Pearl City Homes with Waterfront

Pearl City Homes with Waterfront

Welcome to Pearl City, a hidden gem nestled in the heart of Monroe County, Florida. This charming subdivision boasts an idyllic waterfront lifestyle that beckons both nature lovers and those seeking tranquility. With its picturesque views and serene atmosphere, Pearl City is the perfect place to call home.

Imagine waking up each day to the gentle sounds of lapping water and the soft rustle of palm trees swaying in the breeze. The homes in Pearl City are designed to embrace the stunning waterfront scenery, offering spacious layouts and modern amenities that cater to every lifestyle. From cozy bungalows to luxurious waterfront estates, there’s something for everyone in this vibrant community.

Living in Pearl City means more than just a beautiful home; it’s about embracing a lifestyle rich in outdoor adventures. Residents enjoy easy access to boating, fishing, and kayaking right from their backyards, making it a paradise for water enthusiasts. The nearby parks and nature reserves provide ample opportunities for hiking, bird-watching, and picnicking amidst Florida's natural beauty.

Community spirit thrives in Pearl City, with friendly neighbors and local events that foster connections and camaraderie. Whether you’re looking for a peaceful retreat or an active lifestyle, Pearl City offers the best of both worlds.

Discover the charm of Pearl City and experience waterfront living at its finest. Your dream home awaits in this enchanting subdivision where every day feels like a vacation. Come and explore the possibilities that Pearl City has to offer!

Newest Pearl City Homes with Waterfront

$15,000,000
3 Beds ⋅ 3 Baths ⋅ A12014942 MLS
Set along prestigious Millionaire’s Row in Tavernier, 88835 Old Highway presents a rare waterfront offering spanning over 3 oceanfront acres, plus an additional acre with a protected private boat basin. Blending privacy, expansive land, and future potential, this exceptional property embodies refined coastal living in the Upper Keys. Completed in 2022, the residence features 3 bedrooms, 2 bathrooms, and approximately 1,500 square feet of thoughtfully designed interiors with impact windows and doors, rich hardwood flooring, a steel metal roof, and a designer kitchen outfitted with premium Viking appliances. Outdoor spaces are designed for effortless luxury, featuring shell stone porch flooring, covered parking, lush tropical landscaping, and low-maintenance turf. The estate consists of three separate parcels, including a buildable lot (Lot 1A), the current homesite (Lot 2A), and a natural hammock parcel (Lot 3A) that serves as a permanent privacy buffer, enhancing the property’s exclusivity and tranquility. With direct access to a private boat basin and the rare opportunity to create a custom waterfront compound, 88835 Old Highway offers an unmatched combination of immediate enjoyment, development flexibility, and long-term value in one of the Florida Keys’ most coveted waterfront enclaves.

88835 Old Highway, Tavernier
$27,000,000
5 Beds ⋅ 8 Baths ⋅ A12014955 MLS
Set on over 2 acres along prestigious Millionaire’s Row in Tavernier, this newly constructed oceanfront residence offers an extraordinary blend of scale, design, and modern coastal luxury. Encompassing approximately 8,200 square feet under air and over 16,000 total square feet, the home was thoughtfully designed for elevated living and grand-scale entertaining. The property features 5 bedrooms, 6 full baths, and 2 half baths, with all bedrooms offering en suite accommodations, custom closets, and refined finishes throughout. Additional highlights include a private office, elevator, whole-home sound system, 600-amp electrical service, and five independent AC zones. Interiors are curated with white diamond marble, rich teak wood flooring, custom millwork, and a striking steel roof. The chef’s kitchen is outfitted with premium Wolf, SubZero, and Cove appliances, dual dishwashers, farmhouse sinks, and custom mahogany countertops. With 240 feet of direct ocean frontage, outdoor living is equally impressive, anchored by a 120-foot resort-style pool with heating and chilling systems, a gas-heated spa, summer kitchen, cabana bath, and expansive covered entertaining areas. Additional features include a 3-car garage, climate-controlled workshop, and weekly rental zoning, offering both exceptional lifestyle appeal and investment potential.

88845 Old Highway, Tavernier
$40,000,000
8 Beds ⋅ 11 Baths ⋅ A12015811 MLS
A rare dual-parcel offering on prestigious Millionaire’s Row in Tavernier, 88835 and 88845 Old Highway present an extraordinary opportunity to own one of the Upper Keys’ most expansive and versatile oceanfront compounds. Spanning multiple acres with 480 feet of waterfrontage, the property combines exceptional privacy, premier boating access, and remarkable future development potential. At 88845 Old Highway, a newly constructed 8,200 SF modern estate showcases 5 bedrooms, 6 full baths, 2 half baths, designer finishes, smart-home technology, a resort-style 120-foot pool, and a protected basin with dockage, boat lift, and deep-water access. Complementing the main estate, the adjacent parcel at 88835 Old Highway encompasses over 3 additional acres and introduces a rare layer of flexibility and long-term value. The property includes a renovated 3-bedroom residence completed in 2022, a transferable TDR allowing for the future construction of a substantially larger primary residence, an additional buildable lot, and a lush natural hammock buffer that enhances privacy and exclusivity. Together, this exceptional compound delivers an unmatched blend of luxury living, investment potential, and future flexibility in one of the Florida Keys’ most coveted waterfront settings.

88835/88845 Old Highway, Tavernier
$15,990,000
6 Beds ⋅ 9 Baths ⋅ A11974804 MLS
Newly completed in 2025, this exceptional oceanfront estate is located in the heart of The Florida Keys on the premier ocean side of Islamorada. A gated entry welcomes you through lush tropical landscaping and a diverse fruit-tree grove, setting a private and refined arrival. Set on over 2 usable acres with 210 feet of private sandy beachfront and a protected cove, the residence spans 7,590 square feet of interior living space & 1,736 square feet of exterior living, with an expansive 230-foot dock. Designed for seamless indoor-outdoor living, the home features a dramatic great room with 23-foot ceilings, panoramic Atlantic exposure, and expansive covered terraces with summer kitchen and outdoor dining areas. A 65-foot heated lagoon-style pool with swim-up bar and fire-pit lounge creates a resort-caliber setting. The chef’s kitchen is appointed with Sub-Zero, Wolf, and Thermador appliances. Additional highlights include dual primary suites, private orchid garden, lounge & recreation room, elevator, Sonos surround sound, impact windows and doors, metal roof, double-height garage, water-sports storage room and a full home generator. The essence of beachfront living in Islamorada, combining impressive scale and ultimate privacy. ***A contiguous 0.7-acre lot with development rights for an ancillary building with upstairs storage is available separately.

88351 Old Highway, Islamorada
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