Monroe County, FL Homes

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  /31

  $795,000

  • 3 Beds
  • 1 Bath
  • 1,562 Sq Ft

  360 W Shore Dr, Summerland Key, FL 33042

  Discover island living in this charming 3-bedroom, 1-bath canal-front home located in desirable Summerland Key, featuring fabulous sunset views. Set on a 60-foot-wide deep canal with approximately 10 minutes of boating access to the open ocean, this property is ideal for avid boaters and water lovers.The open living area flows seamlessly into an enclosed porch, creating a versatile space perfect

  

  Brenda Thomas

  Island Welcome Real Estate

  (786) 949-3594

  360 W Shore Dr, Summerland Key, FL 33042
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  /7

  $3,800 per month

  • 3 Beds
  • 2 Baths
  • 1,585 Sq Ft
  • House for Rent

  308 2nd Terrace, Key Largo, FL 33037

  Lovely home ready for your family. Lage 3/2 with media room which can be used for 4th bedroom. Large back screen porch and deck area. Premier family neighborhood. Available February 15th.

  Maryann Warren Coldwell Banker - Ft. Lauderdale

  308 2nd Terrace, Key Largo, FL 33037
• 

  

  

  /40

  $522,500 Sold Oct 10, 2025

  1115 Sombrero Blvd Unit 101A, Marathon, FL 33050

  • 2 Beds
  • 2 Baths
  • 1,096 Sq Ft
  • Built 1975

  Last Sold Summary

  • 5% Below List Price
  • $477/SF
  • 228 Days On Market

  Current Estimated Value $519,827

  Last Listing Agent Ally Kelley Ocean Sotheby's International

  1115 Sombrero Blvd Unit 101A, Marathon, FL 33050
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  /8

  Not Listed For Sale

  201 Ocean Reef Dr Unit ES-05, Key Largo, FL 33037

  201 Ocean Reef Dr Unit ES-05, Key Largo, FL 33037
• 

  

  

  /36

  $699,000 Open Sun 1PM - 3PM

  • 3 Beds
  • 2 Baths
  • 1,039 Sq Ft

  29048 Iris Dr, Big Pine Key, FL 33043

  Great price for an entry-level canal-front home! Located on a 50-foot-wide canal, this updated 3-bedroom, 2-bath home provides good boating access to Pine Channel, the Atlantic Ocean, and the backcountry. The great room features a cathedral ceiling, abundant natural light from a south-facing picture window, and French doors opening to a covered porch with canal views. Upgrades include

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  (855) 528-3127

  29048 Iris Dr, Big Pine Key, FL 33043
• 

  

  /25

  $4,300 - $4,650 per month

  NAS Key West Homes

  3 Beds

  800 Sigsbee Rd, Key West, FL 33040

  NAS Key West Homes is located in Key West, Florida. In addition to the prime location, we offer a variety of floor plans and neighborhoods to fit your needs. Our community is all-inclusive, with baseline utilities, exclusive recreational and fitness amenities, lawn care and an award-winning resident events program included in your monthly rent. Our community professional on-site property name

  800 Sigsbee Rd, Key West, FL 33040
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  /7

  $1,056,000 Sold Jul 21, 2025

  972 Shaw Dr, Key Largo, FL 33037

  • Land

  Last Sold Summary

  • 12% Below List Price
  • 54 Days On Market

  Current Estimated Value $1,063,516

  Last Listing Agent Betsy Perez LoKation Real Estate

  972 Shaw Dr, Key Largo, FL 33037
• 

  

  /23

  Est $559,285 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 690 Sq Ft

  1875 109th Street Gulf Unit A, Marathon, FL 33050

  1875 109th Street Gulf Unit A, Marathon, FL 33050
• 

  

  /79

  $2,600,000

  • 4 Beds
  • 3 Baths
  • 2,321 Sq Ft

  16 Azalea Dr, Key West, FL 33040

  Welcome to 16 Azalea Drive, a completely reimagined home that embodies sophisticated coastal living, blending modern elegance with meticulous attention to detail at every turn. Thoughtfully redesigned from the ground up, this 4-bedroom, 3-bath property spans nearly 2,400 sq ft of refined living space. The open layout creates a seamless flow between the living, dining & kitchen areas, each curated

  

  Tommy Mack

  Coastal Collection Real Estate Inc.

  (786) 957-4363

  16 Azalea Dr, Key West, FL 33040
• 

  

  /8

  $4,000 per month

  • 3 Beds
  • 2 Baths
  • 1,000 Sq Ft
  • Property for Rent

  1110 White St Unit 1, Key West, FL 33040

  Spacious 3-bedroom, 2-bath apartment located at 1110 White Street in Key West. Rent is $4,000 per month. Water, trash, and sewage are included; tenant is responsible for electricity.This unit is ideally situated steps from downtown, with a convenience store, Faustos Supermarket, and a pizza shop located right below the building. Enjoy easy island living with an approximately 10-minute walk to the

  Vladimir Prokhodnoy Expert Realty LLC (HQ)

  1110 White St Unit 1, Key West, FL 33040
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  /3

  $650,000 Sold Dec 04, 2025

  806 Pearl St, Key West, FL 33040

  • 4 Beds
  • 3 Baths
  • 1,504 Sq Ft
  • Built 1933

  Last Sold Summary

  • $432/SF
  • 0 Days On Market

  Last Listing Agent Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

  806 Pearl St, Key West, FL 33040
• 

  

  /15

  Est $2,509,095 Not Listed For Sale

  101 Dorsett Dr, Marathon, FL 33050

  101 Dorsett Dr, Marathon, FL 33050
• 

  

  /16

  $999,000

  • Land

  21082 6th Ave, Summerland Key, FL 33042

  An exceptional opportunity awaits in one of the Lower Keys' most desirable neighborhoods. This oversized corner lot is ROGO exempt and comes with approved building plans already on file with Monroe County, allowing you to skip the waiting line and begin building your dream home immediately. The existing structure has been demolished, clearing the way for a seamless transition from vision to

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (645) 300-6302

  21082 6th Ave, Summerland Key, FL 33042
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  /35

  $2,650 - $3,967 per month

  The Quarry

  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.

  10 Betty Rose Dr, Key West, FL 33040
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  /10

  $560,000 Sold Dec 26, 2025

  2433 Linda Ave, Key West, FL 33040

  • 3 Beds
  • 2 Baths
  • 2,099 Sq Ft
  • Built 1953

  Last Sold Summary

  • 7% Below List Price
  • $267/SF
  • 96 Days On Market

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

  2433 Linda Ave, Key West, FL 33040
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  /49

  Est $414,290 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 820 Sq Ft

  593 Sombrero Beach Rd Unit 14A, Marathon, FL 33050

  593 Sombrero Beach Rd Unit 14A, Marathon, FL 33050
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  /68

  $2,985,000 Open Sun 11AM - 2PM

  • 3 Beds
  • 2 Baths
  • 2,232 Sq Ft

  23941 Henry St, Summerland Key, FL 33042

  Oceanfront Luxury Retreat with Private Beach, Protected Dockage & Quick Direct Boating Access to both Ocean & Gulf.Wake up to breathtaking Atlantic sunrises and unwind with glowing sunsets in this custom 2-story 4,024 SF CBS oceanfront home, perfectly positioned on a private street with only four residences. Located on Summerland Key, this Island inspired escape offers panoramic ocean views,

  

  Stacy Shahan

  Island Real Estate Company Florida Keys

  (786) 686-4688

  23941 Henry St, Summerland Key, FL 33042
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  /41

  $7,500 per month

  • 4 Beds
  • 3 Baths
  • 2,581 Sq Ft
  • House for Rent

  103 Starfish Ln, Tavernier, FL 33070

  Awesome view of the Bay from the Chickee Hut Dock to Full Roof Top Patio. 2 story Large Master Bedroom with Steam Shower. Concrete L shaped dock with 15,000 lb lift. There is also a cocktail pool to enjoy after a day out on the water. Ready for your families dream vacation in the Florida Keys. Fantastic Neighbors and Neighborhood. Great water access!! King bed in main bedroom queen beds in the

  George Matter EXP Realty LLC

  103 Starfish Ln, Tavernier, FL 33070
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  /9

  $240,000 Sold Jun 13, 2025

  100 Morris Ln F-5, Key Largo, FL 33037

  • Land
  • 0 Acre

  Last Sold Summary

  • 5% Above List Price
  • 30 Days On Market

  Last Listing Agent Yvette Doherty Coldwell Banker Schmitt R.E.

  100 Morris Ln F-5, Key Largo, FL 33037
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  /9

  Not Listed For Sale

  • 5 Beds
  • 5 Baths
  • 3,013 Sq Ft

  59720 Overseas Hwy Unit 2, Marathon, FL 33050

  59720 Overseas Hwy Unit 2, Marathon, FL 33050
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  /63

  $2,450,000

  • 3 Beds
  • 3 Baths
  • 2,486 Sq Ft

  30468 Oleander Blvd, Big Pine Key, FL 33043

  Discover the easygoing charm of the Lower Keys at this .81-acre waterfront estate, featuring a two-bedroom, two-bath main house and a one-bedroom, one-bath guest cottage with views over Bogie Channel. Enjoy leisurely days entertaining under the large poolside tiki hut or on the covered platform at the end of the 463-foot pier--perfect for relaxing with family and friends while watching sunsets

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  (877) 796-4209

  30468 Oleander Blvd, Big Pine Key, FL 33043
• 

  

  /20

  $5,537 - $15,000 per month

  Little Torch Cottages

  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

  28501 Channel View Dr, Little Torch Key, FL 33042
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  /4

  $1,200,000 Sold Nov 20, 2025

  1108 Whitehead St, Key West, FL 33040

  • Land

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Terri Spottswood Truman & Co. (KW)

  1108 Whitehead St, Key West, FL 33040
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  /6

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 480 Sq Ft

  31450 Avenue C, Big Pine Key, FL 33043

  31450 Avenue C, Big Pine Key, FL 33043
• 

  

  /51

  $479,000

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  55 Boca Chica Rd Unit 447, Key West, FL 33040

  Welcome to Seaside Resort, a gated, waterfront community just 10 minutes from the heart of Key West! This bright, cheerful 2 bed, 2 bath home with 864 sq ft of updated living space is move-in ready and offered turn-key furnished. Step inside this impeccably kept home to discover an open-concept layout filled with natural light, coastal charm, and a spacious feel. The kitchen features crisp white

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (645) 230-1331

  55 Boca Chica Rd Unit 447, Key West, FL 33040
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  /41

  $3,700 per month

  • 3 Beds
  • 2.5 Baths
  • 1,580 Sq Ft
  • House for Rent

  94825 Overseas Hwy Unit 58, Key Largo, FL 33037

  Custom-built solid concrete block home in the desirable Key Largo Ocean Resort. This furnished (furniture negotiable) residence features stainless steel appliances, quartz countertops, porcelain plank floors, marble bathrooms, keystone accent wall, built-in wood closets, impact doors and windows, metal roof, and washer/dryer.The ground level offers a private storage area, covered parking for

  Shanti Cope Coldwell Banker Schmitt Key Largo

  94825 Overseas Hwy Unit 58, Key Largo, FL 33037
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  /55

  $1,375,000 Sold May 30, 2025

  158 Iroquois Dr, Islamorada, FL 33036

  • 3 Beds
  • 3 Baths
  • 1,920 Sq Ft
  • Built 1977

  Last Sold Summary

  • 19% Below List Price
  • $716/SF
  • 210 Days On Market

  Current Estimated Value $1,388,483

  Last Listing Agent Jessica Wolf Luxe Properties, LLC.

  158 Iroquois Dr, Islamorada, FL 33036
• 

  

  /21

  Est $233,391 Not Listed For Sale

  • 1 Bed

  97 Coco Plum Dr Unit B-29, Marathon, FL 33050

  97 Coco Plum Dr Unit B-29, Marathon, FL 33050
• 

  

  /66

  $539,000

  • 2 Beds
  • 2 Baths
  • 836 Sq Ft

  701 Spanish Main Dr Unit 154, Cudjoe Key, FL 33042

  Coastal Paradise with Income Potential! Stunning 2BR/2BA Home Steps from the Ocean.Embrace the ultimate coastal lifestyle in this beautifully maintained 2-bedroom, 2-bathroom home, perfectly positioned directly across the street from the ocean. Wake up to serene water views and the soothing sound of the waves from your spacious, private decka"an ideal spot for your morning coffee or evening

  

  Ian Calderwood

  Bluescape Real Estate

  (786) 882-1915

  701 Spanish Main Dr Unit 154, Cudjoe Key, FL 33042
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  /35

  $2,100 - $4,085 per month

  Ocean Walk

  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

  3900 S Roosevelt Blvd, Key West, FL 33040
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  /33

  $250,000 Sold Nov 18, 2025

  300 Duck Key Dr Unit 3, Marathon, FL 33050

  • 1 Bed
  • 1 Bath
  • 510 Sq Ft
  • Built 1969

  Last Sold Summary

  • 37% Below List Price
  • $490/SF
  • 226 Days On Market

  Last Listing Agent Ellen Gvili Ocean Sotheby's International Realty

  300 Duck Key Dr Unit 3, Marathon, FL 33050
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  /31

  Est $809,040 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,008 Sq Ft

  22727 Jolly Roger Dr, Cudjoe Key, FL 33042

  22727 Jolly Roger Dr, Cudjoe Key, FL 33042
• 

  

  /58

  $3,750,000

  • 3 Beds
  • 2 Baths
  • 1,851 Sq Ft

  755 & 744 Sawyer Dr, Cudjoe Key, FL 33042

  In prestigious Cudjoe Gardens, this fully renovated Keys retreat feels more like a private sanctuary than a house. The main oceanfront lot is wrapped in lush, mature landscaping -- buttonwoods in the back, banyan trees along the side, orchids everywhere, irrigation, and low-voltage lighting that makes the property glow at night. It's the kind of tropical setting people move to the Keys

  

  Terrance Sullivan

  Ocean Sotheby's International Realty

  (786) 465-7217

  755 & 744 Sawyer Dr, Cudjoe Key, FL 33042
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  /39

  $7,000 per month

  • 3 Beds
  • 3 Baths
  • 2,484 Sq Ft
  • House for Rent

  90 N Bounty Ln Unit 90, Key Largo, FL 33037

  Beautiful 3-bedroom, 3-bath home offering a laid-back boat-life lifestyle on nearly half an acre and ready to move in. The home features a stainless steel kitchen with beautiful cabinetry, tile flooring throughout, expansive porches perfect for relaxing, and a separate laundry room. Guest bedrooms include large closets and peaceful lake views. Plenty of outdoor space to enjoy, making this a great

  Arelys Doger-Sanchez Keller Williams Realty Premier Properties

  90 N Bounty Ln Unit 90, Key Largo, FL 33037
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  /24

  $525,000 Sold Aug 15, 2025

  3930 S Roosevelt Blvd Unit S405, Key West, FL 33040

  • 3 Beds
  • 2 Baths
  • 1,069 Sq Ft
  • Built 1991

  Last Sold Summary

  • $491/SF
  • 59 Days On Market

  Current Estimated Value $558,151

  Last Listing Agent Tom Mclaughlin Coldwell Banker Schmitt Real Estate Co. (KW)

  3930 S Roosevelt Blvd Unit S405, Key West, FL 33040
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  /56

  Est $1,882,894 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,995 Sq Ft

  271 4th St, Key Colony Beach, FL 33051

  271 4th St, Key Colony Beach, FL 33051
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  /51

  $1,250,000 Open Sun 11AM - 1PM

  • 4 Beds
  • 3 Baths
  • 2,166 Sq Ft

  30985 Hibiscus Dr, Big Pine Key, FL 33043

  CBS POOL HOME OFFERS 133 ft. along the 50 ft. wide canal, boat davits, a fish cleaning station and quick access to Bogie Channel, the Atlantic and back country. Dock multiple boats along the 60 ft. concrete seawall with the possibility of adding more dockage. The fenced 19,762 sq. ft. double lot provides a private, park-like setting featuring an inviting, heated pool, outdoor shower, grilling

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  (888) 284-4668

  30985 Hibiscus Dr, Big Pine Key, FL 33043
• 

  

  /18

  $3,300 - $3,800 per month

  Sunset Marina Apts

  2 Beds

  5555 College Rd, Key West, FL 33040

  5555 College Rd, Key West, FL 33040
• 

  

  /58

  $848,750 Sold Dec 29, 2025

  264 Lincoln Ave, Tavernier, FL 33070

  • 3 Beds
  • 2 Baths
  • 1,040 Sq Ft
  • Built 1988

  Last Sold Summary

  • 22% Below List Price
  • $816/SF
  • 315 Days On Market

  Last Listing Agent Lauren Dunn Coldwell Banker Schmitt Islamorada

  264 Lincoln Ave, Tavernier, FL 33070
• 

  

  /23

  Est $783,830 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft

  78 Coral Way, Key Largo, FL 33037

  78 Coral Way, Key Largo, FL 33037

Showing Results 41 - 80, Page 2 of 18