Summerland Key, FL Homes

• 

  

  

  /42

  $749,000

  Sold Sep 19, 2025

  28009 Gulf Blvd, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,008 Sq Ft
  • Built 1990

  Last Sold Summary

  • 6% Below List Price
  • $743/SF
  • 88 Days On Market

  Current Estimated Value $744,866

  Last Listing Agent Ian Calderwood Bluescape Real Estate- Venture

  28009 Gulf Blvd, Big Pine Key, FL 33043
• 

  

  

  /30

  Est $728,060

  Not Listed For Sale

  19506 Seminole St, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1982

  19506 Seminole St, Summerland Key, FL 33042

  Last Sold Summary

  • 73 Days On Market
• 

  

  

  /46

  $695,000

  $104K PRICE DROP

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

  29172 Rose Dr, Big Pine Key, FL 33043

  Remodeled waterfront home! Located in a lovely neighborhood with a boat ramp right around the corner! Exterior of property has open parking as well as covered parking for multiple vehicles. Below home is surrounded by lattice to give additional shade and privacy. So much potential downstairs for outdoor entertainment.The main living area has gone through a full renovation. Kitchen boast sleek

  Deni Heintzelman KeyIsle Realty

  29172 Rose Dr, Big Pine Key, FL 33043
• 

  

  /2

  $52,000

  Sold Jun 30, 2025

  State Road 4a _ Rogo Dedication Lot, Little Torch Key, FL 33042

  • Land
  • 11,960 Sq Ft
  • $189,391 per Acre

  Last Sold Summary

  • 31% Below List Price
  • 218 Days On Market

  Last Listing Agent Sandra Dolowy Keyisle Realty

  State Road 4a _ Rogo Dedication Lot, Little Torch Key, FL 33042
• 

  

  

  /9

  Est $694,283

  Not Listed For Sale

  701 Spanish Main Dr Unit 589, Cudjoe Key, FL 33042

  • 2 Beds
  • Built 1991

  701 Spanish Main Dr Unit 589, Cudjoe Key, FL 33042

  Last Sold Summary

  • 200 Days On Market
• 

  

  /69

  $2,195,000

  $54K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 1,903 Sq Ft

  125 Colson Dr, Summerland Key, FL 33042

  TRANSIENT LICENSE FOR NIGHTLY RENTALS BRINGING IN 250k+! WITH OPEN WATER VIEWS! ALMOST 2 ACRES TOTAL WITH 4 LOTS! THIS PROPERTY IS A ONE OF A KIND! A TRUE ''UNICORN!'' Turnkey Vacation Rental with 4 bedrooms and 2 baths in Main House which is a charming and OLD FLORIDA KEYS STYLE PROPERTY! Privacy, lush vegetation, stunning Open water views from the balconies from almost every room! Original

  Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

  125 Colson Dr, Summerland Key, FL 33042
• 

  /2

  $55,000

  Sold Dec 04, 2025

  Lot 17 Treasure Chest Dr, Cudjoe Key, FL 33042

  • Land
  • 6,000 Sq Ft
  • $399,300 per Acre

  Last Sold Summary

  • 90% Above List Price
  • 73 Days On Market

  Last Listing Agent Pamela Stangler Expert Realty LLC

  Lot 17 Treasure Chest Dr, Cudjoe Key, FL 33042
• 

  

  /15

  Est $825,385

  Not Listed For Sale

  16991 Shore Dr, Summerland Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 1,134 Sq Ft
  • Built 1958

  16991 Shore Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 17 Days On Market
• 

  

  /44

  $2,295,000

  • 3 Beds
  • 2 Baths
  • 1,900 Sq Ft

  937 Gulf Dr, Summerland Key, FL 33042

  High quality concrete 3/2 in Summerland Cove. One of the best boating communities in the lower Keys for deep water, aqua blue canal water, and oceanside access with no bridges! Brand new 60' concrete dock has just been installed. Step inside to find the fresh, modern renovation done in 2024. Featuring 3 bedrooms 2 baths with the private 3rd floor primary suite. 24'' modern white tile throughout,

  Sandra Tuttle American Caribbean Real Estate Lower Keys

  937 Gulf Dr, Summerland Key, FL 33042
• 

  

  /57

  $1,550,000

  Sold Mar 02, 2026

  270 Airport Dr S, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 1,275 Sq Ft
  • Built 1980

  Last Sold Summary

  • 30% Below List Price
  • $1,216/SF
  • 63 Days On Market

  Current Estimated Value $1,534,550

  Last Listing Agent Solaris Gregory Expert Realty LLC (HQ)

  270 Airport Dr S, Summerland Key, FL 33042
• 

  

  /56

  Est $1,752,629

  Not Listed For Sale

  20966 8th Ave W, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 2,166 Sq Ft
  • Built 1982

  20966 8th Ave W, Summerland Key, FL 33042

  Last Sold Summary

  • 31 Days On Market
• 

  

  /73

  $1,099,000

  • 5 Beds
  • 2 Baths
  • 1,888 Sq Ft

  3836 No Name Rd, Big Pine Key, FL 33043

  Introducing No Name Retreat - Rare waterfront opportunity with exceptional development potential featuring 140 feet of direct water frontage and expansive 14,420 sq ft lot. The property currently includes a full duplex plus an additional buildable vacant lot, offering endless possibilities for investors, builders, or someone looking for extra room next door. Live on the water while generating

  Saara Staten Engel & Volkers Marathon

  3836 No Name Rd, Big Pine Key, FL 33043
• 

  

  /60

  $930,000

  Sold May 01, 2026

  29182 Orchid Ln, Big Pine Key, FL 33043

  • 4 Beds
  • 3 Baths
  • 2,056 Sq Ft
  • Built 1988

  Last Sold Summary

  • 6% Below List Price
  • $452/SF
  • 41 Days On Market

  Current Estimated Value $967,779

  Last Listing Agent Dawn Gonet Berkshire Hathaway HomeServices Knight & Gardner Realty

  29182 Orchid Ln, Big Pine Key, FL 33043
• 

  

  /21

  Est $839,124

  Not Listed For Sale

  19570 Mayan St, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,424 Sq Ft
  • Built 1958

  19570 Mayan St, Summerland Key, FL 33042

  Last Sold Summary

  • 1 Day On Market
• 

  

  /3

  $64,750

  • Land

  0 Lot 21 Aloha Dr, Little Torch Key, FL 33042

  ROGO Lot. Letter on hand from Monroe County granting 2 points

  Jenna Stauffer Ocean Sotheby's International Realty

  0 Lot 21 Aloha Dr, Little Torch Key, FL 33042
• 

  

  /29

  $235,000

  Sold Oct 31, 2025

  701 Spanish Main Dr Unit 621, Cudjoe Key, FL 33042

  • Land
  • 2,078 Sq Ft
  • $4,926,179 per Acre

  Last Sold Summary

  • 2% Below List Price
  • 76 Days On Market

  Current Estimated Value $247,464

  Last Listing Agent Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 621, Cudjoe Key, FL 33042
• 

  

  /73

  Est $1,121,197

  Not Listed For Sale

  103 Shore Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,128 Sq Ft
  • Built 1989

  103 Shore Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 24 Days On Market
• 

  /2

  $269,000

  $30K PRICE DROP

  • Land
  • 6,098 Sq Ft
  • $1,921,429 per Acre

  28168 Julia Ave, Little Torch Key, FL 33042

  ROGO EXEMPT LOT! Build Now, No Waiting, Water Meter On Site, 6000 SF, Boat Ramp Within Walking Distance, Live The Dream. Single family home next door going on the market soon, buy both!

  Doug Addeo Regional Trust Corporation

  28168 Julia Ave, Little Torch Key, FL 33042
• 

  

  /29

  $390,000

  Sold May 28, 2025

  28131 Helen Ave, Little Torch Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 856 Sq Ft
  • Built 1972

  Last Sold Summary

  • 8% Below List Price
  • $456/SF
  • 91 Days On Market

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

  28131 Helen Ave, Little Torch Key, FL 33042
• 

  

  /46

  Est $1,388,691

  Not Listed For Sale

  817 Grenada Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2.5 Baths
  • 1,819 Sq Ft
  • Built 1993

  817 Grenada Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 25 Days On Market
• 

  

  /41

  $590,000

  $200K PRICE DROP

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

  22920 Privateer Dr, Summerland Key, FL 33042

  Following a monumental $200,000 price drop, this rare waterfront opportunity is available at an unbeatable price point. Launch your boat from your backyard for world-class access to the Atlantic Ocean and Gulf of Mexico. Unlock instant equity with virtual additions in the photos and below-market pricing; there is significant room to secure this property way below market value after completing

  Jeff Shapiro Global Luxury Realty LLC

  22920 Privateer Dr, Summerland Key, FL 33042
• 

  

  /45

  $1,300,000

  Sold Mar 03, 2026

  1185 Hakluyt Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1989

  Last Sold Summary

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

  Current Estimated Value $1,323,929

  Last Listing Agent Greg MacLaren Internet Realty of the Florida Keys

  1185 Hakluyt Ln, Summerland Key, FL 33042
• 

  

  /44

  Est $689,691

  Not Listed For Sale

  268 Spanish Main Dr, Summerland Key, FL 33042

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

  268 Spanish Main Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 86 Days On Market
• 

  

  /26

  $465,000

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

  30461 Poinciana Rd, Big Pine Key, FL 33043

  Charming home on an oversized double lot (12,500 sqft) in Big Pine Key. This 3-bedroom 2 bath home, with an office, features a vaulted ceiling, new mini split air condition units, abundance of natural lighting, French doors leading to a large screened in porch, great entertaining area. A large primary bedroom has another screened in porch off the back that is shared with separate1/1 guest suite.

  Dorothy Santiago Keller Williams Realty Professionals (KW)

  30461 Poinciana Rd, Big Pine Key, FL 33043
• 

  

  /61

  $3,900,000

  Sold Feb 27, 2026

  16200 Old State Rd Unit 4A, Sugarloaf Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,964 Sq Ft
  • Built 2024

  Last Sold Summary

  • 2% Below List Price
  • $1,986/SF
  • 25 Days On Market

  Current Estimated Value $3,817,664

  Last Listing Agent Madeleine Lowe Expert Realty LLC (HQ)

  16200 Old State Rd Unit 4A, Sugarloaf Key, FL 33042
• 

  

  /36

  Est $1,000,248

  Not Listed For Sale

  21066 3rd Ave, Summerland Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 1,245 Sq Ft
  • Built 1974

  21066 3rd Ave, Summerland Key, FL 33042

  Last Sold Summary

  • 326 Days On Market
• 

  

  /33

  $249,000

  $30K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 368 Sq Ft

  701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042

  Welcome to Unit 533 in the Venture Out community on Cudjoe Key, featuring a spacious addition that provides extra living space and flexibility. The addition includes a comfortable living area and a flex room currently used as additional sleeping space, suitable for guests, a home office, or hobby area. The home is clean and well cared for, offering a functional layout appropriate for full-time

  Jenifer Hirsch Bluescape Real Estate

  701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042
• 

  

  /42

  $1,000,000

  Sold Jun 20, 2025

  27330 Barbados Ln, Ramrod Key, FL 33042

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

  Last Sold Summary

  • 16% Below List Price
  • $567/SF
  • 79 Days On Market

  Current Estimated Value $1,044,019

  Last Listing Agent Brian Kruszewski LoKation Real Estate

  27330 Barbados Ln, Ramrod Key, FL 33042
• 

  

  /43

  Est $947,177

  Not Listed For Sale

  447 Pirates Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 984 Sq Ft
  • Built 1991

  447 Pirates Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 51 Days On Market
• 

  

  /45

  $510,000

  $19K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 758 Sq Ft

  701 Spanish Main Dr Unit 417, Cudjoe Key, FL 33042

  MOTIVATED SELLER! Turn-key 2BR/2BA waterfront fully furnished home with 35' concrete dock and patio furniture included, Front door paver patio, impact slider doors and windows, gas stove, and ample storage including outdoor dock box. Enjoy direct, deep-water access to the Ocean & Gulf, perfect for boating, fishing, and breathtaking sunrises & sunsets. Located in Venture Out, a gated, golf

  Amanda Taylor Bluescape Real Estate

  701 Spanish Main Dr Unit 417, Cudjoe Key, FL 33042
• 

  

  /36

  $685,000

  Sold Oct 15, 2025

  701 Spanish Main Dr Unit 77, Cudjoe Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft
  • Built 2010

  Last Sold Summary

  • 16% Below List Price
  • $793/SF
  • 164 Days On Market

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

  701 Spanish Main Dr Unit 77, Cudjoe Key, FL 33042
• 

  /2

  Est $1,352,940

  Not Listed For Sale

  23047 Bluegill Ln, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 1,440 Sq Ft
  • Built 1991

  23047 Bluegill Ln, Summerland Key, FL 33042

  Last Sold Summary
• 

  

  /31

  $925,000

  • 2 Beds
  • 2 Baths
  • 1,291 Sq Ft

  31364 Avenue J, Big Pine Key, FL 33043

  Open Waterfront Double Lot with Protected Boating and Endless PossibilitiesDiscover the best of Florida Keys waterfront living on this spacious double lot located on a quiet street on the open water with 150 feet of protective canal frontage with seawall, this property offers direct boating access to both the backcountry and the Atlantic Ocean and is only one lot in from the mouth of the canal

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

  31364 Avenue J, Big Pine Key, FL 33043
• 

  

  /51

  $990,000

  Sold Oct 28, 2025

  22841 Buccaneer Ln, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 1,920 Sq Ft
  • Built 1963

  Last Sold Summary

  • 10% Below List Price
  • $516/SF
  • 139 Days On Market

  Current Estimated Value $1,130,680

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  22841 Buccaneer Ln, Summerland Key, FL 33042
• 

  

  /20

  Est $838,262

  Not Listed For Sale

  27370 W Indies Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1992

  27370 W Indies Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 118 Days On Market
• 

  

  /4

  $675,000

  • Land
  • 13,503 Sq Ft
  • $2,177,419 per Acre

  2080 Coral Way, Big Pine Key, FL 33043

  Rare opportunity to own a stunning ocean view double lot with 107 feet of canal frontage in sought-after Big Pine Key! Currently #5 in ROGO, this prime property comes with approved building plans—available upon request. The spacious lot offers ample room for your dream home with direct canal access and breathtaking open-water views. Buyers may have the ability to modify the existing plans—please

  Kelly Acosta ARGO GROUP PROPERTIES LLC

  2080 Coral Way, Big Pine Key, FL 33043
• 

  

  /46

  $550,000

  Sold May 28, 2025

  701 Spanish Main Dr Unit 415, Cudjoe Key, FL 33042

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

  Last Sold Summary

  • 12% Below List Price
  • $729/SF
  • 72 Days On Market

  Last Listing Agent Jan Fritz Coldwell Banker Schmitt RE Co.

  701 Spanish Main Dr Unit 415, Cudjoe Key, FL 33042
• 

  

  /49

  Est $1,871,142

  Not Listed For Sale

  22766 Jolly Roger Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,884 Sq Ft
  • Built 1989

  22766 Jolly Roger Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 80 Days On Market
• 

  

  /53

  $2,375,000

  • 5 Beds
  • 4 Baths
  • 2,772 Sq Ft

  205 S Point Dr, Summerland Key, FL 33042

  Experience elevated waterfront living at this stunning South Point Sugarloaf Key retreat, where open-water serenity meets refined island design. This exceptional five-bedroom, four-bathroom residence is thoughtfully designed to host family and guests with ease, featuring a desirable split-floor plan and expansive living spaces framed by endless turquoise views. The primary suite is a private

  Dawn McComish Lokation Real Estate

  205 S Point Dr, Summerland Key, FL 33042
• 

  

  /36

  $1,225,000

  Sold Jun 13, 2025

  165 Colson Dr, Cudjoe Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,696 Sq Ft
  • Built 2023

  Last Sold Summary

  • 5% Below List Price
  • $722/SF
  • 104 Days On Market

  Current Estimated Value $1,273,920

  Last Listing Agent Terry Garcia Keller Williams Key West Compass Realty

  165 Colson Dr, Cudjoe Key, FL 33042

Showing Results 601 - 640, Page 16 of 18