Cudjoe Key, FL homes for sale & real estate

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3D WALKTHROUGH

21855 Spain Blvd, Summerland Key, FL 33042
21855 Spain Blvd, Summerland Key, FL 33042
21855 Spain Blvd, Summerland Key, FL 33042
ABOUT THIS HOME
Cudjoe Key, FL Homes for Sale
Just over An acre of paradise in the Florida Keys—21855 Spain Boulevard is more than a home, it's a private retreat designed for those who value both space and privacy. Rarely does a property offer this combination of land, privacy, all just moments from open water. Set on over an acre of lush, natural landscape, the residence is thoughtfully positioned to create a sense of sanctuary from the moment you arrive. Inside, light-filled interiors flow effortlessly. Step outside and the true essence of Keys living unfolds. A sparkling pool anchors the property, offering the perfect backdrop for relaxation or entertaining. With expansive grounds surrounding you, there is room to further cult

$1,250,000

3 beds2 baths1,467 sq ft

21855 Spain Blvd, Summerland Key, FL 33042

Private retreat • Expansive grounds • 1.01 acre lot

NEW CONSTRUCTION

22737 Blackbeard Ln, Summerland Key, FL 33042
22737 Blackbeard Ln, Summerland Key, FL 33042
22737 Blackbeard Ln, Summerland Key, FL 33042
ABOUT THIS HOME
Cudjoe Key, FL Homes for Sale
Welcome home to your coastal oasis! This stunning brand-new elevated home features three bedrooms, two bathrooms, with an open concept living room and kitchen plus a covered 10x30 porch. Additional features include impact resistance windows and doors, metal roof, Azek decking, powder coated aluminum railings, custom concrete dock (8x20) with a permitted 12,000 Ibs. boat lift with 298 sq. ft. of enclosed storage space. Schedule your private showing today! One of the Sellers is a Licensed FL Real Estate Sales Associate.

$1,175,000

3 beds2 baths1,260 sq ft

22737 Blackbeard Ln, Summerland Key, FL 33042

Covered porch • Metal roof • Custom concrete dock

3D WALKTHROUGH

22852 John Silver Ln, Summerland Key, FL 33042
22852 John Silver Ln, Summerland Key, FL 33042
22852 John Silver Ln, Summerland Key, FL 33042
ABOUT THIS HOME
Cudjoe Key, FL Homes for Sale
Paradise Awaits on Cudjoe Key Discover 22852 John Silver Lane, a rare A-frame waterfront retreat in the peaceful Cutthroat Harbor Estates. This two-bedroom, two-bath home embodies the perfect balance of Keys character and modern comfort, wrapped in lush palms and native landscaping that create a true island sanctuary. Inside, soaring vaulted ceilings and impact-rated windows and doors fill the space with natural light, highlighting rich hardwood floors and stylish finishes throughout. In addition to the two bedrooms, a versatile upper level bonus space currently used as a 3rd bedroom, could be second living room, lounge or an office. With the option to enclose it for a private third bedroom

$949,000

2 beds2 baths1,620 sq ft

22852 John Silver Ln, Summerland Key, FL 33042

Canal-front patio • Deep-water canal • Open-air loft

165 Cutlass Ln, Summerland Key, FL 33042
165 Cutlass Ln, Summerland Key, FL 33042
165 Cutlass Ln, Summerland Key, FL 33042
ABOUT THIS HOME
Cudjoe Key, FL Homes for Sale
Discover Your Dream Waterfront Home in the Florida Keys! This stunning canal-front residence boasts 4 spacious bedrooms and 3 bathrooms. With 2,448 sq. ft. of thoughtfully laid-out living space, this home is perfect for accommodating large families and entertaining guests. Step onto the expansive covered balconies on both floors, where you can relax and take in the serene canal views. The generous kitchen and dining area serve as the heart of the home, ideal for hosting memorable gatherings. Each updated bathroom radiates modern sophistication, while the roomy master suite provides a private sanctuary for relaxation. The exterior of the property offers ample off-street parking and the poten

$1,175,000

4 beds3 baths2,448 sq ft

165 Cutlass Ln, Summerland Key, FL 33042

Serene canal views • Generous kitchen • Waterfront home

22464 La Fitte Dr, Summerland Key, FL 33042
22464 La Fitte Dr, Summerland Key, FL 33042
22464 La Fitte Dr, Summerland Key, FL 33042
ABOUT THIS HOME
Cudjoe Key, FL Homes for Sale
Cudjoe Key Canal Front Living — Newly renovated home with covered carport, custom master bath, real wood slim shaker cabinets, quartz countertops, and new appliances and A/C. Features impact doors/sliders, new floors, and fresh P-rock landscaping. Two open porches overlook a 60' canal for relaxing or entertaining. Permitted storage below is ideal for gear or tools. Yard is a blank slate—build your tropical retreat or ample amount of parking for all your toys! Bring the RV, boat, jet skis and more. Just a short ride for all the fun Key West has to offer and minutes to the grocery store. Incredible fishing and diving in your backyard, go play at Looe key, picnic island and the ree

$799,000

2 beds2 baths860 sq ft

22464 La Fitte Dr, Summerland Key, FL 33042

New floors • Quartz countertops • Canal front living

Property at 22922 Blackbeard Ln, Summerland Key, FL 33042, 3 beds, 2 baths

$995,000

3 beds2 baths1,195 sq ft

22922 Blackbeard Ln, Summerland Key, FL 33042

Property at 22562 Jolly Roger Dr, Summerland Key, FL 33042, 4 beds, 2 baths

$1,925,000

4 beds2 baths2,074 sq ft

22562 Jolly Roger Dr, Summerland Key, FL 33042

Property at 701 Spanish Main Dr #495, Cudjoe Key, FL 33042, 2 beds, 2 baths

$650,000

2 beds2 baths816 sq ft

701 Spanish Main Dr #495, Cudjoe Key, FL 33042

Property at 22815 Port Royal Ln, Summerland Key, FL 33042, 4 beds, 4.5 baths

$3,750,000

4 beds4.5 baths3,228 sq ft

22815 Port Royal Ln, Summerland Key, FL 33042

Property at 653 Sawyer Dr, Summerland Key, FL 33042, 3 beds, 2 baths

$2,999,999

3 beds2 baths1,714 sq ft

653 Sawyer Dr, Summerland Key, FL 33042

Property at 701 Spanish Main Dr #510, Cudjoe Key, FL 33042, 2 beds, 2 baths

$589,900

2 beds2 baths816 sq ft

701 Spanish Main Dr #510, Cudjoe Key, FL 33042

Property at 701 Spanish Main Dr #51, Cudjoe Key, FL 33042, 2 beds, 2 baths

$985,000

2 beds2 baths888 sq ft

701 Spanish Main Dr #51, Cudjoe Key, FL 33042

Property at 22954 Buccaneer Ln, Summerland Key, FL 33042, 3 beds, 2 baths

$999,000

3 beds2 baths1,400 sq ft

22954 Buccaneer Ln, Summerland Key, FL 33042

Property at 701 Spanish Main Dr #641, Cudjoe Key, FL 33042, 2 beds, 1 bath

$299,000

2 beds1 bath738 sq ft

701 Spanish Main Dr #641, Cudjoe Key, FL 33042

Property at 22970 Gasparilla Ln, Summerland Key, FL 33042, 3 beds, 2 baths

$2,325,000

3 beds2 baths2,050 sq ft

22970 Gasparilla Ln, Summerland Key, FL 33042

Property at 20889 W 7th Ave, Summerland Key, FL 33042, 3 beds, 2.5 baths

$1,975,000

3 beds2.5 baths2,295 sq ft

20889 W 7th Ave, Summerland Key, FL 33042

Property at 22841 Buccaneer Ln, Summerland Key, FL 33042, 3 beds, 3 baths

$1,079,000

3 beds3 baths1,920 sq ft

22841 Buccaneer Ln, Summerland Key, FL 33042

Property at 20771 W 2nd Ave, Summerland Key, FL 33042, 3 beds, 2 baths

$1,990,000

3 beds2 baths2,047 sq ft

20771 W 2nd Ave, Summerland Key, FL 33042

Property at 22878 Privateer Dr, Summerland Key, FL 33042, 2 beds, 2 baths

$875,000

2 beds2 baths948 sq ft

22878 Privateer Dr, Summerland Key, FL 33042

Property at 701 Spanish Main Dr #635, Cudjoe Key, FL 33042, 2 beds, 2 baths

$425,000

2 beds2 baths864 sq ft

701 Spanish Main Dr #635, Cudjoe Key, FL 33042

Property at 22865 Redfish Ln, Summerland Key, FL 33042, 3 beds, 2 baths

$1,699,000

3 beds2 baths1,667 sq ft

22865 Redfish Ln, Summerland Key, FL 33042

Property at 1176 Thatch Ln, Summerland Key, FL 33042, 2 beds, 2 baths

$2,650,000

2 beds2 baths1,577 sq ft

1176 Thatch Ln, Summerland Key, FL 33042

Property at 701 Spanish Main Dr #533, Cudjoe Key, FL 33042, 1 bed, 1 bath

$279,000

1 bed1 bath368 sq ft

701 Spanish Main Dr #533, Cudjoe Key, FL 33042

Property at 164 Tortuga Ln, Summerland Key, FL 33042, 3 beds, 2 baths

$1,199,000

3 beds2 baths1,400 sq ft

164 Tortuga Ln, Summerland Key, FL 33042

Property at 701 Spanish Main Dr #79, Cudjoe Key, FL 33042, 2 beds, 2 baths

$580,175

2 beds2 baths816 sq ft

701 Spanish Main Dr #79, Cudjoe Key, FL 33042

Property at 142 Peg Leg Ln, Summerland Key, FL 33042, 4 beds, 3 baths

$1,599,999

4 beds3 baths2,136 sq ft

142 Peg Leg Ln, Summerland Key, FL 33042

(305) 595-8616

Property at 22961 John Avery Ln, Summerland Key, FL 33042, 3 beds, 3 baths

$989,999

3 beds3 baths960 sq ft

22961 John Avery Ln, Summerland Key, FL 33042

Property at 94 Sacarma Dr, Summerland Key, FL 33042, 5 beds, 3 baths

$2,300,000

5 beds3 baths1,978 sq ft

94 Sacarma Dr, Summerland Key, FL 33042

Property at 489 Sawyer Dr, Summerland Key, FL 33042, 2 beds, 2 baths

$1,950,000

2 beds2 baths1,281 sq ft

489 Sawyer Dr, Summerland Key, FL 33042

Property at 701 Spanish Main 369, 370 Dr #369, Cudjoe Key, FL 33042, 2 beds, 2 baths

$999,965

2 beds2 baths840 sq ft

701 Spanish Main 369, 370 Dr #369, Cudjoe Key, FL 33042

Property at 37 N Yardarm Ln #1, Cudjoe Key, FL 33042, 2 beds, 2 baths

$450,000

2 beds2 baths980 sq ft

37 N Yardarm Ln #1, Cudjoe Key, FL 33042

Property at 701 Spanish Main Dr #62, Cudjoe Key, FL 33042, 2 beds, 1 bath

$329,000

2 beds1 bath756 sq ft

701 Spanish Main Dr #62, Cudjoe Key, FL 33042

Property at 701 Spanish Main Dr #335, Cudjoe Key, FL 33042, 2 beds, 1 bath

$569,700

2 beds1 bath718 sq ft

701 Spanish Main Dr #335, Cudjoe Key, FL 33042

Property at 21540 21470 Overseas Hwy, Summerland Key, FL 33042, 31 beds, 19 baths

$13,495,000

31 beds19 baths— sq ft

21540 21470 Overseas Hwy, Summerland Key, FL 33042

Property at 22920 Privateer Dr, Summerland Key, FL 33042, 3 beds, 2 baths

$849,000

3 beds2 baths1,560 sq ft

22920 Privateer Dr, Summerland Key, FL 33042

Property at 701 Spanish Main Dr #543, Cudjoe Key, FL 33042, 2 beds, 1.5 baths

$374,000

2 beds1.5 baths748 sq ft

701 Spanish Main Dr #543, Cudjoe Key, FL 33042

Property at 701 Spanish Main Dr #444, Cudjoe Key, FL 33042, 2 beds, 2 baths

$625,000

2 beds2 baths861 sq ft

701 Spanish Main Dr #444, Cudjoe Key, FL 33042

Property at 701 Spanish Main Dr #625, Cudjoe Key, FL 33042, 2 beds, 1 bath

$344,999

2 beds1 bath720 sq ft

701 Spanish Main Dr #625, Cudjoe Key, FL 33042

Property at 701 Spanish Main Dr #49, Cudjoe Key, FL 33042, 2 beds, 1 bath

$925,000

2 beds1 bath806 sq ft

701 Spanish Main Dr #49, Cudjoe Key, FL 33042

Property at 701 Spanish Main Dr #214, Cudjoe Key, FL 33042, 2 beds, 2 baths

$997,000

2 beds2 baths779 sq ft

701 Spanish Main Dr #214, Cudjoe Key, FL 33042

Property at 701 Spanish Main Dr #175, Cudjoe Key, FL 33042, 1 bed, 1 bath

$359,000

1 bed1 bath488 sq ft

701 Spanish Main Dr #175, Cudjoe Key, FL 33042

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Average home prices near Cudjoe Key, FL

Cities

Zip Codes

33042 homes for sale
$1,221,000

Cudjoe Key, FL real estate trends

All Home Types trends in Cudjoe Key, FL

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$1,075,000

-14.0% YoY | Jul 2025

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Jul 2025

Growth

% YoY

Cudjoe Key, FL

$1,075,000

-14.0%

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