Islamorada, FL Homes for Sale with Pool

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  $525,000

  • 2 Beds
  • 1.5 Baths
  • 794 Sq Ft

  88500 Overseas Hwy Unit 108, Tavernier, FL 33070

  autifully Updated Bayfront Condo in Summer Sea 108 – Tavernier, FLEnjoy relaxed Florida Keys living in this beautifully remodeled 2-bedroom, 1.5-bath first-floor corner unit located in the sought-after Summer Sea Condominium community in Tavernier. Just steps from the marina and Florida Bay, this private-entry residence offers a peaceful setting with a blend of coastal charm and modern

  88500 Overseas Hwy Unit 108, Tavernier, FL 33070
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  $18,999,000

  $501K PRICE DROP

  • 6 Beds
  • 6 Baths
  • 6,054 Sq Ft

  87429 Old Hwy, Islamorada, FL 33036

  A private sanctuary of coastal sophistication, The Oasis offers two residences spanning 2.85 meticulously landscaped acres with over 400 feet of pristine waterfront and a protected deepwater basin. Designed for elevated living, The Oasis blends resort-style amenities with the privacy and scale of a true Florida Keys compound. The grand porte-cochère entry sets the tone, leading to a single-level

  Michaela Walters Ocean Sothebys Intl Realty

  87429 Old Hwy, Islamorada, FL 33036
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  $1,849,000

  $400K PRICE DROP

  • 4 Beds
  • 2 Baths

  150 Azalea St, Tavernier, FL 33070

  Beautiful Double Waterfront Lot in Prestigious Plantation Key Colony. This stunning 4-bedroom, 2-bath waterfront home sits on a Rare Double Lot with a Private Boat Ramp & Boat lift. Step outside to your Private Oasis complete with a Private Tiki hut - Gorgeous secluded in-ground Pool and Cabana Hut Bungalow - The open-concept kitchen features Granite countertops and stainless-steel appliances,

  Tracey Petrusha LoKation

  150 Azalea St, Tavernier, FL 33070
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  $699,000

  • 1 Bed
  • 1 Bath
  • 550 Sq Ft

  81801 Overseas Hwy Unit 729, Islamorada, FL 33036

  Welcome to the iconic Cheeca Lodge & Spa Resort--a rare opportunity to own a premier, income-producing property in the heart of Islamorada. This beautifully appointed one king-bedded room with kitchen, private screened in balcony, with owners closet, offers the ideal blend of personal retreat and investment potential.Set within one of the Florida Keys' most celebrated resorts, owners and

  Ana Zalesky, P.A. Shoreline Properties

  81801 Overseas Hwy Unit 729, Islamorada, FL 33036
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  $649,000

  • 1 Bed
  • 1 Bath
  • 550 Sq Ft

  81801 Old Hwy Unit 754, Islamorada, FL 33036

  Crystal-clear turquoise waters, swaying palms, and gentle ocean breezes create the perfect Florida Keys escape. The historic Cheeca Lodge is located in the heart of Islamorada, which is recognized as ''The Sport Fishing Capital of the World''. Islamorada is renowned for fine dining, water sports, The Art District, galleries, shopping and breweries. The resort encompasses 27 acres with 1,200' of

  81801 Old Hwy Unit 754, Islamorada, FL 33036
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  $3,875,000

  • 4 Beds
  • 3 Baths
  • 3,088 Sq Ft

  109 Giardino Dr, Islamorada, FL 33036

  Coastal elegance meets the ultimate boating lifestyle in this beautifully updated Venetian Shores home. Designed for effortless Keys living, the open floor plan is filled with natural light, highlighted by a dramatic floor-to-ceiling wall of windows in the living area that brings the outdoors in. An inviting entrance foyer welcomes you inside, with interior stairs to the main living level. The

  Alina Davis Coldwell Banker Schmitt Islamorada

  109 Giardino Dr, Islamorada, FL 33036
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  $3,800,000

  New Construction

  • 4 Beds
  • 4.5 Baths
  • 2,574 Sq Ft

  82779 Old Hwy Unit 15, Islamorada, FL 33036

  The Villas at the Islands of Islamorada is a meticulously designed, private gated community now offering fee-simple waterfront single family residences. Every comfort considered and exuding coastal living with stunning ocean views. Four bedrooms, four and one-half bathrooms three-floor villa offers 2,574 sq ft of interior plus 1,169 sq ft patios. Contemporary island architecture with an open,

  The Florida Keys Sold Sisters Ocean Sotheby's International Realty

  82779 Old Hwy Unit 15, Islamorada, FL 33036
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  $665,000

  $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,079 Sq Ft

  118 Cortez Dr Unit B, Islamorada, FL 33036

  This island resort unit offers stations for dockage up to 25-foot boats daytime only, trailer storage and boat ramp. There is a pool for the development, pickle ball and tennis courts. The unit has hurricane impact windows as well as updated balcony area. It offers a large garage area with plenty of storage space. Injoy island living in the Keys .

  Ralph Pena Pena Realty, Inc.

  118 Cortez Dr Unit B, Islamorada, FL 33036
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  $1,199,990

  • 2 Beds
  • 2.5 Baths
  • 1,376 Sq Ft

  111 Anglers Way, Islamorada, FL 33036

  Your dream getaway in the heart of the Florida Keys! This light-filled, spacious 2br/2bth home is located in the highly sought-after Angler's Reef community in Islamorada. Fully furnished, tastefully decorated and turnkey, this well-maintained property is perfect for ocean lovers or savvy investors alike.With over 12 years in a successful vacation rental program and an active vacation rental

  Rosana Velilla Serrano & Associates Real Estate, LLC

  111 Anglers Way, Islamorada, FL 33036
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  $10,900,000

  • 6 Beds
  • 4.5 Baths
  • 4,394 Sq Ft

  186 & 165 Bayview Dr, Lower Matecumbe, FL 33036

  A refined expression of waterfront living, this six-bedroom, four-bath residence is set on a desirable over 1⁄2 acre lot with panoramic water views from every room. Offering 220+ linear feet of concrete dockage with three boat lifts, the property is exceptionally suited for large vessels with effortless access to the open Florida Bay/Gulf or Ocean via Channel 5 bridge. Two separate parcels

  The Florida Keys Sold Sisters Ocean Sotheby's International Realty

  186 & 165 Bayview Dr, Lower Matecumbe, FL 33036
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  /50

  $443,000

  $17K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,100 Sq Ft

  87465 Old Hwy Unit 215, Islamorada, FL 33036

  WELCOME TO PARADISE BY THE SEA! THIS SPACIOUS CONDO LOCATED IN HIGHLY DESIRED PLANTATION KEY/SLAMORADA ON MILLIONAIRE'S ROW. THIS OCEANFRONT BUILDING OFFERS THE PERFECT BLEND OF COMFORT & CONVENIENCE, THIS BEAUTY FEATURES AN OPEN CONCEPT LIVING AREA THAT LIGHT AND BRIGHT! WELL APPOINTED KITCHEN WITH WOOD CABINETS, & FIRST FLOOR HALF BATHROOM. WALK UPSTAIRS TO A COZY SPLIT BEDROOM FLOOR PLAN FOR

  Anthony Garcia The Keyes Company

  87465 Old Hwy Unit 215, Islamorada, FL 33036
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  $5,850,000

  • 5 Beds
  • 4 Baths
  • 2,688 Sq Ft

  233 Aberdeen Ct, Tavernier, FL 33070

  Completely transformed down to the studs and scheduled for completion in late 2026, this extraordinary bay front estate represents the pinnacle of modern Florida Keys luxury. Meticulously rebuilt with elevated design, superior craftsmanship, and today’s most coveted finishes, every detail has been thoughtfully curated to deliver an unparalleled waterfront lifestyle. Experience the ultimate

  Alessondra Figueiras The Keyes Company

  233 Aberdeen Ct, Tavernier, FL 33070

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