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Newest Homes for Sale in Cudjoe Key, FL

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  • 701 Spanish Main Dr Unit 643, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 643, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 643, Cudjoe Key, FL 33042
    /17

    $265,000

    • Land

    701 Spanish Main Dr Unit 643, Cudjoe Key, FL 33042

    Welcome to island living at its best! This 35'x 69' RV lot is ready for your rig with full hookups and all the perks of Venture Out--golf cart streets, 24-hour security, pool, tennis, pickleball, and a marina. Located minutes from local favorites Morning Joint, Square Grouper, and 420 Lounge, plus only 19 miles to Key West. Whether you're here for fishing, boating, or simply soaking in the Keys

    Jenifer Hirsch Bluescape Real Estate

    701 Spanish Main Dr Unit 643, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 642, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 642, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 642, Cudjoe Key, FL 33042
    /18

    $265,000

    • Land

    701 Spanish Main Dr Unit 642, Cudjoe Key, FL 33042

    Welcome to RV Lot 642, located in the gated, waterfront community of Venture Out on Cudjoe Key. This well-positioned lot offers the perfect setup for your Florida Keys getaway, seasonal stay, or investment opportunity.Enjoy all the perks of a golf-cart-friendly community with resort-style amenities, including a large saltwater pool, marina with boat ramp, pickleball and tennis courts, bocce,

    Jenifer Hirsch Bluescape Real Estate

    701 Spanish Main Dr Unit 642, Cudjoe Key, FL 33042
  • 1193 de Lussan Ln, Cudjoe Key, FL 33042
    1193 de Lussan Ln, Cudjoe Key, FL 33042
    1193 de Lussan Ln, Cudjoe Key, FL 33042
    /34

    $995,000

    • 3 Beds
    • 2 Baths
    • 1,188 Sq Ft

    1193 de Lussan Ln, Cudjoe Key, FL 33042

    Immaculate Oceanside 3 bedroom, 2 bath home in this highly sought after destination. Located on the southernmost tip of Cudjoe Key, the home comes with an ''OVERSIZED'' lot and has plenty of space for all your recreational needs. This light and bright home has an open floor plan, modern kitchen with stainless steel appliances, nice size bedrooms, well appointed master bedroom with a spacious

    Greg MacLaren Internet Realty of the Florida Keys

    1193 de Lussan Ln, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 444, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 444, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 444, Cudjoe Key, FL 33042
    /21

    $575,000

    • 2 Beds
    • 2 Baths
    • 861 Sq Ft

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

    Affordable piece of paradise! Fully furnished, 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. All new furnishings included! 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

    Mary Conklin Action Keys Realty of the Lower FL Keys LLC

    701 Spanish Main Dr Unit 444, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 396, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 396, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 396, Cudjoe Key, FL 33042
    /22

    $264,000

    • Land

    701 Spanish Main Dr Unit 396, Cudjoe Key, FL 33042

    Excellent investment opportunity in the private, gated waterfront community of Venture Out on Cudjoe Key. This 35' x 69' paved and landscaped lot is ideal for an RV, with nightly rentals permitted a rare and valuable feature in the Florida Keys.Venture Out offers strong rental demand and resort-style amenities, including a boat ramp, marina store, fuel station, and recreational facilities such as

    Mary Bryant Keller Williams Key West Compass Realty

    701 Spanish Main Dr Unit 396, Cudjoe Key, FL 33042
  • 151 Cutthroat Dr, Summerland Key, FL 33042
    151 Cutthroat Dr, Summerland Key, FL 33042
    151 Cutthroat Dr, Summerland Key, FL 33042
    /33

    $949,000

    • 2 Beds
    • 3 Baths
    • 1,140 Sq Ft

    151 Cutthroat Dr, Summerland Key, FL 33042

    Move-in ready waterfront 2-bedroom, 2.5-bath home located in desirable Cudjoe Key. The open floor plan features a spacious living and dining area complemented by an upgraded kitchen with new cabinetry, granite countertops, and modern stainless-steel appliances. The main level offers two bedrooms and 1.5 baths, while a permitted full second bath is conveniently located downstairs with easy access

    Heather Bennett Keller Williams Key West Compass Realty

    151 Cutthroat Dr, Summerland Key, FL 33042
  • 22974 Anne Bonny Ln, Summerland Key, FL 33042
    22974 Anne Bonny Ln, Summerland Key, FL 33042
    22974 Anne Bonny Ln, Summerland Key, FL 33042
    /29

    $1,375,000

    • 3 Beds
    • 2 Baths
    • 1,494 Sq Ft

    22974 Anne Bonny Ln, Summerland Key, FL 33042

    Welcome to 22974 Anne Bonny Lane in Cudjoe Key, a beautifully appointed, turn-key waterfront home designed for island living and ready for immediate enjoyment--whether as a full-time residence, second home, or income-producing vacation rental. This 3-bedroom, 2-bath coastal retreat is being offered fully furnished, with stylish furnishings purchased just two years ago, allowing a new owner to

    Agent Photo

    Sandra Tuttle

    Island Welcome Real Estate

    (786) 869-3656

    22974 Anne Bonny Ln, Summerland Key, FL 33042
  • 51 Drost Dr, Summerland Key, FL 33042
    51 Drost Dr, Summerland Key, FL 33042
    51 Drost Dr, Summerland Key, FL 33042
    /38

    $1,499,000

    • 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 home captures the effortless glamour of Palm Springs design blended with the laid-back sophistication of the Florida Keys. Offering 3 Bedrooms and 2 Baths, the residence has been beautifully remodeled with meticulous attention to detail, honoring its architectural roots while

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Lower Keys (KW)

    (786) 551-4933

    51 Drost Dr, Summerland Key, FL 33042
  • 701 Spanish Main Dr Unit 333,334, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 333,334, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 333,334, Cudjoe Key, FL 33042
    /74

    $799,000

    • 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

    Agent Photo

    Ian Calderwood

    Bluescape Real Estate

    (844) 482-8589

    701 Spanish Main Dr Unit 333,334, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042
    /33

    $278,500

    • 1 Bed
    • 1 Bath
    • 368 Sq Ft

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

    Welcome to Unit 533 in the Venture Out community on Cudjoe Key, featuring a spacious addition that provides extra living space and flexibility. The addition includes a comfortable living area and a flex room currently used as additional sleeping space, suitable for guests, a home office, or hobby area.The home is clean and well cared for, offering a functional layout appropriate for full-time

    Jenifer Hirsch Bluescape Real Estate

    701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042
  • 1145 Hakluyt Ln, Cudjoe Key, FL 33042
    1145 Hakluyt Ln, Cudjoe Key, FL 33042
    1145 Hakluyt Ln, Cudjoe Key, FL 33042
    /7

    $190,000

    • Land
    • 6,000 Acres
    • $32 per Acre

    1145 Hakluyt Ln, Cudjoe Key, FL 33042

    Discover one of Cudjoe Key’s desirable vacant parcels — a 6,000 sq ft waterfront lot offering direct access to the Lower Keys’. Located on a quiet road, this property pairs privacy with easy access to local conveniences and the laid-back lifestyle of the Lower Keys. Enjoy morning coffee with ocean breezes, evening skies, and endless outdoor living possibilities.(Information provided herein is

    Daniel Pacheco United Realty Group Inc

    1145 Hakluyt Ln, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 512, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 512, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 512, Cudjoe Key, FL 33042
    /37

    $939,000

    • 2 Beds
    • 2 Baths
    • 861 Sq Ft

    701 Spanish Main Dr Unit 512, Cudjoe Key, FL 33042

    NEW YEAR, NEW PRICE on this heavily rented PROTECTED DOCKAGE property! LOOK AT THIS VIEW! You have open water views from this impeccably maintained, fully stilted 2BR/2 BATH unit! A 43' SEAWALL with heavy duty dock posts, cleats, fish cleaning table and swim ladder add to the allure of this home perfect for the avid boater! North winds are NO PROBLEM with this protected dockage! The oversized

    Jamie Caudill Lokation Real Estate

    701 Spanish Main Dr Unit 512, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 181, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 181, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 181, Cudjoe Key, FL 33042
    /24

    $385,000

    • Land

    701 Spanish Main Dr Unit 181, Cudjoe Key, FL 33042

    The Ultimate Canal-Front RV Oasis in Venture Out at Cudjoe KeyEscape to your own slice of paradise with this prime waterfront RV lot in the sought-after, gated community of Venture Out on Cudjoe Key. This lot is built for the avid water enthusiast and provides a perfect base for exploring the best of the Lower and Middle Florida Keys.Fully Prepped RV Pad: Bring your rig and start relaxing

    Carmen Brake Waterfront Keys Realty Inc.

    701 Spanish Main Dr Unit 181, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 49, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 49, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 49, Cudjoe Key, FL 33042
    /55

    $925,000

    • 2 Beds
    • 1 Bath
    • 806 Sq Ft

    701 Spanish Main Dr Unit 49, Cudjoe Key, FL 33042

    ********Nightly Licensed Transient Rental!!!********This amazing, two bedroom / one bathroom, open water front, nightly transient rental is ready for you to enjoy both the beauty of this location and the income off the nightly rental license. The floor plan makes the open water views as its main focus. Cook the catch of the day overlooking the waters that you just caught that prized fish in. Sit

    Bobby Coe RE/MAX Keys Connection (KW)

    701 Spanish Main Dr Unit 49, Cudjoe Key, FL 33042
  • 22748 Blackbeard Ln, Cudjoe Key, FL 33042
    22748 Blackbeard Ln, Cudjoe Key, FL 33042
    22748 Blackbeard Ln, Cudjoe Key, FL 33042
    /125

    $1,190,000

    • 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

    22748 Blackbeard Ln, Cudjoe Key, FL 33042
  • 125 Colson Dr, Summerland Key, FL 33042
    125 Colson Dr, Summerland Key, FL 33042
    125 Colson Dr, Summerland Key, FL 33042
    /69

    $2,249,000 Pre-Foreclosure

    • 5 Beds
    • 3 Baths
    • 1,903 Sq Ft

    125 Colson Dr, Summerland Key, FL 33042

    THIS PROPERTY IS A ONE OF A KIND! A TRUE ''UNICORN!'' TRANSIENT LICENSE FOR NIGHTLY RENTALS ALLOWED! OPEN WATER VIEWS! ALMOST 2 ACRES TOTAL WITH 4 LOTS! 5 bedrooms and 3 baths in this charming and OLD FLORIDA KEYS STYLE PROPERTY! Privacy, lush vegetation, stunning Open water views, balconies from almost every room! Original hardwood floor, tons of character and warmth in this lovely home! Large

    Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

    125 Colson Dr, Summerland Key, FL 33042
  • 701 Spanish Main Dr Unit 97, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 97, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 97, Cudjoe Key, FL 33042
    /54

    $899,000

    • 2 Beds
    • 2 Baths
    • 640 Sq Ft

    701 Spanish Main Dr Unit 97, Cudjoe Key, FL 33042

    Luxurious Waterfront Living - Welcome to your perfect coastal oasis in the sought-after community of Venture Out! This contemporary high-rise boasts million-dollar views from every angle, including a screened patio for ultimate enjoyment. With an outside elevator providing easy access, this stunning home features a serene primary suite with stylish decor and a beautiful walk-in shower in the

    Jan Fritz Coldwell Banker Schmitt RE Co.

    701 Spanish Main Dr Unit 97, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 437, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 437, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 437, Cudjoe Key, FL 33042
    /56

    $579,900

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft

    701 Spanish Main Dr Unit 437, Cudjoe Key, FL 33042

    Introducing an exceptional waterfront investment opportunity in the heart of the Florida Keys! This beautifully remodeled waterfront home in the highly desirable gated community of Venture Out on Cudjoe Key is zoned for minimum one-day vacation rentals, making it an ideal choice for investors or those seeking a turnkey coastal retreat. Step inside and you'll immediately appreciate the home's

    Melissa Graham Bluescape Real Estate

    701 Spanish Main Dr Unit 437, Cudjoe Key, FL 33042
  • 21082 6th Ave, Summerland Key, FL 33042
    21082 6th Ave, Summerland Key, FL 33042
    21082 6th Ave, Summerland Key, FL 33042
    /16

    $999,000

    • Land

    21082 6th Ave, Summerland Key, FL 33042

    An exceptional opportunity awaits in one of the Lower Keys' most desirable neighborhoods. This oversized corner lot is ROGO exempt and comes with approved building plans already on file with Monroe County, allowing you to skip the waiting line and begin building your dream home immediately. The existing structure has been demolished, clearing the way for a seamless transition from vision to

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Lower Keys (KW)

    (645) 300-6302

    21082 6th Ave, Summerland Key, FL 33042
  • 701 Spanish Main Dr Unit 369, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 369, Cudjoe Key, FL 33042
    /2

    $495,000

    • Land

    701 Spanish Main Dr Unit 369, Cudjoe Key, FL 33042

    Rare opportunity for water front 35 ft sea wall, now vacant lot, home was removed, located in the community of Venture Out. Build your new home or install a cement slab and use the lot for your RV or rent the site to a RV user who would like to have their boats in front of their home with easy access to open water, and the marina . Beautiful views

    Debra Schoepe Berkshire Hathaway HomeServices Knight & Gardner Realty

    701 Spanish Main Dr Unit 369, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 432, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 432, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 432, Cudjoe Key, FL 33042
    /9

    $480,000

    • Land

    701 Spanish Main Dr Unit 432, Cudjoe Key, FL 33042

    Discover the ultimate escape! This highly sought-after waterfront RV lot offers everything the coastal enthusiast dreams of, combining luxury amenities with unparalleled nautical access. Located on a wide street this lot is easily accessible for larger RV's and 5th wheels. Features a newer separate concrete parking area for your vehicle and a large level concrete pad for the Rv. Comes complete

    Carmen Brake Waterfront Keys Realty Inc.

    701 Spanish Main Dr Unit 432, Cudjoe Key, FL 33042
  • 22948 Drake Ln, Summerland Key, FL 33042
    22948 Drake Ln, Summerland Key, FL 33042
    22948 Drake Ln, Summerland Key, FL 33042
    /42

    $650,000

    • Land

    22948 Drake Ln, Summerland Key, FL 33042

    Canal front-vacant lot is ROGO exempt and ready to build on. It corners Drake Lane's dead end and is second from Cudjoe Bay's open water: Views and more views. 70-foot concrete seawall with boat slip/basin and 10,000 pound boat lift make this the perfect location for boater/angler's new home. Previous house removed and lot is ready for your new vision. Electric was in place, buyer to verify FKAA

    Barbara Bowers Preferred Properties (KW)

    22948 Drake Ln, Summerland Key, FL 33042
  • 701 Spanish Main Dr Unit 247, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 247, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 247, Cudjoe Key, FL 33042
    /59

    $549,000

    • 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
  • 463 Lesrohde Dr, Ramrod Key, FL 33042
    463 Lesrohde Dr, Ramrod Key, FL 33042
    463 Lesrohde Dr, Ramrod Key, FL 33042
    /29

    $899,000

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

    463 Lesrohde Dr, Ramrod Key, FL 33042

    Don't miss the chance to own this exceptional piece of paradise--schedule a private showing today!Be the first to call this stunning, newly constructed Affinity-built home yours! Located in desirable Ramrod Key, this energy-efficient 3-bedroom, 2-bathroom residence boasts premium quality throughout. Featuring high-end fixtures, Pella impact-resistant windows and doors, and thoughtful

    Sarah Dolson Keller Williams Key West Compass Realty

    463 Lesrohde Dr, Ramrod Key, FL 33042
  • 701 Spanish Main Dr Unit 221, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 221, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 221, Cudjoe Key, FL 33042
    /39

    $995,000

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft

    701 Spanish Main Dr Unit 221, Cudjoe Key, FL 33042

    Enjoy open water views and instant boating access from this transiently licensed, turn-key retreat in Venture Out Resort, just 20 minutes from Key West. Built in 2021, this modern 2-bedroom, 2-bath oceanfront home combines sleek design with comfort and quality craftsmanship. Step inside to discover 9ft ceilings, leather-finish granite countertops, and high-end finishes throughout. The home comes

    The Spottswood Team Truman & Co. (KW)

    701 Spanish Main Dr Unit 221, Cudjoe Key, FL 33042
  • 22892 Jolly Roger Dr, Summerland Key, FL 33042
    22892 Jolly Roger Dr, Summerland Key, FL 33042
    22892 Jolly Roger Dr, Summerland Key, FL 33042
    /43

    $2,000,000

    • 3 Beds
    • 2 Baths
    • 1,767 Sq Ft

    22892 Jolly Roger Dr, Summerland Key, FL 33042

    Open water views of Cudjoe Bay and the Atlantic. Enjoy gorgeous sunsets right in front of your dock. Spacious 3BR/2B, laundy room with a ton of storage. Lush landcaping, sandy beach great for launching paddleboards & kayaks. Modular, newly built in 2020. Spacious room sizes, open floorplan & high ceilings fill this home with light and create a relaxing flow. Close to the sandbars, Looe Key reef

    Agent Photo

    Michelle Howerton

    Brenda Donnelly Real Estate LLC

    (855) 548-0123

    22892 Jolly Roger Dr, Summerland Key, FL 33042
  • 23012 Snapper Ln, Summerland Key, FL 33042
    23012 Snapper Ln, Summerland Key, FL 33042
    23012 Snapper Ln, Summerland Key, FL 33042
    /45

    $899,999

    • 3 Beds
    • 2 Baths
    • 950 Sq Ft

    23012 Snapper Ln, Summerland Key, FL 33042

    Welcome to 23012 Snapper Lane in Beautiful Cudjoe Key, FL.This Three (3) bedroom and Two (2) bathroom elevated, waterfront on a corner lot is the one you have been looking for, with a great price too!This home is built to last and has been meticulously cared for. Come bring your boat and sit back and enjoy your favorite beverage on this oversized backyard. Tons of storage for all your toys, and

    Bobby Coe RE/MAX Keys Connection (KW)

    23012 Snapper Ln, Summerland Key, FL 33042
  • 755 Sawyer Dr, Summerland Key, FL 33042
    755 Sawyer Dr, Summerland Key, FL 33042
    755 Sawyer Dr, Summerland Key, FL 33042
    /58

    $3,750,000

    • 3 Beds
    • 2 Baths
    • 1,851 Sq Ft

    755 Sawyer Dr, Summerland Key, FL 33042

    In prestigious Cudjoe Gardens, this fully renovated Keys retreat feels more like a private sanctuary than a house. The main oceanfront lot is wrapped in lush, mature landscaping -- buttonwoods in the back, banyan trees along the side, orchids everywhere, irrigation, and low-voltage lighting that makes the property glow at night. It's the kind of tropical setting people move to the Keys for.

    Agent Photo

    Terrance Sullivan

    Ocean Sotheby's International Realty

    (786) 204-2360

    755 Sawyer Dr, Summerland Key, FL 33042
  • 755 & 744 Sawyer Dr, Cudjoe Key, FL 33042
    755 & 744 Sawyer Dr, Cudjoe Key, FL 33042
    755 & 744 Sawyer Dr, Cudjoe Key, FL 33042
    /58

    $3,750,000

    • 3 Beds
    • 2 Baths
    • 1,851 Sq Ft

    755 & 744 Sawyer Dr, Cudjoe Key, FL 33042

    In prestigious Cudjoe Gardens, this fully renovated Keys retreat feels more like a private sanctuary than a house. The main oceanfront lot is wrapped in lush, mature landscaping -- buttonwoods in the back, banyan trees along the side, orchids everywhere, irrigation, and low-voltage lighting that makes the property glow at night. It's the kind of tropical setting people move to the Keys

    Agent Photo

    Terrance Sullivan

    Ocean Sotheby's International Realty

    (786) 465-7217

    755 & 744 Sawyer Dr, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 551, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 551, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 551, Cudjoe Key, FL 33042
    /19

    $465,000

    • Land

    701 Spanish Main Dr Unit 551, Cudjoe Key, FL 33042

    Prime RV lot offering a 35' concrete seawall with quick boating access and plenty of outdoor comfort. A concrete pad, dock box, and fish cleaning station make it easy to enjoy life on the water, while the natural shade keeps things cool and inviting. This active RV rental lot is ideal for investment income, retirement living, or an active Keys lifestyle. Located in the desirable, gated community

    Jenifer Hirsch Bluescape Real Estate

    701 Spanish Main Dr Unit 551, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 172, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 172, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 172, Cudjoe Key, FL 33042
    /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

    Agent Photo

    Ian Calderwood

    Bluescape Real Estate

    (786) 841-6970

    701 Spanish Main Dr Unit 172, Cudjoe Key, FL 33042
  • 20838 5th Ave W, Summerland Key, FL 33042
    20838 5th Ave W, Summerland Key, FL 33042
    20838 5th Ave W, Summerland Key, FL 33042
    /39

    $1,599,000

    • 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

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Lower Keys (KW)

    (786) 952-7261

    20838 5th Ave W, Summerland Key, FL 33042
  • 743 Pattison Dr, Summerland Key, FL 33042
    743 Pattison Dr, Summerland Key, FL 33042
    743 Pattison Dr, Summerland Key, FL 33042
    /61

    $2,150,000

    • 3 Beds
    • 2 Baths
    • 1,674 Sq Ft

    743 Pattison Dr, Summerland Key, FL 33042

    Welcome to your slice of paradise in the Florida Keys! This stunning 3-bedroom, 2-bath canal-front home in desirable Cudjoe Gardens celebrates everything we love about island life -- in shades of blue. From the moment you arrive, you'll feel the calm, coastal vibe this home radiates.Beautifully remodeled in 2021 with full permits, this residence offers an open-concept living area with soaring

    Agent Photo

    Sandra Tuttle

    Island Welcome Real Estate

    (786) 756-9163

    743 Pattison Dr, Summerland Key, FL 33042
  • 701 Spanish Main Dr Unit 384, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 384, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 384, Cudjoe Key, FL 33042
    /18

    $600,000

    • Land

    701 Spanish Main Dr Unit 384, Cudjoe Key, FL 33042

    Experience the ultimate in oceanfront living with this fantastic lot in a pristine gated community. Boasting a 53' concrete seawall and deep water access, this property is a boater's dream. The lot is RV-ready. It's also buildable, free from ROGO restrictions, and has a successful history as a vacation rental. Venture Out at Cudjoe Cay is a distinguished residential condominium community that

    The Spottswood Team Truman & Co. (KW)

    701 Spanish Main Dr Unit 384, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 183, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 183, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 183, Cudjoe Key, FL 33042
    /18

    $470,000

    • Land

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

    Welcome to Lot 183 in Venture Out, a gated waterfront community on Cudjoe Key known for its resort-style amenities and laid-back Keys lifestyle. This beautifully maintained lot features a 35' seawall for your boat, a concrete table and benches for outdoor dining, and lush landscaping on both sides for added privacy. Enjoy easy access to the marina, boat ramp, heated pool, tennis and pickleball

    Jenifer Hirsch Bluescape Real Estate

    701 Spanish Main Dr Unit 183, Cudjoe Key, FL 33042
  • 20841 8th Ave W, Cudjoe Key, FL 33042
    20841 8th Ave W, Cudjoe Key, FL 33042
    20841 8th Ave W, Cudjoe Key, FL 33042
    /29

    $1,549,000

    • 3 Beds
    • 2 Baths
    • 1,872 Sq Ft

    20841 8th Ave W, Cudjoe Key, FL 33042

    Meticulously maintained and located in the desirable boating community of Cudjoe Gardens, this nearly 1,900 sq ft home includes 90 feet of dockage, a 10,000 lb boat lift, hurricane impact windows, doors, and garage door, as well as a gorgeous pool creating your own private oasis. A boater's paradise with easy access to both ocean side and gulf side! The inside boasts 3 spacious bedrooms and an

    Collin Tingle Coldwell Banker Schmitt Lower Keys (KW)

    20841 8th Ave W, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 625, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 625, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 625, Cudjoe Key, FL 33042
    /48

    $299,000

    • 2 Beds
    • 1 Bath
    • 720 Sq Ft

    701 Spanish Main Dr Unit 625, Cudjoe Key, FL 33042

    Income-Producing Gem in Venture Out! Affordable 2BR/1BA Getaway with Resort Amenities.Discover an incredible opportunity to own a piece of the highly sought-after, gated community of Venture Out. This charming 2-bedroom, 1-bathroom home is one of the community's most affordable properties, offering a perfect blend of cozy comfort and exceptional investment potential.Ready for you to move in

    Agent Photo

    Ian Calderwood

    Bluescape Real Estate

    (305) 570-4554

    701 Spanish Main Dr Unit 625, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 154, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 154, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 154, Cudjoe Key, FL 33042
    /66

    $539,000

    • 2 Beds
    • 2 Baths
    • 836 Sq Ft

    701 Spanish Main Dr Unit 154, Cudjoe Key, FL 33042

    Coastal Paradise with Income Potential! Stunning 2BR/2BA Home Steps from the Ocean.Embrace the ultimate coastal lifestyle in this beautifully maintained 2-bedroom, 2-bathroom home, perfectly positioned directly across the street from the ocean. Wake up to serene water views and the soothing sound of the waves from your spacious, private decka"an ideal spot for your morning coffee or evening

    Agent Photo

    Ian Calderwood

    Bluescape Real Estate

    (786) 882-1915

    701 Spanish Main Dr Unit 154, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 234, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 234, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 234, Cudjoe Key, FL 33042
    /30

    $485,000

    • 2 Beds
    • 1.5 Baths
    • 604 Sq Ft

    701 Spanish Main Dr Unit 234, Cudjoe Key, FL 33042

    Beautifully updated 2-bedroom, 1.5-bath canal-front home in Venture Out, offering move-in-ready comfort and a true taste of the Keys lifestyle. Step inside this bright and inviting space featuring a sliding pocket door that allows for a private entrance, new A/C, a newly sealed roof, and nearly all new windows. The home was completely gutted and rebuilt in 2016 with 2x4 walls, full insulation,

    Jenifer Hirsch Bluescape Real Estate

    701 Spanish Main Dr Unit 234, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 30, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 30, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 30, 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

    Agent Photo

    Ian Calderwood

    Bluescape Real Estate

    (786) 613-4104

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

Showing Results 1 - 40, Page 1 of 3

Florida Monroe County Cudjoe Key

Newest Listings for Sale in Cudjoe Key, FL

Frequently Asked Questions

What is the average home price in Cudjoe Key, FL?
Homes for sale in Cudjoe Key, FL have an average home price of $1,883,636.
How many homes have sold over the last 12 months in Cudjoe Key, FL?
12 homes have sold in Cudjoe Key, FL over the last 12 months.
What are the most popular zip codes in Cudjoe Key, FL?
The most popular zip codes in Cudjoe Key, FL include 33042, 33040 and 33043.
How much do you need to make to afford a house in Cudjoe Key?
The median home price in Cudjoe Key is $1,086,500. If you put a 20% down payment of $217,300 and had a 30-year fixed mortgage with an interest rate of 6.15%, your estimated principal and interest payment would be $5,300 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $227K a year to afford the median home price in Cudjoe Key. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in Cudjoe Key, FL?
Cudjoe Key, FL has highly rated public and private schools. Some of the best schools in Cudjoe Key based on Niche Grades are Sugarloaf School and Key West High School. Browse all the schools in Cudjoe Key, FL to learn more.

Home Trends in Cudjoe Key, FL

On average, homes in Cudjoe Key, FL sell after 110 days on the market compared to the national average of 53 days. The median sale price for homes in Cudjoe Key, FL over the last 12 months is $899,000, down 37% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$899,000
Median Single Family Sale Price
$1,071,500
Average Price Per Sq Ft
$833
Number of Homes for Sale
9
Last 12 months Home Sales
12
Months of Supply
9.00
Median List Price
$1,086,500
Median Change From 1st List Price
7%
Median Home Sale Price YoY Change
-37%
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