Summerland Key, FL Homes

• 

  

  

  /39

  $1,499,000

  • 3 Beds
  • 2 Baths
  • 1,944 Sq Ft

  20838 5th Ave W, Summerland Key, FL 33042

  Discover the ultimate boating lifestyle in the Florida Keys with this beautiful Deep Draft Canal Front Pool Home in the exclusive waterfront enclave of Cudjoe Gardens. Set on an expansive 11,000 sq ft lot with 100 feet of waterfront, this ground-level, above-flood concrete ranch home offers seamless access to the Pool and water. Inside, enjoy nearly 2,000 square feet of living space with 3

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (786) 952-7261

  20838 5th Ave W, Summerland Key, FL 33042
• 

  

  

  /61

  $1,750,000 Sold Mar 09, 2026

  876 Gulf Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,172 Sq Ft
  • Built 1978

  Last Sold Summary

  • 20% Below List Price
  • $1,493/SF
  • 122 Days On Market

  Current Estimated Value $1,614,886

  Last Listing Agent Lisa Swanson The Agency Florida Keys

  876 Gulf Dr, Summerland Key, FL 33042
• 

  

  /2

  Not Listed For Sale

  0 Vacant Unit 607262, Saddlebunch, FL 33040

  0 Vacant Unit 607262, Saddlebunch, FL 33040

  Last Sold Summary

  Last Sold Price $70,000

  Last Listing Agent Sarah Eckert Coldwell Banker Schmitt Real Estate Co. (KW)
• 

  

  

  /37

  $750,000

  • 3 Beds
  • 2 Baths
  • 1,316 Sq Ft

  29160 Primrose Ln, Big Pine Key, FL 33043

  Welcome to Eden Pines! This well maintained 3BR/2B home sits on a generous very private 10,000 sq ft lot in Big Pine Key.Featuring a garage and tons of storage inside and out, fenced yard & room for a pool!Inside you will find 3BR, 2 updated baths and a smart layout with an open concept living.Step outside to a beautiful covered porch the perfect spot to enjoy your morning coffee watching the key

  

  Michelle Howerton

  Brenda Donnelly Real Estate LLC

  (877) 521-8118

  29160 Primrose Ln, Big Pine Key, FL 33043
• 

  

  

  /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 $1,387,846

  Last Listing Agent Stacy Shahan Island Real Estate Company Florida Keys

  468 Sawyer Dr, Summerland Key, FL 33042
• 

  

  /14

  Est $514,755 Not Listed For Sale

  30919 Edward Rd Unit A, Big Pine Key, FL 33043

  • 3 Beds
  • Built 1943

  30919 Edward Rd Unit A, Big Pine Key, FL 33043

  Last Sold Summary

  • 129% Above List Price
  • $248/SF
  • 119 Days On Market

  Last Sold Price $225,000

  Last Listing Agent Shannon Butler Key Colony Beach Realty
• 

  

  /60

  $487,500

  • 2 Beds
  • 1 Bath
  • 667 Sq Ft

  701 Spanish Main Dr Unit 602, Cudjoe Key, FL 33042

  Oceanfront Paradise Awaits!Unit 602 in Venture OutExperience the epitome of Florida living in this charming Two-bedroom, one-bathroom mid-rise mobile home nestled within an exclusive gated community.This beautiful canal front home with ocean views from the backyard home boasts:* Prime Canal front Location: Enjoy breathtaking ocean views and direct access to the water from your private 35 ft

  

  Ian Calderwood

  Bluescape Real Estate

  (786) 981-9841

  701 Spanish Main Dr Unit 602, Cudjoe 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 $6,513,006

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  785 Sawyer Dr, Cudjoe Key, FL 33042
• 

  /2

  Est $468,984 Not Listed For Sale

  17172 Marlin Dr, Sugarloaf Shores, FL 33042

  • Studio

  17172 Marlin Dr, Sugarloaf Shores, FL 33042

  Last Sold Summary

  • 6% Below List Price

  Last Sold Price $500,000

  Last Listing Agent Donna Pezzi Keller Williams Key West Compass Realty
• 

  

  /66

  $799,000

  • 2 Beds
  • 2 Baths
  • 842 Sq Ft

  701 Spanish Main Dr Unit 172, Cudjoe Key, FL 33042

  Canal Front Oasis w/ Ocean Views & Resort Amenities | Income Producing Gem 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 high-rise home offers the ultimate Florida Keys lifestyle, combining tranquil canal-front living with breathtaking ocean views and an incredible array of world-class

  

  Ian Calderwood

  Bluescape Real Estate

  (786) 841-6970

  701 Spanish Main Dr Unit 172, Cudjoe Key, FL 33042
• 

  

  /26

  $390,000 Sold Jul 10, 2025

  27873 Coral Shores Rd, Little Torch Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 686 Sq Ft
  • Built 1985

  Last Sold Summary

  • 19% Below List Price
  • $569/SF
  • 70 Days On Market

  Last Listing Agent Tracy Shields KeyIsle Realty

  27873 Coral Shores Rd, Little Torch Key, FL 33042
• 

  /2

  Not Listed For Sale

  701 Spanish Main Dr Unit 137, Cudjoe Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 897 Sq Ft
  • Built 2000

  701 Spanish Main Dr Unit 137, Cudjoe Key, FL 33042

  Last Sold Summary

  • $736/SF

  Last Sold Price $660,000

  Last Listing Agent Kim Babenzien Expert Realty LLC (HQ)
• 

  

  /53

  $865,000 Under Contract

  • 2 Beds
  • 2 Baths
  • 1,092 Sq Ft

  1539 Lantana Ln, Big Pine Key, FL 33043

  Built like a fortress! This one-owner, CBS home was custom-built by Art Fuchs, one of the best. Most of the 195 ft. corner canal frontage provides an impressive concrete seawall with two step-down docks, davits and a fish-cleaning table. Dotted with coconut palms, slash pines, and a good-sized mango tree, this low-maintenance 7625 sq ft. property is bordered by a 45 ft. wide canal to the east and

  

  Patti Nickless

  Coldwell Banker Schmitt Lower Keys (KW)

  (877) 455-6393

  1539 Lantana Ln, Big Pine Key, FL 33043
• 

  

  /64

  $809,000 Sold Nov 12, 2025

  3714 Pine St, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 1989

  Last Sold Summary

  • 17% Below List Price
  • $722/SF
  • 194 Days On Market

  Current Estimated Value $809,683

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

  3714 Pine St, Big Pine Key, FL 33043
• 

  /2

  Est $183,993 Not Listed For Sale

  825 Hawksbill Ln, Sugarloaf Key, FL 33042

  • Studio

  825 Hawksbill Ln, Sugarloaf Key, FL 33042

  Last Sold Summary

  • 7% Below List Price

  Last Sold Price $172,000

  Last Listing Agent Paul Rogers Coldwell Banker Schmitt RE Co.
• 

  

  /65

  $3,999,000

  • 3 Beds
  • 3 Baths
  • 2,096 Sq Ft

  17015 Wahoo Ln W, Summerland Key, FL 33042

  Positioned on a rare west facing point lot with 270 ft of sparkling open water frontage on Sugarloaf Sound, this fully reimagined 3 Bedroom 3 Bathroom estate captures breathtaking sunset views across endless turquoise waters. Privately set on a gated 17,000 SF lot, the property lives like a private island compound framed by swaying palms, lush tropical landscaping, and the endless blue waters of

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  (833) 854-0770

  17015 Wahoo Ln W, Summerland Key, FL 33042
• 

  

  /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 $773,012

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  24833 Park Dr, Summerland Key, FL 33042
• 

  /2

  Est $3,059,776 Not Listed For Sale

  999 Flagship Dr, Summerland Key, FL 33042

  • 3 Beds
  • 4 Baths
  • 3,531 Sq Ft
  • Built 2024

  999 Flagship Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 2% Below List Price
  • $850/SF

  Last Sold Price $3,000,000

  Last Listing Agent Lee Sanders KeyIsle Realty
• 

  

  /26

  $1,225,000

  • 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. And with 120' of concrete seawall, there is plenty of room for a large boat, or boats. The home is a split-bedroom and bathroom floor plan with beautiful terrazzo floors, updated

  

  Christina Davis

  Coldwell Banker Schmitt RE Co.

  (786) 686-3066

  466 W Shore Dr, Summerland Key, FL 33042
• 

  

  /8

  $340,000 Sold Dec 11, 2025

  0 Overseas Hwy, Summerland Key, FL 33042

  • Land

  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
• 

  

  /34

  Not Listed For Sale

  701 Spanish Main Dr Unit 196, Cudjoe Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft
  • Built 1998

  701 Spanish Main Dr Unit 196, Cudjoe Key, FL 33042

  Last Sold Summary

  • $828/SF
  • 66 Days On Market

  Last Sold Price $715,000
• 

  

  /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
• 

  

  /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

  Current Estimated Value $1,545,429

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

  1370 Long Beach Dr, Big Pine Key, FL 33043
• 

  /2

  Est $1,208,477 Not Listed For Sale

  29565 Ranger Ave, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 2019

  29565 Ranger Ave, Big Pine Key, FL 33043

  Last Sold Summary

  • 3% Below List Price
  • $930/SF

  Last Sold Price $1,250,000

  Last Listing Agent Sandra Tuttle Island Welcome Real Estate
• 

  

  /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
• 

  

  /21

  $775,000 Sold Mar 23, 2026

  27360 Saint Croix Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1983

  Last Sold Summary

  • 16% Below List Price
  • $673/SF
  • 272 Days On Market

  Current Estimated Value $848,279

  Last Listing Agent Terry Bush Bluescape Real Estate

  27360 Saint Croix Ln, Summerland Key, FL 33042
• 

  

  /14

  Not Listed For Sale

  0 Lan Horvath Rd, Big Pine, FL 33043

  0 Lan Horvath Rd, Big Pine, FL 33043

  Last Sold Summary

  • 64 Days On Market

  Last Sold Price $90,000

  Last Listing Agent Yisel Montes The Keyes Company
• 

  

  /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
• 

  

  /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 $759,784

  Last Listing Agent Tommy Mack Coastal Collection Real Estate Inc.

  640 Carolyn Ave, Summerland Key, FL 33042
• 

  /2

  Est $1,024,636 Not Listed For Sale

  18954 Acosta Trail, Summerland Key, FL 33042

  • 1 Bed
  • 1 Bath
  • 1,008 Sq Ft
  • Built 2013

  18954 Acosta Trail, Summerland Key, FL 33042

  Last Sold Summary

  • 3% Below List Price
  • $991/SF

  Last Sold Price $999,000

  Last Listing Agent Lisa Swanson The Agency Florida Keys
• 

  

  /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
• 

  

  /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

  Current Estimated Value $1,690,104

  Last Listing Agent Krystal Thomas eXp Realty LLC

  22562 Jolly Roger Dr, Summerland Key, FL 33042
• 

  /2

  Est $456,014 Not Listed For Sale

  520 Blackbeard Rd, Little Torch Key, FL 33042

  • Studio

  520 Blackbeard Rd, Little Torch Key, FL 33042

  Last Sold Summary

  • 6% Below List Price

  Last Sold Price $485,000

  Last Listing Agent Banks Prevatt Coldwell Banker Schmitt RE Co.
• 

  

  /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
• 

  

  /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 $244,972

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

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

  /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

  Last Sold Summary

  Last Sold Price $30,000

  Last Listing Agent Allan Leder Preferred Properties (KW)
• 

  

  /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
• 

  

  /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
• 

  

  /4

  Not Listed For Sale

  0 Knockemdown Unit A11382026, Lower Keys, FL 33042

  0 Knockemdown Unit A11382026, Lower Keys, FL 33042

  Last Sold Summary

  • 198 Days On Market

  Last Sold Price $242,000

  Last Listing Agent Carmen David Xcellence Realty
• 

  

  /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

Showing Results 161 - 200, Page 5 of 18