6,951

Homes in ZIP Code 33042

Section Image
  • /41

    $1,099,990

    New Construction $69K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,320 Sq Ft

    325 Pirates Rd, Summerland Key, FL 33042

    *POOL PLANS IN HAND FOR 12X22 POOL, WITH POOL QUOTE* Escape to paradise with this incredible waterfront property located on a deep boating canal in the heart of the Lower Florida Keys. Perfectly suited for boating enthusiasts and water lovers, this home offers dockage and a boat lift, and direct, easy access to the open waters of the Atlantic Ocean and Gulf of Mexico, making it a dream come true

    Nick Boumerhi Meyer and Boumerhi Realty LLC

    325 Pirates Rd, Summerland Key, FL 33042
  • /53

    $2,725,000

    Sold Mar 11, 2026

    1147 Flagship Dr, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 2,058 Sq Ft
    • Built 1997

    Last Sold Summary

    • 6% Below List Price
    • $1,324/SF
    • 103 Days On Market

    Current Estimated Value $2,655,734

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    1147 Flagship Dr, Summerland Key, FL 33042
    • /28

      Est $1,839,778

      Not Listed For Sale

      27385 St Lucie Ln, Ramrod Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 1,988 Sq Ft
      • Built 1987
      27385 St Lucie Ln, Ramrod Key, FL 33042

      Last Sold Summary

      • 0 Days On Market

  • /7

    $895,000

    Under Contract
    • 4 Beds
    • 2 Baths
    • 1,800 Sq Ft

    22817 Privateer Dr, Summerland Key, FL 33042

    Experience elevated island living in this beautifully renovated concrete home located in the heart of Cudjoe Key. Situated on desirable Privateer Drive, this stunning 4-bedroom, 1,800 square-foot residence perfectly combines modern upgrades, durable construction, and tropical outdoor luxury.Thoughtfully redesigned with stylish finishes and an open-concept layout, the home offers spacious

    Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

    22817 Privateer Dr, Summerland Key, FL 33042
  • /2

    $185,000

    Sold Mar 20, 2026

    1223 Rogers Ln, Cudjoe Key, FL 33042

    • Land
    • 6,969 Sq Ft
    • $1,156,250 per Acre

    Last Sold Summary

    • 0 Days On Market

    Current Estimated Value $287,661

    Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.

    1223 Rogers Ln, Cudjoe Key, FL 33042
    • /2

      Est $857,184

      Not Listed For Sale

      53 Gold Boullion Rd, Cudjoe Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,404 Sq Ft
      • Built 2016
      53 Gold Boullion Rd, Cudjoe Key, FL 33042

      Last Sold Summary

  • /68

    $879,000

    • 2 Beds
    • 2 Baths
    • 816 Sq Ft

    701 Spanish Main Dr Unit 265, Cudjoe Key, FL 33042

    This Truly Spectacular Oceanfront Property offers the ultimate waterfront lifestyle and is a one of a kind, featuring an impressive 98' seawall. Designed to capture the best of coastal living, the property combines 72' of concrete seawall along a protected canal with 26' of direct Atlantic Ocean Frontage, delivering both tranquility and open-ocean beauty. A waterfront lovers dream, the canal side

    Kim Babenzien Expert Realty LLC (HQ)

    701 Spanish Main Dr Unit 265, Cudjoe Key, FL 33042
  • /44

    $853,000

    Sold Aug 12, 2025

    873 Indies Rd, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,081 Sq Ft
    • Built 2002

    Last Sold Summary

    • 10% Below List Price
    • $789/SF
    • 123 Days On Market

    Current Estimated Value $877,740

    Last Listing Agent Donna Halstead Coldwell Banker Schmitt RE Co.

    873 Indies Rd, Summerland Key, FL 33042
    • /23

      Est $748,659

      Not Listed For Sale

      27225 Mariposa Rd, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,364 Sq Ft
      • Built 2017
      27225 Mariposa Rd, Summerland Key, FL 33042

      Last Sold Summary

      • 382 Days On Market

  • /35

    $530,000

    $10K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,184 Sq Ft

    27967 Coral Shores Rd, Little Torch Key, FL 33042

    Canal-front living at its finest! This beautifully remodeled 2-bedroom, 2-bath home is truly a must-see. Step inside to discover a bright and inviting interior featuring new flooring, an updated kitchen, and stylishly renovated bathrooms. The home is enhanced with numerous impact windows, filling the space with natural light and added peace of mind.Relax and unwind on the screened patio, or

    Diane Corliss Coldwell Banker Schmitt RE Co.

    27967 Coral Shores Rd, Little Torch Key, FL 33042
  • /18

    $480,000

    Sold Apr 01, 2026

    701 Spanish Main Dr Unit 384, Cudjoe Key, FL 33042

    • Land

    Last Sold Summary

    • 20% Below List Price
    • 126 Days On Market

    Current Estimated Value $512,079

    Last Listing Agent The Spottswood Team Truman & Co. (KW)

    701 Spanish Main Dr Unit 384, Cudjoe Key, FL 33042
    • /2

      Est $820,242

      Not Listed For Sale

      27087 Angelfish Rd, Summerland Key, FL 33042

      • 4 Beds
      • 2 Baths
      • 1,300 Sq Ft
      • Built 2020
      27087 Angelfish Rd, Summerland Key, FL 33042

      Last Sold Summary

      • 145 Days On Market

  • /4

    $1,050,000

    • 3 Beds
    • 2.5 Baths
    • 1,954 Sq Ft

    27403 Antigua Ln, Summerland Key, FL 33042

    Waterfront value-add opportunity in the Florida Keys with direct ocean access and no fixed bridges - perfect for serious boaters with vessels up to 60 feet. Situated on an oversize 18,000 SF lot, this property offers rare space, flexibility and future potential not commonly found in the Keys. The elevated concrete home features a spacious layout, multiple balconies, and abundant natural light

    Sonia Petraitis Caffroni Capital Intl Realty LLC

    27403 Antigua Ln, Summerland Key, FL 33042
  • /2

    $500,000

    Sold Jun 27, 2025

    538 Powell Ave, Summerland Key, FL 33042

    • 2 Beds
    • 1.5 Baths
    • 912 Sq Ft
    • Built 1987

    Last Sold Summary

    • 17% Below List Price
    • $548/SF
    • 62 Days On Market

    Current Estimated Value $769,368

    Last Listing Agent Sandra Tuttle Island Welcome Real Estate

    538 Powell Ave, Summerland Key, FL 33042
    • /69

      Not Listed For Sale

      701 Spanish Main Dr Unit 554, Cudjoe Key, FL 33042

      • 1 Bed
      • 1 Bath
      • 420 Sq Ft
      • Built 1988
      701 Spanish Main Dr Unit 554, Cudjoe Key, FL 33042

      Last Sold Summary

      • 461 Days On Market

  • /20

    $550,000

    $50K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 960 Sq Ft

    27910 Porgie Path, Summerland Key, FL 33042

    Great chance to own waterfront paradise with this elevated double-wide home situated on a rare double lot. Corner lot allows you to enjoy water on two sides of the property (plugged canals) —perfect for swimming, kayaking, paddle boarding, and relaxing by the water. Tucked away on a quiet cul-de-sac with lovely views, this property offers both privacy and charm, enhanced by mature landscaping.

    Alexis Seldin Xcellence

    27910 Porgie Path, Summerland Key, FL 33042
  • /46

    $998,000

    Sold Sep 09, 2025

    1117 Basque Ln, Cudjoe Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,318 Sq Ft
    • Built 2013

    Last Sold Summary

    • $757/SF
    • 16 Days On Market

    Current Estimated Value $1,031,814

    Last Listing Agent Lynn Goodwin, P.A. Key Colony Beach Realty

    1117 Basque Ln, Cudjoe Key, FL 33042
    • /66

      Not Listed For Sale

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

      • 2 Beds
      • Built 1978
      701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042

      Last Sold Summary

      • 78 Days On Market

  • /4

    $400,000

    • Land
    • 1,400 Acres
    • $286 per Acre

    27378 Jamaica Ln, Summerland Key, FL 33042

    ROGO and Building permit in hand! allows for immediate construction 6,000sq.ft lot on Ramrod Key, 60 feet of waterfront canal with quick access to ocean. Permit approved al Monroe County for a 1,400 sq.ft CBS 3 bedroom, 2.5 bath residence. Connected to water and sewer on site. ACOE and DEP mitigation paid. Permit for dock and lift submitted.Correct address: 27378 JAMAICA LN RAMROD KEY, FL

    Patricia Borges Borges Realty Group LLC

    27378 Jamaica Ln, Summerland Key, FL 33042
  • /6

    $14,500

    Sold Sep 29, 2025

    0 Vacant Land Unit 616529, Sugarloaf Key, FL 33042

    • Land
    • 6,010 Sq Ft
    • $105,077 per Acre

    Last Sold Summary

    • 7% Above List Price
    • 4 Days On Market

    Last Listing Agent Sam Williams Coldwell Banker Schmitt Real Estate Co.

    0 Vacant Land Unit 616529, Sugarloaf Key, FL 33042
    • /2

      Not Listed For Sale

      701 Spanish Main Dr Unit 559, Cudjoe Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 864 Sq Ft
      • Built 2001
      701 Spanish Main Dr Unit 559, Cudjoe Key, FL 33042

      Last Sold Summary

  • /51

    $1,250,000

    • 1 Bed
    • 3 Baths
    • 1,234 Sq Ft

    27001 Overseas Hwy, Ramrod Key, FL 33042

    Prime Lower Keys Commercial Property for sale on Ramrod Key. 3 Lots total 28,132 sf. or .65 acres with nearly 189' of frontage on Overseas Hwy aka Jimmy Buffett Memorial Hwy.!! Excellent visibility from the highway going both North and Southbound. This is a Corner lot at Coral Ave and Overseas Hwy with additional rear access off Old State Rd. 4A. Three sides with roads give this property ample

    Bobby Coe RE/MAX Keys Connection (KW)

    27001 Overseas Hwy, Ramrod Key, FL 33042
  • /37

    $800,000

    Sold Dec 19, 2025

    923 Indies Rd, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,079 Sq Ft
    • Built 2002

    Last Sold Summary

    • 6% Below List Price
    • $741/SF
    • 60 Days On Market

    Current Estimated Value $810,968

    Last Listing Agent Christina Davis Coldwell Banker Schmitt RE Co.

    923 Indies Rd, Summerland Key, FL 33042
    • /2

      Not Listed For Sale

      701 Spanish Main Dr Unit 537, Cudjoe Key, FL 33042

      • 1 Bed
      • 1 Bath
      • 520 Sq Ft
      • Built 2000
      701 Spanish Main Dr Unit 537, Cudjoe Key, FL 33042

      Last Sold Summary

  • /17

    $255,000

    $10K PRICE DROP
    • Land
    • 2,178 Sq Ft
    • $5,100,000 per Acre

    701 Spanish Main Dr Unit 643, Cudjoe Key, FL 33042

    Welcome to island living at its best! This 35'x 69' RV lot is ready for your rig with full hookups and all the perks of Venture Out—golf cart streets, 24-hour security, pool, tennis, pickleball, and a marina. Located minutes from local favorites Morning Joint, Square Grouper, and 420 Lounge, plus only 19 miles to Key West. Whether you're here for fishing, boating, or simply soaking in the Keys

    Jenifer Hirsch Bluescape Real Estate

    701 Spanish Main Dr Unit 643, Cudjoe Key, FL 33042
  • /42

    $1,750,000

    Sold Feb 26, 2026

    20771 2nd Ave W, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 2,047 Sq Ft
    • Built 2010

    Last Sold Summary

    • 17% Below List Price
    • $855/SF
    • 161 Days On Market

    Current Estimated Value $1,795,710

    Last Listing Agent Sandra Tuttle Island Welcome Real Estate

    20771 2nd Ave W, Summerland Key, FL 33042
    • /46

      Est $1,922,781

      Not Listed For Sale

      271 W Indies Dr, Ramrod Key, FL 33042

      • 4 Beds
      • 4 Baths
      • 2,358 Sq Ft
      • Built 2023
      271 W Indies Dr, Ramrod Key, FL 33042

      Last Sold Summary

      • 342 Days On Market

  • /58

    $276,900

    $18K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 316 Sq Ft

    701 Spanish Main Dr Unit LOT 423, Cudjoe Key, FL 33042

    INCOME PRODUCING POWERHOUSE! Welcome to 'Conch Hideaway' #423, a proven tropical retreat and turnkey business in the premier Venture Out community. This charming 1BD/1BA home is a high-performing vacation rental that grossed $30,705 in 2025! INVESTMENT HIGHLIGHTS: Already live with rentals for 2026, this property has 27 days currently booked with $2,085.05 in gross revenue transferring to the

    Kate Baldwin Bluescape Real Estate

    701 Spanish Main Dr Unit LOT 423, Cudjoe Key, FL 33042
  • /47

    $520,000

    Sold Sep 04, 2025

    27853 Coral Shores Rd, Little Torch Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 960 Sq Ft
    • Built 1979

    Last Sold Summary

    • 7% Below List Price
    • $542/SF
    • 117 Days On Market

    Last Listing Agent Leah Scarborough Island Welcome Real Estate

    27853 Coral Shores Rd, Little Torch Key, FL 33042
    • /35

      Not Listed For Sale

      701 Spanish Main Dr Unit 48, Cudjoe Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 849 Sq Ft
      • Built 1992
      701 Spanish Main Dr Unit 48, Cudjoe Key, FL 33042

      Last Sold Summary

      • 191 Days On Market

  • /125

    $5,200,000

    $1M PRICE DROP Under Contract
    • 5 Beds
    • 6 Baths
    • 3,000 Sq Ft

    24200 Overseas Hwy, Summerland Key, FL 33042

    Welcome to an unparalleled coastal lifestyle, where modern luxury meets the ultimate boater's paradise. This extraordinary compound, nestled along a prime stretch of the Florida Keys waterfront, has been completely reimagined for the discerning owner who demands both sophisticated living spaces and robust functionality. This pristine oceanfront estate is situated on a manicured one-acre gated

    Sylvia Werling Keller Williams Key West Compass Realty

    24200 Overseas Hwy, Summerland Key, FL 33042
  • /43

    $975,000

    Sold May 30, 2025

    17425 Jamaica Ln, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,440 Sq Ft
    • Built 2018

    Last Sold Summary

    • 19% Below List Price
    • $677/SF
    • 65 Days On Market

    Current Estimated Value $1,006,025

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    17425 Jamaica Ln, Summerland Key, FL 33042
    • /58

      Est $1,763,164

      Not Listed For Sale

      1106 Thatch Ln, Summerland Key, FL 33042

      • 4 Beds
      • 3.5 Baths
      • 2,548 Sq Ft
      • Built 2016
      1106 Thatch Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 50 Days On Market

  • /45

    $7,000,000

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

    0 Melody Key Unit 616249, Summerland Key, FL 33042

    An unparalleled opportunity to own your own private island in the Florida Keys. Melody Key is a true rarity--an off-grid sanctuary offering complete privacy, turquoise waters in every direction, and now a brand-new boat dock and observation deck that set the stage for its next chapter.The property is currently undergoing a full renovation with permits and detailed architectural drawings already

    Scott Forman Royal Palms Realty (KW)

    0 Melody Key Unit 616249, Summerland Key, FL 33042
  • /43

    $815,000

    Sold Jan 23, 2026

    681 W Indies Dr, Summerland Key, FL 33042

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

    Last Sold Summary

    • 18% Below List Price
    • $894/SF
    • 211 Days On Market

    Current Estimated Value $806,912

    Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

    681 W Indies Dr, Summerland Key, FL 33042
    • /6

      Not Listed For Sale

      Lot 27 Angelfish Rd, Ramrod Key, FL 33042

      Lot 27 Angelfish Rd, Ramrod Key, FL 33042

      Last Sold Summary

      • 291 Days On Market

  • /14

    $395,000

    • Land
    • 6,098 Sq Ft
    • $2,821,429 per Acre

    24285 Caribbean Dr, Summerland Key, FL 33042

    Purchase this deep draft canal front LOT in Summerland Key in the Florida Keys. The building permit is in-process for a 3 bedroom/ 2 bath stilted single family residence (cost of the home is additional). The plans shown are for a 1320 sq ft' 3/2 elevated Affinity home with features that include impact doors and windows and built to 180 mph which is great for your insurance rates. This canal has

    Donna Pezzi Keller Williams Key West Compass Realty

    24285 Caribbean Dr, Summerland Key, FL 33042
  • /58

    $3,335,000

    Sold Jun 13, 2025

    23971 Henry St, Summerland Key, FL 33042

    • 4 Beds
    • 4 Baths
    • 2,950 Sq Ft
    • Built 1956

    Last Sold Summary

    • 2% Below List Price
    • $1,131/SF
    • 37 Days On Market

    Current Estimated Value $3,197,257

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    23971 Henry St, Summerland Key, FL 33042
    • /30

      Est $796,838

      Not Listed For Sale

      124 Yardarm Rd, Cudjoe Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,064 Sq Ft
      • Built 2023
      124 Yardarm Rd, Cudjoe Key, FL 33042

      Last Sold Summary

      • 22 Days On Market

  • /49

    $275,000

    $5K PRICE DROP Under Contract
    • 1 Bed
    • 1 Bath
    • 690 Sq Ft

    701 Spanish Main Dr Unit 21, Cudjoe Key, FL 33042

    Welcome to your slice of Paradise in the florida Keys! This cozy one bed/one bath mobile home is located in the highly desirable Venture Out gated community on Cudjoe Key. Thoughtfully designed and fully furnished, this home comfortably sleeps four and is in move-in ready. Enjoy the bright and inviting Florida room featuring durable Hardie board siding, along with a covered tile patio outback,

    Kim Babenzien Expert Realty LLC (HQ)

    701 Spanish Main Dr Unit 21, Cudjoe Key, FL 33042

Showing Results 241 - 280, Page 7 of 18

How to Buy a Home How to Finance a Home How to Sell a Home