Homes in ZIP Code 33042

• 

  

  

  /31

  $749,500

  • 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
• 

  

  

  /70

  $12,500 per month

  • 4 Beds
  • 4 Baths
  • 2,952 Sq Ft
  • Property for Rent

  21640 Overseas Hwy, Summerland Key, FL 33042

  Waterfront Paradise in Cudjoe KeyWelcome to 21640 Overseas Highway, Cudjoe Key, FL 33042--a spectacular 4-bedroom, 4-bathroom waterfront sanctuary offering panoramic open-water views and the ultimate Florida Keys lifestyle.Inside, the home features a beautifully updated kitchen with modern finishes, spacious living areas designed for comfort and entertaining, and a huge master suite overlooking

  

  Dan Serban

  Key West Luxury Real Estate Inc (KW)

  (786) 442-3255

  21640 Overseas Hwy, Summerland 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 $849,106

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

  27417 Cayman Ln, Summerland Key, FL 33042
• 

  

  

  /18

  Est $746,279 Not Listed For Sale

  27438 Haiti Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft
  • Built 1987

  27438 Haiti Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 1% Above List Price
  • $904/SF
  • 146 Days On Market

  Last Sold Price $738,000

  Last Listing Agent Caroline Bauer Key West Sales, LLC
• 

  

  

  /71

  $1,395,000

  • 3 Beds
  • 3 Baths
  • 1,700 Sq Ft

  16941 Driftwood Ln, Summerland Key, FL 33042

  There are homes that check boxes, and then there are homes that speak to you the moment you step inside. This custom, meticulously crafted 3BR/3BA, 1,700 sq ft CBS masterpiece in the heart of Sugarloaf Shores is the latter, where thoughtful design, quiet elegance, and a touch of whimsy blend into a living experience that feels both luxurious and deeply personal.Set just 19 minutes from Key West,

  

  Coby Taylor

  Taylor & Assoc. RE, Inc.

  (855) 606-6133

  16941 Driftwood Ln, Summerland Key, FL 33042
• 

  

  /12

  $2,500 per month

  Coco Palms

  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.

  21585 Overseas Hwy, Cudjoe 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 $941,667

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

  76 W Shore Dr, Summerland Key, FL 33042
• 

  

  /63

  Est $1,923,826 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

  • 3% Below List Price
  • $835/SF
  • 190 Days On Market

  Last Sold Price $1,975,000

  Last Listing Agent Lisa Swanson The Agency Florida Keys
• 

  

  /49

  $945,000

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  683 Blackbeard Rd, Summerland Key, FL 33042

  Located near a canal 'T', this oceanside property offers easy docking for larger boats and sailboats in the 50 ft. wide, flow-through canal, putting the Atlantic and back-country within easy reach. The rooftop deck is a wonderful vantage point for panoramic neighborhood and water views. Nestled in mature vegetation, the one-owner, custom-built, board and batten cedar home has been well-maintained

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  (833) 982-0551

  683 Blackbeard Rd, Summerland Key, FL 33042
• 

  

  /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
• 

  /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 $1,027,186

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

  22521 Jolly Roger Dr, Cudjoe Key, FL 33042
• 

  

  /9

  Not Listed For Sale

  Lot 8 Overseas Hwy, Summerland Key, FL 33042

  Lot 8 Overseas Hwy, Summerland Key, FL 33042

  Last Sold Summary

  • $24/SF

  Last Sold Price $300,000

  Last Listing Agent Jana Alarid Coldwell Banker Realty
• 

  

  /71

  $1,349,000

  • 2 Beds
  • 2 Baths
  • 1,344 Sq Ft

  403 Indies Rd, Ramrod Key, FL 33042

  Private Ramrod Key Sanctuary with Sunset Views & Exceptional Boating Access.A rare find, spanning over a 15,000 sq ft, fully fenced lot, offering remarkable privacy, natural beauty, and spectacular sunrise and sunset views. The main home features expansive impact glass door systems in the front and rear, filling the living space with natural light and framing canal views, distant views of the

  

  Sandra Tuttle

  Island Welcome Real Estate

  (786) 952-7871

  403 Indies Rd, Ramrod Key, FL 33042
• 

  

  /20

  $5,357 - $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
• 

  

  /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 $1,676,709

  Last Listing Agent Lisa Swanson The Agency Florida Keys

  17159 Amberjack Ln, 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

  • $37/SF
  • 7 Days On Market

  Last Sold Price $250,000

  Last Listing Agent Rose Dell Keller Williams Key West Compass Realty
• 

  

  /49

  $1,150,000

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

  110 Doubloon Ln, Summerland Key, FL 33042

  Welcome to island life--this charming 2-bedroom, 2-bath waterfront cottage captures everything we love about the Florida Keys. Tucked on a desirable corner lot with canals on two sides, the property offers exceptional privacy, sea breezes, and inviting views from multiple vantage points. Inside, the home is bright, fresh, and thoughtfully updated, featuring a crisp white kitchen with quartz

  

  Sandra Tuttle

  Island Welcome Real Estate

  (786) 957-4255

  110 Doubloon Ln, Summerland Key, FL 33042
• 

  

  /19

  $4,900 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 $1,511,933

  Last Listing Agent Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

  28538 John Silver Rd, 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

  • $966/SF
  • 14 Days On Market

  Last Sold Price $800,000

  Last Listing Agent Susan Rich Select Properties of NWFL
• 

  

  /92

  $3,799,000 Pending

  • 3 Beds
  • 3 Baths
  • 1,728 Sq Ft

  493 Coral Ave, Summerland Key, FL 33042

  There are homes in the Florida Keys... and then there are legacy properties. Conceived and built by internationally recognized Keys architect Glenn Gray as his personal residence, 493 Coral Avenue is a rare architectural offering positioned on a premier point lot with open Gulf frontage and protected canal dockage. With water on two sides and panoramic sunrise-to-sunset views, the setting is

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (645) 300-3164

  493 Coral Ave, Summerland Key, FL 33042
• 

  

  /13

  $3,000 per month

  • 3 Beds
  • 2 Baths
  • 1,109 Sq Ft
  • House for Rent

  26945 Shannahan Rd, Summerland Key, FL 33042

  Property Id: 24239533 Bd/2 Bth Concrete block home. Central A/C with heat. Granite counter tops in kitchen. Fridge, Gas Stove, dishwasher and central ac. Stackable washer/dryer. Fenced back yard. Concrete patio in front or parking area. In Ramrod Key. Non waterfront. No house on either side. Must have good credit and references and income will be verified. Utilities NOT included. Rent

  26945 Shannahan Rd, 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 $662,671

  Last Listing Agent Nick Boumerhi Meyer and Boumerhi Realty LLC

  22970 Sharp 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

  Last Sold Price $165,000

  Last Listing Agent Beata Sharpe COLDWELL BANKER VANGUARD REALTY
• 

  

  /48

  $1,399,000

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft

  823 Indies Rd, Ramrod Key, FL 33042

  Fabulous sunset views over the salt ponds at this concrete 3 Bedroom 2 Bath home in Breezeswept Beach Estates. Located towards the end of a very quiet street this home offers a lot of privacy with beautiful views of the bird estuary in front and long views of the canal in the back. Boaters will appreciate the immediate ocean access with no bridges and easy turn around from the 60' step-down dock

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (305) 614-6847

  823 Indies Rd, Ramrod Key, FL 33042
• 

  

  /16

  $5,357 per month

  • 2 Beds
  • 2 Baths
  • 1,079 Sq Ft
  • House for Rent

  53 Barry Ave, Summerland Key, FL 33042

  This is a 2 story furnished or unfurnished single family house with a private pool, fenced in yard, screened patio, 2 bedrooms, 2 bathrooms with showers, stainless steel appliances, hurricane windows, washer and dryer, tile and wood floors. You are also able to use the amenities at our property next door such as 24 hour community gym and sauna. marina with boat ramp, outdoor games, bbq, kayaks

  Joseph Danieli AKT Realty LLC

  53 Barry Ave, Summerland Key, FL 33042
• 

  

  /35

  $1,499,900 Sold May 27, 2025

  1082 Bay Dr, Summerland Key, FL 33042

  • 4 Beds
  • 2.5 Baths
  • 1,440 Sq Ft
  • Built 1980

  Last Sold Summary

  • 25% Below List Price
  • $1,042/SF
  • 602 Days On Market

  Current Estimated Value $1,747,013

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  1082 Bay Dr, Summerland Key, FL 33042
• 

  

  /40

  Not Listed For Sale

  701 Spanish Main Dr Unit 366, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft
  • Built 1996

  701 Spanish Main Dr Unit 366, Cudjoe Key, FL 33042

  Last Sold Summary

  • $674/SF
  • 22 Days On Market

  Last Sold Price $550,000

  Last Listing Agent Ian Calderwood Bluescape Real Estate
• 

  

  /62

  $5,200,000

  • 4 Beds
  • 4 Baths
  • 2,660 Sq Ft

  17013 Coral Dr, Summerland 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

  (786) 882-3659

  17013 Coral Dr, Summerland Key, FL 33042
• 

  

  /13

  $5,538 per month

  • 2 Beds
  • 2.5 Baths
  • 1,080 Sq Ft
  • Townhouse for Rent

  28513 Channel View Dr, Little Torch Key, FL 33042

  This is a waterfront 3 story, 2 bedroom, 2.5 bathroom unfurnished or furnished townhome for rent on a year lease. It is located in the community of Little Torch Cottages in Little Torch Key between Marathon and Key West. It has stainless steel appliances, full size front load stackable washer and dryer, tile floors, hurricane windows and doors, 3 balconies, 2 heated community pools, 24 hour

  Joseph Danieli AKT Realty LLC

  28513 Channel View Dr, Little Torch 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 $926,331

  Last Listing Agent Mark Gable Engel & Volkers Marathon

  27405 Guadaloupe Ln, Summerland Key, FL 33042
• 

  

  /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

  • $750/SF
  • 9 Days On Market

  Last Sold Price $540,000

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

  

  /58

  $3,750,000

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

  755 Sawyer Dr, Summerland 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 for.

  

  Terrance Sullivan

  Ocean Sotheby's International Realty

  (786) 204-2360

  755 Sawyer Dr, Summerland Key, FL 33042
• 

  

  /14

  $3,900 per month

  • 2 Beds
  • 2.5 Baths
  • 1,080 Sq Ft
  • Townhouse for Rent

  28534 Channel View Dr, Little Torch Key, FL 33042

  Current resident moving out on 4/30/26.This is a 3 story 2 bedroom 2.5 bathroom unfurnished townhome for rent on a year lease.It is located in the community of Little Torch Cottages in Little Torch Key between Marathon and Key West. It has stainless steel appliances, stackable washer and dryer, hurricane windows and doors, two balconies, 2 heated and chilled community pools, gym, sauna, marina

  Joseph Danieli AKT Realty LLC

  28534 Channel View Dr, Little Torch 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 $2,936,647

  Last Listing Agent Coby Taylor Taylor & Assoc. RE, Inc.

  17018 Wahoo Ln, Summerland Key, FL 33042
• 

  

  /20

  Not Listed For Sale

  28587 Peg Leg Rd, Little Torch Key, FL 33042

  28587 Peg Leg Rd, Little Torch Key, FL 33042

  Last Sold Summary

  • 80 Days On Market

  Last Sold Price $190,000

  Last Listing Agent Tylon Fraley Southeast Realty Equities, Inc
• 

  

  /43

  $1,499,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft

  17152 Marlin Dr, Summerland Key, FL 33042

  Nestled on a very quiet street in the exclusive community Sugarloaf Shores, this beautifully remodeled CBS Pool Home offers the perfect blend of privacy, entertainment and island charm. Situated on a massive 12,700 sq. ft. lot, this property is a lush sanctuary for gardeners and boaters alike. The backyard is a true private resort, designed for the ultimate outdoor lifestyle featuring a heated

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (786) 692-4942

  17152 Marlin Dr, Summerland Key, FL 33042
• 

  

  /9

  $12,500 per month

  • 4 Beds
  • 3 Baths
  • 2,855 Sq Ft
  • House for Rent

  28502 Channel View Dr, Little Torch Key, FL 33042

  This is a 3 story furnished 4 bedroom 3 bathroom home with a water view of the gulf in the Little Torch Cottages community of townhomes. There are 2 heated and chilled community pools, a gym, a sauna, a marina with boat ramp, bbq, exterior yard games and boat slip available for an extra charge. Kayaks and paddle boards are available for community usage.

  Joseph Danieli AKT Realty LLC

  28502 Channel View Dr, Little Torch Key, FL 33042
• 

  

  /8

  $906,300 Sold Apr 30, 2025

  0000 Dorn Rd, Big Torch Key, FL 33042

  • Land
  • 35.5 Acres
  • $25,530 per Acre

  Last Sold Summary

  • 43% Below List Price
  • 103 Days On Market

  Last Listing Agent Lindsay Ryan EXP Realty LLC

  0000 Dorn Rd, Big Torch Key, FL 33042
• 

  

  /50

  Est $862,290 Not Listed For Sale

  489 Pirates Rd, Little Torch Key, FL 33042

  • 4 Beds
  • 4 Baths
  • 1,638 Sq Ft
  • Built 1984

  489 Pirates Rd, Little Torch Key, FL 33042

  Last Sold Summary

  • 1% Below List Price
  • $534/SF
  • 38 Days On Market

  Last Sold Price $875,000

  Last Listing Agent Jessica Celli Berkshire Hathaway HomeServices Knight & Gardner Realty

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