Summerland Key, FL Homes

• 

  

  

  /39

  $698,000

  • 2 Beds
  • 1 Bath
  • 672 Sq Ft

  30881 Witters Ln, Big Pine Key, FL 33043

  Updated cottage with all the necessities you need with minimal maintenance. This CBS home has a newer metal roof, mini split A/c, updated kitchen on 3 lots only a very short ride to Boggie Channel, the only market channel to the Atlantic and Gulf in the Lower Keys. This is a great opportunity for boaters and naturalist as this is only a short walk or kayak to No Name Key and surrounding waters

  John Nazzaro Keller Williams Realty Premier Properties - Kendall

  30881 Witters Ln, Big Pine Key, FL 33043
• 

  

  

  /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

  Current Estimated Value $3,544,961

  Last Listing Agent Karen Williams-deCastro LPT Realty, LLC

  815 E Shore Dr, Summerland Key, FL 33042
• 

  

  

  /19

  Est $1,015,390 Not Listed For Sale

  825 Pirates Rd, Summerland Key, FL 33042

  • 4 Beds
  • 4 Baths
  • 1,920 Sq Ft
  • Built 1982

  825 Pirates Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 6% Above List Price
  • $560/SF
  • 32 Days On Market

  Last Sold Price $1,075,000

  Last Listing Agent Christina Davis Coldwell Banker Schmitt RE Co.
• 

  

  

  /4

  $400,000

  • Land
  • 1,400 Acres
  • $286 per Acre

  27378 Jamaica Ln, Summerland Key, FL 33042

  ROGO and Building permit in hand! allows for immediate construction 6,000sq.ft lot on Ramrod Key, 60 feet of waterfront canal with quick access to ocean. Permit approved al Monroe County for a 1,400 sq.ft CBS 3 bedroom, 2.5 bath residence. Connected to water and sewer on site. ACOE and DEP mitigation paid. Permit for dock and lift submitted.Correct address: 27378 JAMAICA LN RAMROD KEY, FL

  Patricia Borges Borges Realty Group LLC

  27378 Jamaica Ln, Summerland Key, FL 33042
• 

  

  

  /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
• 

  /2

  Est $871,381 Not Listed For Sale

  337 46th St, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 1,600 Sq Ft
  • Built 1958

  337 46th St, Summerland Key, FL 33042

  Last Sold Summary

  • 16% Below List Price
  • $469/SF

  Last Sold Price $750,000

  Last Listing Agent Greg MacLaren Internet Realty of the Florida Keys
• 

  

  /17

  $255,000

  • Land

  701 Spanish Main Dr Unit 643, Cudjoe Key, FL 33042

  Welcome to island living at its best! This 35'x 69' RV lot is ready for your rig with full hookups and all the perks of Venture Out--golf cart streets, 24-hour security, pool, tennis, pickleball, and a marina. Located minutes from local favorites Morning Joint, Square Grouper, and 420 Lounge, plus only 19 miles to Key West. Whether you're here for fishing, boating, or simply soaking in the Keys

  Bea Evelyn Citron Compass Florida, LLC

  701 Spanish Main Dr Unit 643, Cudjoe Key, FL 33042
• 

  

  /14

  $225,000 Sold Apr 01, 2026

  27398 Jamaica Ln, Ramrod Key, FL 33042

  • Land

  Last Sold Summary

  • 25% Below List Price
  • 173 Days On Market

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

  27398 Jamaica Ln, Ramrod Key, FL 33042
• 

  

  /15

  Est $213,956 Not Listed For Sale

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

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

  Last Sold Summary

  • 7% Above List Price
  • 13 Days On Market

  Last Sold Price $200,000

  Last Listing Agent Cheryl Billings Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys
• 

  

  /58

  $594,000 Under Contract

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

  175 E Cahill Ct, Big Pine Key, FL 33043

  Discover relaxed Keys living in this elevated 2 bedroom, 2 bath stilted home tucked away on a plugged swimming canal in Big Pine Key. Surrounded by two wooded vacant lots, this property offers exceptional privacy and a peaceful setting.The calm, non boating canal is perfect for swimming, kayaking, and paddleboarding, creating a true backyard oasis. An additional spiral staircase off the open

  Darlene Alferes Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

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

  

  /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

  Current Estimated Value $1,157,642

  Last Listing Agent Jenny Perry Preferred Properties (KW)

  478 Blackbeard Rd, Summerland Key, FL 33042
• 

  /2

  Est $734,308 Not Listed For Sale

  30827 Baileys Ln, Big Pine Key, FL 33043

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

  30827 Baileys Ln, Big Pine Key, FL 33043

  Last Sold Summary

  • 3% Below List Price
  • $762/SF

  Last Sold Price $760,000

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

  

  /58

  $295,000

  • 1 Bed
  • 1 Bath
  • 316 Sq Ft

  701 Spanish Main Dr Unit LOT 423, Cudjoe Key, FL 33042

  INCOME PRODUCING POWERHOUSE! Welcome to 'Conch Hideaway' #423, a proven tropical retreat and turnkey business in the premier Venture Out community. This charming 1BD/1BA home is a high-performing vacation rental that grossed $30,705 in 2025! INVESTMENT HIGHLIGHTS: Already live with rentals for 2026, this property has 27 days currently booked with $2,085.05 in gross revenue transferring to the

  Kate Baldwin Bluescape Real Estate

  701 Spanish Main Dr Unit LOT 423, Cudjoe Key, FL 33042
• 

  

  /29

  $825,000 Sold Feb 27, 2026

  17245 Jamaica Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 2000

  Last Sold Summary

  • 11% Below List Price
  • $661/SF
  • 104 Days On Market

  Current Estimated Value $846,853

  Last Listing Agent Team Kaufelt Truman & Co. (KW)

  17245 Jamaica Ln, Summerland Key, FL 33042
• 

  

  /16

  Est $572,576 Not Listed For Sale

  30323 Poinciana Rd, Big Pine Key, FL 33043

  • 5 Beds
  • 2 Baths
  • 1,562 Sq Ft
  • Built 1971

  30323 Poinciana Rd, Big Pine Key, FL 33043

  Last Sold Summary

  • $365/SF
  • 59 Days On Market

  Last Sold Price $570,000

  Last Listing Agent Greg MacLaren Internet Realty of the Florida Keys
• 

  

  /129

  $6,200,000

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

  24200 Overseas Hwy, Summerland Key, FL 33042

  Welcome to an unparalleled coastal lifestyle, where modern luxury meets the ultimate boater's paradise. This extraordinary compound, nestled along a prime stretch of the Florida Keys waterfront, has been completely reimagined for the discerning owner who demands both sophisticated living spaces and robust functionality. This pristine oceanfront estate is situated on a manicured one-acre gated

  Sylvia Werling Keller Williams Key West Compass Realty

  24200 Overseas Hwy, Summerland Key, FL 33042
• 

  

  /40

  $1,300,000 Sold Feb 26, 2026

  537 Heck Ave, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,422 Sq Ft
  • Built 1997

  Last Sold Summary

  • $914/SF
  • 29 Days On Market

  Current Estimated Value $1,269,102

  Last Listing Agent Michelle Howerton Brenda Donnelly Real Estate LLC

  537 Heck Ave, Summerland Key, FL 33042
• 

  /2

  Est $3,970,138 Not Listed For Sale

  1152 W Shore Dr, Big Pine Key, FL 33043

  • 3 Beds
  • 3 Baths
  • 4,030 Sq Ft
  • Built 2008

  1152 W Shore Dr, Big Pine Key, FL 33043

  Last Sold Summary

  • 3% Below List Price
  • $1,017/SF

  Last Sold Price $4,100,000

  Last Listing Agent Anneliese Dietrick Coldwell Banker Schmitt Lower Keys (KW)
• 

  

  /45

  $7,000,000

  • 3 Beds
  • 4 Baths
  • 2,851 Sq Ft

  0 Melody Key Unit 616249, Summerland Key, FL 33042

  An unparalleled opportunity to own your own private island in the Florida Keys. Melody Key is a true rarity--an off-grid sanctuary offering complete privacy, turquoise waters in every direction, and now a brand-new boat dock and observation deck that set the stage for its next chapter.The property is currently undergoing a full renovation with permits and detailed architectural drawings already

  Scott Forman Royal Palms Realty (KW)

  0 Melody Key Unit 616249, 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 $900,456

  Last Listing Agent Alexa Morgan Buy The Keys

  17338 Dolphin St E, Summerland Key, FL 33042
• 

  

  /3

  Est $1,091,000 Not Listed For Sale

  Unlisted Address

  • 5 Beds
  • 4 Baths
  • 1,702 Sq Ft
  • Built 1967

  Unlisted Address

  Last Sold Summary

  • 9% Above List Price
  • $588/SF
  • 1 Day On Market

  Last Sold Price $1,000,000

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

  

  /46

  $699,000

  • 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
• 

  

  /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 $359,425

  Last Listing Agent Kirksten Irick Preferred Properties (KW)

  31456 Ave F, Big Pine Key, FL 33043
• 

  

  /63

  Est $897,606 Not Listed For Sale

  27322 Saint Martin Ln, Summerland Key, FL 33042

  • 3 Beds
  • 1 Bath
  • 1,196 Sq Ft
  • Built 1974

  27322 Saint Martin Ln, Summerland Key, FL 33042

  Last Sold Summary

  • $753/SF
  • 79 Days On Market

  Last Sold Price $900,000

  Last Listing Agent Dina Schoneck Berkshire Hathaway HomeServices Knight & Gardner Realty
• 

  

  /49

  $275,000

  • 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
• 

  

  /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 $1,093,305

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

  128 Le Grand Ln, Summerland Key, FL 33042
• 

  

  /55

  Est $1,410,051 Not Listed For Sale

  266 Colson Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,943 Sq Ft
  • Built 1975

  266 Colson Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 3% Above List Price
  • $706/SF
  • 1 Day On Market

  Last Sold Price $1,371,000

  Last Listing Agent Coby Taylor Taylor & Assoc. RE, Inc.
• 

  

  /43

  $1,050,000

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

  22837 Calico Jack Cir, Summerland Key, FL 33042

  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 too. Quick commute to Key West,

  Beata Sharpe Coldwell Banker Vanguard Realty

  22837 Calico Jack Cir, Summerland Key, 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 $527,018

  Last Listing Agent Rose Dell Keller Williams Key West Compass Realty

  31232 Ave d, Big Pine Key, FL 33043
• 

  

  /37

  Est $1,681,952 Not Listed For Sale

  1008 Buttonwood Dr E, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,920 Sq Ft
  • Built 2008

  1008 Buttonwood Dr E, Summerland Key, FL 33042

  Last Sold Summary

  • 5% Above List Price
  • $833/SF
  • 42 Days On Market

  Last Sold Price $1,600,000

  Last Listing Agent Jenny Perry Preferred Properties (KW)
• 

  

  /9

  $475,000

  • Land

  27460 W Indies Dr, Ramrod Key, FL 33042

  Anay Ramos Miami New Realty

  27460 W Indies Dr, Ramrod 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 $787,036

  Last Listing Agent Natallie Liz Expert Realty LLC (HQ)

  726 Jamaica Ln, Summerland Key, FL 33042
• 

  

  /43

  Est $2,822,598 Not Listed For Sale

  1619 Long Beach Dr, Big Pine Key, FL 33043

  • 5 Beds
  • 5.5 Baths
  • 3,160 Sq Ft
  • Built 1977

  1619 Long Beach Dr, Big Pine Key, FL 33043

  Last Sold Summary

  • 3% Above List Price
  • $918/SF
  • 2 Days On Market

  Last Sold Price $2,900,000

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

  

  /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
• 

  

  /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 $1,105,464

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

  28552 Maracaibo Rd, Little Torch Key, FL 33042
• 

  /2

  Est $1,008,750 Not Listed For Sale

  29552 Independence Ave, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,280 Sq Ft
  • Built 1976

  29552 Independence Ave, Big Pine Key, FL 33043

  Last Sold Summary

  • 6% Below List Price
  • $742/SF

  Last Sold Price $950,000

  Last Listing Agent Donna Halstead Coldwell Banker Schmitt RE Co.
• 

  

  /15

  $1,395,000

  • Land
  • 2.29 Acres
  • $609,173 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 Realty

  1261 Avenue A, Big Pine Key, FL 33043
• 

  

  /8

  $553,000 Sold Mar 06, 2026

  3 W Cook, Cook Island Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 704 Sq Ft
  • Built 1985

  Last Sold Summary

  • 8% Below List Price
  • $786/SF
  • 267 Days On Market

  Last Listing Agent Stephen Hachey

  3 W Cook, Cook Island Key, FL 33043
• 

  

  /42

  Est $1,216,744 Not Listed For Sale

  31040 Atlantis Dr, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft
  • Built 1986

  31040 Atlantis Dr, Big Pine Key, FL 33043

  Last Sold Summary

  • 3% Below List Price
  • $827/SF
  • 128 Days On Market

  Last Sold Price $1,250,000

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate
• 

  

  /24

  $259,000

  • 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

  Ian Calderwood Bluescape Real Estate

  701 Spanish Main Dr Unit 69, Cudjoe Key, FL 33042

Showing Results 401 - 440, Page 11 of 18