Summerland Key, FL Homes

• 

  

  /2

  Est $1,022,577

  Not Listed For Sale

  29552 Independence Ave, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,280 Sq Ft
  • Built 1976

  29552 Independence Ave, Big Pine Key, FL 33043
• 

  

  

  /20

  $1,295,000

  • 4 Beds
  • 2 Baths
  • 1,820 Sq Ft

  29678 Enterprise Ave, Big Pine Key, FL 33043

  Discover an outstanding opportunity in Big Pine Key with this canal-front, stilted duplex featuring two spacious 2 bedroom 1 bath residences and deep-water boating access. This is an exceptional boater's duplex in Pine Channel Estates where you can enjoy income and lifestyle in one place. Enjoy 75 feet of concrete dockage with a convenient step-down and retaining wall, all situated on a clean,

  Thomas Carden Keys to the Coast Real Estate LLC

  29678 Enterprise Ave, Big Pine Key, FL 33043
• 

  

  

  /73

  $2,650,000

  Sold Jul 10, 2026

  23941 Henry St, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 2,232 Sq Ft
  • Built 2002

  Last Sold Summary

  • 5% Below List Price
  • $1,187/SF
  • 32 Days On Market

  Current Estimated Value $2,797,197

  Last Listing Agent Stacy Shahan Island Real Estate Company Florida Keys

  23941 Henry St, Summerland Key, FL 33042
• 

  

  

  /42

  Est $1,163,357

  Not Listed For Sale

  31040 Atlantis Dr, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft
  • Built 1986

  31040 Atlantis Dr, Big Pine Key, FL 33043

  Last Sold Summary

  • 128 Days On Market
• 

  

  

  /42

  $1,049,000

  $26K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,116 Sq Ft

  27416 Cayman Ln, Ramrod Key, FL 33042

  Seller offering a buyer concession at closing--providing flexibility toward closing costs, an interest rate buy-down, prepaid expenses, or other allowable buyer costs. Now offered with this added value, this is an exceptional opportunity to own one of the Lower Keys' premier boating properties. Boater's dream waterfront on Ramrod Key with no-bridge ocean access, dual boat lifts, and open Atlantic

  Melissa Gibbins Expert Realty LLC (HQ)

  27416 Cayman Ln, Ramrod Key, FL 33042
• 

  

  /73

  $809,300

  Sold Aug 18, 2025

  547 Heck Ave, Little Torch Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,100 Sq Ft
  • Built 1991

  Last Sold Summary

  • $736/SF
  • 39 Days On Market

  Current Estimated Value $867,854

  Last Listing Agent Litney Ellis Dalton Wade Inc

  547 Heck Ave, Little Torch Key, FL 33042
• 

  

  /46

  Est $2,564,810

  Not Listed For Sale

  661 Sugarloaf Blvd, Summerland Key, FL 33042

  • 3 Beds
  • 4 Baths
  • 2,371 Sq Ft
  • Built 1967

  661 Sugarloaf Blvd, Summerland Key, FL 33042

  Last Sold Summary

  • 78 Days On Market
• 

  

  /6

  $175,000

  $50K PRICE DROP

  • Land
  • 0 Sq Ft

  29859 Overseas Hwy Unit A-3, Big Pine Key, FL 33043

  Transferable ROGO Exempt Building Right + 2,250 Sq Ft Lot - Build Immediately! Rare opportunity to own a ROGO-exempt parcel in the Florida Keys, allowing you to build right away with no waiting period. This property allows flexibility--use the building right on-site, transfer it to another parcel, or sell it separately, as it is fully transferable. Bring your vision to life and build your dream

  Steven Koleno Beycome of Florida, LLC

  29859 Overseas Hwy Unit A-3, Big Pine Key, FL 33043
• 

  

  /41

  $2,280,000

  Sold Apr 02, 2026

  1176 Thatch Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,577 Sq Ft
  • Built 1984

  Last Sold Summary

  • 24% Below List Price
  • $1,446/SF
  • 359 Days On Market

  Current Estimated Value $2,323,186

  Last Listing Agent Jonathan Minerick Homecoin.com

  1176 Thatch Ln, Summerland Key, FL 33042
• 

  /2

  Est $1,064,197

  Not Listed For Sale

  467 Almond Ln, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,390 Sq Ft
  • Built 1995

  467 Almond Ln, Big Pine Key, FL 33043
• 

  

  /51

  $1,725,000

  $174K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,440 Sq Ft

  22542 Jolly Roger Dr, Summerland Key, FL 33042

  Stunning oceanfront home. This 4-bedroom, 3-bathroom home is a testament to coastal architecture. Broad, covered balconies, generous outdoor spaces, and a private boat launch capitalize on Keys waterfront living. Large impact glass doors and windows frame ocean views and invite natural light into every room. Soaring, 26' ceilings enhance the open-concept layout with rich wood beams amplifying the

  Lauren Dunn Coldwell Banker Schmitt Islamorada

  22542 Jolly Roger Dr, Summerland Key, FL 33042
• 

  

  /18

  $250,000

  Sold Feb 24, 2026

  138 Sands Rd, Big Pine Key, FL 33043

  • 1 Bed
  • 1 Bath
  • 442 Sq Ft
  • Built 1969

  Last Sold Summary

  • 9% Below List Price
  • $566/SF
  • 16 Days On Market

  Last Listing Agent Kate Zhang Kylin Realty LLC

  138 Sands Rd, Big Pine Key, FL 33043
• 

  

  /44

  Est $678,809

  Not Listed For Sale

  29135 Camellia Ln, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,238 Sq Ft
  • Built 1988

  29135 Camellia Ln, Big Pine Key, FL 33043

  Last Sold Summary

  • 3 Days On Market
• 

  

  /3

  $60,000

  • Land
  • 5,000 Sq Ft
  • $522,720 per Acre

  Lot 10 Rainbow Beach, Big Torch Key, FL 33042

  Tier 1 lot available for ROGO Donation use only. This property cannot be built on and no RV use is permitted. The sale includes a ROGO Dedication Letter valued at 2 points, providing a valuable advantage in the Monroe County permit allocation system.

  Shanti Cope Coldwell Banker Schmitt Key Largo

  Lot 10 Rainbow Beach, Big Torch Key, FL 33042
• 

  

  /41

  $1,350,000

  Sold Aug 18, 2025

  20735 5th Ave W, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,582 Sq Ft
  • Built 1985

  Last Sold Summary

  • 7% Below List Price
  • $853/SF
  • 16 Days On Market

  Current Estimated Value $1,387,022

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  20735 5th Ave W, Summerland Key, FL 33042
• 

  

  /46

  Est $1,290,489

  Not Listed For Sale

  137 Caribbean Dr E, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 1986

  137 Caribbean Dr E, Summerland Key, FL 33042

  Last Sold Summary

  • 8 Days On Market
• 

  

  /37

  $650,000

  • 2 Beds
  • 2 Baths
  • 1,092 Sq Ft

  27732 Astrangia Ave, Little Torch Key, FL 33042

  Welcome to your own slice of the Florida Keys paradise. This beautifully remodeled and fully furnished 2-bedroom, 2-bath waterfront home is the definition of move-in ready--offered turnkey and decorated in charming coastal colors and beach-inspired décor that perfectly captures the relaxed island lifestyle. Ideally positioned just three homes from open water, this canal-front retreat offers

  Monika Rydzak eXp Realty LLC KW Branch

  27732 Astrangia Ave, Little Torch Key, FL 33042
• 

  

  /37

  $725,000

  Sold Jan 14, 2026

  27394 Saint Lucie Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,078 Sq Ft
  • Built 1994

  Last Sold Summary

  • $673/SF
  • 19 Days On Market

  Current Estimated Value $760,732

  Last Listing Agent Casey Arnold eXp Realty LLC

  27394 Saint Lucie Ln, Summerland Key, FL 33042
• 

  /2

  Est $939,323

  Not Listed For Sale

  22842 Buccaneer Ln, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 1,326 Sq Ft
  • Built 1998

  22842 Buccaneer Ln, Summerland Key, FL 33042
• 

  

  /74

  $2,895,000

  $355K PRICE DROP Under Contract

  • 4 Beds
  • 4 Baths
  • 1,804 Sq Ft

  17385 Keystone Rd, Summerland Key, FL 33042

  Stunning open water views from this fabulous waterfront home! A truly rare and highly coveted 37,139 sqft lot point lot with A massive 362 FT OF WATERFRONTAGE on prestigious Sugarloaf Key, offering breathtaking panoramic open water views, exceptional privacy, and unmatched boating access. (24,662 sqft Upland & 12,477 submerged). These point lots are extremely limited and among the most

  Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty

  17385 Keystone Rd, Summerland Key, FL 33042
• 

  

  /47

  $945,000

  Sold Oct 03, 2025

  29487 Ranger Ave, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,258 Sq Ft
  • Built 1996

  Last Sold Summary

  • 3% Below List Price
  • $751/SF
  • 99 Days On Market

  Current Estimated Value $1,019,986

  Last Listing Agent Melissa Gibbins Expert Realty LLC (HQ)

  29487 Ranger Ave, Big Pine Key, FL 33043
• 

  

  /23

  Est $1,367,932

  Not Listed For Sale

  30891 Granada Ave, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,568 Sq Ft
  • Built 1987

  30891 Granada Ave, Big Pine Key, FL 33043

  Last Sold Summary

  • 73 Days On Market
• 

  

  /5

  $599,000

  • Land
  • 6,098 Sq Ft
  • $4,278,571 per Acre

  27374 Guadaloupe Ln, Summerland Key, FL 33042

  *OWNER FINANCING CONSIDERED* and dock included in purchase! Golden opportunity in the Lower Keys with rare permitting advantages already in place. This waterfront lot is ready for your new Keys home, with an active permit for a 3 bedroom, 3 bath residence and a dock permit for a 40-foot dock. In unincorporated Monroe County, where residential construction is controlled by the highly competitive

  Nick Boumerhi Meyer and Boumerhi Realty LLC

  27374 Guadaloupe Ln, Summerland Key, FL 33042
• 

  

  /49

  $750,000

  Sold Jul 24, 2025

  25121 Center St, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft
  • Built 2008

  Last Sold Summary

  • 14% Below List Price
  • $781/SF
  • 72 Days On Market

  Current Estimated Value $773,465

  Last Listing Agent Gregory Sullivan BYOWNER.COM

  25121 Center St, Summerland Key, FL 33042
• 

  

  /115

  Est $7,033,207

  Not Listed For Sale

  785 Sawyer Dr, Cudjoe Key, FL 33042

  • 7 Beds
  • 6 Baths
  • 4,888 Sq Ft
  • Built 2019

  785 Sawyer Dr, Cudjoe Key, FL 33042

  Last Sold Summary

  • 44 Days On Market
• 

  

  /78

  $1,490,000

  New Construction $110K PRICE DROP Under Contract

  • 4 Beds
  • 3 Baths
  • 2,136 Sq Ft

  142 Peg Leg Ln, Cudjoe Key, FL 33042

  Welcome to your dream coastal retreat! This newer 4-bedroom, 3-bath luxury home offers the perfect blend of island elegance and modern comfort. Two spacious master suites provide privacy and flexibility, while the open-concept living space is framed by wide, breezy balconies, ideal for soaking in the sunrise or entertaining guests in true Keys style. Canal with direct access to the open ocean. No

  NON-MLS MEMBER MAR NON MLS MEMBER

  142 Peg Leg Ln, Cudjoe Key, FL 33042
• 

  

  /62

  $720,000

  Sold May 18, 2026

  28151 Helen Ave, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,410 Sq Ft
  • Built 2021

  Last Sold Summary

  • 6% Below List Price
  • $511/SF
  • 51 Days On Market

  Current Estimated Value $738,252

  Last Listing Agent Lindsay Ryan EXP Realty LLC

  28151 Helen Ave, Summerland Key, FL 33042
• 

  

  /27

  Est $756,620

  Not Listed For Sale

  1537 Pandorea Ln, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft
  • Built 1973

  1537 Pandorea Ln, Big Pine Key, FL 33043

  Last Sold Summary

  • 3 Days On Market
• 

  

  /112

  $2,700,000

  New Construction $100K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,100 Sq Ft

  1553 Sunrise Dr, Big Pine Key, FL 33043

  Walk into this luxurious palace with captivating open water views. Light colors accenting the beautiful interior with matching large porcelain floors enhancing the large windows bringing the natural light inside. Gourmet kitchen for any chef to create great memories viewing the sunsets. Open patio with a great view of the pool and the outdoor entertaining areas. Three roomy suites for your family

  Barbara Eads Barbara Eads Realty

  1553 Sunrise Dr, Big Pine Key, FL 33043
• 

  

  /29

  $720,000

  Sold Apr 17, 2026

  630 Barry Ave, Little Torch Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,062 Sq Ft
  • Built 2005

  Last Sold Summary

  • 28% Below List Price
  • $678/SF
  • 86 Days On Market

  Current Estimated Value $887,114

  Last Listing Agent Brenda Thomas Island Welcome Real Estate

  630 Barry Ave, Little Torch Key, FL 33042
• 

  

  /31

  Est $730,432

  Not Listed For Sale

  174 Newfound Blvd, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft
  • Built 1987

  174 Newfound Blvd, Big Pine Key, FL 33043

  Last Sold Summary

  • 3 Days On Market
• 

  

  /51

  $825,000

  Open Sun 10AM - 12PM $13K PRICE DROP

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

  29115 Rose Dr, Big Pine Key, FL 33043

  Back on the market! Welcome to this meticulously maintained and updated move-in ready canal-front home that offers the perfect blend of comfort, style, and durability. Featuring an inviting open-concept floor plan, this home boasts three spacious bedrooms and two modern bathrooms, all enhanced by LVP flooring throughout. Built above flood level with just the right number of steps to climb, this

  Dave Wiley Coldwell Banker Schmitt Real Estate Co. (KW)

  29115 Rose Dr, Big Pine Key, FL 33043
• 

  

  /45

  $710,000

  Sold Feb 05, 2026

  27163 Mariposa Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,488 Sq Ft
  • Built 2018

  Last Sold Summary

  • 10% Below List Price
  • $477/SF
  • 238 Days On Market

  Current Estimated Value $742,790

  Last Listing Agent Jessica Roden Ocean Sotheby's International Realty

  27163 Mariposa Rd, Summerland Key, FL 33042
• 

  

  /42

  Est $1,047,129

  Not Listed For Sale

  27330 Barbados Ln, Ramrod Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,764 Sq Ft
  • Built 1991

  27330 Barbados Ln, Ramrod Key, FL 33042

  Last Sold Summary

  • 79 Days On Market
• 

  

  /22

  $949,000

  Open Sun 11AM - 1PM $101K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,418 Sq Ft

  1540 Lantana Ln, Big Pine Key, FL 33043

  Bring your boats to this beautifully furnished canal front home. TURN KEY READY! Secluded on a corner large lot with 190 ft. of concrete dockage. Large and open living, dining, and kitchen areas. Lovely, updated kitchen and baths. New beautiful floors, along with impact windows, doors and metal roof. Enjoy swimming in the above ground pool, relaxing on the deck, cocktails at the outside bar, or

  Andrea Lennon Vylla Home

  1540 Lantana Ln, Big Pine Key, FL 33043
• 

  

  /100

  $3,300,000

  Sold Dec 01, 2025

  815 E Shore Dr, Summerland Key, FL 33042

  • 7 Beds
  • 6 Baths
  • 4,531 Sq Ft
  • Built 1961

  Last Sold Summary

  • 26% Below List Price
  • $728/SF
  • 295 Days On Market

  Current Estimated Value $4,119,742

  Last Listing Agent Karen Williams-deCastro LPT Realty, LLC

  815 E Shore Dr, Summerland Key, FL 33042
• 

  

  /64

  Est $1,694,468

  Not Listed For Sale

  553 Indies Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,801 Sq Ft
  • Built 1996

  553 Indies Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 76 Days On Market
• 

  

  /9

  $399,000

  • 2 Beds
  • 2 Baths
  • 1,344 Sq Ft

  27917 Coral Shores Rd, Summerland Key, FL 33042

  Located on a clean boating canal in Coral Shores Subdivision. This property is waiting for someone to tear it down and put up their brand-new home. With a full 46 foot seawall and a 5-minute boat ride to open water this is a boater's dream. The wooded lots across the street offer both privacy and beautiful wildlife where you can enjoy the peaceful sound of the many different types of birds. There

  Tara Thoman-Wood,P.A. Berkshire Hathaway HomeServices Knight & Gardner Realty

  27917 Coral Shores Rd, Summerland Key, FL 33042
• 

  

  /32

  $450,000

  Sold Aug 20, 2025

  701 Spanish Main Dr Unit 22, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 814 Sq Ft
  • Built 2016

  Last Sold Summary

  • 9% Below List Price
  • $553/SF
  • 283 Days On Market

  Last Listing Agent Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 22, Cudjoe Key, FL 33042
• 

  

  /62

  Est $5,194,680

  Not Listed For Sale

  1141 Ocean Dr, Summerland Key, FL 33042

  • 5 Beds
  • 4.5 Baths
  • 3,421 Sq Ft
  • Built 2005

  1141 Ocean Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 22 Days On Market

Showing Results 401 - 440, Page 11 of 18