Summerland Key, FL Homes

• 

  

  

  /29

  $395,000 Sold May 19, 2025

  701 Spanish Main Dr Unit 84, Cudjoe Key, FL 33042

  • Land

  Last Sold Summary

  • 5% Below List Price
  • 78 Days On Market

  Current Estimated Value $392,764

  Last Listing Agent Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 84, Cudjoe Key, FL 33042
• 

  

  /2

  Est $512,243 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
• 

  

  

  /55

  $1,500,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,467 Sq Ft

  21855 & 21865 Spain Blvd, Cudjoe Key, FL 33042

  Majestically positioned at the end of Spain Blvd, within the Prestigious Cudjoe Acres neighborhood. Discover 21855 & 21865 Spain Blvd. A Property that offers the kind of privacy that's almost impossible to find in the Florida Keys. Set on over 3 acres of land, this one-of-a-kind property is surrounded by naturally occurring native plants, mature trees, and freshwater ponds that encourage local

  

  Matthew Sheehan

  Ocean Sotheby's International Realty

  (866) 528-5667

  21855 & 21865 Spain Blvd, Cudjoe Key, FL 33042
• 

  

  /2

  $755,000 Sold Apr 24, 2025

  3786 Park Ave, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,176 Sq Ft
  • Built 1986

  Last Sold Summary

  • 6% Below List Price
  • $642/SF
  • 9 Days On Market

  Current Estimated Value $778,354

  Last Listing Agent Walter Ceballos, P.A. Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

  3786 Park Ave, Big Pine Key, FL 33043
• 

  

  /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
• 

  

  /61

  $2,150,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,674 Sq Ft

  743 Pattison Dr, Summerland Key, FL 33042

  Welcome to your slice of paradise in the Florida Keys! This stunning 3-bedroom, 2-bath canal-front home in desirable Cudjoe Gardens celebrates everything we love about island life -- in shades of blue. From the moment you arrive, you'll feel the calm, coastal vibe this home radiates.Beautifully remodeled in 2021 with full permits, this residence offers an open-concept living area with soaring

  

  Sandra Tuttle

  Island Welcome Real Estate

  (786) 756-9163

  743 Pattison Dr, Summerland Key, FL 33042
• 

  

  /47

  $1,282,000 Sold Nov 12, 2025

  29436 Independence Ave, Big Pine Key, FL 33043

  • 2 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • Built 1986

  Last Sold Summary

  • 6% Below List Price
  • $855/SF
  • 82 Days On Market

  Last Listing Agent Karen Haack Coldwell Banker Schmitt RE Co.

  29436 Independence Ave, Big Pine Key, FL 33043
• 

  /2

  Not Listed For Sale

  3 Big Pine Ave, Big Pine Key, FL 33043

  3 Big Pine Ave, Big Pine Key, FL 33043
• 

  

  /18

  $750,000

  • Land

  27941 Porgie Path, Summerland Key, FL 33042

  Located on Little Torch Key, this ROGO EXEMPT 6,221 sq. ft. lot boasts spectacular stunning sunset views over the gulf. Fantastic Gulf access from the back yard boat ramp allowing easy access to get out on the water, whether you're heading out for a day of fishing or a sunset kayak and paddle board tour. This Little Torch Key property offers stunning Gulf side sunset views and a prime location in

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 745-7897

  27941 Porgie Path, Summerland Key, FL 33042
• 

  /2

  $255,000 Sold Oct 20, 2025

  150 Coral Ave, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,100 Sq Ft
  • Built 1993

  Last Sold Summary

  • $232/SF
  • 0 Days On Market

  Current Estimated Value $457,000

  Last Listing Agent Kristen Brenner/Margie Casey T Florida Keys Real Estate Group

  150 Coral Ave, Summerland Key, FL 33042
• 

  /2

  Not Listed For Sale

  2 Big Pine Ave, Big Pine Key, FL 33043

  2 Big Pine Ave, Big Pine Key, FL 33043
• 

  

  /26

  $1,250,000 Open Sun 11AM - 1PM

  • 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
• 

  

  /3

  $325,000 Sold Oct 09, 2025

  29153 Tulip Ln, Big Pine Key, FL 33043

  • 2 Beds
  • 1 Bath
  • 912 Sq Ft
  • Built 1984

  Last Sold Summary

  • $356/SF
  • 0 Days On Market

  Current Estimated Value $405,386

  Last Listing Agent Ryan Gernaat Coldwell Banker Schmitt Lower Keys (KW)

  29153 Tulip Ln, Big Pine Key, FL 33043
• 

  /2

  Not Listed For Sale

  1 Big Pine Ave, Big Pine Key, FL 33043

  1 Big Pine Ave, Big Pine Key, FL 33043
• 

  

  /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
• 

  

  /51

  $420,000 Sold Nov 21, 2025

  701 Spanish Main Dr Unit 280, Cudjoe Key, FL 33042

  • 1 Bed
  • 1 Bath
  • 816 Sq Ft
  • Built 1979

  Last Sold Summary

  • 8% Below List Price
  • $515/SF
  • 185 Days On Market

  Last Listing Agent Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 280, Cudjoe Key, FL 33042
• 

  

  /9

  Not Listed For Sale

  22819 Blackbeard Ln, Cudjoe Key, FL 33042

  22819 Blackbeard Ln, Cudjoe Key, FL 33042
• 

  

  /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
• 

  

  /25

  $560,000 Sold Nov 21, 2025

  30342 Hibiscus Ln, Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,508 Sq Ft
  • Built 1969

  Last Sold Summary

  • 6% Below List Price
  • $371/SF
  • 230 Days On Market

  Last Listing Agent Joyce Craul Expert Realty LLC (HQ)

  30342 Hibiscus Ln, Big Pine Key, FL 33043
• 

  /2

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,170 Sq Ft

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

  30919 Edward Rd Unit A & B, Big Pine Key, FL 33043
• 

  

  /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
• 

  

  /4

  $50,000 Sold Dec 19, 2025

  0 Old State Rd Unit 616986, Cudjoe Key, FL 33042

  • Land

  Last Sold Summary

  • 41% Below List Price
  • 25 Days On Market

  Last Listing Agent Sabre Mendoza Coldwell Banker Schmitt RE Co.

  0 Old State Rd Unit 616986, Cudjoe Key, FL 33042
• 

  /2

  Est $219,242 Not Listed For Sale

  • Studio

  951 Hawksbill Ln, Sugarloaf Key, FL 33042

  951 Hawksbill Ln, Sugarloaf Key, FL 33042
• 

  

  /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
• 

  /2

  $50,000 Sold Nov 11, 2025

  Lot P No Name Key, No Name Key, FL 33043

  • Land
  • 0.5 Acre
  • $100,000 per Acre

  Last Sold Summary

  • 12% Below List Price
  • 55 Days On Market

  Last Listing Agent Pamela Stangler Expert Realty LLC

  Lot P No Name Key, No Name Key, FL 33043
• 

  

  /8

  Est $433,069 Not Listed For Sale

  53 Sugarloaf Dr, Sugarloaf Shores, FL 33042

  53 Sugarloaf Dr, Sugarloaf Shores, 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
• 

  

  /39

  $705,000 Sold Sep 08, 2025

  181 Doubloon Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,090 Sq Ft
  • Built 1985

  Last Sold Summary

  • 1% Above List Price
  • $647/SF
  • 7 Days On Market

  Current Estimated Value $710,204

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

  181 Doubloon Ln, Summerland Key, FL 33042
• 

  /2

  Not Listed For Sale

  430 Les Rohde Dr, Ramrod Key, FL 33042

  430 Les Rohde Dr, Ramrod Key, FL 33042
• 

  

  /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
• 

  

  /31

  $735,000 Sold Jun 06, 2025

  27373 Antigua Ln, Ramrod Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft
  • Built 2016

  Last Sold Summary

  • 2% Below List Price
  • $619/SF
  • 6 Days On Market

  Current Estimated Value $782,050

  Last Listing Agent Sandra Dolowy KeyIsle Realty

  27373 Antigua Ln, Ramrod Key, FL 33042
• 

  /2

  Est $544,100 Not Listed For Sale

  • Studio

  20874 4th Ave, Cudjoe Key, FL 33042

  20874 4th Ave, Cudjoe Key, FL 33042
• 

  

  /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
• 

  

  /5

  $235,000 Sold Sep 09, 2025

  1388 Avenue B, Big Pine Key, FL 33043

  • Land

  Last Sold Summary

  • 33% Below List Price
  • 212 Days On Market

  Current Estimated Value $434,929

  Last Listing Agent Sarah Dolson Keller Williams Key West Compass Realty

  1388 Avenue B, Big Pine Key, FL 33043
• 

  /2

  Not Listed For Sale

  0 Vacant Land Unit 603907, Sugarloaf Key, FL 33042

  0 Vacant Land Unit 603907, Sugarloaf Key, FL 33042
• 

  

  /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
• 

  

  /42

  $550,000 Sold Dec 01, 2025

  27213 Old State Road 4a Unit 4a, Summerland Key, FL 33042

  • 4 Beds
  • 2 Baths
  • 864 Sq Ft
  • Built 1984

  Last Sold Summary

  • 19% Below List Price
  • $637/SF
  • 125 Days On Market

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

  27213 Old State Road 4a Unit 4a, Summerland Key, FL 33042
• 

  /2

  Est $1,161,430 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,361 Sq Ft

  21034 Overseas Hwy, Cudjoe Key, FL 33042

  21034 Overseas Hwy, Cudjoe Key, FL 33042
• 

  

  /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
• 

  

  /28

  $500,000 Sold Jun 20, 2025

  30952 Baileys Ln, Big Pine Key, FL 33043

  • 2 Beds
  • 1 Bath
  • 575 Sq Ft
  • Built 1958

  Last Sold Summary

  • 13% Below List Price
  • $870/SF
  • 18 Days On Market

  Current Estimated Value $504,242

  Last Listing Agent Joyce Craul Expert Realty LLC (HQ)

  30952 Baileys Ln, Big Pine Key, FL 33043

Showing Results 241 - 280, Page 7 of 18