6,959

Homes in ZIP Code 33042

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  • /17

    $255,000

    • Land

    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

    Bea Evelyn Citron Compass Florida, LLC

    701 Spanish Main Dr Unit 643, Cudjoe Key, FL 33042
  • /45

    $799,000 Sold Aug 29, 2025

    17338 Dolphin St E, Summerland Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 1,875 Sq Ft
    • Built 1963

    Last Sold Summary

    • 30% Below List Price
    • $426/SF
    • 171 Days On Market

    Current Estimated Value $900,456

    Last Listing Agent Alexa Morgan Buy The Keys

    17338 Dolphin St E, Summerland Key, FL 33042
    • /37

      Est $1,231,212 Not Listed For Sale

      716 Caribbean Dr E, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 1,368 Sq Ft
      • Built 1983
      716 Caribbean Dr E, Summerland Key, FL 33042

      Last Sold Summary

      • 12% Above List Price
      • $803/SF
      • 19 Days On Market

      Last Sold Price $1,099,000

      Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

  • /58

    $295,000

    • 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

    $1,075,000 Sold Jul 30, 2025

    128 Le Grand Ln, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft
    • Built 1999

    Last Sold Summary

    • 16% Below List Price
    • $960/SF
    • 189 Days On Market

    Current Estimated Value $1,093,305

    Last Listing Agent Alain Majeau Berkshire Hathaway HomeServices Knight & Gardner Realty

    128 Le Grand Ln, Summerland Key, FL 33042
    • /40

      Est $2,177,676 Not Listed For Sale

      20995 2nd Ave W, Summerland Key, FL 33042

      • 3 Beds
      • 2.5 Baths
      • 2,184 Sq Ft
      • Built 2007
      20995 2nd Ave W, Summerland Key, FL 33042

      Last Sold Summary

      • 5% Above List Price
      • $1,053/SF
      • 6 Days On Market

      Last Sold Price $2,300,000

      Last Listing Agent Gloria Sellers Berkshire Hathaway HomeServices Knight & Gardner Realty

  • /129

    $6,200,000

    • 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
  • /40

    $940,000 Sold Jun 02, 2025

    763 Diane Ave, Little Torch Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,188 Sq Ft
    • Built 2012

    Last Sold Summary

    • 6% Below List Price
    • $791/SF
    • 15 Days On Market

    Current Estimated Value $942,069

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    763 Diane Ave, Little Torch Key, FL 33042
    • /49

      Est $6,696,546 Not Listed For Sale

      17279 Oleander Ln, Sugarloaf Key, FL 33042

      • 10 Beds
      • 11.5 Baths
      • 10,607 Sq Ft
      • Built 1992
      17279 Oleander Ln, Sugarloaf Key, FL 33042

      Last Sold Summary

      • 10% Above List Price
      • $698/SF
      • 7 Days On Market

      Last Sold Price $7,400,000

      Last Listing Agent Lisa Swanson The Agency Florida Keys

  • /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
  • /34

    $762,000 Sold Jan 22, 2026

    726 Jamaica Ln, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,568 Sq Ft
    • Built 1986

    Last Sold Summary

    • 15% Below List Price
    • $486/SF
    • 325 Days On Market

    Current Estimated Value $787,036

    Last Listing Agent Natallie Liz Expert Realty LLC (HQ)

    726 Jamaica Ln, Summerland Key, FL 33042
    • /40

      Est $926,433 Not Listed For Sale

      93 Venetian Way, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,632 Sq Ft
      • Built 1983
      93 Venetian Way, Summerland Key, FL 33042

      Last Sold Summary

      • 18% Above List Price
      • $481/SF
      • 11 Days On Market

      Last Sold Price $785,000

      Last Listing Agent Heather Mason Coastal Collection Real Estate Inc.

  • /49

    $275,000

    • 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
  • /40

    $1,115,000 Sold Sep 10, 2025

    28552 Maracaibo Rd, Little Torch Key, FL 33042

    • 2 Beds
    • 2 Baths
    • 988 Sq Ft
    • Built 1989

    Last Sold Summary

    • 3% Below List Price
    • $1,129/SF
    • 8 Days On Market

    Current Estimated Value $1,105,464

    Last Listing Agent Teri Hiller Coldwell Banker Schmitt Real Estate Co.

    28552 Maracaibo Rd, Little Torch Key, FL 33042
    • /48

      Est $620,278 Not Listed For Sale

      27018 Angelfish Rd, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 960 Sq Ft
      • Built 1992
      27018 Angelfish Rd, Summerland Key, FL 33042

      Last Sold Summary

      • 1% Below List Price
      • $651/SF
      • 15 Days On Market

      Last Sold Price $625,000

      Last Listing Agent Monica Barrett Coldwell Banker Schmitt Real Estate Co.

  • /43

    $1,050,000

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

    22837 Calico Jack Cir, Summerland Key, FL 33042

    Open Water Views & Sunset Skies with great boating access describes this Concrete Block Construction Home with pre-stress concrete beams holding up a poured concrete floor. Home features open floor plan with vaulted ceilings, tile floors throughout, partial walk-around, storm shutters, 2018 A/C, impact front door and metal roof. Storage room below and ample parking too. Quick commute to Key West,

    Beata Sharpe Coldwell Banker Vanguard Realty

    22837 Calico Jack Cir, Summerland Key, FL 33042
  • /42

    $775,000 Sold Oct 01, 2025

    22988 Port Royal Ln, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,122 Sq Ft
    • Built 1998

    Last Sold Summary

    • 6% Below List Price
    • $691/SF
    • 68 Days On Market

    Current Estimated Value $779,721

    Last Listing Agent Walter Ceballos, P.A. Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

    22988 Port Royal Ln, Summerland Key, FL 33042
    • /19

      Est $895,009 Not Listed For Sale

      221 Cutthroat Dr, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 1,056 Sq Ft
      • Built 1985
      221 Cutthroat Dr, Summerland Key, FL 33042

      Last Sold Summary

      • 4% Above List Price
      • $881/SF
      • 498 Days On Market

      Last Sold Price $930,000

      Last Listing Agent Aryl and Pati Robison RE/MAX

  • /9

    $475,000

    • Land

    27460 W Indies Dr, Ramrod Key, FL 33042

    Anay Ramos Miami New Realty

    27460 W Indies Dr, Ramrod Key, FL 33042
  • /77

    $2,500,000 Sold Jul 15, 2025

    943 Flagship Dr, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,792 Sq Ft
    • Built 2001

    Last Sold Summary

    • 7% Below List Price
    • $1,395/SF
    • 121 Days On Market

    Current Estimated Value $2,511,873

    Last Listing Agent Lisa Swanson The Agency Florida Keys

    943 Flagship Dr, Summerland Key, FL 33042
    • /2

      Est $1,118,149 Not Listed For Sale

      27310 W Indies Dr, Summerland Key, FL 33042

      • 2 Beds
      • 3 Baths
      • 1,120 Sq Ft
      • Built 1984
      27310 W Indies Dr, Summerland Key, FL 33042

      Last Sold Summary

      • 6% Below List Price
      • $1,058/SF

      Last Sold Price $1,185,000

      Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  • /24

    $259,000

    • Land

    701 Spanish Main Dr Unit 69, Cudjoe Key, FL 33042

    RV Lot or Build your home here in the private, gated community of Venture Out on Cudjoe Key. 35' x 69' paved and cleared lot. Nightly rentals allowed here! Many amenities on-site including a boat ramp, marina store and fuel station. Basketball, bocce, tennis and pickleball courts. Heated saltwater swimming pool right by the ocean. Venture Out is a golf cart friendly community. There are always

    Ian Calderwood Bluescape Real Estate

    701 Spanish Main Dr Unit 69, Cudjoe Key, FL 33042
  • /39

    $650,000 Sold Apr 25, 2025

    25161 Center St, Summerland Key, FL 33042

    • 1 Bed
    • 1.5 Baths
    • 1,024 Sq Ft
    • Built 1958

    Last Sold Summary

    • 4% Below List Price
    • $635/SF
    • 6 Days On Market

    Current Estimated Value $628,335

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

    25161 Center St, Summerland Key, FL 33042
    • /36

      Est $917,266 Not Listed For Sale

      27328 Jamaica Ln, Summerland Key, FL 33042

      • 3 Beds
      • 3 Baths
      • 1,518 Sq Ft
      • Built 1979
      27328 Jamaica Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 23% Below List Price
      • $787/SF
      • 22 Days On Market

      Last Sold Price $1,195,000

      Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

  • /24

    $350,000 Under Contract

    • Land

    701 Spanish Main Dr Unit 181, Cudjoe Key, FL 33042

    The Ultimate Canal-Front RV Oasis in Venture Out at Cudjoe KeySeller says bring offers..Escape to your own slice of paradise with this prime waterfront RV lot in the sought-after, gated community of Venture Out on Cudjoe Key. This lot is built for the avid water enthusiast and provides a perfect base for exploring the best of the Lower and Middle Florida Keys.Fully Prepped RV Pad: Bring your rig

    Carmen Brake Waterfront Keys Realty Inc.

    701 Spanish Main Dr Unit 181, Cudjoe Key, FL 33042
  • /41

    $970,000 Sold May 27, 2025

    366 Sawyer Dr, Summerland Key, FL 33042

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

    Last Sold Summary

    • 19% Below List Price
    • $698/SF
    • 4 Days On Market

    Current Estimated Value $1,009,209

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

    366 Sawyer Dr, Summerland Key, FL 33042
    • /61

      Est $1,993,494 Not Listed For Sale

      17153 Buttonwood Dr W, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,426 Sq Ft
      • Built 1998
      17153 Buttonwood Dr W, Summerland Key, FL 33042

      Last Sold Summary

      • 5% Above List Price
      • $1,473/SF
      • 30 Days On Market

      Last Sold Price $2,100,000

      Last Listing Agent Daniel Urban Expert Realty LLC (HQ)

  • /2

    $275,000

    • Land

    0 Disturbed Pine Rd Unit 619097, Cudjoe Key, FL 33042

    Builders and Developers take a look at this 24 point lot that has a letter from Monroe County to be used toward building in the ROGO system. Contact Monroe County Building Department and/or the Monroe County Planning Department to verify use of this point lot. A great deal for anyone needing points to be competitive in the ROGO system.

    Pamela Stangler Expert Realty LLC

    0 Disturbed Pine Rd Unit 619097, Cudjoe Key, FL 33042
  • /38

    $1,600,000 Sold Feb 06, 2026

    27314 Saint Lucie Ln, Ramrod Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,666 Sq Ft
    • Built 2025

    Last Sold Summary

    • 6% Below List Price
    • $960/SF
    • 109 Days On Market

    Current Estimated Value $1,604,121

    Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

    27314 Saint Lucie Ln, Ramrod Key, FL 33042
    • /39

      Est $1,724,582 Not Listed For Sale

      17056 Wahoo Ln, Summerland Key, FL 33042

      • 2 Beds
      • 2.5 Baths
      • 1,426 Sq Ft
      • Built 1992
      17056 Wahoo Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 24% Above List Price
      • $978/SF
      • 232 Days On Market

      Last Sold Price $1,395,000

      Last Listing Agent Lisa Swanson The Agency Florida Keys

  • /34

    $469,000

    • 1 Bed
    • 1.5 Baths
    • 735 Sq Ft

    701 Spanish Main Dr Unit 548, Cudjoe Key, FL 33042

    Welcome to your opportunity in the gated waterfront community of Venture Out! This 1 bedroom, 1.5 bath property offers 35 feet of concrete seawall and direct canal access -- making it a true gem for boating enthusiasts and water lovers alike.Whether you're an investor searching for your next income-producing property or a creative buyer ready to design your own slice of paradise, this home offers

    Bea Evelyn Citron Compass Florida, LLC

    701 Spanish Main Dr Unit 548, Cudjoe Key, FL 33042
  • /62

    $1,035,000 Sold Apr 01, 2026

    231 W Indies Dr, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,377 Sq Ft
    • Built 1990

    Last Sold Summary

    • 4% Below List Price
    • $752/SF
    • 173 Days On Market

    Current Estimated Value $1,048,293

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

    231 W Indies Dr, Summerland Key, FL 33042
    • /81

      Est $1,309,362 Not Listed For Sale

      23041 Snapper Ln, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,664 Sq Ft
      • Built 1992
      23041 Snapper Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 19% Below List Price
      • $977/SF
      • 11 Days On Market

      Last Sold Price $1,625,000

      Last Listing Agent Tommy Mack Coastal Collection Real Estate Inc.

  • /32

    $1,125,000

    • 2 Beds
    • 2 Baths
    • 1,175 Sq Ft

    27821 Leeward South Rd, Little Torch Key, FL 33042

    ***OPEN HOUSE*** Saturday March 28th 10am-12pm. Location Location Location! This property offers lots of space, tons of privacy and stunning views. This home is situated on 2.38 acres of land with breathtaking open water views. Walk on to your newly refinished composite stairs to a walk around porch. Making access to the exterior of the home super easy. Interior layout is a large open floor plan

    Tracy Shields KeyIsle Realty

    27821 Leeward South Rd, Little Torch Key, FL 33042
  • /58

    $835,000 Sold May 28, 2025

    23920 Overseas Hwy, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,242 Sq Ft
    • Built 2022

    Last Sold Summary

    • 2% Below List Price
    • $672/SF
    • 60 Days On Market

    Current Estimated Value $868,963

    Last Listing Agent Aleida Ramirez United Realty Group Inc

    23920 Overseas Hwy, Summerland Key, FL 33042
    • /19

      Est $818,477 Not Listed For Sale

      22910 Privateer Dr, Summerland Key, FL 33042

      • 2 Beds
      • 2 Baths
      • 960 Sq Ft
      • Built 1988
      22910 Privateer Dr, Summerland Key, FL 33042

      Last Sold Summary

      • 3% Below List Price
      • $881/SF
      • 58 Days On Market

      Last Sold Price $846,000

      Last Listing Agent Robin Nilsson Keller Williams Key West Compass Realty

  • /24

    $580,175

    • 2 Beds
    • 2 Baths
    • 816 Sq Ft

    701 Spanish Main Dr Unit 79, Cudjoe Key, FL 33042

    Licensed Nightly Rental Property!! Discover island living at 701 Spanish Main Dr, Unit 79 in Cudjoe Key, FL. This charming property offers an unbeatable opportunity for investors or those seeking a tranquil retreat. Currently operating as a successful vacation rental, this home is perfectly positioned to generate income or serve as your own private oasis. This property promises both convenience

    Sarah Dolson Keller Williams Key West Compass Realty

    701 Spanish Main Dr Unit 79, Cudjoe Key, FL 33042
  • /35

    $945,000 Sold May 15, 2025

    17182 Starfish Ln W, Summerland Key, FL 33042

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

    Last Sold Summary

    • 3% Below List Price
    • $747/SF
    • 6 Days On Market

    Current Estimated Value $970,628

    Last Listing Agent Daniel Urban Expert Realty LLC (HQ)

    17182 Starfish Ln W, Summerland Key, FL 33042
    • /2

      Est $1,533,495 Not Listed For Sale

      27362 Anguila Ln, Summerland Key, FL 33042

      • 3 Beds
      • 2 Baths
      • 1,842 Sq Ft
      • Built 1975
      27362 Anguila Ln, Summerland Key, FL 33042

      Last Sold Summary

      • 14% Below List Price
      • $964/SF

      Last Sold Price $1,775,000

      Last Listing Agent Carolyn Quelly Coastal Collection Real Estate Inc.

  • /76

    $859,999

    • 2 Beds
    • 1.5 Baths
    • 1,500 Sq Ft

    19512 Aztec St, Summerland Key, FL 33042

    Motivated seller! Bring all Reasonable offers 2 bedrooms, 1.5 baths with a 500sq ft screened lanai in the main building. There are 2 additional buildings that could be used as offices or bedrooms. Custom Pool with jacuzzi and swim jet. Completely remodeled in 2020 with new roof, new A/C. Located in the established Indian Mound Estates neighborhood w/ Access to private boat ramp with cabana and

    Nick Boumerhi Meyer and Boumerhi Realty LLC

    19512 Aztec St, Summerland Key, FL 33042

Showing Results 321 - 360, Page 9 of 18

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