Monroe County, FL Homes

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  /34

  $749,900

  • 3 Beds
  • 2 Baths
  • 1,431 Sq Ft

  28110 Dorothy Ave, Little Torch Key, FL 33042

  Island living comes easy here, with a free community boat ramp, nearby waterfront basin, and natural Lower Keys scenery all close to home. Set on a large 7,814 sq. ft. corner lot along State Road 4A in Ladies Acre, this 3 bedroom, 2 bath property offers 1,431 sq. ft. of comfortable living space surrounded by mature tropical greenery that adds privacy and natural beauty. Inside, the open living,

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  28110 Dorothy Ave, Little Torch Key, FL 33042
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  /36

  $6,500 Per Month

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

  121 Long Key Lake Dr, Layton, FL 33001

  Beautifully redesigned and fully furnished waterfront home available for seasonal rental in Layton. Available starting October 2026 till May 2027. Recently renovated from top to bottom, this canal-front retreat feels like a brand new home while offering the peaceful, natural setting that makes this part of the Keys so special. Boaters will love the 50 feet of dockage, 15,000-pound boat lift, and

  

  Megan Jones

  Coldwell Banker Schmitt Islamorada

  121 Long Key Lake Dr, Layton, FL 33001
• 

  

  

  /13

  $2,800

  Sold Jun 22, 2026

  605 Sombrero Beach Rd Unit 303, Marathon, FL 33050

  • 2 Beds
  • 1 Bath
  • 755 Sq Ft
  • Built 1974

  Last Sold Summary

  • 3% Below List Price
  • $4/SF
  • 52 Days On Market

  Current Estimated Value $393,052

  Last Listing Agent Alicia Lund, P.A. Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

  605 Sombrero Beach Rd Unit 303, Marathon, FL 33050
• 

  

  

  /3

  Est $257,210

  Not Listed For Sale

  325 Calusa St Unit 386, Key Largo, FL 33037

  325 Calusa St Unit 386, Key Largo, FL 33037

  Last Sold Summary

  • 39 Days On Market
• 

  

  

  /102

  $2,949,000

  • 6 Beds
  • 4 Baths
  • 3,392 Sq Ft

  420 11th St, Key Colony, FL 33051

  Welcome to your waterfront retreat in the heart of Key Colony Beach. Perfectly positioned on a deep-water canal with 75' of concrete dockage, this spacious 6-Bed, 4-Bath residence offers the ideal blend of island living, boating convenience, and exceptional investment potential. Designed to comfortably accommodate family and guests, the property features a unique floor plan with a 4-Bedroom,

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  420 11th St, Key Colony, FL 33051
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  /34

  Starting at $3,199 Per Month

  • 1 - 3 Beds

  96 Coco Plum Dr, Marathon, FL 33050

  CoCo Vista

  

  96 Coco Plum Dr, Marathon, FL 33050
• 

  

  /42

  $975,000

  Sold Jun 26, 2026

  60 Golf Club Dr, Key West, FL 33040

  • 3 Beds
  • 2.5 Baths
  • 1,203 Sq Ft
  • Built 1996

  Last Sold Summary

  • 15% Below List Price
  • $810/SF
  • 38 Days On Market

  Current Estimated Value $971,312

  Last Listing Agent Matthew Sheehan Ocean Sotheby's International Realty

  60 Golf Club Dr, Key West, FL 33040
• 

  

  /3

  Not Listed For Sale

  83 Coco Plum Dr, Marathon, FL 33050

  • 6 Beds
  • 4 Baths
  • 2,072 Sq Ft
  • Built 2025

  83 Coco Plum Dr, Marathon, FL 33050

  Last Sold Summary

  • 0 Days On Market
• 

  

  /70

  $1,695,000

  • 3 Beds
  • 2 Baths
  • 1,882 Sq Ft

  30463 Hawk Ln, Big Pine Key, FL 33043

  Welcome to your private Lower Keys oasis, where solid concrete construction meets refined coastal style. This beautifully designed 3-bedroom, 2-bath waterfront home is offered fully furnished and truly move-in ready, featuring impact windows and doors, a sleek 24 gauge standing seam metal roof, and bright, open living spaces made for effortless island living. Outdoors, the home transforms into a

  

  Sandra Tuttle

  Island Welcome Real Estate

  30463 Hawk Ln, Big Pine Key, FL 33043
• 

  

  /50

  $15,000 Per Month

  • 4 Beds
  • 3.5 Baths
  • 1,570 Sq Ft
  • House for Rent

  16 North Dr, Key Largo, FL 33037

  Bayfront living in the Upper Keys at its finest. Located at 16 North Drive, this modern coastal residence offers 3 bedrooms plus a studio and separate in-law quarters, 5 bathrooms, and approximately 2,608 sq ft of living space, set on a 0.26-acre lot with serene open-bay views and calm waters. Designed for relaxed island living, the home features light-filled interiors, seamless indoor-outdoor

  

  Catherine Pineda

  Coldwell Banker - Pinecrest

  16 North Dr, Key Largo, FL 33037
• 

  

  /32

  $837,500

  Sold Jul 22, 2026

  31 South Dr, Key Largo, FL 33037

  • 3 Beds
  • 2 Baths
  • 1,984 Sq Ft
  • Built 1972

  Last Sold Summary

  • 16% Below List Price
  • $422/SF
  • 68 Days On Market

  Current Estimated Value $890,335

  Last Listing Agent Philip Kravitz Coldwell Banker Schmitt Key Largo

  31 South Dr, Key Largo, FL 33037
• 

  

  /39

  Est $782,375

  Not Listed For Sale

  168 Ocean Dr, Tavernier, FL 33070

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 1983

  168 Ocean Dr, Tavernier, FL 33070

  Last Sold Summary

  • 22 Days On Market
• 

  

  /65

  $2,499,000

  Open Sat 11AM - 1PM

  • 4 Beds
  • 2 Baths
  • 2,739 Sq Ft

  21023 2nd Ave, Summerland Key, FL 33042

  Experience the ultimate Florida Keys boating lifestyle at this exceptional waterfront residence in prestigious Cudjoe Gardens. Situated on a rare double lot encompassing 16,827 square feet, this CBS-built, ground-level home sits above the flood plain and offers approximately 225 feet of waterfront on two sides, deep-water dockage, and remarkably quick ocean access. Designed for comfort and

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  21023 2nd Ave, Summerland Key, FL 33042
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  /24

  Starting at $2,500 Per Month

  • 2 Beds

  21585 Overseas Hwy, Cudjoe Key, FL 33042

  Discover our newly constructed community at Coco Palms in Cudjoe Key, Florida. The leasing team will assist you in finding your new place. A selection of amenities are waiting for you: hurricane windows and doors, dishwashers, washers and dryers and convenient on-site parking options. Contact us today to see available floor plans and find your new place at Coco Palms.

  Coco Palms

  

  21585 Overseas Hwy, Cudjoe Key, FL 33042
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  /69

  $725,000

  Sold Feb 17, 2026

  16 Jewfish Ave, Key Largo, FL 33037

  • 3 Beds
  • 2 Baths
  • 1,469 Sq Ft
  • Built 2018

  Last Sold Summary

  • 6% Below List Price
  • $494/SF
  • 153 Days On Market

  Current Estimated Value $737,815

  Last Listing Agent Silvestri Team Jeanette & Janessa Silves Coldwell Banker Schmitt Key Largo

  16 Jewfish Ave, Key Largo, FL 33037
• 

  

  /26

  Est $1,455,651

  Not Listed For Sale

  123 Peace Ave, Tavernier, FL 33070

  • 3 Beds
  • 2 Baths
  • 1,242 Sq Ft
  • Built 2011

  123 Peace Ave, Tavernier, FL 33070

  Last Sold Summary

  • 148 Days On Market
• 

  

  /106

  $9,999,000

  Under Contract

  • 5 Beds
  • 4.5 Baths
  • 4,622 Sq Ft

  87 Cannon Royal Dr, Key West, FL 33040

  Introducing an extraordinary and completely custom Polynesian-inspired estate designed by the owner with finishes imported from all over the world. Perfectly positioned on the most premier lot within the exclusive gated enclave of Shark Key, offering an exceptional blend of privacy and waterfront luxury. Set on a sprawling 1.56-acre lot with an impressive 850 feet of water frontage, this custom

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  87 Cannon Royal Dr, Key West, FL 33040
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  /76

  $12,500 Per Month

  • 4 Beds
  • 3 Baths
  • 1,800 Sq Ft
  • House for Rent

  129 Nautilus Dr, Islamorada, FL 33036

  Waterfront Islamorada Pool Home with Private Beach Access to White Marlin Beach. Experience the best of the Florida Keys in this beautifully updated waterfront retreat in Islamorada, designed to accommodate up to 12 guests and perfect for family vacations, multigenerational gatherings, or extended stays. The spacious layout features a main living area upstairs, while the ground level offers a

  

  Victor Ruiz

  Move Miami, LLC.

  129 Nautilus Dr, Islamorada, FL 33036
• 

  

  /3

  $2,600,000

  Sold Mar 26, 2026

  152 Giardino Dr, Islamorada, FL 33036

  • 2 Beds
  • 3 Baths
  • 1,832 Sq Ft
  • Built 1989

  Last Sold Summary

  • $1,419/SF
  • 0 Days On Market

  Current Estimated Value $2,628,616

  Last Listing Agent Carolyn Ambler American Caribbean Real Estate, Christie's International Real Estate

  152 Giardino Dr, Islamorada, FL 33036
• 

  

  /17

  Est $355,450

  Not Listed For Sale

  5555 College Rd Unit 12, Key West, FL 33040

  • 1 Bed
  • 50 Sq Ft
  • Built 2000

  5555 College Rd Unit 12, Key West, FL 33040

  Last Sold Summary

  • 3 Days On Market
• 

  

  /45

  $2,499,000

  $300K PRICE DROP

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

  156 Sea Ln, Key West, 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, Key West, FL 33040
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  /35

  Starting at $2,850 Per Month

  • 1 - 3 Beds

  10 Betty Rose Dr, Key West, FL 33040

  Welcome to The Quarry, a residential community in Key West, FL featuring one, two, and three bedroom apartments. Spacious layouts welcome you home, along with exceptional service and an ideal location close to shopping, dining and entertainment.

  The Quarry

  

  10 Betty Rose Dr, Key West, FL 33040
• 

  

  /88

  $700,000

  Sold Dec 31, 2025

  104500 Overseas Hwy Unit C301, Key Largo, FL 33037

  • 3 Beds
  • 2 Baths
  • 1,577 Sq Ft
  • Built 1981

  Last Sold Summary

  • 11% Below List Price
  • $444/SF
  • 1 Day On Market

  Current Estimated Value $730,073

  Last Listing Agent Strain-Pabotoy T Coldwell Banker Schmitt Coldwell Banker Schmitt Key Largo

  104500 Overseas Hwy Unit C301, Key Largo, FL 33037
• 

  

  /7

  Est $1,331,400

  Not Listed For Sale

  972 Shaw Dr, Key Largo, FL 33037

  972 Shaw Dr, Key Largo, FL 33037

  Last Sold Summary

  • 54 Days On Market
• 

  

  /55

  $2,859,000

  $40K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 2,286 Sq Ft

  814 Ashe St, Key West, FL 33040

  Built in 2008, this stunning 3-bedroom, 3.5-bath pool home perfectly blends the timeless character of classic Key West architecture with the comfort and convenience of modern construction. Ideally located just a short stroll from shops, restaurants, bars, and the world-famous Duval Street, this home offers the best of island living. Step inside to a bright, open-concept main living space with a

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  814 Ashe St, Key West, FL 33040
• 

  

  /28

  $2,950 Per Month

  • 2 Beds
  • 2 Baths
  • 1,016 Sq Ft
  • House for Rent

  21 Poinciana Dr, Key Largo, FL 33037

  All concrete home with impact windows, ample parking for cars and Boat(s) available Furnished Turnkey for Annual Rental, just bring your toothbrush! This home exudes Keys style and charm from the Polished Concrete Flooring to the bright and Islandly decor. Just minutes from John Pennekamp Coral Reef Park State Park in the heart of Key Largo. Tenant is eligible for membership at the exclusive

  

  Andrew Burr

  The Keyes Company

  21 Poinciana Dr, Key Largo, FL 33037
• 

  

  /60

  $1,022,500

  Sold Dec 01, 2025

  29490 Ranger Ave, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,346 Sq Ft
  • Built 2018

  Last Sold Summary

  • 6% Below List Price
  • $760/SF
  • 46 Days On Market

  Current Estimated Value $1,064,010

  Last Listing Agent Jennifer Sylvia Keller Williams Key West Compass Realty

  29490 Ranger Ave, Big Pine Key, FL 33043
• 

  

  /85

  Est $4,638,266

  Not Listed For Sale

  115 Spoonbill Rd, Islamorada, FL 33070

  • 5 Beds
  • 6 Baths
  • 4,100 Sq Ft
  • Built 2025

  115 Spoonbill Rd, Islamorada, FL 33070

  Last Sold Summary

  • 150 Days On Market
• 

  

  /62

  $5,200,000

  • 4 Beds
  • 3.5 Baths
  • 2,660 Sq Ft

  17013 Coral Dr, Sugarloaf Key, FL 33042

  Introducing Blue Sky Pointe - the crown jewel of Sugarloaf Key. Perched on a gated 33,750 sq. ft. peninsula with approximately 730 feet of waterfront, this spectacular 4 Bed, 3.5 Bath modern coastal showpiece is surrounded by glistening water and enjoys Keys famous sunset views over Sugarloaf Sound.Fully renovated with premium craftsmanship, the home features a standing seam metal roof, PGT

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  17013 Coral Dr, Sugarloaf Key, FL 33042
• 

  

  /35

  Starting at $2,429 Per Month

  • Studio - 3 Beds

  3900 S Roosevelt Blvd, Key West, FL 33040

  Ocean Walk apartments are located on the peaceful Atlantic side of the island, nestled among lush natural vegetation, just steps away from the beach. Ideally located just minutes from the best dining, shopping and entertainment Key West has to offer, Ocean Walk Apartment Homes boast spacious one, two, and three bedroom apartments, spectacular views, and first-rate amenities. Each recently

  Ocean Walk

  

  3900 S Roosevelt Blvd, Key West, FL 33040
• 

  

  /55

  $1,850,000

  Sold Jan 30, 2026

  272 Lower Matecumbe Rd, Key Largo, FL 33037

  • 4 Beds
  • 3 Baths
  • 2,262 Sq Ft
  • Built 2025

  Last Sold Summary

  • 31% Below List Price
  • $818/SF
  • 267 Days On Market

  Current Estimated Value $1,899,145

  Last Listing Agent Yvette Doherty Coldwell Banker Schmitt Key Largo

  272 Lower Matecumbe Rd, Key Largo, FL 33037
• 

  

  /58

  Est $3,014,749

  Not Listed For Sale

  243 Pescayo Ave, Marathon, FL 33050

  • 5 Beds
  • 5.5 Baths
  • 2,708 Sq Ft
  • Built 2023

  243 Pescayo Ave, Marathon, FL 33050

  Last Sold Summary

  • 69 Days On Market
• 

  

  /59

  $2,899,000

  • 2 Beds
  • 2 Baths
  • 1,717 Sq Ft

  99 Corte Del Brisas, Marathon, FL 33050

  Sweeping views of the Atlantic Ocean and Sombrero Beach set the stage for this beautifully appointed 2 bedroom, 2 bath waterfront residence. Located just steps from the beach and offering quick deep-draft boating access, the home brings together open-water scenery, effortless days on the water, and resort-style living in one of Marathon's most desirable settings. Inside, natural light pours

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  99 Corte Del Brisas, Marathon, FL 33050
• 

  

  /20

  Starting at $3,999 Per Month

  • 2 - 4 Beds

  28501 Channel View Dr, Little Torch Key, FL 33042

  In Little Torch Key, near Mile Marker 28 on US Highway 1, Little Torch Cottages features 48 homes for those looking for something special. This beautiful property has 400 feet of open water views on Pine Channel, and also offers 22 foot boat slips at a discounted monthly rate for community residents. You will also be able to enjoy a community Clubhouse, park, BBQ areas, Paddle Board and Kayak

  Little Torch Cottages

  

  28501 Channel View Dr, Little Torch Key, FL 33042
• 

  

  /21

  $440,000

  Sold Apr 10, 2026

  10818 1st Avenue Gulf, Marathon, FL 33050

  • 2 Beds
  • 2 Baths
  • 810 Sq Ft
  • Built 1959

  Last Sold Summary

  • 2% Above List Price
  • $543/SF
  • 5 Days On Market

  Current Estimated Value $430,546

  Last Listing Agent Milly Perez Seafarer Realty LLC

  10818 1st Avenue Gulf, Marathon, FL 33050
• 

  

  /8

  Est $202,726

  Not Listed For Sale

  13 Beach Dr, Key West, FL 33040

  13 Beach Dr, Key West, FL 33040

  Last Sold Summary

  • 149 Days On Market
• 

  

  /43

  $899,000

  $100K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,036 Sq Ft

  420 W Indies Dr, Ramrod Key, FL 33042

  Beautifully renovated canal-front home on an oversized corner lot in the heart of Breezeswept Beach Estates on Ramrod Key, ideally located on one of only two flow-through canals in the neighborhood. This exceptional property offers a rare combination of quality construction, thoughtful upgrades, and excellent boating access The owners spared no expense in the renovation, which includes a

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  420 W Indies Dr, Ramrod Key, FL 33042
• 

  

  /18

  Starting at $3,200 Per Month

  • 2 Beds

  5555 College Rd, Key West, FL 33040

  Sunset Marina Apts

  

  5555 College Rd, Key West, FL 33040
• 

  

  /47

  $811,000

  Sold Mar 25, 2026

  1254 James Ave, Marathon, FL 33050

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1971

  Last Sold Summary

  • 19% Below List Price
  • $704/SF
  • 96 Days On Market

  Last Listing Agent Daniel Cloud Water Vista Realty, Inc.

  1254 James Ave, Marathon, FL 33050
• 

  

  /14

  Est $314,724

  Not Listed For Sale

  62 SE Marlin Ave, Key Largo, FL 33037

  62 SE Marlin Ave, Key Largo, FL 33037

  Last Sold Summary

  • 143 Days On Market

Showing Results 1 - 40, Page 1 of 18