Summerland Key, FL Homes

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  /6

  Not Listed For Sale

  Lot 27 Angelfish Rd, Ramrod Key, FL 33042

  Lot 27 Angelfish Rd, Ramrod Key, FL 33042
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  /28

  $838,000

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  3856 Donna Rd, Big Pine Key, FL 33043

  Sportsman Paradise. 2 Bedroom home with Permitted Concrete BOAT RAMP, concrete sea wall, concrete fish cleaning table with Permitted downstairs bathroom. Real short idle to open water. Back country fishing, lobster diving/snorkel and stone crabs right in your back yard. Easy access to to Atlantic. Lots of storage downstairs with workroom/laundry room, Very large downstairs Bathroom, Large storage

  Alan Ballas Alan Ballas Realty

  3856 Donna Rd, Big Pine Key, FL 33043
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  /46

  $1,750,000 Sold Feb 13, 2025

  17194 Kingfish Ln W, Summerland Key, FL 33042

  • 4 Beds
  • 2 Baths
  • 2,073 Sq Ft
  • Built 2011

  Last Sold Summary

  • 17% Below List Price
  • $844/SF
  • 150 Days On Market

  Current Estimated Value $1,731,682

  Last Listing Agent Samantha Barrabeitg Taylor & Assoc. RE, Inc.

  17194 Kingfish Ln W, Summerland Key, FL 33042
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  /30

  Est $738,861 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,064 Sq Ft

  124 Yardarm Rd, Cudjoe Key, FL 33042

  124 Yardarm Rd, Cudjoe Key, FL 33042
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  /25

  $623,999

  • 3 Beds
  • 2 Baths
  • 1,204 Sq Ft

  31243 E Ave E, Big Pine Key, FL 33043

  **Price Improvementt** OPEN HOUSE SAT FEB 7TH NOON-2PM SELLER SAYS BRING ALL OFFERS!!! Welcome to your slice of paradise in Big Pine Key! This charming 3-bedroom, 2-bath home is an ideal opportunity for families or first-time homebuyers seeking the quintessential Florida Keys lifestyle. Step inside to discover a comfortable and inviting living space, perfect for creating lasting memories.Outside,

  Sabre Mendoza Coldwell Banker Schmitt RE Co.

  31243 E Ave E, Big Pine Key, FL 33043
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  /22

  $750,000 Sold Apr 10, 2025

  29548 Enterprise Ave, Big Pine Key, FL 33043

  • 4 Beds
  • 4 Baths
  • 2,232 Sq Ft
  • Built 1974

  Last Sold Summary

  • 38% Below List Price
  • $336/SF
  • 523 Days On Market

  Current Estimated Value $766,164

  Last Listing Agent Jennifer Weeks Select Properties of NWFL

  29548 Enterprise Ave, Big Pine Key, FL 33043
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  /17

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 770 Sq Ft

  701 Spanish Main Dr Unit 83, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 83, Cudjoe Key, FL 33042
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  /2

  $60,232

  • Land

  0 Bk 4 Lt 9 Pine Crest Rd Unit 618082, Big Pine Key, FL 33043

  ROGO lot worth 2 points for DEDICATION purposes. Seller has county ROGO Letter of Land Dedication verifying lot is eligible for land dedication/2 points. Want to build quicker? This is a path. Buyer to verify points and process with Monroe County. See Documents tab for letter.

  Donna Pezzi Keller Williams Key West Compass Realty

  0 Bk 4 Lt 9 Pine Crest Rd Unit 618082, Big Pine Key, FL 33043
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  /40

  $1,050,000 Sold Jan 12, 2026

  32734 Bimini Ln, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,654 Sq Ft
  • Built 1995

  Last Sold Summary

  • 14% Below List Price
  • $635/SF
  • 235 Days On Market

  Last Listing Agent Ally Kelley Ocean Sotheby's International

  32734 Bimini Ln, Big Pine Key, FL 33043
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  /41

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 860 Sq Ft

  701 Spanish Main Dr Unit 94, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 94, Cudjoe Key, FL 33042
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  /37

  $275,000

  • Land

  701 Spanish Main Dr Unit 146, Cudjoe Key, FL 33042

  Buildable RV Lot. Transient (1 Day Rental) Rentals Opportunity in the Lower Keys! Located in a serene, well-maintained gated community at Mile Marker 23. This RV/Buildable lot offers the ideal spot for your home on wheels, or the opportunity to build your dream home. Boasting a private lot with landscaping, pea rock, storage box and concrete parking pad. Lot is equipped with full hookups

  Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 146, Cudjoe Key, FL 33042
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  /38

  $935,000 Sold Jun 30, 2025

  29374 Saratoga Ave, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 1986

  Last Sold Summary

  • 18% Below List Price
  • $835/SF
  • 150 Days On Market

  Current Estimated Value $942,848

  Last Listing Agent Dawn McComish Lokation Real Estate

  29374 Saratoga Ave, Big Pine Key, FL 33043
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  /65

  Est $259,975 Not Listed For Sale

  • 1 Bed

  701 Spanish Main Dr Unit 620, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 620, Cudjoe Key, FL 33042
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  /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
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  /44

  $650,000 Sold Jun 30, 2025

  701 Spanish Main Dr Unit 390, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 828 Sq Ft
  • Built 2002

  Last Sold Summary

  • 4% Below List Price
  • $785/SF
  • 8 Days On Market

  Last Listing Agent Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 390, Cudjoe Key, FL 33042
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  /12

  Est $565,961 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 880 Sq Ft

  31352 Avenue E, Big Pine Key, FL 33043

  31352 Avenue E, Big Pine Key, FL 33043
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  /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
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  /51

  $1,100,000 Sold May 02, 2025

  27984 Barton Ave, Little Torch Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,225 Sq Ft
  • Built 1993

  Last Sold Summary

  • 8% Below List Price
  • $898/SF
  • 126 Days On Market

  Current Estimated Value $1,090,460

  Last Listing Agent Steven Koleno Beycome of Florida, LLC

  27984 Barton Ave, Little Torch Key, FL 33042
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  /2

  Est $796,234 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,575 Sq Ft

  1547 Narcissus Ave, Big Pine Key, FL 33043

  1547 Narcissus Ave, Big Pine Key, FL 33043
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  /17

  $265,000

  • 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

  Jenifer Hirsch Bluescape Real Estate

  701 Spanish Main Dr Unit 643, Cudjoe Key, FL 33042
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  /2

  $1,400,000 Sold Sep 17, 2025

  491 W Indies Dr, Ramrod Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,204 Sq Ft
  • Built 2020

  Last Sold Summary

  • $1,163/SF
  • 0 Days On Market

  Current Estimated Value $1,410,325

  Last Listing Agent Mark Gable Engel & Volkers Marathon

  491 W Indies Dr, Ramrod Key, FL 33042
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  /2

  Est $743,789 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,575 Sq Ft

  1791 Narcissus Ave, Big Pine Key, FL 33043

  1791 Narcissus Ave, Big Pine Key, FL 33043
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  /58

  $599,000

  • 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
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  /40

  $1,350,000 Sold May 15, 2025

  31254 Hollerich Dr, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,315 Sq Ft
  • Built 2025

  Last Sold Summary

  • 8% Below List Price
  • $1,027/SF
  • 6 Days On Market

  Current Estimated Value $1,199,519

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

  31254 Hollerich Dr, Big Pine Key, FL 33043
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  /2

  Est $814,318 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,100 Sq Ft

  29530 Enterprise Ave, Big Pine Key, FL 33043

  29530 Enterprise Ave, Big Pine Key, FL 33043
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  /16

  $1,450,000 Under Contract

  • 3 Beds
  • 3 Baths
  • 1,500 Sq Ft

  570 Blackbeard Rd, Summerland Key, FL 33042

  Coming Summer/Fall 2026. Step into the laid-back charm of the Florida Keys with this spacious 1,500 sqft home, perfectly situated along a peaceful deep boating canal in the Lower Keys. Located in a tranquil, low-traffic neighborhood, this property offers a serene escape with plenty of room to enjoy life at your own pace. Inside the home: An open, airy floor plan that allows you to spread out and

  Nick Boumerhi Meyer and Boumerhi Realty LLC

  570 Blackbeard Rd, Summerland Key, FL 33042
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  /23

  $710,000 Sold Aug 20, 2025

  19603 Seminole St, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft
  • Built 2014

  Last Sold Summary

  • 3% Below List Price
  • $598/SF
  • 5 Days On Market

  Current Estimated Value $719,094

  Last Listing Agent Steven Koleno Beycome of Florida, LLC

  19603 Seminole St, Summerland Key, FL 33042
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  /2

  Est $1,009,161 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 1,568 Sq Ft

  29528 Constitution Ave, Big Pine Key, FL 33043

  29528 Constitution Ave, Big Pine Key, FL 33043
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  /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
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  /30

  $628,000 Sold Sep 05, 2025

  31256 Avenue H, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,144 Sq Ft
  • Built 2005

  Last Sold Summary

  • 4% Below List Price
  • $549/SF
  • 106 Days On Market

  Current Estimated Value $626,863

  Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

  31256 Avenue H, Big Pine Key, FL 33043
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  /2

  Est $791,300 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 875 Sq Ft

  677 Heck Ave, Summerland Key, FL 33042

  677 Heck Ave, Summerland Key, FL 33042
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  /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
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  /20

  $260,000 Sold Mar 21, 2025

  31048 Avenue J, Big Pine Key, FL 33043

  • 2 Beds
  • 1 Bath
  • 588 Sq Ft
  • Built 1967

  Last Sold Summary

  • 12% Below List Price
  • $442/SF
  • 151 Days On Market

  Last Listing Agent Rose Dell Keller Williams Key West Compass Realty

  31048 Avenue J, Big Pine Key, FL 33043
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  /19

  Est $1,043,928 Not Listed For Sale

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

  825 Pirates Rd, Summerland Key, FL 33042

  825 Pirates Rd, Summerland Key, FL 33042
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  /46

  $735,000

  • 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
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  /34

  $695,000 Sold Aug 05, 2025

  1555 Watson Blvd, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,233 Sq Ft
  • Built 1959

  Last Sold Summary

  • 1% Below List Price
  • $564/SF
  • 5 Days On Market

  Current Estimated Value $705,392

  Last Listing Agent Terrance Sullivan Ocean Sotheby's International Realty

  1555 Watson Blvd, Big Pine Key, FL 33043
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  /2

  Est $931,978 Not Listed For Sale

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

  337 46th St, Summerland Key, FL 33042

  337 46th St, Summerland Key, FL 33042
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  /49

  $280,000

  • 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
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  /41

  $1,350,000 Sold Aug 18, 2025

  20735 5th Ave W, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,582 Sq Ft
  • Built 1985

  Last Sold Summary

  • 7% Below List Price
  • $853/SF
  • 16 Days On Market

  Current Estimated Value $1,356,755

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

  20735 5th Ave W, Summerland Key, FL 33042
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  /2

  Est $1,696,283 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,942 Sq Ft

  25326 3rd St, Summerland Key, FL 33042

  25326 3rd St, Summerland Key, FL 33042

Showing Results 401 - 440, Page 11 of 18