Homes in ZIP Code 33042

• 

  

  

  /72

  $3,899,000

  $100K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,096 Sq Ft

  17015 Wahoo Ln W, Sugarloaf Key, FL 33042

  Positioned on a rare west facing point lot with 270 ft of sparkling open water frontage on Sugarloaf Sound, this fully reimagined 3 Bedroom 3 Bathroom estate captures breathtaking sunset views across endless turquoise waters. Privately set on a gated 17,000 SF lot, the property lives like a private island compound framed by swaying palms, lush tropical landscaping, and the endless blue waters of

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (833) 754-7970

  17015 Wahoo Ln W, Sugarloaf Key, FL 33042
• 

  

  

  /29

  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

  (786) 640-1903

  

  21585 Overseas Hwy, Cudjoe Key, FL 33042
• 

  

  

  /27

  $837,000

  Sold Jul 11, 2025

  27417 Cayman Ln, Summerland Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 1,085 Sq Ft
  • Built 1975

  Last Sold Summary

  • 14% Below List Price
  • $771/SF
  • 274 Days On Market

  Current Estimated Value $878,121

  Last Listing Agent Karen Quist Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

  27417 Cayman Ln, Summerland Key, FL 33042
• 

  

  

  /41

  Est $1,033,868

  Not Listed For Sale

  366 Sawyer Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,390 Sq Ft
  • Built 1988

  366 Sawyer Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 4 Days On Market
• 

  

  

  /62

  $5,200,000

  • 4 Beds
  • 4 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 RE Co.

  (866) 531-8155

  17013 Coral Dr, Sugarloaf Key, FL 33042
• 

  

  /20

  Starting at $5,538 Per Month

  • 2 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

  (786) 730-7736

  

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

  

  /60

  $950,000

  Sold Oct 17, 2025

  76 W Shore Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,028 Sq Ft
  • Built 2001

  Last Sold Summary

  • 13% Below List Price
  • $924/SF
  • 369 Days On Market

  Current Estimated Value $926,012

  Last Listing Agent Cardenas & Krug Team Coastal Collection Real Estate Inc.

  76 W Shore Dr, Summerland Key, FL 33042
• 

  

  /58

  Est $2,075,247

  Not Listed For Sale

  22440 Jolly Roger Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,292 Sq Ft
  • Built 1988

  22440 Jolly Roger Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 85 Days On Market
• 

  

  /73

  $2,999,000

  • 3 Beds
  • 2 Baths
  • 2,170 Sq Ft

  17041 Marlin Dr, Sugarloaf Key, FL 33042

  Experience breathtaking sunsets over Sugarloaf Sound from this 2-story CBS open water estate offering 3 bedrooms, 2 baths, and 2,170 sq ft of elevated coastal living just 20 minutes from Key West. Situated on a generous 15,650 sq ft lot, this meticulously maintained home features impact doors and windows, metal roof, exterior elevator, and lush tropical landscaping including a dedicated orchid

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (855) 684-0921

  17041 Marlin Dr, Sugarloaf Key, FL 33042
• 

  

  /20

  $7,860

  Total Monthly Price

  • 3 Beds
  • 2 Baths
  • 1,431 Sq Ft
  • Condo for Rent

  886 Loggerhead Ln Unit SI ID1297829P, Summerland Key, FL 33042

  The advertised rate of $7,860/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 6, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

  (786) 833-8476

  886 Loggerhead Ln Unit SI ID1297829P, Summerland Key, FL 33042
• 

  /2

  $1,030,000

  Sold Nov 19, 2025

  22521 Jolly Roger Dr, Cudjoe Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 1,728 Sq Ft
  • Built 2010

  Last Sold Summary

  • $596/SF
  • 0 Days On Market

  Current Estimated Value $1,108,949

  Last Listing Agent Patti Nickless Coldwell Banker Schmitt RE Co.

  22521 Jolly Roger Dr, Cudjoe Key, FL 33042
• 

  

  /52

  Est $1,304,078

  Not Listed For Sale

  570 La Fitte Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 2,080 Sq Ft
  • Built 2020

  570 La Fitte Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 126 Days On Market
• 

  

  /5

  $285,000

  • Land
  • 1.01 Acres
  • $282,178 per Acre

  Unlisted Address

  Private Acre on Cudjoe Key. Lush, Tropical, and Near the Water Escape to your own secluded paradise in the Lower Keys! This just over an acre lot on Cudjoe Key is surrounded by beautiful equestrian properties and dense tropical foliage, offering unmatched privacy and tranquility. Located just seconds from a public boat ramp, you'll have easy access to world-class fishing, boating, and

  

  Coby Taylor

  Expert Realty LLC (HQ)

  (645) 219-1669

  Unlisted Address
• 

  

  /41

  $7,500 Per Month

  • 3 Beds
  • 2 Baths
  • 6,098 Sq Ft
  • House for Rent

  280 Airport Dr S, Summerland Key, FL 33042

  *** Private Airstrip *** Welcome to your slice of paradise in the Florida Keys! For aviation enthusiasts, the allure of this property is further enhanced by its location within a private airpark community (FD51 Summerland Key Airport). Nestled on a serene, clear wide canal with direct access to the Atlantic Ocean with no bridges, within a private airpark community, this home offers the

  Lisa Guirguis Genesis Realty Team

  280 Airport Dr S, Summerland Key, FL 33042
• 

  

  /56

  $1,725,000

  Sold Jul 11, 2025

  17159 Amberjack Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,660 Sq Ft
  • Built 1989

  Last Sold Summary

  • 14% Below List Price
  • $1,039/SF
  • 258 Days On Market

  Current Estimated Value $1,723,179

  Last Listing Agent Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty

  17159 Amberjack Ln, Summerland Key, FL 33042
• 

  

  /72

  Est $3,590,118

  Not Listed For Sale

  5460 Dorn Rd, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 2,134 Sq Ft
  • Built 1996

  5460 Dorn Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 30 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
• 

  

  /81

  $12,000 Per Month

  • 2 Beds
  • 2 Baths
  • 1,443 Sq Ft
  • House for Rent

  441 La Fitte Rd, Summerland Key, FL 33042

  ** SHORT-TERM RENTAL ** Stunning open water house with high ceilings, open floor plan, covered screen porch, and open deck for the sun lovers! New deck with a heavy-duty boat lift in place (15,000 pounds) in one of the cleanest waters in the FL Keys! Metal roof, New A/C, Water Heater, and a Front aluminum fence with beautiful landscaping This home is located in one of the best neighborhoods in

  Carolina Gil Caralex Intl Realty Group Corp

  441 La Fitte Rd, Summerland Key, FL 33042
• 

  

  /33

  $910,000

  Sold Apr 13, 2026

  151 Cutthroat Dr, Summerland Key, FL 33042

  • 2 Beds
  • 3 Baths
  • 1,140 Sq Ft
  • Built 1975

  Last Sold Summary

  • 4% Below List Price
  • $798/SF
  • 46 Days On Market

  Current Estimated Value $945,623

  Last Listing Agent Heather Bennett Florida Keys Real Estate Co. (KW)

  151 Cutthroat Dr, Summerland Key, FL 33042
• 

  

  /92

  Est $1,063,103

  Not Listed For Sale

  27436 Tobago Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft
  • Built 2020

  27436 Tobago Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 129 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

  $4,500 Per Month

  • 2 Beds
  • 1 Bath
  • 884 Sq Ft
  • House for Rent

  27346 Martinique Ln, Summerland Key, FL 33042

  Welcome to your private slice of paradise in the Florida Keys. This fully remodeled, exquisitely furnished 2-bedroom, 1-bathroom waterfront home is a true island escape. Where turquoise waters, swaying palms, and golden sunsets become your everyday view. Enjoy direct ocean access from your private dock, no bridges to slow you down. Lounge by the heated pool, dine under the stars, and feel the

  Alicia Rufino Island Living Realty, LLC

  27346 Martinique Ln, Summerland Key, FL 33042
• 

  

  /45

  $1,550,000

  Sold Jan 30, 2026

  28538 John Silver Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 1981

  Last Sold Summary

  • 3% Below List Price
  • $1,242/SF
  • 164 Days On Market

  Current Estimated Value $1,532,431

  Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.

  28538 John Silver Rd, Summerland Key, FL 33042
• 

  

  /35

  Est $992,127

  Not Listed For Sale

  17182 Starfish Ln W, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,265 Sq Ft
  • Built 1991

  17182 Starfish Ln W, Summerland Key, FL 33042

  Last Sold Summary

  • 6 Days On Market
• 

  

  /28

  $649,000

  Open Sat 11AM - 1PM

  • 2 Beds
  • 2 Baths
  • 1,080 Sq Ft

  19464 Seminole St, Summerland Key, FL 33042

  Move-In Ready Sugarloaf Key Retreat! Ideally located on beautiful Sugarloaf Key, this charming elevated 2-bedroom, 2-bath home offers the perfect blend of comfort, convenience, and island living. Just moments from a wonderful elementary and middle school, this bright and airy home welcomes you with an open floor plan filled with beautiful natural light, creating a warm and inviting atmosphere

  

  Miriam Novotny

  Compass Florida, LLC

  (645) 231-3946

  19464 Seminole St, Summerland Key, FL 33042
• 

  

  /45

  $630,000

  Sold Dec 08, 2025

  22970 Sharp Ln, Summerland Key, FL 33042

  • 1 Bed
  • 1 Bath
  • 576 Sq Ft
  • Built 1985

  Last Sold Summary

  • 10% Below List Price
  • $1,094/SF
  • 4 Days On Market

  Current Estimated Value $657,268

  Last Listing Agent Nick Boumerhi Meyer and Boumerhi Realty LLC

  22970 Sharp Ln, Summerland Key, FL 33042
• 

  

  /63

  Est $2,110,804

  Not Listed For Sale

  17057 Bonita Ln W, Sugarloaf Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 2,366 Sq Ft
  • Built 2015

  17057 Bonita Ln W, Sugarloaf Key, FL 33042

  Last Sold Summary

  • 190 Days On Market
• 

  

  /49

  $1,145,000

  $30K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,260 Sq Ft

  22737 Blackbeard Ln, Cudjoe Key, FL 33042

  Welcome home to your coastal oasis! This stunning brand-new elevated home features three bedrooms, two bathrooms, with an open concept living room and kitchen plus a covered 10x30 porch. Additional features include impact resistance windows and doors, metal roof, Azek decking, powder coated aluminum railings, custom concrete dock (8x20) with a permitted 12,000 Ibs. boat lift with 298 sq. ft. of

  

  Terry Garcia

  Keller Williams Key West Compass Realty

  (786) 321-8407

  22737 Blackbeard Ln, Cudjoe Key, FL 33042
• 

  

  /88

  $732,000

  Sold Apr 21, 2026

  40 Munson Ave, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1998

  Last Sold Summary

  • 2% Below List Price
  • $693/SF
  • 128 Days On Market

  Current Estimated Value $738,411

  Last Listing Agent Lindsay Ryan EXP Realty LLC

  40 Munson Ave, Summerland Key, FL 33042
• 

  

  /14

  Not Listed For Sale

  1639 Pine Channel Dr, Little Torch Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 6,725 Sq Ft
  • Built 1975

  1639 Pine Channel Dr, Little Torch Key, FL 33042

  Last Sold Summary

  • 7 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
• 

  

  /37

  $268,000

  Sold Apr 27, 2026

  701 Spanish Main Dr Unit 146, Cudjoe Key, FL 33042

  • Land
  • 2,178 Sq Ft
  • $5,360,000 per Acre

  Last Sold Summary

  • 3% Below List Price
  • 52 Days On Market

  Current Estimated Value $278,564

  Last Listing Agent Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 146, Cudjoe Key, FL 33042
• 

  

  /29

  Not Listed For Sale

  1693 Bayview Dr, Little Torch Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 917 Sq Ft
  • Built 1976

  1693 Bayview Dr, Little Torch Key, FL 33042

  Last Sold Summary

  • 60 Days On Market
• 

  /2

  $45,000

  $5K PRICE DROP

  • Land
  • 6,969 Sq Ft
  • $281,250 per Acre

  0 Bk 15 Lt 5 Unit 619550, Cudjoe Key, FL 33042

  Tier 3 lot in Cudjoe Key for ROGO Donation use. NO Building or RV allowed on this lot. worth 2 pts applying for Letter 2 additional lots available each for $50,000

  

  Terry Canto

  American Caribbean Real Estate, Christie's International Real Estate

  (844) 484-2446

  0 Bk 15 Lt 5 Unit 619550, Cudjoe Key, FL 33042
• 

  

  /60

  $930,000

  Sold Jan 23, 2026

  27405 Guadaloupe Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,288 Sq Ft
  • Built 2008

  Last Sold Summary

  • 2% Below List Price
  • $722/SF
  • 51 Days On Market

  Current Estimated Value $921,233

  Last Listing Agent Mark Gable Engel & Volkers Marathon

  27405 Guadaloupe Ln, Summerland Key, FL 33042
• 

  

  /29

  Not Listed For Sale

  701 Spanish Main Dr Unit 478, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 828 Sq Ft
  • Built 2001

  701 Spanish Main Dr Unit 478, Cudjoe Key, FL 33042

  Last Sold Summary

  • 14 Days On Market
• 

  

  /64

  $1,080,000

  • 3 Beds
  • 2 Baths
  • 1,356 Sq Ft

  22852 Buccaneer Ln, Summerland Key, FL 33042

  Experience the best of Keys living in this beautifully renovated waterfront home in sought-after Cudjoe Key--just minutes from local favorites like Square Grouper, 420 Lounge, and The Morning Joint. Boaters will appreciate the excellent access, complete with a concrete dock and 10,000 lb boat lift, making it easy to get on the water whenever you like. Privacy sets this property apart. The

  

  Austin Kimbler

  Expert Realty LLC (HQ)

  (645) 220-0519

  22852 Buccaneer Ln, Summerland Key, FL 33042
• 

  

  /73

  $2,925,000

  Sold Jun 10, 2025

  17018 Wahoo Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,472 Sq Ft
  • Built 1991

  Last Sold Summary

  • 25% Below List Price
  • $1,987/SF
  • 122 Days On Market

  Current Estimated Value $2,946,581

  Last Listing Agent Coby Taylor Expert Realty LLC (HQ)

  17018 Wahoo Ln, Summerland Key, FL 33042
• 

  

  /15

  Not Listed For Sale

  8 Calico Jack Circle Cir, Verifying, FL 33042

  8 Calico Jack Circle Cir, Verifying, FL 33042

  Last Sold Summary

  • 18 Days On Market
• 

  /2

  $45,000

  $5K PRICE DROP

  • Land
  • 6,969 Sq Ft
  • $281,250 per Acre

  0 Bk 15 Lt 13 Unit 619551, Cudjoe Key, FL 33042

  Tier 3 lot in Cudjoe Key for ROGO Donation use. NO Building or RV allowed on this lot. Will receive 2 points - Letter attach 2 additional lots available each for $50,000

  

  Terry Canto

  American Caribbean Real Estate, Christie's International Real Estate

  (844) 526-4158

  0 Bk 15 Lt 13 Unit 619551, Cudjoe Key, FL 33042

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