Cudjoe Key, FL Homes

/91
$1,200,000 Under Contract
- 3 Beds
- 2 Baths
- 1,467 Sq Ft
21855 Spain Blvd, Summerland Key, FL 33042

Imagine owning a pool home and 3.3 private acres in the Florida Keys - this rare opportunity is in Cudjoe Acres, an equestrian area just 20 miles from Key West, with two equestrian facilities just around the corner. The home sits on one secluded acre surrounded by a botanical garden of impressive plantings including rare palm trees, buttonwoods, orchids, dragon fruit cactus, fragrant Joe wood, a

Patti Nickless

Coldwell Banker Schmitt Lower Keys (KW)

(645) 225-2307

21855 Spain Blvd, Summerland Key, FL 33042
Explore Cudjoe Key
/70
$12,500 per month
- 4 Beds
- 4 Baths
- 2,952 Sq Ft
- Property for Rent
21640 Overseas Hwy, Summerland Key, FL 33042

Waterfront Paradise in Cudjoe KeyWelcome to 21640 Overseas Highway, Cudjoe Key, FL 33042--a spectacular 4-bedroom, 4-bathroom waterfront sanctuary offering panoramic open-water views and the ultimate Florida Keys lifestyle.Inside, the home features a beautifully updated kitchen with modern finishes, spacious living areas designed for comfort and entertaining, and a huge master suite overlooking

Dan Serban

Key West Luxury Real Estate Inc (KW)

(786) 442-3255

21640 Overseas Hwy, Summerland Key, FL 33042
/2
$1,030,000 Sold Nov 19, 2025

22521 Jolly Roger Dr, Cudjoe Key, FL 33042
- 4 Beds
- 3 Baths
- 1,728 Sq Ft
- Built 2010
Last Sold Summary
- $596/SF
- 0 Days On Market
Current Estimated Value $1,027,186

Last Listing Agent Patti Nickless Coldwell Banker Schmitt Lower Keys (KW)

22521 Jolly Roger Dr, Cudjoe Key, FL 33042

/29
Not Listed For Sale

701 Spanish Main Dr Unit 478, Cudjoe Key, FL 33042
- 2 Beds
- 2 Baths
- 828 Sq Ft
- Built 2001
701 Spanish Main Dr Unit 478, Cudjoe Key, FL 33042

Last Sold Summary
- $966/SF
- 14 Days On Market
Last Sold Price $800,000

Last Listing Agent Susan Rich Select Properties of NWFL

/19
$215,000
- 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
/12

$2,500 per month

Coco Palms

2 Beds

21585 Overseas Hwy, Cudjoe Key, FL 33042

Discover our newly constructed community at Coco Palms in Cudjoe Key, Florida. The leasing team will assist you in finding your new place. A selection of amenities are waiting for you: hurricane windows and doors, dishwashers, washers and dryers and convenient on-site parking options. Contact us today to see available floor plans and find your new place at Coco Palms.

21585 Overseas Hwy, Cudjoe Key, FL 33042
/45
$630,000 Sold Dec 08, 2025

22970 Sharp Ln, Summerland Key, FL 33042
- 1 Bed
- 1 Bath
- 576 Sq Ft
- Built 1985
Last Sold Summary
- 10% Below List Price
- $1,094/SF
- 4 Days On Market
Current Estimated Value $662,671

Last Listing Agent Nick Boumerhi Meyer and Boumerhi Realty LLC

22970 Sharp Ln, Summerland Key, FL 33042

/15
Not Listed For Sale

8 Calico Jack Circle Cir, Verifying, FL 33042
8 Calico Jack Circle Cir, Verifying, FL 33042

Last Sold Summary
- 18 Days On Market
Last Sold Price $165,000

Last Listing Agent Beata Sharpe COLDWELL BANKER VANGUARD REALTY

/39
$1,499,000
- 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 Real Estate Co

(786) 952-7261

20838 5th Ave W, Summerland Key, FL 33042
/59
$860,300 Sold May 02, 2025

701 Spanish Main Dr Unit 198, Cudjoe Key, FL 33042
- 2 Beds
- 2 Baths
- 864 Sq Ft
- Built 2000
Last Sold Summary
- 9% Below List Price
- $996/SF
- 76 Days On Market
Last Listing Agent Kelly Gardner Bluescape Real Estate

701 Spanish Main Dr Unit 198, Cudjoe Key, FL 33042

/40
Not Listed For Sale

701 Spanish Main Dr Unit 366, Cudjoe Key, FL 33042
- 2 Beds
- 2 Baths
- 816 Sq Ft
- Built 1996
701 Spanish Main Dr Unit 366, Cudjoe Key, FL 33042

Last Sold Summary
- $674/SF
- 22 Days On Market
Last Sold Price $550,000

Last Listing Agent Ian Calderwood Bluescape Real Estate

/60
$487,500
- 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
/2
$55,000 Sold Oct 22, 2025

Lot 2 Rainbow Beach, Big Torch Key, FL 33042
- Land
Last Sold Summary
- 4% Below List Price
- 2 Days On Market
Last Listing Agent Pamela Stangler Expert Realty LLC

Lot 2 Rainbow Beach, Big Torch Key, FL 33042

/35
Est $237,051 Not Listed For Sale

701 Spanish Main Dr Unit 647, Cudjoe Key, FL 33042
701 Spanish Main Dr Unit 647, Cudjoe Key, FL 33042

Last Sold Summary
- 9% Above List Price
- 22 Days On Market
Last Sold Price $217,000

Last Listing Agent Kelly Gardner Bluescape Real Estate

/66
$799,000
- 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
/47
$1,100,000 Sold Jun 27, 2025

21014 7th Ave, Summerland Key, FL 33042
- 3 Beds
- 2 Baths
- 1,361 Sq Ft
- Built 1988
Last Sold Summary
- 19% Below List Price
- $808/SF
- 102 Days On Market
Current Estimated Value $1,104,572

Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

21014 7th Ave, Summerland Key, FL 33042

/51
Not Listed For Sale

701 Spanish Main Dr Unit 167, Cudjoe Key, FL 33042
- 2 Beds
- 2 Baths
- 864 Sq Ft
- Built 2006
701 Spanish Main Dr Unit 167, Cudjoe Key, FL 33042

Last Sold Summary
- $899/SF
- 27 Days On Market
Last Sold Price $777,000

Last Listing Agent Kelly Gardner Bluescape Real Estate

/47
$559,000 Open Thu 10:30AM - 1:30PM
- 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
/42
$1,900,000 Sold Jun 29, 2025

20867 5th Ave W, Cudjoe Key, FL 33042
- 3 Beds
- 2 Baths
- 1,702 Sq Ft
- Built 2011
Last Sold Summary
- 5% Below List Price
- $1,116/SF
- 17 Days On Market
Current Estimated Value $1,874,633

Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

20867 5th Ave W, Cudjoe Key, FL 33042

/21
Not Listed For Sale

701 Spanish Main Dr Unit 83, Cudjoe Key, FL 33042
- 2 Beds
- 1 Bath
- 770 Sq Ft
- Built 1978
701 Spanish Main Dr Unit 83, Cudjoe Key, FL 33042

Last Sold Summary
- $565/SF
- 0 Days On Market
Last Sold Price $435,000

Last Listing Agent Angelina Will Berkshire Hathaway HomeServices Knight & Gardner Realty

/74
$799,000 Pending
- 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
/71
$3,150,000 Sold Aug 28, 2025

225 Colson Dr, Summerland Key, FL 33042
- 6 Beds
- 7 Baths
- 4,976 Sq Ft
- Built 2010
Last Sold Summary
- 10% Below List Price
- $633/SF
- 118 Days On Market
Current Estimated Value $3,260,698

Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

225 Colson Dr, Summerland Key, FL 33042

/8
Est $193,746 Not Listed For Sale

1135 Hakluyt Ln, Cudjoe Key, FL 33042
1135 Hakluyt Ln, Cudjoe Key, FL 33042

Last Sold Summary
- 3% Below List Price
- 7 Days On Market
Last Sold Price $200,000

Last Listing Agent John Nazzaro Keller Williams Realty Premier Properties - Kendall

/125
$999,000
- 2 Beds
- 2 Baths
- 1,284 Sq Ft
22748 Blackbeard Ln, Cudjoe Key, FL 33042

Welcome home to this impressively spacious 2-bedroom, 2-bath Keys retreat, offering an elevated blend of comfort, functionality, and coastal living. The outdoor living space is a dream with a new concrete pool & waterfall feature, 12k lb boat lift, 60' concrete seawall, & an expansive 10 foot deep back porch (total of nearly 700 sq ft of porches), all perfect for outdoor dining, lounging, &

Lindsay Ryan

EXP Realty LLC

(786) 807-7897

22748 Blackbeard Ln, Cudjoe Key, FL 33042
/39
$912,250 Sold Apr 03, 2025

22879 Blackbeard Ln, Summerland Key, FL 33042
- 3 Beds
- 2 Baths
- 1,344 Sq Ft
- Built 2002
Last Sold Summary
- 8% Below List Price
- $679/SF
- 43 Days On Market
Current Estimated Value $928,883

Last Listing Agent Sandra Tuttle Island Welcome Real Estate

22879 Blackbeard Ln, Summerland Key, FL 33042

/47
Not Listed For Sale

701 Spanish Main Dr Unit 537, Cudjoe Key, FL 33042
- 1 Bed
- 1 Bath
- 520 Sq Ft
- Built 2000
701 Spanish Main Dr Unit 537, Cudjoe Key, FL 33042

Last Sold Summary
- $601/SF
- 194 Days On Market
Last Sold Price $312,500

Last Listing Agent Anne Press Lokation Real Estate

/39
$1,399,000
- 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 Turn-Key home captures the effortless glamour of Palm Springs design blended with the laid-back sophistication of the Florida Keys. Offered fully furnished with 3 Bedrooms and 2 Baths, the residence has been beautifully remodeled with meticulous attention to detail, honoring its

Lisa Ferringo

Coldwell Banker Schmitt Real Estate Co

(786) 551-4933

51 Drost Dr, 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
Current Estimated Value $811,981

Last Listing Agent Pamela Stangler Expert Realty LLC

22878 Privateer Dr, Summerland Key, FL 33042

/20
Est $260,167 Not Listed For Sale

701 Spanish Main Dr Unit 14, Cudjoe Key, FL 33042
- Built 2001
701 Spanish Main Dr Unit 14, Cudjoe Key, FL 33042

Last Sold Summary
- 4% Above List Price
- 167 Days On Market
Last Sold Price $250,000

Last Listing Agent Kelly Gardner Bluescape Real Estate

/43
$1,799,000
- 3 Beds
- 3 Baths
- 2,456 Sq Ft
51 Sawyer Dr, Summerland Key, FL 33042

Tucked into the sought-after waterfront enclave of Cudjoe Gardens, 51 Sawyer Drive offers the rarest of Florida Keys luxuries: ground-level living above base flood elevation. Built with integrity from solid concrete block and enhanced by Pella windows and a standing seam metal roof, this residence delivers peace of mind and timeless appeal. Boaters will appreciate the 80-foot concrete dock,

Lisa Ferringo

Coldwell Banker Schmitt Real Estate Co

(844) 970-3222

51 Sawyer 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

/27
Est $264,836 Not Listed For Sale

701 Spanish Main Dr Unit 473, Cudjoe Key, FL 33042
- 1 Bed
- Built 1974
701 Spanish Main Dr Unit 473, Cudjoe Key, FL 33042

Last Sold Summary
- 18% Above List Price
- $311/SF
- 161 Days On Market
Last Sold Price $225,000

Last Listing Agent Kelly Gardner Bluescape Real Estate

/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
/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

/16
Not Listed For Sale

8 Calico Jack Cir, Cudjoe Key, FL 33042
8 Calico Jack Cir, Cudjoe Key, FL 33042

Last Sold Summary
- 212 Days On Market
Last Sold Price $165,000

Last Listing Agent Beata Sharpe Coldwell Banker Vanguard Realty

/77
$12,999,999
- 31 Beds
- 19 Baths
21470 Overseas Hwy, Cudjoe Key, FL 33042

Located on Cudjoe Key, only 20 miles from Key West. Transient use property, over 3.5 acres, 15 units (15 ROGO exemptions), over 300 feet of water frontage, boat basin, 3 concrete docks, one wooden dock, boat ramp. Shared coin laundry, 2 swimming pools, 3 private driveways. 2 parcels on US 1 are zoned Sub Urban Commercial, excellent rental history. Property spans from US 1 to the Atlantic Ocean.

Jennifer Weeks

Select Properties of NWFL

(786) 882-8127

21470 Overseas Hwy, Cudjoe 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

/2
Not Listed For Sale

7 Calico Jack Cir, Cudjoe Key, FL 33042
7 Calico Jack Cir, Cudjoe Key, FL 33042

Last Sold Summary
Last Sold Price $200,000

Last Listing Agent Beata Sharpe Coldwell Banker Vanguard Realty

/49
$1,145,000
- 3 Beds
- 2 Baths
- 1,260 Sq Ft
22737 Blackbeard Ln, Cudjoe Key, FL 33042

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

Terry Garcia

Keller Williams Key West Compass Realty

(786) 321-8407

22737 Blackbeard Ln, 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

Showing Results 1 - 40, Page 1 of 18

Florida Monroe County Cudjoe Key

Home Trends in Cudjoe Key, FL

On average, homes in Cudjoe Key, FL sell after 81 days on the market compared to the national average of 55 days. The median sale price for homes in Cudjoe Key, FL over the last 12 months is $1,225,000, up 53% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$1,225,000

Median Single Family Sale Price

$1,262,500

Median 2 Bedroom Sale Price

$375,000

Average Price Per Sq Ft

$952

Number of Homes for Sale

Last 12 months Home Sales

Months of Supply

7.40

Median List Price

$1,336,000

Median Change From 1st List Price

Median Home Sale Price YoY Change

53%

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Cudjoe Key, FL Homes

Real Estate & Homes

Home Trends in Cudjoe Key, FL

Housing Trends