Homes with Pools for Sale in Monroe County, FL

789 homes

Sort:

Recommended

ABOUT THIS HOME
Home with a Pool for sale in Monroe County, FL:
"UPDATES" 3/15/26 Freshly painted exterior, new pergola for relaxing on the dock, new fence, and new pool heater/chiller. Embrace the open bright treehouse feel of this renovated home tucked away on a dead-end street in sought after Twin Lakes subdivision. 40 minutes from Miami yet feeling like a tropical Oasis. Catch the breeze from the wrap around porches or the sunset from the large rooftop patio with a view of Blackwater Sound. The 65' Trex dock can be home to your boat, ski's and other water toys on the deep and wide canal. From the vaulted ceilings, beautiful eucalyptus flooring, large master suite, whole house Generac generator you will feel like you are on vacation every d

$2,100,000

3 beds2.5 baths2,100 sq ft

894 Ellen Dr, Key Largo, FL 33037

65 trex dock • Wrap around porches • Deep and wide canal

(305) 451-1020

ABOUT THIS HOME
Home with a Pool for sale in Monroe County, FL:
Large, Bayfront parcel with over 43' of easily accessible dockage with 12,000 lb. boat lift, and a 2019 Heartland Landmark 365 Phoenix 5th Wheel . Rare offering; one of only twenty Bayfront lots available in Calusa Campground. Take in beautiful open-water views with easy access to the shimmering Florida Bay, which is perfect for boating, fishing, and long, sun-soaked days on the water. Whether you're craving adventure or a peaceful escape, this home offers the best of both worlds in seamless balance. Calusa is a lively, amenity-filled community built for relaxation and recreation alike. Residents enjoy a playground, tennis and basketball courts, a sparkling pool, plus a convenient boat ramp

$795,000

1 bed1 bath440 sq ft

325 Calusa St #222, Key Largo, FL 33037

Boat lift • Open-water views • Bayfront parcel

ABOUT THIS HOME
Home with a Pool for sale in Monroe County, FL:
Two well kept condo units at Solana Village in Key West's New Town neighborhood represents a solid investment opportunity. Conveniently situated near local schools, government offices, retail centers, a movie theater, and marinas, the property offers both lifestyle and income potential. The second-floor unit (13) is a 2-bedroom, 2-bathroom with all-tile flooring and a private balcony currently rented for $2,975, while the first-floor unit (13A ) is a 1 bedroom, 1 bathroom both in move-in ready, rentable condition estimating $2,675 monthly rent. Investors can lease out both units for steady rental income, or choose to live in one while renting the other to help cover mortgage and ongoing exp

$675,000

3 beds3 baths1,358 sq ft

3314 Northside Dr Unit 13 & 13A, Key West, FL 33040

Move-in ready • Private balcony • All-tile flooring

ABOUT THIS HOME
Home with a Pool for sale in Monroe County, FL:
New Standing Seam Metal Roof !! New railings too. This Condo Grossed $35,269.00 in the first 6 months of 2026 Top Floor 2/2 Condo with an Ocean View. Upgraded condo with nice furniture arraignment that gives a comfortable open space feel. Updated Kitchen and both bathrooms have nice tiled floors & walls matching tiled floors throughout, Impact windows and doors too. Protected Marina with direct Ocean access, Private Oceanfront Café & Lounge, Heated Jr. Olympic pool w/ 14 person Spa, Pool Bar too !! Light tennis & pickle ball courts. Beach & boardwalk & gazebo.

$569,000

2 beds2 baths826 sq ft

500 Burton Dr #1415, Tavernier, FL 33070

Updated kitchen • Protected marina • Direct ocean access

ABOUT THIS HOME
Home with a Pool for sale in Monroe County, FL:
Big, beautiful, and exceptionally solid, this waterfront Islamorada residence is perfectly situated on Sandy Cove Basin with protected deep-water dockage for multiple boats and direct bay access. A gated, pavered double driveway leads to an inviting foyer where marble floors and a private elevator welcome you. The elevated living level features a spacious great room with fireplace and coral accents, ideal for entertaining, along with a chef's kitchen offering custom teak cabinetry, granite countertops, island cooktop, and premium Sub-Zero and Bosch appliances. Wide screened porches extend the living space and capture open waterfront views. The home offers 5 bedrooms and 5.5 baths, a resort-

$6,150,000

5 beds5.5 baths5,456 sq ft

137 Sapodilla Dr, Islamorada, FL 33036

0.41 acre lot • 2 garage spots • Pool

(305) 712-8888

Property at 3312 Northside Dr #405, Key West, FL 33040, 1 bed, 1 bath

$343,500

1 bed1 bath528 sq ft

3312 Northside Dr #405, Key West, FL 33040

Property at 352 Sound Dr, Key Largo, FL 33037, 4 beds, 3.5 baths

$5,199,000

4 beds3.5 baths3,622 sq ft

352 Sound Dr, Key Largo, FL 33037

Property at 3513 Sunrise Dr, Key West, FL 33040, 3 beds, 3 baths

$2,165,000

3 beds3 baths2,569 sq ft

3513 Sunrise Dr, Key West, FL 33040

Property at 701 Spanish Main Dr #604, Cudjoe Key, FL 33042, 2 beds, 2 baths

$595,000

2 beds2 baths816 sq ft

701 Spanish Main Dr #604, Cudjoe Key, FL 33042

Property at 1001 W Ocean Dr Unit 1-201, Key Colony Beach, FL 33051, 2 beds, 2 baths

$749,000

2 beds2 baths1,352 sq ft

1001 W Ocean Dr Unit 1-201, Key Colony Beach, FL 33051

Property at 212 Banyan Ln, Tavernier, FL 33070, 5 beds, 4 baths

$1,800,000

5 beds4 baths1,467 sq ft

212 Banyan Ln, Tavernier, FL 33070

(888) 668-8283

Property at 200 Wrenn #502, Tavernier, FL 33070, 1 bed, 1 bath

$410,000

1 bed1 bath— sq ft

200 Wrenn #502, Tavernier, FL 33070

(305) 595-6804

Property at 81801 Overseas Hwy #727, Islamorada, FL 33036, 1 bed, 1 bath

$585,000

1 bed1 bath358 sq ft

81801 Overseas Hwy #727, Islamorada, FL 33036

Property at 317 E Seaview Cir, Duck Key, FL 33050, 3 beds, 2.5 baths

$2,200,000

3 beds2.5 baths3,172 sq ft

317 E Seaview Cir, Duck Key, FL 33050

Property at 15 Sombrero Blvd Unit 212W, Marathon, FL 33050, 2 beds, 2 baths

$465,000

2 beds2 baths962 sq ft

15 Sombrero Blvd Unit 212W, Marathon, FL 33050

Property at 55 Boca Chica Rd #57, Key West, FL 33040, 1 bed, 1 bath

$239,000

1 bed1 bath420 sq ft

55 Boca Chica Rd #57, Key West, FL 33040

Property at 5030 5Th Ave #61, Stock Island, FL 33040, 3 beds, 2.5 baths

$615,600

3 beds2.5 baths1,274 sq ft

5030 5Th Ave #61, Stock Island, FL 33040

Property at 764 Michael Dr, Key Largo, FL 33037, 3 beds, 3.5 baths

$1,895,000

3 beds3.5 baths2,024 sq ft

764 Michael Dr, Key Largo, FL 33037

Property at 109 Avenue D Apt 307, Marathon, FL 33050, 1 bath

$339,000

Studio1 bath425 sq ft

109 Avenue D Apt 307, Marathon, FL 33050

Property at 701 Spanish Main Dr #495, Cudjoe Key, FL 33042, 2 beds, 2 baths

$639,000

2 beds2 baths864 sq ft

701 Spanish Main Dr #495, Cudjoe Key, FL 33042

Property at 272 W Seaview Dr, Duck Key, FL 33050, 3 beds, 3 baths

$2,350,000

3 beds3 baths2,028 sq ft

272 W Seaview Dr, Duck Key, FL 33050

Property at 80450 Overseas Hwy Apt 106, Islamorada, FL 33036, 2 beds, 2.5 baths

$550,000

2 beds2.5 baths1,303 sq ft

80450 Overseas Hwy Apt 106, Islamorada, FL 33036

Property at 1631 Sunrise Dr, Big Pine Key, FL 33043, 3 beds, 2 baths

$2,200,000

3 beds2 baths1,804 sq ft

1631 Sunrise Dr, Big Pine Key, FL 33043

Property at 123 W Bruce Ct, Marathon, FL 33050, 4 beds, 3 baths

$2,950,000

4 beds3 baths2,297 sq ft

123 W Bruce Ct, Marathon, FL 33050

Property at 222 2nd Rd, Key Largo, FL 33037, 3 beds, 2 baths

$899,999

3 beds2 baths1,556 sq ft

222 2nd Rd, Key Largo, FL 33037

(877) 366-2213

Property at 94825 Overseas Hwy #187, Key Largo, FL 33037, 3 beds, 2.5 baths

$950,000

3 beds2.5 baths1,650 sq ft

94825 Overseas Hwy #187, Key Largo, FL 33037

(786) 605-5550

Property at 2601 S Roosevelt Blvd Unit 406A, Key West, FL 33040, 2 beds, 1.5 baths

$940,000

2 beds1.5 baths980 sq ft

2601 S Roosevelt Blvd Unit 406A, Key West, FL 33040

Property at 1001 W Ocean Dr Unit 1-204, Key Colony Beach, FL 33051, 2 beds, 2 baths

$755,000

2 beds2 baths1,260 sq ft

1001 W Ocean Dr Unit 1-204, Key Colony Beach, FL 33051

Property at 2601 S Roosevelt Blvd Unit 204A, Key West, FL 33040, 1 bed, 1 bath

$625,000

1 bed1 bath754 sq ft

2601 S Roosevelt Blvd Unit 204A, Key West, FL 33040

Property at 81801 Overseas Hwy #729, Islamorada, FL 33036, 1 bed, 1 bath

$699,000

1 bed1 bath550 sq ft

81801 Overseas Hwy #729, Islamorada, FL 33036

Property at 2613 Gulfview Dr, Key West, FL 33040, 3 beds, 3 baths

$1,549,000

3 beds3 baths1,320 sq ft

2613 Gulfview Dr, Key West, FL 33040

Property at 1320 6th St, Key West, FL 33040, 5 beds, 3 baths

$2,200,000

5 beds3 baths2,096 sq ft

1320 6th St, Key West, FL 33040

Property at 48 E Playa Largo Blvd, Key Largo, FL 33037, 4 beds, 4.5 baths

$3,900,000

4 beds4.5 baths2,807 sq ft

48 E Playa Largo Blvd, Key Largo, FL 33037

Property at 80639 Old Hwy #309, Islamorada, FL 33036, 3 beds, 3 baths

$2,730,000

3 beds3 baths2,275 sq ft

80639 Old Hwy #309, Islamorada, FL 33036

Property at 423 Sombrero Beach Rd #10, Marathon, FL 33050, 3 beds, 2.5 baths

$559,000

3 beds2.5 baths1,427 sq ft

423 Sombrero Beach Rd #10, Marathon, FL 33050

Property at 280/290 3rd St, Key Colony, FL 33051, 4 beds, 4 baths

$1,495,000

4 beds4 baths1,536 sq ft

280/290 3rd St, Key Colony, FL 33051

Property at 2601 S Roosevelt Blvd Unit 304C, Key West, FL 33040, 3 beds, 2 baths

$799,000

3 beds2 baths1,221 sq ft

2601 S Roosevelt Blvd Unit 304C, Key West, FL 33040

Property at 141 Grassy Rd, Key Largo, FL 33037, 5 beds, 4.5 baths

$3,995,000

5 beds4.5 baths3,600 sq ft

141 Grassy Rd, Key Largo, FL 33037

Property at 150 Rushton Ln, Tavernier, FL 33070, 3 beds, 3 baths

$2,900,000

3 beds3 baths1,743 sq ft

150 Rushton Ln, Tavernier, FL 33070

(305) 989-1667

Property at 10999 Ave 3rd Ave, Marathon, FL 33050, 2 beds, 3 baths

$1,700,000

2 beds3 baths1,247 sq ft

10999 Ave 3rd Ave, Marathon, FL 33050

Property at 1607 Sunrise Dr, Big Pine Key, FL 33043, 2 beds, 2 baths

$1,850,000

2 beds2 baths1,980 sq ft

1607 Sunrise Dr, Big Pine Key, FL 33043

Viewing page 15 of 20

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.

More real estate resources for Monroe County, FL

Nearby Counties

Cities

Nearby Counties with Homes with Pools

Nearby Cities with Homes with Pools

More to explore in Monroe County, FL

How to buy a house in Monroe County, FL

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Popular Markets in Florida

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.