Dreaming of investing in paradise or finding your next tropical home? From vibrant Old Town Key West to the peaceful shores of Sugarloaf, these six unique properties offer a range of exceptional opportunities. Whether you’re searching for long-term income, family living, or elegant retreats, these homes deliver.
📍 918–921 Thomas Street — $3,999,000
Lighthouse View Compound – Old Town Investment Gold
A rare opportunity to own the entire four-unit Lighthouse View Condominium Association in the heart of Old Town. This fully rented, income-producing compound features:
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Gated entry, carport, and bricked courtyard
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Main residence with private heated pool, hot tub, and garden terrace
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Detached two-story building with great room, kitchen, half bath + master suite upstairs
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Two charming 1BD/1BA guest cottages with porches and shared outdoor wet bar
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Additional building with 2 x 1BD/1BA units and a glamorous 2BD/1BA upstairs with a private deck
📞 Mabry Binnicker – 305-304-5624
📍 180 Sugarloaf Drive — $775,000
Charming Retreat in Sugarloaf Shores
Tucked away on a spacious 12,000 sq ft lot, this 3BD/2BA home is full of character and potential. Enjoy:
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Remodeled kitchen, cozy screened porch, and bonus outdoor seating
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Room for a pool, boat, or RV
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Fenced yard, lush gardens, and outdoor shower
Perfect for full-time living or weekend escapes. Easy to show!
Contact Key West Sisters
📞 Angela McChesney – 305-395-2540
📞 Jenny Perry – 305-747-0369
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📍 312 William Street — $1,795,000
Tropical Seaport Hideaway
Just steps from the Historic Seaport, this vibrant Conch-style home is full of charm:
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2BD/2BA main house + detached pool house/3rd BD w/ half bath & outdoor shower
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Dade County pine, exposed beams, lime green quartz counters, Wolf range, and luxe appliances
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Saltwater dipping pool, IPE decking, and breezy balconies
True Key West living—bright, bold, and beautiful.
📞 Cory Held, Jeffrey Grosky, Rikki Shea – 305-240-0355
Key West Luxury Finders
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📍 3741 Eagle Avenue — $4,400,000
A Masterpiece of Coastal Design
Built to perfection, this fully furnished 3BD/3.5BA home offers 10.5 ft elevation and unmatched luxury:
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Concrete construction, cathedral ceilings, impact glass, generator
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Upstairs & downstairs primary suites
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Detached guest cottage with views
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Craig Reynolds-designed tropical landscaping, coral rock outdoor shower, heated/chilled pool
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481 SF garage, turnkey
📞 Angela McChesney – 305-395-2540
📞 Jenny Perry – 305-747-0369
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📍 1100 South Street — $2,895,000
Casa Marina Corner Compound with History
A rare, elegant property on a prominent Casa Marina corner lot, with 8,100 sq ft of one-story living:
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3BD/2BA main house + conch-style 1BD/1BA guest house
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Tall ceilings, sliding glass doors, fireplace, seamless indoor-outdoor living
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Heated pool, water feature, and lush landscaping
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Multiple parking areas with dual entrances
📞 Cory Held, Jeffrey Grosky, Rikki Shea – 305-240-0355
Key West Luxury Finders
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📍 37 Evergreen Avenue — $2,500,000
Elegant Waterfront Living in Key Haven
This elevated 3BD/3BA home at the end of a quiet cul-de-sac features:
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Updated kitchen, open floor plan, expansive master suite
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French doors to balconies off every bedroom
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Direct boating access, generator, impact windows, enclosed A/C garage
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Freshly painted interior/exterior
Live the boating lifestyle with style and comfort.
📞 Angela McChesney – 305-395-2540
📞 Jenny Perry – 305-747-0369
Ready to schedule a tour or want more info?
Reach out to the agents listed above or leave a comment below. Whether you’re investing, relocating, or dreaming of island life, these homes are ready to welcome you.
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