Sugarloaf Key, FL Real Estate & Homes For Sale

40 homes

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NEW - 2 MIN AGO
3D VIEW
0.29 ACRES
$2,549,000
4 Beds
3 Baths
2,594 sqft
265 S Point Dr,
Sugarloaf Key, FL 33042
Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key
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NEW - 1 DAY AGO
NEW CONSTRUCTION
3D VIEW
0.29 ACRES
$6,400,000
5 Beds
5 Baths
3,700 sqft
17162 Starfish Ln W,
Sugarloaf Key, FL 33042
The Agency Florida Keys
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NEW - 2 DAYS AGO
3D VIEW
0.29 ACRES
$995,000
3 Beds
2 Baths
1,300 sqft
17155 Hibiscus Ln,
Sugarloaf Key, FL 33042
Berkshire Hathaway HomeServices Knight & Gardner Realty
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0.39 ACRES
$3,999,999
4 Beds
3 Baths
2,096 sqft
17015 Wahoo Ln W,
Summerland Key, FL 33042
Coldwell Banker Schmitt Real Estate Co
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3D VIEW
2.88 ACRES
$949,000
2 Beds
2 Baths
2,280 sqft
17050 Old State Rd #4A,
Summerland Key, FL 33042
Island Welcome Real Estate LLC
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$399,000
2 Beds
1 Bath
460 sqft
6 Beach Dr,
Key West, FL 33040
Coldwell Banker Schmitt Lower Keys (KW)
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NEW CONSTRUCTION
3D VIEW
$1,100,000
3 Beds
2 Baths
1,404 sqft
49 Blue Water Dr,
Saddlebunch Key, FL 33040
RE/MAX Keys Connection (KW)
0.63 ACRES
$1,650,000
3 Beds
2 Baths
2,605 sqft
1481 Sugarloaf Blvd,
Sugarloaf Key, FL 33042
Ocean Sotheby's International Realty
$1,100,000
2950 Overseas Hwy #53,
Key West, FL 33040
Keller Williams Key West Compass Realty
$1,100,000
2950 Overseas Hwy #52,
Key West, FL 33040
Keller Williams Key West Compass Realty
OPEN SAT, 12-2PM
3D VIEW
$1,649,000
3 Beds
3 Baths
1,589 sqft
6 Shore Dr,
Key West, FL 33040
RE/MAX Keys Connection (KW)
$739,000
3 Beds
2 Baths
1,296 sqft
19590 Tequesta St,
Sugarloaf Key, FL 33042
Coldwell Banker Schmitt Real Estate Co
NEW CONSTRUCTION
3D VIEW
$1,199,000
3 Beds
2 Baths
1,404 sqft
99 Palm Dr,
Key West, FL 33040
LPT Realty, LLC
$972,000
3 Beds
1 Bath
1,400 sqft
12 Bay Dr,
Key West, FL 33040
Island Welcome Real Estate LLC
$1,129,000
2 Beds
2 Baths
932 sqft
24 Beach Dr,
Key West, FL 33040
Key West Luxury Real Estate Inc (KW)
$999,999
3 Beds
2 Baths
1,296 sqft
17 E Circle Dr #A,
Key West, FL 33040
Coastal Collection Real Estate Inc.
0.34 ACRES
$699,000
3 Beds
2 Baths
1,302 sqft
19421 Canal Dr,
Sugarloaf Key, FL 33042
Century 21 Circle- Islamorada
$1,100,000
2950 Overseas Hwy #57,
Key West, FL 33040
Keller Williams Key West Compass Realty
0.3 ACRES
$1,595,000
3 Beds
3 Baths
3,000 sqft
182 Venetian Way,
Sugarloaf Key, FL 33042
LoKation Real Estate
$749,900
3 Beds
2 Baths
1,296 sqft
19543 Navajo St,
Sugarloaf Key, FL 33042
Expert Realty LLC
3D VIEW
$1,200,000
2 Beds
2 Baths
1,344 sqft
17286 Jamaica Ln,
Sugarloaf Key, FL 33042
Coldwell Banker Schmitt Real Estate Co
3D VIEW
0.36 ACRES
$3,750,000
4 Beds
3.5 Baths
2,409 sqft
17387 Dolphin Street E,
Sugarloaf, FL 33042
Coldwell Banker Schmitt Real E
$799,000
2950 Overseas Hwy #2,
Key West, FL 33040
Keller Williams Key West Compass Realty
3D VIEW
$450,000
2 Beds
2 Baths
873 sqft
4 Coral Dr,
Key West, FL 33040
RE/MAX Keys Connection (KW)
0.5 ACRES
$799,000
3 Beds
2 Baths
984 sqft
937 Loggerhead Ln,
Sugarloaf Key, FL 33042
Buy The Keys
$599,000
2950 Overseas Hwy #33,
Key West, FL 33040
Keller Williams Key West Compass Realty
3D VIEW
0.49 ACRES
$998,000
3 Beds
2 Baths
1,225 sqft
83 Sugarloaf Dr,
Sugarloaf Key, FL 33042
Coldwell Banker Schmitt Real Estate Co. (KW)
1.01 ACRES
$899,000
3 Beds
2 Baths
1,968 sqft
19267 Hansen Trl,
Sugarloaf Key, FL 33042
Expert Realty LLC (HQ)
3D VIEW
0.27 ACRES
$3,199,000
4 Beds
3.5 Baths
2,044 sqft
17183 Coral Dr,
Sugarloaf Key, FL 33042
Coldwell Banker Schmitt RE Co.
0.34 ACRES
$85,000
19617 Date Palm Dr,
Sugarloaf Key, FL 33042
Coldwell Banker Schmitt Real Estate Co. (KW)
$1,175,000
2950 Overseas Hwy #64,
Key West, FL 33040
Keller Williams Key West Compass Realty
$1,175,000
2950 Overseas Hwy #63,
Key West, FL 33040
Keller Williams Key West Compass Realty
0.77 ACRES
$5,200,000
4 Beds
3.5 Baths
2,660 sqft
17013 Coral Dr,
Sugarloaf Key, FL 33042
Coldwell Banker Schmitt Real Estate Co
0.29 ACRES
$2,375,000
5 Beds
4 Baths
2,772 sqft
205 S Point Dr,
Sugarloaf Key, FL 33042
LPT Realty, LLC
0.34 ACRES
$499,000
63 Sugarloaf Dr,
Sugarloaf Key, FL 33042
Coldwell Banker Schmitt Real Estate Co
3D VIEW
5.33 ACRES
$19,750,000
6 Beds
6.5 Baths
4,402 sqft
15760 Old State Road 4A,
Sugarloaf, FL 33042
The Agency Florida Keys
3D VIEW
2.33 ACRES
$8,995,000
6 Beds
4.5 Baths
5,208 sqft
16750 Old State Rd,
Sugarloaf Key, FL 33042
The Agency Florida Keys
$599,000
2 Beds
2 Baths
1,010 sqft
4 Shore Dr,
Key West, FL 33040
Coldwell Banker Schmitt Islamorada
0.35 ACRES
$644,500
132 Sugarloaf Dr,
Sugarloaf Key, FL 33042
Coastal Collection Real Estate Inc.
10.5 ACRES
$1,500,000
169 Overseas Hwy,
Key West, FL 33040
Coldwell Banker Schmitt Real Estate Co.
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Real Estate & Homes For Sale Near Sugarloaf Key, FL

We found 29 more homes matching your filters just outside Sugarloaf Key

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$439,000
2 Beds
2 Baths
864 sqft
55 Boca Chica Rd #447,
Key West, FL 33040
Coldwell Banker Schmitt Real Estate Co
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NEW CONSTRUCTION
3D VIEW
0.5 ACRES
$1,645,000
3 Beds
2 Baths
1,696 sqft
165 Colson Dr,
Cudjoe Key, FL 33042
Island Welcome Real Estate
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0.29 ACRES
$3,200,000
5 Beds
4 Baths
2,839 sqft
20731 2nd Ave W,
Summerland Key, FL 33042
Coldwell Banker Schmitt Real Estate Co
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0.25 ACRES
$2,299,995
3 Beds
2 Baths
2,020 sqft
459 Pattison Dr,
Cudjoe Key, FL 33042
Coldwell Banker Schmitt Real Estate Co
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$315,000
2 Beds
1 Bath
885 sqft
55 Boca Chica Rd #85,
Key West, FL 33040
Island Group Realty (KW)
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0.27 ACRES
$2,499,999
6 Beds
5 Baths
3,568 sqft
6 Egret Ln,
Key West, FL 33040
Century 21 Circle - Key West
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$289,000
2 Beds
2 Baths
816 sqft
55 Boca Chica Rd #89,
Key West, FL 33040
Bascom Grooms Real Estate (KW)
FOR SALE BY OWNER
$2,000,000
4 Beds
2 Baths
2,048 sqft
20843 2nd Ave W,
Cudjoe Key, FL 33042
0.31 ACRES
$1,575,000
3 Tiburon Cir,
Key West, FL 33040
Internet Realty of the Florida Keys
3D VIEW
0.37 ACRES
$1,399,000
3 Beds
2 Baths
1,356 sqft
51 Drost Dr,
Cudjoe Key, FL 33042
Coldwell Banker Schmitt Real Estate Co
NEW CONSTRUCTION
$2,060,000
5 Beds
3 Baths
1,978 sqft
94 Sacarma Dr,
Cudjoe Key, FL 33042
Realty Executives Florida Keys Old Town
NEW CONSTRUCTION
0.33 ACRES
$6,200,000
5 Beds
4.5 Baths
4,624 sqft
36 Cannon Royal Dr,
Shark Key, FL 33040
Brenda Donnelly Real Estate LLC
1.57 ACRES
$2,195,000
5 Beds
3 Baths
1,903 sqft
125 Colson Dr,
Cudjoe Key, FL 33042
American Caribbean Real Estate, Christie's International Real Estate
$275,000
Disturbed Pine Rd,
Summerland Key, FL 33042
Expert Realty LLC
3D VIEW
0.27 ACRES
$2,699,999
4 Beds
2.5 Baths
2,452 sqft
20833 4th Ave W,
Cudjoe Key, FL 33042
Coldwell Banker Schmitt Real Estate Co
1.2 ACRES
$5,650,000
13 Beds
7 Baths
5,022 sqft
21470 Overseas Hwy,
Cudjoe Key, FL 33042
Select Properties of NWFL
$1,270,000
3 Beds
2 Baths
1,320 sqft
174 Tortuga Ln,
Cudjoe Key, FL 33042
eXp Realty LLC
3D VIEW
0.39 ACRES
$2,499,000
4 Beds
2 Baths
2,739 sqft
21023 2nd Ave,
Cudjoe Key, FL 33042
Coldwell Banker Schmitt Real Estate Co
NEW CONSTRUCTION
3D VIEW
0.43 ACRES
$12,500,000
6 Beds
6.5 Baths
5,930 sqft
31 Sea Lore Ln,
Key West, FL 33040
Ocean Sotheby's International Realty
3D VIEW
0.29 ACRES
$3,099,000
4 Beds
3 Baths
3,056 sqft
21090 5th Ave,
Cudjoe Key, FL 33042
Coldwell Banker Schmitt Real Estate Co
$30,000
Bk #15-lt 6,
Summerland Key, FL 33042
American Caribbean Real Estate, Christie's International Real Estate
OPEN SAT, 10-12PM
3D VIEW
$1,150,000
2 Beds
2 Baths
1,344 sqft
20868 5th Ave W,
Cudjoe Key, FL 33042
Coldwell Banker Schmitt RE Co.
3D VIEW
$1,299,000
3 Beds
2 Baths
1,741 sqft
21025 3rd Ave,
Cudjoe Key, FL 33042
Coldwell Banker Schmitt Real Estate Co
3D VIEW
$1,799,000
3 Beds
2.5 Baths
2,456 sqft
51 Sawyer Dr,
Cudjoe Key, FL 33042
Coldwell Banker Schmitt Real Estate Co
$532,000
2 Beds
2 Baths
1,064 sqft
55 Boca Chica Rd #27,
Key West, FL 33040
Expert Realty LLC (HQ)
$239,000
1 Bed
1 Bath
420 sqft
55 Boca Chica Rd #57,
Key West, FL 33040
Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key
$485,000
2 Beds
1 Bath
800 sqft
55 Boca Chica Rd #132,
Key West, FL 33040
Keller Williams Key West Compass Realty
30.75 ACRES
$100,000
14-67 26 Saddlebunch Ky,
Key West, FL 33040
Ocean Sotheby's International Realty
4 ACRES
$85,000
8 Little Knockemdown Ky,
Summerland Key, FL 33042
Coldwell Banker Schmitt RE Co.

What Locals Say about Sugarloaf Key

Nate M.
11y ago
"I'm a Realtor in Sugarloaf and have lived here since 1995. I've raised 2 children here, and the schools are absolutely fantastic! Sugarloaf is the perfect place to live - offering outstanding boating, fishing, diving, etc., miles of walking paths, surrounded by ocean and nature, yet just a quick hop to the fun and excitement of Key West."
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Machina1
14y ago
"It used to be safe until last week when the new neighbors moved in, they are renters, I know that we all have to make money, but , it seems like the old tried and prooved method of "salting" the neighborhood applies here, Paradise Lost !!, well i'll be moving, soon!!"
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Leigh A.
15y ago
"Quiet, safe neighborhood. Location, Location, Location. Perfect lower keys community."
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All listings featuring the BMLS logo are provided by Beaches MLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed. Copyright 2026 Beaches Multiple Listing Service, Inc. Information is provided exclusively 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.

MLS Internet Data Exchange (IDX) information is provided exclusively 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, and that the data is deemed reliable but is not guaranteed accurate by the Florida Keys MLS.

Sugarloaf Key, FL Real Estate & Homes For Sale

40 homes

We found 29 more homes matching your filters just outside Sugarloaf Key

What Locals Say about Sugarloaf Key

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Sugarloaf Key, FL Real Estate & Homes For Sale

40 homes

Home prices got you spooked?

We found 29 more homes matching your filters just outside Sugarloaf Key

What Locals Say about Sugarloaf Key

Browse Sugarloaf Key, FL homes by type