Summerland Key, FL Homes

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  /46

  $735,000

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  30920 Baileys Ln, Big Pine Key, FL 33043

  Discover the perfect blend of coastal living and convenience in this CBS-built home offering exceptional access to open water--just minutes to both the Gulf and the Atlantic. Situated on a spacious double lot, the property includes a 30 ft. Step down boat slip cut in, ideal for docking your boat and enjoying effortless days on the water.Designed for seamless indoor-outdoor living, the home

  Deni Heintzelman KeyIsle Realty

  30920 Baileys Ln, Big Pine Key, FL 33043
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  /42

  $930,000 Sold Nov 19, 2025

  29012 Bigonia Dr, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1993

  Last Sold Summary

  • 15% Below List Price
  • $881/SF
  • 92 Days On Market

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

  29012 Bigonia Dr, Big Pine Key, FL 33043
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  /15

  Est $195,583 Not Listed For Sale

  29859 Overseas Hwy Unit 54, Big Pine Key, FL 33043

  29859 Overseas Hwy Unit 54, Big Pine Key, FL 33043
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  /49

  $280,000 Open Sun 12PM - 2PM

  • 1 Bed
  • 1 Bath
  • 690 Sq Ft

  701 Spanish Main Dr Unit 21, Cudjoe Key, FL 33042

  Welcome to your slice of Paradise in the florida Keys! This cozy one bed/one bath mobile home is located in the highly desirable Venture Out gated community on Cudjoe Key. Thoughtfully designed and fully furnished, this home comfortably sleeps four and is in move-in ready. Enjoy the bright and inviting Florida room featuring durable Hardie board siding, along with a covered tile patio outback,

  Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 21, Cudjoe Key, FL 33042
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  /36

  $1,215,000 Sold Apr 09, 2025

  17246 Jamaica Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft
  • Built 2020

  Last Sold Summary

  • 12% Below List Price
  • $844/SF
  • 23 Days On Market

  Current Estimated Value $1,195,666

  Last Listing Agent Stephen Hachey

  17246 Jamaica Ln, Summerland Key, FL 33042
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  /2

  Est $761,844 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 880 Sq Ft

  549 Powell Ave, Summerland Key, FL 33042

  549 Powell Ave, Summerland Key, FL 33042
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  /7

  $4,325,000 Pending

  • 5 Beds
  • 5.5 Baths
  • 3,119 Sq Ft

  231 E Shore Dr Unit 7, Summerland Key, FL 33042

  Introducing Seven Palms Cove, a one-of-a-kind new construction community redefining luxury island living in the Florida Keys. With only seven exclusive oceanfront residences starting at $4M, this private, gated enclave offers an extraordinary opportunity to own a slice of paradise just minutes from Key West.Each home spans over 4,000 sq. ft. with 5 bedrooms, 5.5 bathrooms, and open-concept

  Stephanie Muzzillo Serhant Florida LLC - Delray Beach Office

  231 E Shore Dr Unit 7, Summerland Key, FL 33042
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  /37

  $725,000 Sold Jan 14, 2026

  27394 Saint Lucie Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,078 Sq Ft
  • Built 1994

  Last Sold Summary

  • $673/SF
  • 19 Days On Market

  Last Listing Agent Casey Arnold eXp Realty LLC

  27394 Saint Lucie Ln, Summerland Key, FL 33042
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  /21

  Est $668,307 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,566 Sq Ft

  31011 Avenue C, Big Pine Key, FL 33043

  31011 Avenue C, 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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  /47

  $945,000 Sold Oct 03, 2025

  29487 Ranger Ave, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,258 Sq Ft
  • Built 1996

  Last Sold Summary

  • 3% Below List Price
  • $751/SF
  • 99 Days On Market

  Current Estimated Value $983,438

  Last Listing Agent Melissa Gibbins Expert Realty LLC (HQ)

  29487 Ranger Ave, Big Pine Key, FL 33043
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  /28

  Est $882,476 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,176 Sq Ft

  30887 Ortega Ln, Big Pine Key, FL 33043

  30887 Ortega Ln, Big Pine Key, FL 33043
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  /41

  $749,000

  • 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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  /49

  $750,000 Sold Jul 24, 2025

  25121 Center St, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft
  • Built 2008

  Last Sold Summary

  • 14% Below List Price
  • $781/SF
  • 72 Days On Market

  Current Estimated Value $763,794

  Last Listing Agent Gregory Sullivan BYOWNER.COM

  25121 Center St, Summerland Key, FL 33042
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  /2

  Est $754,159 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 998 Sq Ft

  30827 Baileys Ln, Big Pine Key, FL 33043

  30827 Baileys Ln, Big Pine Key, FL 33043
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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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  /46

  $540,000 Sold May 19, 2025

  31130 Avenue I, Big Pine Key, FL 33043

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

  Last Sold Summary

  • 14% Below List Price
  • $562/SF
  • 36 Days On Market

  Current Estimated Value $1,863,908

  Last Listing Agent Michael Sielicki Jr Real Broker, LLC

  31130 Avenue I, Big Pine Key, FL 33043
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  /16

  Est $644,634 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 1,562 Sq Ft

  30323 Poinciana Rd, Big Pine Key, FL 33043

  30323 Poinciana Rd, Big Pine Key, FL 33043
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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 Coldwell Banker Schmitt RE Co.

  0 Lot 15 Blk 2 Rd Unit 613920, Sugarloaf Key, FL 33042
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  /21

  $642,500 Sold Feb 10, 2025

  19518 Caloosa St, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,143 Sq Ft
  • Built 1992

  Last Sold Summary

  • 8% Below List Price
  • $562/SF
  • 159 Days On Market

  Current Estimated Value $674,124

  Last Listing Agent Wendy Holifield Berkshire Hathaway HomeServices Knight & Gardner Realty

  19518 Caloosa St, Summerland Key, FL 33042
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  /2

  Est $4,062,761 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 4,030 Sq Ft

  1152 W Shore Dr, Big Pine Key, FL 33043

  1152 W Shore Dr, Big Pine Key, FL 33043
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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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  /45

  $710,000 Sold Feb 05, 2026

  27163 Mariposa Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,488 Sq Ft
  • Built 2018

  Last Sold Summary

  • 10% Below List Price
  • $477/SF
  • 238 Days On Market

  Last Listing Agent Jessica Roden Ocean Sotheby's International Realty

  27163 Mariposa Rd, Summerland Key, FL 33042
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  /42

  Est $1,200,936 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft

  29479 Ranger Ave, Big Pine Key, FL 33043

  29479 Ranger Ave, 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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  /100

  $3,300,000 Sold Dec 01, 2025

  815 E Shore Dr, Summerland Key, FL 33042

  • 7 Beds
  • 6 Baths
  • 4,531 Sq Ft
  • Built 1961

  Last Sold Summary

  • 26% Below List Price
  • $728/SF
  • 295 Days On Market

  Last Listing Agent Karen Williams-deCastro LPT Realty, LLC

  815 E Shore Dr, Summerland Key, FL 33042
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  /3

  Est $1,147,017 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 1,702 Sq Ft

  Unlisted Address

  Unlisted Address
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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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  /32

  $450,000 Sold Aug 20, 2025

  701 Spanish Main Dr Unit 22, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 814 Sq Ft
  • Built 2016

  Last Sold Summary

  • 9% Below List Price
  • $553/SF
  • 283 Days On Market

  Last Listing Agent Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 22, Cudjoe Key, FL 33042
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  /63

  Est $899,708 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,196 Sq Ft

  27322 Saint Martin Ln, Summerland Key, FL 33042

  27322 Saint Martin Ln, Summerland Key, FL 33042
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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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  /30

  $1,185,000 Sold Nov 17, 2025

  478 Blackbeard Rd, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,116 Sq Ft
  • Built 1980

  Last Sold Summary

  • 3% Below List Price
  • $1,062/SF
  • 0 Days On Market

  Last Listing Agent Jenny Perry Preferred Properties (KW)

  478 Blackbeard Rd, Summerland Key, FL 33042
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  /55

  Est $1,350,771 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,943 Sq Ft

  266 Colson Dr, Summerland Key, FL 33042

  266 Colson Dr, Summerland Key, FL 33042
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  /24

  $375,000

  • 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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  /36

  $330,000 Sold Apr 17, 2025

  701 Spanish Main Dr Unit 28, Cudjoe Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 728 Sq Ft
  • Built 1983

  Last Sold Summary

  • 8% Below List Price
  • $453/SF
  • 63 Days On Market

  Last Listing Agent Frank Griffiths Lokation Real Estate

  701 Spanish Main Dr Unit 28, Cudjoe Key, FL 33042
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  /37

  Est $1,708,758 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,920 Sq Ft

  1008 Buttonwood Dr E, Summerland Key, FL 33042

  1008 Buttonwood Dr E, Summerland Key, FL 33042
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  /32

  $1,150,000

  • 2 Beds
  • 2 Baths
  • 1,175 Sq Ft

  27821 Leeward South Rd, Little Torch Key, FL 33042

  ***OPEN HOUSE*** Saturday February 7th 10am - 12pm. Location Location Location! This property offers lots of space, tons of privacy and stunning views. This home is situated on 2.38 acres of land with breathtaking open water views. Walk on to your newly refinished composite stairs to a walk around porch. Making access to the exterior of the home super easy. Interior layout is a large open floor

  Tracy Shields KeyIsle Realty

  27821 Leeward South Rd, Little Torch Key, FL 33042
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  /27

  $730,000 Sold Mar 21, 2025

  27230 Brown Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,242 Sq Ft
  • Built 1996

  Last Sold Summary

  • 8% Below List Price
  • $588/SF
  • 102 Days On Market

  Current Estimated Value $781,718

  Last Listing Agent Amber DeBevec LoKation Real Estate

  27230 Brown Dr, Summerland Key, FL 33042
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  /43

  Est $2,884,777 Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 3,160 Sq Ft

  1619 Long Beach Dr, Big Pine Key, FL 33043

  1619 Long Beach Dr, Big Pine Key, FL 33043
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  /24

  $580,175

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  701 Spanish Main Dr Unit 79, Cudjoe Key, FL 33042

  Licensed Nightly Rental Property!! Discover island living at 701 Spanish Main Dr, Unit 79 in Cudjoe Key, FL. This charming property offers an unbeatable opportunity for investors or those seeking a tranquil retreat. Currently operating as a successful vacation rental, this home is perfectly positioned to generate income or serve as your own private oasis. This property promises both convenience

  Sarah Dolson Keller Williams Key West Compass Realty

  701 Spanish Main Dr Unit 79, Cudjoe Key, FL 33042

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