Pearl City Homes with Ocean Front Waterfront

Pearl City Homes with Ocean Front Waterfront

Welcome to Pearl City, a hidden gem nestled in the picturesque Monroe County of Florida, where the sun kisses the ocean and the gentle waves serenade your senses. This charming subdivision is renowned for its stunning oceanfront properties, offering a unique blend of coastal living and vibrant community spirit.

Imagine waking up each morning to the sound of the surf and the sight of the sun rising over the horizon, painting the sky in hues of orange and pink. Pearl City is home to a collection of exquisite homes that boast direct access to pristine beaches, perfect for those who appreciate the beauty of waterfront living. With the ocean as your backyard, you'll enjoy a lifestyle filled with outdoor adventures, from kayaking and paddleboarding to fishing and beachcombing.

The homes in Pearl City are designed to embrace the coastal lifestyle, featuring spacious layouts, modern amenities, and breathtaking views that create an inviting atmosphere for families and individuals alike. Whether you’re looking for a cozy beach cottage or a luxurious oceanfront estate, Pearl City has something to suit every taste.

Beyond the stunning residences, this vibrant community offers a variety of local shops, delightful dining options, and recreational activities that cater to all ages. With its friendly atmosphere and stunning natural surroundings, Pearl City is not just a place to live; it’s a place to thrive.

Discover the charm of Pearl City today, where every day feels like a vacation and the ocean is just a stone's throw away! Your dream home awaits in this coastal paradise.

Newest Pearl City Homes with Ocean Front Waterfront

$15,000,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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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