Summerland Key, FL Homes

• 

  

  

  /50

  Est $971,213

  Not Listed For Sale

  17396 Jamaica Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,224 Sq Ft
  • Built 1992

  17396 Jamaica Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Sarah Eckert Coldwell Banker Schmitt Real Estate Co. (KW)
• 

  

  

  /18

  $799,000

  • 3 Beds
  • 1 Bath
  • 1,043 Sq Ft

  550 Pine Ln, Big Pine Key, FL 33043

  This newly remodeled 3-bedroom, 1-bathroom home is perfectly positioned on a spacious lot in the heart of Big Pine Key, offering 10,275 sq ft of land and an incredible 75 feet of waterfrontage, with a concrete seawall. With quick access to the ocean via Spanish Harbor Channel, this is a boater's dream come true. Inside, enjoy peace of mind with impact-rated windows and doors, a sturdy metal roof,

  Justyn Ewald Expert Realty LLC

  550 Pine Ln, Big Pine Key, FL 33043
• 

  

  

  /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 $1,056,360

  Last Listing Agent Alexa Morgan Buy The Keys

  17338 Dolphin St E, Summerland Key, FL 33042
• 

  

  

  /74

  Est $3,246,909

  Not Listed For Sale

  22572 Jolly Roger Dr, Summerland Key, FL 33042

  • 6 Beds
  • 4 Baths
  • 3,225 Sq Ft
  • Built 1963

  22572 Jolly Roger Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 313 Days On Market

  Last Listing Agent Jan Fritz Coldwell Banker Schmitt RE Co.
• 

  

  

  /24

  $1,595,000

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

  182 Venetian Way, Summerland Key, FL 33042

  Experience classic Florida Keys waterfront living in this spacious canal-front retreat on Sugarloaf Key, offering boating access, expansive indoor-outdoor living, and just a short drive to Key West. 3,000 square feet of finished living space including 4 bedrooms and 3 baths. Situated on a wide canal with ample room for a future dock, offering the opportunity to create your own boating paradise.

  James Olive LoKation Real Estate

  182 Venetian Way, Summerland Key, FL 33042
• 

  

  /42

  $920,000

  Sold Jun 18, 2026

  22954 Buccaneer Ln, Cudjoe Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1990

  Last Sold Summary

  • 8% Below List Price
  • $657/SF
  • 30 Days On Market

  Current Estimated Value $923,547

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  22954 Buccaneer Ln, Cudjoe Key, FL 33042
• 

  

  /40

  Est $1,082,077

  Not Listed For Sale

  22983 Anne Bonny Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,320 Sq Ft
  • Built 1986

  22983 Anne Bonny Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 109 Days On Market

  Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.
• 

  

  /60

  $799,000

  $88K PRICE DROP Under Contract

  • 2 Beds
  • 1 Bath
  • 806 Sq Ft

  701 Spanish Main Dr Unit 49, Cudjoe Key, FL 33042

  ********Nightly Licensed Transient Rental!!!********This amazing, two bedroom / one bathroom, open water front views , nightly transient rental is ready for you to enjoy both the beauty of this location and the income off the nightly rental license. The floor plan makes the open water views as its main focus. Cook the catch of the day overlooking the waters that you just caught that

  Bobby Coe RE/MAX Keys Connection (KW)

  701 Spanish Main Dr Unit 49, Cudjoe Key, FL 33042
• 

  

  /37

  $830,000

  Sold Jun 10, 2026

  153 Peg Leg Ln, Cudjoe Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,203 Sq Ft
  • Built 1997

  Last Sold Summary

  • 8% Below List Price
  • $690/SF
  • 91 Days On Market

  Current Estimated Value $849,863

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  153 Peg Leg Ln, Cudjoe Key, FL 33042
• 

  

  /6

  Est $648,659

  Not Listed For Sale

  79 Coral Ave, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,144 Sq Ft
  • Built 2004

  79 Coral Ave, Summerland Key, FL 33042

  Last Sold Summary

  • 32 Days On Market

  Last Listing Agent Melva Wagner Sunshine State Realty Services
• 

  

  /40

  $689,000

  • 1 Bed
  • 1 Bath
  • 820 Sq Ft

  2231 Middle Torch Rd, Summerland Key, FL 33042

  Imagine having the freedom to create your own secluded retreat in the heart of the Lower Florida Keys. This remarkable offering includes two adjacent 2.5-acre parcels, combining for approximately 5 acres--an exceptionally rare amount of land in the Florida Keys. Existing improvements include two separate residences, each offering one bedroom and one bathroom. One parcel is improved with a

  Justyn Ewald Expert Realty LLC

  2231 Middle Torch Rd, Summerland Key, FL 33042
• 

  

  /34

  $762,000

  Sold Jan 22, 2026

  726 Jamaica Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,568 Sq Ft
  • Built 1986

  Last Sold Summary

  • 15% Below List Price
  • $486/SF
  • 325 Days On Market

  Current Estimated Value $787,992

  Last Listing Agent Natallie Liz Expert Realty LLC (HQ)

  726 Jamaica Ln, Summerland Key, FL 33042
• 

  

  /40

  Est $765,653

  Not Listed For Sale

  27337 Tobago Ln, Summerland Key, FL 33042

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

  27337 Tobago Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co
• 

  

  /22

  $5,200,000

  • 8 Beds
  • 6 Baths
  • 3,029 Sq Ft

  1557 Long Beach Dr, Big Pine Key, FL 33043

  Coastal living awaits at this spacious property in Long Beach Estates on Big Pine Key! Offering exceptional privacy and direct access to island life, this lot features ample space for your island sanctuary. Located just minutes from pristine beaches, local dining, open water boating, and the Bahia Honda State Park. Perfectly situated in the heart of the Lower Keys, offering quiet, relaxed island

  Greisy Montes De Oca The Brokerage A Real Estate Company

  1557 Long Beach Dr, Big Pine Key, FL 33043
• 

  

  /47

  $1,375,000

  Sold May 20, 2026

  16823 E Point Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2.5 Baths
  • 1,740 Sq Ft
  • Built 1987

  Last Sold Summary

  • 5% Below List Price
  • $790/SF
  • 46 Days On Market

  Current Estimated Value $1,388,000

  Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.

  16823 E Point Dr, Summerland Key, FL 33042
• 

  /2

  Est $2,504,530

  Not Listed For Sale

  20820 7th Ave W, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 2,000 Sq Ft
  • Built 1972

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

  

  /41

  $949,000

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

  342 Spanish Main Dr, Summerland Key, FL 33042

  Welcome to 342 Spanish Main Drive, a beautiful canal-front home in the heart of Cudjoe Key, offering the perfect combination of waterfront living, modern comfort, and laid-back Florida Keys charm. This two-story residence features 3 bedrooms and 2 full bathrooms, thoughtfully designed for both everyday living and relaxing island escapes. The bright, open interior is move-in ready and includes a

  Monika Rydzak eXp Realty LLC KW Branch

  342 Spanish Main Dr, Summerland Key, FL 33042
• 

  

  /40

  $1,115,000

  Sold Sep 10, 2025

  28552 Maracaibo Rd, Summerland 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 $1,110,734

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

  28552 Maracaibo Rd, Summerland Key, FL 33042
• 

  

  /48

  Est $984,461

  Not Listed For Sale

  27342 Anguila Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,320 Sq Ft
  • Built 1976

  27342 Anguila Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 36 Days On Market

  Last Listing Agent Coby Taylor Expert Realty LLC (HQ)
• 

  

  /31

  $982,600

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  701 Spanish Main Dr Unit 198, Cudjoe Key, FL 33042

  Welcome to Oceanview Serenity, an exceptional, open-water retreat located in the gated community of Venture Out at Cudjoe Key (Mile Marker 23). This completely renovated 2-bedroom, 2-bathroom mid-rise offers rare, unobstructed turquoise ocean views as if you are floating on the water. A true boater's paradise, the property boasts a massive concrete seawall with effortless deep-water access.

  Jonathan Minerick Homecoin.com

  701 Spanish Main Dr Unit 198, Cudjoe Key, FL 33042
• 

  

  /49

  $950,000

  Sold Apr 27, 2026

  29559 Ranger Ave, Big Pine Key, FL 33043

  • 2 Beds
  • 2.5 Baths
  • 1,200 Sq Ft
  • Built 1984

  Last Sold Summary

  • 25% Below List Price
  • $792/SF
  • 499 Days On Market

  Current Estimated Value $959,037

  Last Listing Agent Donna Halstead Coldwell Banker Schmitt RE Co.

  29559 Ranger Ave, Big Pine Key, FL 33043
• 

  

  /68

  Est $2,649,539

  Not Listed For Sale

  531 Seminole Dr, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,604 Sq Ft
  • Built 1985

  531 Seminole Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 57 Days On Market

  Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.
• 

  

  /36

  $1,169,000

  $81K PRICE DROP Under Contract

  • 2 Beds
  • 2 Baths
  • 1,024 Sq Ft

  29662 Independence Ave, Big Pine Key, FL 33043

  DOUBLE LOT waterfront opportunity in Big Pine Key! This charming 2 bedroom, 2 bathroom home is ideally situated on a fenced double lot along a canal with excellent boating access and a prime Lower Keys location. Boaters will appreciate the quick and convenient access to both the Atlantic Ocean and the Gulf , making this property an ideal home base for fishing, diving, and exploring the

  Halley Haack Coldwell Banker Schmitt RE Co.

  29662 Independence Ave, Big Pine Key, FL 33043
• 

  

  /36

  $755,000

  Sold Sep 22, 2025

  1590 Gardenia Ln, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1977

  Last Sold Summary

  • 6% Below List Price
  • $629/SF
  • 104 Days On Market

  Current Estimated Value $778,201

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  1590 Gardenia Ln, Big Pine Key, FL 33043
• 

  

  /30

  Est $2,394,316

  Not Listed For Sale

  17082 Starfish Ln W, Summerland Key, FL 33042

  • 6 Beds
  • 3 Baths
  • 3,000 Sq Ft
  • Built 1988

  17082 Starfish Ln W, Summerland Key, FL 33042

  Last Sold Summary

  • 38 Days On Market

  Last Listing Agent Andrea Goodwin KeyIsle Realty - Florida Keys
• 

  

  /61

  $639,000

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  701 Spanish Main Dr Unit 495, Cudjoe Key, FL 33042

  Spectacular peekaboo open water views abound with this updated 2 bed/2 bath canal front home with 35 foot seawall. Located in a gated community with tons of amenities. New kitchen w/Caesar quartz countertops, full backsplash, new stainless steel appliances, Koehler sink, modern, white cabinets with an abundance of storage, including a large center Island. Open concept floor plan with open water

  Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 495, Cudjoe Key, FL 33042
• 

  

  /42

  $775,000

  Sold Oct 01, 2025

  22988 Port Royal Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,122 Sq Ft
  • Built 1998

  Last Sold Summary

  • 6% Below List Price
  • $691/SF
  • 68 Days On Market

  Current Estimated Value $795,576

  Last Listing Agent Walter Ceballos, P.A. Berkshire Hathaway HomeServices Keys Real Estate

  22988 Port Royal Ln, Summerland Key, FL 33042
• 

  /2

  Est $987,814

  Not Listed For Sale

  17174 Kingfish Ln W, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,218 Sq Ft
  • Built 1975

  17174 Kingfish Ln W, Summerland Key, FL 33042
• 

  

  /43

  $735,000

  $45K PRICE DROP

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

  27024 Shannahan Rd, Summerland Key, FL 33042

  Well-maintained elevated home offering the perfect combination of comfort, functionality, and peace of mind. Built above flood elevation, this move-in-ready property features an open-concept floor plan with spacious living and dining areas, durable flooring throughout, and a bright kitchen with abundant cabinetry, stainless steel appliances, and generous counter space.The covered and

  Jenna Stauffer Ocean Sotheby's International Realty

  27024 Shannahan Rd, Summerland Key, FL 33042
• 

  

  /6

  $1,400,000

  Sold May 28, 2026

  17195 Hibiscus Ln W, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft
  • Built 1987

  Last Sold Summary

  • $1,080/SF
  • 0 Days On Market

  Current Estimated Value $1,381,298

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  17195 Hibiscus Ln W, Summerland Key, FL 33042
• 

  

  /50

  Est $1,753,686

  Not Listed For Sale

  21025 Hamilton Ave, Summerland Key, FL 33042

  • 6 Beds
  • 3.5 Baths
  • 4,060 Sq Ft
  • Built 1983

  21025 Hamilton Ave, Summerland Key, FL 33042

  Last Sold Summary

  • 47 Days On Market

  Last Listing Agent Mike Kane Internet Realty of the Florida Keys
• 

  

  /65

  $1,595,000

  Pending

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

  887 Bay Dr, Summerland Key, FL 33042

  Priced at Current appraised value, this 3-bedroom, 3-bath concrete fortress on 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

  Amy Hanson Realty Executives Florida Keys Summerland Branch

  887 Bay Dr, Summerland Key, FL 33042
• 

  

  /94

  $3,150,000

  Sold Jul 21, 2026

  17249 Bonefish Ln E, Sugarloaf Key, FL 33042

  • 5 Beds
  • 4 Baths
  • 3,060 Sq Ft
  • Built 1970

  Last Sold Summary

  • 10% Below List Price
  • $1,029/SF
  • 130 Days On Market

  Current Estimated Value $3,123,049

  Last Listing Agent Daniel Urban Expert Realty LLC (HQ)

  17249 Bonefish Ln E, Sugarloaf Key, FL 33042
• 

  

  /31

  Est $656,105

  Not Listed For Sale

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

  • 2 Beds
  • Built 1991

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

  Last Sold Summary

  • 15 Days On Market

  Last Listing Agent Kim Babenzien Expert Realty LLC (HQ)
• 

  

  /34

  $899,000

  • 1 Bed
  • 1 Bath
  • 552 Sq Ft

  31342 Avenue I, Big Pine Key, FL 33043

  This recently built canal front home is situated in a highly desirable area of Big Pine just minutes to the open water. The home has a bright open kitchen with plenty of cabinets, stainless appliances, attractive tile backsplash and built in table with seating overlooking the living area.......From the bedroom with adjoined bathroom there are partial ocean views. There is also a utility room with

  Rob Severin Rob Severin Real Estate Co

  31342 Avenue I, Big Pine Key, FL 33043
• 

  

  /32

  $895,000

  Sold Jun 23, 2026

  30451 Hibiscus Ln, Big Pine Key, FL 33043

  • 4 Beds
  • 3 Baths
  • 2,503 Sq Ft
  • Built 2010

  Last Sold Summary

  • 8% Below List Price
  • $358/SF
  • 117 Days On Market

  Current Estimated Value $920,207

  Last Listing Agent Rose Dell Keller Williams Key West Compass Realty

  30451 Hibiscus Ln, Big Pine Key, FL 33043
• 

  

  /15

  Est $720,110

  Not Listed For Sale

  16991 Shore Dr, Summerland Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 1,134 Sq Ft
  • Built 1958

  16991 Shore Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 17 Days On Market

  Last Listing Agent Daniel Urban Expert Realty LLC (HQ)
• 

  

  /42

  $829,000

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 984 Sq Ft

  937 Loggerhead Ln, Summerland Key, FL 33042

  Opportunities like this are hard to find in the Lower Keys--this fully renovated 3-bedroom, 2-bath home sits on a generous half-acre lot in the highly desirable Sugarloaf Key area, offering space, privacy, and modern upgrades throughout. Designed for easy coastal living, the home features durable Hardie board siding, a long-lasting metal roof, tile flooring throughout, and an energy-efficient

  Richard Haskins Buy The Keys

  937 Loggerhead Ln, Summerland Key, FL 33042
• 

  

  /53

  $615,000

  Sold Mar 31, 2026

  29073 Iris Dr, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,336 Sq Ft
  • Built 1974

  Last Sold Summary

  • 2% Below List Price
  • $460/SF
  • 4 Days On Market

  Current Estimated Value $629,198

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

  29073 Iris Dr, Big Pine Key, FL 33043
• 

  

  /56

  Est $1,774,014

  Not Listed For Sale

  20966 8th Ave W, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 2,166 Sq Ft
  • Built 1982

  20966 8th Ave W, Summerland Key, FL 33042

  Last Sold Summary

  • 31 Days On Market

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

Showing Results 481 - 520, Page 13 of 18