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Upper Captiva, FL Real Estate For Sale

Lee County | Updated
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Castaway Key, 4491 Cutlass Dr, Upper Captiva, Florida 33924, image 1
$2,800,000
  • 5 Beds
  • 3 Baths
  • 2,514 SqFt
  • $1,114/SqFt
House for sale in Castaway Key
4491 Cutlass Dr, Upper Captiva, FL 33924
A legacy island estate designed for la buena vida ("the good life").  Some homes impress, and then some homes change your rhythm. Villas in the air is a spectacular luxury estate created for effortless island living, unforgettable gatherings, and moments that linger long after the sun slips below the horizon. Set on north captiva island, this expansive retreat offers a rare balance of scale, privacy, and resort-style amenities—where life slows down and every day feels intentional. From sunrise to sunset, the home unfolds in layers of connection and calm. Mornings begin on the screened terrace with coffee and the sound of distant waves. Afternoons drift by poolside, floating beneath blue skies or gathering at the outdoor bar as laughter carries on the breeze. Evenings rise to the rooftop porch, where a panorama of island views stretches endlessly with sunsets and stars that feel like a private performance just for you. Designed for both togetherness and retreat, the home offers multiple indoor and outdoor living spaces that allow everyone to spread out - yet always reconnect. The main living level stuns with soaring double-story ceilings and an open-concept great room, wrapped in refined contemporary coastal finishes. A restaurant-inspired kitchen anchors the space, connected to multiple dining areas that flow seamlessly indoors and out. Accommodations are generous and thoughtfully planned, offering five distinct sleeping retreats. The primary suite feels like a private sanctuary, complete with a spa-style bath and walk-in rain shower. Two additional king guest rooms share a beautifully appointed bath, while a detached poolside guest suite offers privacy and independence with its own en-suite bath. The third-floor retreat, featuring two queen beds and access to a spacious loft lounge, provides flexibility for guests, media space, or a relaxed sleeping haven. Outdoor living here is nothing short of exceptional. A heated pool, an expansive outdoor bar with tv, a rooftop terrace with panoramic water and preserve views, a grilling area, a wellness space, and multiple entertainment zones transform the property into a true private resort—designed for both quiet escapes and unforgettable celebrations.  Built to later codes with lasting materials like hardie board siding, impact-resistant windows, a metal roof, composite decking, and aluminum railings. Located on north captiva island, a boat-access-only barrier island celebrated for its pristine beaches, shelling, fishing, birdlife, and miles of preserve trails, this estate offers a lifestyle that can't be replicated on the mainland. Villas in the air is a legacy-quality island estate that is difficult to replicate - ideal as a private family retreat, a high-end luxury rental, or both. This is much more than just your average island home. It's a place where memories are made, traditions begin, and time finally slows down.
Castaway Key, 560 Gulf Ln, Upper Captiva, Florida 33924, image 1
$1,899,000 $301K
  • 2 Beds
  • 21/2 Baths
  • 1,650 SqFt
  • $1,151/SqFt
House for sale in Castaway Key
560 Gulf Ln, Upper Captiva, FL 33924
One of the most private and charming beach front homes ever for sale on north captiva island! This exquisite old florida cottage-style home offers true character and a a unique living experience with its one of a kind beachfront location. This rare lot is generously oversized, owning all the way to the mean high tide line... Surrounded on both sides by multiple non-buildable lots for unmatched privacy on the beach. The captivating charm of the cottage architecture & decor sets this home apart in a league all of its own. Every moment at this beach house is an all-encompassing retreat to nature and island life. The cottage interior features shiplap walls, tongue & groove ceilings, and meticulously painted woodwork with modern comforts like sleek kitchen countertops w/ stainless steel appliances. The eclectic style showcases handcrafted details, cozy nooks, and a warm ambiance that welcomes you at every turn. Ownership of this beachfront cottage is not just a home, but a serene sanctuary where timeless memories will be etched into the very fabric of your life. Don't miss your one and only chance to own this very special and unique property!
Jose's Hideaway, 4340 Sol Vista Dr, Upper Captiva, Florida 33924, image 1
$2,500,000
  • 4 Beds
  • 31/2 Baths
  • 2,120 SqFt
  • $1,179/SqFt
House for sale in Jose's Hideaway
4340 Sol Vista Dr, Upper Captiva, FL 33924
Stunning views with this exquisite 4 br, 31/2 ba home sitting directly on the beach. Unlike any other home available. Completely move-in ready. Turnkey! Including 3 golf carts. Totally renovated from top to bottom built to last with newest low maintenance materials: hardie board siding, impact windows and doors, metal roof and aluminum railings. Screened covered porches off of the 1st level bedrooms overlooking the bayside for spectacular sunrises. The views from the living level with a wall of windows are incomparable. To further accommodate the fabulous views the home was designed with an "upside down" floor plan, having the living space 2nd level and the bedrooms on the lower floor. The advantage of this is that the breeze and view are on the top where most of the day is spent and the cooler temps are enjoyed in the bedrooms. Step out to your own private beautiful sugar sand beach, plenty of room to add a pool. Steps to the small private airstrip and local amenities. Great potential to be a top performing rental property! Airstrip membership available for purchase. Seriously consider this amazing home and the value it presents, come and see its qualities for yourself.
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Safety Harbor Club, 412 Gulf Bend Dr, Upper Captiva, Florida 33924, image 1
$2,150,000
  • 4 Beds
  • 21/2 Baths
  • 1,807 SqFt
  • $1,190/SqFt
House for sale in Safety Harbor Club
412 Gulf Bend Dr, Upper Captiva, FL 33924
Best price for your own beach front home on north captiva island! Step down your private beach path to miles of pristine sandy beaches and the sparkling blue gulf of mexico. Recently upgraded with a new roof. This four-bedroom gulf-front home offers excellent outdoor living spaces, soaring cathedral ceilings, and a large kitchen with plenty of room for all your island culinary delight. The great room flows directly to a covered screen room with ample outdoor dining and relaxing space. Just outside is an open sundeck with beautiful views. Superb expansive water views from every level. Serenity will surround you at this island oasis and captivate your imagination from the top-level sunset room and porches. Enjoy views of the gulf, cayo costa island's beaches, and unforgettable sunsets from your lounge and decks. The common areas and green spaces adjacent to the north border of this home's oversized lot offer tremendous privacy. This home has shared dockage, pool, and tennis/pickleball courts as part of the safety harbor club community. If you have been looking for an affordable 4-bedroom beachfront home with privacy and dockage for your boat, you need to see this home!
640 Gulf Ln #3, Upper Captiva, Florida 33924, image 1
$1,390,000
  • 2 Beds
  • 2 Baths
  • 1,124 SqFt
  • $1,237/SqFt
Townhouse for sale
640 Gulf Ln #3, Upper Captiva, FL 33924
Motivated seller bring your offers! Prime island offering! Desired vacation rental! Rare is this unapparelled opportunity to own a gulf front and beach front luxury townhome in a spectacular location on butterfly beach! Attached, high end, brand new remodeled, gulf front and beach front! This turnkey villa called "beach dayz" offers two main owner suites and two full baths. This beach villa has undergone gorgeous and extensive renovations and both offer breath taking views of the gulf of mexico from its decks, porches, and balconies! Aside from the elegant brand new open kitchen & upscale baths, appliances, flooring, electrical, fixtures, fans, finish carpentry, paint, electric fireplaces, and turnkey furnishings, this amazing property has a brand new metal roof, hardie board siding, impact windows and doors, new whole house reverse osmosis water system, railings, stairs, and more. This turnkey furnished villa has fantastic rental history and potential! Located directly on the wide butterfly beach on the barrier island of north captiva with private beach access. The property's shoreline provides an abundance of the finest and most beautiful shells and its' gulf waters offers world class fishing! The islands state nature preserve is also only steps away. The islands sea and wildlife are magnificent to behold. An island club at north captiva memberships is available please inquire to enjoy their pools, spa, kayaks, fat tire bikes, basketball, activities and island services etc. Professional licensed property mgmt with upcoming rentals is already in place should you choose to enjoy your townhomes and/or value its’ rental income! This is a must see property located directly on the beach. Tropical and lush, this duplex sits in a spectacular location on island. *the entire duplex is also currently for available for sale please see 640 gulf ln #4* rare is this unparalleled opportunity to own an entire gulf front and beach front luxury duplex in a spectacular location on butterfly beach! Hurry to schedule your showings today!
640 Gulf Ln #4, Upper Captiva, Florida 33924, image 1
$1,450,000
  • 2 Beds
  • 2 Baths
  • 1,124 SqFt
  • $1,290/SqFt
Villa for sale
640 Gulf Ln #4, Upper Captiva, FL 33924
Motivated seller bring your offers! Prime island offering! Exquisite prime island beach front remodeled townhome “ocean waves”! Fantastic vacation rental or gulf front home! This high end, newly remodeled, gulf front and beach front townhouse makes up one half of this duplex property. This turnkey villa offers two main owner suites and two full baths. It has undergone gorgeous and extensive renovations and offers breath taking views of the gulf of mexico from its deck, porches, and balcony! Aside from the elegant brand open new kitchen with huge breakfast bar, upscale baths, appliances, flooring, electrical, fixtures, fans, finish carpentry, paint, electric fireplace, and turnkey furnishings, this amazing property has a brand new metal roof, hardie board siding, impact windows and doors, new whole house reverse osmosis water system, railings, stairs, and more. This turnkey furnished villa has fantastic rental history and potential gearing up for a busy florida winter season. Located directly on the wide butterfly beach on the barrier island of north captiva with private beach access. The property's shoreline provides an abundance of the finest and most beautiful shells and its' gulf waters offers world class fishing! The islands state nature preserve is also only steps away. The islands sea and wildlife are magnificent to enjoy! An island club at north captiva memberships is available please inquire to enjoy their pools, spa, kayaks, fat tire bikes, basketball, activities and island services etc. Professional licensed property mgmt with upcoming rentals is already in place should you choose to enjoy your townhomes and/or value its’ rental income! This is a must see property located directly on the beach. Tropical and lush, this duplex sits in a spectacular location on island. *the entire duplex is also currently for available for sale. Ask agents about unit 3! Rare is this unparalleled opportunity to own an entire gulf front and beach front luxury duplex in a spectacular location on butterfly beach!
Punta Robalo, 67 Kingfisher Dr, Upper Captiva, Florida 33924, image 1
$1,399,000
  • 2 Beds
  • 2 Baths
  • 884 SqFt
  • $1,583/SqFt
House for sale in Punta Robalo
67 Kingfisher Dr, Upper Captiva, FL 33924
Island living at its best, this private beachfront home is located on the far northern tip of the island, no public beach access nearby, giving you ultimate privacy and stunning views of the turquoise blue waters in your front yard. Offered turnkey including golf cart, ready for immediate move-in or rentals. Currently a very high volume vacation rental (occupied 250+days/yr with over $175k/yr in annual rent revs). The property is super low maintenance and recently completely remodeled! The ultimate relaxation spot, just walk right out to your private sandy white beach. Behind the property is over 6 acres of undeveloped preserve giving you total peace and quiet. Crisp coastal design inside, with everything you need to enjoy island living. Completely remodeled in 2023, new standing seam metal roof, hardie board siding, outdoor railings and lanai, top of the line low e hurricane windows, doors and sliders. All new hvac, water heater, stainless appliances, luxury vinyl plank flooring, fixtures and furniture. A magical island home or a profitable vacation rental, or both!
Jose's Hideaway, 4620 Oro Pesos Ln, Upper Captiva, Florida 33924, image 1
$3,500,000
  • 4 Beds
  • 41/2 Baths
  • 2,115 SqFt
  • $1,655/SqFt
House for sale in Jose's Hideaway
4620 Oro Pesos Ln, Upper Captiva, FL 33924
Gulf-front luxury living on the beach of north captiva island. Welcome to your private slice of paradise on the pristine shores of the gulf of mexico. This extraordinary home spans two large home sites strapped together and offers the ultimate in island living, where breathtaking sunsets paint the sky each evening. Panoramic views of the gulf, captiva pass, and cayo costa island. Thoughtfully designed for comfort, convenience, and style, this home features a whole-house reverse osmosis system, a 1, 000-gallon propane tank fueling a full-house kohler generator, a gas stove, and a tankless water heater. You can ensure you will never be without power. The gourmet kitchen is outfitted with high-end appliances, including a propane gas stove, perfect for entertaining. Sliders across the west to be sure not to miss the spectacular views. Large outdoor spaces with an elevated deck beneath the home, an outdoor refrigerator, and an icemaker. Host gatherings easily thanks to a heated saltwater pool, six-person spa, full outdoor entertainment system, and an outdoor shower. The spacious, climate-controlled garage includes a/c and extra room for golf carts, bicycles, beach gear, a work bench, and a convenient service elevator, making transporting groceries and luggage a breeze, holding up to 300 lbs. The fully fenced yard is complete with well-maintained green grass and a sprinkler system. Best of all, this home has its private well and septic, which is not shared. Whether you’re seeking a tranquil retreat or a spectacular space to entertain, this property offers unmatched comfort and coastal charm, all steps from the turquoise waters of the gulf of mexico. Don’t miss this rare opportunity to own a piece of paradise where every day ends with a front-row seat to one of the most beautiful sunsets in the world. This home has unlimited investment opportunities. Weekly rentals are popular on the island, and this retreat has the potential to make your investment a profitable one or for your enjoyment. With this two-lot site and endless opportunities, this will not last. This property comes with a one-year membership to the island club at north captiva. Come by boat or ferry. There are no overnight dock slips unless you purchase one. There are 2 memberships available in safty harbor with dockage and other amenities. Call safety harbor for details. The airstrip is utilized by members only. The association is known as salty approach. Schedule your private showing today.
Upper Captiva, FL Snapshot
39Active Inventory
0New Listings
$165K to $3.5MPrice Range
7Pending Sales
$790KMedian Closed Price
N/AAvg. Days On Market
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Broker reciprocity logoLocal Realty Service Provided By: Hyperlocal Advisor. Information deemed reliable but not guaranteed. Information is provided, in part, by Greater Miami MLS & Beaches MLS. This information being provided is for consumer's personal, non-commercial use and may not be used for any other purpose other than to identify prospective properties consumers may be interested in purchasing.

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