Homes with Pools for Sale in Monroe County, FL

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NEW CONSTRUCTION

ABOUT THIS HOME
Home with a Pool for sale in Monroe County, FL:
Zephyr Cove; the extravagant aquatically inspired retreat that you deserve. Located on the breathtaking waterfront nestled along the Gulf and designed and built by D'Asign Source. This stunning estate invites you to experience the perfect balance of luxury, tranquility, and adventure. With both fresh and saltwater elements woven into its design, every detail has been thoughtfully crafted. At the heart of the property lies a lazy river loop infinity pool, complete with bridges, swim-up pool bar in gazebo, spa with table, lap pool, beach-style entries, and waterfall grotto plus gas fire pit, putting green, and tropical gardens. From floating under the sun, entertaining guests, or enjoying a p

$35,000,000

9 beds9.5 baths9,530 sq ft

57223 Morton St, Grassy Key, FL 33050

Swim-up pool bar • Whole-home generator • Ample dockage

ABOUT THIS HOME
Home with a Pool for sale in Monroe County, FL:
IMPROVED: PRICE! SELLERS WILL CONSIDER REASONABLE OFFERS!! DO YOU NEED A THIRD BEDROOM? CONVERTS EASILY TO A 3/2 HOME! Architectural drawings available from the owners for the additional bedroom! Do you like the beach. .. do you like boating? This is it!!! This home is cozy and spacious, and stunning Waterfront Retreat in Sombrero Beach! This extraordinary Florida Keys stilted pool home is perfectly positioned on a prime corner lot minutes from the world-renowned Sombrero Beach. A boater's paradise featuring a 60 ft. dock, 30,000 lb. boat lift, fish cleaning table and a dock tower with 50-amp and 30-amp outlets including a 110-volt outlet. Quick access to open water to world class fis

$1,650,000

2 beds2 baths1,532 sq ft

341 Sombrero Beach Rd, Marathon, FL 33050

60 ft dock • Stilted pool home • 000 lb boat lift

ABOUT THIS HOME
Home with a Pool for sale in Monroe County, FL:
This is a SHORT SALE and is subject to lender approval. Opportunity for you to have an island of Key West lifestyle! Whether a primary home or investment, this condo should be on your list -- great location, multi-level living, and covered deeded parking. Located near the center of the island conveniently located close to shopping plazas, movie theater, schools and dining as well as being just a few minutes from the heart of Old Town Key West. With two bedrooms and two bath, plus a central area half bath, and private patio, this home is an attractive option for any Buyer wanting Key West island living. The condo complex has a large pool for residents' use and the monthly condo fee includes

$392,000

2 beds2.5 baths1,100 sq ft

3314 Northside Dr #46, Key West, FL 33040

Large pool • Multi-level living • Great location

3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in Monroe County, FL:
Turnkey 2BD/2BA Ocean Pointe Condo - Fully Furnished, Short-Term Rentals Allowed! Welcome to paradise! This beautiful 2-bedroom, 2-bathroom condo in the sought-after Ocean Pointe community offers the perfect blend of luxury, convenience, and income potential. With 826 sq ft of thoughtfully designed living space, this fully furnished, turnkey unit is ready for immediate occupancy or short-term rental—invest, vacation, or stay forever! Inside, enjoy impact-resistant windows and doors, stainless steel appliances, a Titan tankless water heater, and a full-size LG washer and dryer. Whether you're sipping coffee on the balcony or heading out for a day on the water, this condo has everything

$479,000

2 beds2 baths826 sq ft

500 Burton Dr #1202, Tavernier, FL 33070

Heated pool and spa • $1,425 HOA • Community pool

ABOUT THIS HOME
Home with a Pool for sale in Monroe County, FL:
Location, Location, Location! A renovation project that will increase the value of your investment exponentially! This home is located between the Southernmost Point and the Hemingway House in the world-renowned City of Key West Florida. Besides the excellent location, this home has concrete fences, a concrete gated entry from Whitehead Street, a nice sized rear deck/patio, front sitting/garden area, side walkways and plenty of room to add your favorite things to the yard spaces. An outside shower finishes off the exterior, a Key West ''must''. The interior has the sought after Dade County Pine on the walls, extremely high ceilings, and a large loft where you can stand up at the center. Th

$765,000

2 beds1 bath1,057 sq ft

1102 Whitehead St, Key West, FL 33040

2,303 sq ft lot • Community pool • Built 1963

Property at 260 Sadowski Cswy, Key Colony Beach, FL 33051, 3 beds, 2 baths

$1,325,000

3 beds2 baths1,540 sq ft

260 Sadowski Cswy, Key Colony Beach, FL 33051

Property at 1405-1409 United St, Key West, FL 33040, 3 beds, 3 baths

$2,790,000

3 beds3 baths1,872 sq ft

1405-1409 United St, Key West, FL 33040

Property at 80201 Overseas Hwy, Islamorada, FL 33036, 5 beds, 5.5 baths

$7,400,000

5 beds5.5 baths4,764 sq ft

80201 Overseas Hwy, Islamorada, FL 33036

Property at 75761 Overseas Hwy, Islamorada, FL 33036, 4 beds, 4 baths

$4,750,000

4 beds4 baths3,001 sq ft

75761 Overseas Hwy, Islamorada, FL 33036

(305) 507-8442

Property at 308 Sabal St, Duck Key, FL 33050, 7 beds, 6 baths

$7,499,000

7 beds6 baths4,000 sq ft

308 Sabal St, Duck Key, FL 33050

Property at 30 Cannon Royal Dr, Key West, FL 33040, 4 beds, 5 baths

$5,750,000

4 beds5 baths5,180 sq ft

30 Cannon Royal Dr, Key West, FL 33040

Property at 1113 Stump Ln, Key West, FL 33040, 4 beds, 4.5 baths

$4,450,000

4 beds4.5 baths2,985 sq ft

1113 Stump Ln, Key West, FL 33040

Property at 862 Cardinal Ln, Key Largo, FL 33037, 4 beds, 4 baths

$1,999,000

4 beds4 baths— sq ft

862 Cardinal Ln, Key Largo, FL 33037

(305) 451-4078

Property at 138 Golf Club Dr, Key West, FL 33040, 2 beds, 1.5 baths

$585,000

2 beds1.5 baths806 sq ft

138 Golf Club Dr, Key West, FL 33040

Property at 239 Lignumvitae Dr, Key Largo, FL 33037, 3 beds, 2 baths

$699,000

3 beds2 baths1,060 sq ft

239 Lignumvitae Dr, Key Largo, FL 33037

Property at 231 E Shore Dr Unit 6, Key West, FL 33040, 5 beds, 5.5 baths

$4,375,000

5 beds5.5 baths4,103 sq ft

231 E Shore Dr Unit 6, Key West, FL 33040

Property at 508 Grinnell St, Key West, FL 33040, 3 beds, 3 baths

$2,595,000

3 beds3 baths2,049 sq ft

508 Grinnell St, Key West, FL 33040

Property at 136 Giardino Dr, Islamorada, FL 33036, 4 beds, 3 baths

$3,250,000

4 beds3 baths3,481 sq ft

136 Giardino Dr, Islamorada, FL 33036

Property at 31473 Warner Rd, Big Pine Key, FL 33043, 3 beds, 4 baths

$2,450,000

3 beds4 baths2,087 sq ft

31473 Warner Rd, Big Pine Key, FL 33043

Property at 2827 Harris Ave, Key West, FL 33040, 5 beds, 5 baths

$1,949,000

5 beds5 baths3,086 sq ft

2827 Harris Ave, Key West, FL 33040

Property at 36 Park Rd, Islamorada, FL 33036, 4 beds, 3 baths

$1,550,000

4 beds3 baths2,277 sq ft

36 Park Rd, Islamorada, FL 33036

Property at 2394 Coco Plum Dr, Marathon, FL 33050, 18 beds, 19.5 baths

$11,000,000

18 beds19.5 baths12,198 sq ft

2394 Coco Plum Dr, Marathon, FL 33050

Property at 3841 N Roosevelt Blvd #632, Key West, FL 33040, 2 beds, 2.5 baths

$749,000

2 beds2.5 baths1,357 sq ft

3841 N Roosevelt Blvd #632, Key West, FL 33040

Property at 184 Bahama Ave, Key Largo, FL 33037, 3 beds, 3 baths

$2,299,000

3 beds3 baths1,870 sq ft

184 Bahama Ave, Key Largo, FL 33037

Property at 802 Bonito Ln, Key Largo, FL 33037, 4 beds, 4 baths

$3,995,000

4 beds4 baths2,669 sq ft

802 Bonito Ln, Key Largo, FL 33037

Property at 6500-6600 Overseas Hwy, Marathon, FL 33050, 6 beds, 10.5 baths

$9,500,000

6 beds10.5 baths10,852 sq ft

6500-6600 Overseas Hwy, Marathon, FL 33050

Property at 59720 Overseas Hwy #7, Marathon, FL 33050, 5 beds, 4.5 baths

$2,975,000

5 beds4.5 baths3,013 sq ft

59720 Overseas Hwy #7, Marathon, FL 33050

Property at 111 Anglers Way, Islamorada, FL 33036, 2 beds, 2.5 baths

$1,199,990

2 beds2.5 baths1,376 sq ft

111 Anglers Way, Islamorada, FL 33036

(305) 521-3290

Property at 115 Front St #101, Key West, FL 33040, 3 beds, 3 baths

$2,249,999

3 beds3 baths1,325 sq ft

115 Front St #101, Key West, FL 33040

Property at 1133 W Ocean Dr #2, Key Colony Beach, FL 33051, 3 beds, 3 baths

$749,000

3 beds3 baths1,929 sq ft

1133 W Ocean Dr #2, Key Colony Beach, FL 33051

Property at 98222 Windward Ave, Key Largo, FL 33037, 2 beds, 2 baths

$475,000

2 beds2 baths778 sq ft

98222 Windward Ave, Key Largo, FL 33037

Property at 231 E Shore Dr Unit 2, Summerland Key, FL 33040, 5 beds, 5.5 baths

$4,250,000

5 beds5.5 baths4,103 sq ft

231 E Shore Dr Unit 2, Summerland Key, FL 33040

Property at 94825 Overseas Hwy #281, Key Largo, FL 33037, 4 beds, 3.5 baths

$940,000

4 beds3.5 baths1,540 sq ft

94825 Overseas Hwy #281, Key Largo, FL 33037

(305) 451-0060

Property at 21 Mutiny Pl, Key Largo, FL 33037, 5 beds, 4 baths

$3,799,000

5 beds4 baths3,906 sq ft

21 Mutiny Pl, Key Largo, FL 33037

Property at 1133 W Ocean Dr #13, Key Colony Beach, FL 33051, 3 beds, 2.5 baths

$1,050,000

3 beds2.5 baths1,750 sq ft

1133 W Ocean Dr #13, Key Colony Beach, FL 33051

Property at 88547 Old Hwy, Tavernier, FL 33070, 4 beds, 3 baths

$6,500,000

4 beds3 baths4,103 sq ft

88547 Old Hwy, Tavernier, FL 33070

Property at 875 50Th Street Gulf, Marathon, FL 33050, 5 beds, 5 baths

$5,499,000

5 beds5 baths4,146 sq ft

875 50Th Street Gulf, Marathon, FL 33050

Property at 7051 Harbor Village Dr, Duck Key, FL 33050, 2 beds, 1.5 baths

$599,000

2 beds1.5 baths900 sq ft

7051 Harbor Village Dr, Duck Key, FL 33050

Property at 162 Bayview Dr, Islamorada, FL 33036, 8 beds, 9 baths

$8,590,000

8 beds9 baths5,392 sq ft

162 Bayview Dr, Islamorada, FL 33036

(305) 667-4815

Property at 12399 Overseas Hwy #12, Marathon, FL 33050, 3 beds, 2.5 baths

$1,200,000

3 beds2.5 baths1,360 sq ft

12399 Overseas Hwy #12, Marathon, FL 33050

Property at 10877 Overseas Hwy #7, Marathon, FL 33050, 1 bed, 2 baths

$499,000

1 bed2 baths850 sq ft

10877 Overseas Hwy #7, Marathon, FL 33050

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Based on information submitted to the MLS GRID as of Thu Aug 27 2026. 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 Monroe County

There are currently 789 homes with pools for sale in Monroe County at a median listing price of $1.12M. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Monroe County stay on the market for 147 days. This map is refreshed with the newest listings in Monroe County every 15 minutes.

In the past month, 158 homes have been sold in Monroe County. In addition to houses in Monroe County, there were also 238 condos, 150 townhouses, and 64 multi-family units for sale in Monroe County last month. Find your dream home in Monroe County 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 Monroe County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Monroe County. If you're looking to sell your home in the Monroe County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Monroe County with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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