Summerland Key, FL Homes

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  /41

  $800,000

  • Land

  33000 Old State Road 4a, No Name Key, FL 33043

  YOU CAN HELP SAVE THE FLORIDA KEYS REEFS..!!THIS 20 ACRE PARCEL WITH A 17 ACRE SALTWATER LAKE WAS RECENTLY MARKETED AS A PRIVATE LAKE FOR PERSONAL USE. IT MAY STILL BE USED FOR THAT. THIS PROPERTY CANNOT BE DEVELOPED...!!!! NO HOME, NO COMMERCIAL USE. HOWEVER IN RECENT MONTHS RESEARCHERS FROM FLORIDA INTERNATIONAL UNIVERSITY HAVE BEEN STUDYING THE GROWTH OF SPIDER CRABS THAT

  Tony Paterniti Tony Paterniti

  33000 Old State Road 4a, No Name Key, FL 33043
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  /42

  $550,000 Sold Dec 01, 2025

  27213 Old State Road 4a Unit 4a, Summerland Key, FL 33042

  • 4 Beds
  • 2 Baths
  • 864 Sq Ft
  • Built 1984

  Last Sold Summary

  • 19% Below List Price
  • $637/SF
  • 125 Days On Market

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

  27213 Old State Road 4a Unit 4a, Summerland Key, FL 33042
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  /49

  Est $350,899 Not Listed For Sale

  701 Spanish Main Dr Unit 557, Cudjoe Key, FL 33042

  701 Spanish Main Dr Unit 557, Cudjoe Key, FL 33042
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  /60

  $1,490,000 New Construction

  • 4 Beds
  • 3 Baths
  • 2,120 Sq Ft

  27433 Antigua Rd, Summerland Key, FL 33042

  NEW CONSTRUCTION POOL HOME - COMPLETED 2025 & MOVE-IN READY!Welcome to your brand-new coastal retreat on Ramrod Key. This luxury 4-bedroom, 3-bath residence delivers world-class construction, refined finishes, and effortless indoor-outdoor living in one of the most desirable boating neighborhoods in the Lower Keys.Built with solid CBS construction, a metal roof, and impact-rated windows & doors,

  Kelly Gardner Bluescape Real Estate

  27433 Antigua Rd, Summerland Key, FL 33042
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  /28

  $500,000 Sold Jun 20, 2025

  30952 Baileys Ln, Big Pine Key, FL 33043

  • 2 Beds
  • 1 Bath
  • 575 Sq Ft
  • Built 1958

  Last Sold Summary

  • 13% Below List Price
  • $870/SF
  • 18 Days On Market

  Current Estimated Value $517,464

  Last Listing Agent Joyce Craul Expert Realty LLC (HQ)

  30952 Baileys Ln, Big Pine Key, FL 33043
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  /8

  Est $451,836 Not Listed For Sale

  17256 Keystone Rd, Sugarloaf Key, FL 33042

  17256 Keystone Rd, Sugarloaf Key, FL 33042
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  /25

  $629,500

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

  31243 E Ave E, Big Pine Key, FL 33043

  **Price Enhancement* 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, a small, fenced area provides a safe and convenient space for

  Sabre Mendoza Coldwell Banker Schmitt RE Co.

  31243 E Ave E, Big Pine Key, FL 33043
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  /11

  $231,000 Sold Sep 25, 2025

  30887 Hammock Dr, Big Pine Key, FL 33043

  • 1 Bed
  • 1 Bath
  • 482 Sq Ft
  • Built 1966

  Last Sold Summary

  • 18% Below List Price
  • $479/SF
  • 225 Days On Market

  Last Listing Agent Rose Dell Keller Williams Key West Compass Realty

  30887 Hammock Dr, Big Pine Key, FL 33043
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  /2

  Est $1,053,435 Not Listed For Sale

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

  783 Pirates Rd, Summerland Key, FL 33042

  783 Pirates Rd, Summerland Key, FL 33042
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  /88

  $750,000

  • 3 Beds
  • 2 Baths
  • 1,056 Sq Ft

  40 Munson Ave, Summerland Key, FL 33042

  Welcome home to your peaceful island retreat! This stunning 3-bed, 2-bath home is move-in ready & full of charm. Enjoy soaring vaulted ceilings, an open layout, & a bright kitchen with Quartz countertops, stainless steel appliances, & large island with ample seating. Recent updates include new luxury vinyl plank flooring, new upgraded refrigerator, & new outdoor bar & sitting area perfect for

  Lindsay Ryan EXP Realty LLC

  40 Munson Ave, Summerland Key, FL 33042
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  /16

  $165,000 Sold Feb 24, 2025

  8 Calico Jack Cir, Cudjoe Key, FL 33042

  • Land

  Last Sold Summary

  • 8% Below List Price
  • 212 Days On Market

  Last Listing Agent Beata Sharpe Coldwell Banker Vanguard Realty

  8 Calico Jack Cir, Cudjoe Key, FL 33042
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  /2

  Est $772,973 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,547 Sq Ft

  29654 Constitution Ave, Big Pine Key, FL 33043

  29654 Constitution Ave, Big Pine Key, FL 33043
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  /60

  $949,900

  • 3 Beds
  • 2 Baths
  • 1,288 Sq Ft

  27405 Guadaloupe Ln, Summerland Key, FL 33042

  Soak up the Keys lifestyle from this bright, modern 3-bed/2-bath home in the coveted oceanside community of Breezeswept Beach Estates on Ramrod Key. Built in 2008 with high-end finishes--sleek cabinetry, quality flooring, and fresh, airy decor--this turnkey residence is neat, clean, and move-in ready.Outdoor living shines here: two open decks (front and back) capture breezes and sunset glow,

  Mark Gable Engel & Volkers Marathon

  27405 Guadaloupe Ln, Summerland Key, FL 33042
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  /17

  $395,000 Sold Sep 22, 2025

  10W Cooks Unit B, Cook Island Key, FL 33043

  • 2 Beds
  • 1 Bath
  • 596 Sq Ft
  • Built 1948

  Last Sold Summary

  • 12% Below List Price
  • $663/SF
  • 13 Days On Market

  Current Estimated Value $398,000

  Last Listing Agent Greg Gordon Island Home Realty Inc.

  10W Cooks Unit B, Cook Island Key, FL 33043
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  /2

  Est $449,078 Not Listed For Sale

  • Studio

  24397 W Caribbean Dr, Summerland Key, FL 33042

  24397 W Caribbean Dr, Summerland Key, FL 33042
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  /39

  $699,000

  • 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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  /40

  $1,175,000 Sold Mar 24, 2025

  29541 Flying Cloud Ave, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 988 Sq Ft
  • Built 1988

  Last Sold Summary

  • 19% Below List Price
  • $1,189/SF
  • 134 Days On Market

  Current Estimated Value $1,161,342

  Last Listing Agent Nira Tocco Coldwell Banker Schmitt RE Co.

  29541 Flying Cloud Ave, Big Pine Key, FL 33043
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  /2

  Est $724,874 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 990 Sq Ft

  1313 State Rd Unit 4A, Little Torch Key, FL 33042

  1313 State Rd Unit 4A, Little Torch Key, FL 33042
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  /54

  $1,900,000

  • 4 Beds
  • 3 Baths
  • 1,440 Sq Ft

  1082 Bay Dr, Summerland Key, FL 33042

  Rare Yacht-Ready Waterfront? It doesn't get better than this in the Lower Florida Keys! Embraced by the emerald waters of the American Caribbean, pristine, wide and flow-through canals, and nearly 200 feet of concrete seawall sits this extraordinary opportunity to own prime waterfront. A prized combination coveted by the most discerning boating enthusiasts. Sitting on an oversized 7,900 sq. ft.

  Angelina Will Berkshire Hathaway HomeServices Knight & Gardner Realty

  1082 Bay Dr, Summerland Key, FL 33042
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  /53

  $900,000 Sold Oct 15, 2025

  31507 Avenue E, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,140 Sq Ft
  • Built 2017

  Last Sold Summary

  • 8% Below List Price
  • $789/SF
  • 120 Days On Market

  Last Listing Agent Lisa Frins Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

  31507 Avenue E, Big Pine Key, FL 33043
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  /37

  Est $1,323,997 Not Listed For Sale

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

  2256 Matthews Rd, Big Pine Key, FL 33043

  2256 Matthews Rd, Big Pine Key, FL 33043
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  /59

  $1,569,999 New Construction

  • 4 Beds
  • 3 Baths
  • 2,136 Sq Ft

  142 Peg Leg Ln, Cudjoe Key, FL 33042

  Welcome to your dream coastal retreat! Perched on concrete stilts with sweeping views, this newer 4-bedroom, 3-bath luxury home offers the perfect blend of island elegance and modern comfort. Two spacious master suites provide privacy and flexibility, while the open-concept living space is framed by wide, breezy balconies -- ideal for soaking in the sunrise or entertaining guests in true Keys

  Alejandro Perez Amerifirst Realty

  142 Peg Leg Ln, Cudjoe Key, FL 33042
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  /54

  $915,000 Sold Aug 19, 2025

  29737 Newfound Blvd, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1978

  Last Sold Summary

  • 8% Below List Price
  • $866/SF
  • 33 Days On Market

  Current Estimated Value $945,151

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

  29737 Newfound Blvd, Big Pine Key, FL 33043
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  /2

  Not Listed For Sale

  23008 Overseas Hwy, Cudjoe Key, FL 33042

  23008 Overseas Hwy, Cudjoe Key, FL 33042
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  /8

  $120,000

  • Land

  Lot 6 Vacant Land, Big Pine Key, FL 33043

  Positioned just off US-1 (Jimmy Buffett Memorial Highway), this parcel of land benefits from excellent visibility and accessibility, supporting a wide variety of potential commercial uses.Potential for securing valuable ROGO points for future permitting needs in Monroe County (buyer to verify the number of ROGO points with the County).

  Austin Kimbler Expert Realty LLC (HQ)

  Lot 6 Vacant Land, Big Pine Key, FL 33043
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  /27

  $1,900,000 Sold Jun 18, 2025

  17022 Starfish Ln W, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,990 Sq Ft
  • Built 1994

  Last Sold Summary

  • 14% Below List Price
  • $955/SF
  • 85 Days On Market

  Current Estimated Value $1,910,354

  Last Listing Agent Kieran Mahoney Sugarloaf Realty LLC

  17022 Starfish Ln W, Summerland Key, FL 33042
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  /2

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 925 Sq Ft

  1669 Pine Channel Dr, Little Torch Key, FL 33042

  1669 Pine Channel Dr, Little Torch Key, FL 33042
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  /61

  $615,000 Under Contract

  • 2 Beds
  • 2 Baths
  • 912 Sq Ft

  29951 Pine Channel Rd, Big Pine Key, FL 33043

  VA Assumable 2.625% interest rate for eligible Buyers! Total current payment $2864/mo! Inquire for more details.Welcome to your island escape! This beautifully updated 2 bedroom, 2 full bath stilted home offers the perfect blend of comfort, convenience, & coastal charm. Situated on a spacious lot in the heart of Big Pine Key, this property features a brand new gas stove, new AC, new quartz

  Lindsay Ryan EXP Realty LLC

  29951 Pine Channel Rd, Big Pine Key, FL 33043
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  /60

  $2,512,500 Sold Oct 31, 2025

  1260 Sugarloaf Blvd, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,886 Sq Ft
  • Built 1991

  Last Sold Summary

  • 3% Below List Price
  • $871/SF
  • 60 Days On Market

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

  1260 Sugarloaf Blvd, Summerland Key, FL 33042
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  /4

  Est $237,914 Not Listed For Sale

  • 2 Beds

  31373 Avenue C, Big Pine Key, FL 33043

  31373 Avenue C, Big Pine Key, FL 33043
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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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  /58

  $2,025,000 Sold May 13, 2025

  22440 Jolly Roger Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,292 Sq Ft
  • Built 1988

  Last Sold Summary

  • 12% Below List Price
  • $1,567/SF
  • 85 Days On Market

  Current Estimated Value $1,989,947

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  22440 Jolly Roger Dr, Summerland Key, FL 33042
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  /28

  Est $1,074,024 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,988 Sq Ft

  27385 St Lucie Ln, Ramrod Key, FL 33042

  27385 St Lucie Ln, Ramrod 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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  /37

  $540,000 Sold Mar 04, 2025

  27883 Coral Shores Rd, Little Torch Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 720 Sq Ft
  • Built 1973

  Last Sold Summary

  • 2% Below List Price
  • $750/SF
  • 9 Days On Market

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

  27883 Coral Shores Rd, Little Torch Key, FL 33042
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  /2

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 732 Sq Ft

  31119 Avenue I, Big Pine Key, FL 33043

  31119 Avenue I, Big Pine Key, FL 33043
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  /30

  $362,000

  • 3 Beds
  • 1 Bath
  • 1,044 Sq Ft

  27960 Porgie Path, Little Torch Key, FL 33042

  Canal Front Coral Shores Estates! This 3 Bedroom home with Open Water views of South Pine Channel has a wonderful Swimming Canal ,perfect for kayaking, SUP, and can be easily accessed from the beautiful large new deck- with ladder access to the water. The front of the yard has new fencing, and room to park several cars off street. The inside has 3 bedrooms and a bath, and 2 living room areas.

  Elaine Coyle Keller Williams Key West Compass Realty

  27960 Porgie Path, Little Torch Key, FL 33042
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  /32

  $635,000 Sold Apr 25, 2025

  2682 Koehns Ave, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 1963

  Last Sold Summary

  • 2% Below List Price
  • $509/SF
  • 12 Days On Market

  Current Estimated Value $630,991

  Last Listing Agent Sean Farrer Coldwell Banker Schmitt Real Estate Co. (KW)

  2682 Koehns Ave, Big Pine Key, FL 33043
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  /2

  Est $854,289 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 1,792 Sq Ft

  29664 & 29670 Constitution Ave, Big Pine Key, FL 33040

  29664 & 29670 Constitution Ave, Big Pine Key, FL 33040
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  /7

  $4,325,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 3,119 Sq Ft

  231 E Shore Dr Unit 7, Summerland Key, FL 33042

  Introducing Seven Palms Cove, a one-of-a-kind new construction community redefining luxury island living in the Florida Keys. With only seven exclusive oceanfront residences starting at $4M, this private, gated enclave offers an extraordinary opportunity to own a slice of paradise just minutes from Key West.Each home spans over 4,000 sq. ft. with 5 bedrooms, 5.5 bathrooms, and open-concept

  Stephanie Muzzillo Serhant Florida LLC - Delray Beach Office

  231 E Shore Dr Unit 7, Summerland Key, FL 33042

Showing Results 281 - 320, Page 8 of 18