Summerland Key, FL Homes

• 

  

  

  /30

  Est $605,945 Not Listed For Sale

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

  19506 Seminole St, Summerland Key, FL 33042

  19506 Seminole St, Summerland Key, FL 33042
• 

  

  

  /23

  $1,595,000

  • 3 Beds
  • 3 Baths
  • 2,022 Sq Ft

  887 Bay Dr, Summerland Key, FL 33042

  This 3-bedroom, 3-bath concrete fortress on a deep water canal (5' draft) is located in the highly sought-after Summerland Cove with quick access to both the Gulf and Atlantic--just a 15-minute boat ride to open ocean--this home is a true boater's paradise. Additionally, enjoy Airstrip rights as part of the Summerland Airport community. Set on a generous 75' x 100' corner lot, the property offers

  Amy Hanson Realty Executives Florida Keys Summerland Branch

  887 Bay Dr, Summerland Key, FL 33042
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  /2

  $49,000 Sold Jun 06, 2025

  7 Lot, Lower Keys, FL 33042

  • Land
  • 0.19 Acre
  • $257,895 per Acre

  Last Sold Summary

  • 12% Below List Price
  • 168 Days On Market

  Last Listing Agent Pamela Stangler MMLS Assoc.-Inactive Member

  7 Lot, Lower Keys, FL 33042
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  /9

  Est $680,226 Not Listed For Sale

  • 2 Beds

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

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

  

  

  /96

  $1,698,000

  • 4 Beds
  • 3 Baths
  • 2,353 Sq Ft

  17176 Bonita Ln W, Summerland Key, FL 33042

  ***Open House Saturday, February 7th from 1-3Experience island living in this 2,353 sq ft, 4-bed, 3-bath Sugarloaf Shores home on a 12,500 sq ft lot. The split-level design includes two ensuite bedrooms with balcony access, plus two guest rooms on the ground floor. Skylights brighten the open living areas, flowing seamlessly to a 44' screened balcony.Out back, enjoy a 22' x 10' pool, gazebo,

  Tom Mclaughlin Coldwell Banker Schmitt Real Estate Co. (KW)

  17176 Bonita Ln W, Summerland Key, FL 33042
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  /30

  $400,000 Sold Apr 15, 2025

  115 E Cahill Ct, Big Pine Key, FL 33043

  • 2 Beds
  • 1 Bath
  • 972 Sq Ft
  • Built 1976

  Last Sold Summary

  • 11% Below List Price
  • $412/SF
  • 25 Days On Market

  Current Estimated Value $453,235

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

  115 E Cahill Ct, Big Pine Key, FL 33043
• 

  

  /15

  Est $811,927 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,134 Sq Ft

  16991 Shore Dr, Summerland Key, FL 33042

  16991 Shore Dr, Summerland Key, FL 33042
• 

  

  /30

  $485,000

  • 2 Beds
  • 1.5 Baths
  • 604 Sq Ft

  701 Spanish Main Dr Unit 234, Cudjoe Key, FL 33042

  Beautifully updated 2-bedroom, 1.5-bath canal-front home in Venture Out, offering move-in-ready comfort and a true taste of the Keys lifestyle. Step inside this bright and inviting space featuring a sliding pocket door that allows for a private entrance, new A/C, a newly sealed roof, and nearly all new windows. The home was completely gutted and rebuilt in 2016 with 2x4 walls, full insulation,

  Jenifer Hirsch Bluescape Real Estate

  701 Spanish Main Dr Unit 234, Cudjoe Key, FL 33042
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  /28

  $510,500 Sold Aug 14, 2025

  31124 Avenue E, Big Pine Key, FL 33043

  • 2 Beds
  • 1 Bath
  • 912 Sq Ft
  • Built 1963

  Last Sold Summary

  • 3% Below List Price
  • $560/SF
  • 17 Days On Market

  Current Estimated Value $513,632

  Last Listing Agent Derrick Johnson Coco Plum Real Estate

  31124 Avenue E, Big Pine Key, FL 33043
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  /56

  Est $1,784,236 Not Listed For Sale

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

  20966 8th Ave W, Summerland Key, FL 33042

  20966 8th Ave W, Summerland Key, FL 33042
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  /3

  $179,000 Pending

  • Land
  • 0.11 Acre
  • $1,627,273 per Acre

  Lot 32 Caloosa St, Sugarloaf, FL 33042

  Lot with ROGO letter for 5 points. Not ROGO exempt, use points towards building on another lot or contact the Monroe County Planning Department for information about building on this lot or how to use these points. Tier 3 AE11. Contact Monroe County to verify all information. ROGO letter available upon request.

  Pamela Stangler MMLS Assoc.-Inactive Member

  Lot 32 Caloosa St, Sugarloaf, FL 33042
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  /28

  $853,000 Sold Jan 09, 2026

  22922 Blackbeard Ln, Cudjoe Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,195 Sq Ft
  • Built 2012

  Last Sold Summary

  • 14% Below List Price
  • $714/SF
  • 105 Days On Market

  Last Listing Agent Krystal Thomas eXp Realty LLC

  22922 Blackbeard Ln, Cudjoe Key, FL 33042
• 

  

  /21

  Est $784,009 Not Listed For Sale

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

  19570 Mayan St, Summerland Key, FL 33042

  19570 Mayan St, Summerland Key, FL 33042
• 

  

  /10

  $100,000 Pending

  • Land

  BK 24 LT 2 Pandorea Ln, Big Pine Key, FL 33043

  Discover this spacious waterfront corner Tier II Lot nestled in Eden Pines Colony. This lot has not yet entered the ROGO systems but is buildable and modulars are allowed.The sale of the property is subject to letters of administration/approval of the probate court.

  Vanessa J Chamizo Coldwell Banker Schmitt Islamorada

  BK 24 LT 2 Pandorea Ln, Big Pine Key, FL 33043
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  /62

  $1,185,000 Sold Oct 06, 2025

  22915 Bluegill Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 2001

  Last Sold Summary

  • 6% Below List Price
  • $882/SF
  • 37 Days On Market

  Current Estimated Value $1,181,064

  Last Listing Agent Deni Heintzelman KeyIsle Realty

  22915 Bluegill Ln, Summerland Key, FL 33042
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  /73

  Est $1,060,649 Not Listed For Sale

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

  103 Shore Dr, Summerland Key, FL 33042

  103 Shore Dr, Summerland Key, FL 33042
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  /9

  $185,000 Under Contract

  • Land

  Vacant Picard Ln, Cudjoe Key, FL 33042

  Waterfront vacant lot waiting for you: Build your dream home here! Located in the highly desirable Cutthroat Harbor Estates neighborhood. This is a fantastic opportunity: apply for your permits to build your dream home, and complete it with a boat dock to enjoy the Florida Keys Lifestyle. This property is situated on a quiet street with only 2 homes to pass by, and you're boat will be in the open

  Sunnie San Lorenzo KeyIsle Realty

  Vacant Picard Ln, Cudjoe Key, FL 33042
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  /34

  $1,300,000 Sold Aug 18, 2025

  22822 John Silver Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 2,100 Sq Ft
  • Built 2002

  Last Sold Summary

  • 19% Below List Price
  • $619/SF
  • 214 Days On Market

  Current Estimated Value $1,318,755

  Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

  22822 John Silver Ln, Summerland Key, FL 33042
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  /36

  Est $974,538 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,245 Sq Ft

  21066 3rd Ave, Summerland Key, FL 33042

  21066 3rd Ave, Summerland Key, FL 33042
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  /11

  $650,000

  • Land

  775 Pirates Rd, Summerland Key, FL 33042

  Rare opportunity in Jolly Roger Estates on Little Torch Key. This 6,000 sq. ft. cleared and build-ready lot comes with two ROGO exemptions, allowing for immediate construction. The property features 60 feet of east-facing waterfront with a concrete dock, step-down, and davits already in place. Central sewer is connected. Located on a clean, deep canal (approx. 3 ft. control depth) with quick open

  Melissa Gibbins Expert Realty LLC (HQ)

  775 Pirates Rd, Summerland Key, FL 33042
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  /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 $746,796

  Last Listing Agent Ian Calderwood Bluescape Real Estate

  28009 Gulf Blvd, Big Pine Key, FL 33043
• 

  /2

  Est $1,796,434 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 3,579 Sq Ft

  17334 La Brisa Ln, Summerland Key, FL 33042

  17334 La Brisa Ln, Summerland Key, FL 33042
• 

  

  /23

  $730,000

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

  74 Pelican Ln, Big Pine Key, FL 33043

  Completely remodeled property with a new roof installed in 2024, new flooring, termite treatment completed in 2025, fully furnished, and ideally located just 30 minutes from Key West. It's close to restaurants, schools, beaches, recreational facilities, and everything you need for a peaceful and enjoyable life. It also features an additional, fully finished game room with a separate entrance. The

  Yunior Molina My Realty Group, LLC.

  74 Pelican Ln, Big Pine Key, FL 33043
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  /2

  $52,000 Sold Jun 30, 2025

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

  • Land
  • 0.27 Acre
  • $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
• 

  /2

  Est $1,352,511 Not Listed For Sale

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

  23047 Bluegill Ln, Summerland Key, FL 33042

  23047 Bluegill Ln, Summerland Key, FL 33042
• 

  

  /71

  $1,150,000

  • 3 Beds
  • 2 Baths
  • 1,068 Sq Ft

  19881 Date Palm Dr, Summerland Key, FL 33042

  Escape to your own private paradise at 19881 Date Palm Drive in Sugarloaf Key! This beautifully updated single-family home is tucked away in a quiet, secluded location and offers 100 feet of pristine canal frontage with a cut-in boat slip--perfect for boating enthusiasts with no neighbors across the canal!Step inside to find rich Brazilian hardwood floors, custom wood cabinetry, and sleek

  Jimmy Lane Island Life Realty Experts

  19881 Date Palm Dr, Summerland Key, FL 33042
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  /2

  $55,000 Sold Dec 04, 2025

  Lot 17 Treasure Chest Dr, Cudjoe Key, FL 33042

  • Land

  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
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  /49

  Est $1,803,224 Not Listed For Sale

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

  22766 Jolly Roger Dr, Summerland Key, FL 33042

  22766 Jolly Roger Dr, Summerland Key, FL 33042
• 

  

  /39

  $1,050,000

  • 3 Beds
  • 2 Baths
  • 2,198 Sq Ft

  21073 7th Ave, Summerland Key, FL 33042

  Florida Keys Waterfront Paradise - 80' Dock & No Bridges to Open Water!Nestled in a boater's paradise, this 2,198 sq. ft. 3-bed, 2-bath home offers a split floor plan for privacy and comfort. Inside, the spacious kitchen boasts stainless steel appliances, generous cabinet space, and ample corian counter space perfect for cooking up your fresh catch. The open-concept living and dining area flows

  Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

  21073 7th Ave, Summerland Key, FL 33042
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  /29

  $235,000 Sold Oct 31, 2025

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

  • Land

  Last Sold Summary

  • 2% Below List Price
  • 76 Days On Market

  Current Estimated Value $245,569

  Last Listing Agent Kelly Gardner Bluescape Real Estate

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

  

  /29

  Est $1,788,478 Not Listed For Sale

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

  17234 Green Turtle Ln E, Summerland Key, FL 33042

  17234 Green Turtle Ln E, Summerland Key, FL 33042
• 

  

  /73

  $810,000 Under Contract

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

  547 Heck Ave, Little Torch Key, FL 33042

  Stunning 3-Bed, 2-Bath Home in Little Torch Key – A Boater’s Paradise! Nestled in a peaceful neighborhood in sought-after Little Torch Key, this charming home is perfect for those who love boating and fishing. The bright, open-concept living area is ideal for entertaining, while the upstairs screened porch offers a fantastic spot for grilling and outdoor dining with elevated waterfront views. The

  Litney Ellis Dalton Wade Inc

  547 Heck Ave, Little Torch Key, FL 33042
• 

  /2

  $495,000 Sold Feb 25, 2025

  701 Spanish Main Dr Unit 440, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 773 Sq Ft
  • Built 1980

  Last Sold Summary

  • 8% Below List Price
  • $640/SF
  • 78 Days On Market

  Last Listing Agent Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 440, Cudjoe Key, FL 33042
• 

  /2

  Est $1,257,269 Not Listed For Sale

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

  19563 Canal Dr, Summerland Key, FL 33042

  19563 Canal Dr, Summerland Key, FL 33042
• 

  

  /41

  $2,395,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,577 Sq Ft

  1176 Thatch Ln, Summerland Key, FL 33042

  Unobstructed Ocean views, your own Private Oasis! On a canal with easy access to both the Ocean and Back Country. Whether you're seeking a full time residence, vacation getaway, or income-producing investment, this waterfront gem checks every box! Huge 24,829 Sqft LOT with plenty of room to add on. The home has consistent vacation rentals booked 4+ months out of the year, every year!! (income

  Jonathan Minerick Homecoin.com

  1176 Thatch Ln, Summerland 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
• 

  /2

  Est $872,000 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  154 Cutthroat Dr, Summerland Key, FL 33042

  154 Cutthroat Dr, Summerland Key, FL 33042
• 

  

  /42

  $2,200,000

  • 5 Beds
  • 3 Baths
  • 1,978 Sq Ft

  94 Sacarma Dr, Cudjoe Key, FL 33042

  Rare Licensed Oceanfront Short-Term Vacation Rental in the Lower Florida Keys. Welcome to Fandango, a highly successful transient (daily-weekly) vacation rental home offering an exceptional investment opportunity and a personal retreat. This stunning 5-bedroom, 3-bathroom property, built in 2011 and expanded in 2018, was thoughtfully designed as the ultimate family vacation rental retreat.

  Michelle Blades Realty Executives Florida Keys Old Town

  94 Sacarma Dr, 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 $1,018,365

  Last Listing Agent Brian Kruszewski LoKation Real Estate

  27330 Barbados Ln, Ramrod Key, FL 33042
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  /39

  Est $957,305 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,192 Sq Ft

  22716 Privateer Dr, Summerland Key, FL 33042

  22716 Privateer Dr, Summerland Key, FL 33042

Showing Results 641 - 680, Page 17 of 18