Homes For Sale in Summerland Key, FL with a Swimming Pool

53 homes

Use arrow keys to navigate
$350,000
2 Beds
1 Bath
726 sqft
701 Spanish Main Dr #536,
Cudjoe Key, FL 33042
eXp Realty LLC KW Branch
Use arrow keys to navigate
NEW CONSTRUCTION
$599,000
2 Beds
2 Baths
840 sqft
701 Spanish Main Dr #29,
Cudjoe Key, FL 33042
Bluescape Real Estate
Use arrow keys to navigate
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.
Use arrow keys to navigate
$509,000
2 Beds
1.5 Baths
816 sqft
701 Spanish Main Dr #453,
Cudjoe Key, FL 33042
Bluescape Real Estate
Use arrow keys to navigate
$879,000
2 Beds
2 Baths
816 sqft
701 Spanish Main Dr #265,
Cudjoe Key, FL 33042
Expert Realty LLC (HQ)
Use arrow keys to navigate
$320,000
2 Beds
1 Bath
672 sqft
701 Spanish Main Dr #566,
Cudjoe Key, FL 33042
Bluescape Real Estate
Use arrow keys to navigate
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
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
3D VIEW
$535,000
2 Beds
2 Baths
860 sqft
701 Spanish Main Dr #247,
Cudjoe Key, FL 33042
Bluescape Real Estate
NEW CONSTRUCTION
$599,000
2 Beds
2 Baths
840 sqft
701 Spanish Main Dr #30,
Cudjoe Key, FL 33042
Bluescape Real Estate
NEW CONSTRUCTION
3D VIEW
3.34 ACRES
$4,595,000
5 Beds
5.5 Baths
4,103 sqft
231 E Shore Drive Unit 2,
Key West, FL 33040
Serhant
NEW CONSTRUCTION
3D VIEW
3.34 ACRES
$4,700,000
5 Beds
5.5 Baths
4,103 sqft
231 E Shore Drive Unit 6,
Key West, FL 33040
Serhant
$485,000
1 Bed
1 Bath
754 sqft
701 Spanish Main Dr #182,
Cudjoe Key, FL 33042
Bluescape Real Estate

Real Estate & Homes For Sale Near Summerland Key, FL

We found 30 more homes matching your filters just outside Summerland Key

Use arrow keys to navigate
NEW - 2 DAYS AGO
3D VIEW
$2,199,000
4 Beds
2.5 Baths
1,996 sqft
27385 Saint Lucie Ln,
Ramrod Key, FL 33042
William Raveis Florida LLC
Use arrow keys to navigate
NEW CONSTRUCTION
0.4 ACRES
$2,300,000
4 Beds
3 Baths
2,419 sqft
30995 Watson Blvd,
Big Pine Key, FL 33043
Coldwell Banker Schmitt Real Estate Co
Use arrow keys to navigate
3D VIEW
$999,000
2 Beds
2 Baths
1,116 sqft
27416 Cayman Ln,
Ramrod Key, FL 33042
Expert Realty LLC (HQ)
Use arrow keys to navigate
3D VIEW
$895,000
2 Beds
2 Baths
988 sqft
1669 Lantana Ln,
Big Pine Key, FL 33043
Coldwell Banker Schmitt RE Co.
Use arrow keys to navigate
3D VIEW
$1,399,000
3 Beds
2 Baths
2,006 sqft
27416 Tobago Ln,
Ramrod Key, FL 33042
KeyIsle Realty
Use arrow keys to navigate
3D VIEW
$1,649,000
3 Beds
3 Baths
1,589 sqft
6 Shore Dr,
Key West, FL 33040
RE/MAX Keys Connection (KW)
Use arrow keys to navigate
0.41 ACRES
$1,300,000
3 Beds
2 Baths
1,368 sqft
545 Ixora Dr,
Big Pine Key, FL 33043
Coldwell Banker Schmitt RE Co.
3D VIEW
$1,150,000
3 Beds
2 Baths
1,447 sqft
29466 Enterprise Ave,
Big Pine Key, FL 33043
Coldwell Banker Schmitt Lower Keys (KW)
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
$1,100,000
3 Beds
2 Baths
1,064 sqft
29038 Violet Dr,
Big Pine Key, FL 33043
Coldwell Banker Schmitt RE Co.
3D VIEW
0.47 ACRES
$1,164,000
3 Beds
3.5 Baths
1,508 sqft
1632 Bogie Dr,
Big Pine Key, FL 33043
Coldwell Banker Schmitt Lower Keys (KW)
NEW CONSTRUCTION
$1,469,000
3 Beds
3 Baths
1,500 sqft
27374 Guadaloupe Ln,
Ramrod Key, FL 33042
Meyer and Boumerhi Realty LLC
$1,199,000
3 Beds
2 Baths
1,330 sqft
1657 Watson Blvd,
Big Pine Key, FL 33043
Coldwell Banker Schmitt RE Co.
3D VIEW
0.25 ACRES
$1,400,000
3 Beds
2 Baths
1,540 sqft
1518 Sunrise Dr,
Big Pine Key, FL 33043
Coldwell Banker Schmitt RE Co.
FOR SALE BY OWNER
$779,000
3 Beds
2 Baths
1,665 sqft
27065 Dolphin Rd,
Ramrod Key, FL 33042
0.49 ACRES
$1,150,000
3 Beds
3 Baths
1,774 sqft
30525 Winifred St,
Big Pine Key, FL 33043
Expert Realty LLC (HQ)
NEW CONSTRUCTION
$1,480,000
4 Beds
3 Baths
2,120 sqft
27433 Antigua Ln,
Ramrod Key, FL 33042
Bluescape Real Estate
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
$1,149,900
2 Beds
2 Baths
1,312 sqft
3746 Park Ave,
Big Pine Key, FL 33043
Compass Florida - Miami Beach
3D VIEW
0.28 ACRES
$960,000
3 Beds
2 Baths
1,782 sqft
750 W Indies Dr,
Ramrod Key, FL 33042
Action Keys Realty of the Lower FL Keys LLC
NEW CONSTRUCTION
$819,000
3 Beds
3 Baths
1,500 sqft
27215 Mariposa Rd,
Ramrod Key, FL 33042
Meyer and Boumerhi Realty LLC
3D VIEW
$1,435,000
4 Beds
2 Baths
2,310 sqft
29562 Saratoga Ave,
Big Pine Key, FL 33043
Coldwell Banker Schmitt Lower Keys (KW)
3D VIEW
1.14 ACRES
$4,450,000
3 Beds
3 Baths
4,687 sqft
3742 Sea Grape St,
Big Pine Key, FL 33043
Ocean Sotheby's International
$899,000
3 Beds
2 Baths
1,418 sqft
1540 Lantana Ln,
Big Pine Key, FL 33043
Vylla Home
$1,595,000
3 Beds
2 Baths
2,229 sqft
643 Indies Rd,
Ramrod Key, FL 33042
Internet Realty of the Florida Keys
3D VIEW
0.81 ACRES
$2,150,000
3 Beds
3 Baths
2,486 sqft
30468 Oleander Blvd,
Big Pine Key, FL 33043
Coldwell Banker Schmitt Lower Keys (KW)
3D VIEW
0.32 ACRES
$1,850,000
2 Beds
2 Baths
1,980 sqft
1607 Sunrise Dr,
Big Pine Key, FL 33043
Coldwell Banker Schmitt Real Estate Co
3D VIEW
0.26 ACRES
$1,970,000
3 Beds
2 Baths
1,849 sqft
1733 Sunrise Dr,
Big Pine Key, FL 33043
Florida Realty of Miami Corp
3.5 ACRES
$12,999,999
31 Beds
19 Baths
21540-21470 Overseas Hwy,
Summerland Key, FL 33042
Select Properties of NWFL

1 More Home

We found 1 more home that matches your search in other listings.

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.

Homes For Sale in Summerland Key, FL with a Swimming Pool

53 homes

We found 30 more homes matching your filters just outside Summerland Key

Nearby Real Estate

Nearby Zip Codes

Popular Cities in Florida

Neighborhoods near Summerland Key

Summerland Key Property Types

Real Estate Guides

Find Rental Properties

Summerland Key Popular Features and Styles

Summerland Key Homes by Bedrooms and Bathrooms

Find Homes In Your Budget