Summerland Key, FL Homes

• 

  

  

  /23

  Est $1,322,526 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,568 Sq Ft

  30891 Granada Ave, Big Pine Key, FL 33043

  30891 Granada Ave, Big Pine Key, FL 33043
• 

  

  

  /43

  $875,000

  • 2 Beds
  • 2 Baths
  • 912 Sq Ft

  681 W Indies Dr, Summerland Key, FL 33042

  This charming 2-bedroom, 2-bath home is your slice of paradise in the Lower Keys. Nestled on the open water, the property offers ocean views that will take your breath away. Enjoy your morning coffee or evening cocktails on the screened-in porch, perfect for relaxing and soaking in the coastal breeze. With a swim dock right out back, you'll have easy access to the crystal-clear waters for a quick

  Karen Haack Coldwell Banker Schmitt RE Co.

  681 W Indies Dr, Summerland Key, FL 33042
• 

  

  

  /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
• 

  

  

  /55

  Est $1,334,208 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,108 Sq Ft

  350 W Shore Dr, Summerland Key, FL 33042

  350 W Shore Dr, Summerland Key, FL 33042
• 

  

  

  /45

  $1,900,000 Pending

  • 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
• 

  

  /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
• 

  

  /28

  Est $1,210,677 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,244 Sq Ft

  2237 San Remo Dr, Big Pine Key, FL 33043

  2237 San Remo Dr, Big Pine Key, FL 33043
• 

  

  /39

  $999,000

  • 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
• 

  

  /27

  $225,000 Sold Jan 13, 2025

  701 Spanish Main Dr Unit 473, Cudjoe Key, FL 33042

  • Land

  Last Sold Summary

  • 13% Below List Price
  • 161 Days On Market

  Current Estimated Value $230,278

  Last Listing Agent Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 473, Cudjoe Key, FL 33042
• 

  /2

  Est $364,990 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,584 Sq Ft

  30869 Bay Shore Dr, Big Pine Key, FL 33043

  30869 Bay Shore Dr, Big Pine Key, FL 33043
• 

  

  /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
• 

  

  /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
• 

  

  /31

  Est $721,627 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft

  174 Newfound Blvd, Big Pine Key, FL 33043

  174 Newfound Blvd, Big Pine Key, FL 33043
• 

  

  /96

  $1,698,000

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

  17176 Bonita Ln W, Summerland Key, FL 33042

  Experience 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, private boat ramp, swim ladder, and dual lifts

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

  17176 Bonita Ln W, Summerland Key, FL 33042
• 

  

  /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
• 

  

  /64

  Est $1,654,406 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,801 Sq Ft

  553 Indies Rd, Summerland Key, FL 33042

  553 Indies Rd, Summerland Key, FL 33042
• 

  

  /40

  $1,149,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,654 Sq Ft

  32734 Bimini Ln, Big Pine Key, FL 33043

  Escape to quintessential No Name Key to find this waterfront sanctuary. No Name Key is a secluded paradise; free of commercial development with fewer than 50 homes nestled in a one-of-a-kind conservation setting. This location offers unmatched stargazing and serene surroundings--yet it's just over 10 minutes from the amenities of Big Pine Key, 45 minutes from Marathon and 1 hour from Key West.

  Ally Kelley Ocean Sotheby's International

  32734 Bimini Ln, Big Pine Key, FL 33043
• 

  

  /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 $771,636

  Last Listing Agent Amber DeBevec LoKation Real Estate

  27230 Brown Dr, Summerland Key, FL 33042
• 

  

  /49

  Est $1,167,777 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,344 Sq Ft

  403 Indies Rd, Ramrod Key, FL 33042

  403 Indies Rd, Ramrod Key, FL 33042
• 

  

  /64

  $3,199,000

  • 3 Beds
  • 2 Baths
  • 2,232 Sq Ft

  23941 Henry St, Summerland Key, FL 33042

  Oceanfront Luxury Retreat with Private Beach, Protected Dockage & Quick Direct Boating Access to both Ocean & Gulf.Wake up to breathtaking Atlantic sunrises and unwind with glowing sunsets in this custom 2-story 4,024 SF CBS oceanfront home, perfectly positioned on a private street with only four residences. Located on Summerland Key, this Island inspired escape offers panoramic ocean views,

  Stacy Shahan Island Real Estate Company Florida Keys

  23941 Henry St, Summerland Key, FL 33042
• 

  

  /45

  $799,000 Sold Aug 29, 2025

  17338 Dolphin St E, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,875 Sq Ft
  • Built 1963

  Last Sold Summary

  • 30% Below List Price
  • $426/SF
  • 171 Days On Market

  Current Estimated Value $857,668

  Last Listing Agent Alexa Morgan Buy The Keys

  17338 Dolphin St E, Summerland Key, FL 33042
• 

  

  /16

  Est $939,963 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,086 Sq Ft

  273 Indies Rd, Summerland Key, FL 33042

  273 Indies Rd, Summerland Key, FL 33042
• 

  

  /19

  $329,000

  • 2 Beds
  • 1 Bath
  • 756 Sq Ft

  701 Spanish Main Dr Unit 62, Cudjoe Key, FL 33042

  NIGHTLY RENTALS ALLOWED! Welcome to this immaculate 2-bedroom, 1-bathroom vacation retreat nestled at the picturesque southern tip of Venture Out, where the land gracefully meets the sea. The attention to detail is evident with luxurious travertine flooring added to this home. Don't let the square footage fool you. This home offers an open floor plan with an open kitchen over looking the family

  Susan Halligan Live Local Realty of the Florida Keys

  701 Spanish Main Dr Unit 62, Cudjoe Key, FL 33042
• 

  

  /9

  $350,000 Sold Jun 12, 2025

  31456 Ave F, Big Pine Key, FL 33043

  • Land

  Last Sold Summary

  • 7% Below List Price
  • 20 Days On Market

  Current Estimated Value $351,017

  Last Listing Agent Kirksten Irick Preferred Properties (KW)

  31456 Ave F, Big Pine Key, FL 33043
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  /62

  Est $4,726,764 Not Listed For Sale

  • 5 Beds
  • 5 Baths
  • 3,421 Sq Ft

  1141 Ocean Dr, Summerland Key, FL 33042

  1141 Ocean 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
• 

  

  /47

  $1,075,000 Sold Jul 30, 2025

  128 Le Grand Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 1999

  Last Sold Summary

  • 16% Below List Price
  • $960/SF
  • 189 Days On Market

  Current Estimated Value $1,077,753

  Last Listing Agent Alain Majeau Berkshire Hathaway HomeServices Knight & Gardner Realty

  128 Le Grand Ln, Summerland Key, FL 33042
• 

  

  /37

  Est $1,150,236 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,368 Sq Ft

  716 Caribbean Dr E, Summerland Key, FL 33042

  716 Caribbean Dr E, Summerland Key, FL 33042
• 

  

  /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
• 

  

  /22

  $500,000 Sold Jun 30, 2025

  31232 Ave d, Big Pine Key, FL 33043

  • 3 Beds
  • 1 Bath
  • 988 Sq Ft
  • Built 1958

  Last Sold Summary

  • 5% Below List Price
  • $506/SF
  • 41 Days On Market

  Current Estimated Value $516,995

  Last Listing Agent Rose Dell Keller Williams Key West Compass Realty

  31232 Ave d, Big Pine Key, FL 33043
• 

  

  /40

  Est $2,214,836 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,184 Sq Ft

  20995 2nd Ave W, Summerland Key, FL 33042

  20995 2nd Ave W, 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
• 

  

  /40

  $940,000 Sold Jun 02, 2025

  763 Diane Ave, Little Torch Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft
  • Built 2012

  Last Sold Summary

  • 6% Below List Price
  • $791/SF
  • 15 Days On Market

  Current Estimated Value $947,373

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

  763 Diane Ave, Little Torch Key, FL 33042
• 

  

  /49

  Est $6,954,565 Not Listed For Sale

  • 10 Beds
  • 11.5 Baths
  • 10,607 Sq Ft

  17279 Oleander Ln, Sugarloaf Key, FL 33042

  17279 Oleander Ln, Sugarloaf Key, FL 33042
• 

  

  /9

  $199,500

  • 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
• 

  

  /23

  $690,000 Sold Feb 11, 2025

  17295 Keystone Rd, Sugarloaf Shores, FL 33042

  • Land

  Last Sold Summary

  • 7% Below List Price
  • 8 Days On Market

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

  17295 Keystone Rd, Sugarloaf Shores, FL 33042
• 

  

  /38

  Est $2,274,871 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 1,181 Sq Ft

  2035 Long Beach Dr, Big Pine Key, FL 33043

  2035 Long Beach Dr, Big Pine Key, FL 33043
• 

  

  /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
• 

  

  /40

  $1,115,000 Sold Sep 10, 2025

  28552 Maracaibo Rd, Little Torch Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 988 Sq Ft
  • Built 1989

  Last Sold Summary

  • 3% Below List Price
  • $1,129/SF
  • 8 Days On Market

  Current Estimated Value $1,097,878

  Last Listing Agent Teri Hiller Coldwell Banker Schmitt Real Estate Co.

  28552 Maracaibo Rd, Little Torch Key, FL 33042
• 

  

  /30

  Est $983,071 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 650 Sq Ft

  31625 Warner St, Big Pine Key, FL 33043

  31625 Warner St, Big Pine Key, FL 33043

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