5

Homes for Sale in Cudjoe Key, FL with 4-Bedrooms

Section Image Section Image
  • 20920 5th Ave W, Summerland Key, FL 33042
    20920 5th Ave W, Summerland Key, FL 33042
    20920 5th Ave W, Summerland Key, FL 33042
    /72

    $2,995,000

    • 4 Beds
    • 3 Baths
    • 2,913 Sq Ft

    20920 5th Ave W, Summerland Key, FL 33042

    Florida Keys luxury island living at its finest. Welcome to your private slice of tropical island living in coveted Cudjoe Gardens--a true boater's dream set on an oversized double canal-front lot (approx. 15,200 sq. ft.) with an impressive close to 200 feet of concrete seawall. This beautifully designed CBS home offers 4 bedrooms, 3 baths, and nearly 3,000 sq. ft. of living space, thoughtfully

    Agent Photo

    Miriam Novotny

    Compass Florida, LLC

    (786) 667-5744

    20920 5th Ave W, Summerland Key, FL 33042
  • 20844 4th Ave W, Summerland Key, FL 33042
    20844 4th Ave W, Summerland Key, FL 33042
    20844 4th Ave W, Summerland Key, FL 33042
    /61

    $2,795,000

    • 4 Beds
    • 3 Baths
    • 2,951 Sq Ft

    20844 4th Ave W, Summerland Key, FL 33042

    FISHERMAN'S DREAM! BIG BOATS WELCOME! DEEP WATER! LARGE WATERFRONT HOME in the prestigious neighborhood of Cudjoe Gardens. When you first walk up you will notice the beautiful landscaping, tropical fruit trees, key limes, mangoes, lemons, bananas and avocados! This stunning and elegant concrete residence on elevated lot, offers the perfect harmony of luxury and comfort. All new impact windows &

    Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

    20844 4th Ave W, Summerland Key, FL 33042
  • 165 Cutlass Ln, Summerland Key, FL 33042
    165 Cutlass Ln, Summerland Key, FL 33042
    165 Cutlass Ln, Summerland Key, FL 33042
    /62

    $1,075,000

    • 4 Beds
    • 3 Baths
    • 2,448 Sq Ft

    165 Cutlass Ln, Summerland Key, FL 33042

    Discover your dream waterfront retreat in the Florida Keys. This canal-front home features 4 spacious bedrooms and 3 bathrooms with 2,448 sq. ft. of thoughtfully designed living space, perfect for accommodating family, guests, and entertaining. Enjoy expansive covered balconies on both levels, where you can relax and take in peaceful canal views and the laid-back island lifestyle. The generous

    Justyn Ewald Expert Realty LLC (HQ)

    165 Cutlass Ln, Summerland Key, FL 33042
  • 22542 Jolly Roger Dr, Summerland Key, FL 33042
    22542 Jolly Roger Dr, Summerland Key, FL 33042
    22542 Jolly Roger Dr, Summerland Key, FL 33042
    /49

    $2,100,000

    • 4 Beds
    • 3 Baths
    • 2,440 Sq Ft

    22542 Jolly Roger Dr, Summerland Key, FL 33042

    This striking 4-bedroom, 3-bathroom home is a testament to coastal architecture, blending rustic design with open, light-filled living spaces that showcase a breathtaking oceanfront setting. Situated on a double lot totaling .32 acres, the property offers an impressive 120 feet of frontage overlooking Cudjoe Bay—creating a rare and commanding presence along the shoreline.Broad covered

    Lauren Dunn Coldwell Banker Schmitt R.E.

    22542 Jolly Roger Dr, Summerland Key, FL 33042
  • 142 Peg Leg Ln, Cudjoe Key, FL 33042
    142 Peg Leg Ln, Cudjoe Key, FL 33042
    142 Peg Leg Ln, Cudjoe Key, FL 33042
    /59

    $1,529,999 Open Sat 11AM - 2PM

    • 4 Beds
    • 3 Baths
    • 2,136 Sq Ft

    142 Peg Leg Ln, Cudjoe Key, FL 33042

    Welcome to your dream coastal retreat! Perched on concrete stilts with sweeping views, this newer 4-bedroom, 3-bath luxury home offers the perfect blend of island elegance and modern comfort. Two spacious master suites provide privacy and flexibility, while the open-concept living space is framed by wide, breezy balconies -- ideal for soaking in the sunrise or entertaining guests in true Keys

    Alejandro Perez Amerifirst Realty

    142 Peg Leg Ln, Cudjoe Key, FL 33042
Florida Monroe County Cudjoe Key

4-Bedroom Homes for Sale in Cudjoe Key, FL

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
8
Last 12 months Home Sales
13
Months of Supply
7.40
Median List Price
$1,336,000
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
53%
How to Buy a Home How to Finance a Home How to Sell a Home

Explore a variety of 4-bedroom homes for sale in Cudjoe Key, where there are currently 5 listings available. These properties offer spacious and accommodating living spaces suitable for larger families or those in need of extra room. With versatility and flexibility, there's ample space for bedrooms, home offices, or recreational areas. Whether you're in search of a modern townhouse, a charming single-family home, or a luxurious estate, there are options to match your preferences and lifestyle needs. Explore the selection of 4-bedroom homes for sale in Cudjoe Key, FL and find the perfect residence to accommodate your needs.

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

Copyright © 2026 CoStar Group