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:
NEW CONSTRUCTION CO-OWNERSHIP POOL HOME! 1/10 Shares. 8 Shares are still available for sale for this brand-new coastal retreat on Ramrod Key. This luxury 4-bedroom, 3-bath residence delivers world-class construction, refined finishes, and effortless indoor-outdoor living in one of the most desirable boating neighborhoods in the Lower Keys. Built with solid CBS construction, a metal roof, and impact-rated windows & doors, this home offers long-term durability, energy efficiency, and peace of mind. Included in this price and soon to be added is a new pool and premium outdoor kitchen. Step inside to an open-concept layout bathed in natural light, highlighted by porcelain tile floors, a f

$175,000

4 beds3 baths2,120 sq ft

27433 Antigua Ln, Ramrod Key, FL 33042

Metal roof • New construction • Impact-rated windows

ABOUT THIS HOME
Home with a Pool for sale in Monroe County, FL:
Welcome to your dream coastal retreat, where breathtaking Gulf and Marina views await you from this desirable PENTHOUSE, top-floor end-unit deeded Timeshare week 37! Nestled within a secure, gated community, this resort-style property offers exceptional amenities, one unassigned parking space, a sauna, fitness center, and the on-site Pirates Cove Café. Enjoy front-row views as Coast Guard vessels and iconic pirate ships pass by just beyond your balcony. In the evenings, open the doors to take in the warm Gulf breeze and the soothing sounds of the water. Week 37 offers an ideal getaway--featuring warm weather, fewer crowds, and a relaxed island atmosphere! Ideally located just two blo

$26,000

2 beds2 baths1,120 sq ft

617 Front St Unit D-54 Week 37 Penthouse, Key West, FL 33040

Fitness center • Sauna • $132 HOA

FLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Monroe County, FL:
Turnkey Investment Opportunity just 0.3 miles from iconic Sombrero Beach, generating an impressive $116,000 in short-rental income in 2025. Fully furnished and 100% rental-ready, this property includes local rental management & future bookings already in place- allowing a new owner to step in and start earning immediately!(Future rentals must be honored by buyer) Enjoy the best of Keys living with a heated pool, lush private fenced yard and multiple porches including screened spaces for seamless indoor-outdoor living. Inside, the open-concept layout features abundant natural light and a modern kitchen ideal for entertaining. Built in 2016 to modern hurricane standards with impact wind

$995,000

2 beds2 baths1,350 sq ft

320 Calzada De Bougainville, Marathon, FL 33050

Private fenced yard • Multiple porches • Heated pool

(305) 743-8328

ABOUT THIS HOME
Home with a Pool for sale in Monroe County, FL:
A true tropical oasis nestled on a 6,600 sq ft lot with lush landscaping and a mature mango tree. Make this well maintained property your new home or INVESTMENT property. Currently in a successful vacation rental program. Fenced in for privacy and that sense of peace and tranquility. The backyard features a 14 x 30 custom concrete POOL with heater, chiller and colored lights. 7 x 7 spa tub and waterfall. Downstairs enclosure storage 20 x 34. Plenty of room for parking with RV parking and connections. 3 bedrooms and 2 bathrooms with 1360 sq ft of living space. Double French doors and impact resistance windows allow natural light throughout the home. Spacious open floor plan. Kitchen updated

$850,000

3 beds2 baths1,360 sq ft

216 Newfound Blvd, Big Pine Key, FL 33043

Mature mango tree • Waterfall • Custom concrete pool

OPEN TODAY, 3PM TO 4PM3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in Monroe County, FL:
Spectacular Bayfront Estate with Guesthouse in the Heart of Islamorada. & 7 Day Rental Potential, Seller Financing Available. Experience luxury coastal living at its finest in this exceptional Gated bayfront estate, ideally situated in the heart of Islamorada. Set on a rare peninsula with over 225 feet of prime waterfront, this property offers unmatched privacy, panoramic views, and direct access to both the Florida Bay and Atlantic Ocean. Seller will consider all reasonable offers. The main residence features 7 spacious bedrooms and 5 beautifully appointed bathrooms designed with both elegance and comfort in mind--perfect for entertaining or hosting large gatherings. A dramatic third-

$6,999,000

8 beds6 baths3,649 sq ft

1101 Mastic St, Upper Matecumbe Key Islamorada, FL 33036

Guesthouse • Bayfront estate • Direct access

(954) 545-5583

Property at 1540 Lantana Ln, Big Pine Key, FL 33043, 3 beds, 2 baths

$899,000

3 beds2 baths1,418 sq ft

1540 Lantana Ln, Big Pine Key, FL 33043

Property at 617 Front St Unit B51 Week 36 Penthouse, Key West, FL 33040, 2 beds, 2 baths

$32,500

2 beds2 baths1,120 sq ft

617 Front St Unit B51 Week 36 Penthouse, Key West, FL 33040

Property at 600 Elizabeth St, Key West, FL 33040, 4 beds, 5.5 baths

$4,300,000

4 beds5.5 baths3,092 sq ft

600 Elizabeth St, Key West, FL 33040

Property at 1019 Eaton St, Key West, FL 33040, 3 beds, 2 baths

$1,880,000

3 beds2 baths1,458 sq ft

1019 Eaton St, Key West, FL 33040

Property at 29562 Saratoga Ave, Big Pine Key, FL 33043, 4 beds, 2 baths

$1,435,000

4 beds2 baths2,310 sq ft

29562 Saratoga Ave, Big Pine Key, FL 33043

Property at 150 Azalea St, Tavernier, FL 33070, 4 beds, 2 baths

$1,849,000

4 beds2 baths— sq ft

150 Azalea St, Tavernier, FL 33070

(954) 545-5583

Property at 617 Front St Unit C54 Penthaus Wk36, Key West, FL 33040, 2 beds, 2 baths

$59,900

2 beds2 baths1,120 sq ft

617 Front St Unit C54 Penthaus Wk36, Key West, FL 33040

Property at 169 Venetian Way, Islamorada, FL 33070, 5 beds, 3 baths

$1,650,000

5 beds3 baths2,941 sq ft

169 Venetian Way, Islamorada, FL 33070

Property at 112 N Bounty Ln, Key Largo, FL 33037, 5 beds, 5 baths

$4,975,000

5 beds5 baths4,822 sq ft

112 N Bounty Ln, Key Largo, FL 33037

(305) 595-6804

Property at 167 Valois Blvd, Key Largo, FL 33037, 2 beds, 2 baths

$945,000

2 beds2 baths— sq ft

167 Valois Blvd, Key Largo, FL 33037

(305) 303-1844

Property at 617 Front St Unit A52 Penthaus Week32, Key West, FL 33040, 2 beds, 2 baths

$59,000

2 beds2 baths1,120 sq ft

617 Front St Unit A52 Penthaus Week32, Key West, FL 33040

Property at 87 Marina Ave, Key Largo, FL 33037, 4 beds, 3 baths

$749,000

4 beds3 baths1,666 sq ft

87 Marina Ave, Key Largo, FL 33037

Property at 1083 Labat Ln, Cudjoe Key, FL 33042, 3 beds, 3 baths

$3,300,000

3 beds3 baths2,295 sq ft

1083 Labat Ln, Cudjoe Key, FL 33042

Property at 200 Plantation Shores Dr, Tavernier, FL 33070, 2 beds, 2.5 baths

$2,090,000

2 beds2.5 baths960 sq ft

200 Plantation Shores Dr, Tavernier, FL 33070

(786) 479-9937

Property at 29 Key Haven Rd, Key West, FL 33040, 5 beds, 4.5 baths

$5,700,000

5 beds4.5 baths2,906 sq ft

29 Key Haven Rd, Key West, FL 33040

Property at 57783 Morton St, Grassy Key, FL 33050, 10 beds, 12 baths

$29,500,000

10 beds12 baths8,648 sq ft

57783 Morton St, Grassy Key, FL 33050

(305) 800-9030

Property at 325 25Th St, Marathon, FL 33050, 3 beds, 2.5 baths

$545,000

3 beds2.5 baths1,488 sq ft

325 25Th St, Marathon, FL 33050

Property at 95410 Overseas Hwy, Key Largo, FL 33037, 6 beds, 6.5 baths

$16,900,000

6 beds6.5 baths3,862 sq ft

95410 Overseas Hwy, Key Largo, FL 33037

Property at 88845 Old Hwy, Tavernier, FL 33070, 5 beds, 7 baths

$27,000,000

5 beds7 baths8,200 sq ft

88845 Old Hwy, Tavernier, FL 33070

(646) 480-7665

Property at 212 Buttonwood Ln, Tavernier, FL 33070, 3 beds, 2 baths

$670,000

3 beds2 baths1,758 sq ft

212 Buttonwood Ln, Tavernier, FL 33070

(786) 402-2514

Property at 21012 6th Ave, Cudjoe Key, FL 33042, 2 beds, 2 baths

$1,399,000

2 beds2 baths1,372 sq ft

21012 6th Ave, Cudjoe Key, FL 33042

Property at 3612 Sunrise Dr, Key West, FL 33040, 3 beds, 2 baths

$2,499,000

3 beds2 baths1,641 sq ft

3612 Sunrise Dr, Key West, FL 33040

Property at 1109 Stump Ln, Key West, FL 33040, 3 beds, 3 baths

$2,249,000

3 beds3 baths1,724 sq ft

1109 Stump Ln, Key West, FL 33040

Property at 591 Sombrero Beach Rd Apt 1B, Marathon, FL 33050, 2 beds, 2.5 baths

$684,000

2 beds2.5 baths1,500 sq ft

591 Sombrero Beach Rd Apt 1B, Marathon, FL 33050

Property at 912 James St #2, Key West, FL 33040, 3 beds, 2.5 baths

$1,349,000

3 beds2.5 baths1,020 sq ft

912 James St #2, Key West, FL 33040

Property at 55 Boca Chica Rd #27, Key West, FL 33040, 2 beds, 2 baths

$532,000

2 beds2 baths1,064 sq ft

55 Boca Chica Rd #27, Key West, FL 33040

Property at 27215 Mariposa Rd, Ramrod Key, FL 33042, 3 beds, 3 baths

$819,000

3 beds3 baths1,500 sq ft

27215 Mariposa Rd, Ramrod Key, FL 33042

Property at 101551 Overseas Hwy #159, Key Largo, FL 33037, 2 beds, 1.5 baths

$355,000

2 beds1.5 baths416 sq ft

101551 Overseas Hwy #159, Key Largo, FL 33037

Property at 88351 Old Hwy, Islamorada, FL 33070, 6 beds, 9 baths

$14,990,000

6 beds9 baths7,590 sq ft

88351 Old Hwy, Islamorada, FL 33070

(305) 674-4000

Property at 60 Ocean Front Dr, Key Largo, FL 33037, 3 beds, 3 baths

$5,250,000

3 beds3 baths2,950 sq ft

60 Ocean Front Dr, Key Largo, FL 33037

(305) 833-3303

Property at 16750 Old State Road 4A, Sugarloaf Key, FL 33042, 6 beds, 4.5 baths

$8,995,000

6 beds4.5 baths5,208 sq ft

16750 Old State Road 4A, Sugarloaf Key, FL 33042

Property at 101 11th St #19, Marathon, FL 33050, 2 beds, 2 baths

$399,000

2 beds2 baths960 sq ft

101 11th St #19, Marathon, FL 33050

Property at 431 12th St, Key Colony Beach, FL 33051, 4 beds, 4 baths

$3,700,000

4 beds4 baths4,369 sq ft

431 12th St, Key Colony Beach, FL 33051

Property at 14 Avenue F, Marathon, FL 33050, 4 beds, 3.5 baths

$2,780,000

4 beds3.5 baths3,224 sq ft

14 Avenue F, Marathon, FL 33050

(305) 587-3663

Property at 210 W Seaview Cir, Duck Key, FL 33050, 4 beds, 4 baths

$4,950,000

4 beds4 baths3,304 sq ft

210 W Seaview Cir, Duck Key, FL 33050

Property at 906 Johnson St, Key West, FL 33040, 6 beds, 5.5 baths

$5,500,000

6 beds5.5 baths3,751 sq ft

906 Johnson St, Key West, FL 33040

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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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