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5 Florida Keys Waterfront Homes and Prime Hollywood Land Opportunities

By Awais Manzoor

1 min read

South Florida’s appeal often hinges on how a property meets the day-to-day realities of coastal living, and this quintet captures that spectrum. In the Lower Keys, canal-front homes in Sugarloaf, Ramrod, and Little Torch put boating and outdoor routines first, with substantial frontage, refreshed dockage, screened porches, and a pool setting the pace. Farther north, a 4.75-acre Homestead retreat leans into privacy and self-sufficiency. Hollywood rounds out the mix with C-MU–zoned land poised for reinvention.

16941 Driftwood Lane | $1,395,000

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16941 Driftwood Lane, Sugarloaf Key, FL 33042
cobytaylor
LISTING AGENT:
Coby Taylor

Along the water’s edge in Sugarloaf Shores, this custom CBS residence pairs thoughtful design with everyday ease just 19 minutes from Key West. Set on a clear canal with beautiful water views, it’s built for life on the water, with approximately 80 feet of concrete dockage, davits, and easy access to premier backcountry boating. Indoors, curated finishes center on a standout kitchen appointed with Miele appliances, custom stone, and warm wood accents. A split-bedroom layout supports privacy, while the spa-inspired primary suite offers a quiet reset at day’s end. Practical upgrades—metal roof, plus impact windows and doors—underscore the home’s durability. Outdoors, the spacious 10,050-square-foot lot leaves room for a pool, extending the sense of a true Keys retreat.

Price:
$1,395,000
Size:
1,700 sq ft
Contact:
Coby Taylor, Taylor & Assoc. RE, Inc, 305.509.9928
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27414 Guadaloupe Ln | $1,375,000

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27414 Guadaloupe Ln, Ramrod Key, FL 33042
Expert Realty
LISTING AGENT:
Listing agents: Pamela Stangler & Cole Stangler

Along the water’s edge in Ramrod Key, this beautifully updated 3/2 pool home pairs an oversized, fully fenced lot with lush landscaping and an easygoing outdoor rhythm. A 14×32 heated saltwater pool anchors the setting, complemented by a large screened porch with stairs down to the pool and outdoor living space. Inside, porcelain tile floors and granite surfaces in both the kitchen and bathroom set a clean, modern tone, with upgraded cabinetry throughout. The kitchen is generously scaled with a center island, stainless steel appliances, dedicated dining area, and bonus bar seating, while a laundry room with utility sink and tucked-away washer/dryer keeps everyday tasks discreet. A large private master suite and two additional bedrooms are joined by a spacious guest bath, custom blinds, plantation shutters, and a freshly painted exterior—made for long days on the dock and evenings by the pool.

Price:
$1,375,000
Size:
1,492 sq ft
Contact:
Pamela Stangler & Cole Stangler, Expert Realty LLC, 305.433.1036 , 305.890.6417
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21295 SW 376th Street | $1,350,000

21295 SW 376th St, Homestead, FL 33034
21295 SW 376th Street, Homestead, FL 33034
lesliburkhead
LISTING AGENT:
Lesli Burkhead

Set on 4.75 acres in Homestead, this private retreat balances open, airy interiors with the rhythms of country living. High ceilings and an open layout create an easy flow, complemented by tile floors, blinds, and ceiling fans throughout. The spacious kitchen is designed for daily use and entertaining, with an eat-at island, stainless steel appliances—including microwave, stove, refrigerator, and dishwasher—and a dedicated pantry. Nearby, the family room extends outdoors through French doors, connecting seamlessly to a covered patio for relaxed gatherings. A serene primary suite features dual sinks and a tub/shower, while a flex room/office adds welcome versatility. Outside, tropical fruit trees, a pond, and an old chicken coop lend a lived-in rural charm, supported by whole-home water filtration, a propane fireplace, and a generator with tank, plus an as-is detached 2-car garage and carport.

Price:
$1,350,000
Size:
3,291 sq ft
Contact:
Lesli Burkhead, Keyes, 305.282.9603
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0 N 61th Ave | $1,350,000

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0 N 61th Ave, Hollywood, FL 33024
denicelandaeta
LISTING AGENT:
Denice Landaeta

In the heart of Hollywood, Florida, this prime land offering presents a rare chance to shape what comes next. Zoned C-MU (Central Mixed Use), the site is positioned between Sheridan Street and Taft Boulevard, a setting that supports both commercial and residential possibilities. Daily logistics feel easy here, with excellent access to major roads and local amenities, and the Florida Turnpike close at hand for smooth connections across the region. The location also places you near familiar destinations including the Seminole Casino and Walmart, adding to the area’s built-in energy and convenience. With its strategic placement and broad development potential, this lot invites a thoughtful vision—one that can grow alongside Hollywood’s evolving rhythm.

Size: 0.9 acre

Price:
$1,350,000
Contact:
Denice Landaeta, Dluxuss, 954.914.6339
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28560 Doubloon Rd | $1,335,000

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28560 Doubloon Rd., Little Torch Key, FL 33042
Patti Nickless Coldwell Banker Schmitt R. E. C
LISTING AGENT:
Patti Nickless

Along the canal in Little Torch Key, this 3BD/2BA residence pairs easy indoor living with a series of outdoor retreats. Multiple porches extend the living space, including a screened porch that looks directly over the water. Outside, 60 feet of canal frontage sets the tone for days that begin and end at the dock—recently redone with new composite decking for a crisp, low-maintenance finish. An outdoor shower adds a practical, breezy touch after time on the water, while a fenced backyard is framed by tropical landscaping for a sense of privacy and green calm. A garage rounds out the setup, making it simple to balance everyday life with a more relaxed, waterfront rhythm.

Price:
$1,335,000
Size:
1,820 sq ft
Contact:
Patti Nickless, Coldwell Banker Schmitt Real Estate Co., 305.304.6949