Summerland Key, FL Homes

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  /3

  $799,000

  $50K PRICE DROP Pending

  • Land
  • 10 Acres
  • $79,900 per Acre

  LOT 57 Rocky Rd, Sugarloaf Key, FL 33042

  Rare opportunity to acquire approximately 10 acres of vacant residential land in Sugarloaf Key, an area known for its low-density character, natural surroundings, and limited land availability. Large parcels of this size are increasingly scarce in the Lower Florida Keys, positioning this property as a strategic long-term holding or future planning opportunity. On Monroe county records, the

  Eugenia Hernandez PREMIUM PROPERTIES R.E SERVICE

  LOT 57 Rocky Rd, Sugarloaf Key, FL 33042
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  /55

  $1,800,000

  Sold Jul 18, 2025

  22925 John Avery Ln, Summerland Key, FL 33042

  • 4 Beds
  • 4 Baths
  • 2,638 Sq Ft
  • Built 1993

  Last Sold Summary

  • 21% Below List Price
  • $682/SF
  • 164 Days On Market

  Current Estimated Value $1,764,746

  Last Listing Agent Jonathan Minerick Homecoin.com

  22925 John Avery Ln, Summerland Key, FL 33042
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  /46

  Est $2,796,168

  Not Listed For Sale

  961 W Indies Dr, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,006 Sq Ft
  • Built 1998

  961 W Indies Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 37 Days On Market
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  /12

  $495,000

  • Land
  • 2,078 Sq Ft
  • $10,376,420 per Acre

  701 Spanish Main Dr Unit 84, Cudjoe Key, FL 33042

  Rare opportunity to own a transient (1-day minimum) rental RV lot in the Lower Keys. Located in a quiet, well-kept community, this buildable lot is perfect for your RV or for building a custom Keys getaway HomeThe property includes a 35-foot concrete seawall, dock posts, fishing cleaning station, swim ladder, Brand new concrete slab and full hookups with water, sewer, and 30, 50, and 110-amp

  Anay Ramos Miami New Realty

  701 Spanish Main Dr Unit 84, Cudjoe Key, FL 33042
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  /51

  $1,735,000

  Sold May 12, 2026

  1232 W Shore Dr, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 1983

  Last Sold Summary

  • 9% Below List Price
  • $1,291/SF
  • 12 Days On Market

  Current Estimated Value $1,872,072

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  1232 W Shore Dr, Big Pine Key, FL 33043
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  /28

  Est $837,448

  Not Listed For Sale

  27378 Haiti Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 925 Sq Ft
  • Built 1963

  27378 Haiti Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 34 Days On Market
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  /61

  $845,000

  $70K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,520 Sq Ft

  17326 Jamaica Ln, Summerland Key, FL 33042

  Welcome to your slice of Lower Keys paradise--just 17 miles from Key West yet worlds away from the hustle. This elevated 2-bedroom, 2-bath home sits on a generous lot in a fantastic neighborhood, offering the perfect blend of comfort, style, and island living. Inside, vaulted ceilings and impact windows fill the home with natural light and breezy tropical charm. An elevator makes access

  Stephanie Wise Keller Williams Key West Compass Realty

  17326 Jamaica Ln, Summerland Key, FL 33042
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  /10

  $310,000

  Sold May 11, 2026

  30324 Frigate Ln, Big Pine Key, FL 33043

  • Land
  • 8,712 Sq Ft
  • $1,550,000 per Acre

  Last Sold Summary

  • 31% Below List Price
  • 67 Days On Market

  Current Estimated Value $444,181

  Last Listing Agent Derrick Johnson Coco Plum Real Estate

  30324 Frigate Ln, Big Pine Key, FL 33043
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  /41

  Est $886,723

  Not Listed For Sale

  27468 Haiti Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,380 Sq Ft
  • Built 1979

  27468 Haiti Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 6 Days On Market
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  /10

  $1,450,000

  • Land
  • 6,098 Sq Ft
  • $10,357,143 per Acre

  00000 Lagoon Dr, Summerland Key, FL 33042

  Excellent opportunity to build your dream in paradise. This 6,140 sq foot lot with 70.65 ft. of water frontage has a beautiful open water and ocean view. This is the last lot available in this established subdivision Summerland Cove. Easy access to both the Atlantic Ocean and the Gulf of Mexico.

  Marc Ulanowski Equestrian Sotheby's International Realty

  00000 Lagoon Dr, Summerland Key, FL 33042
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  /30

  $775,000

  Sold Sep 30, 2025

  24827 Park Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,274 Sq Ft
  • Built 2018

  Last Sold Summary

  • 14% Below List Price
  • $608/SF
  • 175 Days On Market

  Current Estimated Value $794,549

  Last Listing Agent Juan Benitez Benitez Keller Williams Key West Compass Realty

  24827 Park Dr, Summerland Key, FL 33042
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  /18

  Est $750,784

  Not Listed For Sale

  27438 Haiti Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft
  • Built 1987

  27438 Haiti Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 146 Days On Market
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  /18

  $699,000

  $150K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 1,924 Sq Ft

  1433 Sunset Rd, Big Pine Key, FL 33043

  699,000 for 2 units. Great price reduction on income producing CBS duplex in Big Pine Key. Good boating with direct access to Bogie Channel. Large lot with full seawall. Interior is cute and tidy and would be easy to rent or live in one side and generate extra income. Fully furnished.

  Cheryl Moses Action Keys Realty of the Lower FL Keys LLC

  1433 Sunset Rd, Big Pine Key, FL 33043
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  /17

  $320,000

  Sold Feb 20, 2026

  27977 Coral Shores Rd, Little Torch Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 684 Sq Ft
  • Built 1980

  Last Sold Summary

  • 20% Below List Price
  • $468/SF
  • 54 Days On Market

  Last Listing Agent Dasha Ray Conch Realty LLC (KW)

  27977 Coral Shores Rd, Little Torch Key, FL 33042
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  /45

  Est $1,202,479

  Not Listed For Sale

  23058 Sailfish Ln, Summerland Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 1,280 Sq Ft
  • Built 1980

  23058 Sailfish Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 145 Days On Market
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  /25

  $730,000

  $65K PRICE DROP Under Contract

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

  180 Sugarloaf Dr, Summerland Key, FL 33042

  **Motivated Sellers, all reasonable offers considered** This charming 3 bedroom 2 bath house in Sugarloaf Shores sits on an oversized 12,000sqft lot. Fenced for privacy with plenty of room for a pool, park your boat or RV. Outside you have a quaint patio, outdoor shower and lush gardens. Step inside to find a warm inviting interior space, remodeled kitchen, bonus screened porch and outdoor

  Jenny Perry Preferred Properties (KW)

  180 Sugarloaf Dr, Summerland Key, FL 33042
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  /61

  $835,000

  Sold May 04, 2026

  27332 St Martin Ln, Ramrod Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,716 Sq Ft
  • Built 1974

  Last Sold Summary

  • 14% Below List Price
  • $487/SF
  • 195 Days On Market

  Current Estimated Value $891,154

  Last Listing Agent Mark Gable Engel & Volkers Marathon

  27332 St Martin Ln, Ramrod Key, FL 33042
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  /16

  Est $1,996,266

  Not Listed For Sale

  23076 Tarpon Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,122 Sq Ft
  • Built 1975

  23076 Tarpon Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 82 Days On Market
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  /36

  $859,000

  $120K PRICE DROP Under Contract

  • 2 Beds
  • 2 Baths
  • 861 Sq Ft

  701 Spanish Main Dr Unit 512, Cudjoe Key, FL 33042

  VACATION RENTAL OPPORTUNITY - OPEN WATER VIEWS + 43' DOCK - 2BR/2BA | 864 SQ. FT. Beautifully maintained 2-bedroom, 2-bath waterfront home offering open water views and excellent rental potential. This 864 sq. ft. property features a 43-foot dock with quick access to world-class boating, fishing, and diving in the Florida Keys. Ideal for investors or owners seeking a turn-key vacation rental

  Jamie Caudill Lokation Real Estate

  701 Spanish Main Dr Unit 512, Cudjoe Key, FL 33042
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  /50

  $550,000

  Sold Jul 14, 2025

  701 Spanish Main Dr Unit 631, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft
  • Built 2021

  Last Sold Summary

  • 18% Below List Price
  • $637/SF
  • 245 Days On Market

  Last Listing Agent Joe Sappington Waterfront Keys Realty Inc.

  701 Spanish Main Dr Unit 631, Cudjoe Key, FL 33042

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