5+ Bedroom Homes For Sale in Captiva, FL

Results 25 of 25
Metes & Bounds, 11505 Gore Ln, Captiva, Florida 33924, image 1Metes & Bounds, 11505 Gore Ln, Captiva, Florida 33924, image 2
$3,990,000
$3,795,000
11505 Gore Ln, Captiva, FL 33924
MLS# 222081534
6
Beds
6
Baths
4,248
SqFt
4.9% Decrease (-$195,000)
2
Garage
$893
$/SqFt
Investor or primary home or vacation home alert! Just reduced $195,000. Since the home has so much $ in annual rental income, owner has not needed to sell, but does want to sell. You keep all that cash that rolls in every year. This lux captiva village beauty is waiting for you! Just a short 6 minute stroll to the aquamarine waters of the gulf. Have fun on the island of captiva, biking, fishing, swimming, putt-putting, golf cart riding over to the restaurants, etc. This 6br, 6bath, 2 car, heated pool+spa home has plenty of extra outdoor lounging areas, pool table room, lighted putt-putt green and more. Elevator to all 3 floors. Lr with gas fireplace. Primary br has 2 walk-in closets & fp & is on the 3rd floor, with 2 more guest suites on this floor, +2 more on the 2nd (main) floor and 1br+bath on the first floor. The ocean room has 4 full-sized bunkbeds! 8 tv’s in the house. The kitchen is beautiful with new s/s appliances, quartz counters, cabinets & fixtures. All new bath vanity counters/sinks/faucets installed throughout. Solid wood floors in the main areas have been redone to compliment the beach theme of the home, all done in gorgeous driftwood tones. The 1st floor has an open lanai area for lounging and cooking out by the pool+spa, and the 2nd & 3rd floors have open lanais. For sunrise across the back bay, or for sunning or an afternoon social go to the rooftop deck for amazing views and starlit nights. All vinyl siding removed and replaced with new lp smartside siding along with new soffits/fascia. New impact windows & doors! Great rental or make it your own primary home or vacation spot! You don't have to travel to the bahamas to appreciate island living! This.is.it! What are you waiting for? It is move-in ready, including all linens, furniture, art work, kitchenware, beach toys, golf clubs, beach towels and chairs and umbrellas. Lots of fun tchotchkes all throughout the house with pleasant
John R. Wood Properties
Captiva Beach, 11516 Wightman Ln, Captiva, Florida 33924, image 1Captiva Beach, 11516 Wightman Ln, Captiva, Florida 33924, image 2
$3,499,000
$3,395,000
11516 Wightman Ln, Captiva, FL 33924
MLS# 223070617
5
Beds
41/2
Baths
3,744
SqFt
3% Decrease (-$104,000)
2
Garage
$907
$/SqFt
This stunning home built by the wolter group in 2014 is proof of the strength of modern elevated construction and is priced below replacement cost. Within easy distance of the beach and captiva village, the design showcases quality construction and interior finishes. Comprising five bedrooms, 4.5 baths, a large open galleried living area, a chef’s kitchen with sub-zero refrigerator, 48-inch wolf range, multiple decks, a large rear lanai, and undeveloped ground floor storage space of 2,000 square feet. A 30-foot pool is surrounded by a paved area which runs the width of the lot. A new owner would have the option to continue this property as a spacious and comfortable family home or choose to take advantage of the significant rental potential with similar homes in captiva village generating gross rental income in excess of $300,000 per year.
Premier Sotheby's Int'l Realty
FA Lanes Bayview, 11516 Andy Rosse Ln, Captiva, Florida 33924, image 1FA Lanes Bayview, 11516 Andy Rosse Ln, Captiva, Florida 33924, image 2
11516 Andy Rosse Ln, Captiva, FL 33924
MLS# 224024767
6
Beds
6
Baths
3,092
SqFt
0.0%
2
Garage
$922
$/SqFt
For anyone seeking a project with the potential to build immediate equity, this home is listed for over $1.5 million below recent sales of andy rosse courtyard homes, which sold as high as $4.5 million (without impact windows/doors and still in need of remodeling). Being sold mid-construction, with no construction contract that needs to be honored, the home is being offered in as-is condition. The exterior and roof have been wrapped in waterproofing underlayment since hurricane ian. The current owner replaced the exterior doors and windows with hurricane-rated windows and sliders. Located on arguably the premier street in captiva village, this home's design is one of the most popular courtyard-style homes built by the developer, offering the largest guest house with the main residence set back from the street. The home's construction is concrete pilings and concrete block walls throughout the ground floor. Home features include a pool with a spa, an attached two-bedroom guest house, an in-home elevator, and a convenient location just a few parcels from the beach or shopping. Once completed, rental estimates project this home could earn around $300,000 annually.
Premier Sotheby's Int'l Realty
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Metes & Bounds, 16486/488 Captiva Dr, Captiva, Florida 33924, image 1Metes & Bounds, 16486/488 Captiva Dr, Captiva, Florida 33924, image 2
$9,500,000
$8,495,000
16486/488 Captiva Dr, Captiva, FL 33924
MLS# 225008480
6
Beds
81/2
Baths
9,026
SqFt
10.6% Decrease (-$1,005,000)
4
Garage
$941
$/SqFt
Discover the pinnacle of private gulf-front living along captiva island’s exclusive gold coast. This magnificent gated estate is a rare and extraordinary beachfront sanctuary, offering a seamless blend of seclusion, sophistication, and breathtaking natural beauty. Set on a one-of-a-kind parcel with direct access to captiva’s pristine sugar-sand beaches, this remarkable family compound delivers an unrivaled connection to the turquoise waters of the gulf of mexico and awe-inspiring sunsets. The grand main residence boasts six bedrooms and six-and-a-half baths, each crafted with exquisite architectural details and unparalleled craftsmanship. A two-story great room with soaring coffered ceilings, a gas fireplace, and panoramic gulf views creates a dramatic yet inviting atmosphere. The formal dining room is elegantly appointed, while the gourmet kitchen is a chef’s dream, fully equipped with top-tier appliances and custom finishes. A one-of-a-kind, hand-painted private elevator adds an artistic touch to this coastal masterpiece. Designed for both privacy and indulgence, each bedroom suite features private balconies and screened lanais, providing serene gulf breezes and unobstructed sunset views. The primary retreat is a sanctuary unto itself, offering his-and-her spa-inspired baths, a soaking tub, dual showers, double vanities, a morning bar, and expansive walk-in closets. Step onto your private screened lanai and take in the breathtaking ocean vistas as the waves roll onto the shore. An expansive coquina stone veranda surrounds the heated saltwater pool and spa, creating the perfect setting for luxurious outdoor living and entertaining. Six conveniently placed laundry rooms add to the home’s seamless functionality. The oversized two-car garage offers massive storage beneath the home for added convenience. A charming guest cottage enhances the estate, featuring two en-suite bedrooms, a full kitchen with breakfast bar, a spacious living area, and a private covered terrace. Additional amenities include two garages at the guest house, a large workshop, and ample storage space for all your island essentials. This exclusive beachfront oasis embodies the epitome of island luxury. Whether you seek a private sanctuary or an entertainer’s dream retreat, this captiva estate is truly a rare gem that exceeds expectations....your paradise awaits. Property can be purchased with 16475 captiva drive for a rare gulf to bay opportunity!
Douglas Elliman Florida,LLC
Gold Coast Of Captiva Island, 16321 Captiva Dr, Captiva, Florida 33924, image 1Gold Coast Of Captiva Island, 16321 Captiva Dr, Captiva, Florida 33924, image 2
$3,950,000
$3,495,000
16321 Captiva Dr, Captiva, FL 33924
MLS# 223031399
5
Beds
4
Baths
3,522
SqFt
11.5% Decrease (-$455,000)
2
Garage
$992
$/SqFt
Welcome to turtle run! A stunning bayfront property located on the picturesque roosevelt channel. This magnificent estate offers an unparalleled combination of serenity, comfort, and natural beauty. Nestled on a parcel spanning over 1.8 acres, this property boasts over 100 feet of bay frontage, while providing views of buck key. The main residence features 3 bedrooms, 2 bathrooms, an open-concept floor plan, vaulted ceilings, and hardwood flooring. The living and dining areas flow seamlessly, making it ideal for entertaining guests or simply enjoying the tranquility of the surroundings. The property also includes a guest house with 2 suites, a kitchen, living room and patio providing ample accommodation for guests or extended family. Experience the ultimate florida lifestyle with an array of outdoor amenities. The multi-level decking is a perfect spot for unwinding, while the oversized pool provides a refreshing relief from the warm florida days. Hop on the boat via your own private dock for a quick ride to cayo costa, cabbage key or the open waters of the gulf! Turtle run offers an extraordinary opportunity to experience the best of captiva island living and beach access.
John R. Wood Properties
Metes & Bounds, 15160 Captiva Dr, Captiva, Florida 33924, image 1Metes & Bounds, 15160 Captiva Dr, Captiva, Florida 33924, image 2
$4,990,000
$4,900,000
15160 Captiva Dr, Captiva, FL 33924
MLS# 224081624
6
Beds
61/2
Baths
4,857
SqFt
1.8% Decrease (-$90,000)
3
Garage
$1,009
$/SqFt
Experience the charm of sandcastle, a stunning coastal estate with a unique reverse floor plan. This impressive 6-bedroom + den, 6.5-bath residence spans over 4,800 square feet, offering breathtaking bay views from its multi-level decks. Designed in coastal tuscan style, the home features luxurious touches throughout, including travertine floors in the living areas, wood floors in the bedrooms, and soaring 10+ ft ceilings with elegant crown molding. The spacious layout boasts multiple living rooms, en-suite bedrooms, an elevator, a morning kitchen, and a private in-law suite. The chef’s kitchen is a culinary dream, featuring a gas stove, stainless steel appliances, granite countertops with a breakfast bar, a walk-in pantry, custom wood cabinetry, an oversized sink, and a dedicated bar area. Enjoy the #islandlifestyle with your private pool and spa, multiple covered and open patios, or a short walk to the beach. Sandcastle is conveniently located near the village, renowned restaurants, and plenty of shopping, offering everything you need to embrace the #captivalifestyle.
John R. Wood Properties
Metes & Bounds, 16979 Captiva Dr, Captiva, Florida 33924, image 1Metes & Bounds, 16979 Captiva Dr, Captiva, Florida 33924, image 2
$6,394,900
$5,694,900
16979 Captiva Dr, Captiva, FL 33924
MLS# 224097316
6
Beds
71/2
Baths
5,598
SqFt
8.5% Decrease (-$700,000)
2
Garage
$1,017
$/SqFt
Deeded beach access! Opportunity is knocking! Answer the door! One of captiva's most iconic residences resting on over 2.5 acres with 200 ft of bay-frontage overlooking the sparkling waters toward the preservation land beyond. Situated on a peninsula this property affords unparalleled wide water views unlike any other on the islands. As you approach up the shell drive you are surrounded by mature specimen plantings from around the globe that can only come with decades of establishment and deliberately arranged garden paths highlighting many exotic species. Upon arrival you are greeted with bay views before even entering due to the wonderful breezeway design which looks through to the wrap-around covered boat basin and gazebo. As you enter, you are welcomed with a hand forged cascading stairway which brings you to the interior for a knockout view. This sprawling one level home design is only possible because of the double water frontage of 200ft. Unequivocally the ultimate home for entertaining, with a massive relaxing area along with a knockout outdoor kitchen, spa and huge pool with billiards and more. Beautifully remodeled with a cool coastal feel that blends well with the architecture. Deeded beach access.
Kingfisher Real Estate, Inc.
Gold Coast Of Captiva Island, 16309 Captiva Dr, Captiva, Florida 33924, image 1Gold Coast Of Captiva Island, 16309 Captiva Dr, Captiva, Florida 33924, image 2
$5,350,000
$4,950,000
16309 Captiva Dr, Captiva, FL 33924
MLS# 225012304
6
Beds
41/2
Baths
4,862
SqFt
7.5% Decrease (-$400,000)
2
Garage
$1,018
$/SqFt
This sprawling estate along roosevelt channel on captiva's gold coast is as breathtaking as it is private. The modest shell drive, hidden by vegetation, is designated by a small sign that reads "le jardin" or "the garden." feel the tropical vegetation welcome you with palm trees, citrus groves and beautiful flowers as you make your way down the shell drive of this almost two-acre waterside estate. The first building you arrive at is a quaint guest cottage with a full kitchen, living room, bedroom and bath tucked away in the gardens and ideal for guests or caretakers. Venturing further down the winding shell drive takes you to the garage and storage building ideal for all your favorite modes of conveyance over land and water. Venturing further into the estate brings you to the beautiful pool house where beamed ceilings, a stone fireplace, and small kitchen and bedrooms surround a wonderful entertaining area with pool table or ping-pong table, dining area and living room, all off the large caged swimming pool. A beautiful roundabout ends at the three-story main house along the roosevelt channel. The beautiful old florida inspired home is tucked along the water offering gorgeous views from almost every room. The large kitchen with gas range is ideal for entertaining as friends and family gather beside the fireplace. The large porches are wonderful for watching all the wildlife the roosevelt channel hosts, including boats lazily floating by. Along the channel you'll find your private dock and lift where a day of boating beckons you onto the tropical waters to fish, island hop or pop into a waterfront restaurant. You can also slide a kayak into the water and explore the natural and protected buck key just across the channel or enjoy a peaceful moment by the water under the shade of your thatched tiki hut. This is one of those rare properties where time stands still, and the fast pace of life is left by the entrance to your amazing garden.
Premier Sotheby's Int'l Realty
15557 Captiva Dr, Captiva, Florida 33924, image 115557 Captiva Dr, Captiva, Florida 33924, image 2
$4,095,000
$3,589,000
15557 Captiva Dr, Captiva, FL 33924
MLS# 223085708
5
Beds
41/2
Baths
3,485
SqFt
11.3% Decrease (-$506,000)
3
Garage
$1,030
$/SqFt
A fantastic waterfront property along the tween waters area, overlooking the bay & roosevelt channel on captiva island. This home radiates a gentle mediterranean ambiance, enriched with travertine marble & cherry wood flooring, tailor-made cabinetry, & top-tier wolf kitchen appliances. The layout includes a spacious great room w/ Stunning bay views, a large 2nd floor media family room, a sophisticated lutron lighting system, full house generator & water filtration system. Features also include elevator, a secure lower level, & three-car garage. Unique in its offering, this home combines the privacy & space of a single-family house with the perks of condominium living. Residents enjoy a lifestyle that spans from beach to bay, including boat docking facilities, a community pool, & exclusive beach access. The association manages external maintenance, including roofing & landscaping, plus insurance, making the cost of ownership ideal. Incredible weekly rental making it a fantastic income-producing investment property while you also enjoy personally. This property is a great value w/ Stress-free, low cost, waterfront living, boating & beach.
Royal Shell Real Estate, Inc.
Metes & Bounds, 16585 Captiva Dr, Captiva, Florida 33924, image 1Metes & Bounds, 16585 Captiva Dr, Captiva, Florida 33924, image 2
$5,750,000
16585 Captiva Dr, Captiva, FL 33924
MLS# 225032643
5
Beds
42/2
Baths
4,630
SqFt
0.0%
2
Garage
$1,242
$/SqFt
Located on nearly 2 acres of pristine captiva island waterfront, this coastal estate offers unparalleled privacy and direct access to the roosevelt channel. With a private dock and boat lift, you’ll enjoy seamless access to the intracoastal waterway and the gulf of mexico, making it an ideal location for fishing, boating, and water enthusiasts. This fully furnished, move-in-ready home boasts expansive living spaces, including five bedrooms, four full baths, and two half baths, all thoughtfully designed for comfort and style. The open-concept living area flows effortlessly onto a spacious pool deck, offering the perfect setting for outdoor entertaining. A raised pool and hot tub enhance the experience, providing a seamless transition between indoor and outdoor spaces. Inside, the home has been beautifully updated with a chef’s kitchen featuring high-end appliances, quartz countertops, and custom tile work. The attention to detail is evident throughout, from the wood floors and crown molding to the metal roof and impact windows. Other standout features include a custom built-in bar area, a gas fireplace, and a crow’s nest offering breathtaking views of both the gulf and the bay. For added convenience, a full home generator ensures peace of mind, and the home is equipped with hardi-board siding. An elevator accesses all floors, adding an extra layer of ease and accessibility to the home. Additionally, you’ll have deeded beach access just a short walk away, giving you the best of both worlds—beachfront relaxation and boating adventures. This estate is a rare gem, blending modern luxury with the natural beauty of captiva island.
Pfeifer Realty Group LLC
Dickeys John, 15891 Captiva Dr, Captiva, Florida 33924, image 1Dickeys John, 15891 Captiva Dr, Captiva, Florida 33924, image 2
$6,750,000
$6,100,000
15891 Captiva Dr, Captiva, FL 33924
MLS# 224045415
5
Beds
41/2
Baths
4,729
SqFt
9.4% Decrease (-$650,000)
2
Garage
$1,290
$/SqFt
Opulent bay front retreat with endless potential on captiva island! Nestled on a prime bay front parcel, this distinguished residence offers unobstructed vistas of shimmering waters, deeded beach access, and a private boat dock, providing an enchanting backdrop for daily indulgence and relaxation. Boasting an expansive layout and timeless architectural charm, this home presents a canvas for creativity and personalization, inviting you to unleash your imagination and transform it into a bespoke sanctuary tailored to your unique vision. With its privileged location on captiva island, residents enjoy access to a host of exclusive amenities and recreational pursuits, from world-class boating and fishing to pristine beaches and eclectic dining options. Rainbow's end, bayfront, with the option to purchase this estate separately or collectively with the gulf front "paradise found" estate creating the ultimate gulf-to-bay compound and waterfront experience.
Premier Sotheby's Int'l Realty
Gold Coast Of Captiva Island, 16512 Captiva Dr, Captiva, Florida 33924, image 1Gold Coast Of Captiva Island, 16512 Captiva Dr, Captiva, Florida 33924, image 2
$9,000,000
$7,950,000
16512 Captiva Dr, Captiva, FL 33924
MLS# 222057371
6
Beds
51/2
Baths
5,813
SqFt
10% Decrease (-$1,050,000)
0
Garage
$1,368
$/SqFt
Nestled within a lush tropical estate setting & located along the best stretch of the gold coast of captiva island is this fantastic beachfront private estate. The home offers an unassuming beach house feel from the outside yet enjoys an exciting, modern, euro feel interior inside. The home is very spacious & open in both the main & guest house areas w/ Complete amenities. Stunningly appointed & professionally designed this is a true architectural highlight for the buyers searching for true comfort w/in a unique sophisticated beach home. Main residence & guest house features 7 bedrooms, 5.5 baths w/dramatic beach side pool & large screened lanai areas. Enjoy panoramic sunset views of the gulf of mexico from 2 levels of large open fixed windows. Gorgeous hard wood & shell stone floors thru out. Beautiful wood work. Soaring ceilings. Roof top sundeck. Lots off additional yard space to enjoy or add onto!
Royal Shell Real Estate, Inc.
Metes & Bounds, 17181 Captiva Dr, Captiva, Florida 33924, image 1Metes & Bounds, 17181 Captiva Dr, Captiva, Florida 33924, image 2
$6,975,000
17181 Captiva Dr, Captiva, FL 33924
MLS# 225006448
5
Beds
41/2
Baths
4,737
SqFt
0.0%
3
Garage
$1,472
$/SqFt
You really can have it all! Boating on the bayside and the beach at your door. An unparalleled setting with tremendous views from every room of this exceptional residence that enjoys stunning sunrises, and phenomenal sunsets. 150 ft of linear gulf frontage allows for 180* unobstructed views of the gulf ofmexico. As you enter this commanding residence, your eye is drawn through the great room, to the bayside with its abundance of daily wildlife. Five ensuite bedrooms ensure privacy and comfort, while a private elevator and temperature-controlled wine room enhance convenience and luxury. The first level offers tremendous storage, and the home is being sold as-is. The buyer will assume responsibility for landscaping, irrigation, and repairs to the ground-level storage area. Interior areas sustained no damage ;trim was removed in preparation for window and door replacement, which will also be the buyers responsibility. Some west-facing windows have already been upgraded to impact glass. With eight brand-new ac systems and offered well below duplication cost, this home presents unmatched potential in a truly one-of-a-kind location.
Kingfisher Real Estate, Inc.
Tarpon Bay At Captiva, 11550 Paige Ct, Captiva, Florida 33924, image 1Tarpon Bay At Captiva, 11550 Paige Ct, Captiva, Florida 33924, image 2
11550 Paige Ct, Captiva, FL 33924
MLS# 225018787
5
Beds
52/2
Baths
4,129
SqFt
0.0%
2
Garage
$1,574
$/SqFt
On the serene shores of captiva island, in the exclusive community of tarpon bay, this gulf-front estate epitomizes luxury coastal living. Boasting gulf and bay access, residents here enjoy the best of both worlds, a private deeded beach for shell-seekers and direct access to pine island sound for boating enthusiasts. The key west-style architecture of the main home and attached guest house reflects the relaxed yet sophisticated ambiance of island living. Every detail speaks to the quality and craftsmanship expected in a home of this caliber, with numerous upgrades enhancing comfort and style. Adding convenience, a private elevator provides easy access between floors. Entertainment is effortless with a resort-style pool featuring a cascading spa, complemented by an expansive outdoor area ideal for gatherings and relaxation. Set on a sprawling one-acre home site, the property offers a tranquil park-like setting, perfect for enjoying the island's natural beauty and privacy. This gulf-front estate on captiva island not only offers luxurious living spaces and top-tier amenities but also provides unparalleled access to the gulf. Welcome home!
Premier Sotheby's Int'l Realty
16886 Captiva Dr, Captiva, Florida 33924, image 116886 Captiva Dr, Captiva, Florida 33924, image 2
$7,500,000
16886 Captiva Dr, Captiva, FL 33924
MLS# 225026465
5
Beds
41/2
Baths
4,608
SqFt
0.0%
4
Garage
$1,628
$/SqFt
Rare beachfront estate with separate guest home on captiva island seize the rare opportunity to own a private beachfront estate on the coveted gold coast of captiva island. Nestled on over an acre of land, this exquisite property features a breathtaking architectural design that seamlessly blends with nature, maximizing panoramic waterfront views and enhancing the exceptional outdoor living experience. The main home has been meticulously remodeled with high-end finishes, offering soaring beamed ceilings, an elevator, two-master suites and multiple garage spaces and storage areas. The open layout invites abundant natural light, providing an ideal setting for entertaining or relaxing with family. The separate two-bedroom guest home boasts a private lanai and its own garage, offering comfort and privacy for visitors or extended family. With 100 feet of pristine gulf of mexico beachfront, this estate is a rare gem on the island, situated amidst award-winning beaches. The expansive property offers unparalleled privacy and direct access to captiva’s renowned natural beauty. Additionally, there is an exclusive opportunity to acquire the adjacent 1.4-acre bayside estate, complete with an artist’s studio, home, private dock, and pool. This additional parcel further elevates the potential of this once-in-a-lifetime property offering. Don’t miss out on this exceptional piece of captiva island paradise!
Kingfisher Real Estate, Inc.
Punta Robalo, 211 Kingfisher Dr, Captiva, Florida 33924, image 1Punta Robalo, 211 Kingfisher Dr, Captiva, Florida 33924, image 2
$6,750,000
$6,500,000
211 Kingfisher Dr, Captiva, FL 33924
MLS# 223057382
5
Beds
5
Baths
3,938
SqFt
3.4% Decrease (-$250,000)
1
Garage
$1,651
$/SqFt
Exclusive island estate with spectacular views of pine island sound and the gulf of mexico. This 5 bedroom, 5 bath home is situated on 1.16 acres of beautifully landscaped, irrigated property with 300' of white sandy beach. The waterfront includes new trex dock with 2 boatlifts, one at 20,000 lbs. New copper roof installed in 2020. Adjacent to the the island's 1600' runway, the location provides direct access to the home's hanger. Hurricane-rated windows and doors with hurricane roll down protection on the screened porch. Chef's kitchen includes top of the line appliances with propane cooktop, wine and beverage refrigerators in the wet bar. Exquisite marble floors throughout the living area. Well equipped work out room with sunlighten infrared sauna. Outside by the bay enjoy the pool with cabana, outdoor kitchen, covered porch and private open air shower. Elevator to 4 levels. Whole house generator. The fifth level widow's walk offers one of the highest panoramic views on upper captiva, giving you views of the gulf, captiva pass and pine island sound.
Century 21 Sunbelt Realty
Gold Coast Of Captiva Island, 16632 Captiva Dr, Captiva, Florida 33924, image 1Gold Coast Of Captiva Island, 16632 Captiva Dr, Captiva, Florida 33924, image 2
16632 Captiva Dr, Captiva, FL 33924
MLS# 225000107
5
Beds
4
Baths
3,681
SqFt
0.0%
1
Garage
$1,698
$/SqFt
Welcome to halemakai, a coastal sanctuary nestled on captiva's gold coast. This exceptional property boasts an impressive 100 feet of pristine gulf frontage, radiating coastal elegance. This property presents a unique opportunity to craft your dream retreat or enhance its existing structures. The current layout features a stunning gulf-front main house with three inviting bedrooms, a spacious den that can adapt to your needs, a fireplace, and a luxurious primary suite on the upper level that offers a private balcony overlooking the shimmering gulf of mexico. Just steps away, a delightful guest house awaits, offering two bedrooms, a bathroom, and a combined kitchen/living area, perfect for hosting friends and family. As you pass through the entry gates, you'll discover a separate garage ensuring convenience. The outdoor oasis is nothing short of enchanting, featuring a screened pavilion, a gulf front cabana, a private pool and a picturesque boardwalk leading directly to the beach. Surrounded by lush tropical foliage, this property provides the ultimate seclusion and tranquility, ideal for savoring the breathtaking sunsets that illuminate the coastline. Halemakai is truly a rare gem, offering an unparalleled coastal lifestyle with direct bay access via a shared bulkhead. Whether seeking peaceful solitude or unforgettable gatherings by the sea, this luxurious property delivers the ultimate coastal lifestyle where your vision of paradise can come to life.
John R. Wood Properties
16777 Captiva Dr, Captiva, Florida 33924, image 116777 Captiva Dr, Captiva, Florida 33924, image 2
$9,450,000
16777 Captiva Dr, Captiva, FL 33924
MLS# 224082961
6
Beds
61/2
Baths
5,346
SqFt
0.0%
3
Garage
$1,768
$/SqFt
A one of a kind offering with 150ft of water frontage laden with rich national history. President theodore roosevelt began frequenting captiva in 1908. In 1917 he staged his houseboat at this very location for his legendary devil fish expedition of which he hunted and gathered for the smithsonian. In the 1930s this property served as one of only two locations to deliver goods to captiva mainly of which was building materials, delivered by barge. the oversized grandfathered dock was built in 1939 by the wpa which was founded by franklin roosevelt. The romantic boathouse, which is cantilevered over the water and is also grandfathered in, was constructed in 1953 by harold bixby. Bixby was one of charles lindbergh's primary backers in 1927 when lindbergh accomplished his transatlantic flight in the spirit of st louis. The boathouse with two bedrooms and caretaker cottage with one bedroom stand today in superb condition with a recently installed composite roof with a 100 year life expectancy. As you approach the main house, you are greeted with the charm of olde world southern architecture. Inside you will find soaring ceilings of cypress, and beautiful views of roosevelt channel along with three spacious bedrooms, a library and an office. Resting on over 1.3 acres with deeded beach access.
Kingfisher Real Estate, Inc.
16500 Captiva Dr, Captiva, Florida 33924, image 116500 Captiva Dr, Captiva, Florida 33924, image 2
$8,495,000
$7,895,000
16500 Captiva Dr, Captiva, FL 33924
MLS# 224103898
6
Beds
61/2
Baths
4,000
SqFt
7.1% Decrease (-$600,000)
3
Garage
$1,974
$/SqFt
Welcome to a breathtaking coastal-modern beachfront estate on captiva island’s exclusive gold coast! Designed for peace & rejuvenation, this home blends comfort, nature, & luxury into a seamless oasis. Set on over 100 feet of beachfrontage, this estate-zoned property offers the ability to add two additional structures, creating your ultimate private retreat. This meticulously enhanced home features stunning gulf views, luxurious amenities, & unmatched privacy. With 6 spacious bedrooms, each with en-suite baths, the expansive layout is perfect for entertaining. Highlights include family gathering spaces, a media room, & an elevator. The great room’s floor-to-ceiling sliding glass doors create a seamless indoor-outdoor flow, while the kitchen impresses with panoramic views, high-end appliances, & a coffee bar. Outdoor enthusiasts will love the atrium-style, 44-ft heated saltwater pool, offering total privacy. Expansive decks on every level provide breathtaking water views, with a rooftop sun deck perfect for champagne sunsets. Beyond its luxury, this property is a proven high-income rental powerhouse, consistently generates well over $500k in annual rental income. The proven detailed rental history makes it a turnkey opportunity for investors, with an established track record of strong returns. Whether you’re seeking a luxurious beachside retreat or an investment property with exceptional income potential, this captiva escape is the ultimate!
Royal Shell Real Estate, Inc.
16530 Captiva Dr, Captiva, Florida 33924, image 116530 Captiva Dr, Captiva, Florida 33924, image 2
$12,500,000
16530 Captiva Dr, Captiva, FL 33924
MLS# 225024734
5
Beds
51/2
Baths
5,843
SqFt
0.0%
3
Garage
$2,139
$/SqFt
The crown jewel of captiva island, the one and only sandpiper estate. For the first time ever, the iconic sandpiper estate is available for purchase, presenting an extraordinary opportunity to own a legacy property on captiva island’s prestigious gold coast. Spanning 200 feet of prime sandy beach frontage, this breathtaking estate is a rare sanctuary where timeless elegance meets coastal tranquility. Designed for privacy, relaxation, and entertaining, the estate has been cherished for over 40 years as a treasured family retreat and now, it’s ready for its next fortunate owner. The main residence is a masterpiece of waterfront luxury, featuring 3-4 private bedrooms, a spacious central gathering area, and a fantastic kitchen with panoramic gulf views. A grand dining area offers an elegant setting for entertaining, while a private study provides a quiet retreat. The home seamlessly blends indoor and outdoor living, with an expansive screened lanai, multiple lounging decks, and breathtaking views from every angle. The outdoor spaces feel like a private resort, complete with a spectacular pool area offering unparalleled privacy and stunning waterfront views. Just off the pool, a charming beachside bungalow provides additional accommodations with two guest suites, each with en-suite baths, and a spacious family room for relaxing by the shore. The estate also includes a private tennis court, an additional 2 br guest house or caretakers quarters, and lush tropical landscaping, creating a secluded and serene retreat. For those seeking the ultimate private estate, two adjacent properties, owned by this same owner, 16548 captiva drive and 16543 captiva drive are also available, allowing for the creation of an unmatched beach to bay front compound that offers a total of 300 ft of beach frontage, 100 ft of bay frontage with well over 5.25 acres total. This opportunity is more than a home; its a once-in-a-lifetime opportunity to own an iconic piece of captiva island.
Royal Shell Real Estate, Inc.
South Seas Plantation Resort, 1119 Schefflera Ct, Captiva, Florida 33924, image 1South Seas Plantation Resort, 1119 Schefflera Ct, Captiva, Florida 33924, image 2
1119 Schefflera Ct, Captiva, FL 33924
MLS# 224058110
5
Beds
41/2
Baths
4,479
SqFt
0.0%
2
Garage
$2,233
$/SqFt
Sosianna - the epitome of coastal luxury! This stunning 5-bedroom+den, 4.5-bathroom home, is situated within the gates of south seas resort. Masterfully designed and renovated, this residence features only the finest materials and finishes. Enjoy the durability and style of a standing seam aluminum roof, hardie board siding, and hurricane-rated impact windows. The property also includes a commercial 45kw generator, aluminum railings, multi-level decks and premium composite decking. Inside, savor panoramic gulf views from your spacious living areas adorned white oak wood flooring, shaker wood cabinetry, and linear fireplace. The culinary kitchen boasts quanta quartz waterfall island and countertops, blue wave glass backsplash, audra pendant lighting, premium appliances including beverage cooler and drawers. Coastal side den exudes tailor-made cabinetry, bastian over-size chandelier, and stunning vistas! The guest suite is beyond the elevator providing its own privacy wing. Meticulously crafted landscaping and lighting for an impeccably manicured ambiance combined with security cameras. Situated on one of the most coveted private streets, this property offers unparalleled proximity to the beach, complete with a private pool, tennis courts, and pickleball courts. Despite the serene privacy, you're just steps from the beach and minutes from renowned restaurants, retail shops, and a variety of outdoor activities. Embrace coastal living at its finest in this exquisite captiva home.
John R. Wood Properties
16770 Captiva Dr, Captiva, Florida 33924, image 116770 Captiva Dr, Captiva, Florida 33924, image 2
$9,700,000
16770 Captiva Dr, Captiva, FL 33924
MLS# 225000142
5
Beds
41/2
Baths
4,134
SqFt
0.0%
3
Garage
$2,346
$/SqFt
South haven—experience unparalleled tropical luxury at south haven, a meticulously designed concrete piling home that seamlessly blends elegance and functionality. Recent enhancements include a fully remodeled kitchen, dining room, and primary bath, along with a 2023 roof replacement and premium finishes throughout. The main level features a sunlit foyer, guest accommodations, and dual guest retreats in a private wing. The redesigned kitchen boasts modern amenities and a bright dining nook, while the living room offers sweeping coastal views. Upstairs, the owner’s suite captivates with gulf of mexico vistas, a stone-clad electric fireplace, and sophisticated woven flooring. The ground level includes a spacious garage and versatile spaces, all accessible via an elevator serving every level. Outside, royal palms frame the exquisitely designed pool area, complete with a sunbathing platform, covered dining, and lounging spaces. A beachside yard features a private cabana, landscaped greens, and a serene walkway to the shore. South haven is the ultimate coastal retreat, offering exceptional craftsmanship, lush surroundings, and unforgettable sunsets.
John R. Wood Properties
Dickeys John, 15735/737 Captiva Dr, Captiva, Florida 33924, image 1Dickeys John, 15735/737 Captiva Dr, Captiva, Florida 33924, image 2
$13,995,000
15735/737 Captiva Dr, Captiva, FL 33924
MLS# 225007259
5
Beds
51/2
Baths
5,751
SqFt
0.0%
2
Garage
$2,433
$/SqFt
Embraced by the sparkling waters of the gulf & the mesmerizing bay, this extraordinary estate, dolphins crossing, offers unparalleled luxury and rare waterfront living. Spanning from gulf to bay, this breathtaking property is truly a unique find. A special aspect of this iconic estate is the historic boathouse, expertly curated as a charming & updated guest cottage with timeless character, and magnificent bay views. The main residence is a spectacular blend of elegance and comfort, featuring breathtaking & expansive living spaces with panoramic gulf & bay views, coral rock/shell stone flooring throughout, custom designs and finishes throughout, & a chef's kitchen that will inspire culinary creativity. Impressive indoor and outdoor entertaining areas seamlessly connect, including an expansive outdoor area framed by a sparkling pool and spa. From the huge garage to the top floor guest suites, the added comfort features are too numerous to mention. With direct access to both the gulf & bay, this estate offers the ultimate island lifestyle. Dolphins crossing presents a rare opportunity to own a piece of history while enjoying the finest in modern luxury living. This is more than just a home - it's a legacy.
Kingfisher Real Estate, Inc.
16950 Captiva Dr, Captiva, Florida 33924, image 116950 Captiva Dr, Captiva, Florida 33924, image 2
$23,000,000
16950 Captiva Dr, Captiva, FL 33924
MLS# 225006221
6
Beds
7
Baths
8,596
SqFt
0.0%
3
Garage
$2,676
$/SqFt
Arguably the most architecturally significant home to ever be brought to market on captiva, bella luna was nationally recognized for impeccable design when it received the american institute of building design’s (aibd) prestigious american residential design award (arda) in 2021. Conceptualized by the renowned wayne visbeen of visbeen architects, bella luna reflects the exceptional craftsmanship and innovative design for which the firm is celebrated. Known for collaborating with prestigious clients such as the metropolitan museum of art, martha stewart, and disney, visbeen architects brings the same level of artistry and attention to detail to residential projects, making this property a masterpiece of design and livability. Constructed to be a fortress of concrete and steel, the substantial nature of the structure is resilient yet refined. Employing hotel and hospitality design techniques, every detail was meticulously tailored to enhance the human experience through sophistication and functionality, creating intimate experiences in the grandeur of larger spaces. A 24-foot fully retractable wall of glass seamlessly unites the indoors with the 4,000-plus-square-foot outdoor entertainment deck featuring a 1,575-square-foot resort-style pool with 360-degree spillover spa and an impressive 48-foot negative edge waterfall wall accentuated by fountain bowls on either end. For entertaining poolside, the luxurious cabana-kitchen can connect to the adjacent primary kitchen by opening the wall of disappearing sliders. Embodying a commercial functionality with sophisticated quality, the kitchen is timelessly beautiful and practical for the professional chef or home cook featuring industry-leading appliances including 48-inch wolf dual fuel range, miele coffee machine, sub-zero refrigeration and freezer towers, and dual cove dishwashers. A feature sheet is available detailing the extensive upgrades, features and breathtaking attributes.
Premier Sotheby's Int'l Realty
16814 Captiva Dr, Captiva, Florida 33924, image 116814 Captiva Dr, Captiva, Florida 33924, image 2
$17,500,000
16814 Captiva Dr, Captiva, FL 33924
MLS# 225030790
6
Beds
52/2
Baths
6,500
SqFt
0.0%
3
Garage
$2,692
$/SqFt
PRECONSTRUCTION ~Est. 2025
Resilience. Romance. Rarity. Excitement. History.... Once in a great while, something truly remarkable emerges—something so rare and special, it's reserved for only a select few. This is one of those moments. Welcome to a captivating beach estate that embodies over a century of history, elegance, and coastal charm. Originally constructed in 1912 as part of the legendary tarpon inn resort on useppa island—an ambitious project by none other than barron g. Collier—this historic cottage has journeyed through time. In 1948, it found its forever home atop a majestic dune on captiva island’s prestigious gold coast, relocated by famed philanthropist and big-game hunter col. Francis t. Colby. With 131 feet of unspoiled gulf frontage, the high ridge setting is as rare as it is stunning. Today, the story continues with the addition of a newly built, exquisitely designed guest house—a modern architectural marvel crafted by benchmark construction and visionary - acclaimed architect and designer joyce owens of ajo architecture & designs. This waterfront retreat features two thoughtfully designed guest areas, offering privacy, comfort, and a seamless blend of indoor-outdoor living. Every inch of this estate, from the historic main cottage to the contemporary guest residence, is infused with luxury, elegance, and intention. Together, they create the ultimate gulf-front retreat—a legacy property meant to be treasured for generations. This is more than a home. It's a timeless experience, a rare blend of old-world charm and modern sophistication. A truly unmatched offering on florida’s west coast—impossible to replicate, unforgettable to experience.
Royal Shell Real Estate, Inc.

Captiva, FL Snapshot

120Active Inventory
0New Listings
$149.9K to $23MPrice Range
3Pending Sales
$3.3MMedian Closed Price
N/ADays On Market
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