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Newest Homes for Sale in Cudjoe Key, FL

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  • 22939 Privateer Dr, Summerland Key, FL 33042
    22939 Privateer Dr, Summerland Key, FL 33042
    22939 Privateer Dr, Summerland Key, FL 33042
    /41

    $775,000

    • 3 Beds
    • 2 Baths
    • 1,288 Sq Ft

    22939 Privateer Dr, Summerland Key, FL 33042

    Welcome to your private slice of paradise in desirable Cudjoe Key. this charming well maintained 3-bedroom, 2-bath home sits on an oversized double lot, offering space, privacy, and endless Keys lifestyle potential.With 1,144 square feet of living space, the home is thoughtfully laid out and surrounded by lush tropical surroundings. The property backs up to a private wooded area, creating a

    Agent Photo

    Michelle Howerton

    Brenda Donnelly Real Estate LLC

    (833) 381-1226

    22939 Privateer Dr, Summerland Key, FL 33042
  • 20844 4th Ave W, Summerland Key, FL 33042
    20844 4th Ave W, Summerland Key, FL 33042
    20844 4th Ave W, Summerland Key, FL 33042
    /61

    $2,795,000

    • 4 Beds
    • 3 Baths
    • 2,951 Sq Ft

    20844 4th Ave W, Summerland Key, FL 33042

    FISHERMAN'S DREAM! BIG BOATS WELCOME! DEEP WATER! LARGE WATERFRONT HOME in the prestigious neighborhood of Cudjoe Gardens. When you first walk up you will notice the beautiful landscaping, tropical fruit trees, key limes, mangoes, lemons, bananas and avocados! This stunning and elegant concrete residence on elevated lot, offers the perfect harmony of luxury and comfort. All new impact windows &

    Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

    20844 4th Ave W, Summerland Key, FL 33042
  • 1083 Labat Ln, Cudjoe Key, FL 33042
    1083 Labat Ln, Cudjoe Key, FL 33042
    1083 Labat Ln, Cudjoe Key, FL 33042
    /73

    $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

    (786) 841-9203

    1083 Labat Ln, Cudjoe Key, FL 33042
  • 22978 Port Royal Ln, Summerland Key, FL 33042
    22978 Port Royal Ln, Summerland Key, FL 33042
    22978 Port Royal Ln, Summerland Key, FL 33042
    /55

    $999,000

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft

    22978 Port Royal Ln, Summerland Key, FL 33042

    Ocean side location enjoy diving , fishing, dining from your boat come home to relax on your deck watching the sunset. Open floor plan new upgrades throughout.Several pictures added with staged furnishing for you to see what rooms could look like.Extra large property with plenty of room for your R/V, boats. Your own boat launch with plenty of dockage on your concrete seawall. Beautifully

    Anne Press Lokation Real Estate

    22978 Port Royal Ln, Summerland Key, FL 33042
  • 701 Spanish Main Dr Unit 28, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 28, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 28, Cudjoe Key, FL 33042
    /32

    $349,000

    • 2 Beds
    • 1 Bath
    • 388 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
  • 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

    $150,000

    • Land
    • 0.16 Acre
    • $937,500 per Acre

    0 Bk 14 Lt 1 Vacant Land Unit B26008689, 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

    Jaysen Larrieux LoKation

    0 Bk 14 Lt 1 Vacant Land Unit B26008689, 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
    /40

    $790,000

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

    22920 Privateer Dr, Summerland Key, FL 33042

    Unlock Instant Equity on this Waterfront Gem waiting for restoration! Rare opportunity to own a waterfront escape at an unbeatable price point. This diamond in the rough is priced strictly for its condition, allowing you to build custom equity from day one. With a solid foundation and a backyard leading straight to the water's edge, this is the ultimate project for a savvy investor or visionary

    Jeff Shapiro Global Luxury Realty LLC

    22920 Privateer Dr, Summerland Key, FL 33042
  • 110 Doubloon Ln, Summerland Key, FL 33042
    110 Doubloon Ln, Summerland Key, FL 33042
    110 Doubloon Ln, Summerland Key, FL 33042
    /49

    $1,150,000

    • 2 Beds
    • 2 Baths
    • 1,260 Sq Ft

    110 Doubloon Ln, Summerland Key, FL 33042

    Welcome to island life--this charming 2-bedroom, 2-bath waterfront cottage captures everything we love about the Florida Keys. Tucked on a desirable corner lot with canals on two sides, the property offers exceptional privacy, sea breezes, and inviting views from multiple vantage points. Inside, the home is bright, fresh, and thoughtfully updated, featuring a crisp white kitchen with quartz

    Agent Photo

    Sandra Tuttle

    Island Welcome Real Estate

    (786) 957-4255

    110 Doubloon Ln, Summerland Key, FL 33042
  • 701 Spanish Main Dr Unit LOT 423, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit LOT 423, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit LOT 423, Cudjoe Key, FL 33042
    /58

    $295,000

    • 1 Bed
    • 1 Bath
    • 316 Sq Ft

    701 Spanish Main Dr Unit LOT 423, Cudjoe Key, FL 33042

    INCOME PRODUCING POWERHOUSE! Welcome to 'Conch Hideaway' #423, a proven tropical retreat and turnkey business in the premier Venture Out community. This charming 1BD/1BA home is a high-performing vacation rental that grossed $30,705 in 2025! INVESTMENT HIGHLIGHTS: Already live with rentals for 2026, this property has 27 days currently booked with $2,085.05 in gross revenue transferring to the

    Kate Baldwin Bluescape Real Estate

    701 Spanish Main Dr Unit LOT 423, 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

    $1,049,000

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

    288 Spanish Main Dr, Summerland Key, FL 33042

    Beautifully renovated canalfront home on Cudjoe Key offering the perfect blend of modern upgrades and classic Florida Keys charm. This 3-bedroom, 2-bath stilted home has been completely updated for serene, worry-free living.Inside, you'll find a beautiful kitchen with stainless steel appliances and quartz countertops, along with a comfortable living area. Step outside to enjoy spacious covered

    Richard Haskins Buy The Keys

    288 Spanish Main Dr, Summerland Key, FL 33042
  • 0 Disturbed Pine Rd Unit 619097, Cudjoe Key, FL 33042
    0 Disturbed Pine Rd Unit 619097, Cudjoe Key, FL 33042
    /2

    $275,000

    • Land

    0 Disturbed Pine Rd Unit 619097, Cudjoe Key, FL 33042

    Builders and Developers take a look at this 24 point lot that has a letter from Monroe County to be used toward building in the ROGO system. Contact Monroe County Building Department and/or the Monroe County Planning Department to verify use of this point lot. A great deal for anyone needing points to be competitive in the ROGO system.

    Pamela Stangler Expert Realty LLC

    0 Disturbed Pine Rd Unit 619097, Cudjoe Key, FL 33042
  • 22777 Jolly Roger Dr, Summerland Key, FL 33042
    22777 Jolly Roger Dr, Summerland Key, FL 33042
    22777 Jolly Roger Dr, Summerland Key, FL 33042
    /58

    $1,350,000

    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft

    22777 Jolly Roger Dr, Summerland Key, FL 33042

    Stop dreaming and start packing. This rare canal-front gem features a 2.75 assumable mortgage for qualified buyers—a game-changer in today’s market! Situated on a massive, double-fenced corner lot, this 3-bed, 2-bath home is the ultimate playground. There is enough room to park all your toys, boats, cars, and RV. Your 4-legged family members will love their own large yard. With no HOA, you even

    Olivia Poto GARRISON REALTY GROUP LLC

    22777 Jolly Roger Dr, Summerland Key, FL 33042
  • 701 Spanish Main Dr Unit LOT 317, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit LOT 317, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit LOT 317, Cudjoe Key, FL 33042
    /14

    $258,000

    • Land

    701 Spanish Main Dr Unit LOT 317, Cudjoe Key, FL 33042

    Venture Out RV Lot - Prime Location Near the StoreOpportunity to own a spacious RV lot in the highly desirable Venture Out community in Cudjoe Key. This pie-shaped lot measures approximately 65' x 67' x 63', offering generous space for your RV, outdoor living area, and parking.Conveniently located just a short distance from the community store and amenities, this lot provides easy access to

    Lisa Carter Florida Keys Realty, Inc.

    701 Spanish Main Dr Unit LOT 317, Cudjoe Key, FL 33042
  • 165 Cutlass Ln, Summerland Key, FL 33042
    165 Cutlass Ln, Summerland Key, FL 33042
    165 Cutlass Ln, Summerland Key, FL 33042
    /62

    $1,075,000

    • 4 Beds
    • 3 Baths
    • 2,448 Sq Ft

    165 Cutlass Ln, Summerland Key, FL 33042

    Discover your dream waterfront retreat in the Florida Keys. This canal-front home features 4 spacious bedrooms and 3 bathrooms with 2,448 sq. ft. of thoughtfully designed living space, perfect for accommodating family, guests, and entertaining. Enjoy expansive covered balconies on both levels, where you can relax and take in peaceful canal views and the laid-back island lifestyle. The generous

    Justyn Ewald Expert Realty LLC (HQ)

    165 Cutlass Ln, 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
  • 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

    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 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

    $519,000

    • 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 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
    /34

    $469,000

    • 1 Bed
    • 1.5 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 offers

    Bea Evelyn Citron Compass Florida, LLC

    701 Spanish Main Dr Unit 548, 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
    /49

    $2,100,000

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

    22542 Jolly Roger Dr, Summerland Key, FL 33042

    This striking 4-bedroom, 3-bathroom home is a testament to coastal architecture, blending rustic design with open, light-filled living spaces that showcase a breathtaking oceanfront setting. Situated on a double lot totaling .32 acres, the property offers an impressive 120 feet of frontage overlooking Cudjoe Bay—creating a rare and commanding presence along the shoreline.Broad covered

    Lauren Dunn Coldwell Banker Schmitt R.E.

    22542 Jolly Roger Dr, Summerland Key, FL 33042
  • 22852 Buccaneer Ln, Summerland Key, FL 33042
    22852 Buccaneer Ln, Summerland Key, FL 33042
    22852 Buccaneer Ln, Summerland Key, FL 33042
    /81

    $999,000

    • 3 Beds
    • 2 Baths
    • 1,356 Sq Ft

    22852 Buccaneer Ln, Summerland Key, FL 33042

    Experience true Keys living in this beautifully renovated waterfront home located in desirable Cudjoe Key -- just minutes from local favorites like Square Grouper, 420 Lounge, and The Morning Joint.Enjoy excellent boating access with a concrete dock and a 10,000 lb boat lift, making this property ideal for serious boaters.One of the standout features of this home is its privacy. The neighboring

    Agent Photo

    Austin Kimbler

    Expert Realty LLC (HQ)

    (645) 220-0519

    22852 Buccaneer Ln, Summerland Key, FL 33042
  • 154 Cutthroat Dr, Summerland Key, FL 33042
    154 Cutthroat Dr, Summerland Key, FL 33042
    154 Cutthroat Dr, Summerland Key, FL 33042
    /41

    $849,000

    • 2 Beds
    • 2 Baths
    • 960 Sq Ft

    154 Cutthroat Dr, Summerland Key, FL 33042

    Beautifully updated 2 bedroom, 2 bathroom home with spacious covered, screened porch overlooking the canal with access to both the Gulf of Mexico and the Atlantic Ocean in just a few minutes. With pride of ownership, this house has been upgraded and well maintained. Many upgrades include: 2024 - New fence with double gates and an entrance gate, gutters, landscaping, tile flooring, freshly painted

    Pamela Stangler Expert Realty LLC

    154 Cutthroat Dr, Summerland Key, FL 33042
  • 701 Spanish Main Dr Unit 374, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 374, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 374, Cudjoe Key, FL 33042
    /64

    $669,000

    • 2 Beds
    • 2 Baths
    • 816 Sq Ft

    701 Spanish Main Dr Unit 374, Cudjoe Key, FL 33042

    OCEANFRONT TRANSIENT RENTAL IN VENTURE OUT - CUDJOE KEYAmazing open water views of the sparkling Atlantic set the tone the moment you arrive. From this premier waterfront location, you'll enjoy sweeping vistas of the marina, lagoon, Tiki hut, and the iconic Bird Point sanctuary. Sunrise glows over endless blue water, creating a peaceful and ever-changing coastal backdrop.Positioned on a 35-foot

    Lanny Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 374, Cudjoe Key, FL 33042
  • 22739 Buccaneer Ln, Summerland Key, FL 33042
    22739 Buccaneer Ln, Summerland Key, FL 33042
    22739 Buccaneer Ln, Summerland Key, FL 33042
    /29

    $839,000

    • 2 Beds
    • 2 Baths
    • 1,120 Sq Ft

    22739 Buccaneer Ln, Summerland Key, FL 33042

    Welcome to Cudjoe Key - A prime location in the Lower Florida Keys. If you're looking for the ultimate ''Island Life'' this tropical canal-front home in sought-after Cutthroat Harbor Estates is exactly what you need. Perfectly positioned to embrace the laid-back Keys lifestyle, this property offers the ideal blend of waterfront living, privacy, and island charm. This 2 Bedroom 2 Bath home is

    Agent Photo

    Anneliese Dietrick

    Coldwell Banker Schmitt Lower Keys (KW)

    (786) 882-7259

    22739 Buccaneer Ln, Summerland Key, FL 33042
  • 701 Spanish Main Dr Unit 51, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 51, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 51, Cudjoe Key, FL 33042
    /49

    $985,000

    • 2 Beds
    • 2 Baths
    • 888 Sq Ft

    701 Spanish Main Dr Unit 51, Cudjoe Key, FL 33042

    Panoramic Ocean Views W/ Transient Rental License! This beautifully updated and well-maintained stilt home offers 2 bedrooms and 2 bathrooms, large kitchen with all the necessities, panoramic ocean views, a private 35' concrete seawall for your boat and off street parking for your vehicle. This home has an open deck overlooking the crystal clear waters and a screened deck just waiting for you to

    Kim Babenzien Expert Realty LLC (HQ)

    701 Spanish Main Dr Unit 51, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 574, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 574, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 574, Cudjoe Key, FL 33042
    /77

    $440,000

    • Land

    701 Spanish Main Dr Unit 574, Cudjoe Key, FL 33042

    Ocean View Canal Front RV Lot in Venture Out - 35' Concrete SeawallBuild, park, invest, or simply pull in and start living the Keys lifestyle. This 35' x 69' beautiful, waterfront RV lot in the private, gated community of Venture Out offers ocean views, a 35' concrete seawall, and direct boating access to both the Atlantic and backcountry waters.The lot features a concrete pad and walkway,

    Lanny Gardner Bluescape Real Estate

    701 Spanish Main Dr Unit 574, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 536, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 536, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 536, Cudjoe Key, FL 33042
    /27

    $375,000

    • 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
  • 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
    /22

    $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
  • 701 Spanish Main Dr Unit 29, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 29, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 29, Cudjoe Key, FL 33042
    /59

    $599,000 New Construction

    • 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

    (786) 613-4762

    701 Spanish Main Dr Unit 29, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 635, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 635, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 635, Cudjoe Key, FL 33042
    /52

    $410,000

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft

    701 Spanish Main Dr Unit 635, Cudjoe Key, FL 33042

    Vacation Rental Property with Transient Rentals Allowed! Welcome to the epitome of comfort and convenience in this Palm Harbor fully furnished two-bedroom, two-bath home located within the highly desirable Venture Out Community. This immaculate home is nestled around tropical landscaping with a relaxing patio out back. Step into the open concept living room and well-equipped eat-in kitchen,

    Kim Babenzien Expert Realty LLC (HQ)

    701 Spanish Main Dr Unit 635, Cudjoe Key, FL 33042
  • 20920 5th Ave W, Summerland Key, FL 33042
    20920 5th Ave W, Summerland Key, FL 33042
    20920 5th Ave W, Summerland Key, FL 33042
    /72

    $2,995,000

    • 4 Beds
    • 3 Baths
    • 2,913 Sq Ft

    20920 5th Ave W, Summerland Key, FL 33042

    Florida Keys luxury island living at its finest. Welcome to your private slice of tropical island living in coveted Cudjoe Gardens--a true boater's dream set on an oversized double canal-front lot (approx. 15,200 sq. ft.) with an impressive close to 200 feet of concrete seawall. This beautifully designed CBS home offers 4 bedrooms, 3 baths, and nearly 3,000 sq. ft. of living space, thoughtfully

    Agent Photo

    Miriam Novotny

    Compass Florida, LLC

    (786) 667-5744

    20920 5th Ave W, Summerland Key, FL 33042
  • 51 Sawyer Dr, Summerland Key, FL 33042
    51 Sawyer Dr, Summerland Key, FL 33042
    51 Sawyer Dr, Summerland Key, FL 33042
    /43

    $1,799,000

    • 3 Beds
    • 3 Baths
    • 2,456 Sq Ft

    51 Sawyer Dr, Summerland Key, FL 33042

    Tucked into the sought-after waterfront enclave of Cudjoe Gardens, 51 Sawyer Drive offers the rarest of Florida Keys luxuries: ground-level living above base flood elevation. Built with integrity from solid concrete block and enhanced by Pella windows and a standing seam metal roof, this residence delivers peace of mind and timeless appeal. Boaters will appreciate the 80-foot concrete dock,

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (844) 970-3222

    51 Sawyer Dr, Summerland 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

    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
  • 22865 Redfish Ln, Summerland Key, FL 33042
    22865 Redfish Ln, Summerland Key, FL 33042
    22865 Redfish Ln, Summerland Key, FL 33042
    /34

    $1,575,000

    • 3 Beds
    • 2 Baths
    • 1,667 Sq Ft

    22865 Redfish Ln, Summerland Key, FL 33042

    The Best Boating Access in the Lower Keys, hands down!!! The 'Island Life' awaits you in this stunning well thought out custom designed canal front property. This solid CBS home, nestled in lush tropical landscaping, features 3 bedrooms and 2 baths on an oversized 10,200 sq.ft. lot located in the tranquil setting of sought after Cudjoe Ocean Shores. This subdivision is extremely desirable due to

    Agent Photo

    Anneliese Dietrick

    Coldwell Banker Schmitt Lower Keys (KW)

    (645) 241-6029

    22865 Redfish Ln, Summerland Key, FL 33042
  • 153 Peg Leg Ln, Summerland Key, FL 33042
    153 Peg Leg Ln, Summerland Key, FL 33042
    153 Peg Leg Ln, Summerland Key, FL 33042
    /38

    $899,000

    • 3 Beds
    • 2 Baths
    • 1,203 Sq Ft

    153 Peg Leg Ln, Summerland Key, FL 33042

    Super quick ocean access and 60' of concrete dockage from this 3 Bedroom 2 Bath canal front home located just 2 canals over from open water! Plenty of room for all your toys in the oversized 2-Car Garage with overhead doors on both sides. Inside you will find an open floor plan leading out to a full-length Porch overlooking the water for morning coffee or evening cocktails with family and

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (833) 853-7147

    153 Peg Leg Ln, Summerland Key, FL 33042
  • 21250 Conch Dr, Summerland Key, FL 33042
    21250 Conch Dr, Summerland Key, FL 33042
    21250 Conch Dr, Summerland Key, FL 33042
    /50

    $1,499,000

    • 3 Beds
    • 2 Baths
    • 1,508 Sq Ft

    21250 Conch Dr, Summerland Key, FL 33042

    Discover a serene escape nestled in the heart of the Lower Florida Keys. Located in Cudjoe Cove, a boutique gated community of just nine homes, this 3-bedroom, 2-bath conch cottage offers unbeatable views and direct access to the ocean. Built of durable concrete with a standing seam metal roof and impact-rated windows, the home is designed for coastal resilience. A long tropical walkway leads you

    Agent Photo

    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (833) 614-3802

    21250 Conch Dr, Summerland Key, FL 33042
  • 701 Spanish Main Dr Unit 140, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 140, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 140, Cudjoe Key, FL 33042
    /46

    $409,000

    • 2 Beds
    • 1 Bath
    • 833 Sq Ft

    701 Spanish Main Dr Unit 140, Cudjoe Key, FL 33042

    This charming and meticulously maintained property is perfect for anyone looking to start enjoying the tropical paradise of the Florida Keys. It comes fully furnished with a cozy coastal style and features 1 bedroom, 1 bathroom, and an enclosed patio area with a pull-out bed and living area. The living room is bright and spacious, while the kitchen is open and easily accessible for entertaining

    Jan Fritz Coldwell Banker Schmitt RE Co.

    701 Spanish Main Dr Unit 140, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 21, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 21, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 21, Cudjoe Key, FL 33042
    /49

    $275,000

    • 1 Bed
    • 1 Bath
    • 690 Sq Ft

    701 Spanish Main Dr Unit 21, Cudjoe Key, FL 33042

    Welcome to your slice of Paradise in the florida Keys! This cozy one bed/one bath mobile home is located in the highly desirable Venture Out gated community on Cudjoe Key. Thoughtfully designed and fully furnished, this home comfortably sleeps four and is in move-in ready. Enjoy the bright and inviting Florida room featuring durable Hardie board siding, along with a covered tile patio outback,

    Kim Babenzien Expert Realty LLC (HQ)

    701 Spanish Main Dr Unit 21, 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
    • 1.5 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 seawall.* Community

    Agent Photo

    Ian Calderwood

    Bluescape Real Estate

    (786) 977-2397

    701 Spanish Main Dr Unit 453, Cudjoe Key, FL 33042
  • 701 Spanish Main Dr Unit 265, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 265, Cudjoe Key, FL 33042
    701 Spanish Main Dr Unit 265, Cudjoe Key, FL 33042
    /68

    $879,000

    • 2 Beds
    • 2 Baths
    • 816 Sq Ft

    701 Spanish Main Dr Unit 265, Cudjoe Key, FL 33042

    This Truly Spectacular Oceanfront Property offers the ultimate waterfront lifestyle and is a one of a kind, featuring an impressive 98' seawall. Designed to capture the best of coastal living, the property combines 72' of concrete seawall along a protected canal with 26' of direct Atlantic Ocean Frontage, delivering both tranquility and open-ocean beauty. A waterfront lovers dream, the canal side

    Kim Babenzien Expert Realty LLC (HQ)

    701 Spanish Main Dr Unit 265, 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

    Bea Evelyn Citron Compass Florida, LLC

    701 Spanish Main Dr Unit 566, 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 $2,235,681.
How many homes have sold over the last 12 months in Cudjoe Key, FL?
13 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 $1,336,000. If you put a 20% down payment of $267,200 and had a 30-year fixed mortgage with an interest rate of 6.46%, your estimated principal and interest payment would be $6,730 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $288K 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 81 days on the market compared to the national average of 55 days. The median sale price for homes in Cudjoe Key, FL over the last 12 months is $1,225,000, up 53% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$1,225,000
Median Single Family Sale Price
$1,262,500
Median 2 Bedroom Sale Price
$375,000
Average Price Per Sq Ft
$952
Number of Homes for Sale
8
Last 12 months Home Sales
13
Months of Supply
7.40
Median List Price
$1,336,000
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
53%
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