Summerland Key, FL Homes

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  /12

  $240,000

  Pending

  • 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

  28177 Julia Ave, Little Torch Key, FL 33042
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  /26

  $335,000

  Sold May 12, 2026

  31042 Avenue J, Big Pine Key, FL 33043

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Built 1987

  Last Sold Summary

  • 16% Below List Price
  • $372/SF
  • 8 Days On Market

  Current Estimated Value $388,377

  Last Listing Agent John Nazzaro Keller Williams Realty Premier Properties - Kendall

  31042 Avenue J, Big Pine Key, FL 33043
• 

  

  

  /41

  Est $1,102,693

  Not Listed For Sale

  366 Sawyer Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,390 Sq Ft
  • Built 1988

  366 Sawyer Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 4 Days On Market
• 

  

  

  /49

  $1,450,000

  $150K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,396 Sq Ft

  29635 Saratoga Ave, Big Pine Key, FL 33043

  Welcome to your slice of island paradise in Pine Channel Estates in Big Pine Key! This beautifully built 3bedroom, 2bath CBS home offers the perfect blend of durability, comfort, and laid-back Keys living. Constructed with poured concrete floors and designed for peace of mind, the home features a tiled interior, a tiled roof, and convenient accordion shutters throughout. Step outside and embrace

  Karen Haack Coldwell Banker Schmitt RE Co.

  29635 Saratoga Ave, Big Pine Key, FL 33043
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  /36

  $700,000

  Sold Jan 29, 2026

  24830 Park Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft
  • Built 2015

  Last Sold Summary

  • 3% Below List Price
  • $589/SF
  • 7 Days On Market

  Current Estimated Value $725,929

  Last Listing Agent Patti Nickless Coldwell Banker Schmitt RE Co.

  24830 Park Dr, Summerland Key, FL 33042
• 

  

  /44

  Est $829,768

  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
• 

  

  /7

  $1,600,000

  • Land
  • 1.01 Acres
  • $1,584,158 per Acre

  0 Racoon Run, Big Pine Key, FL 33043

  Rare opportunity to own 1 acre in beautiful Big Pine Key, Florida! Build your dream island retreat in one of the most desirable areas of the Lower Keys. Enjoy the natural beauty, tropical surroundings, boating, fishing, snorkeling, and the laid-back Florida Keys lifestyle. Big Pine Key is known for its peaceful atmosphere, abundant wildlife, and proximity to the National Key Deer Refuge.

  Sara Baldomero Ribot HOME PRIME REALTY LLC

  0 Racoon Run, Big Pine Key, FL 33043
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  /32

  $1,282,100

  Sold Nov 04, 2025

  32857 Tortuga Ln, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1994

  Last Sold Summary

  • 8% Below List Price
  • $916/SF
  • 23 Days On Market

  Current Estimated Value $1,341,334

  Last Listing Agent Madeleine Lowe Expert Realty LLC (HQ)

  32857 Tortuga Ln, Big Pine Key, FL 33043
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  /36

  Est $1,006,504

  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
• 

  

  /72

  $595,000

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  701 Spanish Main Dr Unit 604, Cudjoe Key, FL 33042

  Owner says ''Bring All Offers''Charming Coastal Retreat: 2 Bedroom, 2 Bath home with 35' concrete seawall. Nightly Rentals allowed.Welcome to your perfect getaway or investment opportunity! This delightful home built in 1993, offers 816 sq. ft. of comfortable living space, fully furnished and turn-key, making it an ideal choice for both relaxation and income generation. Step inside to discover a

  Lanny Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 604, Cudjoe Key, FL 33042
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  /2

  $357,000

  Sold Nov 07, 2025

  31145 Hibiscus Dr, Big Pine Key, FL 33043

  • Land
  • 5,399 Sq Ft
  • $2,879,800 per Acre

  Last Sold Summary

  • 11% Below List Price
  • 222 Days On Market

  Current Estimated Value $364,185

  Last Listing Agent Cheryl Moses Action Keys Realty of the Lower FL Keys LLC

  31145 Hibiscus Dr, Big Pine Key, FL 33043
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  /27

  Est $875,737

  Not Listed For Sale

  27417 Cayman Ln, Summerland Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 1,085 Sq Ft
  • Built 1975

  27417 Cayman Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 274 Days On Market
• 

  

  /62

  $2,599,000

  • 3 Beds
  • 2 Baths
  • 2,224 Sq Ft

  16843 E Point Dr, Summerland Key, FL 33042

  Welcome to your private waterfront retreat in the highly sought-after Southpoint neighborhood of Sugarloaf Key - where space, privacy and effortless access to the open water redefine the Lower Keys Lifestyle. Positioned along a crystal clear canal just moments from the Bay, this elevated residence offers over 2200 sq.ft of thoughtfully designed living space, featuring three spacious bedrooms and

  Suzanne Moore Truman & Co. (KW)

  16843 E Point Dr, Summerland Key, FL 33042
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  /35

  $560,000

  Sold Aug 29, 2025

  19616 Aztec St, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,129 Sq Ft
  • Built 1953

  Last Sold Summary

  • 20% Below List Price
  • $496/SF
  • 196 Days On Market

  Current Estimated Value $601,827

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  19616 Aztec St, Summerland Key, FL 33042
• 

  

  /43

  Est $962,069

  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
• 

  

  /3

  $215,000

  • Land
  • 7,840 Sq Ft
  • $1,194,444 per Acre

  27334 Saint Lucie Ln, Big Pine, FL 33042

  Rare opportunity to own a piece of paradise in the heart of the Florida Keys. Located in the desirable Breezeswept Beach Estates community on Ramrod Key, this canal-front homesite offers the perfect blend of tranquility, natural beauty, and island living. The property benefits from a recorded Lot Line Adjustment that established the current buildable lot configuration, creating an excellent

  Gilberto Imery Gilvan Realty Corp

  27334 Saint Lucie Ln, Big Pine, FL 33042
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  /10

  $2,000,000

  Sold Jul 14, 2025

  441 Airport Dr N, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 2,256 Sq Ft
  • Built 2001

  Last Sold Summary

  • 13% Below List Price
  • $887/SF
  • 166 Days On Market

  Current Estimated Value $2,110,909

  Last Listing Agent Jonathan Minerick Homecoin.com

  441 Airport Dr N, Summerland Key, FL 33042
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  /27

  Est $2,034,315

  Not Listed For Sale

  17022 Starfish Ln W, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,990 Sq Ft
  • Built 1994

  17022 Starfish Ln W, Summerland Key, FL 33042

  Last Sold Summary

  • 85 Days On Market
• 

  

  /50

  $1,349,000

  $100K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,820 Sq Ft

  845 Pirates Rd, Summerland Key, FL 33042

  Discover waterfront living in Jolly Roger Estates on Little Torch Key. This beautifully maintained 3 bedroom, 3 bathroom canal-front home offers quick boating access to open water, making it ideal for fishing and island adventures.Designed for the Florida Keys lifestyle, the property features a private pool, tiki hut, and spacious outdoor entertaining areas overlooking the canal. Boaters will

  Sandra Dolowy KeyIsle Realty

  845 Pirates Rd, Summerland Key, FL 33042
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  /36

  $840,000

  Sold Jun 26, 2026

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

  • 2 Beds
  • 2 Baths
  • 861 Sq Ft
  • Built 1999

  Last Sold Summary

  • 14% Below List Price
  • $976/SF
  • 159 Days On Market

  Last Listing Agent Jamie Caudill Lokation Real Estate

  701 Spanish Main Dr Unit 512, Cudjoe Key, FL 33042
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  /2

  Est $1,317,263

  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
• 

  

  /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
• 

  

  /90

  $1,075,000

  Sold May 11, 2026

  21855 Spain Blvd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,467 Sq Ft
  • Built 1985

  Last Sold Summary

  • 10% Below List Price
  • $733/SF
  • 28 Days On Market

  Current Estimated Value $988,193

  Last Listing Agent Patti Nickless Coldwell Banker Schmitt RE Co.

  21855 Spain Blvd, Summerland Key, FL 33042
• 

  

  /20

  Est $860,884

  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
• 

  

  /58

  $1,299,000

  $100K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,398 Sq Ft

  885 Hawksbill Ln, Summerland Key, FL 33042

  Recently updated canal-front home in highly desirable Upper Sugarloaf Key with direct boating access to the world famous Florida Keys back-country and Gulf of America. Located at 885 Hawksbill Lane, this waterfront property sits on a 6,120 sq ft lot and features a concrete seawall with boat davits, pavers and a heated swimming pool and spa completed in 2022. Enjoy canal and mangrove views plus

  Tommy Mack Coastal Collection Real Estate Inc.

  885 Hawksbill Ln, Summerland Key, FL 33042
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  /40

  $635,000

  Sold Aug 29, 2025

  31148 Avenue C, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,272 Sq Ft
  • Built 2003

  Last Sold Summary

  • 9% Below List Price
  • $499/SF
  • 212 Days On Market

  Current Estimated Value $641,897

  Last Listing Agent Sandra Rodriguez Lokation Real Estate

  31148 Avenue C, Big Pine Key, FL 33043
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  /49

  Est $1,765,161

  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
• 

  

  /45

  $1,269,000

  Open Sun 11AM - 2PM

  • 2 Beds
  • 2 Baths
  • 1,100 Sq Ft

  116 Spanish Main Dr, Summerland Key, FL 33042

  Discover your personal island sanctuary in the heart of Cudjoe Key, where every day feels like Margaritaville. This stunning 2-bedroom, 2-bathroom single-family home has been thoughtfully updated to offer the ultimate waterfront lifestyle, featuring a sleek kitchen with a central island, 2025 updated appliances and two beautifully remodeled bathrooms. The interior glows with natural light,

  Tina Fingerman Beaches MLS

  116 Spanish Main Dr, Summerland Key, FL 33042
• 

  

  /58

  $1,164,000

  Sold Dec 12, 2025

  164 Tortuga Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1990

  Last Sold Summary

  • 3% Below List Price
  • $831/SF
  • 27 Days On Market

  Current Estimated Value $1,201,382

  Last Listing Agent Michele Adams Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

  164 Tortuga Ln, Summerland Key, FL 33042
• 

  

  /29

  Est $1,857,934

  Not Listed For Sale

  17234 Green Turtle Ln E, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,880 Sq Ft
  • Built 1963

  17234 Green Turtle Ln E, Summerland Key, FL 33042

  Last Sold Summary

  • 275 Days 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
• 

  

  /82

  $1,265,000

  Sold Apr 27, 2026

  29653 Saratoga Ave, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,596 Sq Ft
  • Built 1980

  Last Sold Summary

  • 2% Below List Price
  • $793/SF
  • 3 Days On Market

  Current Estimated Value $1,273,863

  Last Listing Agent Patti Nickless Coldwell Banker Schmitt RE Co.

  29653 Saratoga Ave, Big Pine Key, FL 33043
• 

  /2

  Est $1,186,142

  Not Listed For Sale

  19563 Canal Dr, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,112 Sq Ft
  • Built 1990

  19563 Canal Dr, Summerland Key, FL 33042
• 

  /2

  $249,000

  $50K PRICE DROP

  • Land
  • 6,098 Sq Ft
  • $1,778,571 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
• 

  

  /32

  $970,000

  Sold Jul 08, 2026

  17287 Cayman Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,488 Sq Ft
  • Built 2013

  Last Sold Summary

  • 3% Below List Price
  • $652/SF
  • 42 Days On Market

  Current Estimated Value $1,042,901

  Last Listing Agent Jonathan Minerick Homecoin.com

  17287 Cayman Dr, Summerland Key, FL 33042
• 

  

  /56

  Est $1,722,654

  Not Listed For Sale

  17159 Amberjack Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,660 Sq Ft
  • Built 1989

  17159 Amberjack Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 258 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
• 

  /2

  $570,000

  Sold Jul 17, 2025

  3767 Hibiscus St, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft
  • Built 1986

  Last Sold Summary

  • 4% Below List Price
  • $594/SF
  • 6 Days On Market

  Current Estimated Value $616,897

  Last Listing Agent Ryan Call REALTY ZOOM

  3767 Hibiscus St, Big Pine Key, FL 33043
• 

  

  /29

  Est $907,190

  Not Listed For Sale

  27359 Jamaica Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1995

  27359 Jamaica Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 33 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

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