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5 Ultra-Luxury Gulf Coast Waterfront Estates in Naples and Beyond

By Awais Manzoor

1 min read

Along Florida’s Gulf Coast, this quintet of trophy coastal estates traces a shared language of resort living—sun, water, and spaces designed to gather. From Aqualane Shores and Port Royal in Naples to Manasota Key, Captiva Island, and Lido Key, each residence emphasizes indoor-outdoor flow, ambitious amenity programs, and a setting where boating, beach days, and sunset views shape the routine. Together, these homes also reveal layered value: new construction and modern systems, walkable lifestyle convenience, and even rare legacy significance on Captiva.

508 16th Avenue S | $12,900,000

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508 16th Avenue S, Naples, FL 34102
Chip Shumway
LISTING AGENT:
Chip Shumway

Along the waterfront streets of Aqualane Shores, this new construction residence pairs preferred southern exposure with a quietly polished sense of arrival. Thoughtfully designed by MHK Architects and constructed by Source Construction and Development, it was recently completed in early 2026 with over 7,000 total square feet of luxury living. The layout includes five bedrooms and seven baths, offering generous flexibility for everyday routines and extended stays. Practicality is equally considered: a 48-kilowatt full-house generator is in place to power all your needs in the event of an interruption. Daily life here can unfold on foot, with a very short stroll to the dining, shopping, and lifestyle hub of Third Street South, and just five short blocks to the sugar sand of Naples’ beaches.

Price:
$12,900,000
Size:
5,593 sq ft
Contact:
Chip Shumway, Gulf Coast International Properties, 239.580.8332
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Incomparable Residence | $11,900,000

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7159 Manasota Key Road, Englewood, FL 34223
mattwyden
LISTING AGENT:
Matt Vander Wyden

Along the water’s edge on Lemon Bay, this gated Mediterranean-inspired estate unfolds across nearly three private acres of resort-style living. Beyond grand gates, a sweeping driveway passes mature oaks, tranquil ponds, waterfalls, and curated sculptures before arriving at a dramatic porte cochère and soaring two-story foyer with stained-glass transoms and a glass elevator. Inside, coffered and tray ceilings, stately columns, extensive millwork, marble and travertine floors, and eight fireplaces create a richly detailed backdrop for daily life. Six ensuite bedrooms are joined by a library with wet bar, a media/family room with projector, and dedicated fitness and meditation rooms. The chef’s kitchen pairs dual islands with Sub-Zero and Wolf appliances, wine fridge, ice maker, and walk-in pantry. Outdoors, enjoy a 30×50 resurfaced saltwater pool and spa, outdoor kitchen, bocce and volleyball courts, a putting green, private dock with boat lift, deeded Gulf beach access, and rooftop terraces for sunset and Gulf views.

Price:
$11,900,000
Size:
12,789 sq ft
Contact:
Matt Vander Wyden, William Raveis, 941.483.0977
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15735 Captiva Drive | $11,900,000

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15735 Captiva Drive, Captiva Island, FL 33924
Valerie Tutor Kingfisher Real Estate Inc
LISTING AGENT:
Valerie Tutor

Along the water’s edge on Captiva Island, this estate spans from beachside to bayside, set between the glistening waters of the Gulf and the captivating Bay. Meticulous renovations and upgrades are felt throughout the main residence, where airy living spaces frame breathtaking panoramic views and invite both sunrises and sunsets into daily life. Shell stone floors, soaring ceilings, custom designs, exquisite finishes, and advanced technology underscore a calm, considered sense of luxury, supported by a whole-home generator and refined amenities. Indoor and outdoor entertaining areas connect seamlessly through pocketing sliders, creating an easy rhythm from interior to terrace. Outside, an expansive setting unfolds around a sparkling pool and spa, designed with grace and sophistication. Adding a rare historic note, a boathouse where Teddy Roosevelt stayed in 1917—on the Historic Register—has been curated as an updated guest cottage with timeless character and stunning bay views.

Price:
$11,900,000
Size:
6,313 sq ft
Contact:
Valerie Tutor, Kingfisher Real Estate, 239.834.8141
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Resort-Style Living In Coastal Masterpiece | $9,750,000

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2560 Half Moon Walk, Naples, FL 34102
jerrydengel
LISTING AGENT:
Jerry D. Engel

Along the water’s edge in Port Royal, this refined estate is designed for luminous, indoor-outdoor living just moments from the sands of Naples and the Port Royal Beach Club. Banks of French doors and expansive casement windows draw in natural light and frame views of meticulously manicured grounds. Outdoors, the setting is tailored to hosting: a pool with elevated spa, a fully equipped summer kitchen, and an intimate gas fireplace for evenings under the stars. Inside, the plan balances gathering and retreat, from a chef’s kitchen with top-tier appliances flowing to the family room and expansive lanai, to a stately dining room and sophisticated living room anchored by a marble-carved fireplace. A dedicated study with custom cabinetry and rich hardwood flooring completes the primary suite, while en-suite guest quarters include a poolside cabana suite overlooking the water. A climate-controlled walk-in wine cellar rounds out the experience.

Price:
$9,750,000
Size:
5,172 sq ft
Contact:
Jerry D. Engel, Independent Brokers Realty, 239.821.9508
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Luxurious Lido Dreams | Contact for pricing

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551 S Washington Drive, Sarasota, FL 34236
tinaellis
LISTING AGENT:
Tina Ellis

Along the water’s edge on Lido Key, Lido Dreams is a brand-new luxury retreat in the vibrant heart of St. Armands Circle. Designed for effortless hosting and privacy alike, the residence offers nine spacious en-suite bedrooms, an elevator, and expansive outdoor living areas that extend the day well beyond the interiors. A private pool and relaxing hot tub set the tone for unhurried afternoons, while an oversized garage with space for up to five vehicles adds welcome flexibility for parking and storage. From the owner’s suite, water views frame the everyday theater of playful manatees and dolphins. Just steps from shopping, dining, and the pristine Lido Key beach, the setting pairs resort-style ease with a walkable island lifestyle, making each arrival feel like a getaway.

Price: Contact for pricing

Size:
5,493 sq ft
Contact:
Tina Ellis, Compass, 512.550.1117