Cudjoe Key, FL Homes for Sale

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  /61

  $1,399,000

  Open Sat 11AM - 1PM $50K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,372 Sq Ft

  21012 6th Ave, Summerland Key, FL 33042

  Island living becomes effortless at this beautifully maintained waterfront retreat in the heart of Cudjoe Gardens. Located on a deep-water canal with quick ocean access, this CBS pool home offers the rare combination of ground-level convenience while above the flood plain. From the moment you arrive the property feels inviting and relaxed. Tropical landscaping and manicured grounds create a

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  21012 6th Ave, Summerland Key, FL 33042
• Explore Cudjoe Key

• 

  

  

  /65

  $2,499,000

  Open Sat 11AM - 1PM

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

  21023 2nd Ave, Summerland Key, FL 33042

  Experience the ultimate Florida Keys boating lifestyle at this exceptional waterfront residence in prestigious Cudjoe Gardens. Situated on a rare double lot encompassing 16,827 square feet, this CBS-built, ground-level home sits above the flood plain and offers approximately 225 feet of waterfront on two sides, deep-water dockage, and remarkably quick ocean access. Designed for comfort and

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  21023 2nd Ave, Summerland Key, FL 33042
• 

  

  

  /69

  $3,300,000

  $200K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,295 Sq Ft

  1083 Labat Ln, Cudjoe Key, FL 33042

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

  

  Sandra Tuttle

  Island Welcome Real Estate

  1083 Labat Ln, Cudjoe Key, FL 33042
• 

  

  

  /49

  $1,399,000

  Open Sat 11AM - 1PM $200K PRICE DROP

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

  21250 Conch Dr, Cudjoe 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

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  21250 Conch Dr, Cudjoe Key, FL 33042
• 

  

  /2

  $30,000

  $20K PRICE DROP

  • Land
  • 6,969 Sq Ft
  • $187,500 per Acre

  0 Bk 15 Lt 5 Unit 619550, Cudjoe Key, FL 33042

  Still time to submit to receive 2 points into ROGO. Tier 3 lot in Cudjoe Key for ROGO Donation use. NO Building or RV allowed on this lot. Will receive 2 points - Letter attach 2 additional lots available each for $40,000

  

  Terry Canto

  American Caribbean Real Estate, Christie's International Real Estate

  0 Bk 15 Lt 5 Unit 619550, Cudjoe Key, FL 33042
• 

  /2

  $30,000

  $20K PRICE DROP

  • Land
  • 6,969 Sq Ft
  • $187,500 per Acre

  0 Bk 15 Lt 13 Unit 619551, Cudjoe Key, FL 33042

  Still time to submit to receive 2 points into ROGO. Tier 3 lot in Cudjoe Key for ROGO Donation use. NO Building or RV allowed on this lot. Will receive 2 points - Letter attach 2 additional lots available each for $40,000

  

  Terry Canto

  American Caribbean Real Estate, Christie's International Real Estate

  0 Bk 15 Lt 13 Unit 619551, Cudjoe Key, FL 33042
• 

  

  /39

  $485,000

  $10K PRICE DROP

  • 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
• 

  

  /19

  $215,000

  • Land
  • 2,178 Sq Ft
  • $4,300,000 per Acre

  701 Spanish Main Dr Unit 610, Cudjoe Key, FL 33042

  Ocean ''peeks'' on this corner lot adds to the serenity you will get here at Lot 610 in the gated community of Venture Out on Cudjoe Key. Easy access on 2 sides of the lot.This property can do transient rentals!!As part of the Venture Out community, you'll enjoy an array of amenities at your doorstep. Dip into the massive saltwater swimming pool overlooking the ocean, or take advantage of

  

  Ian Calderwood

  Bluescape Real Estate- Venture

  701 Spanish Main Dr Unit 610, 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

  

  Ian Calderwood

  Bluescape Real Estate- Venture

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

  

  /66

  $525,000

  $14K PRICE DROP

  • 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 deck—an ideal spot for your morning coffee or evening

  

  Ian Calderwood

  Bluescape Real Estate- Venture

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

  

  /34

  $1,575,000

  $20K PRICE DROP

  • 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

  

  Anneliese Dietrick

  Coldwell Banker Schmitt RE Co.

  22865 Redfish Ln, Summerland Key, FL 33042
• 

  

  /71

  $2,795,000

  $200K PRICE DROP

  • 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

  

  Miriam Novotny

  Compass Florida, LLC

  20920 5th Ave W, Summerland Key, FL 33042
• 

  

  /70

  $2,800,000

  • 4 Beds
  • 3 Baths
  • 3,286 Sq Ft

  21640 Overseas Hwy, Summerland Key, FL 33042

  SPECIAL DAILY TRANSIENT LICENSE!!!Experience one of the Lower Keys' rarest offerings at 21640 Overseas Highway,an extraordinary 1.2 acre open-water estate with panoramic ocean views, resort style amenities, and true investment upside. Opportunities like this almost never come to market from Key West to Summerland. With 3,286 sq ft per appraisal, this 4-bedroom waterfront residence delivers

  

  Dan Serban

  Key West Luxury Real Estate Inc (KW)

  21640 Overseas Hwy, Summerland Key, FL 33042
• 

  

  /70

  $3,399,000

  • 3 Beds
  • 3 Baths
  • 3,056 Sq Ft

  21090 5th Ave, Cudjoe Key, FL 33042

  Welcome to a refined waterfront pool home in the highly desirable Cudjoe Gardens neighborhood, where luxury meets laid-back island living. Located on a corner canal with 235' of waterfront this home is designed with life on the water in mind. Featuring two boat lifts, 15,000 lb and 12,000 lb, providing flexibility for multiple vessels along with a 2-car Garage for additional storage for all of

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  21090 5th Ave, Cudjoe Key, FL 33042
• 

  

  /16

  $549,000

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  701 Spanish Main Dr Unit 424, Cudjoe Key, FL 33042

  Canal-front Paradise Awaits! Incredible view from your back deck!Unit 424 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 424, Cudjoe Key, FL 33042
• 

  

  /54

  $949,000

  $150K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 960 Sq Ft

  22953 John Silver Ln, Summerland Key, FL 33042

  Where boating lifestyle and modern coastal design align, this fully renovated 3-bedroom, 2-bathroom home in Cudjoe Key delivers exceptional waterfront living. This completely reimagined residence is ideally positioned on a premier corner canal lot, offering approximately 190 feet of concrete seawall and dockage along two waterways, an exceptional setting for boating and waterfront enjoyment.

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  22953 John Silver Ln, Summerland Key, FL 33042
• 

  

  /90

  $975,000

  $215K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,284 Sq Ft

  22748 Blackbeard Ln, Cudjoe Key, FL 33042

  Motivated Seller! Welcome home to this impressively spacious 2-bedroom, 2-bath Keys retreat, offering an elevated blend of comfort, functionality, and coastal living. The outdoor space is a dream with an in-ground concrete saltwater pool (2021) with a waterfall feature, 12k lb boat lift (2021), 60' concrete seawall, & an expansive 10' deep back porch (nearly 700 sq ft of porches), all perfect for

  

  Lindsay Ryan

  EXP Realty LLC

  22748 Blackbeard Ln, Cudjoe Key, FL 33042
• 

  

  /43

  $1,799,000

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

  51 Sawyer Dr, Cudjoe 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,

  

  Lisa Ferringo

  Coldwell Banker Schmitt Real Estate Co

  51 Sawyer Dr, Cudjoe Key, FL 33042
• 

  

  /5

  $285,000

  • Land
  • 1.01 Acres
  • $282,178 per Acre

  Unlisted Address

  Private Acre on Cudjoe Key. Lush, Tropical, and Near the Water Escape to your own secluded paradise in the Lower Keys! This just over an acre lot on Cudjoe Key is surrounded by beautiful equestrian properties and dense tropical foliage, offering unmatched privacy and tranquility. Located just seconds from a public boat ramp, you'll have easy access to world-class fishing, boating, and

  

  Coby Taylor

  Expert Realty LLC (HQ)

  Unlisted Address
• 

  

  /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

  

  Ian Calderwood

  Bluescape Real Estate- Venture

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

  

  /59

  $649,000

  New Construction $5K PRICE INCREASE

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft

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

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

  

  Ian Calderwood

  Bluescape Real Estate- Venture

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

  

  /21

  $430,000

  $35K PRICE DROP

  • 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
• 

  

  /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
• 

  

  /17

  $255,000

  $10K PRICE DROP

  • Land
  • 2,178 Sq Ft
  • $5,100,000 per Acre

  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
• 

  

  /58

  $269,000

  $26K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 316 Sq Ft

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

  $21,000+ Gross Rental Revenue so far in 2026!Welcome to Conch Hideaway #423, a charming and income-producing tropical retreat located within the highly sought-after gated community of Venture Out in the Lower Florida Keys. This 1-bedroom, 1-bath island getaway offers the perfect blend of relaxed coastal living and strong investment potential.Currently operating as a successful vacation

  Kelly Gardner Bluescape Real Estate

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

  /2

  $235,000

  $20K PRICE DROP

  • Land
  • 7.09 Acres
  • $33,145 per Acre

  Lot 7 Parcel 10, Cudjoe Key, FL 33042

  This 24 point offshore lot has been evaluated by Monroe County and is eligible for dedication back to Monroe County so you can use those 24 points to add to your ROGO points to assist in receiving a building permit through the ROGO system.

  Pamela Stangler Expert Realty LLC

  Lot 7 Parcel 10, Cudjoe Key, FL 33042
• 

  

  /24

  $259,000

  $6K PRICE DROP

  • Land
  • 2,178 Sq Ft
  • $5,180,000 per Acre

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

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

  Kelly Gardner Bluescape Real Estate

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

  

  /33

  $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

  Jenifer Hirsch Bluescape Real Estate

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

  

  /24

  $580,175

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  701 Spanish Main Dr Unit 79, Cudjoe Key, FL 33042

  Licensed Nightly Rental Property!! Discover island living at 701 Spanish Main Dr, Unit 79 in Cudjoe Key, FL. This charming property offers an unbeatable opportunity for investors or those seeking a tranquil retreat. Currently operating as a successful vacation rental, this home is perfectly positioned to generate income or serve as your own private oasis. This property promises both convenience

  Sarah Dolson Keller Williams Key West Compass Realty

  701 Spanish Main Dr Unit 79, Cudjoe Key, FL 33042
• 

  

  /51

  $425,000

  • 2 Beds
  • 1 Bath
  • 748 Sq Ft

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

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

  Justyn Ewald Expert Realty LLC

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

  

  /60

  $2,699,999

  • 4 Beds
  • 2.5 Baths
  • 2,452 Sq Ft

  20833 4th Ave W, Cudjoe Key, FL 33042

  Welcome to one of Cudjoe Gardens' most desirable waterfront addressesBuilt in 2018, 20833 4th Avenue West is an exceptional CBS waterfront estate offering 4 bedrooms, 3 bathrooms, and more than 2,400 square feet of thoughtfully designed living space. Perfectly positioned on an oversized waterfront lot, this home combines outstanding boating amenities, resort-style outdoor living, and

  Diane Corliss Coldwell Banker Schmitt RE Co.

  20833 4th Ave W, Cudjoe Key, FL 33042
• 

  

  /51

  $1,725,000

  $174K PRICE DROP

  • 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
• 

  

  /3

  $60,000

  • Land
  • 5,000 Sq Ft
  • $522,720 per Acre

  Lot 10 Rainbow Beach, Big Torch Key, FL 33042

  Tier 1 lot available for ROGO Donation use only. This property cannot be built on and no RV use is permitted. The sale includes a ROGO Dedication Letter valued at 2 points, providing a valuable advantage in the Monroe County permit allocation system.

  Shanti Cope Coldwell Banker Schmitt Key Largo

  Lot 10 Rainbow Beach, Big Torch Key, FL 33042
• 

  

  /27

  $320,000

  $30K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 672 Sq Ft

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

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

  Jenifer Hirsch Bluescape Real Estate

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

  

  /47

  $445,000

  $10K PRICE DROP

  • Land
  • 2,078 Sq Ft
  • $9,328,296 per Acre

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

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

  Lanny Gardner Bluescape Real Estate

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

  

  /19

  $430,000

  $45K PRICE DROP

  • 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
• 

  

  /13

  $450,000

  $92K PRICE DROP

  • 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
• 

  

  /60

  $799,000

  $88K PRICE DROP

  • 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 views , 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

  Bobby Coe RE/MAX Keys Connection (KW)

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

  

  /41

  $949,000

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

  342 Spanish Main Dr, Summerland Key, FL 33042

  Welcome to 342 Spanish Main Drive, a beautiful canal-front home in the heart of Cudjoe Key, offering the perfect combination of waterfront living, modern comfort, and laid-back Florida Keys charm. This two-story residence features 3 bedrooms and 2 full bathrooms, thoughtfully designed for both everyday living and relaxing island escapes. The bright, open interior is move-in ready and includes a

  Monika Rydzak eXp Realty LLC KW Branch

  342 Spanish Main Dr, Summerland Key, FL 33042
• 

  

  /61

  $639,000

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  701 Spanish Main Dr Unit 495, Cudjoe Key, FL 33042

  Spectacular peekaboo open water views abound with this updated 2 bed/2 bath canal front home with 35 foot seawall. Located in a gated community with tons of amenities. New kitchen w/Caesar quartz countertops, full backsplash, new stainless steel appliances, Koehler sink, modern, white cabinets with an abundance of storage, including a large center Island. Open concept floor plan with open water

  Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 495, Cudjoe Key, FL 33042

Showing Results 1 - 40, Page 1 of 2

Why Live in Cudjoe Key

Cudjoe Key, FL, is a small community known for its waterfront properties and unique attractions. The island, which began as a U.S. Air Force base in the late 1950s, features a mix of single-family homes and resort rentals, with much of the land remaining undeveloped. The National Key Deer Refuge, a 9,000-acre preserve, protects the endangered Key deer on the island. A notable feature is the aerostat site at the northern tip, where a large white blimp, nicknamed “Fat Albert,” hovers. Residential areas like Cutthroat Harbor Estates and Cudjoe Gardens offer stilt homes and canal-front properties, with prices ranging from $600,000 to over $3 million. The island lacks traditional parks, but residents enjoy water activities such as deep-sea diving, boating, and fishing. Bahia Honda State Park, located 15 miles away, provides additional outdoor recreation with its beach, hiking trails, and snorkeling sites. Dining options include Broil, a gourmet steakhouse, and The Bent Prop, known for its happy hour specials. For groceries, Murray’s Market is 2 miles away on Summerland Key, and a Winn-Dixie is 9 miles away on Big Pine Key. Students attend highly rated schools like Key West High School and Big Pine Academy. The Overseas Highway connects Cudjoe Key to Key West, 20 miles south, and Marathon, 30 miles north. Residents face high home and flood insurance premiums due to the island's susceptibility to hurricanes.

Learn more about living in Cudjoe Key

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 $1,725,411.

Are home prices dropping in Cudjoe Key?

Yes, home prices in Cudjoe Key are down 39% in the last 12 months.

How many homes have sold over the last 12 months in Cudjoe Key, FL?

20 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 $1,469,500. If you put a 20% down payment of $293,900 and had a 30-year fixed mortgage with an interest rate of 6.58%, your estimated principal and interest payment would be $7,490 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $321K 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 Prices in Cudjoe Key, FL

The median home sale price in Cudjoe Key, FL is $1,055,000, down 9% year-over-year. Homes in Cudjoe Key sell in 125 days on average, compared to the national average of 56 days.

Home Price Trends

Median Sale Price $1,055,000	Median Single Family Sale Price $1,300,000
Median 2 Bedroom Sale Price $685,000	Average Price Per Sq Ft $815
Number of Homes for Sale 12	Last 12 months Home Sales 20
Months of Supply 7.20	Median List Price $1,469,500
Median Change From 1st List Price 9%	Median Home Sale Price YoY Change -9%