5 Ultra-Luxury Florida Estates from Pinecrest to Islamorada

Within the prestigious, guard-gated Eagle Trace community in Coral Springs, this legacy estate unfolds across a sprawling 2.38-acre lot, designed for grand-scale living and privacy in South Florida. Inside, approximately 21,302 square feet of expansive living areas includes 9 grand bedrooms—each with a dedicated en suite bathroom—and 18 bathrooms total. Resort-style amenities are woven into the daily rhythm, from a 3,200-square-foot pool and separate detached pool house to a sauna and steam room, regulation-size tennis court, pickleball court, and an indoor racquetball court. For nights in, there’s a private movie theatre, wine/cigar lounge, and a massive upstairs playroom, alongside a dedicated gym and private elevator. Built with CBS construction throughout, a reinforced second floor of concrete and steel, and a commercial-grade 2000-amp electrical supply, the home offers a rare foundation for customization and entertaining.

Along the water’s edge in Islamorada, 139 Gimpy Gulch unfolds behind private gates and mature tropical landscaping, with more than 250 feet of sandy bayfront shoreline devoted to privacy, boating, and sunsets. The compound is arranged as a main home with ground level living, a tri-level guest home, and a large garage/media house, each carrying classic island character and a flexible, retreat-like rhythm. Outdoors, a resort-style pool and spa anchor multiple lounging areas, an outdoor kitchen with covered bar, shady terraces, and intimate gathering spaces. Inside, both residences feature chef kitchens with high-end appliances, including SubZero and La Cornue. A new dock provides immediate access to the bay and ocean, while an included neighboring lot adds boat ramp access. With furnishings, linens, and an array of water and leisure gear included, days here can start on the dock and end on the terrace.

A study in contemporary design, this custom-built new construction residence in North Pinecrest was designed by award-winning architect and designer Thomas Diverio and has been featured nationally in Florida Design magazine. Arrival unfolds past a striking façade and lush landscaping, with a water feature leading into a great room defined by 18-foot ceilings and custom millwork. The open-concept gourmet kitchen is outfitted with Subzero/Wolf appliances, custom cabinetry, and an island, while the expansive living room adds a walk-in wine cellar and floor-to-ceiling windows that draw in natural light. The primary suite pairs a luxurious bath with a custom walk-in closet and a private outdoor spa. A dedicated office, soundproof theater, and spa round out the interiors. Outside, covered patios frame a full outdoor kitchen, covered dining, an infinity pool, and a brand-new pickleball court, all wrapped in privacy. A three-car garage includes a dedicated music studio, attic, and storage room, while a detached guest house offers two bedrooms and baths for visitors.

Set on an expansive 1.78-acre estate in Pinecrest, this retreat balances rare scale with privacy and resort-style ease. Front and back entrance driveways arrive at a grand outdoor oasis, anchored by a newly renovated, heated pool and spa. Beyond, a multi-million dollar landscaping composition unfolds with more than 30 oak trees, exotic mangoes, plush zoysia grass, and stone paths that trace a rolling hill toward a romantic fire pit, gently lit by landscape lighting. The experience culminates in the property’s crown jewel: a Greek-style outdoor theatre designed for unforgettable evenings. Inside, soaring ceilings meet practical luxury— a private elevator, dedicated office, two laundry rooms, and a vast primary suite with a private sitting area overlooking the vista. A chef’s kitchen features Sub-Zero, Wolf, Viking, and Bosch, while an air-conditioned extra-deep 3-car garage flexes as gym or entertainment space. Days here feel quietly cinematic.

Size: Approx. 7,017 sf

Within the serene, guard-gated enclave of Hammock Lakes in Coral Gables, this recently rebuilt contemporary residence has been masterfully enhanced by renowned architect and builder John Roberts Forbes. Thoughtful upgrades support both comfort and modern efficiency, from a house Sonos sound system and Brilliant smart lighting to Unifi WiFi extenders and Ring security. Indoors, a wood-burning fireplace brings warmth and ease, while daily rituals feel elevated with a Kohler soaking tub with heater and a Mr. Steam steam bath. Entertaining is equally considered: a state-of-the-art kitchen pairs Wolf and Sub-Zero appliances with a wet bar for effortless hosting. Outside, a saltwater pool is framed by lush landscaping, with a large backyard and fire pit that extend evenings well past sunset—quiet, private, and designed to be enjoyed.