Homes in ZIP Code 33042

• 

  

  

  /29

  Est $928,834 Not Listed For Sale

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

  27359 Jamaica Ln, Summerland Key, FL 33042

  27359 Jamaica Ln, Summerland Key, FL 33042
• 

  

  

  /14

  $299,000

  • Land

  27398 Jamaica Ln, Ramrod Key, FL 33042

  Great Location vacant lot with seawall and boat ramp. Minutes to Open Water. Just waiting for a perfect home. This is a great option to purchase 231 W. Indies Open Water Home and have great boating with this lot.Please look at MLS616482

  Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

  27398 Jamaica Ln, Ramrod Key, FL 33042
• 

  

  

  /7

  $1,600,000 Sold Nov 21, 2025

  23038 Overseas Hwy, Cudjoe Key, FL 33042

  • Land
  • 1.37 Acres
  • $1,164,531 per Acre

  Last Sold Summary

  • 16% Below List Price
  • 141 Days On Market

  Last Listing Agent Deni Heintzelman KeyIsle Realty

  23038 Overseas Hwy, Cudjoe Key, FL 33042
• 

  

  /2

  Est $1,032,312 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,280 Sq Ft

  479 Blackbeard Rd, Summerland Key, FL 33042

  479 Blackbeard Rd, Summerland Key, FL 33042
• 

  

  

  /69

  $2,249,000 Pre-Foreclosure

  • 5 Beds
  • 3 Baths
  • 1,903 Sq Ft

  125 Colson Dr, Summerland Key, FL 33042

  THIS PROPERTY IS A ONE OF A KIND! A TRUE ''UNICORN!'' TRANSIENT LICENSE FOR NIGHTLY RENTALS BRINGING IN 230K-300K for 2026!! OPEN WATER VIEWS! ALMOST 2 ACRES TOTAL WITH 4 LOTS! Turnkey Vacation Rental with 4 bedrooms and 2 baths in Main House which is a charming and OLD FLORIDA KEYS STYLE PROPERTY! Privacy, lush vegetation, stunning Open water views from the balconies from almost every room!

  Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

  125 Colson Dr, Summerland Key, FL 33042
• 

  

  /29

  $1,245,000 Sold Jul 28, 2025

  17081 Starfish Ln W, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,542 Sq Ft
  • Built 1980

  Last Sold Summary

  • 9% Below List Price
  • $807/SF
  • 199 Days On Market

  Current Estimated Value $1,251,855

  Last Listing Agent Sean Farrer Coldwell Banker Schmitt Real E

  17081 Starfish Ln W, Summerland Key, FL 33042
• 

  

  /31

  Est $738,324 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,064 Sq Ft

  4245 Egret Ln, Summerland Key, FL 33042

  4245 Egret Ln, Summerland Key, FL 33042
• 

  

  /49

  $910,000

  • 2 Beds
  • 2 Baths
  • 1,008 Sq Ft

  813 Hawksbill Ln, Summerland Key, FL 33042

  Charming 2BR/2BA PLUS A LOFT, Keys home on Upper Sugarloaf, the perfect blend of comfort and waterfront living. Built on sturdy concrete pilings with Hardie board siding and a metal roof, this three-story retreat of island living. with GENERAC Generator. Inside, you'll find bright, cozy interiors with bamboo and ceramic tile floors and open living spaces for the relaxed Keys lifestyle. What truly

  Miguel Solis Douglas Elliman Florida, LLC - Sunset Drive

  813 Hawksbill Ln, Summerland Key, FL 33042
• 

  

  /47

  $895,000 Sold Dec 10, 2025

  22880 Blackbeard Ln, Summerland Key, FL 33042

  • 2 Beds
  • 1.5 Baths
  • 1,256 Sq Ft
  • Built 1993

  Last Sold Summary

  • 3% Below List Price
  • $713/SF
  • 34 Days On Market

  Last Listing Agent Pamela Stangler Expert Realty LLC

  22880 Blackbeard Ln, Summerland Key, FL 33042
• 

  

  /29

  Est $855,634 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,216 Sq Ft

  22774 Cudjoe Dr, Summerland Key, FL 33042

  22774 Cudjoe Dr, Summerland Key, FL 33042
• 

  

  /29

  $825,000 Under Contract

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

  17245 Jamaica Ln, Summerland Key, FL 33042

  Tucked along a quiet canal in Sugarloaf Shores, 17245 Jamaica Lane captures the essence of easy Keys living. This waterfront retreat offers direct access to open water and all things salt life--paddleboarding, kayaking, the iconic jumping bridge, and world-class cycling right out your door. Set on a generous lot, this elevated 3-bedroom, 2-bath home blends laid-back island charm with modern

  Team Kaufelt Truman & Co. (KW)

  17245 Jamaica Ln, Summerland Key, FL 33042
• 

  

  /38

  $775,000 Sold Sep 11, 2025

  22957 Drake Ln, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,008 Sq Ft
  • Built 1986

  Last Sold Summary

  • 4% Below List Price
  • $769/SF
  • 7 Days On Market

  Current Estimated Value $797,296

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  22957 Drake Ln, Cudjoe Key, FL 33042
• 

  

  /23

  Est $755,733 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft

  283 Pirates Rd, Summerland Key, FL 33042

  283 Pirates Rd, Summerland Key, FL 33042
• 

  

  /26

  $1,115,000

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

  27350 Barbados Ln, Ramrod Key, FL 33042

  Welcome to your slice of paradise in the Lower Florida Keys! This beautifully maintained 3-bedroom, 2-bath canal-front home offers everything you need for island living -- whether you're looking for a full-time residence, vacation getaway, or investment property. Nestled on a spacious 6,000 sq ft lot, this home boasts: - Direct Canal Access - Ideal for boaters! Navigate easily to open water. -

  Jonathan Minerick Homecoin.com

  27350 Barbados Ln, Ramrod Key, FL 33042
• 

  

  /24

  $430,000 Sold Nov 25, 2025

  701 Spanish Main Dr Unit 600, Cudjoe Key, FL 33042

  • Land

  Last Sold Summary

  • 13% Below List Price
  • 287 Days On Market

  Last Listing Agent Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 600, Cudjoe Key, FL 33042
• 

  

  /33

  Est $1,067,408 Not Listed For Sale

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

  131 W Indies Dr, Summerland Key, FL 33042

  131 W Indies Dr, Summerland Key, FL 33042
• 

  

  /45

  $2,995,000 Open House 2/22

  • 4 Beds
  • 3 Baths
  • 2,913 Sq Ft

  20920 5th Ave W, Summerland Key, FL 33042

  Florida Keys luxury island living at its finest. Welcome to your private slice of tropical island living in coveted Cudjoe Gardens--a true boater's dream set on an oversized double canal-front lot (approx. 15,200 sq. ft.) with an impressive close to 200 feet of concrete seawall. This beautifully designed CBS home offers 4 bedrooms, 3 baths, and nearly 3,000 sq. ft. of living space, thoughtfully

  Miriam Novotny Compass Florida, LLC

  20920 5th Ave W, Summerland Key, FL 33042
• 

  

  /43

  $1,170,000 Sold Aug 28, 2025

  1777 Pine Channel Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft
  • Built 2022

  Last Sold Summary

  • 10% Below List Price
  • $950/SF
  • 29 Days On Market

  Current Estimated Value $1,203,506

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  1777 Pine Channel Dr, Summerland Key, FL 33042
• 

  /2

  Est $721,871 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,648 Sq Ft

  19720 Date Palm Dr, Summerland Key, FL 33042

  19720 Date Palm Dr, Summerland Key, FL 33042
• 

  

  /3

  $64,750

  • Land

  0 Lot 21 Aloha Dr, Little Torch Key, FL 33042

  ROGO Lot. Letter on hand from Monroe County granting 2 points

  Jenna Stauffer Ocean Sotheby's International Realty

  0 Lot 21 Aloha Dr, Little Torch Key, FL 33042
• 

  

  /95

  $1,375,000 Sold Oct 30, 2025

  241 W Indies Dr, Ramrod Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 1,888 Sq Ft
  • Built 2021

  Last Sold Summary

  • 10% Below List Price
  • $728/SF
  • 226 Days On Market

  Current Estimated Value $1,428,940

  Last Listing Agent Jaime Caballero Key West Vacation Properties & Realty, LLC (KW)

  241 W Indies Dr, Ramrod Key, FL 33042
• 

  

  /4

  Est $831,354 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,108 Sq Ft

  27456 Martinique Ln, Summerland Key, FL 33042

  27456 Martinique Ln, Summerland Key, FL 33042
• 

  

  /33

  $268,500

  • 1 Bed
  • 1 Bath
  • 368 Sq Ft

  701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042

  Welcome to Unit 533 in the Venture Out community on Cudjoe Key, featuring a spacious addition that provides extra living space and flexibility. The addition includes a comfortable living area and a flex room currently used as additional sleeping space, suitable for guests, a home office, or hobby area.The home is clean and well cared for, offering a functional layout appropriate for full-time

  Jenifer Hirsch Bluescape Real Estate

  701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042
• 

  /2

  $180,000 Sold Feb 26, 2025

  0 Lan Guadaloupe Ln, Lower Keys, FL 33042

  • Land
  • 0.14 Acre
  • $1,285,714 per Acre

  Last Sold Summary

  • 92 Days On Market

  Last Listing Agent Chita Parus Realty Club, LLC

  0 Lan Guadaloupe Ln, Lower Keys, FL 33042
• 

  

  /45

  Est $1,903,425 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,752 Sq Ft

  19527 Indian Mound Dr, Summerland Key, FL 33042

  19527 Indian Mound Dr, Summerland Key, FL 33042
• 

  

  /53

  $2,375,000

  • 5 Beds
  • 4 Baths
  • 2,772 Sq Ft

  205 S Point Dr, Summerland Key, FL 33042

  Experience elevated waterfront living at this stunning South Point Sugarloaf Key retreat, where open-water serenity meets refined island design. This exceptional five-bedroom, four-bathroom residence is thoughtfully designed to host family and guests with ease, featuring a desirable split-floor plan and expansive living spaces framed by endless turquoise views.The primary suite is a private

  Dawn McComish Lokation Real Estate

  205 S Point Dr, Summerland Key, FL 33042
• 

  

  /55

  $1,800,000 Sold Jul 18, 2025

  22925 John Avery Ln, Summerland Key, FL 33042

  • 4 Beds
  • 4 Baths
  • 2,638 Sq Ft
  • Built 1993

  Last Sold Summary

  • 21% Below List Price
  • $682/SF
  • 164 Days On Market

  Current Estimated Value $1,751,695

  Last Listing Agent Jonathan Minerick Homecoin.com

  22925 John Avery Ln, Summerland Key, FL 33042
• 

  /2

  Est $1,078,554 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,408 Sq Ft

  1981 Sugarloaf Blvd, Summerland Key, FL 33042

  1981 Sugarloaf Blvd, Summerland Key, FL 33042
• 

  

  /94

  $3,500,000

  • 5 Beds
  • 4 Baths
  • 3,060 Sq Ft

  17249 Bonefish Ln E, Sugarloaf Key, FL 33042

  Experience the ultimate island lifestyle in this breathtaking waterfront residence located in the prestigious Sugarloaf Shores subdivision. Situated on a massive 25,482 sq. ft. lot, this property offers rare privacy with plenty of room to breathe.Built with solid CBS construction, this 5-bedroom, 4-bath home is designed to capture the beauty of its surroundings. The open living space and

  Daniel Urban Expert Realty LLC (HQ)

  17249 Bonefish Ln E, Sugarloaf Key, FL 33042
• 

  

  /30

  $775,000 Sold Sep 30, 2025

  24827 Park Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,274 Sq Ft
  • Built 2018

  Last Sold Summary

  • 14% Below List Price
  • $608/SF
  • 175 Days On Market

  Current Estimated Value $809,271

  Last Listing Agent Juan Benitez Benitez Keller Williams Key West Compass Realty

  24827 Park Dr, Summerland Key, FL 33042
• 

  

  /20

  Est $771,305 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 816 Sq Ft

  4244 Dorn Rd, Summerland Key, FL 33042

  4244 Dorn Rd, Summerland Key, FL 33042
• 

  

  /7

  $4,375,000 Open Sun 10AM - 1PM

  • 5 Beds
  • 5.5 Baths
  • 3,119 Sq Ft

  231 E Shore Dr Unit 4, Summerland Key, FL 33042

  Introducing Seven Palms Cove, a one-of-a-kind new construction community redefining luxury island living in the Florida Keys. With only seven exclusive oceanfront residences starting at $4M, this private, gated enclave offers an extraordinary opportunity to own a slice of paradise just minutes from Key West.Each home spans over 4,000 sq. ft. with 5 bedrooms, 5.5 bathrooms, and open-concept

  Stephanie Muzzillo Serhant Florida LLC - Delray Beach Office

  231 E Shore Dr Unit 4, Summerland Key, FL 33042
• 

  

  /50

  $550,000 Sold Jul 14, 2025

  701 Spanish Main Dr Unit 631, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft
  • Built 2021

  Last Sold Summary

  • 18% Below List Price
  • $637/SF
  • 245 Days On Market

  Last Listing Agent Joe Sappington Waterfront Keys Realty Inc.

  701 Spanish Main Dr Unit 631, Cudjoe Key, FL 33042
• 

  

  /34

  Est $739,866 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft

  4040 Dorn Rd, Summerland Key, FL 33042

  4040 Dorn Rd, Summerland Key, FL 33042
• 

  

  /62

  $1,015,000

  • 3 Beds
  • 2 Baths
  • 1,377 Sq Ft

  231 W Indies Dr, Summerland Key, FL 33042

  Welcome to your open-water paradise! This 3-bedroom, 2-bath home is all about embracing the Florida lifestyle. Wake up to breathtaking open-water sunrises while you sip coffee on your private balcony, then spend your afternoons lounging by the sparkling pool. The main level offers two comfortable bedrooms and a full bath -- perfect for family or guests -- while the entire second floor is your

  Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

  231 W Indies Dr, Summerland Key, FL 33042
• 

  

  /42

  $895,000 Sold May 21, 2025

  17214 La Brisa Ln, Summerland Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 1,344 Sq Ft
  • Built 1992

  Last Sold Summary

  • 10% Below List Price
  • $666/SF
  • 50 Days On Market

  Current Estimated Value $950,284

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

  17214 La Brisa Ln, Summerland Key, FL 33042
• 

  /2

  Est $1,531,904 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,160 Sq Ft

  390 Les Rohde Dr, Summerland Key, FL 33042

  390 Les Rohde Dr, Summerland Key, FL 33042
• 

  

  /64

  $1,900,000

  • 3 Beds
  • 2 Baths
  • 1,841 Sq Ft

  3127 Stewart Rd, Summerland Key, FL 33042

  Gorgeous Open Water home that has been beautifully remodeled on 1.65 Acres of private land with handicap accessibilty! Complete remodel done, including the concrete pilings completed by a licensed contractor. Huge downstairs enclosure with a 2-car garage, this is an incredible opportunity to own a piece of nature in the Florida Keys! Privacy abounds on 1.65 acres of beautifully preserved, natural

  Pamela Stangler Expert Realty LLC

  3127 Stewart Rd, Summerland Key, FL 33042
• 

  

  /43

  $870,000 Sold Oct 10, 2025

  22818 Privateer Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,452 Sq Ft
  • Built 1997

  Last Sold Summary

  • $599/SF
  • 1 Day On Market

  Current Estimated Value $867,593

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

  22818 Privateer Dr, Summerland Key, FL 33042
• 

  

  /47

  Est $2,696,020 Not Listed For Sale

  • 2 Beds
  • 3 Baths
  • 1,958 Sq Ft

  27440 W Indies Dr, Summerland Key, FL 33042

  27440 W Indies Dr, Summerland Key, FL 33042

Showing Results 481 - 520, Page 13 of 18