Homes with Pools for Sale in Monroe County, FL

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FLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Monroe County, FL:
Proven rental income meets the Florida Keys lifestyle in this solid CBS Marathon home featuring 60 ft. of concrete dockage with instant Gulf access. This well-established weekly rental property averages $105K in annual gross rental income and boasts 144 VRBO reviews with a 9.8 rating. (Future rentals must be honored by buyer). Enjoy a heated cocktail pool with sun shelf and waterfall spa, plus a fenced, low-maintenance yard and ample paver parking for boat trailers, RVs, and vehicles. Additional highlights include impact windows and doors, a metal roof and two storage sheds. Come see why this established, beloved neighborhood is such a special place to call home!

$1,539,000

3 beds2 baths1,623 sq ft

1791 Grouper Dr, Marathon, FL 33050

Metal roof • Fenced yard • Heated cocktail pool

ABOUT THIS HOME
Home with a Pool for sale in Monroe County, FL:
Turnkey Old Town Key West condo! 2 Bedrooms/2 Full Baths/ Fully Furnished/Pool-side/Rentals through March 2027! Welcome to your turnkey piece of Old Town Key West. This first-floor, poolside 2 Bedroom. 2 Bath condo is fully furnished, ready to enjoy now, and comes with future rentals already booked through March 2027. Whether you're looking for a Key West getaway or an established vacation rental, this property offers the flexibility to do both. The open and comfortable layout features 2 Bedrooms and 2 Full bathrooms, making it especially appealing for vacation guests, couples traveling together, or personal use. The condo is being sold fully furnished, allowing the next owner to begin enjo

$779,000

2 beds2 baths648 sq ft

906 Truman Ave #2, Key West, FL 33040

Hurricane panels • Outside covered area • Own washer and dryer

3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in Monroe County, FL:
Some waterfront homes offer a view. This one creates an entire lifestyle around it. Set along the Gulf within the sought-after gated Stirrup Key community, this beautifully appointed CBS residence captures panoramic open-water views, unforgettable sunsets, and a rare sense of privacy. Electronic gated entry and tropical surroundings create an immediate sense of arrival while extensive upgrades reflect elevated living and effortless enjoyment. Contemporary design and relaxed coastal living come together through an open, light-filled floor plan. Expansive impact windows and sliding glass doors frame the water from every angle, bringing the ever-changing Gulf backdrop into the interior. The ch

$4,499,000

3 beds4 baths2,983 sq ft

108 Sunset Dr, Marathon, FL 33050

Waterfront views • Waterfront pool • 0.54 acre lot

ABOUT THIS HOME
Home with a Pool for sale in Monroe County, FL:
Welcome to one of Buccaneer Point's most extraordinary waterfront estates-a breathtaking modern Balinese-inspired sanctuary where timeless architecture, exceptional craftsmanship, and resort-style living come together in perfect harmony. Situated on an oversized lot with more than 110 feet of waterfront, this custom CBS estate features a concrete roof, standing-seam metal roofing, and over $150,000 in professionally designed tropical landscaping. Dual electric gates welcome you with Royal Palms, Canary Island palms, bamboo, and mature privacy landscaping. Built for both everyday living and entertaining, the home offers expansive waterfront views, premium travertine and wood-look tile floori

$2,350,000

4 beds4 baths2,896 sq ft

40 N Bounty Ln, Key Largo, FL 33037

Waterfront estate • Custom cbs estate • Dual electric gates

OPEN SAT, 10AM TO 12PM3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in Monroe County, FL:
Welcome home to 101 Golf Club Drive, the key to your slice of paradise! This home is nestled mid-way in the gated Key West Golf Course Community and a short walk to pools, fitness center, butterfly garden, and a club house. From the home, the back faces unobstructed views of the 1st Fairway, while the front faces the quaint, white picket fence lined drive. Upstairs, each bedroom has its own bathroom and balcony, providing privacy to you and your family or guests. No need to make upgrades as new stainless steel appliances, hot water heater, flooring, insulation & paint are throughout! The home has also been recently tented with warranty, giving an additional peace of mind your home is

$649,999

2 beds2 baths900 sq ft

101 Golf Club Dr, Key West, FL 33040

Move in ready • $510 HOA • Pool

Property at 121 Calle Ensueno, Marathon, FL 33050, 4 beds, 3.5 baths

$2,800,000

4 beds3.5 baths3,079 sq ft

121 Calle Ensueno, Marathon, FL 33050

Property at 119 Simonton St, Key West, FL 33040, 4 beds, 4 baths

$3,600,000

4 beds4 baths2,691 sq ft

119 Simonton St, Key West, FL 33040

Property at 31536 Avenue F, Big Pine Key, FL 33043, 3 beds, 2 baths

$1,450,000

3 beds2 baths1,026 sq ft

31536 Avenue F, Big Pine Key, FL 33043

Property at 1518 Sunrise Dr, Big Pine Key, FL 33043, 3 beds, 2 baths

$1,400,000

3 beds2 baths1,540 sq ft

1518 Sunrise Dr, Big Pine Key, FL 33043

Property at 21 Mockingbird Rd, Key Largo, FL 33037, 4 beds, 2.5 baths

$775,000

4 beds2.5 baths1,352 sq ft

21 Mockingbird Rd, Key Largo, FL 33037

(305) 451-4422

Property at 74049 Overseas Hwy, Islamorada, FL 33036, 4 beds, 4 baths

$3,850,000

4 beds4 baths2,596 sq ft

74049 Overseas Hwy, Islamorada, FL 33036

(305) 809-7650

Property at 168 Indian Mound Trl, Tavernier, FL 33070, 4 beds, 3 baths

$3,700,000

4 beds3 baths3,204 sq ft

168 Indian Mound Trl, Tavernier, FL 33070

Property at 44 S Blackwater Ln, Key Largo, FL 33037, 5 beds, 4 baths

$2,950,000

5 beds4 baths2,509 sq ft

44 S Blackwater Ln, Key Largo, FL 33037

Property at 1657 Watson Blvd, Big Pine Key, FL 33043, 3 beds, 2 baths

$1,199,000

3 beds2 baths1,330 sq ft

1657 Watson Blvd, Big Pine Key, FL 33043

Property at 3206 Riviera Dr, Key West, FL 33040, 3 beds, 3.5 baths

$2,475,000

3 beds3.5 baths2,149 sq ft

3206 Riviera Dr, Key West, FL 33040

Property at 104000 Overseas Hwy Unit 1 - 2, Key Largo, FL 33037, 3 beds, 3 baths

$295,000

3 beds3 baths2,300 sq ft

104000 Overseas Hwy Unit 1 - 2, Key Largo, FL 33037

Property at 6203 Gulf Of Mexico Blvd #203, Marathon, FL 33050, 3 beds, 2 baths

$795,000

3 beds2 baths1,602 sq ft

6203 Gulf Of Mexico Blvd #203, Marathon, FL 33050

Property at 19 Spoonbill Way, Key West, FL 33040, 2 beds, 1.5 baths

$649,000

2 beds1.5 baths836 sq ft

19 Spoonbill Way, Key West, FL 33040

Property at 39 Mutiny Pl, Key Largo, FL 33037, 6 beds, 5.5 baths

$8,550,000

6 beds5.5 baths4,404 sq ft

39 Mutiny Pl, Key Largo, FL 33037

(305) 743-5181

Property at 210 Schooner Ln, Duck Key, FL 33050, 4 beds, 2 baths

$850,000

4 beds2 baths1,971 sq ft

210 Schooner Ln, Duck Key, FL 33050

Property at 26 Ocean Dr, Key Largo, FL 33037, 3 beds, 2 baths

$1,300,000

3 beds2 baths1,392 sq ft

26 Ocean Dr, Key Largo, FL 33037

Property at 1019 Whitehead St, Key West, FL 33040, 3 beds, 2.5 baths

$3,180,000

3 beds2.5 baths1,373 sq ft

1019 Whitehead St, Key West, FL 33040

Property at 10877 Overseas Hwy Apt 97, Marathon, FL 33050, 1 bed, 1.5 baths

$550,000

1 bed1.5 baths850 sq ft

10877 Overseas Hwy Apt 97, Marathon, FL 33050

Property at 157 Navajo St, Tavernier, FL 33070, 3 beds, 2 baths

$1,049,500

3 beds2 baths1,711 sq ft

157 Navajo St, Tavernier, FL 33070

(866) 595-6025

Property at 816 South St #4, Key West, FL 33040, 1 bed, 1 bath

$599,000

1 bed1 bath640 sq ft

816 South St #4, Key West, FL 33040

Property at 241 Hispanola Rd, Tavernier, FL 33070, 4 beds, 3 baths

$1,100,000

4 beds3 baths1,305 sq ft

241 Hispanola Rd, Tavernier, FL 33070

Property at 119 Coco Plum Dr, Marathon, FL 33050, 5 beds, 4.5 baths

$15,000,000

5 beds4.5 baths6,793 sq ft

119 Coco Plum Dr, Marathon, FL 33050

Property at 94825 Overseas Hwy Unit 82, Key Largo, FL 33037, 3 beds, 3 baths

$1,294,999

3 beds3 baths1,723 sq ft

94825 Overseas Hwy Unit 82, Key Largo, FL 33037

Property at 1901 S Roosevelt Blvd Unit 407N, Key West, FL 33040, 1 bed, 1 bath

$625,000

1 bed1 bath961 sq ft

1901 S Roosevelt Blvd Unit 407N, Key West, FL 33040

Property at 58652 Overseas Hwy, Grassy Key, FL 33050, 4 beds, 4 baths

$3,495,000

4 beds4 baths2,429 sq ft

58652 Overseas Hwy, Grassy Key, FL 33050

(305) 735-4095

Property at 1115 South St, Key West, FL 33040, 2 beds, 2 baths

$1,825,000

2 beds2 baths2,186 sq ft

1115 South St, Key West, FL 33040

Property at 9 Sombrero Blvd #108, Marathon, FL 33050, 2 beds, 2 baths

$509,000

2 beds2 baths1,001 sq ft

9 Sombrero Blvd #108, Marathon, FL 33050

Property at 1116 Truman Ave Unit A, Key West, FL 33040, 2 beds, 2 baths

$1,025,000

2 beds2 baths953 sq ft

1116 Truman Ave Unit A, Key West, FL 33040

Property at 573 Boyd Dr, Key Largo, FL 33037, 3 beds, 2 baths

$650,000

3 beds2 baths1,252 sq ft

573 Boyd Dr, Key Largo, FL 33037

Property at 300 N Anglers Dr, Marathon, FL 33050, 4 beds, 4.5 baths

$3,289,000

4 beds4.5 baths2,548 sq ft

300 N Anglers Dr, Marathon, FL 33050

Property at 65821 Overseas Hwy #307, Long Key, FL 33001, 3 beds, 2 baths

$825,000

3 beds2 baths914 sq ft

65821 Overseas Hwy #307, Long Key, FL 33001

Property at 699 116th Street Ocean, Marathon, FL 33050, 2 beds, 2 baths

$729,500

2 beds2 baths1,176 sq ft

699 116th Street Ocean, Marathon, FL 33050

Property at 106 Alynn Pl, Marathon, FL 33050, 3 beds, 2 baths

$1,900,000

3 beds2 baths1,170 sq ft

106 Alynn Pl, Marathon, FL 33050

Property at 75090 Overseas Hwy, Islamorada, FL 33036, 4 beds, 5.5 baths

$29,000,000

4 beds5.5 baths8,194 sq ft

75090 Overseas Hwy, Islamorada, FL 33036

(305) 712-8888

Property at 813 39Th St Gulf St, Marathon, FL 33050, 5 beds, 4 baths

$3,795,000

5 beds4 baths2,628 sq ft

813 39Th St Gulf St, Marathon, FL 33050

Property at 1318 Duncan St #3, Key West, FL 33040, 1 bed, 1 bath

$539,000

1 bed1 bath368 sq ft

1318 Duncan St #3, Key West, FL 33040

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Homes with Pools for Sale in Monroe County

There are currently 788 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, 149 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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