Summerland Key, FL Homes

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  /50

  $1,599,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,645 Sq Ft

  56 Colson Dr, Summerland Key, FL 33042

  Exceptional waterfront living awaits at 56 Colson Drive in Cudjoe Gardens on Cudjoe Key--a fully renovated 3 Bedroom 2 Bathroom home offering 1,645 sq. ft. of thoughtfully planned interior space on a sprawling 11,900 sq. ft. lot. Built with CBS construction and impact doors and windows, this property combines durability with modern coastal appeal and is designed to take full advantage of the

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 841-7430

  56 Colson Dr, Summerland Key, FL 33042
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  /33

  $799,000 Sold Apr 28, 2025

  24833 Park Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,166 Sq Ft
  • Built 1956

  Last Sold Summary

  • 11% Below List Price
  • $685/SF
  • 115 Days On Market

  Current Estimated Value $786,992

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

  24833 Park Dr, Summerland Key, FL 33042
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  /2

  Est $536,965 Not Listed For Sale

  • Studio

  520 Blackbeard Rd, Little Torch Key, FL 33042

  520 Blackbeard Rd, Little Torch Key, FL 33042
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  /52

  $1,335,000

  • 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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  /8

  $340,000 Sold Dec 11, 2025

  0 Overseas Hwy, Summerland Key, FL 33042

  • Land
  • 0.29 Acre
  • $1,184,832 per Acre

  Last Sold Summary

  • 3% Below List Price
  • 328 Days On Market

  Last Listing Agent Stacy Shahan Island Real Estate Company Florida Keys

  0 Overseas Hwy, Summerland Key, FL 33042
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  /2

  Not Listed For Sale

  Lot 6 Mad Bob Rd Unit 1, Sugarloaf Key, FL 33042

  Lot 6 Mad Bob Rd Unit 1, Sugarloaf Key, FL 33042
• 

  

  /17

  $675,000

  • 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 Lower Keys (KW)

  (786) 957-7959

  17215 Keystone Rd, Sugarloaf Shores, FL 33042
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  /21

  $380,000 Sold Jun 24, 2025

  27848 Lobster Tail Trail, Little Torch Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 552 Sq Ft
  • Built 1971

  Last Sold Summary

  • 24% Below List Price
  • $688/SF
  • 248 Days On Market

  Last Listing Agent Derrick Johnson Coco Plum Real Estate

  27848 Lobster Tail Trail, Little Torch Key, FL 33042
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  /4

  Not Listed For Sale

  0 Knockemdown Unit A11382026, Lower Keys, FL 33042

  0 Knockemdown Unit A11382026, Lower Keys, FL 33042
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  /38

  $1,200,000 Under Contract

  • 3 Beds
  • 3 Baths
  • 2,016 Sq Ft

  218 Spanish Main Dr, Summerland Key, FL 33042

  Welcome to 218 Spanish Main Dr., a turnkey, recently renovated Florida Keys waterfront home offering the perfect blend of coastal charm and modern comfort. This 2-story, 3 bed, 3 bath fully fenced retreat boasts 2,016 sq ft of thoughtfully designed space with water views from nearly every room. Enjoy porches on both levels, ideal for morning coffee or sunset cocktails. The main level features an

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (305) 876-6037

  218 Spanish Main Dr, Summerland Key, FL 33042
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  /52

  $1,530,000 Sold Jan 16, 2026

  1370 Long Beach Dr, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,181 Sq Ft
  • Built 2011

  Last Sold Summary

  • 4% Below List Price
  • $1,296/SF
  • 33 Days On Market

  Last Listing Agent Coby Taylor Taylor & Assoc. RE, Inc.

  1370 Long Beach Dr, Big Pine Key, FL 33043
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  /2

  Est $894,725 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,144 Sq Ft

  27434 Saint Lucie Ln, Ramrod Key, FL 33042

  27434 Saint Lucie Ln, Ramrod Key, FL 33042
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  /47

  $569,900

  • 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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  /58

  $760,000 Sold Aug 19, 2025

  640 Carolyn Ave, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 848 Sq Ft
  • Built 2021

  Last Sold Summary

  • 2% Below List Price
  • $896/SF
  • 66 Days On Market

  Current Estimated Value $765,572

  Last Listing Agent Tommy Mack Coastal Collection Real Estate Inc.

  640 Carolyn Ave, Summerland Key, FL 33042
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  /2

  Est $2,272,103 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,360 Sq Ft

  305 S Point Dr, Summerland Key, FL 33042

  305 S Point Dr, Summerland Key, FL 33042
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  /79

  $615,000

  • 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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  /43

  $1,700,000 Sold Jan 30, 2026

  22562 Jolly Roger Dr, Summerland Key, FL 33042

  • 4 Beds
  • 2 Baths
  • 2,074 Sq Ft
  • Built 1987

  Last Sold Summary

  • 12% Below List Price
  • $820/SF
  • 140 Days On Market

  Last Listing Agent Krystal Thomas eXp Realty LLC

  22562 Jolly Roger Dr, Summerland Key, FL 33042
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  /2

  Est $1,434,557 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,986 Sq Ft

  22863 Bluegill Ln, Cudjoe Key, FL 33042

  22863 Bluegill Ln, Cudjoe Key, FL 33042
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  /30

  $750,000

  • 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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  /26

  $239,000 Sold Jun 30, 2025

  701 Spanish Main Dr Unit 6, Cudjoe Key, FL 33042

  • Land

  Last Sold Summary

  • 2% Below List Price
  • 74 Days On Market

  Current Estimated Value $245,086

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

  701 Spanish Main Dr Unit 6, Cudjoe Key, FL 33042
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  /3

  Est $498,667 Not Listed For Sale

  0 Disturbed Pine Rd Unit A11375753, Cudjoe Key, FL 33042

  0 Disturbed Pine Rd Unit A11375753, Cudjoe Key, FL 33042
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  /41

  $1,899,000 Open Sun 11AM - 1PM

  • 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 Lower Keys (KW)

  (786) 527-2862

  28573 Le Grand Rd, Little Torch Key, FL 33042
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  /57

  $2,800,000 Sold Oct 30, 2025

  22967 Redfish Ln, Cudjoe Key, FL 33042

  • 3 Beds
  • 4 Baths
  • 3,747 Sq Ft
  • Built 2019

  Last Sold Summary

  • 7% Below List Price
  • $747/SF
  • 37 Days On Market

  Current Estimated Value $2,811,102

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

  22967 Redfish Ln, Cudjoe Key, FL 33042
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  /2

  Est $277,000 Not Listed For Sale

  • Studio

  0 E Ave Unit 604969, Big Pine Key, FL 33043

  0 E Ave Unit 604969, Big Pine Key, FL 33043
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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 Lower Keys (KW)

  (305) 834-4054

  63 Sugarloaf Dr, Sugarloaf Shores, FL 33042
• 

  

  /25

  $310,000 Sold Mar 13, 2025

  28232 Dorothy Ave, Summerland Key, FL 33042

  • 2 Beds
  • 1.5 Baths
  • 1,064 Sq Ft
  • Built 1986

  Last Sold Summary

  • 9% Below List Price
  • $291/SF
  • 49 Days On Market

  Last Listing Agent Lanny Gardner Bluescape Real Estate

  28232 Dorothy Ave, Summerland Key, FL 33042
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  /2

  Est $502,153 Not Listed For Sale

  • Studio
  • 1 Bath

  27418 Jamaica Ln, Ramrod Key, FL 33042

  27418 Jamaica Ln, Ramrod Key, FL 33042
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  /86

  $5,999,000 Pending

  • 4 Beds
  • 4 Baths
  • 4,315 Sq Ft

  4500 Filer Cove Rd, Summerland Key, FL 33042

  Picture perfect Sunset Views over the open water at this 12-Acre waterfront compound located on Big Torch Key, a coastal community of large private estates located just 30 minutes outside of Key West. Driving down the gated 300' scenic driveway balmy breezes and tropical landscape lead you to the 4,315 sq. ft. open water residence. Once here you will enjoy world-class fishing and diving just

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 998-2623

  4500 Filer Cove Rd, Summerland Key, FL 33042
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  /44

  $700,000 Sold Jan 09, 2026

  701 Spanish Main Dr Unit 87, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft
  • Built 2000

  Last Sold Summary

  • 10% Below List Price
  • $810/SF
  • 23 Days On Market

  Last Listing Agent Holly Burger RE/MAX Keys Connection (KW)

  701 Spanish Main Dr Unit 87, Cudjoe Key, FL 33042
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  /2

  Not Listed For Sale

  13 Red Legs Ln, Cudjoe Key, FL 33042

  13 Red Legs Ln, Cudjoe Key, FL 33042
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  /74

  $799,000

  • 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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  /2

  $55,000 Sold Jun 02, 2025

  0 Canal Dr, Sugarloaf Key, FL 33042

  • Land

  Last Sold Summary

  • 11% Below List Price
  • 32 Days On Market

  Last Listing Agent Nate Meyer Meyer and Boumerhi Realty LLC

  0 Canal Dr, Sugarloaf Key, FL 33042
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  /2

  Not Listed For Sale

  12 Red Legs Ln, Cudjoe Key, FL 33042

  12 Red Legs Ln, Cudjoe Key, FL 33042
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  /45

  $1,599,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,788 Sq Ft

  17227 Allamanda Dr, Summerland Key, FL 33042

  Welcome to your own slice of paradise in the desirable Sugarloaf Shores neighborhood of the Lower Keys! This beautifully designed 3 bedroom, 2 bath home offers 1,788 sq. ft. of inviting living space that perfectly blends comfort, quality, and the laid-back island lifestyle. Located on the no-bridge side of Sugarloaf Shores, this property provides quick water access to world-class fishing, diving,

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (855) 803-0852

  17227 Allamanda Dr, Summerland Key, FL 33042
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  /43

  $990,000 Sold Dec 10, 2025

  29839 Newfound Blvd, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,750 Sq Ft
  • Built 1995

  Last Sold Summary

  • 1% Below List Price
  • $566/SF
  • 4 Days On Market

  Last Listing Agent Donna Halstead Coldwell Banker Schmitt RE Co.

  29839 Newfound Blvd, Big Pine Key, FL 33043
• 

  /2

  Not Listed For Sale

  0 Crane Blvd, Sugarloaf Key, FL 33042

  0 Crane Blvd, Sugarloaf Key, FL 33042
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  /38

  $718,000

  • 2 Beds
  • 1 Bath
  • 1,497 Sq Ft

  30416 Coconut Hwy, Big Pine Key, FL 33043

  This 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. A signature rock wall and paver drive enhance the property. Step inside the

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  (833) 608-1417

  30416 Coconut Hwy, Big Pine Key, FL 33043
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  /14

  $250,000 Sold Feb 24, 2025

  1639 Pine Channel Dr, Little Torch Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 6,725 Sq Ft
  • Built 1975

  Last Sold Summary

  • $37/SF
  • 7 Days On Market

  Last Listing Agent Rose Dell Keller Williams Key West Compass Realty

  1639 Pine Channel Dr, Little Torch Key, FL 33042
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  /2

  Est $650,181 Not Listed For Sale

  • Studio

  17162 Starfish Ln W, Sugarloaf Shores, FL 33042

  17162 Starfish Ln W, Sugarloaf Shores, FL 33042
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  /125

  $1,150,000

  • 2 Beds
  • 2 Baths
  • 1,284 Sq Ft

  22748 Blackbeard Ln, Cudjoe Key, FL 33042

  Welcome home to this impressively spacious 2-bedroom, 2-bath Keys retreat, offering an elevated blend of comfort, functionality, and coastal living. The outdoor living space is a dream with a new concrete pool & waterfall feature, 12k lb boat lift, 60' concrete seawall, & an expansive 10 foot deep back porch (total of nearly 700 sq ft of porches), all perfect for outdoor dining, lounging, &

  

  Lindsay Ryan

  EXP Realty LLC

  (786) 807-7897

  22748 Blackbeard Ln, Cudjoe Key, FL 33042

Showing Results 201 - 240, Page 6 of 18