Summerland Key, FL Homes

• 

  

  

  /38

  $1,099,999

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,320 Sq Ft

  335 Pirates Rd, Summerland Key, FL 33042

  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 for those who enjoy fishing, cruising, or

  Nick Boumerhi Meyer and Boumerhi Realty LLC

  335 Pirates Rd, Summerland Key, FL 33042
• 

  

  

  /31

  $799,000

  Sold May 29, 2026

  31226 Hollerich Dr, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,040 Sq Ft
  • Built 1980

  Last Sold Summary

  • $768/SF
  • 11 Days On Market

  Current Estimated Value $793,962

  Last Listing Agent Wyatt Tucker Expert Realty LLC (HQ)

  31226 Hollerich Dr, Big Pine Key, FL 33043
• 

  

  

  /27

  Est $750,144

  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

  Last Listing Agent Deni Heintzelman KeyIsle Realty
• 

  

  

  /40

  $894,000

  $31K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,034 Sq Ft

  28571 Buccaneer Rd, Summerland Key, FL 33042

  Experience the best of the Florida Keys lifestyle in this inviting 3-bedroom, 2-bath waterfront home with quick ocean access and no bridges. Boating enthusiasts will appreciate the 30-foot concrete dock with davits, providing an ideal launching point for fishing, diving, and days on the water.Designed for easy island living, the home features durable Hardie board siding, a metal roof, and a

  Diane Corliss Coldwell Banker Schmitt RE Co.

  28571 Buccaneer Rd, Summerland Key, FL 33042
• 

  

  

  /96

  $1,575,000

  Sold Mar 23, 2026

  17176 Bonita Ln W, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,353 Sq Ft
  • Built 1974

  Last Sold Summary

  • 7% Below List Price
  • $669/SF
  • 63 Days On Market

  Current Estimated Value $1,637,457

  Last Listing Agent Tom Mclaughlin Coldwell Banker Schmitt Real Estate Co. (KW)

  17176 Bonita Ln W, Summerland Key, FL 33042
• 

  

  /31

  Est $745,646

  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

  Last Listing Agent Lindsay Ryan Island Breeze Realty, LLC
• 

  

  /43

  $849,000

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,372 Sq Ft

  281 Pelican Ln, Big Pine Key, FL 33043

  Situated on an oversized corner lot at the end of a quiet street, this brand-new home is ready to welcome its first owner. Thoughtfully built with durability, quality, and modern design in mind, 281 Pelican Lane offers the perfect blend of contemporary comfort and the relaxed lifestyle of the Florida Keys. Featuring 3 bedrooms and 2 bathrooms, the home is well suited as a full-time residence,

  Justyn Ewald Expert Realty LLC

  281 Pelican Ln, Big Pine Key, FL 33043
• 

  

  /40

  $1,050,000

  Sold Jan 12, 2026

  32734 Bimini Ln, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,654 Sq Ft
  • Built 1995

  Last Sold Summary

  • 14% Below List Price
  • $635/SF
  • 235 Days On Market

  Current Estimated Value $1,102,876

  Last Listing Agent Ally Kelley Ocean Sotheby's International

  32734 Bimini Ln, Big Pine Key, FL 33043
• 

  

  /64

  Est $1,670,267

  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

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

  

  /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
• 

  

  /30

  $440,000

  Sold Apr 30, 2026

  701 Spanish Main Dr Unit 234, Cudjoe Key, FL 33042

  • 2 Beds
  • 1.5 Baths
  • 604 Sq Ft
  • Built 1976

  Last Sold Summary

  • 9% Below List Price
  • $728/SF
  • 170 Days On Market

  Last Listing Agent Jenifer Hirsch Bluescape Real Estate

  701 Spanish Main Dr Unit 234, Cudjoe Key, FL 33042
• 

  

  /62

  Est $5,064,019

  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

  Last Listing Agent Lisa Swanson Berkshire Hathaway HomeServices Knight & Gardner Realty
• 

  

  /42

  $1,024,000

  $51K PRICE DROP

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

  27416 Cayman Ln, Ramrod Key, FL 33042

  Boater's dream waterfront on Ramrod Key with no-bridge ocean access, dual boat lifts, and open Atlantic access in minutes. Offered fully furnished and turnkey, this is Keys living at its best.Welcome to Breezeswept Dockside Retreat, designed for those who want to spend more time on the water. Situated on a 40' wide canal with approximately 3' control depth, you'll enjoy quick access to

  Melissa Gibbins Expert Realty LLC (HQ)

  27416 Cayman Ln, Ramrod Key, FL 33042
• 

  /2

  $1,400,000

  Sold Sep 17, 2025

  491 W Indies Dr, Ramrod Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,204 Sq Ft
  • Built 2020

  Last Sold Summary

  • $1,163/SF
  • 0 Days On Market

  Current Estimated Value $1,432,141

  Last Listing Agent Mark Gable Engel & Völkers Marathon

  491 W Indies Dr, Ramrod Key, FL 33042
• 

  

  /40

  Est $2,271,753

  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

  • 6 Days On Market

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

  

  /6

  $165,000

  $60K 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
• 

  

  /10

  $100,000

  Sold Apr 17, 2026

  BK 24 LT 2 Pandorea Ln, Big Pine Key, FL 33043

  • Land
  • 8,276 Sq Ft
  • $526,316 per Acre

  Last Sold Summary

  • 8 Days On Market

  Last Listing Agent Vanessa J. Chamizo, Professional Agent Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

  BK 24 LT 2 Pandorea Ln, Big Pine Key, FL 33043
• 

  

  /80

  Est $6,911,383

  Not Listed For Sale

  17279 Oleander Ln, Sugarloaf Key, FL 33042

  • 10 Beds
  • 11.5 Baths
  • 10,607 Sq Ft
  • Built 1958

  17279 Oleander Ln, Sugarloaf Key, FL 33042

  Last Sold Summary

  • 36 Days On Market

  Last Listing Agent NON-MLS MEMBER MAR NON MLS MEMBER
• 

  

  /52

  $1,725,000

  $174K PRICE DROP

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

  22542 Jolly Roger Dr, Summerland Key, FL 33042

  Oceanfront living on Cudjoe Key, where broad covered balconies, generous outdoor space, and a private boat launch put Keys waterfront life within reach. This four-bedroom, three-bath home is a study in coastal architecture -- large impact glass doors and windows frame open water views and pull natural light into every room. Soaring 26' ceilings and rich wood beams anchor the open-concept main

  Lauren Dunn Coldwell Banker Schmitt Islamorada

  22542 Jolly Roger Dr, Summerland Key, FL 33042
• 

  

  /9

  $175,000

  Sold Apr 06, 2026

  Vacant Picard Ln, Cudjoe Key, FL 33042

  • Land
  • 6,000 Sq Ft
  • $1,270,500 per Acre

  Last Sold Summary

  • 12% Below List Price
  • 219 Days On Market

  Last Listing Agent Lee Sanders/Sunnie SanLorenzo KeyIsle Realty

  Vacant Picard Ln, Cudjoe Key, FL 33042
• 

  

  /30

  Est $1,002,584

  Not Listed For Sale

  31625 Warner St, Big Pine Key, FL 33043

  • 1 Bed
  • 1 Bath
  • 650 Sq Ft
  • Built 1937

  31625 Warner St, Big Pine Key, FL 33043

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Shane Wilson Cypress Realty, Inc.
• 

  

  /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
• 

  

  /46

  $860,000

  Sold Aug 11, 2026

  288 Spanish Main Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,144 Sq Ft
  • Built 1984

  Last Sold Summary

  • 18% Below List Price
  • $752/SF
  • 108 Days On Market

  Current Estimated Value $926,039

  Last Listing Agent Richard Haskins Buy The Keys

  288 Spanish Main Dr, Summerland Key, FL 33042
• 

  

  /57

  Est $1,459,721

  Not Listed For Sale

  468 Sawyer Dr, Summerland Key, FL 33042

  • 4 Beds
  • 4 Baths
  • 1,797 Sq Ft
  • Built 1972

  468 Sawyer Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 215 Days On Market

  Last Listing Agent Stacy Shahan Island Real Estate Company Florida Keys
• 

  

  /37

  $650,000

  Under Contract

  • 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
• 

  

  /30

  $430,000

  Sold May 11, 2026

  21857 Disturbed Pine Rd, Summerland Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 415 Sq Ft
  • Built 1975

  Last Sold Summary

  • $1,036/SF
  • 94 Days On Market

  Current Estimated Value $454,125

  Last Listing Agent Rose Dell Keller Williams Key West Compass Realty

  21857 Disturbed Pine Rd, Summerland Key, FL 33042
• 

  

  /40

  Est $988,679

  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

  • 11 Days On Market

  Last Listing Agent Heather Mason Coastal Collection Real Estate Inc.
• 

  

  /66

  $1,450,000

  New Construction $49K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,000 Sq Ft

  2211 San Sebastian Dr, Big Pine Key, FL 33043

  Brand New Home! Oversized Custom 4 bedroom 3 bath home located on a beautiful protected deep water canal with excellent access to the Gulf and Atlantic. This 2000 sq ft home is situated in a quiet neighborhood and features an open living area design with chef's kitchen/ quartz counter tops, high ceilings, covered porch, custom railings, impact windows and doors, custom concrete heated and chilled

  Greg MacLaren Internet Realty of the Florida Keys

  2211 San Sebastian Dr, Big Pine Key, FL 33043
• 

  

  /30

  $628,000

  Sold Sep 05, 2025

  31256 Avenue H, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,144 Sq Ft
  • Built 2005

  Last Sold Summary

  • 4% Below List Price
  • $549/SF
  • 106 Days On Market

  Current Estimated Value $632,005

  Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

  31256 Avenue H, Big Pine Key, FL 33043
• 

  

  /48

  Est $672,343

  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

  • 15 Days On Market

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

  

  /51

  $825,000

  $13K PRICE DROP Under Contract

  • 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
• 

  

  /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 $2,778,367

  Last Listing Agent Stacy Shahan Island Real Estate Company Florida Keys

  23941 Henry St, Summerland Key, FL 33042
• 

  

  /19

  Est $886,071

  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

  • 498 Days On Market

  Last Listing Agent Melva Wagner Century 21 Prestige Realty Gro
• 

  

  /22

  $899,000

  $151K 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
• 

  

  /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 $2,321,792

  Last Listing Agent Jonathan Minerick Homecoin.com

  1176 Thatch Ln, Summerland Key, FL 33042
• 

  /2

  Est $1,147,383

  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
• 

  

  /27

  $320,000

  $30K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 672 Sq Ft

  701 Spanish Main Dr Unit 566, Cudjoe Key, FL 33042

  Canal-front opportunity in Venture Out! This 1 bedroom / 1 bath property offers a 17' seawall and endless potential for future use. Whether you're envisioning a personal Keys retreat or re-imagining the space as an RV lot, this property provides flexibility in a highly desirable, gated waterfront community. Enjoy all Venture Out amenities including marina access, boat ramp, pools, recreational

  Jenifer Hirsch Bluescape Real Estate

  701 Spanish Main Dr Unit 566, Cudjoe Key, FL 33042
• 

  

  /62

  $1,000,000

  Sold Aug 06, 2026

  165 Cutlass Ln, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,448 Sq Ft
  • Built 1991

  Last Sold Summary

  • $408/SF
  • 0 Days On Market

  Current Estimated Value $1,292,510

  Last Listing Agent Justyn Ewald Expert Realty LLC (HQ)

  165 Cutlass Ln, Summerland Key, FL 33042
• 

  

  /36

  Est $984,056

  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

  • 22 Days On Market

  Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty
• 

  

  /47

  $445,000

  $10K PRICE DROP

  • Land
  • 2,078 Sq Ft
  • $9,328,296 per Acre

  701 Spanish Main Dr Unit LOT 496, Cudjoe Key, FL 33042

  ROGO exempt RV Lot 496 - Waterfront Lot in Venture Out, Cudjoe Key, Mile Marker 23Bring your RV or build your Florida Keys dream home without the hassle of going through the ROGO process.Waterfront RV lot located in the gated community of Venture Out on Cudjoe Key. Lot 496 has a concrete pad, offering a durable, low-maintenance surface ideal for RV parking and outdoor living.The property features

  Lanny Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit LOT 496, Cudjoe Key, FL 33042

Showing Results 401 - 440, Page 11 of 18