Monroe County, FL Homes

• 

  

  

  /56

  $1,199,000

  $201K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,088 Sq Ft

  171 10th St, Key Colony Beach, FL 33051

  Priced to Sell. Experience the best of Keys living in this immaculate 2-bedroom, 2-bath waterfront home in coveted Key Colony Beach. The inviting coastal layout opens to a very spacious screened-in porch, with newer high end furniture providing a dining area and living area with 55'' TV. You will enjoy this feature, morning, noon and night. Step outside to your private saltwater pool, offering

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (786) 949-2059

  171 10th St, Key Colony Beach, FL 33051
• 

  

  

  /19

  $3,450 Per Month

  • 2 Beds
  • 1.5 Baths
  • 6+ MONTH RENTAL-Temporarily discounted to $3000 for this season!

  121 Golf Club Dr, Key West, FL 33040

  Available May to November - Decorated with island charm, this 2-bedroom 1.5 bath home is located in the Key West Golf Community and is offered fully furnished. The home features Central AC, a full size washer & dryer, and a flat screen TV. The screened deck off the living room and the master bedroom balcony both offer beautiful views of the golf course.The Key West Golf Club HOA is a gated

  121 Golf Club Dr, Key West, FL 33040
• 

  

  

  /16

  $1,400,000

  Sold Mar 16, 2026

  570 Blackbeard Rd, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 1,500 Sq Ft
  • Built 2026

  Last Sold Summary

  • 3% Below List Price
  • $933/SF
  • 14 Days On Market

  Current Estimated Value $1,397,000

  Last Listing Agent Nick Boumerhi Meyer and Boumerhi Realty LLC

  570 Blackbeard Rd, Summerland Key, FL 33042
• 

  

  

  /30

  Est $307,658

  Not Listed For Sale

  101551 Overseas Hwy Unit 14, Key Largo, FL 33037

  101551 Overseas Hwy Unit 14, Key Largo, FL 33037

  Last Sold Summary

  • 76 Days On Market
• 

  

  

  /42

  $1,149,000

  $46K PRICE DROP Under Contract

  • 2 Beds
  • 2 Baths
  • 1,736 Sq Ft

  87851 Old Hwy Unit M24, Islamorada, FL 33036

  Resort-style living at Ocean Harbour. 2BR/2BA oceanfront condo with sweeping Atlantic Ocean views, new kitchen appliances, impact windows/doors and a 6,000-lb boat lift. Boat slip #36 is currently leased from the Association for $100 per month. Boat ramp, trailer storage, and covered parking space included. Enjoy the luxury island lifestyle on 12 gated acres with an oceanfront pool, beach areas,

  

  Carolyn Ambler

  American Caribbean Real Estate, Christie's International Real Estate

  (786) 807-9114

  87851 Old Hwy Unit M24, Islamorada, FL 33036
• 

  

  /25

  $3,995 Per Month

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

  1215 97th Street Ocean Unit 11, Marathon, FL 33050

  Stunning turnkey Atlantic Ocean waterfront condo with dockage, which can fit up to a 24 ft boat! Storm impact windows, sliding glass doors, new kitchen with stainless steel appliances. Quart's countertops, soft close drawers, glass backsplash, under counter lighting. All new bathroom cabinet, large anti-fog mirror cabinet, new tiled shower. All brand-new flooring, paint throughout with coastal

  Natalia Boltz PA Power Net Realty.com Inc.

  1215 97th Street Ocean Unit 11, Marathon, FL 33050
• 

  

  /23

  $600,000

  Sold Jul 15, 2025

  651 William St Unit 1, Key West, FL 33040

  • 1 Bed
  • 1 Bath
  • 599 Sq Ft
  • Built 1933

  Last Sold Summary

  • 28% Below List Price
  • $1,002/SF
  • 191 Days On Market

  Current Estimated Value $658,459

  Last Listing Agent Barbara Bowers Preferred Properties (KW)

  651 William St Unit 1, Key West, FL 33040
• 

  

  /27

  Not Listed For Sale

  6000 Peninsular Ave Unit B1-L2-74, Stock Island, FL 33040

  • Built 2007

  6000 Peninsular Ave Unit B1-L2-74, Stock Island, FL 33040

  Last Sold Summary

  • 98 Days On Market
• 

  

  /9

  $899,000

  • Land
  • 12,000 Sq Ft
  • $3,263,370 per Acre

  24764 Overseas Hwy, Summerland Key, FL 33042

  Rare opportunity in the heart of Summerland Key, two contiguous waterfront lots totaling 12,000 SF in the SC (Suburban Commercial) zoning district. Offering over 120 feet of premium frontage - both on the highly visible Overseas Highway and on deep-water accessible oceanside canal - this property delivers exceptional visibility and flexible commercial potential. 120' concrete dockage with direct

  

  Stacy Shahan

  Island Real Estate Company Florida Keys

  (786) 952-6715

  24764 Overseas Hwy, Summerland Key, FL 33042
• 

  

  /8

  $3,250 Per Month

  • 2 Beds
  • 1 Bath
  • 756 Sq Ft
  • Waterfront Island Living at Staples Duplex

  2627 Staples Ave Unit A, Key West, FL 33040

  Experience the relaxed side of Key West living from this canal-front duplex with access to both the Gulf and Atlantic. Enjoy off-street parking, nearby bike paths, easy access to beaches, waterfront restaurants, grocery stores, and all the everyday conveniences that make island life easy.Perfectly positioned in a quiet neighborhood close enough to enjoy Old Town and Duval Street, while

  2627 Staples Ave Unit A, Key West, FL 33040
• 

  

  /61

  $592,000

  Sold May 29, 2026

  29951 Pine Channel Rd, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 912 Sq Ft
  • Built 1989

  Last Sold Summary

  • 9% Below List Price
  • $649/SF
  • 80 Days On Market

  Current Estimated Value $594,770

  Last Listing Agent Lindsay Ryan EXP Realty LLC

  29951 Pine Channel Rd, Big Pine Key, FL 33043
• 

  

  /28

  Est $661,540

  Not Listed For Sale

  3314 Northside Dr Unit 103, Key West, FL 33040

  • 3 Beds
  • 2.5 Baths
  • 1,270 Sq Ft
  • Built 1986

  3314 Northside Dr Unit 103, Key West, FL 33040

  Last Sold Summary

  • 65 Days On Market
• 

  

  /33

  $1,150,000

  • 2 Beds
  • 1.5 Baths
  • 1,091 Sq Ft

  709 Chapman Ln, Key West, FL 33040

  Tucked away on a quiet lane in Old Town Key West, this historic island home offers a rare combination of architectural character, elevated location, and walkable convenience. Positioned in the desirable X-flood zone near the highest natural elevation on the island, the property sits just steps from the energy of Duval Street while maintaining a peaceful residential feel. Originally constructed

  

  Terrance Sullivan

  Ocean Sotheby's International Realty

  (645) 220-2812

  709 Chapman Ln, Key West, FL 33040
• 

  

  /86

  $28,000 Per Month

  • 6 Beds
  • 6.5 Baths
  • 4,108 Sq Ft
  • House for Rent

  146 Mockingbird Rd, Islamorada, FL 33070

  Spectacular waterfront residence built in 2021 showcasing exceptional craftsmanship and high-quality materials throughout. This three-story coastal retreat offers 6 bedrooms and 6.5 bathrooms and is perfectly positioned facing west, capturing breathtaking sunset Gulf views while offering enhanced privacy with no rear neighbors. The first floor features a private guest suite, living area with

  Nancy Jimenez Douglas Elliman

  146 Mockingbird Rd, Islamorada, FL 33070
• 

  /2

  $260,000

  Sold Nov 03, 2025

  94825 Overseas Hwy #265, Key Largo, FL 33037

  • Land
  • 1,655 Sq Ft
  • $6,842,105 per Acre

  Last Sold Summary

  • 26% Below List Price
  • 188 Days On Market

  Current Estimated Value $462,378

  Last Listing Agent Orian Levy Cromwell & Forbes Inc

  94825 Overseas Hwy #265, Key Largo, FL 33037
• 

  

  /37

  Not Listed For Sale

  27883 Coral Shores Rd, Little Torch Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 720 Sq Ft
  • Built 1973

  27883 Coral Shores Rd, Little Torch Key, FL 33042

  Last Sold Summary

  • 9 Days On Market
• 

  

  /77

  $12,999,999

  $1M PRICE DROP

  • 31 Beds
  • 19 Baths

  21470 Overseas Hwy, Cudjoe Key, FL 33042

  Located on Cudjoe Key, only 20 miles from Key West. Transient use property, over 3.5 acres, 15 units (15 ROGO exemptions), over 300 feet of water frontage, boat basin, 3 concrete docks, one wooden dock, boat ramp. Shared coin laundry, 2 swimming pools, 3 private driveways. 2 parcels on US 1 are zoned Sub Urban Commercial, excellent rental history. Property spans from US 1 to the Atlantic Ocean.

  

  Jennifer Weeks

  Select Properties of NWFL

  (786) 882-8127

  21470 Overseas Hwy, Cudjoe Key, FL 33042
• 

  

  /19

  $3,000 Per Month

  • 2 Beds
  • 2 Baths
  • 803 Sq Ft
  • Las Salinas 2 Bedroom 2 Bathroom

  3930 S Roosevelt Blvd, Key West, FL 33040

  This 2 bedroom 2 bathroom condo is located in Las Salinas. This unit has a central ac unit and stackable washer/dryer unit appliances including a fridge, oven and dishwasher. There is a shared pool at this complex. There is one assigned parking space.

  3930 S Roosevelt Blvd, Key West, FL 33040
• 

  

  /48

  $525,000

  Sold Feb 19, 2026

  357 23rd St, Marathon, FL 33050

  • 2 Beds
  • 1 Bath
  • 1,010 Sq Ft
  • Built 1958

  Last Sold Summary

  • 16% Below List Price
  • $520/SF
  • 98 Days On Market

  Current Estimated Value $547,559

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

  357 23rd St, Marathon, FL 33050
• 

  

  /17

  Est $960,955

  Not Listed For Sale

  33 Flamingo Hammock Rd, Islamorada, FL 33036

  33 Flamingo Hammock Rd, Islamorada, FL 33036

  Last Sold Summary

  • 92 Days On Market
• 

  

  /43

  $489,000

  • 1 Bed
  • 1 Bath
  • 577 Sq Ft

  500 Burton Dr Unit 2313, Tavernier, FL 33070

  Updated 1/1 with nice Ocean Views , great rental income too. This condo Grossed $21,025.61 in the first Quarter of 2025. Owner and friends used it a lot too as there are no restrictions on an owners use. Impact sliders & Doors. Being sold fully furnished with Housewares. Fiber optic WIFI that is quick and secured. Direct Ocean access marina that is naturally protected. Lighted tennis & pickle

  

  Tom Rodriguez

  American Caribbean Real Estate, Christie's International Real Estate

  (786) 882-9229

  500 Burton Dr Unit 2313, Tavernier, FL 33070
• 

  

  /37

  $3,400 Per Month

  • 2 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Property for Rent

  806 S Jade Dr, Key Largo, FL 33037

  AVAILABLE AUGUST 5TH, 2026! Welcome to your perfect retreat in the heart of Key Largo! Golf cart in photos included! Located in the vibrant 55+ community of Silver Shores, this fully furnished 2-bedroom, 2-bathroom home features tasteful modern coastal decor and an inviting open-concept layout. The spacious living room, kitchen, and dining area flow seamlessly together for comfortable everyday

  Jessie Cruz Lifestyle International Realty

  806 S Jade Dr, Key Largo, FL 33037
• 

  

  /35

  $1,180,000

  Sold Sep 17, 2025

  12399 Overseas Hwy Unit 24, Marathon, FL 33050

  • 3 Beds
  • 2.5 Baths
  • 1,440 Sq Ft
  • Built 2007

  Last Sold Summary

  • 7% Below List Price
  • $819/SF
  • 289 Days On Market

  Last Listing Agent Jessica Borraccino Coldwell Banker Schmitt Real Estate Co.

  12399 Overseas Hwy Unit 24, Marathon, FL 33050
• 

  

  /44

  Est $852,278

  Not Listed For Sale

  6800 Maloney Ave Unit 8, Stock Island, FL 33040

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft
  • Built 2014

  6800 Maloney Ave Unit 8, Stock Island, FL 33040

  Last Sold Summary

  • 43 Days On Market
• 

  

  /18

  $4,195

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft

  1916 Staples Ave, Key West, FL 33040

  ANNUAL RENTAL! Available JUNE 1st. The perfect Key West classic cottage with all the modern features! Perfectly located just short bike ride to Old Town or distance to the island's major shopping centers. Gated entry and fenced in. Large storage area in backyard, Gas BBQ grill for cookouts and sundeck. Has Washer/dryer in rear utility room. Nicely appointed interior fully furnished with a coastal

  

  Christian Loffreno

  Loffreno Real Estate

  (786) 686-9482

  1916 Staples Ave, Key West, FL 33040
• 

  

  /6

  $3,250 Per Month

  • 2 Beds
  • 1 Bath
  • 756 Sq Ft
  • Waterfront Island Living at Staples Duplex

  2627 Staples Ave Unit B, Key West, FL 33040

  Experience the relaxed side of Key West living from this canal-front duplex with access to both the Gulf and Atlantic. Enjoy off-street parking, nearby bike paths, easy access to beaches, waterfront restaurants, grocery stores, and all the everyday conveniences that make island life easy.Perfectly positioned in a quiet neighborhood close enough to enjoy Old Town and Duval Street, while

  2627 Staples Ave Unit B, Key West, FL 33040
• 

  

  /30

  $1,800,000

  Sold Jul 08, 2025

  214 Fleming St, Key West, FL 33040

  • 2 Beds
  • 2.5 Baths
  • 1,312 Sq Ft
  • Built 1995

  Last Sold Summary

  • 8% Below List Price
  • $1,372/SF
  • 136 Days On Market

  Current Estimated Value $1,850,609

  Last Listing Agent Rodney Culiver Last Key Realty, Inc (KW)

  214 Fleming St, Key West, FL 33040
• 

  

  /26

  Est $876,674

  Not Listed For Sale

  827 Baptist Ln Unit 1 and 2, Key West, FL 33040

  • 4 Beds
  • 2 Baths
  • 1,374 Sq Ft
  • Built 1923

  827 Baptist Ln Unit 1 and 2, Key West, FL 33040

  Last Sold Summary

  • 117 Days On Market
• 

  

  /30

  $725,000

  • 2 Beds
  • 1.5 Baths
  • 1,007 Sq Ft

  8 S Andros Rd, Key Largo, FL 33037

  Concrete home on TWO fenced lots with a Garage !! Ground level home with a newer ( 2018) metal roof on High elevation , was X flood zone, with flood insurance only costing $670.00 a year. Updated kitchen with wood cabinetry and stainless steel appliances. 12,000sq.ft. lot with storage and secured rolling gate entrance, plenty of boat trailer storage, parking and room for a pool. Close to Buzzards

  

  Tom Rodriguez

  American Caribbean Real Estate, Christie's International Real Estate

  (877) 346-8162

  8 S Andros Rd, Key Largo, FL 33037
• 

  /2

  $2,600 Per Month

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

  710 Barcelona Rd Unit Bottom, Key Largo, FL 33037

  WONDERFUL 2/1 ALL UTILITIES INCLUDED NO HOA IN KEY LARGO.

  Roger Schaeffler Florida Realty of Miami Corp

  710 Barcelona Rd Unit Bottom, Key Largo, FL 33037
• 

  

  /29

  $377,500

  Sold Nov 20, 2025

  119 Cortez Dr Unit 1G, Islamorada, FL 33036

  • 1 Bed
  • 1 Bath
  • 518 Sq Ft
  • Built 1980

  Last Sold Summary

  • 2% Below List Price
  • $729/SF
  • 24 Days On Market

  Last Listing Agent Krissy Carnahan Realty ONE Group Destination (ISL)

  119 Cortez Dr Unit 1G, Islamorada, FL 33036
• 

  

  /28

  Est $687,040

  Not Listed For Sale

  88181 Old Hwy Unit F4 slip 65, Islamorada, FL 33036

  • 2 Beds
  • 2 Baths
  • 1,330 Sq Ft
  • Built 1979

  88181 Old Hwy Unit F4 slip 65, Islamorada, FL 33036

  Last Sold Summary

  • 102 Days On Market
• 

  

  /49

  $1,399,000

  $200K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,508 Sq Ft

  21250 Conch Dr, Cudjoe Key, FL 33042

  Discover a serene escape nestled in the heart of the Lower Florida Keys. Located in Cudjoe Cove, a boutique gated community of just nine homes, this 3-bedroom, 2-bath conch cottage offers unbeatable views and direct access to the ocean. Built of durable concrete with a standing seam metal roof and impact-rated windows, the home is designed for coastal resilience. A long tropical walkway leads you

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (855) 959-3732

  21250 Conch Dr, Cudjoe Key, FL 33042
• 

  

  /27

  $4,900 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,804 Sq Ft
  • House for Rent

  94825 Overseas Hwy Unit 237, Key Largo, FL 33037

  Only at Key Largo Ocean Resort can you be close to the bay and minutes from all. Your 1800+ ft luxury vacation property has been meticulously and elegantly presented with dramatic large living spaces, fabulous Chef’s kitchen, tile floors thru-out with lux master and spa bath. All-inclusive and fully equipped in every way imaginable with the best of everything to enjoy true resort style living.

  Gustavo Lopez Village Realty of S. Florida

  94825 Overseas Hwy Unit 237, Key Largo, FL 33037
• 

  

  /45

  $780,000

  Sold Jul 18, 2025

  29025 Geranium Dr, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 912 Sq Ft
  • Built 1981

  Last Sold Summary

  • 6% Below List Price
  • $855/SF
  • 44 Days On Market

  Current Estimated Value $793,747

  Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.

  29025 Geranium Dr, Big Pine Key, FL 33043
• 

  

  /23

  Not Listed For Sale

  40 Ed Swift Rd, Key West, FL 33040

  • 2 Beds
  • 1 Bath
  • 714 Sq Ft
  • Built 1977

  40 Ed Swift Rd, Key West, FL 33040

  Last Sold Summary

  • 20 Days On Market
• 

  

  /54

  $3,200,000

  $799K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 3,222 Sq Ft

  82 Tingler Ln, Marathon, FL 33050

  Sprawling Sombrero Beach newly renovated retreat on an oversized lot with pool, private sandy beach and Open Water Views! Currently utilized as a successful vacation rental this home boasts loads of space and elevated amenities for a family or income-producing investment opportunity! An expansive dock allows for shallow draft boating, kayaking and paddle boarding adventures with ease, just

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (645) 233-3736

  82 Tingler Ln, Marathon, FL 33050
• 

  

  /30

  $20,000 Per Month

  • 5 Beds
  • 4.5 Baths
  • House for Rent

  128 Leoni Dr, Islamorada, FL 33036

  SPECTACULAR VENETIAN SHORES HOME! 70' concrete dock on deep water canal which opens directly to Snake Creek for quick and easy access to bay or ocean; Furnished; 5 bedrooms/4.5 baths; private master retreat with gorgeous bath on third level; marble floors throughout; elevator; FABULOUS chef's kitchen with Wolf gas range and huge island; large terraces and fantastic entertaining spaces; Sonos

  Emily Romberg Real Estate Sales Force - Coral Gables

  128 Leoni Dr, Islamorada, FL 33036
• 

  

  /43

  $2,595,000

  Sold Aug 13, 2025

  412 122nd Street Gulf, Marathon, FL 33050

  • 3 Beds
  • 2.5 Baths
  • 2,391 Sq Ft
  • Built 2008

  Last Sold Summary

  • 6% Below List Price
  • $1,085/SF
  • 100 Days On Market

  Current Estimated Value $2,711,967

  Last Listing Agent Natalie Ardis Coldwell Banker Schmitt Real Estate Co.

  412 122nd Street Gulf, Marathon, FL 33050
• 

  

  /8

  Not Listed For Sale

  1550 Ocean Bay Dr Unit 42, Key Largo, FL 33037

  • 1 Bed
  • 45 Sq Ft
  • Built 1990

  1550 Ocean Bay Dr Unit 42, Key Largo, FL 33037

  Last Sold Summary

  • 8 Days On Market

Showing Results 441 - 480, Page 12 of 18