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Poolside Paradise or Waterfront Retreat? Key West Homes for Every Lifestyle

September 4, 2025 by Dominique Barrera Leave a Comment

Do you prefer a pool view, waterfront, or both?

5601 College Rd. A201 – Sunset Marina

Prestigious gated condo w/spectacular Gulf & marina views. Rare 2BR/2BA corner unit, 1,558 sq. ft. open living, granite kitchen, custom walk-in closet, oversized deck. Resort-style pool, hot tub, clubhouse, covered parking + storage.

$1,595,000. Key West Luxury Finders

Cory Held, Jeffrey Grosky, Rikki Shea

305-240-0355

 

20 Aster Terrace

Canal Front Home – Minutes from Key West

Fully upgraded 2BR/1BA with open water views & deep-water access. Renovated with new plumbing, electrical, impact windows/doors, custom cabinetry & porcelain finishes. Brand-new 60′ seawall. Low insurances

$1,375000. Key West Sisters

Angela McChesney 305-395-2540

Jenny Perry 305-747-0369

 

34 Key Haven Road, Canal Front

Beautifully renovated 4BR/2BA with 2 living areas, modern kitchen, and master suite with walk-in closet. Glass doors open to a spacious covered patio overlooking the clean canal. Features include new retaining wall, metal roof, accordion shutters & low insurance rates.

$1,695,000. Key West Sisters

Angela McChesney 305-395-2540

Jenny Perry 305-747-0369

 

3608 & 3612 Sunrise Drive

Key West Waterfront. Rare opportunity to own over 20,000 sq. ft. of canal frontage. Two homes sold together: one 3BR/2BA with pool & fire pit, the other 3BR/3BA with pool, outdoor kitchen & 24K lb. boat lift. Perfect for a family compound or one grand estate.

$5,800,000. Key West Sisters

Angela McChesney 305-395-2540

Jenny Perry 305-747-0369

 

115 Front Street #101, Truman Annex

Harbour Place, sleek 3BR/3BA condo blending historic charm with modern design. Soaring ceilings, smart home tech, quartz chef’s kitchen with Miele appliances, spa-style baths & custom closets. Fully furnished turnkey with covered parking & transient license through year-end.

$2,350,000. Key West Luxury Finders

Cory Held, Jeffrey Grosky, Rikki Shea

305-240-0355

 

1100 South Street, Casa Marina

Ernest Hemingway’s 1928–1929 winter retreat where he wrote A Farewell to Arms. Spacious 3BR/2BA main house with tall ceilings, working fireplace, open living/dining, and modern kitchen. Tropical yard with heated pool & water feature plus charming 1/1 guesthouse with separate entrance. Corner lot with ample parking.

$2,895,000. Key West Luxury Finders

Cory Held, Jeffrey Grosky, Rikki Shea

305-240-0355

Filed Under: Key West Real Estate Tagged With: Casa Marina homes, Ernest Hemingway Key West house for sale, Key Haven Real Estate, Key West homes for sale, Key West luxury properties, Key West pool homes, Key West waterfront real estate, Sunset Marina condos, Truman Annex condos

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Preferred Properties Key West

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Key West

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