6,959

Homes in ZIP Code 33042

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  • /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 $788,607

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    22957 Drake Ln, Cudjoe Key, FL 33042
    • /2

      Est $757,324 Not Listed For Sale

      19720 Date Palm Dr, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,648 Sq Ft
      • Built 1958
      19720 Date Palm Dr, Summerland Key, FL 33042

      Last Sold Summary

      • 11% Below List Price
      • $413/SF

      Last Sold Price $680,000

      Last Listing Agent Linda Merkey Century 21 Circle - Key West

  • /38

    $1,049,000

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

    288 Spanish Main Dr, Summerland Key, FL 33042

    Beautifully renovated canalfront home on Cudjoe Key offering the perfect blend of modern upgrades and classic Florida Keys charm. This 3-bedroom, 2-bath stilted home has been completely updated for serene, worry-free living.Inside, you'll find a beautiful kitchen with stainless steel appliances and quartz countertops, along with a comfortable living area. Step outside to enjoy spacious covered

    Richard Haskins Buy The Keys

    288 Spanish Main Dr, Summerland 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

    Current Estimated Value $421,591

    Last Listing Agent Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 600, Cudjoe Key, FL 33042
    • /64

      Est $1,121,819 Not Listed For Sale

      184 Cutthroat Dr, Summerland Key, FL 33042

      • 4 Beds
      • 2 Baths
      • 2,320 Sq Ft
      • Built 1963
      184 Cutthroat Dr, Summerland Key, FL 33042

      Last Sold Summary

      • 19% Above List Price
      • $405/SF
      • 151 Days On Market

      Last Sold Price $940,000

      Last Listing Agent Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

  • /71

    $1,094,900

    • 3 Beds
    • 2 Baths
    • 1,272 Sq Ft

    19881 Date Palm Dr, Summerland Key, FL 33042

    Escape to your own private paradise at 19881 Date Palm Drive in Sugarloaf Key! This beautifully updated single-family home is tucked away in a quiet, secluded location and offers 100 feet of pristine canal frontage with a cut-in boat slip--perfect for boating enthusiasts with no neighbors across the canal!Step inside to find rich Brazilian hardwood floors, custom wood cabinetry, and sleek

    Jimmy Lane Island Life Realty Experts

    19881 Date Palm Dr, Summerland Key, FL 33042
  • /61

    $2,000,000 Sold Mar 18, 2026

    743 Pattison Dr, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,674 Sq Ft
    • Built 1997

    Last Sold Summary

    • 11% Below List Price
    • $1,195/SF
    • 135 Days On Market

    Current Estimated Value $2,118,685

    Last Listing Agent Sandra Tuttle Island Welcome Real Estate

    743 Pattison Dr, Summerland Key, FL 33042
    • /4

      Est $830,668 Not Listed For Sale

      27456 Martinique Ln, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 1,108 Sq Ft
      • Built 1976
      27456 Martinique Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 21% Below List Price
      • $948/SF
      • 0 Days On Market

      Last Sold Price $1,050,000

      Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

  • /41

    $2,395,000 Pending

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

    1176 Thatch Ln, Summerland Key, FL 33042

    Unobstructed Ocean views, your own Private Oasis! On a canal with easy access to both the Ocean and Back Country. Whether you're seeking a full time residence, vacation getaway, or income-producing investment, this waterfront gem checks every box! Huge 24,829 Sqft LOT with plenty of room to add on. The home has consistent vacation rentals booked 4+ months out of the year, every year!! (income

    Jonathan Minerick Homecoin.com

    1176 Thatch Ln, 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 $1,174,506

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    1777 Pine Channel Dr, Summerland Key, FL 33042
    • /45

      Est $1,960,371 Not Listed For Sale

      19527 Indian Mound Dr, Summerland Key, FL 33042

      • 3 Beds
      • 3 Baths
      • 1,752 Sq Ft
      • Built 1996
      19527 Indian Mound Dr, Summerland Key, FL 33042

      Last Sold Summary

      • 2% Above List Price
      • $1,142/SF
      • 96 Days On Market

      Last Sold Price $2,000,000

      Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  • /42

    $2,089,000

    • 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. 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 vacation rental retreat.

    Michelle Blades Realty Executives Florida Keys Old Town

    94 Sacarma Dr, Cudjoe 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 $1,406,602

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

    241 W Indies Dr, Ramrod Key, FL 33042
    • /2

      Est $1,084,016 Not Listed For Sale

      1981 Sugarloaf Blvd, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 1,408 Sq Ft
      • Built 1988
      1981 Sugarloaf Blvd, Summerland Key, FL 33042

      Last Sold Summary

      • 9% Below List Price
      • $710/SF

      Last Sold Price $999,000

      Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  • /26

    $899,000

    • Land
    • 5 Acres
    • $179,800 per Acre

    2231 Middle Torch Rd, Summerland Key, FL 33042

    Opportunities like this are few and far between. This extraordinary offering includes two adjoining 2.5-acre parcels, totaling 5 acres of land -- Truly a rare find in the Florida Keys. Each lot measures 110 x 990 feet, offering an abundance of space, privacy, and potential. The property currently features two dwellings -- a single-family residence and a manufactured dwelling on the other -- each

    Stephany Duvall Engel & Volkers Marathon

    2231 Middle Torch Rd, Summerland Key, FL 33042
  • /50

    $1,550,000 Sold Feb 23, 2026

    56 Colson Dr, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,645 Sq Ft
    • Built 1995

    Last Sold Summary

    • 3% Below List Price
    • $942/SF
    • 12 Days On Market

    Current Estimated Value $1,555,236

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    56 Colson Dr, Summerland Key, FL 33042
    • /20

      Est $781,483 Not Listed For Sale

      4244 Dorn Rd, Summerland Key, FL 33042

      • 2 Beds
      • 1 Bath
      • 816 Sq Ft
      • Built 1984
      4244 Dorn Rd, Summerland Key, FL 33042

      Last Sold Summary

      • $953/SF
      • 368 Days On Market

      Last Sold Price $778,000

      Last Listing Agent Tommy Gomez Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

  • /7

    $4,375,000 New Construction

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

    231 E Shore Dr Unit 6, 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 Marinucci Serhant Florida LLC - Delray Beach Office

    231 E Shore Dr Unit 6, 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 $1,775,129

    Last Listing Agent Jonathan Minerick Homecoin.com

    22925 John Avery Ln, Summerland Key, FL 33042
    • /34

      Est $744,314 Not Listed For Sale

      4040 Dorn Rd, Summerland Key, FL 33042

      • 2 Beds
      • 1 Bath
      • 768 Sq Ft
      • Built 1991
      4040 Dorn Rd, Summerland Key, FL 33042

      Last Sold Summary

      • 2% Below List Price
      • $988/SF
      • 193 Days On Market

      Last Sold Price $759,000

      Last Listing Agent Deni Heintzelman KeyIsle Realty

  • /18

    $3,999,999

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

    17229 Oleander Ln, Summerland Key, FL 33042

    Modern luxury seamlessly blends with relaxed tropical living in this oversized, brand-new construction home located on Sugarloaf Key. This elevated three-story residence features 5 bedrooms and 5 bathrooms all en suite, offering approximately 3,700 square feet of thoughtfully designed living space on a 10,000-square-foot lot. Designed with both lifestyle and functionality in mind, the home

    Justyn Ewald Expert Realty LLC (HQ)

    17229 Oleander Ln, Summerland 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 $774,334

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

    24827 Park Dr, Summerland Key, FL 33042
    • /47

      Est $2,637,906 Not Listed For Sale

      27440 W Indies Dr, Summerland Key, FL 33042

      • 2 Beds
      • 3 Baths
      • 1,958 Sq Ft
      • Built 1982
      27440 W Indies Dr, Summerland Key, FL 33042

      Last Sold Summary

      • 14% Above List Price
      • $1,558/SF
      • 2 Days On Market

      Last Sold Price $3,050,000

      Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  • /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
  • /17

    $320,000 Sold Feb 20, 2026

    27977 Coral Shores Rd, Little Torch Key, FL 33042

    • 2 Beds
    • 1 Bath
    • 684 Sq Ft
    • Built 1980

    Last Sold Summary

    • 20% Below List Price
    • $468/SF
    • 54 Days On Market

    Last Listing Agent Dasha Ray Conch Realty LLC (KW)

    27977 Coral Shores Rd, Little Torch Key, FL 33042
    • /46

      Est $2,636,194 Not Listed For Sale

      961 W Indies Dr, Summerland Key, FL 33042

      • 4 Beds
      • 3 Baths
      • 2,006 Sq Ft
      • Built 1998
      961 W Indies Dr, Summerland Key, FL 33042

      Last Sold Summary

      • 12% Above List Price
      • $1,495/SF
      • 37 Days On Market

      Last Sold Price $2,999,000

      Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  • /39

    $899,000

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft

    701 Spanish Main Dr Unit 221, Cudjoe Key, FL 33042

    Enjoy open water views and instant boating access from this transiently licensed, turn-key retreat in Venture Out Resort, just 20 minutes from Key West. Built in 2021, this modern 2-bedroom, 2-bath oceanfront home combines sleek design with comfort and quality craftsmanship. Step inside to discover 9ft ceilings, leather-finish granite countertops, and high-end finishes throughout. The home comes

    The Spottswood Team Truman & Co. (KW)

    701 Spanish Main Dr Unit 221, Cudjoe 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
    • /28

      Est $810,277 Not Listed For Sale

      27378 Haiti Ln, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 925 Sq Ft
      • Built 1963
      27378 Haiti Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 1% Above List Price
      • $868/SF
      • 34 Days On Market

      Last Sold Price $803,000

      Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  • /69

    $2,195,000

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

    125 Colson Dr, Summerland Key, FL 33042

    TRANSIENT LICENSE FOR NIGHTLY RENTALS BRINGING IN 250k-300K for 2026!! OPEN WATER VIEWS! ALMOST 2 ACRES TOTAL WITH 4 LOTS! THIS PROPERTY IS A ONE OF A KIND! A TRUE ''UNICORN!'' 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
  • /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 $932,334

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    17214 La Brisa Ln, Summerland Key, FL 33042
    • /41

      Est $850,275 Not Listed For Sale

      27468 Haiti Ln, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,380 Sq Ft
      • Built 1979
      27468 Haiti Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 2% Above List Price
      • $601/SF
      • 6 Days On Market

      Last Sold Price $830,000

      Last Listing Agent Emily Lombard Ocean Sotheby's International Realty

  • /26

    $1,080,000

    • 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
  • /17

    $850,000 Sold Mar 30, 2026

    17171 Seagrape Ln, Summerland Key, FL 33042

    • 3 Beds
    • 3 Baths
    • 1,400 Sq Ft
    • Built 1982

    Last Sold Summary

    • 22% Below List Price
    • $607/SF
    • 132 Days On Market

    Current Estimated Value $1,003,456

    Last Listing Agent Marie Howe Century 21 Circle - Key West

    17171 Seagrape Ln, Summerland Key, FL 33042
    • /2

      Est $763,237 Not Listed For Sale

      433 Indies Rd, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 864 Sq Ft
      • Built 1991
      433 Indies Rd, Summerland Key, FL 33042

      Last Sold Summary

      • 2% Below List Price
      • $868/SF

      Last Sold Price $750,000

      Last Listing Agent Rick Servais Coldwell Banker Schmitt Real Estate Co.

  • /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
  • /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 $863,179

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

    22818 Privateer Dr, Summerland Key, FL 33042
    • /45

      Est $1,115,203 Not Listed For Sale

      23058 Sailfish Ln, Summerland Key, FL 33042

      • 3 Beds
      • 3 Baths
      • 1,280 Sq Ft
      • Built 1980
      23058 Sailfish Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 5% Below List Price
      • $918/SF
      • 145 Days On Market

      Last Sold Price $1,175,000

      Last Listing Agent Jan Fritz Coldwell Banker Schmitt RE Co.

  • /2

    $299,000

    • Land

    28168 Julia Ave, Little Torch Key, FL 33042

    ROGO EXEMPT LOT! Build Now, No Waiting, Water Meter On Site, 6000 SF, Boat Ramp Within Walking Distance, Live The Dream. Single family home next door going on the market soon, buy both!

    Doug Addeo Regional Trust Corporation

    28168 Julia Ave, Little Torch Key, FL 33042
  • /56

    $2,599,000 Sold Jun 18, 2025

    28595 Jolly Roger Dr, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 1,153 Sq Ft
    • Built 1975

    Last Sold Summary

    • $2,254/SF
    • 11 Days On Market

    Current Estimated Value $2,612,934

    Last Listing Agent Jan Fritz Coldwell Banker Schmitt RE Co.

    28595 Jolly Roger Dr, Summerland Key, FL 33042

Showing Results 481 - 520, Page 13 of 18

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