Monroe County, FL Homes

• 

  

  

  /39

  $1,999,999

  $450K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,710 Sq Ft

  415 Sombrero Beach Rd, Marathon, FL 33050

  Discover an extraordinary waterfront oasis in the heart of the Florida Keys. Located just moments from the pristine sands of Sombrero Beach, this elegant estate blends modern sophistication with the relaxed charm of coastal living. Designed for the discerning buyer, every detail of this property reflects luxury, comfort, and an unparalleled boating lifestyle. Elevated foundation - permitted for

  

  Tyler Weant

  Keller Williams Key West Compass Realty

  415 Sombrero Beach Rd, Marathon, FL 33050
• 

  

  

  /18

  $4,500 Per Month

  • 3 Beds
  • 2.5 Baths
  • House for Rent

  480-490 90th Street Ocean, Marathon, FL 33050

  Property Id: 1581244 Enjoy comfortable Florida Keys living in this spacious 3-bedroom, 2.5-bath single-family home with approximately 1,918 sq. ft. of living space in Marathon. This elevated home offers the privacy and space of a single-family residence, with plenty of room both inside and out. Enjoy a spacious partially fenced yard, screened outdoor living space, large covered area

  480-490 90th Street Ocean, Marathon, FL 33050
• 

  

  

  /64

  $3,580,000

  Sold Sep 17, 2025

  180 13th St, Key Colony Beach, FL 33051

  • 5 Beds
  • 4.5 Baths
  • 2,741 Sq Ft
  • Built 2022

  Last Sold Summary

  • 7% Below List Price
  • $1,306/SF
  • 276 Days On Market

  Current Estimated Value $3,615,992

  Last Listing Agent Becky Newman Better Homes and Gardens Real Estate Destinations

  180 13th St, Key Colony Beach, FL 33051
• 

  

  

  /3

  Not Listed For Sale

  33 Judy Place, Key Largo, FL 33037

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1973

  33 Judy Place, Key Largo, FL 33037

  Last Sold Summary

  • 22 Days On Market

  Last Listing Agent Susan Holler LoKation
• 

  

  

  /44

  $984,000

  • 4 Beds
  • 3 Baths
  • 1,869 Sq Ft

  1025 Snapper Ln, Key Largo, FL 33037

  Welcome to your brand-new island retreat in Key Largo, where modern luxury meets laid-back coastal living. This beautifully constructed residence offers 3 spacious bedrooms, 2 designer bathrooms, and 1,375 sq. ft. of elevated living space. Offering exceptional value in today's market, this home stands out with luxury finishes and one of the most attractive price-per-square-foot values in the

  

  Philip Kravitz

  Coldwell Banker Schmitt Key Largo

  1025 Snapper Ln, Key Largo, FL 33037
• 

  

  /20

  $9,796

  Total Monthly Price

  • 4 Beds
  • 4 Baths
  • 2,292 Sq Ft
  • Condo for Rent

  841 Copa D Oro W Unit SI ID1608714P, Marathon, FL 33050

  The advertised rate of $9,797/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 17, 2026. Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can

  841 Copa D Oro W Unit SI ID1608714P, Marathon, FL 33050
• 

  

  /60

  $950,000

  Sold Oct 17, 2025

  76 W Shore Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,028 Sq Ft
  • Built 2001

  Last Sold Summary

  • 13% Below List Price
  • $924/SF
  • 369 Days On Market

  Current Estimated Value $966,101

  Last Listing Agent Cardenas & Krug Team Coastal Collection Real Estate Inc.

  76 W Shore Dr, Summerland Key, FL 33042
• 

  

  /46

  Not Listed For Sale

  2 Oakwood Ave, Key Largo, FL 33037

  • 3 Beds
  • 2 Baths
  • 1,484 Sq Ft
  • Built 1991

  2 Oakwood Ave, Key Largo, FL 33037

  Last Sold Summary

  • 62 Days On Market

  Last Listing Agent Kelly Randin Sharon J. Kelly Realty, Inc.
• 

  

  /42

  $749,000

  $150K PRICE DROP Under Contract

  • 4 Beds
  • 3 Baths
  • 1,666 Sq Ft

  87 Marina Ave, Key Largo, FL 33037

  Watch fireworks from your rooftop deck, relax by your heated and chilled pool, and keep your boat trailered in your own backyard ready to launch at the marina down the street!Welcome to this beautifully maintained 4-bedroom, 3-bathroom home in the highly sought-after Port Largo neighborhood of Key Largo. Offering 1,666 sq ft of bright living space, soaring ceilings, skylights, and a private

  

  Philip Kravitz

  Coldwell Banker Schmitt Key Largo

  87 Marina Ave, Key Largo, FL 33037
• 

  

  /20

  $3,335

  Total Monthly Price

  • 2 Beds
  • 1 Bath
  • 1,119 Sq Ft
  • Condo for Rent

  97652 Overseas Hwy Unit SI FL2-ID1546120P, Key Largo, FL 33037

  The advertised rate of $3,335/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 19, 2027. Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

  97652 Overseas Hwy Unit SI FL2-ID1546120P, Key Largo, FL 33037
• 

  

  /4

  $2,315,000

  Sold Feb 20, 2026

  1309 Petronia St, Key West, FL 33040

  • 3 Beds
  • 3 Baths
  • 1,675 Sq Ft
  • Built 1938

  Last Sold Summary

  • 2% Below List Price
  • $1,382/SF
  • 30 Days On Market

  Current Estimated Value $2,315,881

  Last Listing Agent Bobby Coe RE/MAX Keys Connection (KW)

  1309 Petronia St, Key West, FL 33040
• 

  

  /24

  Est $1,933,887

  Not Listed For Sale

  108 S Bahama Dr, Marathon, FL 33050

  • 4 Beds
  • Built 2023

  108 S Bahama Dr, Marathon, FL 33050

  Last Sold Summary

  • 187 Days On Market

  Last Listing Agent Debra Grill, Pa Prestige Realty Group MTH
• 

  

  /65

  $2,499,000

  $300K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 2,124 Sq Ft

  156 Sea Ln, Geiger Key, FL 33040

  Experience modern waterfront living at this exceptional 2-Bed, 2.5-Bath oceanfront home on Geiger Key, where striking contemporary design meets one of the Florida Keys' most thoughtfully engineered homes. Designed to maximize breathtaking open water views, this architecturally striking residence, envisioned by original owner and renowned author Reese Palley, seamlessly blends contemporary design,

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  156 Sea Ln, Geiger Key, FL 33040
• 

  

  /18

  $3,250 Per Month

  • 2 Beds
  • 2 Baths
  • 1,062 Sq Ft
  • House for Rent

  1635 Pandorea Ln, Big Pine Key, FL 33043

  Welcome to your ideal rental in Big Pine Key, Florida! This charming property offers a perfect environment for those seeking a peaceful lifestyle close to nature and conveniences. Key Property Features include a spacious living area designed for comfort, ensuring you have plenty of room to relax and entertain. Enjoy the benefit of central heating and air conditioning, complemented by ceiling

  1635 Pandorea Ln, Big Pine Key, FL 33043
• 

  /2

  $1,030,000

  Sold Nov 19, 2025

  22521 Jolly Roger Dr, Cudjoe Key, FL 33042

  • 4 Beds
  • 2.5 Baths
  • 1,728 Sq Ft
  • Built 2010

  Last Sold Summary

  • $596/SF
  • 0 Days On Market

  Current Estimated Value $1,100,994

  Last Listing Agent Patti Nickless Coldwell Banker Schmitt Lower Keys (KW)

  22521 Jolly Roger Dr, Cudjoe Key, FL 33042
• 

  Not Listed For Sale

  81 Tarpon Basin Dr, Key Largo, FL 33037

  • 2 Beds
  • 1 Bath
  • 470 Sq Ft
  • Built 1965

  81 Tarpon Basin Dr, Key Largo, FL 33037

  Last Sold Summary

  • 8 Days On Market

  Last Listing Agent Maria Canto American Caribbean Real Estate
• 

  

  /41

  $599,888

  $25K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 947 Sq Ft

  104350 Overseas Hwy Unit A204, Key Largo, FL 33037

  Turnkey Florida Keys Condo with Weekly Rentals Allowed - Fully Furnished in Moon BayAct now, purchase before the peak rental season and start capitalizing on this income producing property right away! Rental history is available upon request.This fully furnished 2BR / 1.5BA condo plus den (3rd sleeping area) in Moon Bay offers 947 sq ft of bright, comfortable living space and is ready for

  

  Philip Kravitz

  Coldwell Banker Schmitt Key Largo

  104350 Overseas Hwy Unit A204, Key Largo, FL 33037
• 

  

  /16

  $9,148

  Total Monthly Price

  • 2 Beds
  • 1 Bath
  • 796 Sq Ft
  • Condo for Rent

  169 Golf Club Dr Unit SI FL1-ID1545690P, Key West, FL 33040

  The advertised rate of $9,149/month is the lowest available price, based on a 1 month(s) and 2 day(s) stay with a move-in date of February 23, 2027. Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed

  169 Golf Club Dr Unit SI FL1-ID1545690P, Key West, FL 33040
• 

  

  /33

  $910,000

  Sold Apr 13, 2026

  151 Cutthroat Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2.5 Baths
  • 1,140 Sq Ft
  • Built 1975

  Last Sold Summary

  • 4% Below List Price
  • $798/SF
  • 46 Days On Market

  Current Estimated Value $920,617

  Last Listing Agent Heather Bennett Florida Keys Real Estate Co. (KW)

  151 Cutthroat Dr, Summerland Key, FL 33042
• 

  

  /30

  Est $3,179,087

  Not Listed For Sale

  27 Sunset Key Dr, Key West, FL 33040

  27 Sunset Key Dr, Key West, FL 33040

  Last Sold Summary

  • 349 Days On Market

  Last Listing Agent Cardenas & Krug Team Coastal Collection Real Estate Inc.
• 

  

  /68

  $37,500

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft

  617 Front St Unit B-24 Week 45, Key West, FL 33040

  Experience deeded ownership of the same week, each year (Week 45) at the highly desirable Galleon Resort with this premier timeshare opportunity. This unit showcases a wonderful location and some of the most spectacular sunsets in all of Key West.Filled with natural light, the residence also features a private balcony perfectly positioned to capture the stunning waterfront scenery above the

  

  Stephanie Herrmann

  Truman & Co. (KW)

  617 Front St Unit B-24 Week 45, Key West, FL 33040
• 

  

  /20

  $5,837

  Total Monthly Price

  • 3 Beds
  • 3 Baths
  • 1,054 Sq Ft
  • Condo for Rent

  394 Burton Dr Unit SI ID1546416P, Tavernier, FL 33070

  The advertised rate of $5,837/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 17, 2026. Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can

  394 Burton Dr Unit SI ID1546416P, Tavernier, FL 33070
• 

  

  /42

  $305,000

  Sold Aug 14, 2026

  282 Scorpio Ln, Key West, FL 33040

  • 1 Bed
  • 1 Bath
  • 552 Sq Ft
  • Built 1975

  Last Sold Summary

  • 6% Below List Price
  • $553/SF
  • 14 Days On Market

  Last Listing Agent Robin Mitchell Keller Williams Key West Compass Realty

  282 Scorpio Ln, Key West, FL 33040
• 

  /2

  Est $1,637,294

  Not Listed For Sale

  40 Sunset Key Dr, Key West, FL 33040

  • Studio

  40 Sunset Key Dr, Key West, FL 33040
• 

  

  /45

  $1,099,000

  • 3 Beds
  • 2 Baths
  • 1,488 Sq Ft

  27334 Guadaloupe Ln, Ramrod Key, FL 33042

  This waterfront home features impact windows and doors throughout, providing reliable security and peace of mind. Boating enthusiasts will appreciate the direct canal access with no bridges to open water, making it easy to head straight out for a day on the water. The canal-side setup includes a 30' long concrete dock, giving you a dedicated spot to tie up your boat right behind the

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  27334 Guadaloupe Ln, Ramrod Key, FL 33042
• 

  

  /20

  $4,588

  Total Monthly Price

  • 2 Beds
  • 2 Baths
  • 861 Sq Ft
  • Condo for Rent

  279 89th Street Ocean Unit SI ID1608678P, Marathon, FL 33050

  The advertised rate of $4,588/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 28, 2026. Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can

  279 89th Street Ocean Unit SI ID1608678P, Marathon, FL 33050
• 

  

  /45

  $1,550,000

  Sold Jan 30, 2026

  28538 John Silver Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 1981

  Last Sold Summary

  • 3% Below List Price
  • $1,242/SF
  • 164 Days On Market

  Current Estimated Value $1,532,219

  Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.

  28538 John Silver Rd, Summerland Key, FL 33042
• 

  /2

  Est $2,818,752

  Not Listed For Sale

  Unlisted Address

  • 4 Beds
  • 3.5 Baths
  • 2,662 Sq Ft
  • Built 2015

  Unlisted Address

  Last Sold Summary

  • 19 Days On Market

  Last Listing Agent Richard Capote Capote Global Realty LLC
• 

  

  /83

  $3,450,000

  • 5 Beds
  • 4 Baths
  • 3,244 Sq Ft

  69 Tingler Ln, Marathon, FL 33050

  This tropical Sombrero Beach 2-Home Compound is set on a spacious 17,600 sq ft fenced lot with Pool, 2 Tikis and located just 2 properties in from the ocean. Fantastic deep water boating access from the 97' dock with 2 Boat Lifts, 15,000 lbs and 3,000 lbs. . The main house features 2,540 sq. ft. with 3 Bedrooms, 3 Full Baths and a spacious living room with direct Pool views, cathedral

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  69 Tingler Ln, Marathon, FL 33050
• 

  

  /14

  $2,200

  Total Monthly Price

  • Studio
  • 1 Bath
  • 495 Sq Ft
  • Condo for Rent

  88500 Overseas Hwy Unit 433, Tavernier, FL 33070

  88500 Overseas Hwy Unit 433, Tavernier, FL 33070
• 

  

  /56

  $880,000

  Sold Apr 15, 2026

  82260 Overseas Hwy, Islamorada, FL 33036

  • 3 Beds
  • 3 Baths
  • 2,314 Sq Ft
  • Built 1964

  Last Sold Summary

  • 22% Below List Price
  • $380/SF
  • 276 Days On Market

  Current Estimated Value $935,485

  Last Listing Agent The Florida Keys Sold Sisters Ocean Sotheby's International Realty

  82260 Overseas Hwy, Islamorada, FL 33036
• 

  Not Listed For Sale

  91655 Overseas Hwy, Tavernier, FL 33070

  • Built 1976

  91655 Overseas Hwy, Tavernier, FL 33070

  Last Sold Summary

  • 40 Days On Market

  Last Listing Agent Grace Rodriguez AB Realty, LLC
• 

  

  /109

  $6,200,000

  • 5 Beds
  • 6 Baths
  • 4,401 Sq Ft

  1285 Coury Dr, Key Colony Beach, FL 33051

  Experience Mediterranean elegance and open-water living at this private oceanfront estate, featuring a pool, all set on a gated 10,545 sq. ft. lot in prestigious Key Colony Beach. Spanning 4,401 sq. ft., the 5 Bedroom, 4 Full and 2 Half Bath residence features impact glass and a private sandy beach offering privacy along the open water. Built for the ultimate boating lifestyle, the estate boasts

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  1285 Coury Dr, Key Colony Beach, FL 33051
• 

  

  /23

  $3,900

  Total Monthly Price

  • 3 Beds
  • 2 Baths
  • 1,392 Sq Ft
  • Townhouse for Rent

  596 W Shore Dr, Summerland Key, FL 33042

  Enjoy the laid-back Florida Keys lifestyle in this spacious downstairs 3-bedroom, 2-bath waterfront duplex located on beautiful Summerland Key. With approximately 1,392 square feet of living space, this home offers a comfortable, open layout in a convenient location near Key West, Big Pine Key, and Marathon.Inside, you'll find an open-concept living and dining area with plenty of room to

  596 W Shore Dr, Summerland Key, FL 33042
• 

  

  /71

  $2,250,000

  Sold Aug 31, 2026

  211 Bruce Ct, Marathon, FL 33050

  • 4 Beds
  • 5 Baths
  • 1,800 Sq Ft
  • Built 2019

  Last Sold Summary

  • 6% Below List Price
  • $1,250/SF
  • 16 Days On Market

  Current Estimated Value $2,384,488

  Last Listing Agent Katie Carrillo LPT Realty, LLC

  211 Bruce Ct, Marathon, FL 33050
• 

  

  /42

  Est $1,459,509

  Not Listed For Sale

  118 S Layton Dr, Long Key, FL 33001

  • 3 Beds
  • 3 Baths
  • 1,560 Sq Ft
  • Built 1981

  118 S Layton Dr, Long Key, FL 33001

  Last Sold Summary

  • 44 Days On Market

  Last Listing Agent AJ Vetter Palm House Real Estate
• 

  

  /50

  $1,149,000

  • 3 Beds
  • 2.5 Baths
  • 1,320 Sq Ft

  7044 Harbor Village Dr, Marathon, FL 33050

  Experience the best of the Duck Key lifestyle in this beautifully updated 3-bedroom, 2.5-bath waterfront villa at the world-renowned Hawks Cay Resort. INCLUDES BOAT SLIP. Offering 1,320 square feet of living space, a metal roof, impact-resistant windows and doors, and a deeded 35-foot boat slip directly behind the residence, this property combines effortless waterfront living with exceptional

  

  Coby Taylor

  Expert Realty LLC (HQ)

  7044 Harbor Village Dr, Marathon, FL 33050
• 

  

  /10

  $3,300

  Total Monthly Price

  • 2 Beds
  • 1 Bath
  • 960 Sq Ft
  • House for Rent

  563 49th St, Marathon, FL 33050

  Escape to year-round paradise in this charming 2-bedroom, 1-bathroom canal-front half duplex in Marathon, Florida Keys! Offering tranquil waterfront views and a private 24-foot dock, this cozy retreat is perfect for boating enthusiasts, anglers, or anyone seeking a relaxed tropical lifestyle.Property Features:Bedrooms: 2 | Bathrooms: 1 | Sleeps: 6Waterfront Living: Screened-in

  563 49th St, Marathon, FL 33050
• 

  

  /32

  $950,000

  Sold Aug 13, 2026

  1129 Hawksbill Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,150 Sq Ft
  • Built 1984

  Last Sold Summary

  • 1% Below List Price
  • $826/SF
  • 3 Days On Market

  Current Estimated Value $964,524

  Last Listing Agent Sean Farrer Coldwell Banker Schmitt Real E

  1129 Hawksbill Ln, Summerland Key, FL 33042
• 

  

  /60

  Est $980,067

  Not Listed For Sale

  40 Florida Dr, Key Largo, FL 33037

  • 4 Beds
  • 3 Baths
  • 2,116 Sq Ft
  • Built 2010

  40 Florida Dr, Key Largo, FL 33037

  Last Sold Summary

  • 69 Days On Market

  Last Listing Agent Lorie Leal American Caribbean Real Estate, Christie's International Real Estate

Showing Results 121 - 160, Page 4 of 18