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Cudjoe Key, FL - homes for sale
101 of 101 results displayed
- New
$2,100,000Active4 beds 3 baths2,440 sq. ft.22542 Jolly Roger Dr, Lower Keys, FL 33042
MLS# A11977423Listed by: COLDWELL BANKER SCHMITT R.E. - New
$324,999Active2 beds 2 baths980 sq. ft.230 Yardarm Road, Cudjoe, FL 33042
MLS# 618882Listed by: KELLER WILLIAMS KEY WEST COMPASS REALTY - New
$495,000Active0.05 Acres701 Spanish Main Drive #84, Cudjoe, FL 33042
MLS# 618910Listed by: MIAMI NEW REALTY - New
$469,000Active1 beds 2 baths735 sq. ft.701 Spanish Main Drive #548, Cudjoe, FL 33042
MLS# 618837Listed by: BLUESCAPE REAL ESTATE - New
$529,000Active2 beds 2 baths758 sq. ft.701 Spanish Main Drive #417, Cudjoe, FL 33042
MLS# 618828Listed by: BLUESCAPE REAL ESTATE 
$300,000Active2.31 Acres21865 Spain Boulevard, Cudjoe, FL 33042
MLS# 618821Listed by: COLDWELL BANKER SCHMITT LOWER KEYS (KW)
$1,200,000Active3 beds 2 baths1,467 sq. ft.21855 Spain Boulevard, Cudjoe, FL 33042
MLS# 618820Listed by: COLDWELL BANKER SCHMITT LOWER KEYS (KW)
$2,100,000Active4 beds 3 baths2,440 sq. ft.22542 Jolly Roger Drive, Cudjoe, FL 33042
MLS# 618818Listed by: COLDWELL BANKER SCHMITT ISLAMORADA
$985,000Active3 beds 2 baths1,467 sq. ft.21855 Spain Boulevard, Cudjoe, FL 33042
MLS# 618817Listed by: COLDWELL BANKER SCHMITT LOWER KEYS (KW)
$869,000Active2 beds 2 baths960 sq. ft.154 Cutthroat Drive, Cudjoe, FL 33042
MLS# 618809Listed by: EXPERT REALTY LLC
$1,080,000Active3 beds 2 baths1,356 sq. ft.22852 Buccaneer Lane, Cudjoe, FL 33042
MLS# 618798Listed by: EXPERT REALTY LLC (HQ)
$669,000Active2 beds 2 baths816 sq. ft.701 Spanish Main Drive #374, Cudjoe, FL 33042
MLS# 618805Listed by: BLUESCAPE REAL ESTATE
$450,000Active0.06 Acres701 Spanish Main Drive #574, Cudjoe, FL 33042
MLS# 618734Listed by: BLUESCAPE REAL ESTATE
$375,000Active2 beds 1 baths726 sq. ft.701 Spanish Main Drive #536, Cudjoe, FL 33042
MLS# 618674Listed by: EXP REALTY LLC KW BRANCH
$465,000Active1 beds 1 baths799 sq. ft.701 Spanish Main Drive #455, Cudjoe, FL 33042
MLS# 618628Listed by: KELLER WILLIAMS KEY WEST COMPASS REALTY
$644,000Active2 beds 2 baths840 sq. ft.701 Spanish Main Drive #29, Cudjoe, FL 33042
MLS# 618622Listed by: BLUESCAPE REAL ESTATE
$410,000Active2 beds 2 baths864 sq. ft.701 Spanish Main Drive #635, Cudjoe, FL 33042
MLS# 618572Listed by: EXPERT REALTY LLC (HQ)
$765,000Active2 beds 2 baths865 sq. ft.701 Spanish Main Drive #LOT 102, Cudjoe, FL 33042
MLS# 618570Listed by: BLUESCAPE REAL ESTATE
$2,995,000Active4 beds 3 baths2,913 sq. ft.20920 5th Avenue, Cudjoe, FL 33042
MLS# 618526Listed by: COMPASS FLORIDA, LLC
$1,799,000Active3 beds 3 baths2,456 sq. ft.51 Sawyer Drive, Cudjoe, FL 33042
MLS# 618500Listed by: COLDWELL BANKER SCHMITT LOWER KEYS (KW)
$1,999,999Active3 beds 4 baths2,100 sq. ft.23087 Sailfish Lane, Cudjoe, FL 33042
MLS# 618494Listed by: COLDWELL BANKER SCHMITT LOWER KEYS (KW)
$445,000Active0.05 Acres701 Spanish Main Drive #LOT 496, Cudjoe, FL 33042
MLS# 618458Listed by: BLUESCAPE REAL ESTATE
$275,000Active0.05 Acres701 Spanish Main Drive #146, Cudjoe, FL 33042
MLS# 618426Listed by: EXPERT REALTY LLC (HQ)
$1,575,000Active3 beds 2 baths1,667 sq. ft.22865 Redfish Lane, Cudjoe, FL 33042
MLS# 618413Listed by: COLDWELL BANKER SCHMITT LOWER KEYS (KW)
$1,499,000Active3 beds 2 baths1,508 sq. ft.21250 Conch Drive, Cudjoe, FL 33042
MLS# 618382Listed by: COLDWELL BANKER SCHMITT LOWER KEYS (KW)
$899,000Active3 beds 2 baths1,203 sq. ft.153 Peg Leg Lane, Cudjoe, FL 33042
MLS# 618377Listed by: COLDWELL BANKER SCHMITT LOWER KEYS (KW)
$419,000Active2 beds 1 baths833 sq. ft.701 Spanish Main Drive #140, Cudjoe, FL 33042
MLS# 618353Listed by: COLDWELL BANKER SCHMITT RE CO.
$275,000Active1 beds 1 baths690 sq. ft.701 Spanish Main Drive #21, Cudjoe, FL 33042
MLS# 618299Listed by: EXPERT REALTY LLC (HQ)
$879,000Active2 beds 2 baths816 sq. ft.701 Spanish Main Drive #265, Cudjoe, FL 33042
MLS# 618239Listed by: EXPERT REALTY LLC (HQ)
$350,000Active2 beds 1 baths672 sq. ft.701 Spanish Main Drive #566, Cudjoe, FL 33042
MLS# 618228Listed by: BLUESCAPE REAL ESTATE
$915,000Active2 beds 2 baths816 sq. ft.701 Spanish Main Drive #47, Cudjoe, FL 33042
MLS# 618106Listed by: BLUESCAPE REAL ESTATE
$459,000Active1 beds 1 baths668 sq. ft.701 Spanish Main Drive #246, Cudjoe, FL 33042
MLS# 618098Listed by: BLUESCAPE REAL ESTATE
$1,699,000Active2 beds 2 baths1,344 sq. ft.1163 De Lussan Lane, Cudjoe, FL 33042
MLS# 618057Listed by: COLDWELL BANKER SCHMITT RE CO.
$430,000Active2 beds 1 baths415 sq. ft.21857 Disturbed Pine Road, Cudjoe, FL 33042
MLS# 618053Listed by: KELLER WILLIAMS KEY WEST COMPASS REALTY
$499,000Active2 beds 2 baths618 sq. ft.701 Spanish Main Drive #411, Cudjoe, FL 33042
MLS# 618027Listed by: SUZANNE MOORE REAL ESTATE
$980,000Active3 beds 2 baths1,456 sq. ft.131 Doubloon Lane, Cudjoe, FL 33042
MLS# 617960Listed by: BLUESCAPE REAL ESTATE
$575,000Active2 beds 2 baths861 sq. ft.701 Spanish Main Drive #444, Cudjoe, FL 33042
MLS# 617887Listed by: ACTION KEYS REALTY OF THE LOWER FL KEYS LLC
$1,325,000Active3 beds 2 baths1,494 sq. ft.22974 Anne Bonny Lane, Cudjoe, FL 33042
MLS# 617786Listed by: ISLAND WELCOME REAL ESTATE
$1,499,000Active3 beds 2 baths1,356 sq. ft.51 Drost Drive, Cudjoe, FL 33042
MLS# 617709Listed by: COLDWELL BANKER SCHMITT LOWER KEYS (KW)
$799,000Active2 beds 2 baths766 sq. ft.701 Spanish Main Drive #333\334, Cudjoe, FL 33042
MLS# 617687Listed by: BLUESCAPE REAL ESTATE
$255,000Active1 beds 1 baths368 sq. ft.701 Spanish Main Drive #533, Cudjoe, FL 33042
MLS# 617682Listed by: BLUESCAPE REAL ESTATE
$190,000Active0.14 Acres1145 Hakluyt Ln, Lower Keys, FL 33042
MLS# A11928965Listed by: UNITED REALTY GROUP INC
$879,000Active2 beds 2 baths861 sq. ft.701 Spanish Main Drive #512, Cudjoe, FL 33042
MLS# 617604Listed by: LOKATION REAL ESTATE
$999,000Active0.38 Acres21082 6th Avenue, Cudjoe, FL 33042
MLS# 617437Listed by: COLDWELL BANKER SCHMITT LOWER KEYS (KW)
$579,900Active2 beds 2 baths864 sq. ft.701 Spanish Main Drive #437, Cudjoe, FL 33042
MLS# 617465Listed by: BLUESCAPE REAL ESTATE
$2,195,000Active5 beds 3 baths1,903 sq. ft.125 Colson Drive, Cudjoe, FL 33042
MLS# 617496Listed by: BERKSHIRE HATHAWAY HOMESERVICES KNIGHT & GARDNER REALTY
$350,000Active0.05 Acres701 Spanish Main Drive #181, Cudjoe, FL 33042
MLS# 617506Listed by: WATERFRONT KEYS REALTY INC.
$1,099,000Active2 beds 2 baths1,284 sq. ft.22748 Blackbeard Lane, Cudjoe, FL 33042
MLS# 617545Listed by: EXP REALTY LLC
$480,000Active0.04 Acres701 Spanish Main Drive #432, Cudjoe, FL 33042
MLS# 617378Listed by: WATERFRONT KEYS REALTY INC.
$549,000Active2 beds 2 baths860 sq. ft.701 Spanish Main Drive #247, Cudjoe, FL 33042
MLS# 617289Listed by: BLUESCAPE REAL ESTATE
$650,000Active0.14 Acres22948 Drake Lane, Cudjoe, FL 33042
MLS# 617328Listed by: PREFERRED PROPERTIES (KW)
$899,000Active2 beds 2 baths864 sq. ft.701 Spanish Main Drive #221, Cudjoe, FL 33042
MLS# 617239Listed by: TRUMAN & CO. (KW)
$3,750,000Active3 beds 2 baths1,851 sq. ft.755 Sawyer Drive, Cudjoe, FL 33042
MLS# 617442Listed by: OCEAN SOTHEBY'S INTERNATIONAL REALTY
$430,000Active0.05 Acres701 Spanish Main Drive #551, Cudjoe, FL 33042
MLS# 617117Listed by: BLUESCAPE REAL ESTATE
$799,000Active2 beds 2 baths842 sq. ft.701 Spanish Main Drive #172, Cudjoe, FL 33042
MLS# 617097Listed by: BLUESCAPE REAL ESTATE
$1,499,000Active3 beds 2 baths1,944 sq. ft.20838 W 5th Avenue, Cudjoe, FL 33042
MLS# 617081Listed by: COLDWELL BANKER SCHMITT LOWER KEYS (KW)
$2,150,000Active3 beds 2 baths1,674 sq. ft.743 Pattison Drive, Cudjoe, FL 33042
MLS# 617067Listed by: ISLAND WELCOME REAL ESTATE
$1,125,000Active2 beds 2 baths1,008 sq. ft.22837 Calico Jack Circle, Cudjoe Key, FL 33042
MLS# 2066328Listed by: COLDWELL BANKER VANGUARD REALTY
$449,700Active2 beds 2 baths604 sq. ft.701 Spanish Main Drive #234, Cudjoe, FL 33042
MLS# 616834Listed by: BLUESCAPE REAL ESTATE
$539,000Active2 beds 2 baths836 sq. ft.701 Spanish Main Drive #154, Cudjoe, FL 33042
MLS# 616828Listed by: BLUESCAPE REAL ESTATE
$629,000Active2 beds 2 baths840 sq. ft.701 Spanish Main Drive #30, Cudjoe, FL 33042
MLS# 616817Listed by: BLUESCAPE REAL ESTATE
$2,795,000Active4 beds 3 baths2,951 sq. ft.20844 W 4th Avenue, Cudjoe, FL 33042
MLS# 616783Listed by: BERKSHIRE HATHAWAY HOMESERVICES KNIGHT & GARDNER REALTY
$225,000Active0.14 Acres124 Cutthroat Drive, Cudjoe, FL 33042
MLS# 616686Listed by: ISLAND LIFE REALTY EXPERTS
$255,000Active0.05 Acres701 Spanish Main Drive #642, Cudjoe, FL 33042
MLS# 617919Listed by: BLUESCAPE REAL ESTATE
$255,000Active0.05 Acres701 Spanish Main Drive #643, Cudjoe, FL 33042
MLS# 617920Listed by: BLUESCAPE REAL ESTATE- Open Tue, 10am to 1pm
$564,900Active2 beds 2 baths816 sq. ft.701 Spanish Main Drive #510, Cudjoe, FL 33042
MLS# 616317Listed by: BLUESCAPE REAL ESTATE 
$974,000Active3 beds 2 baths1,400 sq. ft.22954 Buccaneer Lane, Cudjoe, FL 33042
MLS# 616110Listed by: COLDWELL BANKER SCHMITT LOWER KEYS (KW)
$329,000Active2 beds 1 baths738 sq. ft.701 Spanish Main Drive #641, Cudjoe, FL 33042
MLS# 616003Listed by: COLDWELL BANKER SCHMITT RE CO.
$580,175Active2 beds 2 baths816 sq. ft.701 Spanish Main Drive #79, Cudjoe, FL 33042
MLS# 615962Listed by: KELLER WILLIAMS KEY WEST COMPASS REALTY
$569,700Active2 beds 1 baths718 sq. ft.701 Spanish Main Drive #335, Cudjoe, FL 33042
MLS# 615963Listed by: KELLER WILLIAMS KEY WEST COMPASS REALTY
$185,000Active0.14 AcresVacant Picard Lane, Cudjoe, FL 33042
MLS# 615956Listed by: KEYISLE REALTY
$1,529,999Active4 beds 3 baths2,136 sq. ft.142 Peg Leg Lane, Cudjoe, FL 33042
MLS# 615839Listed by: AMERIFIRST REALTY
$1,529,999Active4 beds 3 baths2,136 sq. ft.142 Peg Leg Ln, Lower Keys, FL 33042
MLS# A11840243Listed by: AMERIFIRST REALTY
$487,500Active2 beds 1 baths667 sq. ft.701 Spanish Main Drive #602, Cudjoe, FL 33042
MLS# 615408Listed by: BLUESCAPE REAL ESTATE
$925,000Active2 beds 1 baths806 sq. ft.701 Spanish Main Drive #49, Cudjoe, FL 33042
MLS# 617499Listed by: RE/MAX KEYS CONNECTION (KW)
$985,000Active2 beds 2 baths888 sq. ft.701 Spanish Main Drive #51, Cudjoe, FL 33042
MLS# 618707Listed by: EXPERT REALTY LLC (HQ)
$300,000Active0.05 Acres701 Spanish Main Drive #403, Cudjoe, FL 33042
MLS# 614911Listed by: EXPERT REALTY LLC (HQ)
$989,999Active3 beds 3 baths960 sq. ft.22961 John Avery Lane, Cudjoe, FL 33042
MLS# 614900Listed by: CASA MIAMI REAL ESTATE
$215,000Active0.05 Acres701 Spanish Main Drive #610, Cudjoe, FL 33042
MLS# 614876Listed by: BLUESCAPE REAL ESTATE
$374,000Active2 beds 2 baths748 sq. ft.701 Spanish Main Drive #543, Cudjoe, FL 33042
MLS# 614618Listed by: BLUESCAPE REAL ESTATE
$65,000Active0.14 Acres248 Yardarm Lane, Cudjoe, FL 33042
MLS# 614331Listed by: KELLER WILLIAMS KEY WEST COMPASS REALTY
$849,000Active3 beds 2 baths1,560 sq. ft.22920 Privateer Drive, Cudjoe, FL 33042
MLS# 614188Listed by: KELLER WILLIAMS KEY WEST COMPASS REALTY
$595,000Active2 beds 2 baths816 sq. ft.701 Spanish Main Drive #604, Cudjoe, FL 33042
MLS# 614094Listed by: BLUESCAPE REAL ESTATE
$214,500Active0.04 Acres701 Spanish Main Drive #658, Cudjoe, FL 33042
MLS# 614091Listed by: BLUESCAPE REAL ESTATE
$1,145,000Active3 beds 2 baths1,260 sq. ft.22737 Blackbeard Lane, Cudjoe, FL 33042
MLS# 616428Listed by: KELLER WILLIAMS KEY WEST COMPASS REALTY
$1,549,000Active3 beds 2 baths1,872 sq. ft.20841 W 8th Avenue, Cudjoe, FL 33042
MLS# 616914Listed by: COLDWELL BANKER SCHMITT LOWER KEYS (KW)
$499,000Active0.05 Acres701 Spanish Main Drive #384, Cudjoe, FL 33042
MLS# 617053Listed by: TRUMAN & CO. (KW)
$460,000Active1 beds 1 baths748 sq. ft.701 Spanish Main Drive #342, Cudjoe, FL 33042
MLS# 613572Listed by: BLUESCAPE REAL ESTATE
$999,999Active3 beds 2 baths2,198 sq. ft.21073 7th Avenue, Cudjoe, FL 33042
MLS# 613514Listed by: COLDWELL BANKER SCHMITT LOWER KEYS (KW)
$485,000Active1 beds 1 baths754 sq. ft.701 Spanish Main Drive #182, Cudjoe, FL 33042
MLS# 613336Listed by: BLUESCAPE REAL ESTATE
$259,000Active2 beds 1 baths664 sq. ft.701 Spanish Main Drive #457, Cudjoe, FL 33042
MLS# 613120Listed by: FLORIDA KEYS REALTY, INC.
$2,089,000Active5 beds 3 baths1,978 sq. ft.94 Sacarma Drive, Cudjoe, FL 33042
MLS# 615662Listed by: REALTY EXECUTIVES FLORIDA KEYS OLD TOWN
$487,000Active2 beds 2 baths864 sq. ft.701 Spanish Main Drive #659, Cudjoe, FL 33042
MLS# 612530Listed by: BLUESCAPE REAL ESTATE
$1,490,000Active2 beds 2 baths1,127 sq. ft.1113 De Lussan Lane, Cudjoe, FL 33042
MLS# 612427Listed by: COLDWELL BANKER SCHMITT LOWER KEYS (KW)
$839,000Active2 beds 2 baths640 sq. ft.701 Spanish Main Drive #97, Cudjoe, FL 33042
MLS# 617476Listed by: COLDWELL BANKER SCHMITT RE CO.
$445,000Active0.05 Acres701 Spanish Main Drive #183, Cudjoe, FL 33042
MLS# 617042Listed by: BLUESCAPE REAL ESTATE
$265,000Active0.05 Acres701 Spanish Main Drive #69, Cudjoe, FL 33042
MLS# 610861Listed by: BLUESCAPE REAL ESTATE
$1,125,000Active2 beds 2 baths1,008 sq. ft.22837 Calico Jack Circle, Cudjoe, FL 33042
MLS# 610732Listed by: COLDWELL BANKER VANGUARD REALTY
$899,000Active2 beds 2 baths1,120 sq. ft.22739 Buccaneer Lane, Cudjoe, FL 33042
MLS# 618732Listed by: COLDWELL BANKER SCHMITT LOWER KEYS (KW)
$12,999,999Active31 beds 19 baths21540 21470 Overseas Highway, Cudjoe, FL 33042
MLS# 610484Listed by: SELECT PROPERTIES OF NWFL
$525,000Active2 beds 2 baths816 sq. ft.701 Spanish Main Drive #453, Cudjoe, FL 33042
MLS# 618300Listed by: BLUESCAPE REAL ESTATE
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Information deemed reliable but not guaranteed. Information is provided, in part, by Greater Miami MLS. This information being provided is for consumer's personal, non-commercial use and may not be used for any other purpose other than to identify prospective properties consumers may be interested in purchasing.
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©2026 Century 21 Real Estate LLC. All rights reserved. CENTURY 21®, the CENTURY 21 Logo and C21® are service marks owned by Century 21 Real Estate LLC. Century 21 Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each office is independently owned and operated. Listing information is deemed reliable but not guaranteed accurate.
Protect your home and budget from life's surprises with an Assurant Home Warranty, backed by a partner that supports you through every step of homeownership. Explore Plans.
©2026 Century 21 Real Estate LLC. All rights reserved. CENTURY 21®, the CENTURY 21 Logo and C21® are service marks owned by Century 21 Real Estate LLC. Century 21 Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each office is independently owned and operated. Listing information is deemed reliable but not guaranteed accurate.