Summerland Key, FL Homes

• 

  

  

  /26

  $1,250,000

  • 2 Beds
  • 2 Baths
  • 1,364 Sq Ft

  466 W Shore Dr, Summerland Key, FL 33042

  Welcome to 466 W Shore Dr in prestigious Summerland Key. This 2 bedroom concrete home is situated on a 12,000 sg foot lot, located on a wide deep water boating canal. There is an RV hookup, as well as power at the dock. The home is a split bedroom and bathroom floor plan with beautiful terrazzo floors, updated kitchen, and baths. Enjoy the [Noseeum] screened porch off the living area, or the tiki

  

  Christina Davis

  Coldwell Banker Schmitt RE Co.

  (786) 686-3066

  466 W Shore Dr, Summerland Key, FL 33042
• 

  

  /2

  $600,000 Sold Jul 14, 2025

  701 Spanish Main Dr Unit 573, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft
  • Built 1993

  Last Sold Summary

  • 14% Below List Price
  • $735/SF
  • 56 Days On Market

  Last Listing Agent Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 573, Cudjoe Key, FL 33042
• 

  

  

  /4

  Not Listed For Sale

  0 Knockemdown Unit A11382026, Lower Keys, FL 33042

  0 Knockemdown Unit A11382026, Lower Keys, FL 33042
• 

  

  

  /52

  $1,335,000

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

  28560 Doubloon Rd, Summerland Key, FL 33042

  This custom-built Jolly Roger Estates home designed by architect Glenn Gray offers indoor-outdoor living with multiple inviting porches and excellent, oceanside boat access. 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

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 772-6030

  28560 Doubloon Rd, Summerland Key, FL 33042
• 

  

  

  /37

  $642,000 Sold Jul 11, 2025

  31067 Avenue C, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,516 Sq Ft
  • Built 2005

  Last Sold Summary

  • 4% Above List Price
  • $423/SF
  • 9 Days On Market

  Current Estimated Value $650,830

  Last Listing Agent Jared Chiagouris Island Welcome Real Estate LLC

  31067 Avenue C, Big Pine Key, FL 33043
• 

  /2

  Est $895,198 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
• 

  

  /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
• 

  /2

  $49,000 Sold Oct 03, 2025

  Lot 24 Rainbow Beach, Big Torch Key, FL 33042

  • Land

  Last Sold Summary

  • 6% Below List Price
  • 50 Days On Market

  Last Listing Agent Pamela Stangler Expert Realty LLC

  Lot 24 Rainbow Beach, Big Torch Key, FL 33042
• 

  /2

  Est $2,258,064 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
• 

  

  /38

  $995,000

  • 3 Beds
  • 2 Baths
  • 2,080 Sq Ft

  687 & 689 Crane Blvd, Sugarloaf Key, FL 33042

  A truly special offering for those who value strength, design, and the uncommon. Built to endure, this elevated solid poured concrete home features an insulated and Gaco coated, concrete roof, concrete floors, and an open, vault-like design with soaring ceilings--bringing an airy, artsy, and industrial-chic feel to island living.Located in highly desirable Sugarloaf Key, just 20 minutes from Key

  

  Sandra Tuttle

  Island Welcome Real Estate

  (786) 807-6597

  687 & 689 Crane Blvd, Sugarloaf Key, FL 33042
• 

  

  /3

  $420,000 Sold Jun 27, 2025

  701 Spanish Main Dr Unit 175, Cudjoe Key, FL 33042

  • 1 Bed
  • 1 Bath
  • 488 Sq Ft
  • Built 1999

  Last Sold Summary

  • 13% Below List Price
  • $861/SF
  • 0 Days On Market

  Last Listing Agent Joyce Craul Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 175, Cudjoe Key, FL 33042
• 

  /2

  Est $1,399,548 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
• 

  

  /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
• 

  

  /38

  $840,000 Sold Sep 30, 2025

  3611 S Seas St, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,068 Sq Ft
  • Built 1990

  Last Sold Summary

  • 3% Below List Price
  • $787/SF
  • 183 Days On Market

  Last Listing Agent Scott Brisson KeyIsle Realty

  3611 S Seas St, Big Pine Key, FL 33043
• 

  

  /3

  Est $604,000 Not Listed For Sale

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

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

  

  /30

  $775,000

  • 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
• 

  

  /75

  $830,000 Sold Sep 15, 2025

  22738 Blackbeard Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1989

  Last Sold Summary

  • 17% Below List Price
  • $692/SF
  • 84 Days On Market

  Current Estimated Value $834,452

  Last Listing Agent Tommy Mack Coastal Collection Real Estate Inc.

  22738 Blackbeard Ln, Summerland Key, FL 33042
• 

  /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
• 

  

  /51

  $1,299,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,530 Sq Ft

  28532 Dirk Rd, Summerland Key, FL 33042

  Angler's paradise in Little Torch Key! This spacious, canal-front home boasts enviable access to world-class fishing and diving within minutes. With approximately 185' of waterfront on a clear, flow-through, deep-draft canal, this property is ideal for effortless and frequent boating adventures. Inside, an open-concept main living space lends itself to entertaining with a well-equipped Chef's

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (645) 205-0576

  28532 Dirk Rd, Summerland Key, FL 33042
• 

  

  /68

  $950,000 Sold Apr 11, 2025

  31670 Avenue C, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,227 Sq Ft
  • Built 1956

  Last Sold Summary

  • 4% Below List Price
  • $774/SF
  • 28 Days On Market

  Current Estimated Value $928,000

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

  31670 Avenue C, Big Pine Key, FL 33043
• 

  /2

  Est $498,769 Not Listed For Sale

  • Studio
  • 1 Bath

  27418 Jamaica Ln, Ramrod Key, FL 33042

  27418 Jamaica Ln, Ramrod Key, FL 33042
• 

  

  /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 Lower Keys (KW)

  (786) 527-2862

  28573 Le Grand Rd, Little Torch Key, FL 33042
• 

  

  /20

  $660,000 Sold Feb 07, 2025

  29132 Tulip Ln, Big Pine Key, FL 33043

  • 2 Beds
  • 3 Baths
  • 1,131 Sq Ft
  • Built 1990

  Last Sold Summary

  • 6% Below List Price
  • $584/SF
  • 111 Days On Market

  Current Estimated Value $675,999

  Last Listing Agent Haydee Stewart Bascom Grooms Real Estate (KW)

  29132 Tulip Ln, Big Pine Key, FL 33043
• 

  /2

  Not Listed For Sale

  13 Red Legs Ln, Cudjoe Key, FL 33042

  13 Red Legs Ln, Cudjoe Key, FL 33042
• 

  

  /45

  $949,000

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

  25057 7th St, Summerland Key, FL 33042

  Tropical Tranquility Meets Spacious Island Living.Welcome to your private retreat in the Lower Keys! Nestled on an expansive 20,000 sq ft lot, this meticulously maintained one-owner home offers the perfect blend of privacy, comfort, and Keys-style living. Backing up to a protected nature preserve, you'll enjoy uninterrupted sunset views from your master bedroom and upstairs balcony - with the

  

  Christopher Tanaka

  Coldwell Banker Schmitt RE Co.

  (786) 627-6100

  25057 7th St, Summerland Key, FL 33042
• 

  

  /41

  $1,105,000 Sold Sep 26, 2025

  22946 Bluegill Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1975

  Last Sold Summary

  • 14% Below List Price
  • $921/SF
  • 255 Days On Market

  Last Listing Agent Anneliese Dietrick Coldwell Banker Schmitt Lower Keys (KW)

  22946 Bluegill Ln, Summerland Key, FL 33042
• 

  /2

  Not Listed For Sale

  12 Red Legs Ln, Cudjoe Key, FL 33042

  12 Red Legs Ln, Cudjoe Key, FL 33042
• 

  

  /38

  $949,000 Under Contract

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

  1633 Lantana Ln, Big Pine Key, FL 33043

  Located in Big Pine Key, this 3-bedroom, 2-bathroom, canal front Pool Home is a perfect blend of comfort and coastal charm. Enter into the bright and airy Great Room filled with a plethora of natural light through lots of glass windows. The spacious Kitchen is a chef's delight offering stainless steel appliances, ample custom cabinetry, expansive granite countertops, and a central island with

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (866) 605-5015

  1633 Lantana Ln, Big Pine Key, FL 33043
• 

  

  /22

  $640,000 Sold Jan 27, 2025

  30876 Malaga Ln, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,080 Sq Ft
  • Built 1975

  Last Sold Summary

  • 5% Below List Price
  • $593/SF
  • 13 Days On Market

  Current Estimated Value $639,047

  Last Listing Agent Cliff Glansen FlatFee.com

  30876 Malaga Ln, Big Pine Key, FL 33043
• 

  /2

  Not Listed For Sale

  0 Crane Blvd, Sugarloaf Key, FL 33042

  0 Crane Blvd, Sugarloaf Key, FL 33042
• 

  

  /84

  $5,999,000

  • 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
• 

  

  /57

  $1,375,000 Sold Apr 17, 2025

  468 Sawyer Dr, Summerland Key, FL 33042

  • 4 Beds
  • 4 Baths
  • 1,797 Sq Ft
  • Built 1972

  Last Sold Summary

  • 19% Below List Price
  • $765/SF
  • 215 Days On Market

  Current Estimated Value $1,389,707

  Last Listing Agent Stacy Shahan Island Real Estate Company Florida Keys

  468 Sawyer Dr, Summerland Key, FL 33042
• 

  /2

  Est $687,731 Not Listed For Sale

  • Studio

  17162 Starfish Ln W, Sugarloaf Shores, FL 33042

  17162 Starfish Ln W, Sugarloaf Shores, FL 33042
• 

  

  /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
• 

  

  /28

  $632,000 Sold Jul 03, 2025

  28451 Gulf Blvd, Big Pine Key, FL 33043

  • 4 Beds
  • 2 Baths
  • 1,584 Sq Ft
  • Built 1985

  Last Sold Summary

  • 8% Below List Price
  • $399/SF
  • 93 Days On Market

  Current Estimated Value $641,188

  Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty

  28451 Gulf Blvd, Big Pine Key, FL 33043
• 

  /2

  Est $521,729 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,426 Sq Ft

  390 W Indies Dr, Ramrod Key, FL 33042

  390 W Indies Dr, Ramrod Key, FL 33042
• 

  

  /45

  $1,599,000

  • 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
• 

  

  /115

  $12,250,000 Sold May 07, 2025

  785 Sawyer Dr, Cudjoe Key, FL 33042

  • 7 Beds
  • 6 Baths
  • 4,888 Sq Ft
  • Built 2019

  Last Sold Summary

  • 5% Below List Price
  • $2,506/SF
  • 44 Days On Market

  Current Estimated Value $4,840,918

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

  785 Sawyer Dr, Cudjoe Key, FL 33042
• 

  /2

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 936 Sq Ft

  31255 Avenue G, Big Pine Key, FL 33043

  31255 Avenue G, Big Pine Key, FL 33043
• 

  

  /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

Showing Results 161 - 200, Page 5 of 18