramic gulf of mexico views and breathtaking sunsets from two levels of open living areas. Outdoors, enjoy the dramatic beachfront pool, spacious screened lanais, and a rooftop sundeck perfect for soaking in endless ocean vistas. With ample additional yard space offering room to expand, this architectural gem is a rare opportunity for those seeking a distinctive, sophisticated beach retreat on captiva island’s most desirable coastline.
Jose's Hideaway, 4620 Oro Pesos Ln, Upper Captiva, Florida 33924, image 1
Jose's Hideaway, 4620 Oro Pesos Ln, Upper Captiva, Florida 33924, image 2
Jose's Hideaway, 4620 Oro Pesos Ln, Upper Captiva, Florida 33924, image 3
$3,250,000 $250K
  • 4 Beds
  • 41/2 Baths
  • 2,115 SqFt
  • $1,537/SqFt
Mid-Tier
House for sale in Jose's Hideaway
4620 Oro Pesos Ln, Upper Captiva, FL 33924
Gulf-front luxury living on the pristine beaches of north captiva island, offering a rare two-lot homesite with sweeping panoramic views of the gulf of america, captiva pass, and cayo costa island, where unforgettable sunsets unfold nightly. Thoughtfully designed for comfort, resilience, and effortless island living, this exceptional residence features a whole-house reverse osmosis system, private well and septic (not shared), a 1, 000-gallon propane tank powering a full-house kohler generator, propane gas range, and tankless water heater to ensure uninterrupted comfort. The gourmet kitchen is equipped with high-end appliances and expansive west-facing sliders that frame breathtaking water views and open seamlessly to indoor-outdoor entertaining. Outdoor living is elevated with expansive deck space, a shaded area beneath the home, outdoor refrigerator and icemaker, heated saltwater pool, six-person spa, full outdoor entertainment system, and outdoor shower—ideal for hosting or relaxing after a day on the water. The spacious climate-controlled garage includes air conditioning, room for golf carts, bicycles, beach gear, a workbench, and a convenient service elevator with a 300-lb capacity for groceries and luggage. The fully fenced yard offers manicured green grass and a sprinkler system, a rarity on the island. Zoned for weekly rentals, this property presents outstanding investment potential while remaining a serene private retreat. Ownership includes a one-year membership to the island club at north captiva. Access is by private boat or ferry; overnight dockage is not included unless purchased separately, with two memberships available at safety harbor offering dockage and amenities—contact safety harbor for details. The private airstrip is available to members only through the salty approach association. A truly rare opportunity to own a gulf-front estate with scale, privacy, and flexibility—this two-lot offering delivers endless possibilities and will not last. Schedule your private showing today!
Gold Coast Of Captiva Island, 16632 Captiva Dr, Captiva, Florida 33924, image 1
Gold Coast Of Captiva Island, 16632 Captiva Dr, Captiva, Florida 33924, image 2
$5,699,000 $281K
  • 5 Beds
  • 4 Baths
  • 3,681 SqFt
  • $1,548/SqFt
Mid-Tier
House for sale in Gold Coast Of Captiva Island
16632 Captiva Dr, Captiva, FL 33924
A rare gulf-front estate opportunity on captiva island featuring approximately 100 feet of direct beachfront and estate owned multifamily entitlement, a combination virtually impossible to replicate under current zoning and coastal regulations. The property includes a 3 bedrooms, 3 baths main home with a 2 bedroom guest home, private pool, detached garage and beachside cabana and screened gazebo. The estate zoning with multifamily use sets this property apart for a custom legacy residence, multigenerational compound, or future redevelopment, while preserving the low density character of this stretch of captiva drive. Opportunities of this scale, frontage, and zoning are exceedingly limited and rarely come to market. A grandfathered shared bulkhead adds lasting value and provides direct bay access. Positioned among captiva’s most notable properties, this estate parcel delivers exceptional value to renovate or explore redevelopment opportunities!
33924, FL Snapshot
94
Active Inventory
0
New Listings
$150K to $18.9M
Price Tier
7
Pending Sales
$980K
Median Closed Price
0
Avg. Days On Market

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