Cudjoe Key, FL Homes

• 

  

  

  /115

  Est $6,772,577

  Not Listed For Sale

  785 Sawyer Dr, Cudjoe Key, FL 33042

  • 7 Beds
  • 6 Baths
  • 4,888 Sq Ft
  • Built 2019

  785 Sawyer Dr, Cudjoe Key, FL 33042

  Last Sold Summary

  • 44 Days On Market

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co
• 

  

  

  /60

  $799,000

  $88K PRICE DROP Under Contract

  • 2 Beds
  • 1 Bath
  • 806 Sq Ft

  701 Spanish Main Dr Unit 49, Cudjoe Key, FL 33042

  ********Nightly Licensed Transient Rental!!!********This amazing, two bedroom / one bathroom, open water front views , nightly transient rental is ready for you to enjoy both the beauty of this location and the income off the nightly rental license. The floor plan makes the open water views as its main focus. Cook the catch of the day overlooking the waters that you just caught that

  Bobby Coe RE/MAX Keys Connection (KW)

  701 Spanish Main Dr Unit 49, Cudjoe Key, FL 33042
• 

  

  

  /30

  $430,000

  Sold May 11, 2026

  21857 Disturbed Pine Rd, Summerland Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 415 Sq Ft
  • Built 1975

  Last Sold Summary

  • $1,036/SF
  • 94 Days On Market

  Current Estimated Value $454,125

  Last Listing Agent Rose Dell Keller Williams Key West Compass Realty

  21857 Disturbed Pine Rd, Summerland Key, FL 33042
• 

  

  

  /40

  Est $2,271,753

  Not Listed For Sale

  20995 2nd Ave W, Summerland Key, FL 33042

  • 3 Beds
  • 2.5 Baths
  • 2,184 Sq Ft
  • Built 2007

  20995 2nd Ave W, Summerland Key, FL 33042

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co
• 

  

  

  /41

  $949,000

  • 3 Beds
  • 2 Baths
  • 1,144 Sq Ft

  342 Spanish Main Dr, Summerland Key, FL 33042

  Welcome to 342 Spanish Main Drive, a beautiful canal-front home in the heart of Cudjoe Key, offering the perfect combination of waterfront living, modern comfort, and laid-back Florida Keys charm. This two-story residence features 3 bedrooms and 2 full bathrooms, thoughtfully designed for both everyday living and relaxing island escapes. The bright, open interior is move-in ready and includes a

  Monika Rydzak eXp Realty LLC KW Branch

  342 Spanish Main Dr, Summerland Key, FL 33042
• 

  

  /41

  $2,280,000

  Sold Apr 02, 2026

  1176 Thatch Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,577 Sq Ft
  • Built 1984

  Last Sold Summary

  • 24% Below List Price
  • $1,446/SF
  • 359 Days On Market

  Current Estimated Value $2,321,792

  Last Listing Agent Jonathan Minerick Homecoin.com

  1176 Thatch Ln, Summerland Key, FL 33042
• 

  

  /57

  Est $1,459,721

  Not Listed For Sale

  468 Sawyer Dr, Summerland Key, FL 33042

  • 4 Beds
  • 4 Baths
  • 1,797 Sq Ft
  • Built 1972

  468 Sawyer Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 215 Days On Market

  Last Listing Agent Stacy Shahan Island Real Estate Company Florida Keys
• 

  

  /31

  $982,600

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  701 Spanish Main Dr Unit 198, Cudjoe Key, FL 33042

  Welcome to Oceanview Serenity, an exceptional, open-water retreat located in the gated community of Venture Out at Cudjoe Key (Mile Marker 23). This completely renovated 2-bedroom, 2-bathroom mid-rise offers rare, unobstructed turquoise ocean views as if you are floating on the water. A true boater's paradise, the property boasts a massive concrete seawall with effortless deep-water access.

  Jonathan Minerick Homecoin.com

  701 Spanish Main Dr Unit 198, Cudjoe Key, FL 33042
• 

  

  /62

  $1,000,000

  Sold Aug 06, 2026

  165 Cutlass Ln, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,448 Sq Ft
  • Built 1991

  Last Sold Summary

  • $408/SF
  • 0 Days On Market

  Current Estimated Value $1,292,510

  Last Listing Agent Justyn Ewald Expert Realty LLC (HQ)

  165 Cutlass Ln, Summerland Key, FL 33042
• 

  

  /19

  Est $886,071

  Not Listed For Sale

  221 Cutthroat Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1985

  221 Cutthroat Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 498 Days On Market

  Last Listing Agent Melva Wagner Century 21 Prestige Realty Gro
• 

  

  /61

  $639,000

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  701 Spanish Main Dr Unit 495, Cudjoe Key, FL 33042

  Spectacular peekaboo open water views abound with this updated 2 bed/2 bath canal front home with 35 foot seawall. Located in a gated community with tons of amenities. New kitchen w/Caesar quartz countertops, full backsplash, new stainless steel appliances, Koehler sink, modern, white cabinets with an abundance of storage, including a large center Island. Open concept floor plan with open water

  Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 495, Cudjoe Key, FL 33042
• 

  

  /4

  $837,000

  Sold Jul 10, 2026

  701 Spanish Main Dr Unit 51, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 888 Sq Ft
  • Built 2000

  Last Sold Summary

  • 7% Below List Price
  • $943/SF
  • 37 Days On Market

  Last Listing Agent Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 51, Cudjoe Key, FL 33042
• 

  

  /81

  Est $1,281,987

  Not Listed For Sale

  23041 Snapper Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,664 Sq Ft
  • Built 1992

  23041 Snapper Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 11 Days On Market

  Last Listing Agent Tommy Mack Coastal Collection Real Estate Inc.
• 

  

  /72

  $595,000

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  701 Spanish Main Dr Unit 604, Cudjoe Key, FL 33042

  Owner says ''Bring All Offers''Charming Coastal Retreat: 2 Bedroom, 2 Bath home with 35' concrete seawall. Nightly Rentals allowed.Welcome to your perfect getaway or investment opportunity! This delightful home built in 1993, offers 816 sq. ft. of comfortable living space, fully furnished and turn-key, making it an ideal choice for both relaxation and income generation. Step inside to discover a

  Lanny Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 604, Cudjoe Key, FL 33042
• 

  

  /42

  $920,000

  Sold Jun 18, 2026

  22954 Buccaneer Ln, Cudjoe Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1990

  Last Sold Summary

  • 8% Below List Price
  • $657/SF
  • 30 Days On Market

  Current Estimated Value $923,547

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  22954 Buccaneer Ln, Cudjoe Key, FL 33042
• 

  /2

  Est $873,811

  Not Listed For Sale

  22910 Privateer Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft
  • Built 1988

  22910 Privateer Dr, Summerland Key, FL 33042
• 

  

  /45

  $1,269,000

  • 2 Beds
  • 2 Baths
  • 1,100 Sq Ft

  116 Spanish Main Dr, Summerland Key, FL 33042

  Discover your personal island sanctuary in the heart of Cudjoe Key, where every day feels like Margaritaville. This stunning 2-bedroom, 2-bathroom single-family home has been thoughtfully updated to offer the ultimate waterfront lifestyle, featuring a sleek kitchen with a central island, 2025 updated appliances and two beautifully remodeled bathrooms. The interior glows with natural light,

  Tina Fingerman Beaches MLS

  116 Spanish Main Dr, Summerland Key, FL 33042
• 

  

  /37

  $830,000

  Sold Jun 10, 2026

  153 Peg Leg Ln, Cudjoe Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,203 Sq Ft
  • Built 1997

  Last Sold Summary

  • 8% Below List Price
  • $690/SF
  • 91 Days On Market

  Current Estimated Value $849,863

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  153 Peg Leg Ln, Cudjoe Key, FL 33042
• 

  

  /34

  Est $955,384

  Not Listed For Sale

  320 Spanish Main Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1989

  320 Spanish Main Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 18 Days On Market

  Last Listing Agent Sean Farrer Coldwell Banker Schmitt Real Estate Co. (KW)
• 

  

  /41

  $590,000

  $200K PRICE DROP Pending

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft

  22920 Privateer Dr, Summerland Key, FL 33042

  Following a monumental $200,000 price drop, this rare waterfront opportunity is available at an unbeatable price point. Launch your boat from your backyard for world-class access to the Atlantic Ocean and Gulf of Mexico. Unlock instant equity with virtual additions in the photos and below-market pricing; there is significant room to secure this property way below market value after completing

  Jeff Shapiro Global Luxury Realty LLC

  22920 Privateer Dr, Summerland Key, FL 33042
• 

  

  /42

  $775,000

  Sold Oct 01, 2025

  22988 Port Royal Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,122 Sq Ft
  • Built 1998

  Last Sold Summary

  • 6% Below List Price
  • $691/SF
  • 68 Days On Market

  Current Estimated Value $795,576

  Last Listing Agent Walter Ceballos, P.A. Berkshire Hathaway HomeServices Keys Real Estate

  22988 Port Royal Ln, Summerland Key, FL 33042
• 

  

  /37

  Est $931,525

  Not Listed For Sale

  139 Le Grand Ln, Summerland Key, FL 33042

  • 3 Beds
  • 1 Bath
  • 1,300 Sq Ft
  • Built 1994

  139 Le Grand Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 48 Days On Market

  Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.
• 

  

  /43

  $2,060,000

  • 5 Beds
  • 3 Baths
  • 1,978 Sq Ft

  94 Sacarma Dr, Cudjoe Key, FL 33042

  Rare Licensed Oceanfront Short-Term Vacation Rental in the Lower Florida Keys, with SELLER FINANCING OFFERED! Welcome to Fandango, a highly successful transient (daily-weekly) vacation rental home offering an exceptional investment opportunity and a personal retreat. This stunning 5-bedroom, 3-bathroom property, built in 2011 and expanded in 2018, was thoughtfully designed as the ultimate family

  Michelle Blades Realty Executives Florida Keys Old Town

  94 Sacarma Dr, Cudjoe Key, FL 33042
• 

  

  /52

  $2,300,000

  Sold Sep 12, 2025

  23086 Snapper Ln, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,586 Sq Ft
  • Built 1985

  Last Sold Summary

  • 8% Below List Price
  • $889/SF
  • 147 Days On Market

  Current Estimated Value $2,244,810

  Last Listing Agent Greg MacLaren Internet Realty of the Florida Keys

  23086 Snapper Ln, Summerland Key, FL 33042
• 

  

  /27

  Est $1,658,697

  Not Listed For Sale

  22836 Port Royal Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,406 Sq Ft
  • Built 1987

  22836 Port Royal Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Sandra Tuttle American Caribbean Real Estate Lower Keys
• 

  

  /64

  $1,499,000

  • 3 Beds
  • 3 Baths
  • 1,596 Sq Ft

  21007 4th Ave, Summerland Key, FL 33042

  Wake up to breathtaking Florida Keys sunrises from this exceptional oceanside waterfront home in Cudjoe Key. Offering 1,596 square feet of living space on an 8,920-square-foot lot, this CBS-built residence features 3 bedrooms and 3 bathrooms, + Office/beddroom,combining durability, comfort, and the relaxed island lifestyle you've been dreaming of.Designed for both everyday living and

  Diane Corliss Coldwell Banker Schmitt RE Co.

  21007 4th Ave, Summerland Key, FL 33042
• 

  

  /29

  $1,400,000

  Sold Apr 24, 2026

  20841 8th Ave W, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,872 Sq Ft
  • Built 1994

  Last Sold Summary

  • 10% Below List Price
  • $748/SF
  • 82 Days On Market

  Current Estimated Value $1,459,775

  Last Listing Agent Collin Tingle Coldwell Banker Schmitt Lower Keys (KW)

  20841 8th Ave W, Summerland Key, FL 33042
• 

  

  /45

  Est $2,072,010

  Not Listed For Sale

  20942 6th Ave W, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 2,772 Sq Ft
  • Built 1994

  20942 6th Ave W, Summerland Key, FL 33042

  Last Sold Summary

  • 42 Days On Market

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co
• 

  

  /45

  $493,000

  $36K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 758 Sq Ft

  701 Spanish Main Dr Unit 417, Cudjoe Key, FL 33042

  MINI LOBSTER SEASON PRICE REDUCTION!!! Price DROPPED AGAIN below 500k! This is THE lowest 2BR/BA priced home in Venture Out on Cudjoe Key! MOTIVATED SELLER! Turn-key 2BR/2BA waterfront fully furnished home with 35' concrete dock and patio furniture included, Front door paver patio, impact slider doors and windows, gas stove, and ample storage including outdoor dock box. Enjoy direct, deep-water

  Amanda Taylor Bluescape Real Estate

  701 Spanish Main Dr Unit 417, Cudjoe Key, FL 33042
• 

  

  /17

  $16,000

  Sold Oct 28, 2025

  0 Budd Key Aly Unit 616603, Cudjoe Key, FL 33042

  • Land
  • 1.2 Acres
  • $13,333 per Acre

  Last Sold Summary

  • 23% Below List Price
  • 12 Days On Market

  Last Listing Agent Bobby Coe RE/MAX Keys Connection (KW)

  0 Budd Key Aly Unit 616603, Cudjoe Key, FL 33042
• 

  

  /74

  Est $3,246,909

  Not Listed For Sale

  22572 Jolly Roger Dr, Summerland Key, FL 33042

  • 6 Beds
  • 4 Baths
  • 3,225 Sq Ft
  • Built 1963

  22572 Jolly Roger Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 313 Days On Market

  Last Listing Agent Jan Fritz Coldwell Banker Schmitt RE Co.
• 

  

  /49

  $755,000

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft

  19543 Navajo St, Cudjoe Key, FL 33042

  3 bed 2 bath stilt home built in 2018 in sought after Sugarloaf Key. Open concept floor plan, large kitchen with an abundance of large white cabinets, kitchen island overlooking living area, stainless steel appliances, light and stylish colors throughout. Wood-look tile plank flooring, crown molding, 9-ft ceilings, recessed lighting and ceiling fans in all bedrooms and living room. Full size

  Pamela Stangler Expert Realty LLC

  19543 Navajo St, Cudjoe Key, FL 33042
• 

  

  /47

  $1,800,000

  Sold Apr 30, 2026

  23087 Sailfish Ln, Cudjoe Key, FL 33042

  • 3 Beds
  • 3.5 Baths
  • 2,100 Sq Ft
  • Built 1997

  Last Sold Summary

  • 10% Below List Price
  • $857/SF
  • 48 Days On Market

  Current Estimated Value $1,780,967

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  23087 Sailfish Ln, Cudjoe Key, FL 33042
• 

  

  /40

  Est $1,082,077

  Not Listed For Sale

  22983 Anne Bonny Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,320 Sq Ft
  • Built 1986

  22983 Anne Bonny Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 109 Days On Market

  Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.
• 

  

  /6

  $1,775,000

  • 4 Beds
  • 4 Baths
  • 1,671 Sq Ft

  193 Galleon Ln, Cudjoe Key, FL 33042

  Brand new waterfront in the Keys, built for you from the ground up. This is a preconstruction home in Cutthroat Harbor Estates. You buy now and it gets built for you, delivered turnkey. Picture it: your boat at the private dock on approx. 102 ft of canal seawall, a pool and jacuzzi below, coffee on the rooftop deck. Elevated 4 bed, 4 bath, outdoor kitchen, solar and efficient systems, brand new

  Joaquin Merlo-Garzon CRANELUXE

  193 Galleon Ln, Cudjoe Key, FL 33042
• 

  

  /36

  $840,000

  Sold Jun 26, 2026

  701 Spanish Main Dr Unit 512, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 861 Sq Ft
  • Built 1999

  Last Sold Summary

  • 14% Below List Price
  • $976/SF
  • 159 Days On Market

  Last Listing Agent Jamie Caudill Lokation Real Estate

  701 Spanish Main Dr Unit 512, Cudjoe Key, FL 33042
• 

  /2

  Est $2,504,530

  Not Listed For Sale

  20820 7th Ave W, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 2,000 Sq Ft
  • Built 1972

  20820 7th Ave W, Summerland Key, FL 33042
• 

  

  /48

  $1,399,000

  $100K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,434 Sq Ft

  22939 Gasparilla Ln, Summerland Key, FL 33042

  Welcome to your ROOFTOP RETREAT - a beautifully remodeled waterfront home at 22939 Gasparilla Lane in Cudjoe Key, where panoramic ocean views and relaxed Keys elegance come together in perfect harmony. From the spectacular rooftop deck to the light-filled interior, shimmering turquoise water creates a breathtaking backdrop throughout the home.This thoughtfully updated 3-bedroom, 2-bath

  Donna Pezzi Keller Williams Key West Compass Realty

  22939 Gasparilla Ln, Summerland Key, FL 33042
• 

  

  /90

  $1,075,000

  Sold May 11, 2026

  21855 Spain Blvd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,467 Sq Ft
  • Built 1985

  Last Sold Summary

  • 10% Below List Price
  • $733/SF
  • 28 Days On Market

  Current Estimated Value $1,079,435

  Last Listing Agent Patti Nickless Coldwell Banker Schmitt Lower Keys (KW)

  21855 Spain Blvd, Summerland Key, FL 33042
• 

  

  /68

  Est $2,649,539

  Not Listed For Sale

  531 Seminole Dr, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,604 Sq Ft
  • Built 1985

  531 Seminole Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 57 Days On Market

  Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

Showing Results 121 - 160, Page 4 of 18