Movoto Real Estate

Homes Recently Sold in Upper Sugarloaf Key, FL

430 Homes
 
23057 Bluegill Ln, Cudjoe Key, FL 33042
  • $1,350,000
  • 3Bd
  • 2Ba
  • 1,270 Sq Ft
SOLD 10/30/26
116 Spanish Main Dr, Cudjoe Key, FL 33042
  • $1,224,000
  • 2Bd
  • 2Ba
  • 1,100 Sq Ft
SOLD 10/30/26
701 Spanish Main Dr #LOT 62, Cudjoe Key, FL 33042
  • $205,000
  • 2Bd
  • 1Ba
  • 756 Sq Ft
SOLD 10/27/26
20920 5th Ave, Cudjoe Key, FL 33042
  • $2,550,000
  • 4Bd
  • 3Ba
  • 2,913 Sq Ft
SOLD 10/26/26
939 Hawksbill Ln, Sugarloaf Key, FL 33042
  • $900,000
  • 3Bd
  • 2Ba
  • 1,868 Sq Ft
SOLD 10/23/26
22960 Sharp Ln, Cudjoe Key, FL 33042
  • $515,000
  • 2Bd
  • 1Ba
  • 975 Sq Ft
SOLD 10/19/26
111 Doubloon Ln, Cudjoe Key, FL 33042
  • $800,000
  • 2Bd
  • 2Ba
  • 864 Sq Ft
SOLD 10/19/26
701 Spanish Main Dr #417, Cudjoe Key, FL 33042
  • $455,000
  • 2Bd
  • 2Ba
  • 758 Sq Ft
SOLD 10/19/26
22832 John Silver Ln, Cudjoe Key, FL 33042
  • $849,000
  • 3Bd
  • 3Ba
  • 1,800 Sq Ft
SOLD 10/16/26
17183 W Green Turtle Ln, Sugarloaf Key, FL 33042
  • $1,050,000
  • 3Bd
  • 2Ba
  • 984 Sq Ft
SOLD 10/15/26
22542 Jolly Roger Dr, Cudjoe Key, FL 33042
  • $2,000,000
  • 4Bd
  • 3Ba
  • 2,440 Sq Ft
SOLD 10/13/26
21012 6th Ave, Cudjoe Key, FL 33042
  • $1,300,000
  • 2Bd
  • 2Ba
  • 1,372 Sq Ft
SOLD 10/08/26
22953 John Silver Ln, Cudjoe Key, FL 33042
  • $900,000
  • 3Bd
  • 2Ba
  • 960 Sq Ft
SOLD 10/06/26
22961 John Avery Ln, Cudjoe Key, FL 33042
  • $850,000
  • 2Bd
  • 2Ba
  • 960 Sq Ft
SOLD 10/05/26
24347 W Caribbean Dr, Summerland Key, FL 33042
  • $1,149,000
  • 3Bd
  • 2Ba
  • 1,232 Sq Ft
SOLD 10/05/26
701 Spanish Main Dr #LOT 610, Cudjoe Key, FL 33042
  • $195,000
  • 0.05 Acre
SOLD 10/01/26
701 Spanish Main Dr #LOT 49, Cudjoe Key, FL 33042
  • $775,000
  • 2Bd
  • 1Ba
  • 806 Sq Ft
SOLD 09/22/26
22542 Jolly Roger Dr, Summerland Key, FL 33042
  • $2,000,000
  • 4Bd
  • 3Ba
  • 2,440 Sq Ft
SOLD 09/22/26
701 Spanish Main Dr #LOT 411, Cudjoe Key, FL 33042
  • $475,000
  • 2Bd
  • 2Ba
  • 318 Sq Ft
SOLD 09/17/26
17210 Angelfish Ln, Sugarloaf Key, FL 33042
  • $2,250,000
  • 3Bd
  • 3Ba
  • 2,288 Sq Ft
SOLD 09/11/26
885 Hawksbill Ln, Sugarloaf Key, FL 33042
  • $1,225,000
  • 3Bd
  • 2Ba
  • 1,398 Sq Ft
SOLD 09/08/26
701 Spanish Main Dr #47, Cudjoe Key, FL 33042
  • $775,000
  • 2Bd
  • 2Ba
  • 816 Sq Ft
SOLD 09/04/26
22872 Buccaneer Ln, Cudjoe Key, FL 33042
  • $1,449,000
  • 3Bd
  • 3Ba
  • 1,500 Sq Ft
SOLD 09/01/26
17151 Marlin Dr, Sugarloaf Key, FL 33042
  • $1,090,000
  • 3Bd
  • 2Ba
  • 1,522 Sq Ft
SOLD 09/01/26
22811 Buccaneer Ln, Cudjoe Key, FL 33042
  • $920,000
  • 3Bd
  • 2Ba
  • 1,200 Sq Ft
SOLD 08/31/26
701 Spanish Main Dr #653, Cudjoe Key, FL 33042
  • $250,000
  • 1Bd
  • 1Ba
  • 340 Sq Ft
SOLD 08/31/26
16843 E Point Dr, Sugarloaf Key, FL 33042
  • $2,400,000
  • 3Bd
  • 2Ba
  • 2,224 Sq Ft
SOLD 08/28/26
180 Sugarloaf Dr, Sugarloaf Key, FL 33042
  • $675,000
  • 3Bd
  • 2Ba
  • 1,232 Sq Ft
SOLD 08/28/26
22748 Blackbeard Ln, Cudjoe Key, FL 33042
  • $955,000
  • 2Bd
  • 2Ba
  • 1,280 Sq Ft
SOLD 08/18/26
17385 Keystone Rd, Sugarloaf Key, FL 33042
  • $2,450,000
  • 4Bd
  • 4Ba
  • 1,804 Sq Ft
SOLD 08/17/26
1129 Hawksbill Ln, Sugarloaf Key, FL 33042
  • $950,000
  • 2Bd
  • 2Ba
  • 1,150 Sq Ft
SOLD 08/13/26
19594 Caloosa St #LOT 29, Sugarloaf Key, FL 33042
  • $70,000
  • 0.11 Acre
SOLD 08/12/26
288 Spanish Main Dr, Cudjoe Key, FL 33042
  • $860,000
  • 3Bd
  • 2Ba
  • 1,144 Sq Ft
SOLD 08/11/26
22410 Jolly Roger Dr, Cudjoe Key, FL 33042
  • $1,500,000
  • 2Bd
  • 2Ba
  • 1,587 Sq Ft
SOLD 08/10/26
16805 Tamarind Rd, Sugarloaf Key, FL 33042
  • $2,650,000
  • 4Bd
  • 3Ba
  • 2,812 Sq Ft
SOLD 08/10/26
165 Cutlass Ln, Cudjoe Key, FL 33042
  • $1,000,000
  • 4Bd
  • 3Ba
  • 2,448 Sq Ft
SOLD 08/06/26
lot15 Bk2 Bad George Rd, Sugarloaf Key, FL 33042
  • $150,000
  • 1.02 Acre
SOLD 08/03/26
701 Spanish Main Dr #97, Cudjoe Key, FL 33042
  • $700,000
  • 2Bd
  • 2Ba
  • 640 Sq Ft
SOLD 08/03/26
701 Spanish Main Dr #172, Cudjoe Key, FL 33042
  • $775,000
  • 2Bd
  • 2Ba
  • 842 Sq Ft
SOLD 08/03/26
24225 W Caribbean Dr, Summerland Key, FL 33042
  • $985,000
  • 3Bd
  • 2Ba
  • 1,056 Sq Ft
SOLD 07/31/26
17326 Jamaica Ln, Sugarloaf Key, FL 33042
  • $750,000
  • 2Bd
  • 2Ba
  • 1,520 Sq Ft
SOLD 07/31/26
56 Bay Dr, Key West, FL 33040
  • $1,150,000
  • 3Bd
  • 2Ba
  • 1,372 Sq Ft
SOLD 07/29/26
17 Palm Dr, Key West, FL 33040
  • $360,000
  • 2Bd
  • 1Ba
  • 812 Sq Ft
SOLD 07/24/26
16640 Cypress Rd, Sugarloaf Key, FL 33042
  • $1,595,000
  • 3Bd
  • 2Ba
  • 1,764 Sq Ft
SOLD 07/24/26
lot13 John Silver Ln, Cudjoe Key, FL 33042
  • $160,000
  • 0.14 Acre
SOLD 07/23/26
142 Peg Leg Ln, Cudjoe Key, FL 33042
  • $1,400,000
  • 4Bd
  • 3Ba
  • 2,136 Sq Ft
SOLD 07/23/26
17249 E Bonefish Ln, Sugarloaf Key, FL 33042
  • $3,150,000
  • 5Bd
  • 4Ba
  • 3,060 Sq Ft
SOLD 07/21/26
17042 W Starfish Ln, Sugarloaf Key, FL 33042
  • $3,299,000
  • 6Bd
  • 5Ba
  • 3,700 Sq Ft
SOLD 07/17/26
1330 Sugarloaf Blvd, Sugarloaf Key, FL 33042
  • $2,000,000
  • 3Bd
  • 2Ba
  • 1,624 Sq Ft
SOLD 07/14/26
701 Spanish Main Dr #51, Cudjoe Key, FL 33042
  • $837,000
  • 2Bd
  • 2Ba
  • 888 Sq Ft
SOLD 07/10/26
1 - 50 of 430 Homes in Upper Sugarloaf Key, FL
1 2 3 4 5 ... 9
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

Schools
Ratings provided by great school

Frequently Asked Questions about Real Estate in Upper Sugarloaf 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.