Summerland Key, FL Homes

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  /26

  $390,000 Sold Jul 10, 2025

  27873 Coral Shores Rd, Little Torch Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 686 Sq Ft
  • Built 1985

  Last Sold Summary

  • 19% Below List Price
  • $569/SF
  • 70 Days On Market

  Last Listing Agent Tracy Shields KeyIsle Realty

  27873 Coral Shores Rd, Little Torch Key, FL 33042
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  /2

  Not Listed For Sale

  3 Big Pine Ave, Big Pine Key, FL 33043

  3 Big Pine Ave, Big Pine Key, FL 33043
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  /33

  $995,000

  • 3 Beds
  • 2 Baths
  • 1,494 Sq Ft

  27417 Tobago Ln, Ramrod Key, FL 33042

  This custom-built 3-bedroom, 2-bathroom residence on Ramrod Key offers a spacious, split floorplan, 1500 sq ft and is just 27 miles from Key West. The high quality 2010 construction features a hip metal roof, hardi plank siding, impact windows, and doors, ensuring durability and peace of mind. The heart of this home is its large kitchen, designed for both function and style. With an abundance of

  

  Sandra Tuttle

  Island Welcome Real Estate

  (786) 822-7622

  27417 Tobago Ln, Ramrod Key, FL 33042
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  /64

  $809,000 Sold Nov 12, 2025

  3714 Pine St, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 1989

  Last Sold Summary

  • 17% Below List Price
  • $722/SF
  • 194 Days On Market

  Last Listing Agent Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

  3714 Pine St, Big Pine Key, FL 33043
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  /2

  Not Listed For Sale

  2 Big Pine Ave, Big Pine Key, FL 33043

  2 Big Pine Ave, Big Pine Key, FL 33043
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  /49

  $869,000 Under Contract

  • 2 Beds
  • 2 Baths
  • 984 Sq Ft

  3987 Gordon Rd, Big Pine Key, FL 33043

  Tastefully updated and move-in ready so you can enjoy life in the Keys! The recent 8' x 30' composite dock features a 12,000 lb. boat lift providing good boat access to the back country and Atlantic. The outdoor space is maximized for entertaining or relaxing. Inside you'll find the open great room with cathedral ceiling and spacious kitchen with hickory cabinets, quartz counters and a sea glass

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  (833) 302-4216

  3987 Gordon Rd, Big Pine Key, FL 33043
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  /2

  $144,000 Sold Mar 04, 2025

  Lot 15 Aztec St, Sugarloaf Key, FL 33042

  • Land

  Last Sold Summary

  • 4% Below List Price
  • 2 Days On Market

  Last Listing Agent Vic Musmanno Coldwell Banker Schmitt Real Estate Co. (KW)

  Lot 15 Aztec St, Sugarloaf Key, FL 33042
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  /2

  Not Listed For Sale

  1 Big Pine Ave, Big Pine Key, FL 33043

  1 Big Pine Ave, Big Pine Key, FL 33043
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  /38

  $1,499,000

  • 3 Beds
  • 2 Baths
  • 1,356 Sq Ft

  51 Drost Dr, Summerland Key, FL 33042

  Originally built as the developer of Cudjoe Gardens personal residence, this exceptional Mid-Century Modern waterfront home captures the effortless glamour of Palm Springs design blended with the laid-back sophistication of the Florida Keys. Offering 3 Bedrooms and 2 Baths, the residence has been beautifully remodeled with meticulous attention to detail, honoring its architectural roots while

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 551-4933

  51 Drost Dr, Summerland Key, FL 33042
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  /33

  $799,000 Sold Apr 28, 2025

  24833 Park Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,166 Sq Ft
  • Built 1956

  Last Sold Summary

  • 11% Below List Price
  • $685/SF
  • 115 Days On Market

  Current Estimated Value $803,558

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

  24833 Park Dr, Summerland Key, FL 33042
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  /9

  Not Listed For Sale

  22819 Blackbeard Ln, Cudjoe Key, FL 33042

  22819 Blackbeard Ln, Cudjoe Key, FL 33042
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  /55

  $2,300,000

  • 3 Beds
  • 3 Baths
  • 2,010 Sq Ft

  948 Gulf Dr, Summerland Key, FL 33042

  Luxury coastal living meets unmatched boating convenience at this fully renovated canal-front stunner in prestigious Summerland Cove Islands. Situated on a 7,575 sq ft lot with 75 ft of concrete dockage, a 20K lb boat lift, and quick ocean access via wide, flow-through canals -- this 3 Bedroom, 3 Bathroom home is a dream for boating enthusiasts. Inside, this 2,010 sq ft two-story retreat

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 833-9579

  948 Gulf Dr, Summerland Key, FL 33042
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  /8

  $340,000 Sold Dec 11, 2025

  0 Overseas Hwy, Summerland Key, FL 33042

  • Land
  • 0.29 Acre
  • $1,184,832 per Acre

  Last Sold Summary

  • 3% Below List Price
  • 328 Days On Market

  Last Listing Agent Stacy Shahan Island Real Estate Company Florida Keys

  0 Overseas Hwy, Summerland Key, FL 33042
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  /2

  Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 672 Sq Ft

  28177 Julia Ave, Little Torch Key, FL 33042

  28177 Julia Ave, Little Torch Key, FL 33042
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  /50

  $1,600,000

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

  947 Gulf Dr, Summerland Key, FL 33042

  There's a certain feeling you get the moment you pull onto Summerland Cove Isle, quiet, breezy, and unmistakably upscale. The kind of street where every home has been cared for, every canal sparkles, and the water itself seems to move with purpose. This home sits on the most coveted stretch of the island, where the flow-through, crystal-clear, extra-deep canals are the heartbeat of the

  

  Coby Taylor

  Taylor & Assoc. RE, Inc.

  (786) 983-9115

  947 Gulf Dr, Summerland Key, FL 33042
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  /21

  $380,000 Sold Jun 24, 2025

  27848 Lobster Tail Trail, Little Torch Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 552 Sq Ft
  • Built 1971

  Last Sold Summary

  • 24% Below List Price
  • $688/SF
  • 248 Days On Market

  Last Listing Agent Derrick Johnson Coco Plum Real Estate

  27848 Lobster Tail Trail, Little Torch Key, FL 33042
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  /2

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,170 Sq Ft

  30919 Edward Rd Unit A & B, Big Pine Key, FL 33043

  30919 Edward Rd Unit A & B, Big Pine Key, FL 33043
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  /4

  $285,000

  • Land

  Unlisted Address

  Private Acre on Cudjoe Key. Lush, Tropical, and Near the Water Escape to your own secluded paradise in the Lower Keys! This just over an acre lot on Cudjoe Key is surrounded by beautiful equestrian properties and dense tropical foliage, offering unmatched privacy and tranquility. Located just seconds from a public boat ramp, you'll have easy access to world-class fishing, boating, and

  

  Coby Taylor

  Taylor & Assoc. RE, Inc.

  (786) 876-6382

  Unlisted Address
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  /33

  $630,000 Sold Jan 09, 2025

  30361 Harding Rd, Big Pine Key, FL 33043

  • 2 Beds
  • 1.5 Baths
  • 888 Sq Ft
  • Built 1963

  Last Sold Summary

  • 16% Below List Price
  • $709/SF
  • 295 Days On Market

  Current Estimated Value $625,269

  Last Listing Agent David Kaufmann Century 21 Circle

  30361 Harding Rd, Big Pine Key, FL 33043
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  /2

  Est $231,079 Not Listed For Sale

  • Studio

  951 Hawksbill Ln, Sugarloaf Key, FL 33042

  951 Hawksbill Ln, Sugarloaf Key, FL 33042
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  /59

  $1,180,000

  • 4 Beds
  • 2 Baths
  • 1,674 Sq Ft

  3831 Sunset Dr, Big Pine Key, FL 33043

  Stunning water views and gorgeous sunsets will be yours from this slice of Keys paradise where the 7,000 sq. ft. setting couldn't be more peaceful! It's a short, 300 ft. canal ride to the Pine Channel; the Content Keys are about 20 minutes away by boat and the Atlantic is also within easy reach. A few of the property's highlights are the 70 ft. concrete seawall with davits, multiple porches,

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  (866) 589-3517

  3831 Sunset Dr, Big Pine Key, FL 33043
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  $760,000 Sold Aug 19, 2025

  640 Carolyn Ave, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 848 Sq Ft
  • Built 2021

  Last Sold Summary

  • 2% Below List Price
  • $896/SF
  • 66 Days On Market

  Current Estimated Value $764,792

  Last Listing Agent Tommy Mack Coastal Collection Real Estate Inc.

  640 Carolyn Ave, Summerland Key, FL 33042
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  /8

  Est $414,737 Not Listed For Sale

  53 Sugarloaf Dr, Sugarloaf Shores, FL 33042

  53 Sugarloaf Dr, Sugarloaf Shores, FL 33042
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  /77

  $12,999,999

  • 31 Beds
  • 19 Baths

  21470 Overseas Hwy, Cudjoe Key, FL 33042

  Located on Cudjoe Key, only 20 miles from Key West. Transient use property, over 3.5 acres, 15 units (15 ROGO exemptions), over 300 feet of water frontage, boat basin, 3 concrete docks, one wooden dock, boat ramp. Shared coin laundry, 2 swimming pools, 3 private driveways. 2 parcels on US 1 are zoned Sub Urban Commercial, excellent rental history. Property spans from US 1 to the Atlantic Ocean.

  

  Jennifer Weeks

  Select Properties of NWFL

  (786) 882-8127

  21470 Overseas Hwy, Cudjoe Key, FL 33042
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  $239,000 Sold Jun 30, 2025

  701 Spanish Main Dr Unit 6, Cudjoe Key, FL 33042

  • Land

  Last Sold Summary

  • 2% Below List Price
  • 74 Days On Market

  Current Estimated Value $244,697

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

  701 Spanish Main Dr Unit 6, Cudjoe Key, FL 33042
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  /2

  Not Listed For Sale

  430 Les Rohde Dr, Ramrod Key, FL 33042

  430 Les Rohde Dr, Ramrod Key, FL 33042
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  /48

  $1,499,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,728 Sq Ft

  17166 Wahoo Ln W, Summerland Key, FL 33042

  This spacious 1,723 sq. ft. 3 Bedroom 2 Bath canal front Pool home is located in prestigious Sugarloaf Shores, an upscale community of waterfront homes just 15 miles from the magic of Key West. The resort-style home boasts a tropical waterfront pool with adjacent tiki bar to enjoy refreshments after a day out on the water. Boaters will appreciate the 100' of concrete dockage with davits on an 80'

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 744-8525

  17166 Wahoo Ln W, Summerland Key, FL 33042
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  /25

  $310,000 Sold Mar 13, 2025

  28232 Dorothy Ave, Summerland Key, FL 33042

  • 2 Beds
  • 1.5 Baths
  • 1,064 Sq Ft
  • Built 1986

  Last Sold Summary

  • 9% Below List Price
  • $291/SF
  • 49 Days On Market

  Last Listing Agent Lanny Gardner Bluescape Real Estate

  28232 Dorothy Ave, Summerland Key, FL 33042
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  /2

  Est $613,887 Not Listed For Sale

  • Studio

  20874 4th Ave, Cudjoe Key, FL 33042

  20874 4th Ave, Cudjoe Key, FL 33042
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  /49

  $1,145,000

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

  22737 Blackbeard Ln, Cudjoe Key, FL 33042

  Welcome home to your coastal oasis! This stunning brand-new elevated home features three bedrooms, two bathrooms, with an open concept living room and kitchen plus a covered 10x30 porch. Additional features include impact resistance windows and doors, metal roof, Azek decking, powder coated aluminum railings, custom concrete dock (8x20) with a permitted 12,000 Ibs. boat lift with 298 sq. ft. of

  

  Terry Garcia

  Keller Williams Key West Compass Realty

  (786) 321-8407

  22737 Blackbeard Ln, Cudjoe Key, FL 33042
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  $2,800,000 Sold Oct 30, 2025

  22967 Redfish Ln, Cudjoe Key, FL 33042

  • 3 Beds
  • 4 Baths
  • 3,747 Sq Ft
  • Built 2019

  Last Sold Summary

  • 7% Below List Price
  • $747/SF
  • 37 Days On Market

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

  22967 Redfish Ln, Cudjoe Key, FL 33042
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  /2

  Not Listed For Sale

  0 Vacant Land Unit 603907, Sugarloaf Key, FL 33042

  0 Vacant Land Unit 603907, Sugarloaf Key, FL 33042
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  /47

  $649,000 New Construction

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft

  701 Spanish Main Dr Unit 30, Cudjoe Key, FL 33042

  Welcome to your piece of paradise in the exclusive gated community of Venture Out on Cudjoe Key. This stunning high-rise, built in 2024, embodies the perfect blend of modern luxury and island life. As you step inside, you are greeted by an inviting atmosphere that captures the essence of coastal living. The master bedroom boasts an en suite bathroom, offering a serene retreat at the end of the

  

  Ian Calderwood

  Bluescape Real Estate

  (786) 613-4104

  701 Spanish Main Dr Unit 30, Cudjoe Key, FL 33042
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  /2

  $55,000 Sold Jun 02, 2025

  0 Canal Dr, Sugarloaf Key, FL 33042

  • Land

  Last Sold Summary

  • 11% Below List Price
  • 32 Days On Market

  Last Listing Agent Nate Meyer Meyer and Boumerhi Realty LLC

  0 Canal Dr, Sugarloaf Key, FL 33042
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  /2

  Est $1,116,815 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,361 Sq Ft

  21034 Overseas Hwy, Cudjoe Key, FL 33042

  21034 Overseas Hwy, Cudjoe Key, FL 33042
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  $830,000

  • 3 Beds
  • 2 Baths
  • 1,513 Sq Ft

  30471 Coconut Hwy, Big Pine Key, FL 33043

  Experience the charm of this beautifully renovated split-level home, designed with privacy and elegance in mind. The elevated master suite ensures a peaceful retreat, while additional spaces offer the versatile of an office or separate family room perfect for relaxation or entertaining. Step through the bedroom doors onto a spacious deck, where you can enjoy views of the meticulously landscaped

  Richard Haskins Buy The Keys

  30471 Coconut Hwy, Big Pine Key, FL 33043
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  /43

  $990,000 Sold Dec 10, 2025

  29839 Newfound Blvd, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,750 Sq Ft
  • Built 1995

  Last Sold Summary

  • 1% Below List Price
  • $566/SF
  • 4 Days On Market

  Last Listing Agent Donna Halstead Coldwell Banker Schmitt RE Co.

  29839 Newfound Blvd, Big Pine Key, FL 33043
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  /2

  Not Listed For Sale

  • 7,000 Sq Ft

  1138 Basque Ln, Summerland Key, FL 33042

  1138 Basque Ln, Summerland Key, FL 33042
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  $975,000

  • 4 Beds
  • 3 Baths
  • 2,493 Sq Ft

  30451 Hibiscus Ln, Big Pine Key, FL 33043

  ONE-OF-A-KIND! Custom-built home on a large 31,250 sqft lot. Built in 2010. 4bd/3bth plus office or bonus room for a total 2493 sqft. Perfect for 2 working professionals from home or a big family. Good size bedrooms; 2 are ensuite. 4 Bedrooms/3 batths. Rooms are large. Separate Kitchen Dining & Living Room and an extra room for office or hobbies or guest. etc. Below the house, there is a concrete

  Rose Dell Keller Williams Key West Compass Realty

  30451 Hibiscus Ln, Big Pine Key, FL 33043
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  $1,850,000 Sold Jan 30, 2025

  27339 Saint Vincent Ln, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 1,644 Sq Ft
  • Built 2011

  Last Sold Summary

  • 7% Below List Price
  • $1,125/SF
  • 86 Days On Market

  Current Estimated Value $1,570,477

  Last Listing Agent Michelle Howerton Brenda Donnelly Real Estate LLC

  27339 Saint Vincent Ln, Summerland Key, FL 33042

Showing Results 201 - 240, Page 6 of 18