Cudjoe Key, FL Homes

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  /34

  $1,575,000

  • 3 Beds
  • 2 Baths
  • 1,667 Sq Ft

  22865 Redfish Ln, Summerland Key, FL 33042

  The Best Boating Access in the Lower Keys, hands down!!! The 'Island Life' awaits you in this stunning well thought out custom designed canal front property. This solid CBS home, nestled in lush tropical landscaping, features 3 bedrooms and 2 baths on an oversized 10,200 sq.ft. lot located in the tranquil setting of sought after Cudjoe Ocean Shores. This subdivision is extremely desirable due to

  

  Anneliese Dietrick

  Coldwell Banker Schmitt Lower Keys (KW)

  (645) 241-6029

  22865 Redfish Ln, Summerland 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

  Not Listed For Sale

  1138 Basque Ln, Summerland Key, FL 33042

  • 7,000 Sq Ft

  1138 Basque Ln, Summerland Key, FL 33042

  Last Sold Summary

  • $10/SF

  Last Sold Price $70,000

  Last Listing Agent Jimmy Lane Island Life Realty Experts
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  /38

  $899,000

  • 3 Beds
  • 2 Baths
  • 1,203 Sq Ft

  153 Peg Leg Ln, Summerland Key, FL 33042

  Super quick ocean access and 60' of concrete dockage from this 3 Bedroom 2 Bath canal front home located just 2 canals over from open water! Plenty of room for all your toys in the oversized 2-Car Garage with overhead doors on both sides. Inside you will find an open floor plan leading out to a full-length Porch overlooking the water for morning coffee or evening cocktails with family and

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (833) 853-7147

  153 Peg Leg Ln, Summerland Key, FL 33042
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  /46

  $998,000 Sold Sep 09, 2025

  1117 Basque Ln, Cudjoe Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,318 Sq Ft
  • Built 2013

  Last Sold Summary

  • $757/SF
  • 16 Days On Market

  Current Estimated Value $1,011,653

  Last Listing Agent Lynn Goodwin Coldwell Banker Schmitt Real Estate Co.

  1117 Basque Ln, Cudjoe Key, FL 33042
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  /61

  Est $2,784,138 Not Listed For Sale

  20886 4th Ave W, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 3,042 Sq Ft
  • Built 2008

  20886 4th Ave W, Summerland Key, FL 33042

  Last Sold Summary

  • 4% Below List Price
  • $953/SF
  • 66 Days On Market

  Last Sold Price $2,900,000

  Last Listing Agent Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)
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  $2,995,000

  • 4 Beds
  • 3 Baths
  • 2,913 Sq Ft

  20920 5th Ave W, Summerland Key, FL 33042

  Florida Keys luxury island living at its finest. Welcome to your private slice of tropical island living in coveted Cudjoe Gardens--a true boater's dream set on an oversized double canal-front lot (approx. 15,200 sq. ft.) with an impressive close to 200 feet of concrete seawall. This beautifully designed CBS home offers 4 bedrooms, 3 baths, and nearly 3,000 sq. ft. of living space, thoughtfully

  

  Miriam Novotny

  Compass Florida, LLC

  (786) 667-5744

  20920 5th Ave W, Summerland Key, FL 33042
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  /42

  $1,750,000 Sold Feb 26, 2026

  20771 2nd Ave W, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 2,047 Sq Ft
  • Built 2010

  Last Sold Summary

  • 17% Below List Price
  • $855/SF
  • 161 Days On Market

  Current Estimated Value $1,819,743

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  20771 2nd Ave W, 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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  /73

  $3,500,000

  • 3 Beds
  • 3 Baths
  • 2,295 Sq Ft

  1083 Labat Ln, Cudjoe Key, FL 33042

  Experience elevated island living in this striking modern residence in Cudjoe Key, where sleek design meets the raw beauty of the Atlantic. This white contemporary home showcases a dramatic wall of glass along the oceanfront, creating a seamless connection between indoor living and the endless horizon beyond. The open-concept living space is flooded with natural light and anchored by breathtaking

  

  Sandra Tuttle

  Island Welcome Real Estate

  (786) 841-9203

  1083 Labat Ln, Cudjoe Key, FL 33042
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  $1,350,000 Sold Jul 24, 2025

  20883 4th Ave, Cudjoe Key, FL 33042

  • 3 Beds
  • 3 Baths
  • 2,524 Sq Ft
  • Built 2011

  Last Sold Summary

  • 21% Below List Price
  • $535/SF
  • 215 Days On Market

  Current Estimated Value $1,678,854

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  20883 4th Ave, Cudjoe Key, FL 33042
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  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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  $1,999,999 Under Contract

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

  23087 Sailfish Ln, Summerland Key, FL 33042

  Designed for those who live by the tides, this extraordinary waterfront residence captures everything that defines the Florida Keys lifestyle. Situated on a rare 15,625 sq ft double lot with 175 feet of deep-water dockage, the home enjoys a premier location one in from open water, delivering sweeping open water views while remaining protected within a wide 50-foot canal. Architecturally striking,

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (786) 807-9315

  23087 Sailfish Ln, Summerland Key, FL 33042
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  $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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  /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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  /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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  $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 $1,341,932

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  20735 5th Ave W, Summerland Key, FL 33042
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  /31

  Est $799,557 Not Listed For Sale

  22727 Jolly Roger Dr, Cudjoe Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,008 Sq Ft
  • Built 2001

  22727 Jolly Roger Dr, Cudjoe Key, FL 33042

  Last Sold Summary

  • $794/SF
  • 146 Days On Market

  Last Sold Price $800,000

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co
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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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  $450,000 Sold Aug 20, 2025

  701 Spanish Main Dr Unit 22, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 814 Sq Ft
  • Built 2016

  Last Sold Summary

  • 9% Below List Price
  • $553/SF
  • 283 Days On Market

  Last Listing Agent Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 22, Cudjoe Key, FL 33042
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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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  /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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  /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 $1,093,305

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

  128 Le Grand Ln, Summerland Key, FL 33042
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  /2

  Est $792,625 Not Listed For Sale

  53 Gold Boullion Rd, Cudjoe Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft
  • Built 2016

  53 Gold Boullion Rd, Cudjoe Key, FL 33042

  Last Sold Summary

  • 14% Below List Price
  • $495/SF

  Last Sold Price $695,000

  Last Listing Agent Mary Bryant Keller Williams Key West Compass Realty
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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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  /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 $779,721

  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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  Not Listed For Sale

  701 Spanish Main Dr Unit 554, Cudjoe Key, FL 33042

  • 1 Bed
  • 1 Bath
  • 420 Sq Ft
  • Built 1988

  701 Spanish Main Dr Unit 554, Cudjoe Key, FL 33042

  Last Sold Summary

  • $631/SF
  • 461 Days On Market

  Last Sold Price $265,000

  Last Listing Agent PATRICIA BRUMMER Waterfront Keys Realty Inc.
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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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  /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 $1,009,209

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

  366 Sawyer Dr, Summerland Key, FL 33042
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  Not Listed For Sale

  701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042

  • 2 Beds
  • Built 1978

  701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042

  Last Sold Summary

  • $408/SF
  • 78 Days On Market

  Last Sold Price $284,500

  Last Listing Agent PATRICIA BRUMMER Waterfront Keys Realty Inc.
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  /59

  $1,529,999 Open House 4/12

  • 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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  /41

  $650,000 Sold Jul 01, 2025

  22882 Buccaneer Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 1984

  Last Sold Summary

  • 19% Below List Price
  • $580/SF
  • 81 Days On Market

  Current Estimated Value $693,519

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

  22882 Buccaneer Ln, Summerland Key, FL 33042
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  /2

  Not Listed For Sale

  701 Spanish Main Dr Unit 559, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft
  • Built 2001

  701 Spanish Main Dr Unit 559, Cudjoe Key, FL 33042

  Last Sold Summary

  • $938/SF

  Last Sold Price $810,000

  Last Listing Agent PATRICIA BRUMMER Waterfront Keys Realty Inc.
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  /13

  $1,350,000

  • 3 Beds
  • 2 Baths
  • 1,488 Sq Ft

  22777 Jolly Roger Dr, Summerland Key, FL 33042

  Stop dreaming and start packing. This rare canal-front gem features a 2.75 assumable mortgage for qualified buyers—a game-changer in today’s market! Situated on a massive, double-fenced corner lot, this 3-bed, 2-bath home is the ultimate playground. There is enough room to park all your toys, boats, cars, and RV. Your 4-legged family members will love their own large yard. With no HOA, you even

  Olivia Poto GARRISON REALTY GROUP LLC

  22777 Jolly Roger Dr, Summerland Key, FL 33042
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  /52

  $2,300,000 Sold Sep 12, 2025

  23086 Snapper Ln, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,586 Sq Ft
  • Built 1985

  Last Sold Summary

  • 8% Below List Price
  • $889/SF
  • 147 Days On Market

  Current Estimated Value $2,226,471

  Last Listing Agent Greg MacLaren Internet Realty of the Florida Keys

  23086 Snapper Ln, Summerland Key, FL 33042
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  /2

  Not Listed For Sale

  701 Spanish Main Dr Unit 537, Cudjoe Key, FL 33042

  • 1 Bed
  • 1 Bath
  • 520 Sq Ft
  • Built 2000

  701 Spanish Main Dr Unit 537, Cudjoe Key, FL 33042

  Last Sold Summary

  • $712/SF

  Last Sold Price $370,000

  Last Listing Agent Lindsay Ryan EXP Realty LLC
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  /42

  $2,089,000

  • 5 Beds
  • 3 Baths
  • 1,978 Sq Ft

  94 Sacarma Dr, Cudjoe Key, FL 33042

  Rare Licensed Oceanfront Short-Term Vacation Rental in the Lower Florida Keys. Welcome to Fandango, a highly successful transient (daily-weekly) vacation rental home offering an exceptional investment opportunity and a personal retreat. This stunning 5-bedroom, 3-bathroom property, built in 2011 and expanded in 2018, was thoughtfully designed as the ultimate family vacation rental retreat.

  Michelle Blades Realty Executives Florida Keys Old Town

  94 Sacarma Dr, Cudjoe Key, FL 33042
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  /17

  $16,000 Sold Oct 28, 2025

  0 Budd Key Aly Unit 616603, Cudjoe Key, FL 33042

  • Land

  Last Sold Summary

  • 23% Below List Price
  • 12 Days On Market

  Last Listing Agent Bobby Coe RE/MAX Keys Connection (KW)

  0 Budd Key Aly Unit 616603, Cudjoe Key, FL 33042
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  /46

  Est $1,906,259 Not Listed For Sale

  271 W Indies Dr, Ramrod Key, FL 33042

  • 4 Beds
  • 4 Baths
  • 2,358 Sq Ft
  • Built 2023

  271 W Indies Dr, Ramrod Key, FL 33042

  Last Sold Summary

  • $806/SF
  • 342 Days On Market

  Last Sold Price $1,900,000

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co
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  $2,195,000

  • 5 Beds
  • 3 Baths
  • 1,903 Sq Ft

  125 Colson Dr, Summerland Key, FL 33042

  TRANSIENT LICENSE FOR NIGHTLY RENTALS BRINGING IN 250k-300K for 2026!! OPEN WATER VIEWS! ALMOST 2 ACRES TOTAL WITH 4 LOTS! THIS PROPERTY IS A ONE OF A KIND! A TRUE ''UNICORN!'' Turnkey Vacation Rental with 4 bedrooms and 2 baths in Main House which is a charming and OLD FLORIDA KEYS STYLE PROPERTY! Privacy, lush vegetation, stunning Open water views from the balconies from almost every room!

  Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

  125 Colson Dr, Summerland Key, FL 33042

Showing Results 81 - 120, Page 3 of 18