Summerland Key, FL Homes

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  /38

  $700,000 Sold Sep 30, 2025

  31480 Avenue G, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 912 Sq Ft
  • Built 2001

  Last Sold Summary

  • 10% Below List Price
  • $768/SF
  • 179 Days On Market

  Current Estimated Value $720,867

  Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

  31480 Avenue G, Big Pine Key, FL 33043
• 

  

  

  /27

  Est $1,853,054 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,406 Sq Ft

  22836 Port Royal Ln, Summerland Key, FL 33042

  22836 Port Royal Ln, Summerland Key, FL 33042
• 

  

  

  /15

  $644,500

  • Land

  132 Sugarloaf Dr, Summerland Key, FL 33042

  Looking for your ROGO exempt slice of paradise. Look no further, build your dream home now. Large lush private lot. access from two streets to drive through. ROGO Exempt letter in hand, no waiting!! Community Marina and Ramp across the road.Great boating access to both Gulf and Atlantic. This beautiful lot awaits you to build your dream home. There is plenty space for Pool, storage, garage,

  Heather Mason Coastal Collection Real Estate Inc.

  132 Sugarloaf Dr, Summerland Key, FL 33042
• 

  

  

  /50

  $1,599,000 Sold Jun 10, 2025

  29655 Forrestal Ave, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,932 Sq Ft
  • Built 1990

  Last Sold Summary

  • 6% Below List Price
  • $828/SF
  • 42 Days On Market

  Current Estimated Value $1,599,401

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

  29655 Forrestal Ave, Big Pine Key, FL 33043
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  /37

  Est $1,019,508 Not Listed For Sale

  • 2 Beds
  • 3 Baths
  • 1,535 Sq Ft

  81 Coral Ave, Summerland Key, FL 33042

  81 Coral Ave, Summerland Key, FL 33042
• 

  

  /18

  $600,000

  • Land

  701 Spanish Main Dr Unit 384, Cudjoe Key, FL 33042

  Experience the ultimate in oceanfront living with this fantastic lot in a pristine gated community. Boasting a 53' concrete seawall and deep water access, this property is a boater's dream. The lot is RV-ready. It's also buildable, free from ROGO restrictions, and has a successful history as a vacation rental. Venture Out at Cudjoe Cay is a distinguished residential condominium community that

  The Spottswood Team Truman & Co. (KW)

  701 Spanish Main Dr Unit 384, Cudjoe Key, FL 33042
• 

  

  /44

  $695,000 Sold Mar 28, 2025

  29135 Camellia Ln, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,238 Sq Ft
  • Built 1988

  Last Sold Summary

  • 1% Below List Price
  • $561/SF
  • 3 Days On Market

  Current Estimated Value $709,566

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

  29135 Camellia Ln, Big Pine Key, FL 33043
• 

  

  /34

  Est $773,314 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 841 Sq Ft

  28551 Buccaneer Rd, Summerland Key, FL 33042

  28551 Buccaneer Rd, Summerland Key, FL 33042
• 

  

  /100

  $9,950,000

  • 6 Beds
  • 5 Baths
  • 5,208 Sq Ft

  16750 Old State Road 4a, Summerland Key, FL 33042

  Introducing Blue Water Lagoon Estate! Experience unmatched privacy and exceptional waterfront living at this gated 2.33-acre oceanfront estate in exclusive Sugarloaf Beach -- a location famously featured in the film ''True Lies''. Designed for the avid boater and those seeking a resort-style lifestyle, this 5,208 sq. ft. residence offers rare amenities and direct access to world-class fishing and

  Lisa Swanson The Agency Florida Keys

  16750 Old State Road 4a, Summerland Key, FL 33042
• 

  

  /54

  $615,000 Sold Jul 11, 2025

  701 Spanish Main Dr Unit 131, Cudjoe Key, FL 33042

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

  Last Sold Summary

  • 14% Below List Price
  • $712/SF
  • 194 Days On Market

  Last Listing Agent Jan Fritz Coldwell Banker Schmitt RE Co.

  701 Spanish Main Dr Unit 131, Cudjoe Key, FL 33042
• 

  

  /43

  Est $1,181,042 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,184 Sq Ft

  17055 Kingfish Ln W, Summerland Key, FL 33042

  17055 Kingfish Ln W, Summerland Key, FL 33042
• 

  

  /16

  $775,000

  • Land

  28597 Peg Leg Rd, Little Torch Key, FL 33042

  Vacant Land on Canal waiting on permit 41.5 points today for a 3809 sq.foot house with a roof top area. Permit number# SFDUP -2025-0096 Four-bedroom four-bathroom house. Builder will build for the buyer price and terms to be negotiated Dock and plans are included. Ranked for next quarter to be delivered a permit. Pictures shown as built house. Open Water View. House Permit SF-DUP-2025-0111, 41.5

  Barbara Eads Barbara Eads Realty

  28597 Peg Leg Rd, Little Torch Key, FL 33042
• 

  

  /31

  $650,000 Sold Apr 23, 2025

  30620 18th Ln, Big Pine Key, FL 33043

  • 2 Beds
  • 1 Bath
  • 1,120 Sq Ft
  • Built 1982

  Last Sold Summary

  • $580/SF
  • 3 Days On Market

  Current Estimated Value $664,576

  Last Listing Agent Christopher Tanaka Coldwell Banker Schmitt RE Co.

  30620 18th Ln, Big Pine Key, FL 33043
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  /50

  Est $950,342 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,224 Sq Ft

  17396 Jamaica Ln, Summerland Key, FL 33042

  17396 Jamaica Ln, Summerland Key, FL 33042
• 

  

  /57

  $959,000

  • 2 Beds
  • 2 Baths
  • 1,185 Sq Ft

  2123 Spanish Channel Dr, Big Pine Key, FL 33043

  Ocean Views, Direct canal frontage , in the ocean water in 2 minutes. Concrete Dock, Solid pour concrete column house is ready for making your own . Beautiful trees, planted newly landscaped with custom design fencing. Wildlife is amazing, quiet location near end of the road. Grocery store 1 mile away close to Key West or Marathon Roof replaced in 2018 also all new hurricane window, doors,

  Anne Press Lokation Real Estate

  2123 Spanish Channel Dr, Big Pine Key, FL 33043
• 

  

  /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 $639,121

  Last Listing Agent Sandra Rodriguez Lokation Real Estate

  31148 Avenue C, Big Pine Key, FL 33043
• 

  

  /40

  Est $1,049,862 Not Listed For Sale

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

  22983 Anne Bonny Ln, Summerland Key, FL 33042

  22983 Anne Bonny Ln, Summerland Key, FL 33042
• 

  

  /41

  $665,000

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

  29313 Coconut Palm Dr, Big Pine Key, FL 33043

  Welcome to this beautifully maintained home that offers comfort, convenience, and the quintessential Keys lifestyle. Equipped with impact windows and doors, a durable metal roof, plantation shutters, and low insurance rates, this home provides peace of mind and enduring value. The newly renovated kitchen is bathed in natural light and thoughtfully designed to cater to both everyday living and

  Scott Brisson KeyIsle Realty

  29313 Coconut Palm Dr, Big Pine Key, FL 33043
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  /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

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

  164 Tortuga Ln, Summerland Key, FL 33042
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  /6

  Est $647,420 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,144 Sq Ft

  79 Coral Ave, Summerland Key, FL 33042

  79 Coral Ave, Summerland Key, FL 33042
• 

  

  /19

  $465,000

  • Land

  701 Spanish Main Dr Unit 551, Cudjoe Key, FL 33042

  Prime RV lot offering a 35' concrete seawall with quick boating access and plenty of outdoor comfort. A concrete pad, dock box, and fish cleaning station make it easy to enjoy life on the water, while the natural shade keeps things cool and inviting. This active RV rental lot is ideal for investment income, retirement living, or an active Keys lifestyle. Located in the desirable, gated community

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 551, Cudjoe Key, FL 33042
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  /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 $592,352

  Last Listing Agent Ryan Call REALTY ZOOM

  3767 Hibiscus St, Big Pine Key, FL 33043
• 

  /2

  Est $2,415,418 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,000 Sq Ft

  20820 7th Ave W, Summerland Key, FL 33042

  20820 7th Ave W, Summerland Key, FL 33042
• 

  

  /45

  $1,775,000

  • 3 Beds
  • 2 Baths
  • 1,460 Sq Ft

  31253 Hibiscus Dr, Big Pine Key, FL 33043

  Experience the quintessential Florida Keys waterfront lifestyle from this open-water, 3-bedroom, 2-bathroom concrete home nestled along Big Pine Key's scenic Bogie Channel. This property boasts exceptional boating amenities, including two dedicated boat lifts and a convenient boat basin, ensuring effortless access to your vessels. Enjoy swift journeys, reaching the Atlantic in just two minutes or

  Lara Hanousek Platinum Purpose Real Estate, LLC

  31253 Hibiscus Dr, Big Pine Key, FL 33043
• 

  

  /44

  $876,000 Sold Apr 29, 2025

  30751 Palm Dr, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,724 Sq Ft
  • Built 1990

  Last Sold Summary

  • 6% Below List Price
  • $508/SF
  • 156 Days On Market

  Current Estimated Value $960,057

  Last Listing Agent Melissa Graham Bluescape Real Estate

  30751 Palm Dr, Big Pine Key, FL 33043
• 

  

  /48

  Est $983,414 Not Listed For Sale

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

  27342 Anguila Ln, Summerland Key, FL 33042

  27342 Anguila Ln, Summerland Key, FL 33042
• 

  

  /39

  $975,000

  • 2 Beds
  • 3 Baths
  • 1,120 Sq Ft

  421 Ixora Dr, Big Pine Key, FL 33043

  Beautifully maintained elevated Florida Keys home offering 2 bedrooms and 2 bathrooms upstairs plus a legal bathroom downstairs. This thoughtfully designed residence sits on a spacious 10,568 sq. ft. lot with ample parking for an RV and/or boat trailer and features quality construction throughout. Home was completely remodeled post Irma down to the studs. The interior showcases porcelain

  Melissa Graham Bluescape Real Estate

  421 Ixora Dr, Big Pine Key, FL 33043
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  /41

  $1,375,000 Sold Mar 13, 2025

  20785 5th Ave W, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,499 Sq Ft
  • Built 1990

  Last Sold Summary

  • 8% Below List Price
  • $917/SF
  • 77 Days On Market

  Current Estimated Value $1,395,438

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

  20785 5th Ave W, Summerland Key, FL 33042
• 

  

  /30

  Est $2,232,559 Not Listed For Sale

  • 6 Beds
  • 3 Baths
  • 3,000 Sq Ft

  17082 Starfish Ln W, Summerland Key, FL 33042

  17082 Starfish Ln W, Summerland Key, FL 33042
• 

  

  /57

  $1,900,000

  • 4 Beds
  • 3 Baths
  • 1,964 Sq Ft

  27385 Saint Lucie Ln, Summerland Key, FL 33042

  Tropical Keys Oasis -- Waterfront Luxury LivingCome experience this one-of-a-kind tropical oasis that feels like living at a Keys resort. Surrounded by lush landscaping, vibrant grass is the backdrop for nine coconut palms, five banana trees, two mango trees, and an avocado tree, this property bursts with natural beauty. Vibrant bougainvillea archways create a stunning entry to one of the most

  Amedeo Belmonte William Ravies Florida LLC

  27385 Saint Lucie Ln, Summerland Key, FL 33042
• 

  

  /40

  $680,000 Sold Mar 20, 2025

  27337 Tobago Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,080 Sq Ft
  • Built 1958

  Last Sold Summary

  • 1% Above List Price
  • $630/SF
  • 7 Days On Market

  Current Estimated Value $726,533

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

  27337 Tobago Ln, Summerland Key, FL 33042
• 

  /2

  Est $1,034,923 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,218 Sq Ft

  17174 Kingfish Ln W, Summerland Key, FL 33042

  17174 Kingfish Ln W, Summerland Key, FL 33042
• 

  

  /21

  $475,000

  • 1 Bed
  • 1 Bath
  • 668 Sq Ft

  701 Spanish Main Dr Unit 246, Cudjoe Key, FL 33042

  Ocean-View Retreat in Gated Waterfront Community on Cudjoe Key!NIGHTLY RENTALS ALLOWEDWelcome to your slice of paradise in the heart of the Florida Keys. This well-maintained 1-bedroom, 1-bathroom waterfront home is located inside the highly desirable, gated community of Venture Out, offering ocean views, direct boating access, and a plethora of amenities just steps away.The home features

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 246, Cudjoe Key, FL 33042
• 

  

  /107

  $5,300,000 Sold Jun 13, 2025

  220 E Caribbean Dr, Summerland Key, FL 33042

  • 5 Beds
  • 7 Baths
  • 4,981 Sq Ft
  • Built 2025

  Last Sold Summary

  • 18% Below List Price
  • $1,064/SF
  • 165 Days On Market

  Current Estimated Value $5,015,474

  Last Listing Agent Stacy Shahan Island Real Estate Company Florida Keys

  220 E Caribbean Dr, Summerland Key, FL 33042
• 

  

  /50

  Est $1,910,301 Not Listed For Sale

  • 6 Beds
  • 3.5 Baths
  • 4,060 Sq Ft

  21025 Hamilton Ave, Summerland Key, FL 33042

  21025 Hamilton Ave, Summerland Key, FL 33042
• 

  

  /9

  $849,000

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft

  22920 Privateer Dr, Summerland Key, FL 33042

  Mariner's Dream - Your Waterfront Paradise Awaits! Welcome to this elevated, stilted two-story home offering 1,560 SqFt of living space and a versatile 4th bedroom that doubles as a den. Situated on a deep, wide, and pristine canal in the desirable Cutthroat Harbor Estates of Cudjoe Key, this home provides the perfect canvas for renovation. With new windows and siding (Completed 2023), much of

  Robin Nilsson Keller Williams Key West Compass Realty

  22920 Privateer Dr, Summerland Key, FL 33042
• 

  /2

  $1,650,000 Sold Sep 03, 2025

  743 E Shore Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,747 Sq Ft
  • Built 1991

  Last Sold Summary

  • 6% Below List Price
  • $944/SF
  • 1 Day On Market

  Current Estimated Value $1,682,059

  Last Listing Agent Scott Brisson KeyIsle Realty

  743 E Shore Dr, Summerland Key, FL 33042
• 

  /2

  Est $969,348 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft

  152 Sugarloaf Dr, Summerland Key, FL 33042

  152 Sugarloaf Dr, 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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  /49

  $995,000 Sold Dec 23, 2025

  29462 Geraldine St, Big Pine Key, FL 33043

  • 3 Beds
  • 3 Baths
  • 2,240 Sq Ft
  • Built 1991

  Last Sold Summary

  • 9% Below List Price
  • $444/SF
  • 65 Days On Market

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  29462 Geraldine St, Big Pine Key, FL 33043

Showing Results 601 - 640, Page 16 of 18