Homes with Pools for Sale in Monroe County, FL

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3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in Monroe County, FL:
Welcome to 524 Southard Street, an extraordinary luxury offering in the heart of Old Town Key West that blends upscale finishes, commercial versatility, & superior sustainable construction just steps from Duval Street. This fully renovated mixed-use property features 2,262 sq. ft. of refined interior space designed with modern industrial style & historic Key West character. Inside, soaring 14' ceilings, expansive porcelain tile & luxury vinyl flooring, & thoughtfully curated lighting create an atmosphere of understated sophistication. The custom chef's kitchen is beautifully appointed with quartz countertops, premium appliances, a generous walk-in pantry, & sleek

$3,100,000

3 beds3 baths2,262 sq ft

524 Southard St, Key West, FL 33040

Separate office • Fully renovated • Soaring 14 ceilings

ABOUT THIS HOME
Home with a Pool for sale in Monroe County, FL:
Ocean Isles Fishing Village is a seven-acre gated oceanfront complex. New construction with modern amenities in the heart of the Florida Keys. Conveniently located near local restaurants, shopping, attractions, airport. Great for boating enthusiasts, Easy water access with private boat ramp, newly updated marina, fish cleaning stations, assigned boat slips for owners, new seawall, bulkhead, docks, Olympic-sized waterfront pool, air-conditioned clubhouse, ice machine, tiki huts, outdoor grilling area, laundry facilities, stunning views! This studio unit is immaculate and comes fully furnished. It has its own washer and dryer on the main level. It also has 2 full bathrooms instead of the typi

$500,000

1 bed2 baths850 sq ft

10877 Overseas Hwy #30, Marathon, FL 33050

Oceanfront complex • New seawall • Private boat ramp

ABOUT THIS HOME
Home with a Pool for sale in Monroe County, FL:
Perfect Florida Keys townhouse with proven Rental Income! Located in resort style Mariners Club Key Largo - gated community, unit offers a unique opportunity to rent as a 4 bedroom/4 bathroom or a 2 bedroom/2 bathroom! Recently painted & some upgrades in downstairs unit, turnkey & low maintenance with 5 years of rental history on VRBO. Community Marina offers deep-water dockage, 2 oceanfront pools, 24-hr security, game room, community grills, tennis, pickleball, basketball, gym, & more! Boat dry dock storage & Jet ski storage available (Costs managed by HOA). No rental restrictions - manage independently or through a property manager. Pet friendly community for own

$955,000

4 beds4 baths2,500 sq ft

97501 Overseas Hwy #906, Key Largo, FL 33037

Gated community • Community marina • Oceanfront pools

(954) 545-5583

FLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Monroe County, FL:
Lending Available! Located in the highly desirable 55+ waterfront community of Silver Shores, this well-maintained, move-in-ready home offers large comfortable living space conveniently located near the clubhouse, marina, and pool. The spacious primary suite features an ensuite bath, while the flexible floor plan provides exceptional versatility. The second bedroom can easily serve as a home office and opens to an expansive third bedroom--currently used as a family room. With two private exterior entrances, this space is ideal for conversion into a separate guest suite or private quarters. An open-concept kitchen and living area create a welcoming central hub, highlighted by double sliding

$450,000

3 beds2 baths1,392 sq ft

812 S Silver Cir, Key Largo, FL 33037

4,500 sq ft lot • Parking • Community pool

(954) 545-5583

FLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Monroe County, FL:
A rare opportunity to own a fully renovated waterfront home that delivers both the Florida Keys lifestyle and exceptional investment potential. Offering five legal bedrooms, three legal bathrooms, and seven-day vacation rentals, this turnkey property presents projected rental income of up to $170,000 annually (per pro forma), making it equally appealing as a primary residence, second home, or income-producing investment. Located on a deep-water canal with approximately 75 feet of concrete dockage, a boat lift, fish-cleaning station, and private pool, you'll enjoy quick, easy access to the Gulf and the Atlantic through Vaca Cut--putting world-class fishing, sandbars, waterfront restaurants,

$2,150,000

5 beds3 baths2,719 sq ft

112 Bruce Ct, Marathon, FL 33050

Boat lift • Private pool • 7,500 sq ft lot

Property at 55 Ocean Front Dr, Key Largo, FL 33037, 4 beds, 3 baths

$2,550,000

4 beds3 baths4,446 sq ft

55 Ocean Front Dr, Key Largo, FL 33037

Property at 5950 Peninsular Ave #640, Key West, FL 33040

$2,500

— beds— baths— sq ft

5950 Peninsular Ave #640, Key West, FL 33040

Property at 207 E Bruce Ct, Marathon, FL 33050, 4 beds, 4 baths

$2,550,000

4 beds4 baths2,080 sq ft

207 E Bruce Ct, Marathon, FL 33050

Property at 441 3Rd St, Key Colony, FL 33051, 3 beds, 2 baths

$999,000

3 beds2 baths1,264 sq ft

441 3Rd St, Key Colony, FL 33051

Property at 21250 Conch Dr, Cudjoe Key, FL 33042, 3 beds, 2 baths

$1,399,000

3 beds2 baths1,508 sq ft

21250 Conch Dr, Cudjoe Key, FL 33042

Property at 362 E Seaview Dr, Duck Key, FL 33050, 4 beds, 3.5 baths

$3,695,000

4 beds3.5 baths3,479 sq ft

362 E Seaview Dr, Duck Key, FL 33050

Property at 902 S Ruby Dr, Key Largo, FL 33037, 2 beds, 2 baths

$475,000

2 beds2 baths1,259 sq ft

902 S Ruby Dr, Key Largo, FL 33037

Property at 1800 Atlantic Blvd Unit 427C, Key West, FL 33040, 2 beds, 2 baths

$1,025,000

2 beds2 baths1,311 sq ft

1800 Atlantic Blvd Unit 427C, Key West, FL 33040

Property at 401 Emma St Apt H, Key West, FL 33040, 2 beds, 2 baths

$2,999,500

2 beds2 baths1,770 sq ft

401 Emma St Apt H, Key West, FL 33040

Property at 1501 Georgia St, Key West, FL 33040, 4 beds, 4.5 baths

$3,599,000

4 beds4.5 baths2,810 sq ft

1501 Georgia St, Key West, FL 33040

Property at 200 Wrenn St Apt 510, Tavernier, FL 33070, 2 beds, 2 baths

$625,000

2 beds2 baths1,179 sq ft

200 Wrenn St Apt 510, Tavernier, FL 33070

Property at 800 Fleming St Unit C1, Key West, FL 33040, 2 beds, 2.5 baths

$2,445,000

2 beds2.5 baths1,550 sq ft

800 Fleming St Unit C1, Key West, FL 33040

Property at 94825 Overseas Hwy 100, Key Largo, FL 33037, 4 beds, 3 baths

$829,900

4 beds3 baths1,762 sq ft

94825 Overseas Hwy 100, Key Largo, FL 33037

(786) 877-3112

Property at 3 Evergreen Ave, Key West, FL 33040, 4 beds, 4 baths

$3,950,000

4 beds4 baths2,458 sq ft

3 Evergreen Ave, Key West, FL 33040

Property at 6204 Gulf Of Mexico Blvd #204, Marathon, FL 33050, 3 beds, 2 baths

$975,000

3 beds2 baths1,602 sq ft

6204 Gulf Of Mexico Blvd #204, Marathon, FL 33050

Property at 3312 Northside Dr #202, Key West, FL 33040, 2 beds, 2 baths

$429,900

2 beds2 baths792 sq ft

3312 Northside Dr #202, Key West, FL 33040

Property at 214 Eanes Ln, Key West, FL 33040, 4 beds, 3.5 baths

$3,300,000

4 beds3.5 baths2,573 sq ft

214 Eanes Ln, Key West, FL 33040

Property at 1614 Washington St, Key West, FL 33040, 4 beds, 4.5 baths

$4,495,000

4 beds4.5 baths2,806 sq ft

1614 Washington St, Key West, FL 33040

Property at 227 Sombrero Beach Rd, Marathon, FL 33050, 4 beds, 3 baths

$1,499,999

4 beds3 baths1,840 sq ft

227 Sombrero Beach Rd, Marathon, FL 33050

(786) 616-8368

Property at 247 W Seaview Cir, Duck Key, FL 33050, 4 beds, 3 baths

$1,374,499

4 beds3 baths2,519 sq ft

247 W Seaview Cir, Duck Key, FL 33050

Property at 617 Front St Unit A-52 Penthaus Week 52, Key West, FL 33040, 2 beds, 2 baths

$62,000

2 beds2 baths1,120 sq ft

617 Front St Unit A-52 Penthaus Week 52, Key West, FL 33040

Property at 57 Garden Cove Dr, Key Largo, FL 33037, 6 beds, 5.5 baths

$10,999,999

6 beds5.5 baths5,113 sq ft

57 Garden Cove Dr, Key Largo, FL 33037

(646) 480-7665

Property at 7028 Harbor Village Dr, Duck Key, FL 33050, 2 beds, 2 baths

$614,000

2 beds2 baths825 sq ft

7028 Harbor Village Dr, Duck Key, FL 33050

Property at 500 Burton Dr #1210, Tavernier, FL 33070, 2 beds, 2 baths

$529,999

2 beds2 baths826 sq ft

500 Burton Dr #1210, Tavernier, FL 33070

Property at 34 Golf Club Dr, Key West, FL 33040, 3 beds, 2 baths

$849,900

3 beds2 baths1,320 sq ft

34 Golf Club Dr, Key West, FL 33040

Property at 17013 Coral Dr, Sugarloaf Key, FL 33042, 4 beds, 3.5 baths

$5,200,000

4 beds3.5 baths2,660 sq ft

17013 Coral Dr, Sugarloaf Key, FL 33042

Property at 3312 Northside Dr #205, Key West, FL 33040, 1 bed, 1 bath

$330,000

1 bed1 bath528 sq ft

3312 Northside Dr #205, Key West, FL 33040

Property at 5605 College Rd Unit E305, Key West, FL 33040, 3 beds, 2 baths

$3,100,000

3 beds2 baths1,658 sq ft

5605 College Rd Unit E305, Key West, FL 33040

Property at 123 Golf Club Dr, Key West, FL 33040, 2 beds, 1.5 baths

$669,000

2 beds1.5 baths780 sq ft

123 Golf Club Dr, Key West, FL 33040

Property at 75071 Overseas Hwy, Islamorada, FL 33036, 3 beds, 2 baths

$3,199,000

3 beds2 baths1,260 sq ft

75071 Overseas Hwy, Islamorada, FL 33036

Property at 98282 Windward Ave #2, Key Largo, FL 33037, 2 beds, 2 baths

$409,000

2 beds2 baths778 sq ft

98282 Windward Ave #2, Key Largo, FL 33037

(305) 776-8703

Property at 17183 Coral Dr, Sugarloaf Key, FL 33042, 4 beds, 3.5 baths

$3,199,000

4 beds3.5 baths1,744 sq ft

17183 Coral Dr, Sugarloaf Key, FL 33042

Property at 88181 Old Hwy Unit F24, Islamorada, FL 33036, 2 beds, 2 baths

$775,000

2 beds2 baths1,330 sq ft

88181 Old Hwy Unit F24, Islamorada, FL 33036

Property at 308 Atlantic Blvd, Key Largo, FL 33037, 4 beds, 3 baths

$5,900,000

4 beds3 baths2,414 sq ft

308 Atlantic Blvd, Key Largo, FL 33037

Property at 1507 19th St, Key West, FL 33040, 3 beds, 2.5 baths

$1,410,000

3 beds2.5 baths1,610 sq ft

1507 19th St, Key West, FL 33040

Property at 325 Calusa St #312, Key Largo, FL 33037, 4 beds, 1.5 baths

$850,000

4 beds1.5 baths— sq ft

325 Calusa St #312, Key Largo, FL 33037

(786) 886-1908

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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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