65,010

Monroe County, FL Homes

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  • /41

    $1,100,000

    • 1 Bed
    • 1 Bath
    • 594 Sq Ft

    914 Windsor Ln, Key West, FL 33040

    Located in the heart of Old Town Key West, 914 Windsor Lane is the quintessential Key West conch cottage that captures the island's timeless charm. Behind the classic white picket fence and vibrant turquoise front door awaits a thoughtfully updated 1-bedroom, 1-bath retreat blending historic character with modern comforts. Inside, vaulted cathedral ceilings, Dade County pine accents, quartz

    Agent Photo

    Emily Lombard

    Ocean Sotheby's International Realty

    (645) 229-8867

    914 Windsor Ln, Key West, FL 33040
  • /25

    $10,000 Per Month

    • 4 Beds
    • 2 Baths
    • 1,575 Sq Ft
    • House for Rent

    125 Gardenia St, Tavernier, FL 33070

    Experience luxury waterfront living in the heart of the Florida Keys! 4 bedrooms and 2 bathrooms. This stunning modern home offers sleek finishes, breathtaking canal views, and direct boating access. Enjoy the spacious outdoor entertainment area, complete with a private dock, lush synthetic turf, and a large jacuzzi—perfect for relaxing under the stars. The upper-level terrace provides an ideal

    Dahiana Rojas de Rojas Canvas Real Estate

    125 Gardenia St, Tavernier, FL 33070
  • /41

    $775,000

    Sold May 01, 2026

    22939 Privateer Dr, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,288 Sq Ft
    • Built 1988

    Last Sold Summary

    • $602/SF
    • 3 Days On Market

    Current Estimated Value $769,267

    Last Listing Agent Michelle Howerton Brenda Donnelly Real Estate LLC

    22939 Privateer Dr, Summerland Key, FL 33042
    • /42

      Est $1,641,704

      Not Listed For Sale

      3625 Sunrise Dr, Key West, FL 33040

      • 3 Beds
      • 2.5 Baths
      • 2,101 Sq Ft
      • Built 1950
      3625 Sunrise Dr, Key West, FL 33040

      Last Sold Summary

      • 194 Days On Market

  • /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

    (877) 517-4449

    1801 N Roosevelt M-28 Blvd, Key West, FL 33040
  • /33

    $2,950 Per Month

    • 4 Beds
    • 2 Baths
    • 1,998 Sq Ft
    • House for Rent

    235 Anne Bonny Dr, Key Largo, FL 33037

    Prime Pirates Cove waterfront living! Two private 2BR/1BA homes under one roof, each with full kitchen, washer/dryer, and screened patio. Three properties from open bay with stunning water views. Features include a 50-foot concrete dock, boat launch nearby, and a spectacular 1,000 sq. ft. rooftop deck perfect for entertaining or relaxing with panoramic vistas. Divided outdoor spaces give each

    Milena Wood Barrios and Associates Realty

    235 Anne Bonny Dr, Key Largo, FL 33037
  • /22

    $295,000

    Sold Oct 24, 2025

    201 Coppitt Rd Unit 102, Key West, FL 33040

    • 1 Bed
    • 1 Bath
    • 536 Sq Ft
    • Built 1974

    Last Sold Summary

    • $550/SF
    • 54 Days On Market

    Current Estimated Value $293,782

    Last Listing Agent Jimmy Lane Island Life Realty Experts

    201 Coppitt Rd Unit 102, Key West, FL 33040
    • /11

      Not Listed For Sale

      LOT 38 W Indies Dr, Ramrod Key, FL 33042

      LOT 38 W Indies Dr, Ramrod Key, FL 33042

      Last Sold Summary

      • 144 Days On Market

  • /28

    $1,525,000

    Open House 6/18
    • 3 Beds
    • 2 Baths
    • 1,736 Sq Ft

    87851 Old Hwy Unit M42, Islamorada, FL 33036

    Ocean Harbour condo with Atlantic ocean views and a boat slip in Islamorada. 3 bedroom, 2 bathroom luxury condo offers expansive ocean views and comfortable living space. The thoughtfully redesigned floor plan enhances the primary suite layout, adds a third bedroom, updates both bathrooms, and expands the living area by enclosing the porch as additional interior living space; maximizing

    Agent Photo

    Carolyn Ambler

    American Caribbean Real Estate, Christie's International Real Estate

    (645) 218-2440

    87851 Old Hwy Unit M42, Islamorada, FL 33036
  • /65

    $6,995 Per Month

    • 4 Beds
    • 3 Baths
    • 3,116 Sq Ft
    • House for Rent

    30825 Ortega Ln, Big Pine Key, FL 33043

    Welcome to your slice of paradise in Big Pine Key! This stunning property offers peace and privacy on a quietstreet, just minutes from world class fishing, boating, and the natural beauty of Bahia Honda State Park. Thischarming home comes fully furnished and features an open-concept layout, modern updates, and coastal finishesthroughout. relax on the covered porch, entertain on the

    Walter Vargas Cervera Real Estate Inc.

    30825 Ortega Ln, Big Pine Key, FL 33043
  • /36

    $1,120,000

    Sold Mar 24, 2026

    2148 Bahia Shores Rd, Big Pine Key, FL 33043

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 1988

    Last Sold Summary

    • 5% Below List Price
    • $933/SF
    • 1 Day On Market

    Current Estimated Value $1,133,687

    Last Listing Agent Anne Press Lokation Real Estate

    2148 Bahia Shores Rd, Big Pine Key, FL 33043
    • /17

      Not Listed For Sale

      Lot 9 Avenida Primiceria, Marathon, FL 33050

      Lot 9 Avenida Primiceria, Marathon, FL 33050

      Last Sold Summary

      • 23 Days On Market

  • /60

    $3,575,000

    $325K PRICE DROP Under Contract
    • 5 Beds
    • 5.5 Baths
    • 2,033 Sq Ft

    1230 South St, Key West, FL 33040

    Some homes are renovated. This one was restored - with the kind of patience and reverence that only comes once in a generation. 1230 South Street is a five-bedroom, five-and-a-half-bath estate that stands apart not simply for what it has, but for what it represents: a masterwork of historical accuracy and modern luxury, executed without compromise. Original Dade County Pine runs throughout the

    Agent Photo

    Damian Vantriglia

    Berkshire Hathaway HomeServices Knight & Gardner Realty

    (786) 840-2961

    1230 South St, Key West, FL 33040
  • /41

    $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 - Coral Gables

    2 Snipe Rd, Key Largo, FL 33037
  • /37

    $1,720,000

    Sold Jun 01, 2026

    309 Woods Ave, Tavernier, FL 33070

    • 3 Beds
    • 3 Baths
    • 1,248 Sq Ft
    • Built 1975

    Last Sold Summary

    • 4% Below List Price
    • $1,378/SF
    • 2 Days On Market

    Current Estimated Value $1,797,782

    Last Listing Agent Jessica Pinder Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

    309 Woods Ave, Tavernier, FL 33070
    • /2

      Not Listed For Sale

      Lot 8 Avenida Primiceria, Marathon, FL 33050

      Lot 8 Avenida Primiceria, Marathon, FL 33050

  • /40

    $1,425,000

    $150K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,395 Sq Ft

    1901 S Roosevelt Blvd Unit 401, Key West, FL 33040

    Discover the rare opportunity to own a premier developer's unit in one of Key West's most desirable waterfront communities. Perfectly positioned just across the street from world-famous Smathers Beach, this spacious 3-bedroom, 2-bath condo blends coastal luxury with unbeatable island convenience.Inside, expansive living spaces open to large windows and glass doors showcasing ocean views and

    Agent Photo

    Emily Lombard

    Ocean Sotheby's International Realty

    (786) 686-5429

    1901 S Roosevelt Blvd Unit 401, Key West, FL 33040
  • /37

    $4,750 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,587 Sq Ft
    • House for Rent

    94825 Overseas Hwy Unit 107, Key Largo, FL 33037

    Step into this Gorgeous Key Largo home, 3 bedrooms, 2.5 bath, fully furnished, all upgraded with pool and ocean views. There is an elevator for your convenience. Beautiful white kitchen, open to dining and family room, half bath, and balcony with amazing views. Second floor has the 3 bedrooms and 2 bathrooms. Lease up to 1 year and 3 months minimum.Tenant-occupied, please do not disturb.

    Aisleen Falcon-Cabral Luxe Properties

    94825 Overseas Hwy Unit 107, Key Largo, FL 33037
  • /26

    $500,000

    Sold Oct 29, 2025

    1W & 2W Cooks Island, Cook Island Key, FL 33043

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft
    • Built 2007

    Last Sold Summary

    • 26% Below List Price
    • $556/SF
    • 93 Days On Market

    Last Listing Agent Rose Dell Keller Williams Key West Compass Realty

    1W & 2W Cooks Island, Cook Island Key, FL 33043
    • /22

      Est $1,682,293

      Not Listed For Sale

      800 Fleming St Unit C1, Key West, FL 33040

      • 2 Beds
      • 2 Baths
      • 1,550 Sq Ft
      • Built 1910
      800 Fleming St Unit C1, Key West, FL 33040

      Last Sold Summary

      • 53 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)

    (786) 981-1937

    32 Merganser Ln, Key West, FL 33040
  • /16

    $6,500 Per Month

    • 3 Beds
    • 2 Baths
    • 2,000 Sq Ft
    • Condo for Rent

    7204 Gulf of Mexico Blvd Unit 204, Marathon, FL 33050

    Anthony Hollis Hollis Realty Group, Inc.

    7204 Gulf of Mexico Blvd Unit 204, Marathon, FL 33050
  • /11

    $600,000

    Sold Apr 13, 2026

    126 Zane Gray Creek Dr, Layton, FL 33001

    • Land
    • 4,791 Sq Ft
    • $5,454,545 per Acre

    Last Sold Summary

    • 22% Below List Price
    • 134 Days On Market

    Last Listing Agent Jonathan Minerick Homecoin.com

    126 Zane Gray Creek Dr, Layton, FL 33001
    • /20

      Not Listed For Sale

      31048 Avenue J, Big Pine Key, FL 33043

      • 2 Beds
      • 1 Bath
      • 588 Sq Ft
      • Built 1967
      31048 Avenue J, Big Pine Key, FL 33043

      Last Sold Summary

      • 151 Days On Market

  • /24

    $999,000

    Under Contract
    • Land
    • 1.3 Acres
    • $768,462 per Acre

    58876 Overseas Hwy, Duck Key, FL 33050

    Rare opportunity to own a ROGO Exempt oceanfront property in Marathon! This expansive 56,488 sq. ft. parcel offers approximately 100 feet of direct ocean frontage and stretches nearly 570 feet deep, creating the perfect setting for a private estate or investment property. Previously improved with a residence (just recently removed), this cleared and buildable lot allows you to build immediately

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (844) 541-5029

    58876 Overseas Hwy, Duck Key, FL 33050
  • /15

    $4,800 Per Month

    • 2 Beds
    • 2 Baths
    • 1,281 Sq Ft
    • Property 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

    Cathy More Epique Realty Inc.

    225 W 2nd Ct, Key Largo, FL 33037
  • /67

    $3,150,000

    Sold Jun 09, 2026

    270 E Caribbean Dr, Summerland Key, FL 33042

    • 4 Beds
    • 4 Baths
    • 2,375 Sq Ft
    • Built 2024

    Last Sold Summary

    • 2% Below List Price
    • $1,326/SF
    • 22 Days On Market

    Current Estimated Value $2,722,116

    Last Listing Agent Sandra Tuttle Island Welcome Real Estate

    270 E Caribbean Dr, Summerland Key, FL 33042
    • /2

      Est $507,827

      Not Listed For Sale

      3930 S Roosevelt Blvd Unit W410, Key West, FL 33040

      • 2 Beds
      • 2 Baths
      • 804 Sq Ft
      • Built 1991
      3930 S Roosevelt Blvd Unit W410, Key West, FL 33040

  • /45

    $2,150,000

    $200K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,127 Sq Ft

    1501 Ocean Bay Dr Unit A1 & 50' Boat Slip, Key Largo, FL 33037

    Luxury Ocean Front End Unit. The best views from the complex in this townhome with 50 ft deeded slip and boat lift. Indulge in the vibrant ocean colors of turquoise blues and greens from every room. Awaken to awe-inspiring sunrises accompanied by refreshing ocean breezes. This hidden gem has the best views in the exclusive Key Largo Yacht Club with the boat slip just steps away. Convenience,

    Agent Photo

    Terry Canto

    American Caribbean Real Estate, Christie's International Real Estate

    (844) 994-2188

    1501 Ocean Bay Dr Unit A1 & 50' Boat Slip, Key Largo, FL 33037
  • /24

    $2,600 Per Month

    • 2 Beds
    • 1.5 Baths
    • 1,024 Sq Ft
    • Apartment for Rent

    300 Ocean Dr Unit 20, Key Largo, FL 33037

    Quaint and comfortable condo located in the heart of Key Largo! This 2 bedroom, 1.5 bath is newly upgraded with granite countertops, Nest Smart thermostat, and LED retractable ceiling fans with remote control. Each bedroom has its own balcony and plenty of storage space! Unit is located on the 2nd floor, corner unit, and comes with accordion shutters for all windows. Within walking distance to

    Abdul Wahid C&J Realty Inc.

    300 Ocean Dr Unit 20, Key Largo, FL 33037
  • /38

    $4,275,000

    Sold Mar 04, 2026

    231 E Shore Dr Unit 7, Key West, FL 33040

    • 5 Beds
    • 5.5 Baths
    • 4,103 Sq Ft
    • Built 2025

    Last Sold Summary

    • 1% Below List Price
    • $1,042/SF
    • 173 Days On Market

    Last Listing Agent Stephanie Marinucci Serhant

    231 E Shore Dr Unit 7, Key West, FL 33040
    • /32

      Not Listed For Sale

      84745 Old Hwy Unit 11, Islamorada, FL 33036

      • 3 Beds
      • 3 Baths
      • 1,680 Sq Ft
      • Built 2023
      84745 Old Hwy Unit 11, Islamorada, FL 33036

      Last Sold Summary

      • 38 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

    (645) 225-0831

    441 3rd St, Key Colony Beach, FL 33051
  • /78

    $287,500

    Sold Sep 08, 2025

    104000 Overseas Hwy Unit 2-5, Key Largo, FL 33037

    • 3 Beds
    • 3 Baths
    • 2,300 Sq Ft
    • Built 2008

    Last Sold Summary

    • 4% Below List Price
    • $125/SF
    • 4 Days On Market

    Current Estimated Value $1,250,973

    Last Listing Agent Kelly Randin RE/MAX All Keys Real Estate

    104000 Overseas Hwy Unit 2-5, Key Largo, FL 33037
    • /28

      Not Listed For Sale

      130 Overseas Hwy, Islamorada, FL 33036

      130 Overseas Hwy, Islamorada, FL 33036

      Last Sold Summary

      • 17 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

    (855) 679-9394

    17151 Marlin Dr, Sugarloaf Key, FL 33042
  • /26

    $600,000

    Sold Oct 09, 2025

    1105 Watson St, Key West, FL 33040

    • 2 Beds
    • 2 Baths
    • 1,592 Sq Ft
    • Built 1943

    Last Sold Summary

    • 50% Below List Price
    • $377/SF
    • 237 Days On Market

    Current Estimated Value $697,535

    Last Listing Agent Francesca Santiago Keller Williams Realty Professionals (KW)

    1105 Watson St, Key West, FL 33040
    • /2

      Not Listed For Sale

      170 Mars Ln, Key West, FL 33040

      • 2 Beds
      • 1 Bath
      • 672 Sq Ft
      • Built 1979
      170 Mars Ln, Key West, FL 33040

  • /32

    $615,000

    $10K 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

    (645) 218-3402

    3205 Pearl Ave, Key West, FL 33040
  • /75

    $2,715,000

    Sold May 14, 2026

    77 Bay Dr, Key West, FL 33040

    • 4 Beds
    • 3 Baths
    • 1,820 Sq Ft
    • Built 1994

    Last Sold Summary

    • 6% Below List Price
    • $1,492/SF
    • 71 Days On Market

    Current Estimated Value $2,754,871

    Last Listing Agent Leigh Ann Roach Berkshire Hathaway HomeServices Knight & Gardner Realty

    77 Bay Dr, Key West, FL 33040

Showing Results 641 - 680, Page 17 of 18

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