Summerland Key, FL Homes

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  /32

  $700,000 Sold May 14, 2025

  226 Newfound Blvd, Big Pine Key, FL 33043

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

  Last Sold Summary

  • 3% Below List Price
  • $729/SF
  • 17 Days On Market

  Current Estimated Value $710,893

  Last Listing Agent Madeleine Lowe Expert Realty LLC (HQ)

  226 Newfound Blvd, Big Pine Key, FL 33043
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  /8

  Est $193,746 Not Listed For Sale

  1135 Hakluyt Ln, Cudjoe Key, FL 33042

  1135 Hakluyt Ln, Cudjoe Key, FL 33042

  Last Sold Summary

  • 3% Below List Price
  • 7 Days On Market

  Last Sold Price $200,000

  Last Listing Agent John Nazzaro Keller Williams Realty Premier Properties - Kendall
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  /52

  $1,899,000 Under Contract

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

  1232 W Shore Dr, Big Pine Key, FL 33043

  Tucked away on an oversized open water lot in Eden Pines, this waterfront home offers a rare blend of sweeping water views, privacy, and the natural beauty that makes living in the Florida Keys so special. Set on a beautifully landscaped and fully fenced half-acre, this 3 bed, 2 bath residence provides a sense of space rarely found in the Keys. Enjoy morning coffee overlooking the water as the

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (844) 436-5125

  1232 W Shore Dr, Big Pine Key, FL 33043
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  /36

  $1,120,000 Sold Mar 24, 2026

  2148 Bahia Shores Rd, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1988

  Last Sold Summary

  • 5% Below List Price
  • $933/SF
  • 1 Day On Market

  Current Estimated Value $1,108,096

  Last Listing Agent Anne Press Lokation Real Estate

  2148 Bahia Shores Rd, Big Pine Key, FL 33043
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  /47

  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

  • $601/SF
  • 194 Days On Market

  Last Sold Price $312,500

  Last Listing Agent Anne Press Lokation Real Estate
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  /63

  $1,325,000

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

  28560 Doubloon Rd, Summerland Key, FL 33042

  Enjoy indoor-outdoor living with multiple inviting porches and excellent, oceanside boat access to the Atlantic and back-country. Features include a gated entry to covered parking, garage, fenced backyard, outdoor shower, tropical landscaping, 60 ft. canal-frontage, and a composite dock. Inside the ground-level foyer an oak staircase leads up to the main living area and continues to the

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 772-6030

  28560 Doubloon Rd, Summerland Key, FL 33042
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  /24

  $485,000 Sold May 23, 2025

  1923 Narcissus Ave, Big Pine Key, FL 33043

  • 2 Beds
  • 1.5 Baths
  • 1,506 Sq Ft
  • Built 1974

  Last Sold Summary

  • 22% Below List Price
  • $322/SF
  • 74 Days On Market

  Current Estimated Value $544,260

  Last Listing Agent Christopher Tanaka Coldwell Banker Schmitt RE Co.

  1923 Narcissus Ave, Big Pine Key, FL 33043
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  /20

  Est $260,167 Not Listed For Sale

  701 Spanish Main Dr Unit 14, Cudjoe Key, FL 33042

  • Built 2001

  701 Spanish Main Dr Unit 14, Cudjoe Key, FL 33042

  Last Sold Summary

  • 4% Above List Price
  • 167 Days On Market

  Last Sold Price $250,000

  Last Listing Agent Kelly Gardner Bluescape Real Estate
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  /17

  $599,900

  • Land

  17215 Keystone Rd, Sugarloaf Shores, FL 33042

  Cleared canal-front lot in Sugarloaf Shores with building permit in place and first inspection not due until December 2026! Positioned on the desirable no-bridge side, this expansive 27,716 sq. ft. residential parcel is surrounded by multi-million-dollar homes and offers easy access to the open water where days are enjoyed paddling and kayaking through mangrove-line creeks or heading out to

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (786) 957-7959

  17215 Keystone Rd, Sugarloaf Shores, FL 33042
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  /55

  $5,003,500 Sold Jan 05, 2026

  1151 Ocean Dr, Summerland Key, FL 33042

  • 5 Beds
  • 6 Baths
  • 3,952 Sq Ft
  • Built 2007

  Last Sold Summary

  • 28% Below List Price
  • $1,266/SF
  • 47 Days On Market

  Current Estimated Value $5,315,609

  Last Listing Agent Lisa Swanson The Agency Florida Keys

  1151 Ocean Dr, Summerland Key, FL 33042
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  /63

  Est $4,299,990 Not Listed For Sale

  17129 Amberjack Ln, Sugarloaf Shores, FL 33042

  • 6 Beds
  • 7 Baths
  • 4,200 Sq Ft
  • Built 2023

  17129 Amberjack Ln, Sugarloaf Shores, FL 33042

  Last Sold Summary

  • 14% Below List Price
  • $1,190/SF
  • 9 Days On Market

  Last Sold Price $5,000,000

  Last Listing Agent Jenna Stauffer Ocean Sotheby's International Realty
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  /27

  $630,000

  • 3 Beds
  • 2 Baths
  • 1,367 Sq Ft

  30350 Oleander Blvd, Big Pine Key, FL 33043

  Charming 3 Bedroom 2 Bathroom home in Big Pine Key, ready to welcome its next owners! Tucked away on a quiet street and surrounded by lush natural beauty, this property offers a peaceful and private setting. Inside, you will find a bright and spacious layout with abundant natural light flowing throughout the living areas. The kitchen is designed for both function and style, featuring a peninsula

  

  Ryan Gernaat

  Coldwell Banker Schmitt Lower Keys (KW)

  (877) 318-9145

  30350 Oleander Blvd, Big Pine Key, FL 33043
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  /34

  $600,000 Sold Sep 22, 2025

  19557 Mayan St, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 989 Sq Ft
  • Built 1958

  Last Sold Summary

  • 5% Below List Price
  • $607/SF
  • 186 Days On Market

  Current Estimated Value $608,949

  Last Listing Agent Lola McKee eXp Realty LLC

  19557 Mayan St, Summerland Key, FL 33042
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  /27

  Est $264,836 Not Listed For Sale

  701 Spanish Main Dr Unit 473, Cudjoe Key, FL 33042

  • 1 Bed
  • Built 1974

  701 Spanish Main Dr Unit 473, Cudjoe Key, FL 33042

  Last Sold Summary

  • 18% Above List Price
  • $311/SF
  • 161 Days On Market

  Last Sold Price $225,000

  Last Listing Agent Kelly Gardner Bluescape Real Estate
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  /47

  $559,000 Open Thu 10:30AM - 1:30PM

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  701 Spanish Main Dr Unit 510, Cudjoe Key, FL 33042

  Oceanfront Paradise Awaits!Unit 510 in Venture OutExperience the epitome of waterfront Florida living in this charming two-bedroom, two-bathroom mid-rise mobile home nestled within an exclusive gated community.This beautiful canal front home boasts:* Prime Canal front Location: Enjoy direct access to the water from your private 35 ft seawall.* Community Boat Ramp and boat washdown station.*

  

  Ian Calderwood

  Bluescape Real Estate

  (786) 686-7983

  701 Spanish Main Dr Unit 510, Cudjoe Key, FL 33042
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  /2

  $48,000 Sold Mar 13, 2026

  0 Bk 2 Lt 24 Windward Beach Estate Unit 615586, Little Torch Key, FL 33042

  • Land

  Last Sold Summary

  • 26% Below List Price
  • 250 Days On Market

  Current Estimated Value $1,146,000

  Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

  0 Bk 2 Lt 24 Windward Beach Estate Unit 615586, Little Torch Key, FL 33042
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  /16

  Not Listed For Sale

  8 Calico Jack Cir, Cudjoe Key, FL 33042

  8 Calico Jack Cir, Cudjoe Key, FL 33042

  Last Sold Summary

  • 212 Days On Market

  Last Sold Price $165,000

  Last Listing Agent Beata Sharpe Coldwell Banker Vanguard Realty
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  /71

  $607,000 Under Contract

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  1258 Division St, Big Pine Key, FL 33043

  Welcome to Your Own Slice of Island Paradise in Big Pine Key! Tucked away in the heart of Big Pine, this picture-perfect 3-bedroom, 1-bath home invites you to slow down, breathe deep, & truly enjoy island living. Set on an oversized double lot totaling 12,500 sq ft, this property is truly a private tropical sanctuary: lush, peaceful, and full of life.From the moment you step inside, soaring beam

  

  Lindsay Ryan

  EXP Realty LLC

  (833) 721-7372

  1258 Division St, Big Pine Key, FL 33043
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  /64

  $815,422 Sold Nov 06, 2025

  554 W Shore Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,407 Sq Ft
  • Built 1963

  Last Sold Summary

  • 9% Below List Price
  • $580/SF
  • 34 Days On Market

  Current Estimated Value $842,811

  Last Listing Agent Jimmy Lane Island Life Realty Experts

  554 W Shore Dr, Summerland Key, FL 33042
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  /2

  Not Listed For Sale

  7 Calico Jack Cir, Cudjoe Key, FL 33042

  7 Calico Jack Cir, Cudjoe Key, FL 33042

  Last Sold Summary

  Last Sold Price $200,000

  Last Listing Agent Beata Sharpe Coldwell Banker Vanguard Realty
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  /30

  $750,000 Under Contract

  • 4 Beds
  • 2 Baths
  • 1,456 Sq Ft

  26868 Mariposa Rd, Ramrod Key, FL 33042

  Presenting a newly built 2023 home on a spacious 12,250 sq. ft. lot in Ramrod Shores, designed with both efficiency and style in mind. This four-bedroom, two-bathroom property features durable construction elements like a metal roof and impact-resistant windows, optimizing insurance costs, with all 3 insurances combined under $5,000 total. The interior boasts an open-concept floor plan with high

  

  Dan Serban

  Key West Luxury Real Estate Inc (KW)

  (786) 783-4956

  26868 Mariposa Rd, Ramrod Key, FL 33042
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  /75

  $950,000 Sold Apr 30, 2025

  529 W Shore Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft
  • Built 1991

  Last Sold Summary

  • 21% Below List Price
  • $990/SF
  • 75 Days On Market

  Current Estimated Value $927,627

  Last Listing Agent Everett Smith Ocean Sotheby's International Realty

  529 W Shore Dr, Summerland Key, FL 33042
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  /32

  Est $454,519 Not Listed For Sale

  701 Spanish Main Dr Unit 609, Cudjoe Key, FL 33042

  • 1 Bed
  • Built 1988

  701 Spanish Main Dr Unit 609, Cudjoe Key, FL 33042

  Last Sold Summary

  • 1% Above List Price
  • $1,103/SF
  • 256 Days On Market

  Last Sold Price $450,000

  Last Listing Agent Paul Rogers Coldwell Banker Schmitt RE Co.
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  /41

  $1,899,000

  • 3 Beds
  • 3 Baths
  • 1,998 Sq Ft

  28573 Le Grand Rd, Little Torch Key, FL 33042

  This 2,000 sq ft concrete fortress was designed and built by the current owner and sprawls over 3 waterfront lots boasting 325' of canal frontage. Enjoy fantastic fishing and diving just minutes away from the the 180' deep draft concrete dock complete with boat basin, private boat ramp and davits. Upon entering this 3 Bedroom, 3 Bath home, you are greeted with an oversized Great Room which opens

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (786) 527-2862

  28573 Le Grand Rd, Little Torch Key, FL 33042
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  /71

  $3,150,000 Sold Aug 28, 2025

  225 Colson Dr, Summerland Key, FL 33042

  • 6 Beds
  • 7 Baths
  • 4,976 Sq Ft
  • Built 2010

  Last Sold Summary

  • 10% Below List Price
  • $633/SF
  • 118 Days On Market

  Current Estimated Value $3,260,698

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  225 Colson Dr, Summerland Key, FL 33042
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  /30

  Not Listed For Sale

  701 Spanish Main Dr Unit 392, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft
  • Built 1999

  701 Spanish Main Dr Unit 392, Cudjoe Key, FL 33042

  Last Sold Summary

  • $751/SF
  • 176 Days On Market

  Last Sold Price $649,000

  Last Listing Agent Kelly Gardner Bluescape Real Estate
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  /49

  $698,800

  • 3 Beds
  • 2 Baths
  • 1,039 Sq Ft

  29048 Iris Dr, Big Pine Key, FL 33043

  50' wide canal provides great boat access to the Atlantic and back country via Pine Channel for excellent fishing and diving in the stunning waters of the Lower Keys. If you're looking for a move-in ready stilt home at an entry-level price, this is it! Many updates have been made in recent years including impact-resistant windows and doors, new stainless steel kitchen appliances, water heater,

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  (833) 974-5892

  29048 Iris Dr, Big Pine Key, FL 33043
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  /32

  $1,830,000 Sold Apr 02, 2025

  17023 Allamanda Dr W, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,104 Sq Ft
  • Built 1979

  Last Sold Summary

  • 8% Below List Price
  • $1,658/SF
  • 77 Days On Market

  Current Estimated Value $1,830,442

  Last Listing Agent Lisa Swanson The Agency Florida Keys

  17023 Allamanda Dr W, Summerland Key, FL 33042
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  /33

  Est $862,291 Not Listed For Sale

  28120 County Rd, Little Torch Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,350 Sq Ft
  • Built 2024

  28120 County Rd, Little Torch Key, FL 33042

  Last Sold Summary

  • 1% Above List Price
  • $630/SF
  • 74 Days On Market

  Last Sold Price $849,900

  Last Listing Agent Natallie Liz Expert Realty LLC (HQ)
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  /10

  $499,000

  • Land

  63 Sugarloaf Dr, Sugarloaf Shores, FL 33042

  Welcome to the lowest priced waterfront lot with an active building permit on prestigious Sugarloaf Key. This oversized 14,706 sq. ft. canal-front property features no-bridge ocean access, granting you instant entry to world-class fishing, diving, and boating. Located in the premier residential enclave of the Sugarloaf Shores, this lot includes an active building permit for a custom 2,120 sq.

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (305) 834-4054

  63 Sugarloaf Dr, Sugarloaf Shores, FL 33042
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  /43

  $1,150,000 Sold Sep 22, 2025

  1032 Caribbean Dr E, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,380 Sq Ft
  • Built 1990

  Last Sold Summary

  • 18% Below List Price
  • $833/SF
  • 175 Days On Market

  Current Estimated Value $1,149,220

  Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

  1032 Caribbean Dr E, Summerland Key, FL 33042
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  /2

  Est $1,111,956 Not Listed For Sale

  17277 Dolphin St E, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft
  • Built 1995

  17277 Dolphin St E, Summerland Key, FL 33042

  Last Sold Summary

  • 3% Below List Price
  • $766/SF

  Last Sold Price $1,076,000

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co
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  /74

  $799,000 Pending

  • 2 Beds
  • 2 Baths
  • 766 Sq Ft

  701 Spanish Main Dr Unit 333,334, Cudjoe Key, FL 33042

  Canal Front Oasis with Resort Amenities!Nightly Rentals Allowed!Income Producing Gem!RARE-DOUBLE LOT!! Allows 2 cars with 2 separate driveways. Massive 69' Seawall!RARE-DAVITS for your boat!! Escape to your own slice of paradise in the highly sought-after, gated resort community of Venture Out on Cudjoe Key! This stunning 2-bedroom, 2-bathroom mid-rise home offers the ultimate Florida Keys

  

  Ian Calderwood

  Bluescape Real Estate

  (844) 482-8589

  701 Spanish Main Dr Unit 333,334, Cudjoe Key, FL 33042
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  /37

  $705,000 Sold Aug 21, 2025

  27312 Anguila Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,148 Sq Ft
  • Built 1989

  Last Sold Summary

  • 15% Below List Price
  • $614/SF
  • 127 Days On Market

  Current Estimated Value $736,843

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  27312 Anguila Ln, Summerland Key, FL 33042
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  /14

  Est $238,014 Not Listed For Sale

  701 Spanish Main Dr Unit 646, Cudjoe Key, FL 33042

  • 2 Beds
  • Built 2000

  701 Spanish Main Dr Unit 646, Cudjoe Key, FL 33042

  Last Sold Summary

  • 6% Above List Price
  • $402/SF
  • 246 Days On Market

  Last Sold Price $225,000

  Last Listing Agent Mary Conklin Action Keys Realty of the Lower FL Keys LLC
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  /38

  $678,000

  • 2 Beds
  • 2 Baths
  • 1,497 Sq Ft

  30416 Coconut Hwy, Big Pine Key, FL 33043

  Looking for a lot of land in the Keys, and a well-maintained home? This rare 25,000 sq. ft. property has plenty of room to add a pool and/or tiki hut, park an RV, boat trailers, so much more! Over 1/2 acre, the 4 lots are bordered by Coconut Hwy. to the north, Avenue B to the west, and Hibiscus Ln. to the south from which vehicles can access the large, fenced portion of the back yard. Step inside

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  (833) 608-1417

  30416 Coconut Hwy, Big Pine Key, FL 33043
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  /39

  $912,250 Sold Apr 03, 2025

  22879 Blackbeard Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 2002

  Last Sold Summary

  • 8% Below List Price
  • $679/SF
  • 43 Days On Market

  Current Estimated Value $928,883

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate

  22879 Blackbeard Ln, Summerland Key, FL 33042
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  /2

  Est $985,335 Not Listed For Sale

  421 W Indies, Ramrod Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,124 Sq Ft
  • Built 1996

  421 W Indies, Ramrod Key, FL 33042

  Last Sold Summary

  • 16% Below List Price
  • $1,042/SF

  Last Sold Price $1,171,500

  Last Listing Agent Michele Adams Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys
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  /27

  $1,055,000

  • 3 Beds
  • 3 Baths
  • 1,344 Sq Ft

  29051 Magnolia Ln, Big Pine Key, FL 33043

  Experience Florida Keys waterfront living in the heart of Big Pine Key. This canal-front home with a full concrete seawall and direct boating access offers an exceptional opportunity to enjoy the relaxed Lower Florida Keys lifestyle surrounded by world-class fishing, diving, and boating. The elevated main home features a 2 bedroom, 2 bathroom layout with an open living area, spacious kitchen with

  

  Yvette Toledo-Baste

  COMPASS FLORIDA LLC

  (855) 408-6871

  29051 Magnolia Ln, Big Pine Key, FL 33043
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  /31

  $725,000 Sold Jan 05, 2026

  27235 Mariposa Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,364 Sq Ft
  • Built 2017

  Last Sold Summary

  • 4% Below List Price
  • $532/SF
  • 127 Days On Market

  Current Estimated Value $746,134

  Last Listing Agent Brent Bishop Internet Realty of the Florida Keys

  27235 Mariposa Rd, Summerland Key, FL 33042

Showing Results 81 - 120, Page 3 of 18