Pearl City Homes with Pool

Pearl City Homes with Pool

Welcome to Pearl City, a hidden gem nestled in the heart of Monroe County, Florida. This charming subdivision offers a unique blend of tranquility and vibrant community living, making it an ideal choice for families, retirees, and anyone in search of a serene lifestyle. With its lush landscapes and friendly atmosphere, Pearl City is more than just a place to live; it’s a place to thrive.

One of the standout features of Pearl City is its stunning homes, many of which come complete with private pools. Imagine stepping out into your backyard oasis, where you can relax by the water, host summer barbecues, or enjoy a refreshing dip on a warm Florida day. These homes are designed for both comfort and enjoyment, showcasing spacious layouts, modern amenities, and beautiful outdoor spaces that beckon you to unwind.

The community is conveniently located near a variety of attractions, including beautiful beaches, parks, and local shops. Whether you’re looking to explore the natural beauty of the Florida Keys or indulge in the vibrant local culture, Pearl City offers the perfect balance of relaxation and adventure.

In addition, the friendly neighbors and community events foster a sense of belonging, making it easy to meet new friends and create lasting memories. If you’re seeking a home that combines luxury, comfort, and a welcoming environment, Pearl City is the perfect place to call home. Discover your dream home with a pool in this idyllic subdivision and experience the best of Florida living!

Newest Pearl City Homes with Pool

$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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