Cudjoe Key, FL Homes

/9
Not Listed For Sale
22819 Blackbeard Ln, Cudjoe Key, FL 33042

22819 Blackbeard Ln, Cudjoe Key, FL 33042

Selling your home? Sell it faster and for more with a Homes.com Boost.
Learn More
/37
$999,000
- 3 Beds
- 2 Baths
- 1,400 Sq Ft
22954 Buccaneer Ln, Summerland Key, FL 33042

Welcome to 22954 Buccaneer Ln, a quintessential Florida Keys waterfront escape. Perfectly positioned on a rare corner canal lot, this property offers 191 feet of concrete dockage with quick, unobstructed access to open water--ideal for serious boaters. The exterior's inviting Keys-style cedar siding blends seamlessly with lush tropical landscaping, creating a relaxed island vibe from the moment

Lisa Ferringo

Coldwell Banker Schmitt Lower Keys (KW)

(645) 230-1509

22954 Buccaneer Ln, Summerland Key, FL 33042
/35
$817,500 Sold Dec 01, 2025

22878 Privateer Dr, Summerland Key, FL 33042
- 2 Beds
- 2 Baths
- 948 Sq Ft
- Built 1989
Last Sold Summary
- 7% Below List Price
- $862/SF
- 133 Days On Market
Last Listing Agent Pamela Stangler Expert Realty LLC

22878 Privateer Dr, Summerland Key, FL 33042

/2
Est $613,887 Not Listed For Sale
- Studio
20874 4th Ave, Cudjoe Key, FL 33042

20874 4th Ave, Cudjoe Key, FL 33042

/43
$2,000,000
- 3 Beds
- 2 Baths
- 1,767 Sq Ft
22892 Jolly Roger Dr, Summerland Key, FL 33042

Open water views of Cudjoe Bay and the Atlantic. Enjoy gorgeous sunsets right in front of your dock. Spacious 3BR/2B, laundy room with a ton of storage. Lush landcaping, sandy beach great for launching paddleboards & kayaks. Modular, newly built in 2020. Spacious room sizes, open floorplan & high ceilings fill this home with light and create a relaxing flow. Close to the sandbars, Looe Key reef

Michelle Howerton

Brenda Donnelly Real Estate LLC

(855) 548-0123

22892 Jolly Roger Dr, Summerland Key, FL 33042
/3
$75,000 Sold Oct 10, 2025

0 Asturias Rd, Cudjoe Key, FL 33042
- Land
- 1.01 Acres
- $74,124 per Acre
Last Sold Summary
- 62% Below List Price
- 41 Days On Market
Last Listing Agent Maryann Warren Coldwell Banker - Ft. Lauderdale

0 Asturias Rd, Cudjoe Key, FL 33042

/2
Est $1,116,815 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,361 Sq Ft
21034 Overseas Hwy, Cudjoe Key, FL 33042

21034 Overseas Hwy, Cudjoe Key, FL 33042

/19
$250,000
- Land
701 Spanish Main Dr Unit 610, Cudjoe Key, FL 33042

Ocean ''peeks'' on this corner lot adds to the serenity you will get here at Lot 610 in the gated community of Venture Out on Cudjoe Key. Easy access on 2 sides of the lot.This property can do transient rentals!!As part of the Venture Out community, you'll enjoy an array of amenities at your doorstep. Dip into the massive saltwater swimming pool overlooking the ocean, or take advantage of the

Ian Calderwood

Bluescape Real Estate

(786) 761-5180

701 Spanish Main Dr Unit 610, Cudjoe Key, FL 33042
/2
$600,000 Sold Jul 14, 2025

701 Spanish Main Dr Unit 573, Cudjoe Key, FL 33042
- 2 Beds
- 2 Baths
- 816 Sq Ft
- Built 1993
Last Sold Summary
- 14% Below List Price
- $735/SF
- 56 Days On Market
Last Listing Agent Kim Babenzien Expert Realty LLC (HQ)

701 Spanish Main Dr Unit 573, Cudjoe Key, FL 33042

/2
Not Listed For Sale
- 7,000 Sq Ft
1138 Basque Ln, Summerland Key, FL 33042

1138 Basque Ln, Summerland Key, FL 33042

/39
$1,599,000
- 3 Beds
- 2 Baths
- 1,944 Sq Ft
20838 5th Ave W, Summerland Key, FL 33042

Discover the ultimate boating lifestyle in the Florida Keys with this beautiful Deep Draft Canal Front Pool Home in the exclusive waterfront enclave of Cudjoe Gardens. Set on an expansive 11,000 sq ft lot with 100 feet of waterfront, this ground-level, above-flood concrete ranch home offers seamless access to the Pool and water. Inside, enjoy nearly 2,000 square feet of living space with 3

Lisa Ferringo

Coldwell Banker Schmitt Lower Keys (KW)

(786) 952-7261

20838 5th Ave W, Summerland Key, FL 33042
/2
$49,000 Sold Oct 03, 2025

Lot 24 Rainbow Beach, Big Torch Key, FL 33042
- Land
Last Sold Summary
- 6% Below List Price
- 50 Days On Market
Last Listing Agent Pamela Stangler Expert Realty LLC

Lot 24 Rainbow Beach, Big Torch Key, FL 33042

/61
Est $2,624,359 Not Listed For Sale
- 4 Beds
- 3 Baths
- 3,042 Sq Ft
20886 4th Ave W, Summerland Key, FL 33042

20886 4th Ave W, Summerland Key, FL 33042

/60
$529,000
- 2 Beds
- 1 Bath
- 667 Sq Ft
701 Spanish Main Dr Unit 602, Cudjoe Key, FL 33042

Oceanfront Paradise Awaits!Unit 602 in Venture OutExperience the epitome of Florida living in this charming Two-bedroom, one-bathroom mid-rise mobile home nestled within an exclusive gated community.This beautiful canal front home with ocean views from the backyard home boasts:* Prime Canal front Location: Enjoy breathtaking ocean views and direct access to the water from your private 35 ft

Ian Calderwood

Bluescape Real Estate

(786) 981-9841

701 Spanish Main Dr Unit 602, Cudjoe Key, FL 33042
/3
$420,000 Sold Jun 27, 2025

701 Spanish Main Dr Unit 175, Cudjoe Key, FL 33042
- 1 Bed
- 1 Bath
- 488 Sq Ft
- Built 1999
Last Sold Summary
- 13% Below List Price
- $861/SF
- 0 Days On Market
Last Listing Agent Joyce Craul Expert Realty LLC (HQ)

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

/39
Not Listed For Sale
- 2 Beds
- 2 Baths
- 864 Sq Ft
701 Spanish Main Dr Unit 149, Cudjoe Key, FL 33042

701 Spanish Main Dr Unit 149, Cudjoe Key, FL 33042

/66
$849,000
- 2 Beds
- 2 Baths
- 842 Sq Ft
701 Spanish Main Dr Unit 172, Cudjoe Key, FL 33042

Canal Front Oasis w/ Ocean Views & Resort Amenities | Income Producing Gem Escape to your own slice of paradise in the highly sought-after, gated resort community of Venture Out on Cudjoe Key! This stunning 2-bedroom, 2-bathroom high-rise home offers the ultimate Florida Keys lifestyle, combining tranquil canal-front living with breathtaking ocean views and an incredible array of world-class

Ian Calderwood

Bluescape Real Estate

(786) 841-6970

701 Spanish Main Dr Unit 172, Cudjoe Key, FL 33042
/75
$830,000 Sold Sep 15, 2025

22738 Blackbeard Ln, Summerland Key, FL 33042
- 2 Beds
- 2 Baths
- 1,200 Sq Ft
- Built 1989
Last Sold Summary
- 17% Below List Price
- $692/SF
- 84 Days On Market
Current Estimated Value $834,452

Last Listing Agent Tommy Mack Coastal Collection Real Estate Inc.

22738 Blackbeard Ln, Summerland Key, FL 33042

/2
Est $315,333 Not Listed For Sale
- Studio
27328 St Vincent Ln, Ramrod Key, FL 33042

27328 St Vincent Ln, Ramrod Key, FL 33042

/55
$1,500,000 Open Sun 11AM - 1PM
- 3 Beds
- 2 Baths
- 1,467 Sq Ft
21865 Spain Blvd, Summerland Key, FL 33042

Majestically positioned at the end of Spain Blvd, within the Prestigious Cudjoe Acres neighborhood. Discover 21855 & 21865 Spain Blvd. A Property that offers the kind of privacy that's almost impossible to find in the Florida Keys. Set on over 3 acres of land, this one-of-a-kind property is surrounded by naturally occurring native plants, mature trees, and freshwater ponds that encourage local

Matthew Sheehan

Ocean Sotheby's International Realty

(645) 215-8837

21865 Spain Blvd, Summerland Key, FL 33042
/41
$1,105,000 Sold Sep 26, 2025

22946 Bluegill Ln, Summerland Key, FL 33042
- 2 Beds
- 2 Baths
- 1,200 Sq Ft
- Built 1975
Last Sold Summary
- 14% Below List Price
- $921/SF
- 255 Days On Market
Last Listing Agent Anneliese Dietrick Coldwell Banker Schmitt Lower Keys (KW)

22946 Bluegill Ln, Summerland Key, FL 33042

/49
Est $350,899 Not Listed For Sale
701 Spanish Main Dr Unit 557, Cudjoe Key, FL 33042

701 Spanish Main Dr Unit 557, Cudjoe Key, FL 33042

/61
$2,250,000
- 3 Beds
- 2 Baths
- 1,674 Sq Ft
743 Pattison Dr, Summerland Key, FL 33042

Welcome to your slice of paradise in the Florida Keys! This stunning 3-bedroom, 2-bath canal-front home in desirable Cudjoe Gardens celebrates everything we love about island life -- in shades of blue. From the moment you arrive, you'll feel the calm, coastal vibe this home radiates.Beautifully remodeled in 2021 with full permits, this residence offers an open-concept living area with soaring

Sandra Tuttle

Island Welcome Real Estate

(786) 756-9163

743 Pattison Dr, Summerland Key, FL 33042
/57
$1,375,000 Sold Apr 17, 2025

468 Sawyer Dr, Summerland Key, FL 33042
- 4 Beds
- 4 Baths
- 1,797 Sq Ft
- Built 1972
Last Sold Summary
- 19% Below List Price
- $765/SF
- 215 Days On Market
Current Estimated Value $1,389,707

Last Listing Agent Stacy Shahan Island Real Estate Company Florida Keys

468 Sawyer Dr, Summerland Key, FL 33042

/8
Est $451,836 Not Listed For Sale
17256 Keystone Rd, Sugarloaf Key, FL 33042

17256 Keystone Rd, Sugarloaf Key, FL 33042

/33
$329,000
- 1 Bed
- 1 Bath
- 690 Sq Ft
701 Spanish Main Dr Unit 21, Cudjoe Key, FL 33042

Cozy 1-Bedroom 1-bathroom Mobile Home with Enchanting Florida RoomLocated inside the very desirable Venture Out Gated Community.This charming and very well kept mobile home offers a comfortable and affordable living space. Key Features:* Fully tiled.* Comfortable Bedroom: With plenty of large windows. * Fully equipped kitchen with table, chairs and a built in desk.* Full Bathroom: Includes

Ian Calderwood

Bluescape Real Estate

(786) 550-7131

701 Spanish Main Dr Unit 21, Cudjoe Key, FL 33042
/115
$12,250,000 Sold May 07, 2025

785 Sawyer Dr, Cudjoe Key, FL 33042
- 7 Beds
- 6 Baths
- 4,888 Sq Ft
- Built 2019
Last Sold Summary
- 5% Below List Price
- $2,506/SF
- 44 Days On Market
Current Estimated Value $4,840,918

Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

785 Sawyer Dr, Cudjoe Key, FL 33042

/2
Not Listed For Sale
23008 Overseas Hwy, Cudjoe Key, FL 33042

23008 Overseas Hwy, Cudjoe Key, FL 33042

/47
$569,900
- 2 Beds
- 2 Baths
- 816 Sq Ft
701 Spanish Main Dr Unit 510, Cudjoe Key, FL 33042

Oceanfront Paradise Awaits!Unit 510 in Venture OutExperience the epitome of waterfront Florida living in this charming two-bedroom, two-bathroom mid-rise mobile home nestled within an exclusive gated community.This beautiful canal front home boasts:* Prime Canal front Location: Enjoy direct access to the water from your private 35 ft seawall.* Community Boat Ramp and boat washdown station.*

Ian Calderwood

Bluescape Real Estate

(786) 686-7983

701 Spanish Main Dr Unit 510, Cudjoe Key, FL 33042
/26
$239,000 Sold Jun 30, 2025

701 Spanish Main Dr Unit 6, Cudjoe Key, FL 33042
- Land
Last Sold Summary
- 2% Below List Price
- 74 Days On Market
Current Estimated Value $244,697

Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

701 Spanish Main Dr Unit 6, Cudjoe Key, FL 33042

/14
Est $454,559 Not Listed For Sale
- 1 Bed
701 Spanish Main Dr Unit 432, Cudjoe Key, FL 33042

701 Spanish Main Dr Unit 432, Cudjoe Key, FL 33042

/74
$799,000
- 2 Beds
- 2 Baths
- 766 Sq Ft
701 Spanish Main Dr Unit 333,334, Cudjoe Key, FL 33042

Canal Front Oasis with Resort Amenities!Nightly Rentals Allowed!Income Producing Gem!RARE-DOUBLE LOT!! Allows 2 cars with 2 separate driveways. Massive 69' Seawall!RARE-DAVITS for your boat!! Escape to your own slice of paradise in the highly sought-after, gated resort community of Venture Out on Cudjoe Key! This stunning 2-bedroom, 2-bathroom mid-rise home offers the ultimate Florida Keys

Ian Calderwood

Bluescape Real Estate

(844) 482-8589

701 Spanish Main Dr Unit 333,334, Cudjoe Key, FL 33042
/57
$2,800,000 Sold Oct 30, 2025

22967 Redfish Ln, Cudjoe Key, FL 33042
- 3 Beds
- 4 Baths
- 3,747 Sq Ft
- Built 2019
Last Sold Summary
- 7% Below List Price
- $747/SF
- 37 Days On Market
Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Lower Keys (KW)

22967 Redfish Ln, Cudjoe Key, FL 33042

/2
Est $827,905 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,404 Sq Ft
53 Gold Boullion Rd, Cudjoe Key, FL 33042

53 Gold Boullion Rd, Cudjoe Key, FL 33042

/38
$1,499,000
- 3 Beds
- 2 Baths
- 1,356 Sq Ft
51 Drost Dr, Summerland Key, FL 33042

Originally built as the developer of Cudjoe Gardens personal residence, this exceptional Mid-Century Modern waterfront home captures the effortless glamour of Palm Springs design blended with the laid-back sophistication of the Florida Keys. Offering 3 Bedrooms and 2 Baths, the residence has been beautifully remodeled with meticulous attention to detail, honoring its architectural roots while

Lisa Ferringo

Coldwell Banker Schmitt Lower Keys (KW)

(786) 551-4933

51 Drost Dr, Summerland Key, FL 33042
/29
$395,000 Sold May 19, 2025

701 Spanish Main Dr Unit 84, Cudjoe Key, FL 33042
- Land
Last Sold Summary
- 5% Below List Price
- 78 Days On Market
Current Estimated Value $390,403

Last Listing Agent Kim Babenzien Expert Realty LLC (HQ)

701 Spanish Main Dr Unit 84, Cudjoe Key, FL 33042

/69
Not Listed For Sale
- 1 Bed
- 1 Bath
- 420 Sq Ft
701 Spanish Main Dr Unit 554, Cudjoe Key, FL 33042

701 Spanish Main Dr Unit 554, Cudjoe Key, FL 33042

/4
$285,000
- Land
Unlisted Address

Private Acre on Cudjoe Key. Lush, Tropical, and Near the Water Escape to your own secluded paradise in the Lower Keys! This just over an acre lot on Cudjoe Key is surrounded by beautiful equestrian properties and dense tropical foliage, offering unmatched privacy and tranquility. Located just seconds from a public boat ramp, you'll have easy access to world-class fishing, boating, and

Coby Taylor

Taylor & Assoc. RE, Inc.

(786) 876-6382

Unlisted Address
/51
$420,000 Sold Nov 21, 2025

701 Spanish Main Dr Unit 280, Cudjoe Key, FL 33042
- 1 Bed
- 1 Bath
- 816 Sq Ft
- Built 1979
Last Sold Summary
- 8% Below List Price
- $515/SF
- 185 Days On Market
Last Listing Agent Kelly Gardner Bluescape Real Estate

701 Spanish Main Dr Unit 280, Cudjoe Key, FL 33042

/66
Not Listed For Sale
- 2 Beds
701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042

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

Showing Results 41 - 80, Page 2 of 18

Florida Monroe County Cudjoe Key

How to Buy a Home How to Finance a Home How to Sell a Home

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

Homes in Nearby Neighborhoods

Homes in Nearby Cities

Homes in Nearby Counties

Monroe County Homes

Homes in Nearby Zip Codes

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage