Summerland Key, FL Homes

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  /49

  $1,150,000

  • 2 Beds
  • 2 Baths
  • 1,260 Sq Ft

  110 Doubloon Ln, Summerland Key, FL 33042

  Welcome to island life--this charming 2-bedroom, 2-bath waterfront cottage captures everything we love about the Florida Keys. Tucked on a desirable corner lot with canals on two sides, the property offers exceptional privacy, sea breezes, and inviting views from multiple vantage points. Inside, the home is bright, fresh, and thoughtfully updated, featuring a crisp white kitchen with quartz

  

  Sandra Tuttle

  Island Welcome Real Estate

  (786) 957-4255

  110 Doubloon Ln, Summerland Key, FL 33042
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  /40

  $950,000 Sold Sep 17, 2025

  17126 Wahoo Ln W, Sugarloaf Shores, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1977

  Last Sold Summary

  • 16% Below List Price
  • $825/SF
  • 85 Days On Market

  Current Estimated Value $982,007

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  17126 Wahoo Ln W, Sugarloaf Shores, FL 33042
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  /2

  Est $890,035 Not Listed For Sale

  460 Les Rohde Dr, Ramrod Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft
  • Built 2017

  460 Les Rohde Dr, Ramrod Key, FL 33042

  Last Sold Summary

  • 8% Below List Price
  • $748/SF

  Last Sold Price $970,000

  Last Listing Agent Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)
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  /92

  $3,799,000 Pending

  • 3 Beds
  • 3 Baths
  • 1,728 Sq Ft

  493 Coral Ave, Summerland Key, FL 33042

  There are homes in the Florida Keys... and then there are legacy properties. Conceived and built by internationally recognized Keys architect Glenn Gray as his personal residence, 493 Coral Avenue is a rare architectural offering positioned on a premier point lot with open Gulf frontage and protected canal dockage. With water on two sides and panoramic sunrise-to-sunset views, the setting is

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (645) 300-3164

  493 Coral Ave, Summerland Key, FL 33042
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  /53

  $2,725,000 Sold Mar 11, 2026

  1147 Flagship Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 2,058 Sq Ft
  • Built 1997

  Last Sold Summary

  • 6% Below List Price
  • $1,324/SF
  • 103 Days On Market

  Current Estimated Value $2,561,769

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  1147 Flagship Dr, Summerland Key, FL 33042
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  /2

  Est $1,164,687 Not Listed For Sale

  29663 Saratoga Ave, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,508 Sq Ft
  • Built 2023

  29663 Saratoga Ave, Big Pine Key, FL 33043

  Last Sold Summary

  • 27% Below List Price
  • $610/SF

  Last Sold Price $920,000

  Last Listing Agent Olivia Beck Meyer and Boumerhi Realty LLC
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  /59

  $599,000 New Construction

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft

  701 Spanish Main Dr Unit 29, Cudjoe Key, FL 33042

  Welcome to your piece of paradise in the exclusive gated community of Venture Out on Cudjoe Key. This stunning high-rise, built in 2024, embodies the perfect blend of modern luxury and island life. As you step inside, you are greeted by an inviting atmosphere that captures the essence of coastal living. The master bedroom boasts an en suite bathroom, offering a serene retreat at the end of the

  

  Ian Calderwood

  Bluescape Real Estate

  (786) 613-4762

  701 Spanish Main Dr Unit 29, Cudjoe Key, FL 33042
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  /2

  $185,000 Sold Mar 20, 2026

  1223 Rogers Ln, Cudjoe Key, FL 33042

  • Land

  Last Sold Summary

  • 0 Days On Market

  Current Estimated Value $287,661

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

  1223 Rogers Ln, Cudjoe Key, FL 33042
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  /2

  Est $276,038 Not Listed For Sale

  31380 Ave G, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,104 Sq Ft
  • Built 1971

  31380 Ave G, Big Pine Key, FL 33043

  Last Sold Summary

  • 15% Below List Price
  • $217/SF

  Last Sold Price $240,000

  Last Listing Agent Donna Halstead Coldwell Banker Schmitt RE Co.
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  /47

  $599,000 New Construction

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft

  701 Spanish Main Dr Unit 30, Cudjoe Key, FL 33042

  Welcome to your piece of paradise in the exclusive gated community of Venture Out on Cudjoe Key. This stunning high-rise, built in 2024, embodies the perfect blend of modern luxury and island life. As you step inside, you are greeted by an inviting atmosphere that captures the essence of coastal living. The master bedroom boasts an en suite bathroom, offering a serene retreat at the end of the

  

  Ian Calderwood

  Bluescape Real Estate

  (786) 613-4104

  701 Spanish Main Dr Unit 30, Cudjoe Key, FL 33042
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  /44

  $853,000 Sold Aug 12, 2025

  873 Indies Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,081 Sq Ft
  • Built 2002

  Last Sold Summary

  • 10% Below List Price
  • $789/SF
  • 123 Days On Market

  Current Estimated Value $876,715

  Last Listing Agent Donna Halstead Coldwell Banker Schmitt RE Co.

  873 Indies Rd, Summerland Key, FL 33042
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  /2

  Est $245,175 Not Listed For Sale

  31030 E Ave, Big Pine Key, FL 33043

  • 2 Beds
  • 1 Bath
  • 1,087 Sq Ft
  • Built 1974

  31030 E Ave, Big Pine Key, FL 33043

  Last Sold Summary

  • 14% Below List Price
  • $198/SF

  Last Sold Price $215,000

  Last Listing Agent Taron Wirth Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys
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  /22

  $465,000

  • 1 Bed
  • 1 Bath
  • 799 Sq Ft

  701 Spanish Main Dr Unit 455, Cudjoe Key, FL 33042

  A place to live, winter or Airbnb. Daily rentals allowed. Waterfront view down the canal. 17 ft seawall. Covered back patio for grilling or lounging. Front covered balcony. and back covered patio deck with mini sink, mini fridge & mini freezer. 1993' Manufactured home with Florida Room totaling 799 sq. ft. approx. 1 Bedroom w/a bonus room. Updated Bathroom with walk in shower, glass doors, hand

  Rose Dell Keller Williams Key West Compass Realty

  701 Spanish Main Dr Unit 455, Cudjoe Key, FL 33042
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  /29

  $510,000 Sold Apr 28, 2025

  1693 Bayview Dr, Little Torch Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 917 Sq Ft
  • Built 1976

  Last Sold Summary

  • 13% Below List Price
  • $556/SF
  • 60 Days On Market

  Last Listing Agent Ana Tey-Guerra Trexy International Realty, Inc

  1693 Bayview Dr, Little Torch Key, FL 33042
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  /6

  Not Listed For Sale

  31450 Avenue C, Big Pine Key, FL 33043

  • 2 Beds
  • 1 Bath
  • 480 Sq Ft
  • Built 1963

  31450 Avenue C, Big Pine Key, FL 33043

  Last Sold Summary

  • $490/SF
  • 19 Days On Market

  Last Sold Price $235,000

  Last Listing Agent Kirksten Irick Preferred Properties (KW)
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  /26

  $550,000

  • 3 Beds
  • 2 Baths
  • 960 Sq Ft

  31171 Avenue H, Big Pine Key, FL 33043

  Big Pine Key Here's your opportunity to get into a 3 Bedroom. 2 Bath stilt home in the Keys. Metal Roof. Brand New Central A/C & Heat. Sliding door from house to Covered Porch. Garage and Storage, downstairs, Concrete Patio. Back yard has concrete slab for a storage shed. Sewer has been connected and paid for in full. Fenced. Easement behind fence line between this home and back neighbor. For

  Rose Dell Keller Williams Key West Compass Realty

  31171 Avenue H, Big Pine Key, FL 33043
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  /45

  $819,000 Sold May 19, 2025

  25093 Center St, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,584 Sq Ft
  • Built 1958

  Last Sold Summary

  • 2% Below List Price
  • $517/SF
  • 18 Days On Market

  Current Estimated Value $817,108

  Last Listing Agent Susan Hawkinson Bascom Grooms Real Estate (KW)

  25093 Center St, Summerland Key, FL 33042
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  /2

  Est $245,968 Not Listed For Sale

  27328 St Vincent Ln, Ramrod Key, FL 33042

  • Studio

  27328 St Vincent Ln, Ramrod Key, FL 33042

  Last Sold Summary

  • 92% Below List Price

  Last Sold Price $128,000

  Last Listing Agent Brian Kruszewski LoKation Real Estate
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  /30

  $430,000

  • 2 Beds
  • 1 Bath
  • 415 Sq Ft

  21857 Disturbed Pine Rd, Summerland Key, FL 33042

  Acre Property! I've heard it said privacy is the ultimate luxury. Your Keys bungalow in the woods with a separate screened porch enclosure 13 X 18 plus a storge room 9 X 12. Connected to the house by a wood deck walkway. Artist retreat, man cave or maybe just because you love privacy and want an escape. Lots of potential. Are you handy! Additionally, there are 2 carports, Multiple storage areas.

  Rose Dell Keller Williams Key West Compass Realty

  21857 Disturbed Pine Rd, Summerland Key, FL 33042
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  /31

  $925,000 Sold Jan 30, 2026

  29178 Guava Ln, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,536 Sq Ft
  • Built 1982

  Last Sold Summary

  • 3% Below List Price
  • $602/SF
  • 5 Days On Market

  Current Estimated Value $934,774

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

  29178 Guava Ln, Big Pine Key, FL 33043
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  /49

  Est $441,520 Not Listed For Sale

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

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

  Last Sold Summary

  • 28% Above List Price
  • 27 Days On Market

  Last Sold Price $345,000

  Last Listing Agent PATRICIA BRUMMER Waterfront Keys Realty Inc.
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  /62

  $2,599,000

  • 3 Beds
  • 2 Baths
  • 2,224 Sq Ft

  16843 E Point Dr, Summerland Key, FL 33042

  Welcome to your private waterfront retreat in the highly sought-after Southpoint neighborhood of Sugarloaf Key - where space, privacy and effortless access to the open water redefine the Lower Keys Lifestyle.Positioned along a crystal clear canal just moments from the Bay, this elevated residence offers over 2200 sq.ft of thoughtfully designed living space, featuring three spacious bedrooms and

  Suzanne Moore Suzanne Moore Real Estate

  16843 E Point Dr, Summerland Key, FL 33042
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  /18

  $480,000 Sold Apr 01, 2026

  701 Spanish Main Dr Unit 384, Cudjoe Key, FL 33042

  • Land

  Last Sold Summary

  • 20% Below List Price
  • 126 Days On Market

  Current Estimated Value $522,715

  Last Listing Agent The Spottswood Team Truman & Co. (KW)

  701 Spanish Main Dr Unit 384, Cudjoe Key, FL 33042
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  /8

  Est $538,754 Not Listed For Sale

  17256 Keystone Rd, Sugarloaf Key, FL 33042

  17256 Keystone Rd, Sugarloaf Key, FL 33042

  Last Sold Summary

  • 44% Above List Price
  • 248 Days On Market

  Last Sold Price $375,000

  Last Listing Agent Al Barbosa One Sotheby's International Realty
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  /32

  $975,000

  • 4 Beds
  • 3 Baths
  • 2,503 Sq Ft

  30451 Hibiscus Ln, Big Pine Key, FL 33043

  ONE-OF-A-KIND! Custom-built home '2010'on a large 125 X 250 property, 31,250 sq. ft. more than 1/2 acre. 4bd/3bth plus a bonus room for a total 2493 sqft. Perfect for 2 working professionals from home or a big family. Good size bedrooms. 2 are ensuite. Separate Kitchen Dining & Living Room and an extra room for office or hobbies, gym or guest. Concrete slab under house same size of house so lots

  Rose Dell Keller Williams Key West Compass Realty

  30451 Hibiscus Ln, Big Pine Key, FL 33043
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  /35

  $629,500 Sold Sep 30, 2025

  31463 Avenue A, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • Built 2007

  Last Sold Summary

  • 3% Below List Price
  • $484/SF
  • 24 Days On Market

  Current Estimated Value $626,738

  Last Listing Agent Ryan Gernaat Coldwell Banker Schmitt Lower Keys (KW)

  31463 Avenue A, Big Pine Key, FL 33043
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  /2

  Est $1,031,273 Not Listed For Sale

  783 Pirates Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft
  • Built 2017

  783 Pirates Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 3% Below List Price
  • $842/SF

  Last Sold Price $1,000,000

  Last Listing Agent Stacy Shahan Island Real Estate Company Florida Keys
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  /26

  $550,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,088 Sq Ft

  31071 E Ave, Big Pine Key, FL 33043

  2005'' 3 Bedroom 2 Bath Modular home. Nice big columns. 50 X 100 lot. 12/14/2017 Metal roof with peel & stick underlayment 5v crimp. 8 X 24 covered porch with 2 sets of sliding doors off dining and living room. bay window in the Kitchen. Porch faces south with no homes across the street. 288 sq.ft legal permitted storage enclosure. Concrete slab. 14.97 ft above base flood. Buyer to verify any

  Rose Dell Keller Williams Key West Compass Realty

  31071 E Ave, Big Pine Key, FL 33043
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  /34

  $580,000 Sold Sep 15, 2025

  30868 Malaga Ln, Big Pine Key, FL 33043

  • 3 Beds
  • 1 Bath
  • 1,080 Sq Ft
  • Built 1972

  Last Sold Summary

  • 3% Below List Price
  • $537/SF
  • 137 Days On Market

  Current Estimated Value $620,611

  Last Listing Agent Loren Rea Truman & Co. (KW)

  30868 Malaga Ln, Big Pine Key, FL 33043
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  /2

  Est $800,327 Not Listed For Sale

  29654 Constitution Ave, Big Pine Key, FL 33043

  • 4 Beds
  • 2 Baths
  • 1,547 Sq Ft
  • Built 1963

  29654 Constitution Ave, Big Pine Key, FL 33043

  Last Sold Summary

  • 1% Below List Price
  • $510/SF

  Last Sold Price $789,000

  Last Listing Agent Frank Griffiths Lokation Real Estate
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  /29

  $800,000

  • 2 Beds
  • 2 Baths
  • 1,162 Sq Ft

  28452 Yucatan Ln, Summerland Key, FL 33042

  SATURDAY 28TH OPEN HOUSE 10AM-1PM Canal front home with quick exit out of the canal to Pine Channel for Atlantic or Gulf access. 7200 sq.ft. lot. Back yard big enough for a pool. Pack your toothbrush and your ready for your salt life to begin. Being sold mostly furnished 2bd/2bth 1162 sq.ft. Home, plus, southerly facing screen porch, which has accordian shutters,porch faces back yard and canal.

  Rose Dell Keller Williams Key West Compass Realty

  28452 Yucatan Ln, Summerland Key, FL 33042
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  /51

  $1,200,000 Sold Jun 16, 2025

  1060 W Shore Dr, Big Pine Key, FL 33043

  • 3 Beds
  • 2.5 Baths
  • 2,137 Sq Ft
  • Built 1977

  Last Sold Summary

  • 23% Below List Price
  • $562/SF
  • 26 Days On Market

  Current Estimated Value $1,340,996

  Last Listing Agent Elizabeth Greco-DeGrenier Coldwell Banker Schmitt RE Co.

  1060 W Shore Dr, Big Pine Key, FL 33043
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  /2

  Est $695,788 Not Listed For Sale

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

  • 2 Beds
  • 1 Bath
  • 990 Sq Ft
  • Built 1977

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

  Last Sold Summary

  • 7% Below List Price
  • $659/SF

  Last Sold Price $652,410
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  /107

  $2,999,000 New Construction

  • 3 Beds
  • 3.5 Baths
  • 2,538 Sq Ft

  747 La Fitte Rd, Summerland Key, FL 33042

  Spectacular open water location, with fabulous views from this newly constructed well-built oceanfront concrete home. Direct ocean or gulf access from massive dock that includes three boat lifts (one 15,000 pound, one 12,000 pound and a 10,000 pound double Waverunner lift). Relax in a large heated/chilled inground pool with a big covered pool patio area which drinks in the Ocean view. Home is

  John L. Markle Keller Williams Realty Premier Properties - Kendall

  747 La Fitte Rd, Summerland Key, FL 33042
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  /40

  $640,000 Sold Sep 15, 2025

  3806 Dyer Rd, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 912 Sq Ft
  • Built 1990

  Last Sold Summary

  • 8% Below List Price
  • $702/SF
  • 54 Days On Market

  Current Estimated Value $663,700

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

  3806 Dyer Rd, Big Pine Key, FL 33043
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  /37

  Est $1,635,613 Not Listed For Sale

  2256 Matthews Rd, Big Pine Key, FL 33043

  • 4 Beds
  • 3 Baths
  • 2,000 Sq Ft
  • Built 2024

  2256 Matthews Rd, Big Pine Key, FL 33043

  Last Sold Summary

  • 4% Below List Price
  • $850/SF
  • 5 Days On Market

  Last Sold Price $1,700,000

  Last Listing Agent Greg MacLaren Internet Realty of the Florida Keys
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  /39

  $499,000

  • 2 Beds
  • 2 Baths
  • 618 Sq Ft

  701 Spanish Main Dr Unit 411, Cudjoe Key, FL 33042

  Affordable waterfront Living in the Lower Keys! This waterfront 2-bedroom, 2-bath mobile home is located in Venture Out, a gated, resort-style community offering endless activities and true Island living at a price point rarely found on the water.Enjoy direct boating to open water, just minutes from the Atlantic and Gulf, making this a boaters dream. Located at Mile Marker 23, you're only 20

  Suzanne Moore Suzanne Moore Real Estate

  701 Spanish Main Dr Unit 411, Cudjoe Key, FL 33042
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  /57

  $925,000 Sold Mar 13, 2026

  2123 Spanish Channel Dr, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,185 Sq Ft
  • Built 1991

  Last Sold Summary

  • 6% Below List Price
  • $781/SF
  • 49 Days On Market

  Current Estimated Value $954,843

  Last Listing Agent Anne Press Lokation Real Estate

  2123 Spanish Channel Dr, 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

  Last Sold Summary

  Last Sold Price $525,000

  Last Listing Agent Kieran Mahoney Sugarloaf Realty LLC
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  /38

  $830,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,513 Sq Ft

  30471 Coconut Hwy, Big Pine Key, FL 33043

  Experience the charm of this beautifully renovated split-level home, designed with privacy and elegance in mind. The elevated master suite ensures a peaceful retreat, while additional spaces offer the versatile of an office or separate family room perfect for relaxation or entertaining. Step through the bedroom doors onto a spacious deck, where you can enjoy views of the meticulously landscaped

  Richard Haskins Buy The Keys

  30471 Coconut Hwy, Big Pine Key, FL 33043

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