Movoto Real Estate

Summerland Key Real Estate & Summerland Key, FL Homes For Sale | Page 4

207 Homes
 
111 Doubloon Ln, Cudjoe Key, FL 33042
  • $850,000
  • 2Bd
  • 2Ba
  • 864 Sq Ft
22542 Jolly Roger, Summerland Key, FL 33042
  • $1,725,000
  • 4Bd
  • 4Ba
  • 2,440 Sq Ft
27937 Coral Shores Rd, Little Torch Key, FL 33042
  • $759,000
  • 3Bd
  • 2Ba
  • 985 Sq Ft
335 Pirates Rd, Little Torch Key, FL 33042
  • $1,099,999
  • 3Bd
  • 2Ba
  • 1,320 Sq Ft
22832 John Silver Ln, Cudjoe Key, FL 33042
  • $849,000
  • 3Bd
  • 3Ba
  • 1,800 Sq Ft
3256 Catherine St, Big Torch Key, FL 33042
  • $1,899,000
  • 2Bd
  • 2Ba
  • 1,800 Sq Ft
23057 Bluegill Ln, Cudjoe Key, FL 33042
  • $1,349,000
  • 3Bd
  • 2Ba
  • 1,270 Sq Ft
3635 Trade Winds St, Big Pine Key, FL 33043
  • $840,000
  • 2Bd
  • 2Ba
  • 1,048 Sq Ft
29172 Rose Dr, Big Pine Key, FL 33043
  • $695,000
  • 2Bd
  • 2Ba
  • 1,056 Sq Ft
22822 Buccaneer Ln, Cudjoe Key, FL 33042
  • $799,000
  • 2Bd
  • 2Ba
  • 1,082 Sq Ft
27348 Dominica Ln, Ramrod Key, FL 33042
  • $2,200,000
  • 3Bd
  • 2Ba
  • 1,512 Sq Ft
29663 Saratoga Ave, Big Pine Key, FL 33043
  • $1,295,000
  • 3Bd
  • 2Ba
  • 1,508 Sq Ft
257 La Fitte Rd, Little Torch Key, FL 33042
  • $1,250,000
  • 2Bd
  • 2Ba
  • 927 Sq Ft
21012 6th Ave, Cudjoe Key, FL 33042
  • $1,399,000
  • 2Bd
  • 2Ba
  • 1,372 Sq Ft
22939 Gasparilla Ln, Cudjoe Key, FL 33042
  • $1,399,000
  • 3Bd
  • 2Ba
  • 1,434 Sq Ft
22961 John Avery Ln, Cudjoe Key, FL 33042
  • $895,900
  • 2Bd
  • 2Ba
  • 960 Sq Ft
22953 John Silver Ln, Cudjoe Key, FL 33042
  • $949,000
  • 3Bd
  • 2Ba
  • 960 Sq Ft
21640 Overseas Hwy, Cudjoe Key, FL 33042
  • $2,800,000
  • 4Bd
  • 3Ba
  • 3,286 Sq Ft
22542 Jolly Roger Dr, Cudjoe Key, FL 33042
  • $1,725,000
  • 4Bd
  • 3Ba
  • 2,440 Sq Ft
22552 Jolly Roger Dr, Cudjoe Key, FL 33042
  • $499,000
  • 0.16 Acre
28177 Julia Ave, Little Torch Key, FL 33042
  • $240,000
  • 2Bd
  • 1Ba
  • 672 Sq Ft
22920 Privateer Dr, Cudjoe Key, FL 33042
  • $590,000
  • 3Bd
  • 2Ba
  • 1,560 Sq Ft
216 Newfound Blvd, Big Pine Key, FL 33043
  • $800,000
  • 3Bd
  • 2Ba
  • 1,360 Sq Ft
29549 Forrestal Ave, Big Pine Key, FL 33043
  • $1,800,000
  • 3Bd
  • 2Ba
  • 1,800 Sq Ft
701 Spanish Main Dr #417, Cudjoe Key, FL 33042
  • $493,000
  • 2Bd
  • 2Ba
  • 758 Sq Ft
20920 5th Ave, Cudjoe Key, FL 33042
  • $2,795,000
  • 4Bd
  • 3Ba
  • 2,913 Sq Ft
701 Spanish Main Dr #140, Cudjoe Key, FL 33042
  • $399,900
  • 2Bd
  • 1Ba
  • 833 Sq Ft
231 E Shore Dr UNIT 4, Key West, FL 33040
  • $4,375,000
  • 5Bd
  • 6Ba
  • 4,103 Sq Ft
420 W Indies Dr, Ramrod Key, FL 33042
  • $875,000
  • 3Bd
  • 2Ba
  • 1,036 Sq Ft
$24K
24840 Park Dr, Summerland Key, FL 33042
  • $950,000
  • 3Bd
  • 2Ba
  • 1,565 Sq Ft
$25K
29678 Enterprise Ave, Big Pine Key, FL 33043
  • $1,295,000
  • 4Bd
  • 2Ba
  • 1,820 Sq Ft
28560 Doubloon Rd, Little Torch Key, FL 33042
  • $1,299,999
  • 3Bd
  • 2Ba
  • 1,820 Sq Ft
$25K
701 Spanish Main Dr #432, Cudjoe Key, FL 33042
  • $460,000
  • 0.04 Acre
$20K
701 Spanish Main Dr #247, Cudjoe Key, FL 33042
  • $535,000
  • 2Bd
  • 2Ba
  • 860 Sq Ft
$14K
27433 Antigua Ln, Ramrod Key, FL 33042
  • $1,480,000
  • 4Bd
  • 3Ba
  • 2,120 Sq Ft
$10K
29188 Tulip Ln, Big Pine Key, FL 33043
  • $600,000
  • 2Bd
  • 2Ba
  • 1,050 Sq Ft
$45K
lot21 Aloha Dr, Little Torch Key, FL 33042
  • $64,750
701 Spanish Main Dr #154, Cudjoe Key, FL 33042
  • $525,000
  • 2Bd
  • 2Ba
  • 836 Sq Ft
$14K
701 Spanish Main Dr #30, Cudjoe Key, FL 33042
  • $649,000
  • 2Bd
  • 2Ba
  • 840 Sq Ft
$50K
860 Lagoon Dr, Summerland Key, FL 33042
  • $1,950,000
  • 3Bd
  • 3Ba
  • 1,797 Sq Ft
231 E Shore Dr #6, Summerland Key, FL 33042
  • $4,400,000
  • 5Bd
  • 6Ba
  • 3,119 Sq Ft
$25K
lot8 Little Knockemdown Ky #AKA PARCEL 23, Summerland Key, FL 33042
  • $85,000
  • 4 Acre
27935 Tarpon Ter, Little Torch Key, FL 33042
  • $305,000
  • 0.09 Acre
$15K
701 Spanish Main Dr #543, Cudjoe Key, FL 33042
  • $329,000
  • 2Bd
  • 2Ba
  • 748 Sq Ft
$10K
1147 Basque Ln, Cudjoe Key, FL 33042
  • $450,000
  • 0.16 Acre
$25K
29859 Overseas Hwy #A-3, Big Pine Key, FL 33043
  • $145,000
$10K
701 Spanish Main Dr #182, Cudjoe Key, FL 33042
  • $485,000
  • 1Bd
  • 1Ba
  • 754 Sq Ft
$10K
701 Spanish Main Dr #69, Cudjoe Key, FL 33042
  • $259,000
  • 0.05 Acre
$6K
21540 21470 Overseas Hwy, Cudjoe Key, FL 33042
  • $12,999,999
  • 31Bd
  • 19Ba
$495K
3127 Stewart Rd, Middle Torch Key, FL 33042
  • $1,800,000
  • 3Bd
  • 2Ba
  • 1,841 Sq Ft
$100K
151 - 200 of 207 Homes for sale in Summerland Key, FL
1 2 3 4 5
By entering my info and clicking Submit below, I am providing my e-signature and express written consent to receive marketing emails, calls, and texts (including via automatic telephone dialing systems, AI generative, artificial or pre-recorded voice technology) relating to my inquiry from Movoto (and parties calling/messaging on their behalf) even if my number appears on the company, state, or national Do Not Call Registry. You also agree to ourTerms and Conditions and Privacy Policy. Consent not required to receive services (call 1-844-420-1270 to be connected without providing consent).

Explore nearby locations

The prices shown are the median list prices.

Narrow your search

Summerland Key, FL real estate market trends

Statistics as of October 2026
$1.77M
Avg. list price
$1,062/Sqft
Avg. price/sqft
29
Homes for sale
1,797 Sqft
Avg. home size
129 Days
Avg. days on market
Movoto makes it easy to track market trends in Summerland Key, FL. Whether you’re entering the market or planning your next move, understanding these key metrics can guide smart decisions. Looking for more detailed housing market stats in Summerland Key, FL?
Schools
Summerland Key, FL Schools. Ratings provided by great school See all…

Frequently Asked Questions about Summerland Key, FL

Meet with a real estate agent today (844) 417-0593
  • Movoto Logo
  • Download IOS APP Download Android APP
The multiple listing information is provided by Miami Association of REALTORS®. IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Buyer to verify all information. The information provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing information updated every 15 minutes. Terms of use & Privacy Policy, California Privacy Info. Copyright © 2005 - 2026 Movoto, Inc. All rights reserved. Equal Housing Opportunity CalDRE CalDRE #01517281
Movoto Real Estate is committed to ensuring accessibility for individuals with disabilities. We are continuously working to improve the accessibility of our web experience for everyone. We welcome feedback and accommodation requests, please submit them here.
The multiple listing information is provided by Miami Association of REALTORS® from a copyrighted compilation of listings. The compilation of listings and each individual are ©2026 Miami Association of REALTORS®. All Rights Reserved. The information provided is for consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All properties are subject to prior sale or withdrawal. All information provided is deemed reliable but is not guaranteed accurate, and should be independently verified.
All listings featuring the BMLS logo are provided by BeachesMLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed. Copyright ©2026 BeachesMLS, Inc. IDX information is provided exclusively for consumers’ personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by MLS.
The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange program of the Florida Keys Board of REALTORS®. IDX information is provided exclusively for consumers’ personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the MLS.
Requests for information regarding mortgage products will be directed to Movoto.com affiliate, Lower, LLC - a licensed Mortgage Lender (NMLS #1124061), or, based on your location, may be redirected to a participating mortgage marketing partner that may pay Lower, LLC for any consumer contact information provided through this site.