Monroe County, FL Homes

• 

  

  

  /60

  $2,499,000

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

  Unlisted Address

  Experience modern waterfront living at this exceptional 2-bed, 2.5-bath oceanfront home on Geiger Key, where contemporary design meets exceptional engineering. Envisioned by original owner and renowned author Reese Palley, the residence was designed to maximize breathtaking open-water views, natural light, and indoor-outdoor living. Remote-controlled blinds reveal an endless blue horizon, while

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real E

  Unlisted Address
• 

  

  

  /30

  $5,300 Per Month

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft
  • House for Rent

  932 Tropical Ln, Key Largo, FL 33037

  Furnished seasonal rental, available October through March. Perched at the tip of its own peninsula in Key Largo's Cross Key Waterways, this 3-bed, 2-bath, 1,440 sq ft canal-front retreat is surrounded by water on nearly every side. Boats dock steps from the door, and even the kitchen sink looks out over palm trees and passing boats — do the dishes with a view you won't want to look away from. A

  

  Ashley Kettner

  Compass Florida LLC

  932 Tropical Ln, Key Largo, FL 33037
• 

  

  

  /62

  $1,500,000

  Sold Aug 10, 2026

  22410 Jolly Roger Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,587 Sq Ft
  • Built 1982

  Last Sold Summary

  • $945/SF
  • 10 Days On Market

  Current Estimated Value $1,674,544

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  22410 Jolly Roger Dr, Summerland Key, FL 33042
• 

  

  

  /55

  Not Listed For Sale

  307 King Ave, Key Largo, FL 33037

  • 3 Beds
  • 2 Baths
  • 912 Sq Ft
  • Built 1971

  307 King Ave, Key Largo, FL 33037

  Last Sold Summary

  • 30 Days On Market

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

  

  

  /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
• 

  

  /34

  Starting at $2,999 Per Month

  • 1 - 3 Beds

  96 Coco Plum Dr, Marathon, FL 33050

  CoCo Vista

  

  96 Coco Plum Dr, Marathon, FL 33050
• 

  

  /43

  $500,000

  Sold Aug 26, 2026

  87200 Overseas Hwy Unit 6, Islamorada, FL 33036

  • 2 Beds
  • 1.5 Baths
  • 1,354 Sq Ft
  • Built 1980

  Last Sold Summary

  • 3% Above List Price
  • $369/SF
  • 44 Days On Market

  Current Estimated Value $492,396

  Last Listing Agent Jaclyn Kelley Prudential Keyswide Properties

  87200 Overseas Hwy Unit 6, Islamorada, FL 33036
• 

  

  /45

  Est $914,394

  Not Listed For Sale

  17338 Dolphin St E, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,875 Sq Ft
  • Built 1963

  17338 Dolphin St E, Summerland Key, FL 33042

  Last Sold Summary

  • 171 Days On Market

  Last Listing Agent Alexa Morgan Buy The Keys
• 

  

  /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
• 

  

  /39

  $5,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,598 Sq Ft
  • House for Rent

  9 Blue Water Dr, Key West, FL 33040

  Spacious 3 bedroom and 2 bathroom home for long term rental. High and dry Single family residence with extraordinary water views. This lot has ample off street parking, storage, a workshop, enclosed garage, Laundry room, and flex spaces. There is a large air conditioned shed in the back yard, perfect for an office or art studio.Landscaping and garbage service included.Applicants are

  

  Dustan Carpenter

  Berkshire Hathaway HomeServices Knight & Gardner Realty

  9 Blue Water Dr, Key West, FL 33040
• 

  

  /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 $380,600

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

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

  

  /35

  Not Listed For Sale

  1466 Overseas Hwy Unit 12, Marathon, FL 33050

  • Studio
  • 2,971 Sq Ft
  • Built 1975

  1466 Overseas Hwy Unit 12, Marathon, FL 33050

  Last Sold Summary

  • 254 Days On Market

  Last Listing Agent Lanny Gardner Bluescape Real Estate
• 

  

  /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 $2,750 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
• 

  

  /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 $943,171

  Last Listing Agent Matthew Sheehan Ocean Sotheby's International Realty

  60 Golf Club Dr, Key West, FL 33040
• 

  

  /18

  Est $693,538

  Not Listed For Sale

  139 Zane Grey Creek Dr, Long Key, FL 33001

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1987

  139 Zane Grey Creek Dr, Long Key, FL 33001

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Ginger Henderson Coldwell Banker Schmitt Real Estate Co.
• 

  

  /43

  $875,000

  $124K 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
• 

  

  /37

  $6,000 Per Month

  • 3 Beds
  • 4 Baths
  • 2,012 Sq Ft
  • House for Rent

  129 N Indies Dr, Duck Key, FL 33050

  Brand new construction for rent in the heart of Duck Key, FL, between Marathon and Islamorada. This newly built, single story 3 bedroom, 4 bathroom home features a split floor plan and a dedicated pool bathroom, with 10.8 foot ceilings, 8 foot solid doors, impact rated windows and doors, a one car garage, and a gourmet kitchen with marble countertops and premium finishes, plus a heated saltwater

  

  Joseph Suarez

  Trustpoint Realty, LLC

  129 N Indies Dr, Duck Key, FL 33050
• 

  

  /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
• 

  

  /29

  Est $993,227

  Not Listed For Sale

  511 9th St, Key Colony Beach, FL 33051

  • 2 Beds
  • 2 Baths
  • 1,260 Sq Ft
  • Built 1986

  511 9th St, Key Colony Beach, FL 33051

  Last Sold Summary

  • 101 Days On Market

  Last Listing Agent AIMEE KORNETTI Coldwell Banker Schmitt Real Estate Co.
• 

  

  /69

  $3,300,000

  $200K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,295 Sq Ft

  1083 Labat Ln, Cudjoe Key, FL 33042

  Experience elevated island living in this striking modern residence in Cudjoe Key, where sleek design meets the raw beauty of the Atlantic. This white contemporary home showcases a dramatic wall of glass along the oceanfront, creating a seamless connection between indoor living and the endless horizon beyond. The open-concept living space is flooded with natural light and anchored by breathtaking

  

  Sandra Tuttle

  Island Welcome Real Estate

  1083 Labat Ln, Cudjoe Key, FL 33042
• 

  

  /44

  $3,500

  Total Monthly Price

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

  901 White St Unit 2, Key West, FL 33040

  Available October 1. YEAR LEASE Beautiful Large one bedroom located in old town. COMPLETELY UPDATED THROUGHOUT. New custom bath, updated kitchen, new appliances, fixtures, fans, fresh paint throughout, hardwood floors. Open spacious unit meticulously upkept. Large private shaded front porch off second floor unit with furniture. Quiet building exceptionally maintained. Storage for bike in gated

  901 White St Unit 2, 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 $798,008

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

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

  

  /43

  Est $1,935,184

  Not Listed For Sale

  117 Sandy Cove Ave, Islamorada, FL 33036

  • 4 Beds
  • 3 Baths
  • 1,960 Sq Ft
  • Built 1964

  117 Sandy Cove Ave, Islamorada, FL 33036

  Last Sold Summary

  • 26 Days On Market

  Last Listing Agent Alina Davis Coldwell Banker Schmitt Islamorada
• 

  

  /50

  $2,195,000

  $255K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 1,725 Sq Ft

  1724 Bahama Dr, Key West, FL 33040

  This fully renovated canal front home at 1724 Bahama Drive offers modern waterfront living in a highly convenient location in Key West.The property features four bedrooms and four bathrooms and includes a separate mother in law unit, making it well suited for guests, extended family, or flexible use. The home has been completely updated with a new kitchen featuring quartz countertops,

  

  Dan Serban

  Key West Luxury Real Estate Inc (KW)

  1724 Bahama Dr, Key West, FL 33040
• 

  

  /86

  $15,000 Per Month

  • 4 Beds
  • 3 Baths
  • 2,638 Sq Ft
  • House for Rent

  108 W Plaza Del Lago, Islamorada, FL 33036

  Waterfront Islamorada Home with Private Beach Access & 75' Dock Experience the best of the Florida Keys in this waterfront home in Islamorada, accommodating up to 12 guests and perfect for family vacations, multigenerational gatherings, fishing adventures, or extended stays.Located on Lower Matecumbe Key, this 4-bedroom, 3-bath home offers 2,638 square feet of comfortable indoor-outdoor

  

  Victor Ruiz

  Move Miami, LLC.

  108 W Plaza Del Lago, 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 $2,671,303

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

  152 Giardino Dr, Islamorada, FL 33036
• 

  

  /3

  Not Listed For Sale

  351 46th St, Marathon, FL 33050

  • 2 Beds
  • 2 Baths
  • 768 Sq Ft
  • Built 1993

  351 46th St, Marathon, FL 33050

  Last Sold Summary

  • 413 Days On Market

  Last Listing Agent Bill Wilkinson Key to the Keys Real Estate, Inc
• 

  

  /70

  $12,500,000

  • 6 Beds
  • 7 Baths
  • 3,635 Sq Ft

  32 Sunset Key Dr, Key West, FL 33040

  A distinguished offering on one of Key West's most coveted private island enclaves, 32 Sunset Key Drive embodies the ease, elegance, and exclusivity of waterfront living. One of the largest custom residences on Sunset Key, this 3,635-square-foot oceanfront estate was conceived by its original owners with an unwavering commitment to craftsmanship, comfort, and detail. Set beside its own private

  

  J. Michael Caron

  Keller Williams Key West Compass Realty

  32 Sunset Key Dr, Key West, FL 33040
• 

  

  /20

  Starting at $3,299 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
• 

  

  /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 $1,063,800

  Last Listing Agent Jennifer Sylvia Keller Williams Key West Compass Realty

  29490 Ranger Ave, Big Pine Key, FL 33043
• 

  

  /17

  Est $497,255

  Not Listed For Sale

  44 7th Ave, Key West, FL 33040

  • 3 Beds
  • 2.5 Baths
  • 1,274 Sq Ft
  • Built 2007

  44 7th Ave, Key West, FL 33040

  Last Sold Summary

  • 8 Days On Market

  Last Listing Agent Monika Rydzak eXp Realty LLC KW Branch
• 

  

  /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

  

  Everett Smith

  Ocean Sotheby's International Realty

  1911 Seidenberg Ave, Key West, FL 33040
• 

  

  /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
• 

  

  /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 $428,156

  Last Listing Agent Milly Perez Seafarer Realty LLC

  10818 1st Avenue Gulf, Marathon, FL 33050
• 

  

  /26

  Est $846,473

  Not Listed For Sale

  620 Thomas St Unit 190, Key West, FL 33040

  • 2 Beds
  • 1 Bath
  • 604 Sq Ft
  • Built 1991

  620 Thomas St Unit 190, Key West, FL 33040

  Last Sold Summary

  • 198 Days On Market

  Last Listing Agent Paige Bethel Island Home Realty Inc.
• 

  

  /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
• 

  

  /35

  Starting at $2,451 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
• 

  

  /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
• 

  

  /75

  Est $1,205,337

  Not Listed For Sale

  11600 1st Avenue Gulf Unit 24, Marathon, FL 33050

  • 3 Beds
  • 2.5 Baths
  • 1,600 Sq Ft
  • Built 2006

  11600 1st Avenue Gulf Unit 24, Marathon, FL 33050

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Monica Barrett Coldwell Banker Schmitt Real Estate Co.

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