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Waterfront Homes for Sale in Cudjoe Key, FL

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  • 22748 Blackbeard Ln, Cudjoe Key, FL 33042
    22748 Blackbeard Ln, Cudjoe Key, FL 33042
    22748 Blackbeard Ln, Cudjoe Key, FL 33042
    /125

    $999,000

    • 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, &

    Agent Photo

    Lindsay Ryan

    EXP Realty LLC

    (645) 251-6583

    22748 Blackbeard Ln, Cudjoe Key, FL 33042
  • 21470 Overseas Hwy, Cudjoe Key, FL 33042
    21470 Overseas Hwy, Cudjoe Key, FL 33042
    21470 Overseas Hwy, Cudjoe Key, FL 33042
    /77

    $12,999,999

    • 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.

    Agent Photo

    Jennifer Weeks

    Select Properties of NWFL

    (786) 882-8127

    21470 Overseas Hwy, Cudjoe Key, FL 33042
  • 1083 Labat Ln, Cudjoe Key, FL 33042
    1083 Labat Ln, Cudjoe Key, FL 33042
    1083 Labat Ln, Cudjoe Key, FL 33042
    /69

    $3,500,000

    • 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

    Agent Photo

    Sandra Tuttle

    Island Welcome Real Estate

    (645) 233-0155

    1083 Labat Ln, Cudjoe Key, FL 33042
  • 270 E Caribbean Dr, Summerland Key, FL 33042
    270 E Caribbean Dr, Summerland Key, FL 33042
    270 E Caribbean Dr, Summerland Key, FL 33042
    /67

    $3,200,000 New Construction

    • 4 Beds
    • 4 Baths
    • 2,375 Sq Ft

    270 E Caribbean Dr, Summerland Key, FL 33042

    Set against a spectacular open water backdrop with unforgettable sunset views modern, waterfront home was designed for both luxury living and serious boating. Built in 2022 with an exceptional design, the residence features solid concrete construction, polished concrete floors, impact-rated windows and doors, and a strong elevated build that delivers peace of mind in the Florida Keys

    Agent Photo

    Sandra Tuttle

    Island Welcome Real Estate

    (645) 233-1469

    270 E Caribbean Dr, Summerland Key, FL 33042
  • 701 Spanish Main Dr Unit 455, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 455, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 455, Cudjoe Key, FL 33042
    /21

    $465,000

    • 1 Bed
    • 1 Bath
    • 799 Sq Ft

    701 Spanish Main Dr Unit 455, Cudjoe Key, FL 33042

    A place to live, winter or Airbnb. Daily rentals allowed. Waterfront view down the canal. 17 ft seawall. Covered back patio for grilling or lounging. Front covered balcony. and back covered patio deck with mini sink, mini fridge & mini freezer. 1993' Manufactured home with Florida Room totaling 799 sq. ft. approx. 1 Bedroom w/a bonus room. Updated Bathroom with walk in shower, glass doors, hand

    Rose Dell Keller Williams Key West Compass Realty

    701 Spanish Main Dr Unit 455, Cudjoe 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
    /51

    $1,899,000

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

    22542 Jolly Roger Dr, Summerland Key, FL 33042

    Stunning oceanfront home. This 4-bedroom, 3-bathroom home is a testament to coastal architecture. Broad, covered balconies, generous outdoor spaces, and a private boat launch capitalize on Keys waterfront living. Large impact glass doors and windows frame ocean views and invite natural light into every room. Soaring, 26' ceilings enhance the open-concept layout with rich wood beams amplifying the

    Lauren Dunn Coldwell Banker Schmitt Islamorada

    22542 Jolly Roger Dr, Summerland Key, FL 33042
  • 22939 Gasparilla Ln, Summerland Key, FL 33042
    22939 Gasparilla Ln, Summerland Key, FL 33042
    22939 Gasparilla Ln, Summerland Key, FL 33042
    /48

    $1,499,000

    • 3 Beds
    • 2 Baths
    • 1,434 Sq Ft

    22939 Gasparilla Ln, Summerland Key, FL 33042

    Welcome to your ROOFTOP RETREAT - a beautifully remodeled waterfront home at 22939 Gasparilla Lane in Cudjoe Key, where panoramic ocean views and relaxed Keys elegance come together in perfect harmony. From the spectacular rooftop deck to the light-filled interior, shimmering turquoise water creates a breathtaking backdrop throughout the home. This thoughtfully updated 3-bedroom, 2-bath concrete

    Donna Pezzi Keller Williams Key West Compass Realty

    22939 Gasparilla Ln, Summerland Key, FL 33042
  • 20868 5th Ave W, Summerland Key, FL 33042
    20868 5th Ave W, Summerland Key, FL 33042
    20868 5th Ave W, Summerland Key, FL 33042
    /45

    $1,250,000

    • 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
  • 1163 de Lussan Ln, Summerland Key, FL 33042
    1163 de Lussan Ln, Summerland Key, FL 33042
    1163 de Lussan Ln, Summerland Key, FL 33042
    /55

    $1,650,000

    • 2 Beds
    • 2 Baths
    • 1,344 Sq Ft

    1163 de Lussan Ln, Summerland Key, FL 33042

    Are you dreaming of your own personal paradise? Look no further than this stunning property in the highly sought after Cutthroat Harbor Estates. With features that check off every box on your list, this home is truly a gem. Enjoy the luxury of CBS construction and a spacious 9000 sq. ft. lot. The 65' dock has been newly resurfaced with composite decking and comes equipped with a 10k lb boat lift

    Jan Fritz Coldwell Banker Schmitt RE Co.

    1163 de Lussan Ln, 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
    /78

    $1,490,000 New Construction

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

    142 Peg Leg Ln, Cudjoe Key, FL 33042

    Welcome to your dream coastal retreat! 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 style. Canal with direct access to the open ocean. No

    Jose Cabrera AmeriFirst Realty

    142 Peg Leg Ln, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 182, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 182, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 182, Cudjoe Key, FL 33042
    /39

    $485,000

    • 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.*

    Ian Calderwood Bluescape Real Estate- Venture

    701 Spanish Main Dr Unit 182, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 548, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 548, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 548, Cudjoe Key, FL 33042
    /33

    $469,000

    • 1 Bed
    • 2 Baths
    • 735 Sq Ft

    701 Spanish Main Dr Unit 548, Cudjoe Key, FL 33042

    Welcome to your opportunity in the gated waterfront community of Venture Out! This 1 bedroom, 1.5 bath property offers 35 feet of concrete seawall and direct canal access -- making it a true gem for boating enthusiasts and water lovers alike.Whether you're an investor searching for your next income-producing property or a creative buyer ready to design your own slice of paradise, this home

    Jenifer Hirsch Bluescape Real Estate

    701 Spanish Main Dr Unit 548, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 566, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 566, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 566, Cudjoe Key, FL 33042
    /27

    $350,000

    • 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
  • 701 Spanish Main Dr Unit LOT 496, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit LOT 496, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit LOT 496, Cudjoe Key, FL 33042
    /47

    $445,000

    • 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
  • 701 Spanish Main Dr Unit 453, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 453, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 453, Cudjoe Key, FL 33042
    /71

    $525,000

    • 2 Beds
    • 2 Baths
    • 816 Sq Ft

    701 Spanish Main Dr Unit 453, Cudjoe Key, FL 33042

    Canal-front Paradise Awaits! Incredible view from your back deck!Unit 453 in Venture Out.Experience the epitome of waterfront Florida Keys living in this charming two-bedroom, two-bathroom mid-rise mobile home nestled within an exclusive gated community.This beautiful canal front home boasts:* Prime Canal front Location: Enjoy direct access to the water from your private 17 ft

    Ian Calderwood Bluescape Real Estate- Venture

    701 Spanish Main Dr Unit 453, Cudjoe Key, FL 33042
  • 0 Bk 14 Lt 1 Vacant Land Unit B26008689, Cudjoe Key, FL 33042
    0 Bk 14 Lt 1 Vacant Land Unit B26008689, Cudjoe Key, FL 33042
    /2

    $59,000

    • Land
    • 6,969 Sq Ft
    • $368,750 per Acre

    0 Bk 14 Lt 1 Vacant Land Unit B26008689, Cudjoe Key, FL 33042

    **PROPERTY DESCRIPTION** Oceanfront vacant lot in Cudjoe Key, FL (Block 14, Lot 1). Buildable residential parcel located in a platted subdivision, offering open water views and excellent investment potential. No ROGO permit currently in place; buyer must obtain allocation prior to building. Conveniently located near Key West with access to boating, fishing, and diving. Great opportunity to own

    Jaysen Larrieux LoKation

    0 Bk 14 Lt 1 Vacant Land Unit B26008689, 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

    $430,000

    • Land
    • 2,078 Sq Ft
    • $9,013,859 per Acre

    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

    Lanny Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 551, Cudjoe Key, FL 33042
  • 1147 Basque Ln, Cudjoe Key, FL 33042
    1147 Basque Ln, Cudjoe Key, FL 33042
    1147 Basque Ln, Cudjoe Key, FL 33042
    /13

    $450,000

    • Land
    • 6,969 Sq Ft
    • $2,812,500 per Acre

    1147 Basque Ln, Cudjoe Key, FL 33042

    BUILDING & DOCK PERMITS IN HAND for this Buildable Vacant Lot! This proposed engineered house is a large 2,132 Sq Ft 2 story plus 1,066 w/ potential parking & storage below at ground level. Current design and engineering calls for 4 Bedrooms 3.5 Baths with 4 Exterior Balcony/Decks providing approximately 450 Sq Ft of additional space for Open Water Views plus the house will also have Open Water

    Brad Baker Key to the Keys Real Estate, Inc

    1147 Basque Ln, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 246, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 246, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 246, Cudjoe Key, FL 33042
    /21

    $459,000

    • 1 Bed
    • 1 Bath
    • 668 Sq Ft

    701 Spanish Main Dr Unit 246, Cudjoe Key, FL 33042

    Ocean-View Retreat in Gated Waterfront Community on Cudjoe Key!NIGHTLY RENTALS ALLOWEDWelcome to your slice of paradise in the heart of the Florida Keys. This well-maintained 1-bedroom, 1-bathroom waterfront home is located inside the highly desirable, gated community of Venture Out, offering ocean views, direct boating access, and a plethora of amenities just steps away.The home features

    Lanny Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 246, Cudjoe Key, FL 33042
  • 288 Spanish Main Dr, Summerland Key, FL 33042
    288 Spanish Main Dr, Summerland Key, FL 33042
    288 Spanish Main Dr, Summerland Key, FL 33042
    /38

    $965,000

    • 3 Beds
    • 2 Baths
    • 1,144 Sq Ft

    288 Spanish Main Dr, Summerland Key, FL 33042

    PRICE REDUCED!! - UPDATED CANALFRONT HOME WITH 60' OF DOCKAGE Don't miss this exceptional opportunity to own a beautifully upgraded canalfront home in Cudjoe Key, offering 60 feet of seawall dockage and effortless access to the open water. This fully renovated 3-bedroom, 2-bath stilted home combines modern finishes with laid-back Florida Keys style, creating the ideal setting for full-time

    Richard Haskins Buy The Keys

    288 Spanish Main Dr, Summerland Key, FL 33042
  • 701 Spanish Main Dr Unit 604, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 604, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 604, Cudjoe 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
  • 22920 Privateer Dr, Summerland Key, FL 33042
    22920 Privateer Dr, Summerland Key, FL 33042
    22920 Privateer Dr, Summerland Key, FL 33042
    /48

    $590,000

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

    22920 Privateer Dr, Summerland Key, FL 33042

    Following a monumental $200,000 price drop, this rare waterfront opportunity is available at an unbeatable price point. Launch your boat from your backyard for world-class access to the Atlantic Ocean and Gulf of Mexico. Unlock instant equity with virtual additions in the photos and below-market pricing; there is significant room to secure this property way below market value after completing

    Jeff Shapiro Global Luxury Realty LLC

    22920 Privateer Dr, Summerland Key, FL 33042
  • 701 Spanish Main Dr Unit 417, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 417, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 417, Cudjoe Key, FL 33042
    /45

    $515,000

    • 2 Beds
    • 2 Baths
    • 758 Sq Ft

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

    MOTIVATED SELLER! Turn-key 2BR/2BA waterfront fully furnished home with 35' concrete dock and patio furniture included, Front door paver patio, impact slider doors and windows, gas stove, and ample storage including outdoor dock box. Enjoy direct, deep-water access to the Ocean & Gulf, perfect for boating, fishing, and breathtaking sunrises & sunsets. Located in Venture Out, a gated, golf

    Amanda Taylor Bluescape Real Estate

    701 Spanish Main Dr Unit 417, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 84, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 84, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 84, Cudjoe Key, FL 33042
    /12

    $495,000

    • Land
    • 2,078 Sq Ft
    • $10,376,420 per Acre

    701 Spanish Main Dr Unit 84, Cudjoe Key, FL 33042

    Rare opportunity to own a transient (1-day minimum) rental RV lot in the Lower Keys. Located in a quiet, well-kept community, this buildable lot is perfect for your RV or for building a custom Keys getaway HomeThe property includes a 35-foot concrete seawall, dock posts, fishing cleaning station, swim ladder, Brand new concrete slab and full hookups with water, sewer, and 30, 50, and 110-amp

    Anay Ramos Miami New Realty

    701 Spanish Main Dr Unit 84, 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
    /36

    $859,000

    • 2 Beds
    • 2 Baths
    • 861 Sq Ft

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

    VACATION RENTAL OPPORTUNITY - OPEN WATER VIEWS + 43' DOCK - 2BR/2BA | 864 SQ. FT. Beautifully maintained 2-bedroom, 2-bath waterfront home offering open water views and excellent rental potential. This 864 sq. ft. property features a 43-foot dock with quick access to world-class boating, fishing, and diving in the Florida Keys. Ideal for investors or owners seeking a turn-key vacation rental

    Jamie Caudill Island Breeze Realty, LLC

    701 Spanish Main Dr Unit 512, 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 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

    $535,000

    • 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
  • 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

    $445,000

    • Land
    • 2,178 Sq Ft
    • $8,900,000 per Acre

    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
  • 701 Spanish Main Dr Unit 602, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 602, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 602, Cudjoe Key, FL 33042
    /60

    $487,500

    • 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

    Ian Calderwood Bluescape Real Estate- Venture

    701 Spanish Main Dr Unit 602, 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

    Ian Calderwood Bluescape Real Estate- Venture

    701 Spanish Main Dr Unit 172, Cudjoe Key, FL 33042
  • 22961 John Avery Ln, Summerland Key, FL 33042
    22961 John Avery Ln, Summerland Key, FL 33042
    22961 John Avery Ln, Summerland Key, FL 33042
    /16

    $989,999

    • 2 Beds
    • 2 Baths
    • 960 Sq Ft

    22961 John Avery Ln, Summerland Key, FL 33042

    Boater's Paradise in Cudjoe Key under 1 million! Priced to Sell! Bring all offers!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
  • 701 Spanish Main Dr Unit 47, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 47, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 47, Cudjoe Key, FL 33042
    /75

    $915,000

    • 2 Beds
    • 2 Baths
    • 816 Sq Ft

    701 Spanish Main Dr Unit 47, Cudjoe Key, FL 33042

    This is the house for your boat!ENDLESS OCEANFRONT LIVING - 47' SEAWALLWake up every morning to sweeping sunrises & unobstructed views of the turquoise Atlantic at this extraordinary one-of-a-kind, oceanfront residence. The 'Crown Jewel of the Ocean' located just 19 miles from Key West, this beautifully appointed 2-bedroom, 2-bath mid-rise home offers front-row seats to the water & an unmatched

    Lanny Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 47, 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
  • 701 Spanish Main Dr Unit 342, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 342, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 342, Cudjoe Key, FL 33042
    /30

    $430,000

    • 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

    Lanny Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 342, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 659, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 659, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 659, Cudjoe Key, FL 33042
    /46

    $487,000

    • 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
  • 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 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
    /11

    $480,000

    • Land
    • 1,920 Sq Ft
    • $10,890,000 per Acre

    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
  • 22552 Jolly Roger Dr, Cudjoe Key, FL 33042
    22552 Jolly Roger Dr, Cudjoe Key, FL 33042
    22552 Jolly Roger Dr, Cudjoe Key, FL 33042
    /6

    $499,000

    • Land
    • 6,969 Sq Ft
    • $3,118,750 per Acre

    22552 Jolly Roger Dr, Cudjoe Key, FL 33042

    Oceanfront lot in the Lower Keys overlooking Cudjoe Bay. Build your dream with expansive open-water views and ocean breezes. Prime waterfront setting with incredible potential. No current building permit; buyer to verify process and timelines. Rare opportunity to own a slice of paradise.

    Lauren Dunn Coldwell Banker Schmitt Islamorada

    22552 Jolly Roger Dr, Cudjoe Key, FL 33042
Florida Monroe County Cudjoe Key

Real Estate & Homes for Sale in Cudjoe Key, FL

Home Trends in Cudjoe Key, FL

On average, homes in Cudjoe Key, FL sell after 74 days on the market compared to the national average of 57 days. The median sale price for homes in Cudjoe Key, FL over the last 12 months is $1,225,000, up 13% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$1,225,000
Median Single Family Sale Price
$1,300,000
Median 2 Bedroom Sale Price
$375,000
Average Price Per Sq Ft
$815
Number of Homes for Sale
11
Last 12 months Home Sales
15
Months of Supply
8.80
Median List Price
$1,377,000
Median Change From 1st List Price
6%
Median Home Sale Price YoY Change
13%
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