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Cudjoe Key, FL Homes for Sale with Pool

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  • /36

    $795,000

    • 2 Beds
    • 1 Bath
    • 864 Sq Ft

    701 Spanish Main Dr Unit 77, Cudjoe Key, FL 33042

    This canal-front, slice of paradise is an excellent income-generating opportunity in the gated community of Venture Out. As a successful, active vacation rental where nightly rentals are allowed, it's tastefully furnished, turnkey and ready for you or your guests to enjoy. With all the amenities this 69-acre gated community offers, you might just decide to make it your primary home in the Lower

    Agent Photo

    Patti Nickless

    Coldwell Banker Schmitt RE Co. Lower Keys Office

    (645) 205-1034

    701 Spanish Main Dr Unit 77, Cudjoe Key, FL 33042
  • /44

    $997,000

    • 2 Beds
    • 2 Baths
    • 779 Sq Ft

    701 Spanish Main Dr Unit 214, Cudjoe Key, FL 33042

    Welcome to your own piece of paradise in the heart of Cudjoe Key located in the gated community of Venture Out, where the island breeze and good vibes never stop!Live the island life in this turnkey 2 Bedroom, 2 Bath open water gem that's fully furnished and ready to rock your flip-flops off! Kick back on the oversized covered porch upstairs and catch the cool ocean vibes - it's your front-row

    Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 214, Cudjoe Key, FL 33042
  • /56

    $305,000

    • 1 Bed
    • 1 Bath
    • 368 Sq Ft

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

    Welcome to this well-maintained home located in the desirable all-age community of Venture Out on Cudjoe Key. This home offers more than meets the eye, featuring a spacious addition that includes a carpeted living area and a versatile flex room currently used as an extra sleeping space--ideal for guests or a home office.While the exterior is modest, the inside offers a comfortable, well-kept

    Kimberly Didrichsons Bluescape Real Estate

    701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042
  • /60

    $539,000

    • 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

    701 Spanish Main Dr Unit 602, Cudjoe Key, FL 33042
  • /114

    $1,500,000 Open Sat 12PM - 2PM

    • 3 Beds
    • 2 Baths
    • 1,560 Sq Ft

    153 Galleon Ln, Summerland Key, FL 33042

    Open House Saturday June 14th from 12-2 PM! Welcome home to this beautifully maintained waterfront retreat in the heart of the Florida Keys! Located on the highly sought-after Cudjoe Key, this spacious & elegant home blends casual island living with refined comfort, all custom-designed & cared for with exceptional pride & attention to detail.From the moment you arrive, you'll notice the peaceful,

    Lindsay Ryan EXP Realty LLC

    153 Galleon Ln, Summerland Key, FL 33042
  • /23

    $3,500,000

    • 4 Beds
    • 4.5 Baths
    • 3,228 Sq Ft

    22815 Port Royal Ln, Summerland Key, FL 33042

    DIRECT OCEAN FRONT - BOATERS PARADISE FOUND with room for 3 Boats on unobstructed sunset view over open water - oversized corner lot with water on 2 sides at end of a private road offering picture perfect sunsets in a protected bay! Boasting 323' of water frontage, includes 175' of open water and 148' of canal frontage featuring a 90' concrete dock, and a private kayak launch. The main level of

    Rhonda Gailey Gailey Enterprises Real Estate

    22815 Port Royal Ln, Summerland Key, FL 33042
  • /19

    $649,000

    • 2 Beds
    • 2 Baths
    • 816 Sq Ft

    701 Spanish Main Dr Unit 466, Cudjoe Key, FL 33042

    Open Water Views! Deep Water Boating with a 35' dock! Licensed Transient Rental Property! Expansive water views looking down a very wide Y-shaped canal to open water! A 35' concrete seawall, perfect for the serious fisherman and diver, features a sprawling concrete deck, set up with fish cleaning table, dock posts and swim ladder for all the conveniences! Bring your boat, kayak and/or paddle

    701 Spanish Main Dr Unit 466, 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

    701 Spanish Main Dr Unit 610, Cudjoe Key, FL 33042
  • /49

    $1,290,000

    • 2 Beds
    • 2 Baths
    • 1,248 Sq Ft

    701 Spanish Main Dr Unit 587, Cudjoe Key, FL 33042

    Welcome to your piece of paradise! This stunning high-rise is the largest square footage home in the exclusive gated community of Venture Out on Cudjoe Key. This property 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

    Ian Calderwood Bluescape Real Estate

    701 Spanish Main Dr Unit 587, Cudjoe Key, FL 33042
  • /55

    $407,000

    • 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

    Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 543, Cudjoe Key, FL 33042
  • /44

    $2,850,000

    • 2 Beds
    • 2 Baths
    • 1,577 Sq Ft

    1176 Thatch Ln, Summerland Key, FL 33042

    Unobstructed Ocean views, you will love this Private Oasis! Enjoy the Cudjoe Key lifestyle in this fabulous 2 bedroom, 2 bath home. Built in 1984 with a well-planned 1577 sqft floorplan, perfectly situated on a corner, oceanfront 24,829 sqft lot. This beautiful home will sell fast!! Granite kitchen countertops, brand new stainless steel appliances, new AC, new tankless water heater, impact doors

    Jonathan Minerick Homecoin.com

    1176 Thatch Ln, Summerland Key, FL 33042
  • /20

    $229,999

    • Land

    701 Spanish Main Dr Unit 658, Cudjoe Key, FL 33042

    RV Lot 658 is located in the exclusive gated community of Venture Out. Oceanfront Paradise Awaits!Experience the epitome of Florida living in beautiful Cudjoe Key, located right in between Key West and Marathon. * Community Boat Ramp and boat washdown station.* Community Amenities: Indulge in a resort-style lifestyle with access to a huge heated pool, spa, clubhouse, pickleball courts, tennis

    Ian Calderwood Bluescape Real Estate

    701 Spanish Main Dr Unit 658, Cudjoe Key, FL 33042
  • /61

    $637,000

    • 2 Beds
    • 2 Baths
    • 816 Sq Ft

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

    Charming Coastal Retreat: 2 Bedroom, 2 Bath home with concrete seawall and investment potential.Welcome to your perfect getaway or investment opportunity! This delightful two-bedroom, two-bathroom 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 cozy and

    Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 604, Cudjoe Key, FL 33042
  • /34

    $359,000

    • Land

    701 Spanish Main Dr Unit 355, Cudjoe Key, FL 33042

    Oversized RV lot with nice open water views down the 60' wide canal with enjoyable tropical breezes. A 17' stepdown concrete seawall with cleats is perfect for your boating needs. Easy access to both the gulf and ocean. Impeccable lot with concrete pad, tropical landscaping, picnic table & electric hookup with 30 & 50 amp. Venture Out has extensive amenities including 80' heated pool, spa, tennis

    Jan Fritz Coldwell Banker Schmitt RE Co. Lower Keys Office

    701 Spanish Main Dr Unit 355, Cudjoe Key, FL 33042
  • /29

    $504,000

    • Land

    701 Spanish Main Dr Unit 240, Cudjoe Key, FL 33042

    BUILDABLE Waterfront RV Lot with Transient 1 day Rental Opportunity!! This RV site is perfect for your needs. Can accommodate a large RV, easy when parking and has room for storage shed and the rights to build a home in the future. The lot it is located in a private street, providing privacy and enjoyment. 24 hour Gated Security entry. Located near Key West (19 Miles) this property is perfect

    Howard & Lily Leitner Robert Slack LLC

    701 Spanish Main Dr Unit 240, Cudjoe Key, FL 33042
  • /51

    $459,000

    • 1 Bed
    • 1 Bath
    • 816 Sq Ft

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

    Charming Opportunity in Venture Out on Cudjoe Key! Welcome to your next project in the sought-after gated community of Venture Out! This one-bedroom, one-bath mobile home is brimming with potential, offering a unique chance for investors or DIY enthusiasts looking to create their dream getaway. As you step inside, you'll find a cozy layout that provides a blank canvas for your creative vision.

    Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 280, Cudjoe Key, FL 33042
  • /30

    $470,000

    • 1 Bed
    • 1 Bath
    • 748 Sq Ft

    701 Spanish Main Dr Unit 342, Cudjoe Key, FL 33042

    Welcome to your tropical paradise at Venture Out, a gated community on Cudjoe Key, located at Mile Marker 23 in the stunning Florida Keys! This charming, fully furnished 1-bedroom, 1-bath retreat is perfect for enjoying the sun-drenched lifestyle you've been dreaming of. Step into your cozy getaway, featuring a spacious 35' concrete seawall that invites you to explore the waters. Unwind on the

    Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 342, Cudjoe Key, FL 33042
  • /39

    $495,000

    • 1 Bed
    • 1 Bath
    • 754 Sq Ft

    701 Spanish Main Dr Unit 182, Cudjoe Key, FL 33042

    Oceanfront Paradise Awaits!Unit 182 in Venture OutExperience the epitome of Florida living in this charming one-bedroom, one-bathroom mobile home with Florida Room nestled within an exclusive gated community.This beautifully maintained home boasts:* Prime Canal front Location: Enjoy breathtaking ocean views and direct access to the water from your private 35 ft seawall.* Community Boat Ramp and

    Ian Calderwood Bluescape Real Estate

    701 Spanish Main Dr Unit 182, Cudjoe Key, FL 33042
  • /33

    $345,000

    • 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

    701 Spanish Main Dr Unit 21, Cudjoe Key, FL 33042
  • /24

    $475,000

    • Land

    701 Spanish Main Dr Unit 600, Cudjoe Key, FL 33042

    Welcome to your own slice of paradise at Venture Out, a premier gated community in the heart of the Florida Keys, located at Mile Marker 23 on Cudjoe Key. This exceptional RV lot, measuring 35' x 69', offers the perfect blend of comfort and functionality for the ultimate outdoor lifestyle. Features of this lot include a sturdy concrete seawall equipped with a convenient fish cleaning table and

    Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 600, Cudjoe Key, FL 33042
  • /26

    $268,000

    • 2 Beds
    • 1 Bath
    • 664 Sq Ft

    701 Spanish Main Dr Unit 457, Cudjoe Key, FL 33042

    2 bedroom 1 bath mobile home located at 701 Spanish Main Dr Lot #457 Cudjoe Key FL in Venture Out, an individually owned residential condominium community with 24hr gated security located 20 miles from world famous Key West. This mobile home is on a non-waterfront lot w/ a peek-a-boo view of eastern facing canal. Other ideal use as a ROGO exempt buildable lot for a new elevated home. No age

    Deirdre Praught Florida Keys Realty, Inc.

    701 Spanish Main Dr Unit 457, Cudjoe Key, FL 33042
  • /34

    $1,380,000 Open Sat 10AM - 12PM

    • 3 Beds
    • 2 Baths
    • 2,100 Sq Ft

    22822 John Silver Ln, Summerland Key, FL 33042

    Nestled in the serene and sought-after community of Cudjoe Key, this stunning Glen Gray Build two-story home offers the perfect blend of comfort, luxury, and coastal living. With three spacious bedrooms and two beautifully appointed bathrooms, this home is designed for both relaxation and entertaining, featuring exceptional outdoor spaces, waterfront access, and breathtaking ocean views.Key

    Karen Haack Coldwell Banker Schmitt RE Co. Lower Keys Office

    22822 John Silver Ln, Summerland Key, FL 33042
  • /30

    $849,900

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft

    701 Spanish Main Dr Unit 468, Cudjoe Key, FL 33042

    Dream Island Living Awaits!Discover this move-in ready, fully furnished 2 bed/2bath canal front home in the secure gated community of Venture Out in CUDJOE KEY. This beautifully appointed property features a 35 ft concrete seawall, perfect for boaters and water enthusiasts, offering stunning open water views that create a serene backdrop for your island lifestyle. Enjoy ample downstairs space,

    Katrina Vanek Bluescape Real Estate

    701 Spanish Main Dr Unit 468, Cudjoe Key, FL 33042
  • /46

    $539,000

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft

    701 Spanish Main Dr Unit 659, Cudjoe Key, FL 33042

    Seller is motivated!Coastal Charm Meets Modern Comfort -Welcome to your ideal island escape in the heart of the Lower Keys! This beautifully furnished two-bedroom, two-bath stilt home is located in the welcoming gated residential community of Venture Out on Cudjoe Key--a neighborhood that embraces coastal living and a strong sense of community for all ages.Inside, you'll find a bright and airy

    Lanny Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 659, Cudjoe Key, FL 33042
  • /47

    $425,000

    • 2 Beds
    • 1.5 Baths
    • 675 Sq Ft

    701 Spanish Main Dr Unit 414, Cudjoe Key, FL 33042

    Welcome to a slice of paradise tucked away in the gated community of Venture Out on Cudjoe Key, where your dream of coastal living becomes a reality. This charming 2-bedroom, 1.5-bathroom home invites you to embrace the tropical lifestyle, offering the perfect blend of comfort and tranquility. The interior of this cozy residence is thoughtfully furnished, ensuring you can start enjoying your new

    Melissa Graham Bluescape Real Estate

    701 Spanish Main Dr Unit 414, Cudjoe Key, FL 33042
  • /19

    $299,900

    • Land

    701 Spanish Main Dr Unit 236, Cudjoe Key, FL 33042

    Lush landscape on this corner lot adds to the privacy you will get her at Lot 236 in the gated community of Venture Out on Cudjoe Key. Located on a beautiful boating canal, this lot has a 13.25' concrete seawall. The lot has a separate seating area nestled under the shade of the palm trees.Looking to build in the future? This lot is ROGO exempt. Build your high rise home and capture the open

    Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 236, Cudjoe Key, FL 33042
  • /55

    $899,000

    • 2 Beds
    • 2 Baths
    • 640 Sq Ft

    701 Spanish Main Dr Unit 97, 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 2018, 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

    Melissa Graham Bluescape Real Estate

    701 Spanish Main Dr Unit 97, Cudjoe Key, FL 33042
  • /20

    $489,000

    • Land

    701 Spanish Main Dr Unit 183, Cudjoe Key, FL 33042

    New Listing! This 35' x 69' canal front lot has ocean views and excellent boating. Bring your RV and live simply by the sea in the private, gated community of Venture Out on Cudjoe Key. Are you looking to build without having to go through the ROGO process? Look no further! This Lot provides you the Right to Build your future home.This Lot has a concrete parking pad and lush tropical landscaping

    Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 183, Cudjoe Key, FL 33042
  • /32

    $477,000

    • 2 Beds
    • 2 Baths
    • 814 Sq Ft

    701 Spanish Main Dr Unit 22, Cudjoe Key, FL 33042

    Charming Florida Keys Retreat at Venture Out on Cudjoe Key: Your Slice of Paradise Awaits! Welcome to your dream getaway nestled in the vibrant Venture Out community! This beautifully designed 2 BR, 2 BA home, built in 2016, is perfect for those seeking a blend of relaxation and adventure. Fully furnished and ready for you to move in or rent out nightly, this property is a true gem in the heart

    Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 22, Cudjoe Key, FL 33042
  • /33

    $645,000

    • 2 Beds
    • 2 Baths
    • 861 Sq Ft

    701 Spanish Main Dr Unit 444, Cudjoe Key, FL 33042

    Affordable piece of paradise! Move in ready, open concept, bright and airy, and freshly painted interior! This 2 bedroom 2 bath home is so spacious you'll be amazed. It has a very large kitchen and living area that looks out over the canal, with sliding glass doors out on to the newly painted deck. Minisplits in each room that cool, heat and dehumidify! Plus, a 5 stage reverse osmosis water

    Mary Conklin Action Keys Realty FL Keys Inc

    701 Spanish Main Dr Unit 444, Cudjoe Key, FL 33042
  • /24

    $265,000

    • Land

    701 Spanish Main Dr Unit 69, Cudjoe Key, FL 33042

    RV Lot or Build your home here in the private, gated community of Venture Out on Cudjoe Key. 35' x 69' paved and cleared lot. Nightly rentals allowed here! Many amenities on-site including a boat ramp, marina store and fuel station. Basketball, bocce, tennis and pickleball courts. Heated saltwater swimming pool right by the ocean. Venture Out is a golf cart friendly community. There are always

    Kelly Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 69, Cudjoe Key, FL 33042
  • /71

    $562,000

    • 2 Beds
    • 2 Baths
    • 758 Sq Ft

    701 Spanish Main Dr Unit 417, Cudjoe Key, FL 33042

    NEW PRICE! Motivated seller so bring your offer! Turn-key, updated 2/2 with 35' of DOCK & WATERFRONT is ready to generate a lucrative income with nightly rentals allowed. The furniture is included! BRAND NEW PAVER PATIO! This amenity-rich, gated community is perfect for investors or seasonal/full-time residents! DON'T MISS YOUR OPPORTUNITY IN THIS HIGHLY SOUGHT-AFTER PIECE OF PARADISE! Direct,

    Laurie Keiling Engel & Volkers Marathon

    701 Spanish Main Dr Unit 417, Cudjoe Key, FL 33042
  • /77

    $13,995,000

    • 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
  • /32

    $1,399,000 New Construction

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft

    22872 Buccaneer Ln, Cudjoe Key, FL 33042

    Embrace the ultimate Keys lifestyle in this spacious 1,500 sqft home, ideally situated along a boating canal in the Lower Florida Keys, and close to Key West!Tucked away in a quiet, peaceful neighborhood.Inside, the home features generous living space, providing ample room to stretch out and make it your own. Indoor-outdoor living is at its best here, with a private swimming pool just steps from

    Nick Boumerhi Meyer and Boumerhi Realty LLC

    22872 Buccaneer Ln, Cudjoe Key, FL 33042

Home Trends in Cudjoe Key, FL

Housing Trends

Median Sale Price
$1,375,000
Median Single Family Sale Price
$1,535,000
Median 2 Bedroom Sale Price
$795,000
Average Price Per Sq Ft
$947
Number of Homes for Sale
13
Last 12 months Home Sales
27
Months of Supply
5.80
Median List Price
$1,599,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
13%
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