Cudjoe Key, FL Homes for Sale with Garage

/65
$2,499,000
- 4 Beds
- 2 Baths
- 2,739 Sq Ft
21023 2nd Ave, Summerland Key, FL 33042

Experience the ultimate Florida Keys boating lifestyle at this exceptional waterfront residence in prestigious Cudjoe Gardens. Situated on a rare double lot encompassing 16,827 square feet, this CBS-built, ground-level home sits above the flood plain and offers approximately 225 feet of waterfront on two sides, deep-water dockage, and remarkably quick ocean access. Designed for comfort and

Lisa Ferringo

Coldwell Banker Schmitt Real Estate Co

21023 2nd Ave, Summerland Key, FL 33042
Explore Cudjoe Key
/61
$1,399,000

$50K PRICE DROP
- 2 Beds
- 2 Baths
- 1,372 Sq Ft
21012 6th Ave, Summerland Key, FL 33042

Island living becomes effortless at this beautifully maintained waterfront retreat in the heart of Cudjoe Gardens. Located on a deep-water canal with quick ocean access, this CBS pool home offers the rare combination of ground-level convenience while above the flood plain. From the moment you arrive the property feels inviting and relaxed. Tropical landscaping and manicured grounds create a

Lisa Ferringo

Coldwell Banker Schmitt Real Estate Co

21012 6th Ave, Summerland Key, FL 33042
/70
$2,800,000
- 4 Beds
- 3 Baths
- 3,286 Sq Ft
21640 Overseas Hwy, Summerland Key, FL 33042

SPECIAL DAILY TRANSIENT LICENSE!!!Experience one of the Lower Keys' rarest offerings at 21640 Overseas Highway,an extraordinary 1.2 acre open-water estate with panoramic ocean views, resort style amenities, and true investment upside. Opportunities like this almost never come to market from Key West to Summerland. With 3,286 sq ft per appraisal, this 4-bedroom waterfront residence delivers

Dan Serban

Key West Luxury Real Estate Inc (KW)

21640 Overseas Hwy, Summerland Key, FL 33042
/70
$3,399,000
- 3 Beds
- 3 Baths
- 3,056 Sq Ft
21090 5th Ave, Cudjoe Key, FL 33042

Welcome to a refined waterfront pool home in the highly desirable Cudjoe Gardens neighborhood, where luxury meets laid-back island living. Located on a corner canal with 235' of waterfront this home is designed with life on the water in mind. Featuring two boat lifts, 15,000 lb and 12,000 lb, providing flexibility for multiple vessels along with a 2-car Garage for additional storage for all of

Lisa Ferringo

Coldwell Banker Schmitt Real Estate Co

21090 5th Ave, Cudjoe Key, FL 33042
/43
$1,799,000
- 3 Beds
- 2.5 Baths
- 2,456 Sq Ft
51 Sawyer Dr, Cudjoe 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

51 Sawyer Dr, Cudjoe Key, FL 33042
/71
$2,795,000

Open Sun 4PM - 6PM $200K PRICE DROP
- 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

Miriam Novotny

Compass Florida, LLC

20920 5th Ave W, Summerland Key, FL 33042
/60
$2,699,999
- 4 Beds
- 2.5 Baths
- 2,452 Sq Ft
20833 4th Ave W, Cudjoe Key, FL 33042

Welcome to one of Cudjoe Gardens' most desirable waterfront addressesBuilt in 2018, 20833 4th Avenue West is an exceptional CBS waterfront estate offering 4 bedrooms, 3 bathrooms, and more than 2,400 square feet of thoughtfully designed living space. Perfectly positioned on an oversized waterfront lot, this home combines outstanding boating amenities, resort-style outdoor living, and

Diane Corliss Coldwell Banker Schmitt RE Co.

20833 4th Ave W, Cudjoe Key, FL 33042
/41
$949,000
- 3 Beds
- 2 Baths
- 1,144 Sq Ft
342 Spanish Main Dr, Summerland Key, FL 33042

Welcome to 342 Spanish Main Drive, a beautiful canal-front home in the heart of Cudjoe Key, offering the perfect combination of waterfront living, modern comfort, and laid-back Florida Keys charm. This two-story residence features 3 bedrooms and 2 full bathrooms, thoughtfully designed for both everyday living and relaxing island escapes. The bright, open interior is move-in ready and includes a

Monika Rydzak eXp Realty LLC KW Branch

342 Spanish Main Dr, Summerland Key, FL 33042
/45
$1,269,000
- 2 Beds
- 2 Baths
- 1,100 Sq Ft
116 Spanish Main Dr, Summerland Key, FL 33042

Discover your personal island sanctuary in the heart of Cudjoe Key, where every day feels like Margaritaville. This stunning 2-bedroom, 2-bathroom single-family home has been thoughtfully updated to offer the ultimate waterfront lifestyle, featuring a sleek kitchen with a central island, 2025 updated appliances and two beautifully remodeled bathrooms. The interior glows with natural light,

Tina Fingerman Beaches MLS

116 Spanish Main Dr, Summerland Key, FL 33042
/6
$1,775,000
- 4 Beds
- 4 Baths
- 1,671 Sq Ft
193 Galleon Ln, Cudjoe Key, FL 33042

Brand new waterfront in the Keys, built for you from the ground up. This is a preconstruction home in Cutthroat Harbor Estates. You buy now and it gets built for you, delivered turnkey. Picture it: your boat at the private dock on approx. 102 ft of canal seawall, a pool and jacuzzi below, coffee on the rooftop deck. Elevated 4 bed, 4 bath, outdoor kitchen, solar and efficient systems, brand new

Joaquin Merlo-Garzon CRANELUXE

193 Galleon Ln, Cudjoe Key, FL 33042
/45
$1,150,000

$100K PRICE DROP
- 2 Beds
- 2 Baths
- 1,344 Sq Ft
20868 5th Ave W, Summerland Key, FL 33042

Welcome to your cozy coastal retreat in Cudjoe Gardens in the beautiful Florida Keys! This well maintained 2bedroom, 2bath CBS home offers 1,344 sq ft of comfortable island living with thoughtful upgrades throughout. Step inside to find custom cabinetry, adding both style and functionality to the home's inviting interior. Outside is where this property truly shines, featuring a private, small man

Karen Haack Coldwell Banker Schmitt RE Co.

20868 5th Ave W, Summerland Key, FL 33042
/42
$1,299,000

$26K PRICE DROP
- 3 Beds
- 2 Baths
- 1,741 Sq Ft
21025 3rd Ave, Summerland Key, FL 33042

Experience the best of ocean-side living with no bridges to open water--a true boater's dream! This spacious 3-bedroom, 2-bath home offers 1,741 square feet of comfortable living designed for both relaxation and entertaining.A charming paver walkway welcomes you to elegant double-door entry, opening into a bright and expansive living area with soaring high ceilings. The open layout flows

Diane Corliss Coldwell Banker Schmitt RE Co.

21025 3rd Ave, Summerland Key, FL 33042
/16
$895,900

$94K PRICE DROP
- 2 Beds
- 2 Baths
- 960 Sq Ft
22961 John Avery Ln, Summerland Key, FL 33042

Reduced over 100k for a quick sale! Boater's Paradise in Cudjoe Key under 1 million!Bring your boat, jet skis, and sense of adventure! This upgraded two-story coastal retreat is designed for water lovers, featuring over 60 feet of dock space complete with shore power, plumbing, and brand-new dual jet ski davits plus a boat lift -- perfect for launching into the Florida Keys lifestyle.The

Rayden Vega Casa Miami Real Estate

22961 John Avery Ln, Summerland Key, FL 33042

Florida Monroe County

Home Prices in Cudjoe Key, FL

The median home sale price in Cudjoe Key, FL is $1,055,000, down 14% year-over-year. Homes in Cudjoe Key sell in 132 days on average, compared to the national average of 56 days.

Home Price Trends

Median Sale Price $1,055,000	Median Single Family Sale Price $1,300,000
Median 2 Bedroom Sale Price $685,000	Average Price Per Sq Ft $816
Number of Homes for Sale 11	Last 12 months Home Sales 20
Months of Supply 6.60	Median List Price $1,549,000
Median Change From 1st List Price 9%	Median Home Sale Price YoY Change -14%

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

In Cudjoe Key, there are currently 13 homes for sale with a garage. Meeting the needs of buyers seeking secure parking and extra storage, these homes offer various garage options. Whether it's a property featuring a practical two-car garage or a larger residence with a sought-after three-car garage, these homes provide the convenience and flexibility desired by many homeowners. Additionally, some properties come with detached garages, offering ample space while ensuring privacy. Explore the selection of homes for sale with a garage in Cudjoe Key, FL and find the perfect place to call home.

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