65,787

Monroe County, FL Homes

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  • /16

    $245,000

    $5K PRICE DROP
    • Land
    • 871 Sq Ft
    • $12,250,000 per Acre

    1801 N Roosevelt M-28 Blvd, Key West, FL 33040

    LIVE IN PARADISE AFFORDABLE LIVEABOARD Houseboat & Slip! It's a TRUE KEY WEST LIFESTYLE... POF CASH ONLY! If your ready to enjoy life and have a crash pad in the Florida Keys, then come and see this one. 2018 Aqua Lodge Catamaran Houseboat 12'X42 2' Draft Molded Pontoon, FRP Hull No Motors, No batteries 50-amp shore service connection with pump out included with slip Fee $830 a month, parking,

    Agent Photo

    Annie Rivera

    Berkshire Hathaway Florida Realty

    1801 N Roosevelt M-28 Blvd, Key West, FL 33040
  • /5

    $1,650 Per Month

    • 1 Bed
    • 1 Bath
    • 434 Sq Ft
    • Condo for Rent

    1411 Truman Ave, Key West, FL 33040

    WE ENCOURAGE ALL INTERESTED PARTIES TO CALL OUR OFFICE PHONE DIRECTLY FOR THE FASTEST ANSWER AND ASSISTANCE WITH THIS LISTING. Application required prior to scheduling a showing. Available September 10th. Steeped in rich island history and radiating classic Conch charm offers a rare opportunity to own a piece of Old Town Key West paradise. Nestled in the highly coveted and peaceful neighborhood

    Maria Ottinger Maria Ottinger R.E Broker

    1411 Truman Ave, Key West, FL 33040
  • /61

    $1,400,000

    Sold Jan 28, 2026

    5669 Man o War Dr, Marathon, FL 33050

    • 4 Beds
    • 3 Baths
    • 2,312 Sq Ft
    • Built 1973

    Last Sold Summary

    • 44% Below List Price
    • $606/SF
    • 236 Days On Market

    Current Estimated Value $1,484,309

    Last Listing Agent Sam Williams Coldwell Banker Schmitt Real Estate Co.

    5669 Man o War Dr, Marathon, FL 33050
    • /36

      Est $905,406

      Not Listed For Sale

      3666 S Seas St, Big Pine Key, FL 33043

      • 2 Beds
      • 2 Baths
      • 1,519 Sq Ft
      • Built 1988
      3666 S Seas St, Big Pine Key, FL 33043

      Last Sold Summary

      • 89 Days On Market

  • /59

    $940,000

    $20K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 1,540 Sq Ft

    94825 Overseas Hwy Unit 281, Key Largo, FL 33037

    BUYERS -- A Rare Opportunity Awaits!If traditional bank financing isn't an option but you do have the means to purchase, this is your moment. With 30% down and verifiable income to support monthly payments, you can secure a beautiful home in one of the most desirable communities in the Florida Keys. Owner Financing Available.Welcome to Key Largo Ocean Resort (KLOR)--a vibrant, gated oceanfront

    Agent Photo

    Joe Vigo, P.A.

    RE/MAX All Keys Real Estate

    94825 Overseas Hwy Unit 281, Key Largo, FL 33037
  • /36

    $2,750 Per Month

    • 2 Beds
    • 1 Bath
    • 776 Sq Ft
    • Apartment for Rent

    5301 Ocean Terrace Unit 7, Marathon, FL 33050

    Turnkey island getaway in the heart of Marathon! This charming 2 bedroom, 1bath home comes fully furnished and ready for immediate enjoyment. HOA redid all the piping throughout the building, HOA includes pool usage and Boat slips of 28ft. Come see this unit today and enjoy the outdoor area with an amazing canal view. Conveniently located just minutes from Sombrero Beach and major shopping

    Marilys Grau Realty One Group Evolution

    5301 Ocean Terrace Unit 7, Marathon, FL 33050
  • /25

    $1,550,000

    Sold Dec 01, 2025

    1311 Pine St, Key West, FL 33040

    • 3 Beds
    • 2.5 Baths
    • 1,368 Sq Ft
    • Built 1938

    Last Sold Summary

    • 3% Below List Price
    • $1,133/SF
    • 13 Days On Market

    Current Estimated Value $1,639,292

    Last Listing Agent Sabrina Acevedo Internet Realty of the Florida Keys Inc

    1311 Pine St, Key West, FL 33040
    • /20

      Est $180,880

      Not Listed For Sale

      100 Avenue I Unit 19, Marathon, FL 33050

      • 1 Bed
      • Built 1987
      100 Avenue I Unit 19, Marathon, FL 33050

      Last Sold Summary

      • 31 Days On Market

  • /15

    $895,000

    • Land
    • 14,374 Sq Ft
    • $2,712,121 per Acre

    30988 Witters Ln, Big Pine Key, FL 33043

    Build Immediately with Active Building & Pool Permits Included. This Bay Front/Gulf Front open-water lot offers 14,746 sq. ft. of waterfront opportunity with beautiful wide water views, sunrise exposure, and the rare advantage of moving forward without years of permitting uncertainty. Included are approved plans for an elevated CBS coastal residence featuring 4 bedrooms, 4.5 bathrooms, parking

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real E

    30988 Witters Ln, Big Pine Key, FL 33043
  • /13

    $2,900 Per Month

    • 2 Beds
    • 2 Baths
    • 1,104 Sq Ft
    • House for Rent

    799 Hazel St, Key Largo, FL 33037

    This beautifully maintained 2-bedroom, 2-bathroom single-family home is now available for rent. Featuring all modern appliances and an elevator for easy accessibility, it’s the perfect fit for those with mobility needs. The spacious ground floor offers a relaxing outdoor area, ideal for family barbecues or enjoying sunsets by the peaceful canal that leads directly to the ocean. Full perimeter

    799 Hazel St, Key Largo, FL 33037
  • /3

    $510,000

    Sold Jun 18, 2026

    57 Pelican Ln, Big Pine Key, FL 33043

    • 2 Beds
    • 2 Baths
    • 948 Sq Ft
    • Built 1990

    Last Sold Summary

    • 7% Below List Price
    • $538/SF
    • 23 Days On Market

    Current Estimated Value $545,931

    Last Listing Agent Elsa Machado Elsa Realty, LLC

    57 Pelican Ln, Big Pine Key, FL 33043
    • /47

      Est $1,274,267

      Not Listed For Sale

      1408 Johnson St Unit A & B, Key West, FL 33040

      • 3 Beds
      • 2 Baths
      • 1,344 Sq Ft
      • Built 1958
      1408 Johnson St Unit A & B, Key West, FL 33040

      Last Sold Summary

      • 100 Days On Market

  • /46

    $699,000

    $51K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,352 Sq Ft

    1001 W Ocean Dr Unit 2-201, Key Colony Beach, FL 33051

    Exquisitely appointed, spacious end-unit condo showcasing breathtaking ocean and pool view. This elegant residence features a sun-drenched open deck and a covered porch connecting the bedrooms, offering a seamless blend of comfort and coastal sophistication. With 1,352 square feet of beautifully designed interior space, the home provides both privacy and openness. The gourmet kitchen is equipped

    Agent Photo

    Lynn Goodwin

    Coldwell Banker Schmitt Real Estate Co.

    1001 W Ocean Dr Unit 2-201, Key Colony Beach, FL 33051
  • /11

    $2,400 Per Month

    • 3 Beds
    • 1 Bath
    • 990 Sq Ft
    • House for Rent

    1702 Bertha St, Key West, FL 33040

    Welcome to this charming three-bedroom, one-bathroom single-story residence located in the West subdivision of Key West, Florida. Offering 990 square feet of finished living space, this home provides comfortable, efficient layout across one floor for practical everyday living. The thoughtful design accommodates multiple bedrooms while maintaining an intimate footprint, making it an excellent

    1702 Bertha St, Key West, FL 33040
  • /65

    $4,000

    Sold Jul 06, 2026

    30361 Hardin Rd, Big Pine Key, FL 33043

    • 3 Beds
    • 2 Baths
    • 888 Sq Ft
    • Built 1963

    Last Sold Summary

    • 20% Below List Price
    • $5/SF
    • 79 Days On Market

    Current Estimated Value $803,670

    Last Listing Agent Maris Delgado LoKation Real Estate - Key Largo

    30361 Hardin Rd, Big Pine Key, FL 33043
    • /11

      Not Listed For Sale

      452 50th St, Marathon, FL 33050

      • 4 Beds
      • 2 Baths
      • 2,064 Sq Ft
      • Built 1959
      452 50th St, Marathon, FL 33050

      Last Sold Summary

      • 97 Days On Market

  • /14

    $3,400

    Pending
    • 2 Beds
    • 1.5 Baths
    • 780 Sq Ft

    32 Merganser Ln, Key West, FL 33040

    Discover your perfect long-term rental in the heart of Key West Golf Club! This charming 780 sqft property offers an ideal blend of comfort and convenience, perfect for those looking to embrace the vibrant lifestyle of this tropical haven. For some work distances it is 2.5 miles from Naval Air Station Boca Chica, 5.1 miles from US Coast Guard Sector Key West Trumbo Point, 6.1 miles from JIATF

    Agent Photo

    Darrin Smith

    Key West Luxury Real Estate Inc (KW)

    32 Merganser Ln, Key West, FL 33040
  • /27

    $2,850 Per Month

    • 2 Beds
    • 1.5 Baths
    • 989 Sq Ft
    • Condo for Rent

    87455 Old Hwy 245 Hwy Unit 245, Plantation Key, FL 33036

    Location! Location! Location! Beautiful 2 bedroom 2 bath furnished condo. Located in oceanfrontbuilding in Islamorada. Dock available for boat to load and unload. Elevator to first floor. Master has a large balcony and walk in closet. Additional storage unit on main floor. Covered parking, guest parking, heated pool, 400 ft. fishing pier/dock for loading and unloading only, club house, gym,

    Anthony Garcia The Keyes Company

    87455 Old Hwy 245 Hwy Unit 245, Plantation Key, FL 33036
  • /12

    $155,000

    Sold May 29, 2026

    7025 Shrimp Rd, Key West, FL 33040

    • Land
    • 0 Sq Ft

    Last Sold Summary

    • 8% Below List Price
    • 18 Days On Market

    Last Listing Agent Randy Moss Coldwell Banker Schmitt RE Co

    7025 Shrimp Rd, Key West, FL 33040
    • /31

      Not Listed For Sale

      396 50th St, Marathon, FL 33050

      • 5 Beds
      • 2 Baths
      • 1,896 Sq Ft
      • Built 1959
      396 50th St, Marathon, FL 33050

      Last Sold Summary

      • 97 Days On Market

  • /30

    $325,000

    $4K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 860 Sq Ft

    1129 Pebble Beach Ln Unit 12, Marathon, FL 33050

    You don't often hear 'affordable' and 'Duck Key' in the same sentence, but this top-floor end unit proves you can live on one of the Keys' most desirable islands without breaking the bank. The end-unit location means extra windows that flood the space with natural light, and your private patio is the perfect spot to unwind at the end of the day. Inside you'll find tile floors throughout, a full

    Agent Photo

    Megan Jones

    Coldwell Banker Schmitt RE Co

    1129 Pebble Beach Ln Unit 12, Marathon, FL 33050
  • /17

    $4,550 Per Month

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Townhouse for Rent

    2515 Staples Ave Unit A, Key West, FL 33040

    Long Term Rental (1 year lease) Fully renovated and offered furnished (if desired), this villa-style half-duplex offers a spacious 3-bedroom, 2-bath layout with two entrances, W/D, a private Porch and Patio with lawn. The property is fully enclosed with high-quality fencing, creating privacy, lovely tropical landscaping and a clean, finished look throughout the property.Positioned along Key

    Michelle Blades Realty Executives Florida Keys Old Town

    2515 Staples Ave Unit A, Key West, FL 33040
  • /58

    $572,000

    Sold May 27, 2026

    175 E Cahill Ct, Big Pine Key, FL 33043

    • 2 Beds
    • 2 Baths
    • 1,008 Sq Ft
    • Built 1991

    Last Sold Summary

    • 5% Below List Price
    • $567/SF
    • 40 Days On Market

    Current Estimated Value $587,875

    Last Listing Agent Darlene Alferes Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

    175 E Cahill Ct, Big Pine Key, FL 33043
    • /15

      Est $314,229

      Not Listed For Sale

      21 Sombrero Blvd Unit 210, Marathon, FL 33050

      • 1 Bed
      • 1 Bath
      • 547 Sq Ft
      • Built 1986
      21 Sombrero Blvd Unit 210, Marathon, FL 33050

      Last Sold Summary

      • 14 Days On Market

  • /29

    $999,000

    $100K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,264 Sq Ft

    441 3rd St, Key Colony Beach, FL 33051

    This charming 3-bedroom, 2-bath half-duplex has so much to offer! Watch stunning Keys sunsets from your screened porch, or dock your boat at the 30-foot slip with quick ocean access just around the corner. Stroll to the Cabana Club for pool and beach access down the street. The master suite features a king bed, a bath with a jetted tub, separate shower, double sinks, and a walk-in closet. The

    Agent Photo

    Karen Liskey

    Key Colony Beach Realty

    441 3rd St, Key Colony Beach, FL 33051
  • /6

    $1,800 Per Month

    • 1 Bed
    • 1 Bath
    • 1,971 Sq Ft
    • Apartment for Rent

    169 Corrine Place, Key Largo, FL 33037

    Beautifully renovated 1-bedroom, 1-bathroom downstairs apartment located in the heart of Key Largo. This bright and modern unit has been fully updated with new finishes throughout and has been meticulously maintained, offering a clean, comfortable place to call home. The apartment features an open and functional layout, a fully updated kitchen and bathroom, and the convenience of a private

    Kenneth Smith American Caribbean Real Estate, Christie's International Real Estate

    169 Corrine Place, Key Largo, FL 33037
  • /38

    $790,000

    Sold May 22, 2026

    30471 Coconut Hwy, Big Pine Key, FL 33043

    • 3 Beds
    • 2 Baths
    • 1,513 Sq Ft
    • Built 1959

    Last Sold Summary

    • 14% Below List Price
    • $522/SF
    • 319 Days On Market

    Current Estimated Value $785,638

    Last Listing Agent Richard Haskins Buy The Keys

    30471 Coconut Hwy, Big Pine Key, FL 33043
    • /50

      Est $718,968

      Not Listed For Sale

      88540 Overseas & Boat Slip #3 Hwy Unit 605, Plantation Key, FL 33070

      • 2 Beds
      • 2 Baths
      • 853 Sq Ft
      • Built 1985
      88540 Overseas & Boat Slip #3 Hwy Unit 605, Plantation Key, FL 33070

      Last Sold Summary

      • 29 Days On Market

  • /35

    $1,250,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 2,052 Sq Ft

    227 Atlantic Blvd, Key Largo, FL 33037

    So many possibilities here with the Suburban Commercial zoning .The large home has a newer metal roof and impact windows with newer appliances. Large Corner lot (16,200 sqft.) that is completely fenced with mature fruit trees and a separate storage building. Located in the hub of central Key Largo near shopping, medical offices and Key Largo Community Park. Previously used as professional office

    Agent Photo

    Tom Rodriguez

    American Caribbean Real Estate, Christie's International Real Estate

    227 Atlantic Blvd, Key Largo, FL 33037
  • /10

    $1,550 Per Month

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

    21857 Disturbed Pine Rd, Summerland Key, FL 33042

    Welcome to this charming single-story residence located in the Cudjoe Acres community of Cudjoe Key, Florida. This two-bedroom, one-bathroom home offers 415 square feet of finished living space, providing an efficient and manageable floor plan. The property includes a one-car garage, adding convenient storage and protection for your vehicle. Situated in Cudjoe Acres, this residence presents an

    21857 Disturbed Pine Rd, Summerland Key, FL 33042
  • /24

    $2,362,000

    Sold Apr 14, 2026

    506 Emma St, Key West, FL 33040

    • 3 Beds
    • 3 Baths
    • 1,608 Sq Ft
    • Built 1994

    Last Sold Summary

    • 5% Below List Price
    • $1,469/SF
    • 27 Days On Market

    Current Estimated Value $2,407,459

    Last Listing Agent Wendy Zintsmaster Truman & Co. (KW)

    506 Emma St, Key West, FL 33040
    • /50

      Est $1,333,580

      Not Listed For Sale

      96000 Overseas Hwy Unit EE23 + 35' boat slip, Key Largo, FL 33037

      • 2 Beds
      • 2 Baths
      • 1,400 Sq Ft
      • Built 1972
      96000 Overseas Hwy Unit EE23 + 35' boat slip, Key Largo, FL 33037

      Last Sold Summary

      • 136 Days On Market

  • /97

    $1,199,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,522 Sq Ft

    17151 Marlin Dr, Sugarloaf Key, FL 33042

    This beautifully remodeled waterfront bungalow is nestled in the heart of Sugarloaf Shores ,one of the Lower Florida Keys' most desirable boating communities. Set on an expansive 12,500 sq ft lot surrounded by lush tropical landscaping, this elevated two-story home offers the perfect blend of privacy, comfort, and island charm. With 3 Bedrooms plus a Loft and 2 Bathrooms, the layout is

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    17151 Marlin Dr, Sugarloaf Key, FL 33042
  • /55

    $6,000 Per Month

    • 4 Beds
    • 3 Baths
    • 1,080 Sq Ft
    • House for Rent

    115 Harbor Ln, Tavernier, FL 33070

    Welcome to this canal-front home in Kahiki Harbor, offering protected dockage and quick access to both the Atlantic Ocean and Florida Bay via Tavernier Creek. The elevated living area opens to a spacious covered porch overlooking the water, creating the perfect setting to relax and enjoy the Florida Keys lifestyle. And the downstairs adds extra living space perfect for guests or extended family.

    Caroline Anthony Palm House Real Estate

    115 Harbor Ln, Tavernier, FL 33070
  • /52

    $2,350,000

    Sold Mar 13, 2026

    101 Villa Bella Dr, Islamorada, FL 33036

    • 2 Beds
    • 2 Baths
    • 1,560 Sq Ft
    • Built 1986

    Last Sold Summary

    • 15% Below List Price
    • $1,506/SF
    • 71 Days On Market

    Current Estimated Value $2,392,421

    Last Listing Agent Alina Davis Coldwell Banker Schmitt Islamorada

    101 Villa Bella Dr, Islamorada, FL 33036
    • /58

      Est $765,029

      Not Listed For Sale

      1133 W Ocean Dr Unit 5, Key Colony Beach, FL 33051

      • 3 Beds
      • 3 Baths
      • 1,929 Sq Ft
      • Built 1982
      1133 W Ocean Dr Unit 5, Key Colony Beach, FL 33051

      Last Sold Summary

      • 42 Days On Market

  • /32

    $599,000

    $26K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,032 Sq Ft

    3205 Pearl Ave, Key West, FL 33040

    Located in one of Key West's most desirable townhome communities, this inviting residence offers comfort, flexibility, and value — all with no HOA and no monthly fees. The main level features a full bathroom with a shower, along with washer and dryer conveniently located on the outside porch. The living area flows seamlessly into a well-sized kitchen and dining space, creating an easy and

    Agent Photo

    Miriam Novotny

    Compass Florida, LLC

    3205 Pearl Ave, Key West, FL 33040
  • /49

    $5,800 Per Month

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • House for Rent

    3770 Park Ave, Big Pine Key, FL 33043

    Welcome to Caribbean Cove located in Big Pine Key. Located in the lower keys, 30 minutes from Key West. This stunning waterfront three bedroom/two bath home features an open floor plan, with a fully furnished living area and a modern kitchen. The kitchen is a culinary dream, equipped with stainless steel appliances and an oversized quartz island, surrounded by eight comfortable seats, perfect for

    Mary Jo Selden DomainRealty.com LLC

    3770 Park Ave, Big Pine Key, FL 33043
  • /51

    $535,000

    Sold Feb 10, 2026

    300 3rd St, Key Colony Beach, FL 33051

    • 2 Beds
    • 2 Baths
    • 1,031 Sq Ft
    • Built 1982

    Last Sold Summary

    • 4% Below List Price
    • $519/SF
    • 35 Days On Market

    Current Estimated Value $546,039

    Last Listing Agent Karen Raspe, PA Ocean Sotheby's International

    300 3rd St, Key Colony Beach, FL 33051
    • /8

      Not Listed For Sale

      30 Avenue F, Key Largo, FL 33037

      • 2 Beds
      • 1.5 Baths
      • 840 Sq Ft
      • Built 1984
      30 Avenue F, Key Largo, FL 33037

      Last Sold Summary

      • 2 Days On Market

Showing Results 401 - 440, Page 11 of 18

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