Homes with Pools for Sale in Islamorada, FL

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ABOUT THIS HOME
Home with a Pool for sale in Islamorada, FL:
Nestled on a generous half-acre lot in one of Plantation Key's most sought-after neighborhoods, this stunning 3-bedroom, 2.5-bath home with a dedicated office offers the perfect blend of comfort, style, and island living. Boasting 2,117 sq ft of interior space, this property also includes a small guest quarters—ideal for extended family or visiting friends. Step inside to discover a bright, open-concept layout with tasteful finishes and an easy flow from the living room to the dining area and kitchen. The dedicated office provides the flexibility to work from home in peace, while the spacious primary suite offers a private sanctuary complete with an en-suite bath. Step outside and you

$1,479,000

3 beds2.5 baths2,117 sq ft

145 Plantation Blvd, Islamorada, FL 33036

Half-acre lot • Cozy fire pit • Small guest quarters

ABOUT THIS HOME
Home with a Pool for sale in Islamorada, FL:
Experience refined coastal living at Tarpon Flats, Islamorada's most exclusive bayfront enclave. This intimate, gated community consists of just 12 luxury residences spread across four beautifully landscaped acres. A stately paver driveway welcomes you to impeccably manicured grounds, where the charm of Old Florida meets the timeless elegance of Nantucket. This three-story home offers a thoughtful layout and spectacular bay views throughout. The ground floor features covered parking, a versatile multi-purpose room, and access through a gracious foyer entry. Upstairs, the main living level boasts an open-concept kitchen and dining area with panoramic bay vistas, two bedrooms, two bathrooms,

$2,850,000

3 beds3 baths2,072 sq ft

81250 Overseas Hwy #2, Islamorada, FL 33036

Gated community • Covered parking • Paver driveway

NEW CONSTRUCTION

ABOUT THIS HOME
Home with a Pool for sale in Islamorada, FL:
This new construction 4-bedroom, 4-bathroom waterfront residence doesn't just check all the boxes — it redefines them. Spanning 2,476 square feet, this home seamlessly blends modern design with exquisite craftsmanship, complete with top-tier amenities. At the heart of the home is a gourmet chef's kitchen featuring handcrafted fine Italian cabinetry, top-of-the-line appliances, and stunning custom finishes that flow into every room — from the bathrooms to the doors, closets, and beyond. Designed for entertaining, this home boasts an illuminated 165-bottle wine cellar, a Sonos surround sound system indoors and out, and expansive balcony overlooking the canal. Step outside into you

$2,799,999

4 beds4 baths2,476 sq ft

121 Lake Rd, Tavernier, FL 33070

Expansive balcony • Private oasis • Waterfront residence

3D & VIDEO TOUR

ABOUT THIS HOME
Home with a Pool for sale in Islamorada, FL:
Nestled in the Safety Harbor enclave, Islamorada, this stunning Gulfside estate offers unparalleled blend of luxury and tranquility. Situated on a prime point w/ open water and protected dockage, makes this a boater's paradise. With concrete seawall/2 boat lifts this home is appointed for waterfront living. Easy ocean access through Channel 5. Home features 8 ensuite BRs plus 2 half BAs. The master layout, a private sanctuary w/ spa bath, showcases water views thru impact windows/sliding doors. Elevator ensures access to all levels; balconies invite you to savor unobstructed panoramas. The gourmet kitchen w/ high-end appliances/gas cooktop is a chef's delight. With its seamless indoor-outdo

$8,950,000

8 beds9 baths5,392 sq ft

162 Bayview Dr, Islamorada, FL 33036

Protected dockage • Concrete seawall • Water views

(305) 667-4815

ABOUT THIS HOME
Home with a Pool for sale in Islamorada, FL:
Fishermen paradise! . Private Beach . Bay front property . 2 Bedroom apartment in mint conditions. 2 Pools . Game rooms . Community activities . Ramp for small boats ( Kayas, paddleboards) . Gym . 2 parking spots . Party rooms with full kitchen . BBQ and fish preparation area. Fully furnished or un-furnished. Concrete block construction.

$439,000

2 beds1.5 baths794 sq ft

88500 Overseas Hwy #301, Tavernier, FL 33070

Ramp for small boats • Private beach • 2 pools

(305) 924-5915

Property at 171 Kahiki Dr, Tavernier, FL 33070, 3 beds, 3 baths

$5,499,000

3 beds3 baths2,876 sq ft

171 Kahiki Dr, Tavernier, FL 33070

Property at 112 Leoni Dr, Islamorada, FL 33036, 4 beds, 4 baths

$2,950,000

4 beds4 baths2,478 sq ft

112 Leoni Dr, Islamorada, FL 33036

Property at 80151 Overseas Hwy, Islamorada, FL 33036, 2 beds, 2 baths

$3,499,000

2 beds2 baths1,578 sq ft

80151 Overseas Hwy, Islamorada, FL 33036

Property at 75851 Overseas Hwy, Islamorada, FL 33036, 5 beds, 6.5 baths

$5,950,000

5 beds6.5 baths3,978 sq ft

75851 Overseas Hwy, Islamorada, FL 33036

Property at 154 Sebring Dr, Tavernier, FL 33070, 3 beds, 2.5 baths

$900,000

3 beds2.5 baths1,667 sq ft

154 Sebring Dr, Tavernier, FL 33070

(888) 668-8283

Property at 82762 Overseas Hwy #3, Islamorada, FL 33036, 4 beds, 4 baths

$1,999,999

4 beds4 baths2,728 sq ft

82762 Overseas Hwy #3, Islamorada, FL 33036

Property at 125 S Rolling Hill Rd, Tavernier, FL 33070, 2 beds, 2 baths

$774,999

2 beds2 baths1,120 sq ft

125 S Rolling Hill Rd, Tavernier, FL 33070

Property at Undisclosed address, Islamorada, FL 33036, 3 beds, 3 baths

$1,699,000

3 beds3 baths1,680 sq ft

Undisclosed address, Islamorada, FL 33036

(305) 451-4078

Property at 84745 Old Hwy #7, Islamorada, FL 33036, 3 beds, 3 baths

$1,499,000

3 beds3 baths1,680 sq ft

84745 Old Hwy #7, Islamorada, FL 33036

(305) 451-4078

Property at 84745 Old Hwy #13, Islamorada, FL 33036, 3 beds, 3 baths

$1,599,000

3 beds3 baths1,680 sq ft

84745 Old Hwy #13, Islamorada, FL 33036

(305) 451-4078

Property at 135 Tequesta St, Tavernier, FL 33070, 2 beds, 2 baths

$1,299,000

2 beds2 baths1,148 sq ft

135 Tequesta St, Tavernier, FL 33070

Property at 159 Iroquois Dr, Islamorada, FL 33036, 3 beds, 3 baths

$1,990,000

3 beds3 baths2,150 sq ft

159 Iroquois Dr, Islamorada, FL 33036

Property at 189 Gulfview Dr, Islamorada, FL 33036, 3 beds, 2 baths

$2,599,000

3 beds2 baths2,010 sq ft

189 Gulfview Dr, Islamorada, FL 33036

(305) 595-6804

Property at 75931 Overseas Hwy, Islamorada, FL 33036, 5 beds, 5.5 baths

$8,400,000

5 beds5.5 baths4,770 sq ft

75931 Overseas Hwy, Islamorada, FL 33036

Property at 79901 Overseas Hwy #403, Islamorada, FL 33036, 2 beds, 2 baths

$679,000

2 beds2 baths981 sq ft

79901 Overseas Hwy #403, Islamorada, FL 33036

Property at 102 Anglers Way, Islamorada, FL 33036, 2 beds, 2.5 baths

$1,150,000

2 beds2.5 baths1,376 sq ft

102 Anglers Way, Islamorada, FL 33036

Property at 145 Venetian Dr, Islamorada, FL 33036, 4 beds, 3.5 baths

$3,499,000

4 beds3.5 baths— sq ft

145 Venetian Dr, Islamorada, FL 33036

(305) 664-4444

Property at 230 Biscayne Blvd, Islamorada, FL 33036, 5 beds, 3 baths

$3,575,000

5 beds3 baths2,425 sq ft

230 Biscayne Blvd, Islamorada, FL 33036

Property at 282 S Coconut Palm Blvd, Tavernier, FL 33070, 3 beds, 3 baths

$1,725,000

3 beds3 baths2,100 sq ft

282 S Coconut Palm Blvd, Tavernier, FL 33070

Property at 165 Bayview Dr, Islamorada, FL 33036, 6 beds, 4 baths

$8,999,000

6 beds4 baths4,394 sq ft

165 Bayview Dr, Islamorada, FL 33036

Property at 415 Palm Dr, Islamorada, FL 33036, 4 beds, 2 baths

$2,995,000

4 beds2 baths2,928 sq ft

415 Palm Dr, Islamorada, FL 33036

Property at Undisclosed address, Tavernier, FL 33070, 3 beds, 3.5 baths

$2,998,000

3 beds3.5 baths2,938 sq ft

Undisclosed address, Tavernier, FL 33070

(305) 454-2272

Property at 163 Paradise Way Plan, Islamorada, FL 33036, 2 beds, 2 baths

$505,000

2 beds2 baths1,230 sq ft

163 Paradise Way Plan, Islamorada, FL 33036

Listing provided by Zillow

Property at 88041 Old Hwy, Islamorada, FL 33036, 6 beds, 8 baths

$42,000,000

6 beds8 baths9,843 sq ft

88041 Old Hwy, Islamorada, FL 33036

Property at 88181 Old Hwy Unit 3F, Islamorada, FL 33036, 2 beds, 2 baths

$1,239,000

2 beds2 baths1,330 sq ft

88181 Old Hwy Unit 3F, Islamorada, FL 33036

Property at 186 Bayview Dr, Islamorada, FL 33036, 6 beds, 4 baths

$12,900,000

6 beds4 baths4,394 sq ft

186 Bayview Dr, Islamorada, FL 33036

(305) 743-5181

Property at 87851 Old Hwy Unit M35, Islamorada, FL 33036, 2 beds, 2 baths

$1,295,000

2 beds2 baths1,736 sq ft

87851 Old Hwy Unit M35, Islamorada, FL 33036

Property at 82768 Overseas Hwy, Islamorada, FL 33036, 7 beds, 9.5 baths

$25,000,000

7 beds9.5 baths6,935 sq ft

82768 Overseas Hwy, Islamorada, FL 33036

Property at 87200 Overseas Hwy Unit O8, Islamorada, FL 33036, 2 beds, 2.5 baths

$690,999

2 beds2.5 baths1,365 sq ft

87200 Overseas Hwy Unit O8, Islamorada, FL 33036

Property at 170 Sapodilla Dr, Islamorada, FL 33036, 4 beds, 3.5 baths

$10,900,000

4 beds3.5 baths4,512 sq ft

170 Sapodilla Dr, Islamorada, FL 33036

Property at 87465 Old Hwy #102, Islamorada, FL 33036, 2 beds, 2 baths

$428,000

2 beds2 baths1,100 sq ft

87465 Old Hwy #102, Islamorada, FL 33036

(305) 247-7221

Property at 200 Wrenn St #404, Tavernier, FL 33070, 2 beds, 2 baths

$425,000

2 beds2 baths1,179 sq ft

200 Wrenn St #404, Tavernier, FL 33070

Property at 83407 Old Hwy, Islamorada, FL 33036, 6 beds, 5 baths

$6,750,000

6 beds5 baths4,566 sq ft

83407 Old Hwy, Islamorada, FL 33036

Property at 88181 Old Hwy Unit 21H, Islamorada, FL 33036, 2 beds, 2 baths

$935,000

2 beds2 baths1,672 sq ft

88181 Old Hwy Unit 21H, Islamorada, FL 33036

Property at 177 Iroquois St, Tavernier, FL 33070, 3 beds, 2 baths

$925,000

3 beds2 baths1,120 sq ft

177 Iroquois St, Tavernier, FL 33070

Property at 88500 Overseas Hwy #422, Tavernier, FL 33070, 2 beds, 1.5 baths

$649,000

2 beds1.5 baths794 sq ft

88500 Overseas Hwy #422, Tavernier, FL 33070

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Based on information submitted to the MLS GRID as of Mon Dec 01 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Homes with Pools for Sale in Islamorada

There are currently 246 homes with pools for sale in Islamorada at a median listing price of $1.65M. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Islamorada stay on the market for 161 days. This map is refreshed with the newest listings in Islamorada every 15 minutes.

In the past month, 14 homes have been sold in Islamorada. In addition to houses in Islamorada, there were also 41 condos, 12 townhouses, and 3 multi-family units for sale in Islamorada last month. Find your dream home in Islamorada using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Islamorada are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Islamorada. Our Islamorada real estate stats and trends will give you more information about home buying and selling trends in Islamorada. If you're looking to sell your home in the Islamorada area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Islamorada with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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