65,633

Monroe County, FL Homes

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  • /45

    $799,000

    • 2 Beds
    • 2 Baths
    • 1,216 Sq Ft

    3715 Flagler Ave, Key West, FL 33040

    Welcome to this charming 2-bedroom, 2-bath Conch house offering 1,216 sq. ft. of comfortable living space in one of Key West's most convenient locations. The home is filled with warmth and character, highlighted by vaulted wood ceilings with exposed beams that create an inviting coastal atmosphere. Natural light pours through the impact windows and full wall of sliding glass doors, while the

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    3715 Flagler Ave, Key West, FL 33040
  • /19

    $2,500 Per Month

    • Studio
    • 1 Bath
    • 587 Sq Ft
    • Furnished Studio Apartment in Old Town

    327 Margaret St, Key West, FL 33040

    Beautiful second floor studio for two on the second floor of the historic Sailmaker's House. - Incredible location in Historic Old Town!This property is located 1.5 blocks from the Historic Seaport and 4.5 blocks from Duval Street.The open floor plan maximizes the space in this airy tree top studio. Comfortable Queen size bed will inspire sweet dreams and the large built

    327 Margaret St, Key West, FL 33040
  • /4

    $515,000

    Sold Apr 16, 2026

    3930 S Roosevelt Blvd Unit E104, Key West, FL 33040

    • 3 Beds
    • 2 Baths
    • 1,062 Sq Ft
    • Built 1991

    Last Sold Summary

    • 11% Below List Price
    • $485/SF
    • 229 Days On Market

    Current Estimated Value $518,538

    Last Listing Agent Ted Stewart Truman & Co. (KW)

    3930 S Roosevelt Blvd Unit E104, Key West, FL 33040
    • /34

      Not Listed For Sale

      135 Dorsett Dr, Marathon, FL 33050

      • 3 Beds
      • 2 Baths
      • 1,191 Sq Ft
      • Built 2025
      135 Dorsett Dr, Marathon, FL 33050

      Last Sold Summary

      • 38 Days On Market

  • /61

    $1,250,000

    • 2 Beds
    • 2 Baths
    • 1,119 Sq Ft

    1911 Seidenberg Ave, Key West, FL 33040

    With only two owners in its history, this well-maintained two-story property presents a rare investment opportunity in Key West. Configured as a legal duplex with two separately metered 1-bedroom, 1-bath units, it offers exceptional flexibility--ideal for investors seeking strong rental potential, business owners looking for employee housing, or owner-occupants wanting to offset costs by renting

    Agent Photo

    Everett Smith

    Ocean Sotheby's International Realty

    1911 Seidenberg Ave, Key West, FL 33040
  • /26

    $2,850 Per Month

    • 2 Beds
    • 1.5 Baths
    • 1,000 Sq Ft
    • Condo for Rent

    87465 Old Hwy 209 Hwy Unit 209, Plantation Key, FL 33036

    LIVE THE DREAM IN THIS OCEANFRONT RESORT STYLE PROPERTY ON MILLIONAIRES' ROW IN PLANTATION BY THE SEA! LOCATED IN ISLAMORADA IN THE BEAUTIFUL FLORIDA KEYS! TURN KEY STUNNING AND REMODELED, FULLY FURNISHED 2 BEDROOM 1.5 BATH CONDO IS MOVE IN READY! ALL YOU NEED ARE YOUR CLOTHES AND TOOTHBRUSH! GLASSWARE, STEMWARE, SHEETS, TOWELS, ALL ARE FURNISHED FOR YOU! BEAUTIFUL OPEN CONCEPT KITCHEN HAS A

    Anthony Garcia The Keyes Company

    87465 Old Hwy 209 Hwy Unit 209, Plantation Key, FL 33036
  • /6

    $1,937,500

    Sold Jun 05, 2026

    1058 Buttonwood Dr E, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,767 Sq Ft
    • Built 2001

    Last Sold Summary

    • $1,096/SF
    • 0 Days On Market

    Current Estimated Value $1,589,567

    Last Listing Agent Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty

    1058 Buttonwood Dr E, Summerland Key, FL 33042
    • /47

      Not Listed For Sale

      88 2nd Ct, Key Largo, FL 33037

      • 2 Beds
      • 1.5 Baths
      • 984 Sq Ft
      • Built 1968
      88 2nd Ct, Key Largo, FL 33037

      Last Sold Summary

      • 16 Days On Market

  • /46

    $315,000

    $74K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 885 Sq Ft

    55 Boca Chica Rd Unit 85, Key West, FL 33040

    Motivated Seller. Updated and ready for you. This 2 Br/1 Bath unit is spacious and now looks like a million dollars! Fresh paint throughout, new floors in DR, Kitchen, bedrooms & bath, new plumbing and water heater, new bath vanity. The spacious Florida Room is the place to be, it invites you to relax, get comfortable and enjoy the day or evening. Check the Document Tab above and see much more

    Agent Photo

    Margarita Villoch

    Island Group Realty (KW)

    55 Boca Chica Rd Unit 85, Key West, FL 33040
  • /16

    $2,625 Per Month

    • 1 Bed
    • 1 Bath
    • Old Town Location - 1 bed / 1 bath Apartment

    725 Southard St, Key West, FL 33040

    Welcome to this great Old Town Location, a charming 1 bed / 1 bath apartment nestled in the heart of Key West. This cozy and well-maintained home offers a convenient and desirable location. Step inside and discover a thoughtfully designed living space that includes a stove, refrigerator, AC Mini Splits, washer/dryer, microwave, and a private deck. With its prime location, you'll have easy access

    725 Southard St, Key West, FL 33040
  • /30

    $930,000

    Sold Aug 01, 2025

    608 Roberts Ln, Key West, FL 33040

    • 2 Beds
    • 2 Baths
    • 1,700 Sq Ft
    • Built 1933

    Last Sold Summary

    • 41% Below List Price
    • $547/SF
    • 189 Days On Market

    Current Estimated Value $1,089,609

    Last Listing Agent Bascom Grooms Bascom Grooms Real Estate (KW)

    608 Roberts Ln, Key West, FL 33040
    • /36

      Not Listed For Sale

      88540 Overseas Hwy Unit 106 and boat sl, Tavernier, FL 33070

      • 3 Beds
      • 2 Baths
      • 1,271 Sq Ft
      • Built 1985
      88540 Overseas Hwy Unit 106 and boat sl, Tavernier, FL 33070

      Last Sold Summary

      • 12 Days On Market

  • /45

    $1,155,000

    • 3 Beds
    • 2 Baths
    • 984 Sq Ft

    17183 Green Turtle Ln W, Summerland Key, FL 33042

    Live on the water on one of the largest lots in Sugarloaf Shores, fronting a 70 ft wide crystal clear swimming canal with easy ocean access. Recent upgrades make this home truly turnkey, including a new seawall, a new boat lift 15,000 lbs), and a newer roof. The big ticket items are already done for you.The grounds are the professionally landscaped with mature trees, fruit trees, a custom

    Agent Photo

    Dan Serban

    Key West Luxury Real Estate Inc (KW)

    17183 Green Turtle Ln W, Summerland Key, FL 33042
  • /30

    $3,800 Per Month

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

    95401 Overseas Hwy, Key Largo, FL 33037

    Available July 15th! Fully furnished and renovated, this tropical Keys retreat offers the perfect blend of fun and functionality. Located at MM 95 Oceanside, right on the Overseas Highway, you'll enjoy front-row access to Key Largo's best restaurants, sandbars, and outdoor activities. The fully fenced property provides privacy and ample space to park your boat, RV, or water toys, with access to a

    Lizzet Torres One Family Realty, LLC

    95401 Overseas Hwy, Key Largo, FL 33037
  • /40

    $3,500,000

    Sold May 06, 2026

    59720 Overseas Hwy Unit 13, Marathon, FL 33050

    • 5 Beds
    • 4.5 Baths
    • 3,011 Sq Ft
    • Built 2023

    Last Sold Summary

    • 8% Below List Price
    • $1,162/SF
    • 835 Days On Market

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

    59720 Overseas Hwy Unit 13, Marathon, FL 33050
    • /22

      Est $512,677

      Not Listed For Sale

      31232 Ave d, Big Pine Key, FL 33043

      • 3 Beds
      • 1 Bath
      • 988 Sq Ft
      • Built 1958
      31232 Ave d, Big Pine Key, FL 33043

      Last Sold Summary

      • 41 Days On Market

  • /58

    $979,000

    $30K PRICE INCREASE
    • 3 Beds
    • 2 Baths
    • 1,872 Sq Ft

    27358 Jamaica Ln, Summerland Key, FL 33042

    Discover the laid-back waterfront lifestyle you've been dreaming of at this charming canal-front home in Breezeswept Beach Estates on Ramrod Key. Perfectly situated with water on 2 sides this property offers 150' of waterfront including a deep water basin, excellent dockage and easy access for boating, fishing, kayaking, or paddle boarding right from your backyard. Offering a flexible floor plan

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    27358 Jamaica Ln, Summerland Key, FL 33042
  • /26

    $4,500 Per Month

    • 4 Beds
    • 1.5 Baths
    • 1,176 Sq Ft
    • NEW PRICE!! Move in Ready Single Family Home - 4 bedroom - 1.5 Bathroom on Stock Island

    H16 Miriam St, Key West, FL 33040

    Great Family Home Located on Stock Island with water view. This unfurnished single-family 4 bed / 2 - half baths plus adjoining tub/shower stilt home offers central AC, washer/dryer, ample off street parking and fully fenced yard. All pets welcome! $5,200.00/mo plus utilities. Available mid-June for a 12 month rental. First/Last/Security. At Historic Key West Annual Rentals, we strive to

    H16 Miriam St, Key West, FL 33040
  • /76

    $1,600,000

    Sold Jul 22, 2026

    2819 Fogarty Ave, Key West, FL 33040

    • 3 Beds
    • 3 Baths
    • 1,651 Sq Ft
    • Built 1958

    Last Sold Summary

    • 3% Above List Price
    • $969/SF
    • 9 Days On Market

    Current Estimated Value $1,506,091

    Last Listing Agent NON-MLS MEMBER MAR NON MLS MEMBER

    2819 Fogarty Ave, Key West, FL 33040
    • /44

      Est $664,993

      Not Listed For Sale

      663 50th Ct Gulf, Marathon, FL 33050

      • 2 Beds
      • 2 Baths
      • 1,086 Sq Ft
      • Built 1985
      663 50th Ct Gulf, Marathon, FL 33050

      Last Sold Summary

      • 25 Days On Market

  • /10

    $499,000

    • Land
    • 14,706 Sq Ft
    • $1,478,066 per Acre

    63 Sugarloaf Dr, Sugarloaf Key, FL 33042

    Welcome to the lowest priced waterfront lot with an active building permit on prestigious Sugarloaf Key. This oversized 14,706 sq. ft. canal-front property features no-bridge ocean access, granting you instant entry to world-class fishing, diving, and boating. Located in the premier residential enclave of the Sugarloaf Shores, this lot includes an active building permit for a custom 2,120 sq.

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    63 Sugarloaf Dr, Sugarloaf Key, FL 33042
  • /41

    $7,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,068 Sq Ft
    • House for Rent

    280 Airport Dr S, Summerland Key, FL 33042

    *** Private Airstrip *** Welcome to your slice of paradise in the Florida Keys! For aviation enthusiasts, the allure of this property is further enhanced by its location within a private airpark community (FD51 Summerland Key Airport). Nestled on a serene, clear wide canal with direct access to the Atlantic Ocean with no bridges, within a private airpark community, this home offers the

    Lisa Guirguis Genesis Realty Team

    280 Airport Dr S, Summerland Key, FL 33042
  • /6

    $600,000

    Sold Dec 01, 2025

    101551 Overseas Hwy Unit 57, Key Largo, FL 33037

    • Land
    • 2,085 Sq Ft
    • $12,535,252 per Acre

    Last Sold Summary

    • 5% Below List Price
    • 8 Days On Market

    Current Estimated Value $594,042

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

    101551 Overseas Hwy Unit 57, Key Largo, FL 33037
    • /45

      Est $1,825,423

      Not Listed For Sale

      23066 Tarpon Ln, Summerland Key, FL 33042

      • 4 Beds
      • 3.5 Baths
      • 1,938 Sq Ft
      • Built 2025
      23066 Tarpon Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 65 Days On Market

  • /51

    $459,000

    • 1 Bed
    • 1 Bath
    • 577 Sq Ft

    500 Burton Dr Unit 2304, Tavernier, FL 33070

    Least expensive Condo at OP, this 1/1 has Impact windows and sliders with a nice Ocean view.Enjoy the direct Ocean Access Marina, Jr. Olympic pool and 14 person spa, Private Oceanfront Cafe & Lounge, Nice beach area with Tiki's , Lighted Pickle ball & Tennis courts. Boats have to be under 28ft and insured. Owners may rent their place or live here full time and Homestead their OP condo. OP is

    Agent Photo

    Tom Rodriguez

    American Caribbean Real Estate, Christie's International Real Estate

    500 Burton Dr Unit 2304, Tavernier, FL 33070
  • /22

    $14,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,700 Sq Ft
    • Condo for Rent

    918 Southard St Unit 205, Unit 205, Key West, FL 33040

    Art-Filled 1,700SF 3BR/2BA Old Town Key West Home with 2 Decks, Pool, ParkingLarge art-filled, two story Key West condo boasts 2 large inviting bedrooms, including a king bed, queen bed, and large office or third bedroom for extra flexibility. Guests enjoy living and dining rooms, 2 full bathrooms, one with a large shower and one with bathtub, high ceilings throughout, wrap around porch in lush

    918 Southard St Unit 205, Unit 205, Key West, FL 33040
  • /20

    $865,000

    Sold Feb 24, 2026

    102 Snapper Creek Dr, Layton, FL 33001

    • 3 Beds
    • 2 Baths
    • 1,056 Sq Ft
    • Built 2005

    Last Sold Summary

    • 6% Below List Price
    • $819/SF
    • 72 Days On Market

    Current Estimated Value $866,600

    Last Listing Agent Alberto Martinez Keller Williams Capital Realty

    102 Snapper Creek Dr, Layton, FL 33001
    • /66

      Est $797,522

      Not Listed For Sale

      313 Bayview Ave, Key Largo, FL 33037

      • 3 Beds
      • 3 Baths
      • 990 Sq Ft
      • Built 1999
      313 Bayview Ave, Key Largo, FL 33037

      Last Sold Summary

      • 62 Days On Market

  • /50

    $2,400,000

    $2M PRICE INCREASE
    • 3 Beds
    • 2.5 Baths
    • 3,172 Sq Ft

    317 E Seaview Cir, Duck Key, FL 33050

    Welcome to this stunning 3 bedroom, 2.5 bathroom, 3 story home on the quiet ocean side of Duck Key's exclusive Yacht Club Island. The beautifully landscaped grounds and resort style pool area set the tone from the moment you arrive. A beautiful metal spiral staircase connects each level, leading you to the top floor where an open concept kitchen, half bath, and living room are wrapped in windows

    Agent Photo

    Joseph Suarez

    Trustpoint Realty, LLC

    317 E Seaview Cir, Duck Key, FL 33050
  • /15

    $4,800 Per Month

    • 2 Beds
    • 2 Baths
    • 1,281 Sq Ft
    • House for Rent

    225 W 2nd Ct, Key Largo, FL 33037

    WATERFRONT in KEY LARGO Welcome to your Key Largo escape. This canal/waterfront charmer offers the perfect blend of comfort, coastal charm, and effortless entertaining — available for select summer and fall months. Inside, you'll find 2 bedrooms, 2 full bathrooms, generous living space, and a roomy kitchen designed for easy everyday living. The home feels bright, relaxed, and comfortable, making

    225 W 2nd Ct, Key Largo, FL 33037
  • /22

    $1,275,000

    Sold Feb 09, 2026

    56 Pelican Rd, Marathon, FL 33050

    • 2 Beds
    • 1 Bath
    • 864 Sq Ft
    • Built 1968

    Last Sold Summary

    • 20% Below List Price
    • $1,476/SF
    • 382 Days On Market

    Current Estimated Value $1,613,189

    Last Listing Agent Valeria Perez Trust Invest Real Estate Corp

    56 Pelican Rd, Marathon, FL 33050
    • /18

      Est $274,806

      Not Listed For Sale

      325 Calusa St Unit 426, Key Largo, FL 33037

      325 Calusa St Unit 426, Key Largo, FL 33037

      Last Sold Summary

      • 39 Days On Market

  • /40

    $879,000

    $16K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,296 Sq Ft

    205 Humpty Dumpty Dr, Key Largo, FL 33037

    SELLER SAYS 'MAKE AN OFFER' Ocean views and direct ocean access! Here's your chance to own an oceanside property in Key Largo with over 44ft of concrete dockage on a beautiful, clean canal in Key Largo's well desired Wynken Blynken & Nod subdivision. The spacious double wide has been thoughtfully updated with tile floors, an open kitchen, large bedrooms with tons of closet space and two fully

    Agent Photo

    Lorie Leal

    American Caribbean Real Estate, Christie's International Real Estate

    205 Humpty Dumpty Dr, Key Largo, FL 33037
  • /17

    $3,350 Per Month

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

    3655 Seaside Dr Unit 423, Key West, FL 33040

    Available for annual lease starting August 1st, 2026, this 2 bedroom, 2 bathroom fourth-floor condo is located in the desirable SaltPonds community in Key West. The condo offers a comfortable split floor plan, with each bedroom featuring its own ensuite bathroom, making it ideal for privacy and convenience. The primary bedroom also includes a walk-in closet.Enjoy a peaceful view from the private

    3655 Seaside Dr Unit 423, Key West, FL 33040
  • /53

    $3,500,000

    Sold Aug 08, 2025

    407-415 Olivia St, Key West, FL 33040

    • 6 Beds
    • 5 Baths
    • 3,171 Sq Ft
    • Built 1964

    Last Sold Summary

    • 18% Below List Price
    • $1,104/SF
    • 134 Days On Market

    Current Estimated Value $3,623,389

    Last Listing Agent Brenda Donnelly Brenda Donnelly Real Estate LLC

    407-415 Olivia St, Key West, FL 33040
    • /16

      Est $512,045

      Not Listed For Sale

      9 7th St, Key Colony Beach, FL 33051

      • 2 Beds
      • 2 Baths
      • 885 Sq Ft
      • Built 1966
      9 7th St, Key Colony Beach, FL 33051

      Last Sold Summary

      • 0 Days On Market

  • /41

    $799,000

    Under Contract
    • 2 Beds
    • 2 Baths
    • 1,082 Sq Ft

    22822 Buccaneer Ln, Summerland Key, FL 33042

    SELLER ACCEPTING BACK-UP OFFERS: Discover your perfect boater's retreat in beautiful Cudjoe Key! This stilted 2-bedroom, 2-bathroom home is situated on a deep-water canal. Access to both the Atlantic and Gulf is easy and achievable in minutes, making it an ideal base for fishing, boating, and enjoying the Keys lifestyle. One of the home's standout features is its exceptional privacy. With no

    Agent Photo

    Cardenas & Krug Team

    Coastal Collection Real Estate Inc.

    22822 Buccaneer Ln, Summerland Key, FL 33042
  • /90

    $6,500 Per Month

    • 3 Beds
    • 2 Baths
    • 2,208 Sq Ft
    • House for Rent

    2 Snipe Rd, Key Largo, FL 33037

    ~ JUSTED REDUCED ~ Seasonal rental in Key Largo. Newly renovated 3-story home with a clean, modern design. This spacious property offers 3 bedrooms, 2 bathrooms, and waterfront canal access with dockage included in the rental price. As a corner lot, it provides parking. Each floor features large terraces ideal for enjoying the outdoors. The top level includes a second living/entertainment room,

    Ricky Kallabat Keller Williams Capital Realty

    2 Snipe Rd, Key Largo, FL 33037
  • /31

    $750,000

    Sold Oct 03, 2025

    1428 Virginia St, Key West, FL 33040

    • 4 Beds
    • 2 Baths
    • 2,236 Sq Ft
    • Built 1933

    Last Sold Summary

    • 16% Below List Price
    • $335/SF
    • 111 Days On Market

    Current Estimated Value $809,721

    Last Listing Agent Walt Lee Berkshire Hathaway HomeServices Knight & Gardner Realty

    1428 Virginia St, Key West, FL 33040
    • /26

      Est $253,545

      Not Listed For Sale

      701 Spanish Main Dr Unit 6, Cudjoe Key, FL 33042

      • Built 1978
      701 Spanish Main Dr Unit 6, Cudjoe Key, FL 33042

      Last Sold Summary

      • 74 Days On Market

Showing Results 321 - 360, Page 9 of 18

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