Homes in ZIP Code 33042

• 

  

  

  /4

  $100,000

  • Land
  • 1.01 Acres
  • $99,010 per Acre

  0 Acosta Trail Unit MFRS5141973, Sugarloaf Key, FL 33042

  Vacant 1.01-acre parcel on Acosta Trail in Upper Sugarloaf Key, Monroe County, FL. Approx. 20 miles to Key West, 10 miles to Big Pine Key, and 5 miles to Cudjoe Key. Unimproved land offering future development or investment potential in the Lower Florida Keys. Additional 1.01-acre lot on Mira Rd (behind subject property) also available for sale. Buyer to verify zoning, ROGO status, flood zone,

  Eugenia Hernandez PREMIUM PROPERTIES R.E SERVICE

  0 Acosta Trail Unit MFRS5141973, Sugarloaf Key, FL 33042
• 

  

  

  /85

  $1,800,000 Sold Jan 23, 2026

  17054 Coral Dr, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,422 Sq Ft
  • Built 2004

  Last Sold Summary

  • 10% Below List Price
  • $743/SF
  • 240 Days On Market

  Current Estimated Value $1,816,010

  Last Listing Agent Will Langley Berkshire Hathaway HomeServices Knight & Gardner Realty

  17054 Coral Dr, Summerland Key, FL 33042
• 

  

  

  /43

  Est $1,398,326 Not Listed For Sale

  408 Sawyer Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,330 Sq Ft
  • Built 1989

  408 Sawyer Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 7% Below List Price
  • $1,128/SF
  • 16 Days On Market

  Last Sold Price $1,500,000

  Last Listing Agent Kathryn Baldwin Bluescape Real Estate
• 

  

  

  /47

  $1,200,000

  • 3 Beds
  • 2 Baths
  • 1,250 Sq Ft

  43 Venetian Way, Summerland Key, FL 33042

  Beautifully updated 3 bedroom 2 bath home, with effective build date of 2015 and completely renovated in 2018 including New Electrical, Plumbing, HVAC, Roof, Tankless Water heater, Flooring, Kitchen, Bathrooms, Windows, & Doors, landscaping/sprinkler system, TESLA charging station and an amazing new paved driveway installed in 2021. This is a split floor plan for privacy with amazing screened in

  Lori Cameron Buy The Keys

  43 Venetian Way, Summerland Key, FL 33042
• 

  

  

  /50

  $1,100,000 Sold Mar 06, 2026

  19749 Date Palm Dr, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,464 Sq Ft
  • Built 2017

  Last Sold Summary

  • 15% Below List Price
  • $446/SF
  • 151 Days On Market

  Current Estimated Value $1,292,157

  Last Listing Agent Richard Lively Coldwell Banker Schmitt Real Estate Co. (KW)

  19749 Date Palm Dr, Summerland Key, FL 33042
• 

  

  /14

  Est $2,884,713 Not Listed For Sale

  683 Sawyer Dr, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 1,561 Sq Ft
  • Built 1985

  683 Sawyer Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 4% Above List Price
  • $1,922/SF
  • 22 Days On Market

  Last Sold Price $3,000,000

  Last Listing Agent Ashkarian Ardis Team Coldwell Banker Schmitt Real Estate Co.
• 

  

  /3

  $799,000

  • Land
  • 10 Acres
  • $79,900 per Acre

  LOT 57 Rocky Rd, Sugarloaf Key, FL 33042

  Rare opportunity to acquire approximately 10 acres of vacant residential land in Sugarloaf Key, an area known for its low-density character, natural surroundings, and limited land availability. Large parcels of this size are increasingly scarce in the Lower Florida Keys, positioning this property as a strategic long-term holding or future planning opportunity. On Monroe county records, the

  Eugenia Hernandez PREMIUM PROPERTIES R.E SERVICE

  LOT 57 Rocky Rd, Sugarloaf Key, FL 33042
• 

  /2

  $1,299,000 Sold Jan 28, 2026

  28532 Dirk Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,530 Sq Ft
  • Built 1985

  Last Sold Summary

  • $849/SF
  • 5 Days On Market

  Current Estimated Value $1,297,747

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  28532 Dirk Rd, Summerland Key, FL 33042
• 

  

  /32

  Est $1,968,703 Not Listed For Sale

  21018 4th Ave, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,966 Sq Ft
  • Built 1994

  21018 4th Ave, Summerland Key, FL 33042

  Last Sold Summary

  • 24% Above List Price
  • $534/SF
  • 302 Days On Market

  Last Sold Price $1,585,000

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

  

  /12

  $495,000

  • Land

  701 Spanish Main Dr Unit 84, Cudjoe Key, FL 33042

  Rare opportunity to own a transient (1-day minimum) rental RV lot in the Lower Keys. Located in a quiet, well-kept community, this buildable lot is perfect for your RV or for building a custom Keys getaway HomeThe property includes a 35-foot concrete seawall, dock posts, fishing cleaning station, swim ladder, Brand new concrete slab and full hookups with water, sewer, and 30, 50, and 110-amp

  Anay Ramos Miami New Realty

  701 Spanish Main Dr Unit 84, Cudjoe Key, FL 33042
• 

  

  /66

  $3,275,000 Sold Oct 28, 2025

  20816 4th Ave W, Cudjoe Key, FL 33042

  • 5 Beds
  • 4 Baths
  • 3,817 Sq Ft
  • Built 2021

  Last Sold Summary

  • 32% Below List Price
  • $858/SF
  • 206 Days On Market

  Current Estimated Value $3,233,047

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

  20816 4th Ave W, Cudjoe Key, FL 33042
• 

  

  /8

  Est $723,943 Not Listed For Sale

  19514 Canal Dr, Summerland Key, FL 33042

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Built 1995

  19514 Canal Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 3% Above List Price
  • $583/SF
  • 76 Days On Market

  Last Sold Price $700,000

  Last Listing Agent Michell Gonzalez Keller Williams Key West Compass Realty
• 

  

  /54

  $895,999

  • 2 Beds
  • 2 Baths
  • 1,520 Sq Ft

  17326 Jamaica Ln, Summerland Key, FL 33042

  Welcome to your slice of Lower Keys paradise--just 17 miles from Key West yet worlds away from the hustle. This elevated 2-bedroom, 2-bath home sits on a generous lot in a fantastic neighborhood, offering the perfect blend of comfort, style, and island living.Inside, vaulted ceilings and impact windows fill the home with natural light and breezy tropical charm. An elevator makes access

  Stephanie Wise Keller Williams Key West Compass Realty

  17326 Jamaica Ln, Summerland Key, FL 33042
• 

  

  /29

  $1,300,000 Sold Jan 09, 2026

  141 Arica Ln, Cudjoe Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,674 Sq Ft
  • Built 2010

  Last Sold Summary

  • 6% Below List Price
  • $777/SF
  • 19 Days On Market

  Current Estimated Value $1,308,726

  Last Listing Agent Madeleine Lowe Expert Realty LLC (HQ)

  141 Arica Ln, Cudjoe Key, FL 33042
• 

  

  /26

  Est $506,545 Not Listed For Sale

  19910 Flamingo Rd, Summerland Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 690 Sq Ft
  • Built 1947

  19910 Flamingo Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 7% Above List Price
  • $687/SF
  • 10 Days On Market

  Last Sold Price $474,000

  Last Listing Agent Melissa Graham Bluescape Real Estate
• 

  

  /10

  $1,450,000

  • Land

  00000 Lagoon Dr, Summerland Key, FL 33042

  Excellent opportunity to build your dream in paradise. This 6,140 sq foot lot with 70.65 ft. of water frontage has a beautiful open water and ocean view. This is the last lot available in this established subdivision Summerland Cove. Easy access to both the Atlantic Ocean and the Gulf of Mexico.

  Marc Ulanowski Equestrian Sotheby's International Realty

  00000 Lagoon Dr, Summerland Key, FL 33042
• 

  

  /29

  $980,000 Sold May 29, 2025

  1107 Hawksbill Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1984

  Last Sold Summary

  • 11% Below List Price
  • $851/SF
  • 54 Days On Market

  Current Estimated Value $1,018,341

  Last Listing Agent Richard Haskins Buy The Keys

  1107 Hawksbill Ln, Summerland Key, FL 33042
• 

  

  /26

  Est $1,241,552 Not Listed For Sale

  105 S Point Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,424 Sq Ft
  • Built 1984

  105 S Point Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 6% Above List Price
  • $823/SF
  • 31 Days On Market

  Last Sold Price $1,172,000

  Last Listing Agent Krystal Thomas eXp Realty LLC
• 

  

  /39

  $899,000

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft

  437 Pirates Rd, Little Torch Key, FL 33042

  Offered in the highly sought-after Jolly Roger Estates, this beautifully maintained, one-owner canal-front home is just 11 years old and truly move-in ready. Elevated and thoughtfully designed, the 1,296 sq. ft. residence offers three bedrooms and two bathrooms, enhanced by refined finishes including crown molding, tray ceilings, tile showers, and a bright, open-concept living space ideal for

  Jo Ann Cook Ocean Sotheby's International Realty

  437 Pirates Rd, Little Torch Key, FL 33042
• 

  

  /52

  $1,650,000 Sold Jan 28, 2026

  17213 Starfish Ln E, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,750 Sq Ft
  • Built 1993

  Last Sold Summary

  • 15% Below List Price
  • $943/SF
  • 111 Days On Market

  Current Estimated Value $1,658,508

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

  17213 Starfish Ln E, Summerland Key, FL 33042
• 

  /2

  Est $1,702,373 Not Listed For Sale

  17150 La Brisa Ct, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 1,810 Sq Ft
  • Built 1980

  17150 La Brisa Ct, Summerland Key, FL 33042

  Last Sold Summary

  • 7% Below List Price
  • $1,017/SF

  Last Sold Price $1,840,000

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co
• 

  

  /48

  $875,000 Open Sat 11AM - 3PM

  • 2 Beds
  • 2 Baths
  • 912 Sq Ft

  538 Powell Ave, Summerland Key, FL 33042

  This beautifully renovated 2-bedroom and 2-bath canal-front home on the Gulf-side of Little Torch Key is ready for you and your boat. The 37-foot-wide canal is clean and clear, with easy access to both the Atlantic and Gulf, and there is a wonderful boat ramp nearby. Engineered plans have also been filed and paid for your very own dock and 15,000 pound boat lift. The 60-foot-wide x 110-deep

  Jonathan Minerick Homecoin.com

  538 Powell Ave, Summerland Key, FL 33042
• 

  

  /41

  $1,000,000 Sold Sep 23, 2025

  237 La Fitte Rd, Summerland Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 1,144 Sq Ft
  • Built 1973

  Last Sold Summary

  • 17% Below List Price
  • $874/SF
  • 162 Days On Market

  Current Estimated Value $1,063,920

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  237 La Fitte Rd, Summerland Key, FL 33042
• 

  

  /40

  Est $838,308 Not Listed For Sale

  17236 Keystone Rd, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,155 Sq Ft
  • Built 1974

  17236 Keystone Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 7% Above List Price
  • $680/SF
  • 184 Days On Market

  Last Sold Price $785,000

  Last Listing Agent Everett Watkins Keller Williams Key West Compass Realty
• 

  

  /25

  $730,000

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

  180 Sugarloaf Dr, Summerland Key, FL 33042

  **Motivated Sellers, all reasonable offers considered**This charming 3 bedroom 2 bath house in Sugarloaf Shores sits on an oversized 12,000sqft lot. Fenced for privacy with plenty of room for a pool, park your boat or RV. Outside you have a quaint patio, outdoor shower and lush gardens. Step inside to find a warm inviting interior space, remodeled kitchen, bonus screened porch and outdoor seating

  Jenny Perry Preferred Properties (KW)

  180 Sugarloaf Dr, Summerland Key, FL 33042
• 

  

  /69

  $1,700,000 Sold Jan 02, 2026

  620 Barry Ave, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,120 Sq Ft
  • Built 2025

  Last Sold Summary

  • 5% Below List Price
  • $802/SF
  • 26 Days On Market

  Current Estimated Value $1,696,191

  Last Listing Agent Kelly Gardner Bluescape Real Estate

  620 Barry Ave, Summerland Key, FL 33042
• 

  /2

  Est $843,333 Not Listed For Sale

  17036 Wahoo Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,840 Sq Ft
  • Built 1965

  17036 Wahoo Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 36% Below List Price
  • $720/SF

  Last Sold Price $1,325,000

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co
• 

  

  /4

  $750,000

  • 3 Beds
  • 2 Baths
  • 960 Sq Ft

  53 Treasure Chest Dr, Summerland Key, FL 33042

  53 Treasure Chest Drive in Cudjoe Key is more than a home--it's your chance to own a piece of paradise. From the moment you arrive, you'll feel the laid-back island vibe paired with the comfort and security today's buyers demand, including impact windows and doors for year-round peace of mind.Bright, airy, and designed for easy living, this property invites you to slow down, entertain more, and

  Mary Bryant Keller Williams Key West Compass Realty

  53 Treasure Chest Dr, Summerland Key, FL 33042
• 

  

  /4

  $175,000 Sold Dec 23, 2025

  Lot 2 Overseas Hwy, Summerland Key, FL 33042

  • Land

  Last Sold Summary

  • 15% Below List Price
  • 25 Days On Market

  Last Listing Agent Sarah Eckert Coldwell Banker Schmitt Real Estate Co. (KW)

  Lot 2 Overseas Hwy, Summerland Key, FL 33042
• 

  

  /37

  Est $2,016,700 Not Listed For Sale

  17026 Bonita Ln W, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,638 Sq Ft
  • Built 1989

  17026 Bonita Ln W, Summerland Key, FL 33042

  Last Sold Summary

  • 8% Below List Price
  • $1,343/SF
  • 32 Days On Market

  Last Sold Price $2,200,000

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co
• 

  

  /37

  $879,000

  • 2 Beds
  • 2 Baths
  • 861 Sq Ft

  701 Spanish Main Dr Unit 512, Cudjoe Key, FL 33042

  VACATION RENTAL OPPORTUNITY - OPEN WATER VIEWS + 43' DOCK - 2BR/2BA | 864 SQ. FT.Beautifully maintained 2-bedroom, 2-bath waterfront home offering open water views and excellent rental potential. This 864 sq. ft. property features a 43-foot dock with quick access to world-class boating, fishing, and diving in the Florida Keys. Ideal for investors or owners seeking a turn-key vacation rental

  Jamie Caudill Lokation Real Estate

  701 Spanish Main Dr Unit 512, Cudjoe Key, FL 33042
• 

  

  /67

  $1,900,000 Sold Nov 06, 2025

  17077 Bonita Ln W, Summerland Key, FL 33042

  • 4 Beds
  • 4 Baths
  • 2,400 Sq Ft
  • Built 1990

  Last Sold Summary

  • 5% Below List Price
  • $792/SF
  • 87 Days On Market

  Current Estimated Value $1,869,864

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  17077 Bonita Ln W, Summerland Key, FL 33042
• 

  

  /23

  Est $808,211 Not Listed For Sale

  17213 Snapper Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,008 Sq Ft
  • Built 1988

  17213 Snapper Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 9% Above List Price
  • $734/SF
  • 7 Days On Market

  Last Sold Price $740,000

  Last Listing Agent Wendy Holifield Berkshire Hathaway HomeServices Knight & Gardner Realty
• 

  

  /13

  $395,000

  • Land

  24285 Caribbean Dr, Summerland Key, FL 33042

  Purchase this deep draft canal front LOT in Summerland Key while the building permit is in-process for a 4 bedroom / 2 bath stilted single family residence (home is additional). The plans shown are for a 1920 sq ft' / 2 story Affinity home with features that include impact doors and windows and built to 180 mph with a cistern and designed using the Green Building code. Great for the environment,

  Donna Pezzi Keller Williams Key West Compass Realty

  24285 Caribbean Dr, Summerland Key, FL 33042
• 

  

  /5

  $175,000 Sold Aug 21, 2025

  27313 Saint Martin Ln, Ramrod Key, FL 33042

  • Land

  Last Sold Summary

  • 12% Below List Price
  • 9 Days On Market

  Current Estimated Value $175,955

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  27313 Saint Martin Ln, Ramrod Key, FL 33042
• 

  

  /32

  Est $2,911,517 Not Listed For Sale

  176 Sugarloaf Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2.5 Baths
  • 2,976 Sq Ft
  • Built 2003

  176 Sugarloaf Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 3% Above List Price
  • $1,005/SF
  • 257 Days On Market

  Last Sold Price $2,990,000

  Last Listing Agent Key West Luxury Finders Preferred Properties (KW)
• 

  

  /7

  $190,000

  • Land
  • 6,000 Acres
  • $32 per Acre

  1145 Hakluyt Ln, Cudjoe Key, FL 33042

  Discover one of Cudjoe Key’s desirable vacant parcels — a 6,000 sq ft waterfront lot offering direct access to the Lower Keys’. Located on a quiet road, this property pairs privacy with easy access to local conveniences and the laid-back lifestyle of the Lower Keys. Enjoy morning coffee with ocean breezes, evening skies, and endless outdoor living possibilities.(Information provided herein is

  Daniel Pacheco United Realty Group Inc

  1145 Hakluyt Ln, Cudjoe Key, FL 33042
• 

  

  /114

  $1,477,000 Sold Sep 02, 2025

  153 Galleon Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft
  • Built 2018

  Last Sold Summary

  • 2% Below List Price
  • $947/SF
  • 49 Days On Market

  Current Estimated Value $1,452,952

  Last Listing Agent Lindsay Ryan EXP Realty LLC

  153 Galleon Ln, Summerland Key, FL 33042
• 

  

  /26

  Est $988,721 Not Listed For Sale

  19648 Caribe St, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 961 Sq Ft
  • Built 1957

  19648 Caribe St, Summerland Key, FL 33042

  Last Sold Summary

  • 8% Below List Price
  • $1,119/SF
  • 176 Days On Market

  Last Sold Price $1,075,000

  Last Listing Agent Rey Delgado Cohen & Roth, LLC
• 

  

  /116

  $19,750,000

  • 6 Beds
  • 7 Baths
  • 4,402 Sq Ft

  15760 Old State Road 4a, Summerland Key, FL 33042

  Rare Private Sandy Beach - Oceanfront Estate with endless open ocean views, just 30 minutes to Key West! This is a once-in-a-lifetime opportunity to own over 5 acres of sprawling oceanfrontage on exclusive Sugarloaf Beach, with over 500 feet of pristine sandy shoreline. Zoned Sub Urban Residential, this rare estate offers unmatched potential--create a private luxury compound, a boutique resort

  Lisa Swanson The Agency Florida Keys

  15760 Old State Road 4a, Summerland Key, FL 33042

Showing Results 561 - 600, Page 15 of 18