Private Island in the Florida Keys With Helipad and Solar Power Lists For $16 Million

Positioned just off the coast of Marathon, East Sister Rock Island is a rare private sanctuary wrapped in vibrant turquoise waters—accessible by boat or via a private, on-island helipad has hit the market for $16 million.

A once in a generation opportunity to own a legacy property, the island spans approximately 6.5 total acres—including 5.8 acres of private surrounding seabed– offering an extraordinary aquatic playground for snorkeling, swimming, kayaking, paddleboarding, fishing, and exploring the pristine waters of the Florida Keys.

At the island's heart is an updated 3-bedroom, 2-bath main residence alongside a separate guest house, offering over 5,000 square feet of refined living space. The interior highlights a chef-inspired kitchen adorned with premium countertops and contemporary finishes, while a 12-foot-wide wraparound veranda delivers sweeping, panoramic ocean vistas, breathtaking Atlantic sunrises, and iconic Keys sunsets.

Resort-style outdoor living features a waterfront pool and spa, lush tropical landscaping, dedicated alfresco lounging and dining venues, helipad, and a 100-foot deep-water dock accommodating multiple vessels.

Engineered to be eco-friendly and fully self-sufficient, East Sister Rock is powered by solar and wind systems with battery storage, a backup generator, a desalination system, and ample freshwater cistern capacity. The offering includes 99 E Ocean Drive on the mainland which includes private dock space.

1 East Sister Rock Island in Marathon, Florida Keys is listed for $16 million by Vladimir Rochebrun & Aaron Rosenthal with The Chad Carroll Group at Compass.

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Constellation Group and Ironwood Venture Group Complete Seaglass Cove In The Florida Keys

Constellation Group and Ironwood Venture Group have completed SeaGlass Cove, a 14-residence oceanfront community in Marathon, and the closing of an $8.46 million permanent loan from Centennial Bank. The financing replaces the project’s construction loan and marks SeaGlass Cove’s transition from development to a fully completed, move-in-ready residential community. With seven residences sold and seven remaining, the project is now 50% sold.

Set along the Atlantic Ocean, SeaGlass Cove features 14 three-story residences offering more than 4,800 square feet of indoor-outdoor living space with sweeping water views. Four- and five-bedroom floor plans include expansive great rooms, chef’s kitchens, spa-inspired bathrooms, generous owner and guest suites, private cabanas, covered terraces and two-car garages. Thoughtfully landscaped grounds connect the residences to a private white-sand beach, resort-style pool and community pickleball court.

Seven move-in-ready residences remain available for sale, including four turnkey furnished homes, one of which was professionally designed by award-winning luxury interior design firm Interiors by Steven G. Prices begin at $3 million.

The furnished residences allow buyers to begin enjoying the community immediately, while the ability to rent on a weekly basis provides additional flexibility for owners when they are not in residence.

“Now that SeaGlass Cove is complete, buyers and brokers can experience the full ‘barefoot-luxury’ vision firsthand—from the architecture, interiors and landscaping to the beach and waterfront amenities,” said Eduardo Otaola, Managing Principal of Constellation Group. “The response from those touring the finished community has been exceptional. With half of the residences sold, several turnkey homes available and the flexibility of weekly rentals, SeaGlass Cove offers a rare combination of immediate enjoyment, elevated design and ownership flexibility in the Florida Keys.”

The $8.46 million permanent financing from Centennial Bank closed following completion of construction and replaced the project’s construction financing. The transaction reflects SeaGlass Cove’s progression from active development to a completed residential community and provides a long-term financing structure as the project enters its next phase of sales and operations.

“SeaGlass Cove is a distinctive, well-executed development supported by experienced sponsors and the continued strength of the luxury residential market in the Florida Keys,” said David Druey, Regional President of Centennial Bank. “We are pleased to provide permanent financing and support Constellation Group as the completed community enters its next chapter.”

The residences pair Stone International cabinetry and KitchenAid appliances with spacious, functional layouts designed for effortless indoor-outdoor living. Expansive great rooms open to covered terraces, while private cabanas and outdoor living areas overlook the water. The architecture, interiors, landscaping and material palette have been carefully coordinated to create a cohesive resort-residential experience throughout the community.Located in the heart of the Florida Keys, residents enjoy access to a private white-sand beach, resort-style pool, pickleball court and a wide range of nearby boating, fishing, paddleboarding, snorkeling and other water activities.

SeaGlass Cove is located near Hawks Cay Resort and Marina, Coffins Patch Reef—known for its coral formations and lobstering—and The Lagoon, a popular destination for wakeboarding and other water-based recreation. Nearby marinas, restaurants, shops and natural beaches further enhance the relaxed, waterfront Florida Keys lifestyle.SeaGlass Cove is approximately 20 minutes south of Islamorada and offers convenient access to the Florida Keys/Marathon International Airport and the Overseas Highway, connecting residents to destinations throughout the entire Florida Keys.

SeaGlass Cove is located at 59720 Overseas Highway, Marathon, FL 33050.

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Mast Capital And Koch Real Estate Investments Acquire The Islands of Islamorada Resort In The Florida Keys, Set To Launch Sales of Private Waterfront Villas

Mast Capital, in partnership with Koch Real Estate Investments, has acquired The Islands of Islamorada Resort, a luxury resort in Islamorada, Florida, offering convenient access to the Florida Keys’ renowned boating, fishing, dining and outdoor recreation destinations.

The joint venture of Mast Capital and Koch Real Estate Investments acquired the resort from the seller Frisbie Group. Berkadia Miami’s Scott Wadler arranged acquisition financing through lender Ardent Real Estate. It was reported in July 2024 that Wills Company had acquired the property for $72 million but Frisbie Group retained a stake in the partnership.

Located at 82779 Old Highway in the Upper Keys, just 90 minutes from Miami, The Islands of Islamorada Resort features 22 private, oceanside villas and eight hotel suites across a serene and exclusive enclave. The luxury resort offers direct water access and an elevated hospitality experience in one of the Florida Keys' most sought-after destinations.

Spanning approximately seven acres of exceptional shoreline property in Islamorada, known as the "Sport Fishing Capital of the World," the resort offers an array of upscale amenities, including two oceanfront swimming pools, a private beach, two pickleball courts, two playgrounds, a beachfront bar and a state-of-the-art fitness center. Guests also enjoy access to a private marina with boat slips, paddleboards, kayaks and sailboats for leisurely coastal pursuits, as well as personalized concierge services and event spaces for weddings, corporate retreats and other special occasions.

The new ownership group plans to re-launch sales and marketing efforts for the property's 22 waterfront villas, with Ocean Sotheby's International Realty serving as the exclusive sales broker. With prices starting at $3.8 million, the fully furnished, detached residences span 4,067 total square feet and feature four bedrooms, four full bathrooms, three-story layouts with covered waterfront loggias primed for outdoor entertaining, two-car garages with EV charging capabilities, premium finishes and appliances, integrated smart-home technology, and concrete block construction built to current hurricane code standards.

"The Florida Keys represent one of the country's most supply-constrained hospitality markets, where exceptional waterfront assets continue to benefit from strong long-term demand and high barriers to entry," said Jordan Kornberg, Chief Investment Officer of Mast Capital. "The Islands of Islamorada offers villa buyers a unique opportunity to own a newly built, high-quality residence in the heart of the Florida Keys with the lifestyle of a luxury resort and ability to generate income through the resort’s rental program."

“The financing reflects continued lender confidence in well-capitalized sponsors pursuing differentiated and high-barrier investments in supply-constrained markets like the Florida Keys," Wadler said. "The Islands of Islamorada offered a rare combination of an irreplaceable waterfront location, luxury condo-hotel product and an experienced ownership group with a clear business plan, allowing the financing to come together on an accelerated timeline."

The acquisition further expands Mast Capital's growing hospitality portfolio across Florida as it continues to invest in premier leisure and lifestyle destinations. The firm's hospitality holdings include the three Michelin-key destination Little Palm Island Resort & Spa in the Florida Keys, one of the state's most exclusive luxury island retreats and America’s only private island resort, accessible only by sea or sky. The firm also owns the iconic Saddlebrook Resort in Tampa Bay, a 480-acre property that recently relaunched following a transformative renovation.

In addition to its hospitality assets, Mast Capital is also currently advancing several high-profile residential projects, including The Perigon Miami Beach, an ultra-luxury oceanfront condominium developed alongside Starwood Capital Group; Cipriani Residences Miami, an 80-story luxury residential tower that recently topped off in Brickell; and Banyan Tree Residences West Palm Beach, Banyan Group’s first-ever residential project in the U.S. being developed in collaboration with Curated JCZM Development.

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The Wills Companies Acquires The Islands of Islamorada In The Florida Keys For $72 Million

The Wills Companies, a reputable real estate development firm, has recently completed the acquisition of The Islands of Islamorada luxury resort in Islamorada, Florida, from The Frisbie Group of Palm Beach. The transaction, which amounted to $72 million, was financed by City National Bank of Florida with strategic guidance and underwriting provided by Metropolis Capital Advisors.

“The Frisbie Group has created a truly special destination in Islamorada, and we are committed to continuing that legacy of excellence,” said Tim Wills of The Wills Companies. “The Islands of Islamorada presents an infinite array of opportunities for future homeowners. Imagine owning a piece of paradise, steps from the beach, with all the amenities of a world-class resort at your fingertips. It’s truly an unparalleled lifestyle.”

The Islands of Islamorada, a newly built resort in the Upper Keys, consists of 22 waterfront villas and an oceanfront eight-unit suite hotel. The Wills Companies, in partnership with Urgo Hotels, Indigo Hotel Group LLC, Badlands Hotel Capital, Dolben Company, and other prominent investors, intends to maintain the existing five-star luxury resort while introducing the 22 waterfront villas as luxury residential units available for purchase for the first time. Each residence boasts four bedrooms, full kitchens, and outdoor leisure spaces.

The distinctive ownership model of the resort homes will enable residents to relish a maintenance-free resort lifestyle while also enjoying passive income from the rental operation. Prospective buyers can benefit from significant tax advantages through 1031 exchanges. The gated property offers an array of amenities, including pools, a Tiki Bar, Pickle Ball courts, a private beach, a marina, watersports, and a driving range that launches biodegradable golf balls into the ocean.

Tim Wills of The Wills Companies expressed enthusiasm about continuing the tradition of excellence established by The Frisbie Group at The Islands of Islamorada. He highlighted the remarkable opportunities available for future homeowners, emphasizing the unparalleled lifestyle of owning a piece of paradise with resort amenities at their disposal.

Ocean Sotheby's International Realty, a key partner in the transaction, will oversee the sale of the single-family homes at the resort. With a wealth of experience and market knowledge, Ocean Sotheby's International Realty, led by Russell Post since 2010, played a crucial role in finalizing the deal.

Located in the esteemed Village of Islamorada, the resort is situated in a prime location within the "Sportfishing Capital of the World." Residents will have easy access to an array of outdoor activities, including fishing, diving, snorkeling, and boating, as well as nearby dining establishments, shops, and galleries.

The acquisition of The Islands of Islamorada by The Wills Companies marks a significant development in the real estate landscape of the Florida Keys, offering potential buyers a unique opportunity to own a luxurious waterfront residence with resort-style amenities in a sought-after destination.

Images via 1OAK Studios and Sargent Photography

Check Out This Private Island At Ocean Reef Club Asking $75 Million

Nestled amidst the waters of the Florida Keys sits a rare opportunity, a 26 acre Private Island plus an additional waterfront mainland home within Ocean Reef Club. The private island island features a pool home, 12 one-acre developable waterfront lots, a 20-slip marina capable of accommodating a mega-yacht, three separate apartments, dockmaster office, a white sand beach and two tennis courts which convert to a helipad for a 10 minute flight to Miami. Modern infrastructure including fiber optic cable, water, & electricity, ensures seamless connectivity and convenience. The mainland property within Ocean Reef Club is a four-minute boat ride away and features a 100 ft. dock. The illustrious Ocean Reef Club features a private airport, two championship golf courses, a world-class 175-slip marina, impressive tennis & lawn sports facilities, full-service fitness center, salon and spa, medical center, oceanfront inn, and an array of shopping and fine dining options.

Pumpkin Key, 10 Cannon Point, Key Largo is listed for $75,000,000 with Liz Hogan of Compass.

Images via Legendary Productions

First Luxury Single-Family Residences at SeaGlass Cove in The Florida Keys Set To Be Delivered in March

The first luxury single-family residences at SeaGlass Cove in the Florida Keys are set to be delivered in March 2024. SeaGlass Cove is a new, luxurious island enclave consisting of just 14 single-family homes in Marathon, Fla., in the heart of the Florida Keys. Located at 59720 Overseas Highway in Grassy Key, the project is being developed by Constellation Group, a Miami-based commercial real estate investment and development firm, and Ironwood Venture Group, a Florida-based private equity and full-service real estate development company focused primarily on the Florida Keys. Banesco USA provided the $17 million construction loan to build SeaGlass Cove Residences in early 2023 and the project was over 40% sold at the time of groundbreaking.

“SeaGlass Cove introduces a new dimension in waterfront living in one of Florida’s most sought-after destinations,” said Eduardo Otaola, Principal at Constellation Group. “The initial success of the sales process is a true testament to the demand buyers have for the Florida Keys and our well-conceived private enclave focused on barefoot luxury.”

Nestled amongst colorful coves and turquoise waters in a private gated community, SeaGlass Cove features three-story homes comprised of 4,800+ square feet of living and entertainment space that offer stunning views of the Atlantic Ocean. Residences will feature a two-car garage, chef’s kitchen, and spa baths that will be luxuriously appointed with MiaCucina finishes and Wolf/Subzero appliances (or Stone International finishes and KitchenAid appliances). Additional highlights include a private covered cabana and an optional summer kitchen replete with beach access.

The oceanfront enclave features a myriad of resort-style amenities, including a pool overlooking the ocean, an on-site pickleball court, and activities that include paddleboarding, swimming, fishing, snorkeling, biking, and much more. SeaGlass Cove is minutes from fine dining, shopping, spas, marinas, and much more.

Sea Glass Cove is 20 minutes South of Islamorada, is in close proximity to the Florida Keys/Marathon International Airport, and offers convenient access to Overseas Highway, which spans the entire chain of the Keys, and over the Atlantic Ocean, Florida Bay, and the Gulf of Mexico.

Pacaso Launches Luxury Second Home Co-Ownership Platform In The Florida Keys

Pacaso, the leading real estate platform that helps people buy and co-own a luxury second home, has announced that it has expanded its service to the Florida Keys. The company has begun expanding its regional team in addition to an existing Miami and Fort Lauderdale-based team, and is working with a variety of local businesses to support its operations.

“From breathtaking ocean-side scenery to world-class fishing, rich culture and local cuisine, the Keys have long been a popular getaway destination full of endless island activity,'' said Pacaso CEO and Co-Founder, Austin Allison. “We’re thrilled to be expanding our South Florida presence into the Keys and empowering more second home buyers to own a slice of this coastal haven. Our service helps make more efficient use of available housing stock by creating new inventory, allowing a small group of families to become part of a community as unique as the Florida Keys through co-ownership of a luxury home.”

“Pacaso is leading the charge on fractional ownership, and I’ve witnessed firsthand their success in Miami and Fort Lauderdale and am excited they are expanding their business down to the Florida Keys,” said Josh Dotoli, a founding Compass broker in South Florida and leader of one of the top-producing sales teams in the Southeast Region. “I loved the idea of owning part of a Pacaso home in Islamorada so much that I bought a share myself. The property is a new waterfront home with a pool and access to a private beach just 100 miles from Miami. It's a fun boat trip for my family down to the Keys, and we will be able to pull right up to the dock of our Pacaso. We can't wait to create memories at the house, and we have Pacaso to thank for making this dream of a Keys home a reality for us and many others in the near future.”

Pacaso partners with all interested real estate agents and brokerages in markets where it operates. Real estate agents representing buyers who purchase a share of a Pacaso home receive a 3% referral commission in addition to 500 RSUs of Pacaso stock as a referral equity bonus. Agents in South Florida who are interested in working with Pacaso can learn more on the company’s website.

Pacaso’s first listing in the Keys is a 5-bedroom, 3.5 bathroom coastal-inspired home nestled along a canal in White Marlin Beach. The Islamorada home spans 2,900 SF and features open-concept living spaces with soaring ceilings, oversized windows and glass doors that seamlessly connect the interiors to the pool, swaying palms and waterway beyond. The main floor primary bedroom includes a custom closet and opens to the pool and patio. The main bedroom upstairs has a large closet and a Jack & Jill bath leading to another guest bedroom. With two additional bedrooms, the home easily accommodates family and friends. The home comes fully furnished and professionally decorated.

1/8 ownership of the home is asking $444,000 with the whole home price at $2,790,000.

America's Southernmost Marina Key West Harbour Sells For $39.5 Million

Key West Harbour, the southernmost marina facility in The United States located in Key West, Florida, totaling 13.1 acres, has sold for $39.5 million. Avison Young Principal George Vail represented the seller, iStar Inc. Key West Harbour is located on Stock Island, a transformative tourist enclave in Key West, emerging with luxury hotel, boating, and recreational fishing. George Vail describes the property as a rare high-quality asset that offers strong in-place cash flow and potential for rent increases and redevelopment opportunities. Key West Harbour, located at 6000 Peninsular Ave., Key West, is also Key West’s sole hurricane grade, dry rack storage facility.

“Stock Island has traditionally been known as a commercial fishing destination and is emerging as a tourist, luxury hotel, boating, and recreational fishing mecca,” said Vail. “Key West Harbour is a rare high-quality asset that offers strong in-place cash flow and potential for rent increases and redevelopment opportunities.”

Key West Harbour was completed in 2008 and features 99 wet slips, 375 indoor dry racks, 13 outdoor dry racks, and six workforce and market rental apartment units. The class A hurricane rated marina also offers several amenities including a clubhouse featuring a full-service restaurant and pool, event space for weddings, and a private beach.

“After Hurricane Irma, there was an initial pause with the influx of investments within the Keys,” added Vail. “Economic advantages and geographic anomalies remained, and activity has significantly rebounded.”