Summerland Key, FL Homes

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  /30

  $740,000 Sold Jan 21, 2025

  124 Yardarm Rd, Cudjoe Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,064 Sq Ft
  • Built 2023

  Last Sold Summary

  • 1% Below List Price
  • $695/SF
  • 22 Days On Market

  Current Estimated Value $735,941

  Last Listing Agent The Spottswood Team Truman & Co. (KW)

  124 Yardarm Rd, Cudjoe Key, FL 33042
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  /2

  Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,680 Sq Ft

  29527 Constitution Ave, Big Pine Key, FL 33043

  29527 Constitution Ave, Big Pine Key, FL 33043
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  /43

  $1,125,000

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

  22837 Calico Jack Cir, Summerland Key, FL 33042

  Seller says Bring Offers....Open Water Views & Sunset Skies with great boating access describes this Concrete Block Construction Home with pre-stress concrete beams holding up a poured concrete floor. Home features open floor plan with vaulted ceilings, tile floors throughout, partial walk-around, storm shutters, 2018 A/C, impact front door and metal roof. Storage room below and ample parking

  Beata Sharpe Coldwell Banker Vanguard Realty

  22837 Calico Jack Cir, Summerland Key, FL 33042
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  /51

  $975,000 Sold Aug 01, 2025

  527 Heck Ave, Little Torch Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 2023

  Last Sold Summary

  • 17% Below List Price
  • $812/SF
  • 101 Days On Market

  Current Estimated Value $959,050

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

  527 Heck Ave, Little Torch Key, FL 33042
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  /14

  Est $454,559 Not Listed For Sale

  • 1 Bed

  701 Spanish Main Dr Unit 432, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 432, Cudjoe Key, FL 33042
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  /56

  $6,995,000 Pending

  • 5 Beds
  • 6 Baths
  • 3,952 Sq Ft

  1151 Ocean Dr, Summerland Key, FL 33042

  This luxe, oceanfront estate will be sold at Luxury AUCTION Without Reserve on December 4, 2025! List price for REFERENCE ONLY. Offered in co-op. with Platinum Luxury Auctions. Inquire for details.Trophy Oceanfront Estate in THE PRIME location on Ocean Dr Summerland Key - surrounded by multi million dollar estates favored by celebrities and business leaders. Fly in and boat out! Located in one of

  Lisa Swanson The Agency Florida Keys

  1151 Ocean Dr, Summerland Key, FL 33042
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  /56

  $1,625,000 Sold Apr 04, 2025

  30463 Hawk Ln, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,882 Sq Ft
  • Built 1989

  Last Sold Summary

  • 40% Below List Price
  • $863/SF
  • 413 Days On Market

  Current Estimated Value $1,446,364

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

  30463 Hawk Ln, Big Pine Key, FL 33043
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  /2

  Est $827,905 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft

  53 Gold Boullion Rd, Cudjoe Key, FL 33042

  53 Gold Boullion Rd, Cudjoe Key, FL 33042
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  /41

  $795,000

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft

  251 Pelican Ln, Big Pine Key, FL 33043

  Tropical Retreat on Two Lots. Discover your slice of paradise with this lovely updated concrete block home, perfectly positioned on an oversized property with serene canal frontage. Move-in ready, meticulously maintained, this home offers both comfort and functionality. Inside, you'll love the cheerful white kitchen with granite counters and backsplash, flowing seamlessly into the open living and

  Sunnie San Lorenzo KeyIsle Realty

  251 Pelican Ln, Big Pine Key, FL 33043
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  /41

  $689,000 Sold Jun 27, 2025

  29873 Journeys End Rd, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,184 Sq Ft
  • Built 1991

  Last Sold Summary

  • 5% Below List Price
  • $582/SF
  • 104 Days On Market

  Current Estimated Value $695,773

  Last Listing Agent Heather Bennett Keller Williams Key West Compass Realty

  29873 Journeys End Rd, Big Pine Key, FL 33043
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  /23

  Est $797,061 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,364 Sq Ft

  27225 Mariposa Rd, Summerland Key, FL 33042

  27225 Mariposa Rd, Summerland Key, FL 33042
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  /2

  $52,000

  • Land

  0 Bk 2 Lt 24 Windward Beach Estate Unit 615586, Little Torch Key, FL 33042

  ROGO lot worth 2 points for DEDICATION purposes. Seller has county ROGO Letter of Land Dedication verifying lot is eligible for land dedication/2 points. Want to build quicker? This is a path. Buyer to verify points and process with Monroe County. See Documents tab for letter.

  Donna Pezzi Keller Williams Key West Compass Realty

  0 Bk 2 Lt 24 Windward Beach Estate Unit 615586, Little Torch Key, FL 33042
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  /48

  $975,000 Sold Jan 21, 2025

  22940 Gasparilla Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,465 Sq Ft
  • Built 1986

  Last Sold Summary

  • 5% Below List Price
  • $666/SF
  • 50 Days On Market

  Current Estimated Value $943,041

  Last Listing Agent Bobby Krug Ocean Sotheby's International Realty

  22940 Gasparilla Ln, Summerland Key, FL 33042
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  /2

  Est $788,219 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,300 Sq Ft

  27087 Angelfish Rd, Summerland Key, FL 33042

  27087 Angelfish Rd, Summerland Key, FL 33042
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  /7

  $195,000

  • Land
  • 1.02 Acres
  • $191,177 per Acre

  0 Lot 15 Blk 2 Rd Unit 613920, Sugarloaf Key, FL 33042

  Build your dream home. Imagine waking up to the natural beauty of the Florida Keys on this 44,431sqft lot. It is a special lot that features mature trees. Near Sugarloaf School. 25 minutes to Key West.

  Elizabeth Greco-DeGrenier Florida Keys Realty, Inc.

  0 Lot 15 Blk 2 Rd Unit 613920, Sugarloaf Key, FL 33042
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  /3

  $49,000 Sold Jun 06, 2025

  Lot 24 Vacant Land, Big Torch Key, FL 33042

  • Land

  Last Sold Summary

  • 35% Below List Price
  • 206 Days On Market

  Last Listing Agent Pamela Stangler Expert Realty LLC

  Lot 24 Vacant Land, Big Torch Key, FL 33042
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  /69

  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 420 Sq Ft

  701 Spanish Main Dr Unit 554, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 554, Cudjoe Key, FL 33042
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  /19

  $145,000 Pending

  • Land

  BK 7 LT 5 Coral Way, Big Pine Key, FL 33043

  Just four lots in from the open water, this spacious and partially cleared Tier II Lot is nestled within one of the most private blocks in the desirable and serene Doctor's Arm neighborhood of Big Pine Key - in the heart of Key Deer territory, surrounded by nature. This 5,750 Sq. Ft. with 50 ft of waterfrontage is on a clear flowthrough canal. Short distance to No Name Pub. This lot has not yet

  Vanessa J Chamizo Coldwell Banker Schmitt Islamorada

  BK 7 LT 5 Coral Way, Big Pine Key, FL 33043
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  /40

  $950,000 Sold Sep 17, 2025

  17126 Wahoo Ln W, Sugarloaf Shores, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1977

  Last Sold Summary

  • 16% Below List Price
  • $825/SF
  • 85 Days On Market

  Current Estimated Value $999,533

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  17126 Wahoo Ln W, Sugarloaf Shores, FL 33042
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  /14

  Est $589,000 Not Listed For Sale

  29167 Cactus Ln, Big Pine Key, FL 33043

  29167 Cactus Ln, Big Pine Key, FL 33043
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  /15

  $1,450,000

  • Land
  • 2.29 Acres
  • $633,190 per Acre

  1261 Avenue A, Big Pine Key, FL 33043

  An ultra rare opportunity awaits on Big Pine Key. Spanning 2.29 acres with bay bottom and one-of-a-kind 35 by 70 foot saltwater tide pool, this remarkable parcel showcases panoramic open water views across Bogie Channel. A true sanctuary of privacy and natural beauty, the property sits at the end of a quiet street beside a peaceful County park, bordered further by County owned land to the west

  Ally Kelley Ocean Sotheby's International

  1261 Avenue A, Big Pine Key, FL 33043
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  /48

  $940,000 Sold Feb 28, 2025

  184 Cutthroat Dr, Summerland Key, FL 33042

  • 6 Beds
  • 3 Baths
  • 2,320 Sq Ft
  • Built 1963

  Last Sold Summary

  • 22% Below List Price
  • $405/SF
  • 184 Days On Market

  Current Estimated Value $1,040,966

  Last Listing Agent Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

  184 Cutthroat Dr, Summerland Key, FL 33042
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  /2

  Est $562,000 Not Listed For Sale

  • Studio

  Lot 2 Egret Ln, Big Pine Key, FL 33043

  Lot 2 Egret Ln, Big Pine Key, FL 33043
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  /11

  $249,000 New Construction

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

  231 Pelican Ln, Big Pine Key, FL 33043

  The price is for the lot AND permit. Pre-construction showing a picture of the modular that is permitted. Make your changes now before price increases with work conducted OR purchase the property with the permit and finish it on your own. *Approved ROGO Allocation and Active Building Permit as of February 25, 2025. Building permit is ready to be picked up. Permit number: SFDUP-2023-0113 is

  Donna Pezzi Keller Williams Key West Compass Realty

  231 Pelican Ln, Big Pine Key, FL 33043
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  /44

  $853,000 Sold Aug 12, 2025

  873 Indies Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,081 Sq Ft
  • Built 2002

  Last Sold Summary

  • 10% Below List Price
  • $789/SF
  • 123 Days On Market

  Current Estimated Value $851,012

  Last Listing Agent Donna Halstead Coldwell Banker Schmitt RE Co.

  873 Indies Rd, Summerland Key, FL 33042
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  /11

  Est $291,539 Not Listed For Sale

  Lot 3 Egret Ln, Big Pine Key, FL 33043

  Lot 3 Egret Ln, Big Pine Key, FL 33043
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  /24

  $265,000

  • Land

  701 Spanish Main Dr Unit 69, Cudjoe Key, FL 33042

  RV Lot or Build your home here in the private, gated community of Venture Out on Cudjoe Key. 35' x 69' paved and cleared lot. Nightly rentals allowed here! Many amenities on-site including a boat ramp, marina store and fuel station. Basketball, bocce, tennis and pickleball courts. Heated saltwater swimming pool right by the ocean. Venture Out is a golf cart friendly community. There are always

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 69, Cudjoe Key, FL 33042
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  /29

  $510,000 Sold Apr 28, 2025

  1693 Bayview Dr, Little Torch Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 917 Sq Ft
  • Built 1976

  Last Sold Summary

  • 13% Below List Price
  • $556/SF
  • 60 Days On Market

  Last Listing Agent Ana Tey-Guerra Trexy International Realty, Inc

  1693 Bayview Dr, Little Torch Key, FL 33042
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  /66

  Not Listed For Sale

  • 2 Beds

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

  701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042
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  /24

  $385,000

  • Land

  701 Spanish Main Dr Unit 181, Cudjoe Key, FL 33042

  The Ultimate Canal-Front RV Oasis in Venture Out at Cudjoe KeyEscape to your own slice of paradise with this prime waterfront RV lot in the sought-after, gated community of Venture Out on Cudjoe Key. This lot is built for the avid water enthusiast and provides a perfect base for exploring the best of the Lower and Middle Florida Keys.Fully Prepped RV Pad: Bring your rig and start relaxing

  Carmen Brake Waterfront Keys Realty Inc.

  701 Spanish Main Dr Unit 181, Cudjoe Key, FL 33042
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  /45

  $819,000 Sold May 19, 2025

  25093 Center St, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,584 Sq Ft
  • Built 1958

  Last Sold Summary

  • 2% Below List Price
  • $517/SF
  • 18 Days On Market

  Current Estimated Value $841,755

  Last Listing Agent Susan Hawkinson Bascom Grooms Real Estate (KW)

  25093 Center St, Summerland Key, FL 33042
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  /2

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  701 Spanish Main Dr Unit 559, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 559, Cudjoe Key, FL 33042
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  $2,300,000 New Construction

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

  30995 Watson Blvd, Big Pine Key, FL 33043

  FINISHED -- NEW CONSTRUCTION!!! Luxury water view home with an in-ground pool on a 14,680 sq ft lot with dock and boating access. Brand new single level elevated CBS home over parking. Impact windows and doors, metal roof, 10-foot interior ceilings, stainless appliances and much more. Construction is completed, ready for occupancy.The property has a beautiful view over the water and a magnificent

  Banks Prevatt Coldwell Banker Schmitt RE Co.

  30995 Watson Blvd, Big Pine Key, FL 33043
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  /2

  $500,000 Sold Jun 27, 2025

  538 Powell Ave, Summerland Key, FL 33042

  • 2 Beds
  • 1.5 Baths
  • 912 Sq Ft
  • Built 1987

  Last Sold Summary

  • 17% Below List Price
  • $548/SF
  • 62 Days On Market

  Current Estimated Value $560,946

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  538 Powell Ave, Summerland Key, FL 33042
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  /2

  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 520 Sq Ft

  701 Spanish Main Dr Unit 537, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 537, Cudjoe Key, FL 33042
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  /68

  $1,895,000

  • 3 Beds
  • 3.5 Baths
  • 2,295 Sq Ft

  1136 W Shore Dr, Big Pine Key, FL 33043

  Not a drive by- Must see inside and the back yard too.....Located on the West Side of the Island with excellent boating access this beautiful pool home is an entertainer's dream place. Stunning Sunsets & Sparkling waters for swimming, snorkeling, paddleboarding. Home features 3 bedroom suites with full baths plus a powder room too. Impact doors and windows, tile floors throughout, Viking

  Beata Sharpe Coldwell Banker Vanguard Realty

  1136 W Shore Dr, Big Pine Key, FL 33043
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  /35

  $629,500 Sold Sep 30, 2025

  31463 Avenue A, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • Built 2007

  Last Sold Summary

  • 3% Below List Price
  • $484/SF
  • 24 Days On Market

  Last Listing Agent Ryan Gernaat Coldwell Banker Schmitt Lower Keys (KW)

  31463 Avenue A, Big Pine Key, FL 33043
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  /2

  Est $260,473 Not Listed For Sale

  • Studio

  281 Pelican Ln, Big Pine Key, FL 33043

  281 Pelican Ln, Big Pine Key, FL 33043
• 

  

  /40

  $2,450,000

  • 3 Beds
  • 2 Baths
  • 1,624 Sq Ft

  1330 Sugarloaf Blvd, Summerland Key, FL 33042

  Luxury Waterfront Living on Sugarloaf KeyExperience the epitome of island elegance in this beautifully completely renovated waterfront retreat on desirable Sugarloaf Key. This three-bedroom, two-bath home evething is brand NEW home showcases high-end finishes throughout, blending modern luxury with laid-back coastal charm. The open-concept living area flows seamlessly onto an expansive outdoor

  Brenda Donnelly Brenda Donnelly Real Estate LLC

  1330 Sugarloaf Blvd, Summerland Key, FL 33042
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  /34

  $580,000 Sold Sep 15, 2025

  30868 Malaga Ln, Big Pine Key, FL 33043

  • 3 Beds
  • 1 Bath
  • 1,080 Sq Ft
  • Built 1972

  Last Sold Summary

  • 3% Below List Price
  • $537/SF
  • 137 Days On Market

  Current Estimated Value $601,282

  Last Listing Agent Loren Rea Truman & Co. (KW)

  30868 Malaga Ln, Big Pine Key, FL 33043

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