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Dickeys John Houses Sold

Ultra Luxury
Ultra LuxuryAbove $1,000 per SqFt
High-End$650 - $1,000 per SqFt
Mid-Tier$400 - $650 per SqFt
Premium$300 - $400 per SqFt
Entry-LevelBelow $300 per SqFt
Low-Rise
Building with 1- 4 floors
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0–30 favors buyers
30–100 favors sellers
Selling Speed
17
Steady
Shows how quickly homes are being absorbed by buyers
20%+ Fast
8–19.9% Steady
Below 8% Slow
Inventory Supply
5.88
Balanced
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0–3 Low
3–6 Balanced
6+ High
Sales Activity
Updating
Awaiting sufficient data
Shows how often homes are selling in this community
2+/mo Active
0.75–1.99/mo Steady
Below 0.75/mo Quiet
Results 7 of 7
Sold - Jul 23, 2026
Dickeys John, 15735/737 Captiva Dr, Captiva, Florida 33924, image 1
Dickeys John, 15735/737 Captiva Dr, Captiva, Florida 33924, image 2
Dickeys John, 15735/737 Captiva Dr, Captiva, Florida 33924, image 3
$10,000,000 $3M
  • 5 Beds
  • 51/2 Baths
  • 5,751 SqFt
  • $1,739/SqFt
Ultra Luxury
House sold in Dickeys John
15735/737 Captiva Dr, Captiva, FL 33924
Set amidst the glistening waters of the gulf and the captivating bay, this stunning estate epitomizes unparalleled luxury and exclusive waterfront living. Stretching from beachside to bayside, the property offers dazzling sunrises & sunsets, and shows meticulous renovations and upgrades throughout, with no detail overlooked. Every aspect of this magnificent estate has been crafted with the utmost care and precision, ensuring a truly exceptional living experience. The main residence is a stunning blend of elegance and comfort, highlighting airy living spaces and breathtaking panoramic views of the gulf and bay. The home features shell stone floors, custom designs, exquisite finishes, advanced technology, a new whole home generator, elevator to all floors, and refined amenities. The chef's kitchen, equipped with the finest of viking appliances, is sure to inspire culinary creativity. The impressive indoor and outdoor entertaining areas seamlessly connect via pocketing sliders, creating a harmonious flow between spaces. The expansive outdoor area is framed by a sparkling pool and spa, artfully designed with grace and sophistication in mind. From the immaculate garage to the private, luxurious top-floor guest suites, the numerous comfort features elevate and enhance island living. A special aspect of this iconic estate is the historic boathouse where teddy roosevelt stayed in 1917, expertly curated as a charming & updated guest cottage with timeless character, and breathtaking bay views. A kayak launch and copious trex deck extending into the bay and culminating in a new covered boat lift complete the picture of this coastal castle by the sea. Dolphins crossing presents a rare opportunity to own one of the very few properties that encompasses both gulf and bay, offering the ultimate captiva island lifestyle. Truly the best of both worlds, owning a piece of history while enjoying the finest in modern luxury living. This is more than just a home – it is a statement legacy.
Sold - Feb 18, 2026
Dickeys John, 15771 Captiva Dr, Captiva, Florida 33924, image 1
Dickeys John, 15771 Captiva Dr, Captiva, Florida 33924, image 2
$7,500,000 $2M
  • 3 Beds
  • 3 Baths
  • 2,920 SqFt
  • $2,568/SqFt
Ultra Luxury
House sold in Dickeys John
15771 Captiva Dr, Captiva, FL 33924
Far-a way. Long admired as an iconic captiva residence, this exceptional waterfront estate occupies a coveted position along the platinum coast, where timeless island architecture meets refined coastal living. Stretching from the gulf to the bay you can have it all! Resting on a high beach ridge with 10 ft of elevation and expertly landscaped by r.S. Walsh, the grounds feature vivid plantings and exceptional specimen trees sourced from around the globe, along with meandering paths beautifully framing the home. Inside, an expansive great room is framed by a dramatic wall of french doors that capture serene water views and flood the space with natural light. The ceilings are  highlighted by exposed white beams and shiplap detailing create an atmosphere of refined coastal elegance, complemented by solid hardwood oak floors that ground the airy scale of the room. Designed for effortless entertaining, the open layout flows seamlessly to the pool and terrace beyond, blurring the boundaries between indoor and outdoor living. Sculptural wood-blade ceiling fans and crisp architectural millwork complete this exceptional island retreat—where craftsmanship, light, and lifestyle converge in perfect harmony. Chef's will admire the open and large finely appointed kitchen. The guest rooms are located on the main level along with the library, office and utility room. A striking lap pool runs elegantly alongside a covered patio, creating a resort-caliber outdoor experience designed for both relaxation and entertaining. At sunrise and sunset, the setting becomes truly breathtaking. Golden light washes across the residence as sweeping views extend over calm bay waters to the shimmering gulf beyond. A private pier stretches gracefully into the water, inviting boating and sunset cruises, while layered tropical foliage frames the scene with natural elegance. As the sun slips below the horizon, the sky is painted in soft shades of amber, coral, and lavender—gentle coastal breezes stirring the palms and reinforcing the timeless romance of bayfront living paired with spectacular gulf sunsets.
Dickeys John, 15855 Captiva Dr, Captiva, Florida 33924, image 1
Dickeys John, 15855 Captiva Dr, Captiva, Florida 33924, image 2
$8,795,000
  • 4 Beds
  • 31/2 Baths
  • 2,112 SqFt
  • $4,164/SqFt
Ultra Luxury
House for sale in Dickeys John
15855 Captiva Dr, Captiva, FL 33924
This old florida charmer "circa 1910" has gingerbread trim, shaker siding, metal roof and is surrounded by a leafy hammock of mature tropical vegetation. Situated in the exclusive gulf-to-bay stretch of captiva island. Enter this nostalgic, true cracker-style cottage with white wood shutters on the windows, a double french door entry, wood beamed ceilings and wood floors to a cheery, comfortable home filled with years of family memories. Just over an acre, this family compound has it all and brings a lure of living in a tropical climate on the gulf of mexico. The main house features 3 bedrooms, 2.5 baths, living room, family room, dining room, kitchen and an open patio deck that looks over the open, heated pool. There is a separate single car garage with a guest suite above that offers a kitchenette, bedroom and full bath. Take a walk on one of the many paver walkways throughout the property to the "secret garden" and the dock w/lift. Enjoy the private path to the beach!!
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Dickeys John, 15867-15879 Captiva Dr, Captiva, Florida 33924, image 1
Dickeys John, 15867-15879 Captiva Dr, Captiva, Florida 33924, image 2
$11,000,000
  • 6 Beds
  • 6 Baths
  • 5,044 SqFt
  • $2,181/SqFt
Ultra Luxury
House for sale in Dickeys John
15867-15879 Captiva Dr, Captiva, FL 33924
Rare opportunity to own beach to bay on this stretch of captiva island. This beautiful waterfront estate w/deep water boat dock offers nearly 4, 000sq ft of living in the main house and 1, 275 sq ft of living in the charming guest house. You can have it all from sunrise to sunset with panoramic views of the gulf of mexico and pine island sound. The main home offers lots of spacious living, beach, and bay lanai areas, a large pool/spa and covered outdoor entertaining areas, a 3car garage, a deep water dock and lift that can support a luxury yacht and another watercraft of your desire. The home has an upscale yet casual feel and has been recently enhanced with all impact windows and doors, a new tile roof, a beautiful kitchen, and more. The charming guest cottage will take you back in time while offering comfort and serenity. Want to enjoy the best of all worlds, beach to bay on captiva island is the spot. The property includes the main house, & guest house located at 15867 & 15879 captiva drive.
Dickeys John, 15899 Captiva Dr, Captiva, Florida 33924, image 1
Dickeys John, 15899 Captiva Dr, Captiva, Florida 33924, image 2
$6,900,000
  • 4 Beds
  • 3 Baths
  • 2,780 SqFt
  • $2,482/SqFt
Ultra Luxury
House for sale in Dickeys John
15899 Captiva Dr, Captiva, FL 33924
Captiva gulf-front with boat dock! This "paradise found" beach house is checking all of the boxes. Gulf frontage, boat dock with 16, 000-lb lift, large pool and outdoor entertainment area, elevator, whole-house generator system, new impact doors and windows with a 3-car garage. Enjoy unobstructed gulf views from nearly every room. The great room floor plan is perfect for entertaining - the living area radiates with natural light, providing a spectacular, panoramic view of the gulf. The primary suite offers a private sundeck, spacious bath, and separate office. There are two guest en-suites, one offering a terrace with fantastic gulf views, and the other overlooking the pool area. A spacious family room and bonus area are on the lower level. Gulf to bay living at its best! Paradise found, gulf front, with the option to purchase this estate separately or collectively with the bay front "rainbow's end" estate creating the ultimate gulf-to-bay compound and ultimate waterfront experience. See mls#224045415-15891 captiva dr
Dickeys John, 15735/737 Captiva Dr, Captiva, Florida 33924, image 1
Dickeys John, 15735/737 Captiva Dr, Captiva, Florida 33924, image 2
$13,995,000
  • 5 Beds
  • 51/2 Baths
  • 5,751 SqFt
  • $2,433/SqFt
Ultra Luxury
House for sale in Dickeys John
15735/737 Captiva Dr, Captiva, FL 33924
Set amidst the glistening waters of the gulf and the captivating bay, this stunning estate epitomizes unparalleled luxury and exclusive waterfront living. Stretching from beachside to bayside, the property offers dazzling sunrises & sunsets, and shows meticulous renovations and upgrades throughout, with no detail overlooked. Every aspect of this magnificent estate has been crafted with the utmost care and precision, ensuring a truly exceptional living experience. The main residence is a stunning blend of elegance and comfort, highlighting airy living spaces and breathtaking panoramic views of the gulf and bay. The home features shell stone floors, custom designs, exquisite finishes, advanced technology and refined amenities. The chef's kitchen, equipped with the finest of viking appliances, is sure to inspire culinary creativity. The impressive indoor and outdoor entertaining areas seamlessly connect, creating a harmonious flow between spaces. The expansive outdoor area is framed by a sparkling pool and spa, artfully designed with grace and sophistication in mind. From the immaculate garage to the luxurious top-floor guest suites, the numerous comfort features elevate and enhance island living. A special aspect of this iconic estate is the historic boathouse where teddy roosevelt stayed in 1917, expertly curated as a charming & updated guest cottage with timeless character, and magnificent bay views. Dolphins crossing presents a rare opportunity to own one of the very few properties that encompasses gulf and bay, offering the ultimate captiva island lifestyle. Truly the best of both worlds, owning a piece of history while enjoying the finest in modern luxury living. This is more than just a home – it is a statement legacy.
Dickeys John, 15891 Captiva Dr, Captiva, Florida 33924, image 1
Dickeys John, 15891 Captiva Dr, Captiva, Florida 33924, image 2
$5,900,000 $650K
  • 5 Beds
  • 41/2 Baths
  • 4,729 SqFt
  • $1,248/SqFt
Ultra Luxury
House for sale in Dickeys John
15891 Captiva Dr, Captiva, FL 33924
Bay front retreat with endless potential on captiva island! Nestled on a prime 3/4 acre bay front parcel, this distinguished residence offers unobstructed vistas of shimmering waters, steps from 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.

Subdivision Amenities

Fishing Pier
None
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Beach Access
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Nearby Subdivisions

Ultra Luxury
0.23 miles
Entry-Level
0.32 miles
High-End
0.62 miles
For Sale (3)
$1.5M - $3.5M
Mid-Tier
0.66 miles
For Sale (3)
$5.7M - $12M
Mid-Tier
1.03 miles
For Sale (3)
$284K - $624K

Schools

Scores

Walk Score®
Car-Dependent. Almost all errands require a car
21

100
Bike Score®
Somewhat Bikeable. Minimal bike infrastructure
30

100
Sound Score®
Bearable noise
78

100
Airport Score
Close to airports. Noticeable airport activity
0

100
Traffic Score
Congested area. Frequent traffic delays
24

100
Local Score
Limited local amenities nearby
0

100

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