24

Cudjoe Key, FL Homes for Sale with Pool

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  • /69

    $3,300,000

    $200K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,295 Sq Ft

    1083 Labat Ln, Cudjoe Key, FL 33042

    Experience elevated island living in this striking modern residence in Cudjoe Key, where sleek design meets the raw beauty of the Atlantic. This white contemporary home showcases a dramatic wall of glass along the oceanfront, creating a seamless connection between indoor living and the endless horizon beyond. The open-concept living space is flooded with natural light and anchored by breathtaking

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    Sandra Tuttle

    Island Welcome Real Estate

    1083 Labat Ln, Cudjoe Key, FL 33042
  • /66

    $2,099,000

    • 4 Beds
    • 3.5 Baths
    • 2,548 Sq Ft

    1106 Thatch Ln, Cudjoe Key, FL 33042

    Set along a peaceful canal on Cudjoe Key, this 2016 residence pairs solid CBS construction with an unmistakably elevated sense of island living. This 4 bedroom, 3.5 bath home features impact windows and doors and a standing seam metal roof, speaking to a level of craftsmanship built to endure, while 2,548 square feet of living space and roughly 1,370 square feet of balconies invite the

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    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    1106 Thatch Ln, Cudjoe Key, FL 33042
  • /70

    $3,099,000

    $300K PRICE DROP
    • 4 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

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    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    21090 5th Ave, Cudjoe Key, FL 33042
  • /38

    $1,399,000

    $100K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,356 Sq Ft

    51 Drost Dr, Cudjoe 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

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    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    51 Drost Dr, Cudjoe Key, FL 33042
  • /65

    $2,499,000

    • 4 Beds
    • 2 Baths
    • 2,739 Sq Ft

    21023 2nd Ave, Cudjoe 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

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    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    21023 2nd Ave, Cudjoe Key, FL 33042
  • /47

    $649,000

    New Construction
    • 2 Beds
    • 2 Baths
    • 840 Sq Ft

    701 Spanish Main Dr Unit 30, Cudjoe Key, FL 33042

    Welcome to your piece of paradise in the exclusive gated community of Venture Out on Cudjoe Key. This stunning high-rise, built in 2024, embodies the perfect blend of modern luxury and island life. As you step inside, you are greeted by an inviting atmosphere that captures the essence of coastal living. The master bedroom boasts an en suite bathroom, offering a serene retreat at the end of the

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    Ian Calderwood

    Bluescape Real Estate- Venture

    701 Spanish Main Dr Unit 30, Cudjoe Key, FL 33042
  • /59

    $649,000

    New Construction $5K PRICE INCREASE
    • 2 Beds
    • 2 Baths
    • 840 Sq Ft

    701 Spanish Main Dr Unit 29, Cudjoe Key, FL 33042

    Welcome to your piece of paradise in the exclusive gated community of Venture Out on Cudjoe Key. This stunning high-rise, built in 2024, embodies the perfect blend of modern luxury and island life. As you step inside, you are greeted by an inviting atmosphere that captures the essence of coastal living. The master bedroom boasts an en suite bathroom, offering a serene retreat at the end of the

    Agent Photo

    Ian Calderwood

    Bluescape Real Estate- Venture

    701 Spanish Main Dr Unit 29, Cudjoe Key, FL 33042
  • /51

    $425,000

    • 2 Beds
    • 1 Bath
    • 748 Sq Ft

    701 Spanish Main Dr Unit 639, Cudjoe Key, FL 33042

    Enjoy the Salty Air from this Key Lime Gem in the Florida Keys! This furnished, 2 bedroom, 1 bathroom manufactured home has high ceilings that allow great entertaining from the kitchen, dining room, and living room area. Features a large master bedroom, full size bathroom with new vanity and new stackable washer/dryer, well stocked kitchen with a full line of appliances, metal roof, and tile

    Justyn Ewald Expert Realty LLC

    701 Spanish Main Dr Unit 639, Cudjoe Key, FL 33042
  • /86

    $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
  • /27

    $320,000

    $30K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 672 Sq Ft

    701 Spanish Main Dr Unit 566, Cudjoe Key, FL 33042

    Canal-front opportunity in Venture Out! This 1 bedroom / 1 bath property offers a 17' seawall and endless potential for future use. Whether you're envisioning a personal Keys retreat or re-imagining the space as an RV lot, this property provides flexibility in a highly desirable, gated waterfront community. Enjoy all Venture Out amenities including marina access, boat ramp, pools, recreational

    Jenifer Hirsch Bluescape Real Estate

    701 Spanish Main Dr Unit 566, Cudjoe Key, FL 33042
  • /47

    $445,000

    $10K PRICE DROP
    • Land
    • 2,078 Sq Ft
    • $9,328,296 per Acre

    701 Spanish Main Dr Unit LOT 496, Cudjoe Key, FL 33042

    ROGO exempt RV Lot 496 - Waterfront Lot in Venture Out, Cudjoe Key, Mile Marker 23Bring your RV or build your Florida Keys dream home without the hassle of going through the ROGO process.Waterfront RV lot located in the gated community of Venture Out on Cudjoe Key. Lot 496 has a concrete pad, offering a durable, low-maintenance surface ideal for RV parking and outdoor living.The property features

    Lanny Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit LOT 496, Cudjoe Key, FL 33042
  • /51

    $674,999

    • 2 Beds
    • 2 Baths
    • 770 Sq Ft

    701 Spanish Main Dr Unit 123, Cudjoe Key, FL 33042

    YOUR FLORIDA KEYS ESCAPE AWAITS! Welcome to your own slice of paradise in the highly sought-after gated community of Venture Out on Cudjoe Key. This beautifully furnished 2-bedroom, 2-bath home combines water views, exceptional boating access, comfortable island living, and resort-style amenities just seconds from open water.Situated on a wide 60' canal, boaters will love the 35' concrete

    Nate Bartlett Berkshire Hathaway HomeServices Keys Real Estate

    701 Spanish Main Dr Unit 123, Cudjoe 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,

    Margaret Crowley Florida Keys Realty Group

    116 Spanish Main Dr, Summerland Key, FL 33042
  • /72

    $595,000

    • 2 Beds
    • 2 Baths
    • 816 Sq Ft

    701 Spanish Main Dr Unit 604, Cudjoe Key, FL 33042

    Owner says ''Bring All Offers''Charming Coastal Retreat: 2 Bedroom, 2 Bath home with 35' concrete seawall. Nightly Rentals allowed.Welcome to your perfect getaway or investment opportunity! This delightful home built in 1993, offers 816 sq. ft. of comfortable living space, fully furnished and turn-key, making it an ideal choice for both relaxation and income generation. Step inside to discover a

    Lanny Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 604, Cudjoe Key, FL 33042
  • /49

    $749,900

    $25K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft

    19543 Navajo St, Cudjoe Key, FL 33042

    3 bed 2 bath stilt home built in 2018 in sought after Sugarloaf Key. Open concept floor plan, large kitchen with an abundance of large white cabinets, kitchen island overlooking living area, stainless steel appliances, light and stylish colors throughout. Wood-look tile plank flooring, crown molding, 9-ft ceilings, recessed lighting and ceiling fans in all bedrooms and living room. Full size

    Pamela Stangler Expert Realty LLC

    19543 Navajo St, Cudjoe 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
  • /59

    $535,000

    $14K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 860 Sq Ft

    701 Spanish Main Dr Unit 247, Cudjoe Key, FL 33042

    Oceanfront Paradise Awaits! Unit 247 in Venture Out experience the epitome of Florida living in this charming, fully furnished two-bedroom, two-bathroom mobile home nestled within an exclusive gated community. Enjoy breathtaking ocean views and direct access to the water from your private 17 ft seawall. Community amenities include a boat ramp and boat washdown station after returning from a day

    Amanda Taylor Bluescape Real Estate

    701 Spanish Main Dr Unit 247, Cudjoe Key, FL 33042
  • /55

    $329,000

    $98K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 748 Sq Ft

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

    Transient Rental Vacation Home.Welcome to your ultimate island getaway on Cudjoe Key! Step into this charming coastal oasis nestled on a spacious corner lot in the sought-after Venture Out community. This 2 bedroom, 1.5 bath retreat is the perfect blend of comfort and style that will transport you to a world of relaxation and tranquility. This income-producing home is an active vacation rental as

    Lanny Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 543, Cudjoe Key, FL 33042
  • /32

    $339,000

    $210K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 728 Sq Ft

    701 Spanish Main Dr Unit 28, Cudjoe Key, FL 33042

    Great opportunity to own an income-producing home in the gated community of Venture Out on Cudjoe Key. This 2-bedroom, 1-bath mobile home features a cozy layout with a true Florida Keys feel throughout. The property is ideally situated on a private lot with no neighbors on one side or behind, offering added privacy and tranquility. Whether you're looking for a full-time residence or a turnkey

    Melissa Graham Bluescape Real Estate

    701 Spanish Main Dr Unit 28, Cudjoe Key, FL 33042
  • /69

    $799,000

    • 2 Beds
    • 2 Baths
    • 828 Sq Ft

    701 Spanish Main Dr Unit 171, Cudjoe Key, FL 33042

    YOUR OCEAN FRONT FLORIDA KEYS ESCAPE AWAITS! Welcome to your own slice of paradise in the highly sought-after gated community of Venture Out on Cudjoe Key. This beautifully maintained 2-bedroom, 2-bath elevated home combines incredible ocean views, exceptional boating access, and resort-style living in one of the Lower Keys' most desirable waterfront communities.Step inside to soaring

    Nate Bartlett Berkshire Hathaway HomeServices Keys Real Estate

    701 Spanish Main Dr Unit 171, Cudjoe Key, FL 33042
  • /36

    $5,995,000

    $295K PRICE DROP
    • 13 Beds
    • 7 Baths
    • 5,022 Sq Ft

    21470 Overseas Hwy, Cudjoe Key, FL 33042

    Rare income-producing open-water compound on Cudjoe Key featuring 5 cottages plus a spacious main house. This gated, turnkey waterfront property offers direct open-water views, private dockage with ample boat space, on-site boat ramp, swimming pool, and lush tropical landscaping. Ideal for vacation rental income, corporate retreat, or private family compound. Each unit is well-appointed for guest

    Jennifer Weeks Select Properties of NWFL

    21470 Overseas Hwy, Cudjoe Key, FL 33042
  • /55

    $1,799,000

    New Construction
    • 3 Beds
    • 2 Baths
    • 2,050 Sq Ft

    22970 Gasparilla Ln, Cudjoe Key, FL 33042

    OPEN WATER VIEWS - BRAND NEW CUSTOM WATERFRONT HOME - DOUBLE LOT & MOVE IN READY. This ELEVATED 3 bedroom, 2 bathroom CBS home is a must see! Solid steel and concrete, standing seam white metal roof with impact windows and doors rated to 185 MPH. 2,050 total sq ft of living space includes a front porch, utility room on the lower level and a lanai off the back. A total of 1500 sq ft of living

    Joyce Craul Expert Realty LLC (HQ)

    22970 Gasparilla Ln, Cudjoe Key, FL 33042
  • /27

    $350,000

    $25K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 726 Sq Ft

    701 Spanish Main Dr Unit 536, Cudjoe Key, FL 33042

    Welcome to your slice of the Florida Keys lifestyle! This charming beach-themed retreat is the perfect blend of cozy comfort and coastal style. This 2-bedroom, 1-bathroom turnkey home is move-in ready — whether you're looking for a full-time residence, vacation getaway, or income-producing rental. Step inside to a fresh, inviting living space designed for relaxed island living. The bright white

    Monika Rydzak EXP Realty LLC

    701 Spanish Main Dr Unit 536, Cudjoe Key, FL 33042
  • /77

    $12,999,999

    $1M PRICE DROP
    • 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

    21470 Overseas Hwy, Cudjoe Key, FL 33042

Home Price Trends

Median Sale Price
$1,080,000
Median Single Family Sale Price
$1,300,000
Median 2 Bedroom Sale Price
$685,000
Average Price Per Sq Ft
$838
Number of Homes for Sale
24
Last 12 months Home Sales
19
Months of Supply
10.70
Median List Price
$1,549,000
Median Change From 1st List Price
8%
Median Home Sale Price YoY Change
20%
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