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Welcome to an extraordinary lifestyle. A private island paradise off Florida's sunset coast. Little Bokeelia Island is 100+ acres of romantic splendor offering majestic tropical living. From the Spanish-style estate home with a private guest wing to the old Florida village just a short stroll away, you are sure to be overcome with a sense of peace and serenity the moment you step off your boat. Whether your desire is to spend the days swimming, walking the nature trail, sunning on the beach, or playing tennis, you are sure to find your own magic amid the tropical tranquility. Your insurance policy is the value created by the current owners' foresight in putting in place the utilities necessary to develop 29 large waterfront lots. Or if history is your motivator, then you will be taken aback with the long, storied past of the island's original residents and visitors including the Calusa Indians, Charles Burgess and Thomas Edison. It's rare, it's unique, it's simply magical.
#201217876

BOKEELIA

1 Little Bokeelia Island

4 Beds

4 Baths

6,486 Sq.Ft.

$24,500,000

MLS#: 201217876

Outstanding opportunity to purchase a one of a kind custom home on nearly 1 acre in prestigious Port Royal! This exquisite estate has 135 feet of water frontage and accommodates a 95 foot dock. The 5 bedroom 4 1/2 bathroom residence is thoughtfully designed and well laid out providing effortless flow from the interior living area to the expansive outdoor living space complete with outdoor kitchen, living area, and fire pit. The chefs kitchen features top-of-the-line appliances oversized island and gas cooktop. Residence has Port Royal club eligibility and it's just a short distance to 3rd Street South's and 5th Avenue South's fine dining, world class shopping, entertainment, and Naples' world famous white sand beaches.
#222010499

NAPLES

885 ADMIRALTY PARADE

5 Beds

4 Baths

5,886 Sq.Ft.

$24,000,000

MLS#: 222010499

Welcome to this move-in ready estate that sits directly on the beaches of exclusive Jupiter Island. A true turnkey luxury retreat that offers immediate peace of mind. This beautiful 5 bed, 7.5 bath home enjoys a 16' elevation, is located on 1.52 acres with 136 feet of private beachfront. The newer (2007) home is 7,597 square feet and perfectly situated for those seeking the idyllic lifestyle.  Designed by renowned architect, Thomas Kirchhoff the home has a private island, richly appointed aesthetic, with high ceilings and Brazilian walnut floors throughout.  The first floor has floor to ceiling French doors with an expansive living room having breathtaking ocean views, a custom office with beautiful cypress walls and built-ins, two dining rooms a guest bedroom and private bath.

A separate family room is perfect for those indoor gatherings, overlooking the picturesque pool and private gardens.  The ultimate chef's kitchen features a Wolf oven, twin Subzeros, two dishwashers, an oversized island and butler pantry, ideal for entertaining.  Additional full and half baths, full laundry room, study nook, hidden wet bar and elevator completes the thoughtfully designed first floor. 
 
Take the private elevator or two separate winding staircases to the second floor with four additional bedrooms, five bathrooms and three large terraces with choice of pool/garden or magnificent ocean views.  The large, private primary suite has vaulted ceilings, his and her custom closets and his and her luxury baths.  There are French doors leading to an oversized balcony to enjoy unobstructed ocean views or to simply feel those evening ocean breezes.  There are three additional bedrooms on the second floor and expansive terraces.   Additional laundry and storage for ideal convenience, complete the second floor.  The home has been meticulously maintained, with a brand new roof (October 2024) and whole house generator (February 2025) and includes an oversized 3-car attached garage.
 
The outdoor beauty of this home is ideal for al fresco dining, from the private gated courtyard with gardens and custom swimming pool and waterfall, to the multiple covered loggias and outdoor kitchen.

Truly an unparalleled opportunity to own a fully furnished beachfront sanctuary!
#224100216

JUPITER

475 South Beach RD

5 Beds

7 Baths

7,597 Sq.Ft.

$24,000,000

MLS#: 224100216

Poised on the shimmering waters of Smugglers Bay in prestigious Port Royal, this Stofft Cooney–designed West Indies-style estate is a rare jewel in today’s luxury market. Developed and sold by the esteemed VIV Homes in 2021, the residence offers nearly 8,000 square feet of impeccably maintained living space, featuring 5 bedrooms plus a dedicated study. The home feels virtually brand new and is located just moments from the exclusive Port Royal Beach Club on Fort Charles Drive. Showcasing an unrivaled fusion of craftsmanship, design, and panoramic views, every detail of this residence reflects quality and sophistication. Highlights include full concrete construction, Legno Bastone wide-plank wood flooring, dual gourmet and service kitchens with bespoke cabinetry and Cristallo Prime countertops, a built-in wine wall, and premium finishes throughout. The expansive open-concept layout seamlessly connects interior and exterior living, perfect for entertaining. The outdoor space is a true retreat, complete with a resort-style pool and spa with sun shelf, a fireplace, waterside fire pit, fully remastered landscape in 2025, and automated roll-down screens and shutters. Substantial fixed and floating dockage accommodates lift access, power, water, and seating—ideal for boating enthusiasts. This extraordinary property offers immediate Port Royal Club eligibility and represents a flawless blend of luxury, location, and lifestyle. Every element has been meticulously considered to deliver a living experience of the highest caliber.
#225038835

NAPLES

3525 Fort Charles DR

5 Beds

6 Baths

7,706 Sq.Ft.

$23,995,000

MLS#: 225038835

H.13538 - Beyond the gated entry, sits this stately and elegant home overlooking the Gulf of Mexico, boasting over 7000 Sq Ft of luxurious living area. Mature lush landscaping imparts a sense of tropical solitude and privacy in this beachfront setting with 166 feet of Gulf beach frontage. This exquisite beachfront residence was designed by esteemed architect Andrea Clark Brown and built and finished to the most exacting standards by A. Vernon Allen Builders with an elegant and refined quality all its own. An impeccable home, in an incomparable beachfront location, in the prestigious Port Royal neighborhood.
#218059080

NAPLES

3430 Gordon DR

6 Beds

6 Baths

7,002 Sq.Ft.

$23,900,000

MLS#: 218059080

Sold in one day
#224027693

NAPLES

900 Spyglass lane

5 Beds

5 Baths

7,600 Sq.Ft.

$23,900,000

MLS#: 224027693

This Gulf-front masterpiece offers an unparalleled blend of location, luxury, and resort-style living. The home has experienced no water intrusion in living areas during recent weather events. The residence combines historic charm with sophisticated elegance. The home underwent an extensive three-year renovation and reconstruction, completed in 2024 with Kukk Architecture. Now practically new, the residence preserves its heritage, grandfathered footprint, and distinctive character while offering modern luxury throughout. The 6,100-square-foot, fully air-conditioned living space maximizes its premier beachfront setting. The well-designed layout offers five spacious bedrooms, five full and two half baths, a private study, and a flexible sixth bedroom. Sweeping Gulf views provide a stunning backdrop. The gourmet kitchen boasts dual Cristallo quartzite islands, top-tier appliances, custom cabinetry, and a service kitchen. Additional features include a private gated entry, two fireplaces, elevator, whole-house generator, automated screens/shutters, water filtration, and ultra-efficient air conditioning. Perfectly positioned on the Gulf, just moments from the dining and boutique shopping of Third Street South and Fifth Avenue South. A rare opportunity in the heart of Old Naples.
#225071400

NAPLES

55 13th AVE S

6 Beds

5 Baths

6,143 Sq.Ft.

$22,995,000

MLS#: 225071400

TROPHY RESORT-ISLAND BAYFRONT ASSET. FULLY STABILIZED. PRIME ENTERTAINMENT DISTRICT LOCATION!
Old Seaport Place is the crown jewel of Fort Myers Beach — a rare, fully stabilized, triple-net-leased waterfront investment positioned at the epicenter of the island’s billion-dollar reinvention. Situated on 1.80 irreplaceable bayfront acres in the heart of the Old San Carlos entertainment district, this institutional-grade asset delivers reliable income today with exceptional upside tomorrow. This listing includes a total of 6 parcels, anchored by three of the island’s most iconic waterfront restaurants — Nervous Nellie’s, Snug Harbor, and Wahoo Willie’s — the property features long-term NNN leases with seasoned operators who have deep roots in the community and proven performance post-Hurricane Ian. These are not speculative tenants. They are dominant market leaders generating predictable, escalating income with percentage rent participation — all while the landlord remains insulated from operating expenses. Old Seaport Place is more than a restaurant collection. It is a revenue platform. The asset includes over 25,000 square feet of income-producing improvements, 21 deep-water marina slips, and a 122-space private parking lot — a critical competitive advantage on Fort Myers Beach. Both marina and parking components are independently monetizable and provide immediate value-add potential. The parking field alone presents a compelling development opportunity. With strong demand and favorable zoning, a multi-level garage with rooftop activation or event space could dramatically enhance revenue while reinforcing the property’s position as the island’s entertainment nucleus. The surrounding corridor is experiencing unprecedented capital infusion. Margaritaville Resort has elevated hospitality demand. The $200M Arches Bayfront marina village is rising directly adjacent. Major resort redevelopments and luxury condo projects are underway across the island. Tourism has surpassed pre-Ian levels, with record visitation and sustained growth in ADR and occupancy. Old Seaport Place sits directly in the path of this momentum. From a capital markets perspective, the asset delivers a compelling 7.56% in-place cap rate on 2025 NOI — outperforming comparable Florida waterfront restaurant districts that have traded in the 4.5%–6.5% range — while offering diversified income across dining, marina, and parking revenue streams.
With stabilized cash flow, hard coastal real estate, hurricane-tested operations, and multiple avenues for expansion, this is a fortress asset positioned for long-term appreciation and strong exit optionality. Opportunities of this scale and location rarely come to market. Old Seaport Place is not just a secure investment — it is control of the waterfront at the center of Fort Myers Beach’s resurgence.
#226010179

FORT MYERS BEACH

645 OLD SAN CARLOS BLVD

None Beds

None Baths

N/A

$22,900,000

MLS#: 226010179

Sensational vistas overlooking Naples Bay and the entrance to the southern waterways beyond! Graciously situated on resplendent grounds with approximately 145 feet of water frontage per the plat and/or deed on one of the most desirable streets in Port Royal - Nelson’s Walk. Built in 2016 to exacting standards by The Williams Group, Inc., the home incorporates luxurious modern amenities, indoors and outdoors. Striking in its attention to detail, the immaculately maintained home features stunning light-filled rooms and an extremely well conceived configuration. Particular attention was paid to great room spaces as well as cozy and private retreats. The first floor accommodations include the primary suite with separate his and her bathrooms and closets, a guest suite, great room, kitchen, large butler’s pantry, den, and an office. The two upstairs guest suites each feature ensuite baths and each is also accompanied by an additional “bunk room.” Oversized 3 bay garage. The large pool deck and covered outdoor living area enjoy some of the very finest views in all of Naples! Port Royal Club Membership eligibility.
#221059765

NAPLES

1070 Nelsons WALK

4 Beds

4 Baths

5,780 Sq.Ft.

$22,900,000

MLS#: 221059765

As the featured cover story in Florida Home and Design magazine...Sweeping water vistas and contemporary interiors are a sublime match at this superb modern property.  This stunning estate completed in 2017,  and designed by Stofft Cooney is set on nearly 1.5 acres.  The home is crafted from the finest materials featuring, Italian white-oak floors, Bamboo veined limestone, marine grade stainless steel, and Egyptian Grey hammered natural stone. Vast sliding glass walls disappear for seamless indoor-outdoor living, leading to large lanais, outdoor kitchen, a firepit, and a 77 ft. glass-tiled pool. The expansive grounds also encompass a natural beach and oversized four-car garage.  Owners are eligible to join the exclusive Port Royal private beach club complete with spa, tennis facilities, beachfront dining, and a fitness center.
#219002892

NAPLES

1777 Galleon DR

5 Beds

5 Baths

10,400 Sq.Ft.

$22,900,000

MLS#: 219002892

Presenting a rare and incredible opportunity to build your dream home on this beautiful interior beachfront lot in the heart of Old Naples. This exclusive .47-acre property has 114 feet of beach frontage on the Gulf of Mexico, with striking postcard views of the Naples pier. Enter the unique interior location by a private drive off of Gulf Shore Boulevard, which offers tremendous privacy from the public beach access. Located a few short blocks from shopping and dining on Fifth Avenue and Third Street with proximity to all that Naples has to offer. The existing Rutenberg El Dorado home sustained damage to the residential structure and the property is being sold "as is" for the lot value and any demolition, permitting, repairs, etc. will be the responsibility of the purchaser. Do not walk on the property without permission.
#222088205

NAPLES

1050 Gulf Shore S BLVD

4 Beds

4 Baths

3,314 Sq.Ft.

$22,500,000

MLS#: 222088205

Enjoy breathtaking panoramic water views from one of the most desirable Port Royal properties available in 40 years! With a lot-and-a-half at .89 Acres, this private and serene estate encompasses nearly an acre of waterfront property with 151’ of deep water-frontage on Naples Bay.  Property is a boaters dream with direct access to the Gulf of Mexico just minutes away. Resplendent lanai views showcase picturesque mangroves framed by the expansive water of Naples Bay. Discover luxurious living in Port Royal, one of the most beautiful and verdant communities in Southwest Florida.  The current residence has been meticulously maintained and consist of four bedrooms plus den with a separate study/office and is ready for your finishing touches while you design and build your dream home.  You will marvel at the quiet serenity offered by this lovely Galleon Drive site ideally located a short bike ride from the beach and is just minutes from 3rd Street South, and 5th Avenue South’s fine dining, world-class shopping, and entertainment. Port Royal Club membership eligibility.
#221062785

NAPLES

1857 Galleon DR

4 Beds

3 Baths

5,073 Sq.Ft.

$22,500,000

MLS#: 221062785

H.10490 - This exquisite Southern-Colonial estate sits on an iconic Gordon Drive site comprising 2.53 acres, approximately 150 feet of wide sandy beachfront and offers captivating Gulf of Mexico vistas.  The main house includes 3 bedrooms + study and sprawls across 6,209 Sq.ft. of living area with timeless style and casual elegance.  From the minute you enter this estate through the magnificent central hallway you will be entranced by the Gulf views and beautiful floating wood staircase.  Features include wood and marble flooring, fan windows, intricately carved marble and stone gas fireplaces, beautiful custom millwork and much more.  The expansive master suite boasts a marble and stone gas fireplace, large sitting area, 30’ x 36’ balcony, large Walk-in-Closet and beautiful Calcutta marble floored master bath.  One can sit back and enjoy the sparkling Gulf of Mexico waters from the 94-foot terrace or balcony upstairs.  Property includes two guest houses near the front of the estate site.  Eligible for membership to the exclusive Port Royal Club.
#216066804

NAPLES

2440 Gordon DR

3 Beds

3 Baths

6,209 Sq.Ft.

$22,500,000

MLS#: 216066804

Immaculate, nearly new custom home, built in 2020, w/ 111’ of water frontage & western exposure in exclusive Port Royal, w/easy access to the Gulf of Mexico. Designed by Kukk Architecture & built by A. Vernon Allen Builders, this resort-worthy, 2-story home features well-crafted interior finishes, 5 full-bedrooms w/en-suite baths (includes 2nd flr VIP suite & laundry), a full pool bath & 2 half baths, elevator, dining room, club room & den/6th bedroom w/walk-in closet. Numerous upgrades can be found throughout including Control 4 Audio/Video system, Lutron shades in 9 rooms, steam shower in master, security system & whole house audio system. The chef-grade kitchen features high-end cabinetry, huge butler’s pantry & top-of-the-line appliances: 60” Wolf range, 72” Subzero Ref/freezer, Wolf steam oven, icemaker, 2 Subzero wine coolers. The stunning, outdoor pool complex includes a spa, outdoor kitchen & bar, & built-in fire pit/lounge. Other boaters will envy the properties Bellingham 48' concrete floating dock with 7×12 landing, 33,000lb super lift & 2nd 7,000lb beamless lift. Residence is finished with a five-car garage w/cabinets & slat-wall system. Port Royal Club eligibility.
#223008764

NAPLES

3320 RUM ROW

5 Beds

5 Baths

7,100 Sq.Ft.

$22,500,000

MLS#: 223008764

Recently completed, fully furnished, and perfectly positioned on Old Harbour channel. This impeccably appointed residence represents a special opportunity in todays market.  Masterfully constructed by Viv Homes and penned by Stofft Cooney Architects, the home is West Indies inspired, seamlessly blending transitional finishes highlighted by wide plank wood flooring, grays, whites and touches of color.  5 en suite bedrooms, study, and loft, and offering over 6,500 square feet of air conditioned space with 4 car garage. A serene outdoor living area provides vistas of the waterway and lush green preserve to the south. Preferably located on western exposure, it’s a short walk to the Port Royal Club and pristine beach. A direct Port Royal membership opportunity that is unrivaled.
#221083113

NAPLES

3300 Fort Charles DR

5 Beds

6 Baths

6,532 Sq.Ft.

$22,495,000

MLS#: 221083113

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