Summerland Key, FL Homes

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  $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 $884,684

  Last Listing Agent Alexa Morgan Buy The Keys

  17338 Dolphin St E, Summerland Key, FL 33042
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  /2

  Est $1,058,680 Not Listed For Sale

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

  29552 Independence Ave, Big Pine Key, FL 33043

  29552 Independence Ave, Big Pine Key, FL 33043
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  /10

  $335,000

  • Land

  0 Indies Rd, Ramrod Key, FL 33042

  Waterfront vacant lot located on Ramrod Key in an established canal community on the oceanside of the Lower Keys. This property offers boating access to the Atlantic with connectivity to Florida Bay. No building permit is currently in place; buyers may pursue development through ROGO or obtain a separate building right. Conveniently situated between Marathon and Key West, offering easy access to

  Jenifer Hirsch Bluescape Real Estate

  0 Indies Rd, Ramrod Key, FL 33042
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  /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 $352,721

  Last Listing Agent Kirksten Irick Preferred Properties (KW)

  31456 Ave F, Big Pine Key, FL 33043
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  /40

  Est $687,914 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  29366 Lucrecia St, Big Pine Key, FL 33043

  29366 Lucrecia St, Big Pine Key, FL 33043
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  /34

  $699,000

  • 3 Beds
  • 1.5 Baths
  • 1,247 Sq Ft

  29283 Coconut Palm Dr, Big Pine Key, FL 33043

  Welcome to Coconut Palm Drive -- a hidden gem in one of Big Pine Key's peaceful residential neighborhoods. This 3-bedroom, 1.5-bath island home offers vaulted ceilings, crown molding, and an open-concept layout that brings in natural light and a spacious feel. The tropical backyard is fully fenced for privacy and features mature banana trees. A generous downstairs storage area offers endless

  Stephany Duvall Engel & Volkers Marathon

  29283 Coconut Palm Dr, Big Pine Key, FL 33043
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  /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 $1,075,962

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

  128 Le Grand Ln, Summerland Key, FL 33042
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  /42

  Est $1,249,379 Not Listed For Sale

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

  31040 Atlantis Dr, Big Pine Key, FL 33043

  31040 Atlantis Dr, Big Pine Key, FL 33043
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  /4

  $300,000

  • Land

  27426 Martinique Ln, Summerland Key, FL 33042

  Vacant 6,000 SF lot in desirable Ramrod Key, ideally positioned near the world-class Looe Key Reef and just a five-minute boat ride to Picnic Island. This property offers an exceptional opportunity to build in one of the Lower Keys' most sought-after lifestyle locations. Walking distance to local favorites including The Tiki Bar and Boondocks Grille & Draft House. Buyer to obtain building permit

  Kasey Fey Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

  27426 Martinique Ln, Summerland Key, FL 33042
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  /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 $520,769

  Last Listing Agent Rose Dell Keller Williams Key West Compass Realty

  31232 Ave d, Big Pine Key, FL 33043
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  /46

  Est $2,685,531 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 2,371 Sq Ft

  661 Sugarloaf Blvd, Summerland Key, FL 33042

  661 Sugarloaf Blvd, Summerland Key, FL 33042
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  /12

  $599,000

  • Land
  • 0.27 Acre
  • $2,183,468 per Acre

  16841 Driftwood Ln, Sugarloaf Shores, FL 33042

  **Tier III Beautiful Buildable Canal Front Lot in Sugarloaf Shores!**Discover an exceptional opportunity in the prestigious Sugarloaf Shores neighborhood with this oversized canal front lot, boasting 11,950 square feet. This prime piece of real estate offers quick boating access to both the Gulf of Mexico and the Atlantic Ocean.Key features include:- **Unparalleled Location:** Just 14 miles from

  Daiane Sardinas Carvalho Centennial Realty Group, LLC

  16841 Driftwood Ln, Sugarloaf Shores, FL 33042
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  /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 $946,029

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

  763 Diane Ave, Little Torch Key, FL 33042
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  /2

  Est $1,066,212 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,390 Sq Ft

  467 Almond Ln, Big Pine Key, FL 33043

  467 Almond Ln, Big Pine Key, FL 33043
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  /28

  $1,950,000

  • 3 Beds
  • 3 Baths
  • 1,797 Sq Ft

  860 Lagoon Dr, Summerland Key, FL 33042

  This stately concrete home has all the best of everything on one of the best boating areas in the Lower KeysThis home is being offered completely furnished with electronics & most of the artwork, All kitchen and bedding items. The large great room has lots of seating. with soaring ceilings and lots of natural light. The kitchen is a chef's delight with sub zero appliances and induction chef's

  Cheryl Moses Action Keys Realty of the Lower FL Keys LLC

  860 Lagoon Dr, Summerland Key, FL 33042
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  /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

  Last Listing Agent Natallie Liz Expert Realty LLC (HQ)

  726 Jamaica Ln, Summerland Key, FL 33042
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  /46

  Est $1,271,308 Not Listed For Sale

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

  137 Caribbean Dr E, Summerland Key, FL 33042

  137 Caribbean Dr E, Summerland Key, FL 33042
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  /65

  $1,099,000

  • 4 Beds
  • 3 Baths
  • 2,448 Sq Ft

  165 Cutlass Ln, Summerland Key, FL 33042

  Discover Your Dream Waterfront Home in the Florida Keys! This stunning canal-front residence boasts 4 spacious bedrooms and 3 bathrooms. With 2,448 sq. ft. of thoughtfully laid-out living space, this home is perfect for accommodating large families and entertaining guests.Step onto the expansive covered balconies on both floors, where you can relax and take in the serene canal views. The generous

  Justyn Ewald Expert Realty LLC (HQ)

  165 Cutlass Ln, Summerland Key, FL 33042
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  /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
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  /36

  Est $2,481,670 Not Listed For Sale

  • 4 Beds
  • 5.5 Baths
  • 3,224 Sq Ft

  333 Indies Rd, Ramrod Key, FL 33042

  333 Indies Rd, Ramrod Key, FL 33042
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  /50

  $2,500,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,000 Sq Ft

  711 W Indies Dr, Summerland Key, FL 33042

  Stunning Brand New Open Water CBS Construction Home on beautiful Ramrod Key, FL. Minutes to the Atlantic Ocean and World Famous Looe Key the #1 Dive destination in the Continental US.Discover coastal living at its finest with this brand-new 4-bedroom, 3-bathroom home nestled on the sparkling open waters of Ramrod Key. Boasting 2,000 square feet of thoughtfully designed living space, this home

  Greg MacLaren Internet Realty of the Florida Keys

  711 W Indies Dr, Summerland Key, FL 33042
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  /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 $1,108,592

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

  28552 Maracaibo Rd, Little Torch Key, FL 33042
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  /26

  Est $787,118 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,794 Sq Ft

  30946 Edward Rd, Big Pine Key, FL 33043

  30946 Edward Rd, Big Pine Key, FL 33043
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  /40

  $925,000

  • 3 Beds
  • 2 Baths
  • 1,034 Sq Ft

  28571 Buccaneer Rd, Summerland Key, FL 33042

  Embrace the ultimate Keys lifestyle in this charming waterfront hone, where every day feels like a vacation. Located just minutes from ocean access no bridges, this property is a fisherman's paradiseThis 3-bedroom, 2-bath home offers Hardie board Siding metal roof an open floor plan. The newly updated kitchen features exquisite granite countertops, stainless steel appliances, and a large island

  Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

  28571 Buccaneer Rd, Summerland Key, FL 33042
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  /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 $767,851

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  1590 Gardenia Ln, Big Pine Key, FL 33043
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  /2

  Est $1,587,584 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  1931 Sugarloaf Blvd, Sugarloaf Key, FL 33042

  1931 Sugarloaf Blvd, Sugarloaf Key, FL 33042
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  /26

  $625,000

  • 3 Beds
  • 2 Baths
  • 1,353 Sq Ft

  29030 Iris Dr, Big Pine Key, FL 33043

  This 3BR spacious canal front home with quick open water access is nestled at the end of a quiet dead-end street. Amidst lush vegetation, this property offers the ultimate sanctuary for those seeking privacy and a connection to the Keys lifestyle. 50ft concrete seawall with 10,000lb boat lift. This home boasts an inviting shaded deck creating the perfect outdoor space for relaxation and

  Justyn Ewald Expert Realty LLC (HQ)

  29030 Iris Dr, Big Pine Key, FL 33043
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  /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 $783,998

  Last Listing Agent Walter Ceballos, P.A. Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

  22988 Port Royal Ln, Summerland Key, FL 33042
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  /2

  Est $913,994 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,326 Sq Ft

  22842 Buccaneer Ln, Summerland Key, FL 33042

  22842 Buccaneer Ln, Summerland Key, FL 33042
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  /2

  $324,999

  • 2 Beds
  • 2 Baths
  • 980 Sq Ft

  37 Yardarm Rd Unit 1, Cudjoe Key, FL 33042

  This sale is for one 6000 square foot lot with a home in need of repairs or replacement. The value of this property is in the ROGO EXEMPT status. All the utilities are there and I can give you clear title for this property upon closing.Adjacent to this property is lots #35 & 36. They are also available making a total parcel of 18,000 square feet.

  Joseph Ordini Keller Williams Key West Compass Realty

  37 Yardarm Rd Unit 1, Cudjoe Key, FL 33042
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  $2,500,000 Sold Jul 15, 2025

  943 Flagship Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,792 Sq Ft
  • Built 2001

  Last Sold Summary

  • 7% Below List Price
  • $1,395/SF
  • 121 Days On Market

  Current Estimated Value $2,511,481

  Last Listing Agent Lisa Swanson The Agency Florida Keys

  943 Flagship Dr, Summerland Key, FL 33042
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  /24

  Est $965,839 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,482 Sq Ft

  19453 Seminole St, Sugarloaf Key, FL 33042

  19453 Seminole St, Sugarloaf Key, FL 33042
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  /20

  $1,295,000

  • 4 Beds
  • 2 Baths
  • 1,820 Sq Ft

  29678 Enterprise Ave, Big Pine Key, FL 33043

  Discover an outstanding opportunity in Big Pine Key with this canal-front, stilted duplex featuring two spacious 2 bedroom 1 bath residences and deep-water boating access. This is an exceptional boater's duplex in Pine Channel Estates where you can enjoy income and lifestyle in one place. Enjoy 75 feet of concrete dockage with a convenient step-down and retaining wall, all situated on a clean,

  Thomas Carden Keys to the Coast Real Estate LLC

  29678 Enterprise Ave, Big Pine Key, FL 33043
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  /39

  $650,000 Sold Apr 25, 2025

  25161 Center St, Summerland Key, FL 33042

  • 1 Bed
  • 1.5 Baths
  • 1,024 Sq Ft
  • Built 1958

  Last Sold Summary

  • 4% Below List Price
  • $635/SF
  • 6 Days On Market

  Current Estimated Value $636,471

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

  25161 Center St, Summerland Key, FL 33042
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  /23

  Est $1,300,472 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
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  /61

  $1,795,000

  • 2 Beds
  • 2 Baths
  • 1,172 Sq Ft

  876 Gulf Dr, Summerland Key, FL 33042

  Coastal Haven in Summerland Key Cove Isles! Calling all boaters--this move-in-ready waterfront oasis sits on a premier deep-draft canal with quick access to both the Atlantic and Gulf! Extensively updated in 2025 with a new metal roof, spray foam insulation, interior and exterior paint, new LVP flooring, gutters, soffits, fascias, new pool deck, and Trex decking, this home radiates fresh coastal

  Lisa Swanson The Agency Florida Keys

  876 Gulf Dr, Summerland Key, FL 33042
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  /2

  $545,000 Sold May 22, 2025

  30276 Watson Blvd, Big Pine Key, FL 33043

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft
  • Built 1989

  Last Sold Summary

  • $631/SF
  • 0 Days On Market

  Current Estimated Value $544,526

  Last Listing Agent Ally Kelley Ocean Sotheby's International

  30276 Watson Blvd, Big Pine Key, FL 33043
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  /55

  Est $1,361,668 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
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  /2

  $115,000

  • Land
  • 1.27 Acres
  • $90,552 per Acre

  Lot 5 Mira Rd, Sugarloaf Key, FL 33042

  This lot is worth 4 points to be used towards obtaining a building permit in the ROGO system. Please contact Monroe County to verify information. Seller has several point lots for sale.

  Pamela Stangler Expert Realty LLC

  Lot 5 Mira Rd, Sugarloaf Key, FL 33042
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  /41

  $970,000 Sold May 27, 2025

  366 Sawyer Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,390 Sq Ft
  • Built 1988

  Last Sold Summary

  • 19% Below List Price
  • $698/SF
  • 4 Days On Market

  Current Estimated Value $1,004,635

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

  366 Sawyer Dr, Summerland Key, FL 33042

Showing Results 481 - 520, Page 13 of 18