Homes in ZIP Code 33042

• 

  

  

  /4

  $100,000

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

  0 Acosta Rd, Summerland 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. Svc.

  0 Acosta Rd, Summerland Key, FL 33042
• 

  

  

  /47

  $935,000 Sold Dec 31, 2025

  786 Jamaica Ln, Little Torch Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft
  • Built 2016

  Last Sold Summary

  • 5% Below List Price
  • $649/SF
  • 89 Days On Market

  Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

  786 Jamaica Ln, Little Torch Key, FL 33042
• 

  

  

  /36

  Est $1,660,567 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,018 Sq Ft

  919 Bay Dr, Summerland Key, FL 33042

  919 Bay Dr, Summerland Key, FL 33042
• 

  

  

  /7

  $4,150,000 Open Sun 10AM - 1PM

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

  231 E Shore Dr Unit 2, 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 2, Summerland Key, FL 33042
• 

  

  

  /21

  $1,000,000 Sold Aug 29, 2025

  419 Blackbeard Rd, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,050 Sq Ft
  • Built 1988

  Last Sold Summary

  • 17% Below List Price
  • $952/SF
  • 250 Days On Market

  Current Estimated Value $991,809

  Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

  419 Blackbeard Rd, Summerland Key, FL 33042
• 

  

  /53

  Est $1,204,929 Not Listed For Sale

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

  845 Gulf Dr, Summerland Key, FL 33042

  845 Gulf Dr, Summerland Key, FL 33042
• 

  

  /15

  $285,000 Pending

  • Land

  27345 Guadaloupe Ln, Ramrod Key, FL 33042

  Discover an exceptional canal-front lot that boasts direct bridge-free boating access, making it a fisherman's paradise and an ideal spot for your dream home. Nestled conveniently close to US 1 between Key West and Marathon, this location offers easy access to an array of restaurants, shopping, and mini golf--everything you need for the perfect Keys lifestyle. This Tier III lot is currently in

  Scott Brisson KeyIsle Realty

  27345 Guadaloupe Ln, Ramrod Key, FL 33042
• 

  

  /27

  $905,000 Sold Dec 11, 2025

  22852 John Silver Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,620 Sq Ft
  • Built 1980

  Last Sold Summary

  • 5% Below List Price
  • $559/SF
  • 75 Days On Market

  Last Listing Agent Matthew Sheehan Ocean Sotheby's International Realty

  22852 John Silver Ln, Summerland Key, FL 33042
• 

  

  /29

  Est $1,095,553 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,040 Sq Ft

  23034 Wahoo Ln, Summerland Key, FL 33042

  23034 Wahoo Ln, Summerland Key, FL 33042
• 

  

  /17

  $715,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,380 Sq Ft

  56 W Shore Dr, Summerland Key, FL 33042

  Rare waterfront opportunity in Summerland Key Cove! This 3-bedroom, 2-bath home offers 1,380 sq ft of living area on an oversized 7,000+ sq ft lot with direct access to world-class boating and fishing. Located on a deep, wide ocean-side canal, the property provides a quick ride out to open water -- perfect for enjoying the Lower Keys lifestyle.Summerland Key Cove is a highly desirable,

  Veronica Crego-Flores

  56 W Shore Dr, Summerland Key, FL 33042
• 

  

  /61

  $1,636,000 Sold Aug 19, 2025

  227 La Fitte Rd, Summerland Key, FL 33042

  • 2 Beds
  • 3 Baths
  • 1,260 Sq Ft
  • Built 1982

  Last Sold Summary

  • 9% Below List Price
  • $1,298/SF
  • 6 Days On Market

  Current Estimated Value $1,654,552

  Last Listing Agent Jennifer Chaney Chaney Homes

  227 La Fitte Rd, Summerland Key, FL 33042
• 

  

  /32

  Est $862,091 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 912 Sq Ft

  519 Pirates Rd, Summerland Key, FL 33042

  519 Pirates Rd, Summerland Key, FL 33042
• 

  

  /8

  $895,000 Under Contract

  • 1 Bed
  • 4 Baths
  • 1,965 Sq Ft

  24931 Overseas Hwy, Summerland Key, FL 33042

  Seize this rare opportunity to own a prime working waterfront property with exceptional Highway visibility. This unique offering includes two waterfront buildings located at 24931 & 24933 Overseas Highway in Summerland Key, each with separate water, electric, and sewer connections for added flexibility. Situated on a 10,673 SF lot, the property features a 813 SF building, a 1,152 SF building, and

  Claude Gardner Berkshire Hathaway HomeServices Knight & Gardner Realty

  24931 Overseas Hwy, Summerland Key, FL 33042
• 

  

  /39

  $1,116,000 Sold Jun 25, 2025

  591 Blackbeard Rd, Summerland Key, FL 33042

  • 4 Beds
  • 5 Baths
  • 2,512 Sq Ft
  • Built 1989

  Last Sold Summary

  • 17% Below List Price
  • $444/SF
  • 25 Days On Market

  Current Estimated Value $1,209,924

  Last Listing Agent Michelle Howerton Brenda Donnelly Real Estate LLC

  591 Blackbeard Rd, Summerland Key, FL 33042
• 

  

  /37

  Est $1,226,136 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,474 Sq Ft

  321 W Indies Dr, Summerland Key, FL 33042

  321 W Indies Dr, Summerland Key, FL 33042
• 

  

  /50

  $1,299,000 Pending

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

  19749 Date Palm Dr, Summerland Key, FL 33042

  An incredible opportunity, especially for those looking for a spacious, 2464 sq ft well-equipped 12-foot stilted custom-built, waterfront home. 4 bedrooms, 3 baths plus a den with recent improvements and updates. Enormous Master bedroom and master bath with a gigantic tub. A huge breathtaking kitchen with stainless steel appliances. The combination of a large living area, open floor plan, modern

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

  19749 Date Palm Dr, Summerland Key, FL 33042
• 

  

  /46

  $1,900,000 Sold Mar 27, 2025

  271 W Indies Dr, Ramrod Key, FL 33042

  • 4 Beds
  • 4 Baths
  • 2,358 Sq Ft
  • Built 2023

  Last Sold Summary

  • 36% Below List Price
  • $806/SF
  • 342 Days On Market

  Current Estimated Value $1,914,073

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

  271 W Indies Dr, Ramrod Key, FL 33042
• 

  

  /39

  Est $1,407,942 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,732 Sq Ft

  21076 3rd Ave, Summerland Key, FL 33042

  21076 3rd Ave, Summerland Key, FL 33042
• 

  

  /20

  $975,000

  • 3 Beds
  • 2 Baths
  • 1,565 Sq Ft

  24840 Park Dr, Summerland Key, FL 33042

  Hard to find a home in a Park like setting with a boat ramp right out the back door! 3 bedrooms 2 full baths and open living space. Summerland key cove is just 25 miles from Key West. Great place to raise a family or to retire. Be it you're a boater, pilot, fisherman or just want the open space to walk and enjoy privacy of the park. This quit Island neighborhood offers rare access to the

  Thomas Murphy LAER Realty

  24840 Park Dr, Summerland Key, FL 33042
• 

  /2

  $49,000 Sold Sep 22, 2025

  Lot 23 Rainbow Beach, Big Torch Key, FL 33042

  • Land

  Last Sold Summary

  • 21 Days On Market

  Last Listing Agent Pamela Stangler Expert Realty LLC

  Lot 23 Rainbow Beach, Big Torch Key, FL 33042
• 

  

  /43

  Est $2,273,518 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 2,935 Sq Ft

  340 S Point Dr, Summerland Key, FL 33042

  340 S Point Dr, Summerland Key, FL 33042
• 

  

  /7

  $4,400,000 Open Sat 11AM - 3PM

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

  231 E Shore Dr Unit 5, 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 5, Summerland Key, FL 33042
• 

  

  /40

  $825,000 Sold Aug 04, 2025

  260 Airport Dr S, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 918 Sq Ft
  • Built 1959

  Last Sold Summary

  • 8% Below List Price
  • $899/SF
  • 157 Days On Market

  Current Estimated Value $827,625

  Last Listing Agent Francesca Santiago Keller Williams Realty Professionals (KW)

  260 Airport Dr S, Summerland Key, FL 33042
• 

  

  /72

  Est $762,309 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,106 Sq Ft

  25083 Palm Ln, Summerland Key, FL 33042

  25083 Palm Ln, Summerland Key, FL 33042
• 

  

  /56

  $579,900

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  701 Spanish Main Dr Unit 437, Cudjoe Key, FL 33042

  Introducing an exceptional waterfront investment opportunity in the heart of the Florida Keys! This beautifully remodeled waterfront home in the highly desirable gated community of Venture Out on Cudjoe Key is zoned for minimum one-day vacation rentals, making it an ideal choice for investors or those seeking a turnkey coastal retreat. Step inside and you'll immediately appreciate the home's

  Melissa Graham Bluescape Real Estate

  701 Spanish Main Dr Unit 437, Cudjoe Key, FL 33042
• 

  

  /74

  $3,300,000 Sold Feb 18, 2025

  22572 Jolly Roger Dr, Summerland Key, FL 33042

  • 6 Beds
  • 4 Baths
  • 3,225 Sq Ft
  • Built 1963

  Last Sold Summary

  • 27% Below List Price
  • $1,023/SF
  • 313 Days On Market

  Current Estimated Value $3,225,004

  Last Listing Agent Jan Fritz Coldwell Banker Schmitt RE Co.

  22572 Jolly Roger Dr, Summerland Key, FL 33042
• 

  /2

  Est $824,480 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  22968 Drake Ln, Summerland Key, FL 33042

  22968 Drake Ln, Summerland Key, FL 33042
• 

  

  /9

  $2,400,000

  • Land
  • 0.55 Acre
  • $4,356,000 per Acre

  24356 Overseas Hwy, Summerland Key, FL 33042

  Begin your Florida Keys venture at this exceptional waterfront Commercial property. The site consists of four lots measuring 60'x100' each, creating a 24,000-square-foot parcel with 240 feet of concrete seawall. The property comes equipped with water and electrical connections. Its strategic location offers excellent access to both the Atlantic and Gulf waters, including proximity to Looe Key

  Scott Brisson KeyIsle Realty

  24356 Overseas Hwy, Summerland Key, FL 33042
• 

  

  /44

  $650,000 Sold Apr 17, 2025

  268 Spanish Main Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1979

  Last Sold Summary

  • 7% Below List Price
  • $616/SF
  • 86 Days On Market

  Current Estimated Value $670,224

  Last Listing Agent Ally Kelley Ocean Sotheby's International

  268 Spanish Main Dr, Summerland Key, FL 33042
• 

  /2

  Est $1,479,663 Not Listed For Sale

  • 2 Beds
  • 3 Baths
  • 960 Sq Ft

  195 La Fitte Rd, Summerland Key, FL 33042

  195 La Fitte Rd, Summerland Key, FL 33042
• 

  

  /39

  $625,000

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  701 Spanish Main Dr Unit 495, Cudjoe Key, FL 33042

  Welcome to this completely remodeled, direct canal front cottage located at 701 Spanish Main Dr in Cudjoe Key, FL. This beautiful property offers 2 bedrooms and 2 bathrooms within its 816 sq.ft. of finished living space. The home sits on a 2,568 sq.ft. lot, providing ample outdoor space for relaxing and entertaining. The property features a bright and airy interior with an open floor plan,

  Randal Longo Keys Realty Redefined LLC

  701 Spanish Main Dr Unit 495, Cudjoe Key, FL 33042
• 

  

  /41

  $2,425,000 Sold Nov 21, 2025

  281 W Indies Dr, Summerland Key, FL 33042

  • 3 Beds
  • 4 Baths
  • 2,914 Sq Ft
  • Built 2020

  Last Sold Summary

  • 12% Below List Price
  • $832/SF
  • 203 Days On Market

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

  281 W Indies Dr, Summerland Key, FL 33042
• 

  

  /30

  Est $1,667,547 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,570 Sq Ft

  540 W Point Dr, Summerland Key, FL 33042

  540 W Point Dr, Summerland Key, FL 33042
• 

  

  /83

  $4,400,000

  • 4 Beds
  • 4.5 Baths
  • 2,907 Sq Ft

  16745 Tamarind Rd, Sugarloaf Shores, FL 33042

  Step into your own waterfront sanctuary, 'Casa Del Mar' in prestigious Sugarloaf Shores on Lower Sugarloaf Key, where clean, modern design meets unmistakable Florida Keys ease. This beautifully built CBS home with impact windows delivers 4 spacious bedrooms and 4.5 baths, wrapped in contemporary style and coastal charm.Inside, the heart of the home is a true chef's kitchen with high-end

  Carlos Lorenzo American Caribbean Real Estate, Christie's International Real Estate

  16745 Tamarind Rd, Sugarloaf Shores, FL 33042
• 

  

  /82

  $1,800,000 Sold Jun 20, 2025

  17175 Allamanda Dr W, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,116 Sq Ft
  • Built 1999

  Last Sold Summary

  • 5% Below List Price
  • $851/SF
  • 19 Days On Market

  Current Estimated Value $1,800,842

  Last Listing Agent Lisa Swanson The Agency Florida Keys

  17175 Allamanda Dr W, Summerland Key, FL 33042
• 

  

  /28

  Est $965,549 Not Listed For Sale

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

  340 Spanish Main Dr, Summerland Key, FL 33042

  340 Spanish Main Dr, Summerland Key, FL 33042
• 

  

  /5

  $240,000

  • 2 Beds
  • 1 Bath
  • 672 Sq Ft

  28177 Julia Ave, Little Torch Key, FL 33042

  Opportunity to purchase for land value in Little Torch Key. Large lot with existing mobile home on site that is not habitable. Property is being marketed as land only. Lot is zoned IS (Improved Subdivision District), which typically allows for single-family residential construction subject to Monroe County Land Development Code and applicable ROGO requirements. Conveniently located less than 5

  Maria Acosta Keller Williams Capital Realty - Coral Gables

  28177 Julia Ave, Little Torch Key, FL 33042
• 

  

  /33

  $725,000 Sold Feb 21, 2025

  22918 Cudjoe Dr, Cudjoe Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,431 Sq Ft
  • Built 2016

  Last Sold Summary

  • 9% Below List Price
  • $507/SF
  • 175 Days On Market

  Current Estimated Value $772,347

  Last Listing Agent Pamela Stangler Expert Realty LLC

  22918 Cudjoe Dr, Cudjoe Key, FL 33042
• 

  

  /36

  Est $1,528,669 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,550 Sq Ft

  20878 5th Ave W, Summerland Key, FL 33042

  20878 5th Ave W, Summerland Key, FL 33042
• 

  

  /52

  $1,049,000 Under Contract

  • 2 Beds
  • 2 Baths
  • 1,040 Sq Ft

  27360 Barbados Ln, Summerland Key, FL 33042

  Welcome to your Florida Keys oasis on an oversized 90' x 100' lot w/ 60ft dock--offering space, privacy, and upgrades rarely found in the Lower Keys. Meticulously maintained and lovingly cared for, this waterfront home features vaulted ceilings, a wraparound porch, and panoramic sliding doors that create exceptional indoor/outdoor flow, allowing the home to live much larger than its under-air

  Brian Kruszewski LoKation Real Estate

  27360 Barbados Ln, Summerland Key, FL 33042

Showing Results 641 - 680, Page 17 of 18