Sugarloaf, FL Homes for Sale

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  /29

  $1,375,000 Open Fri 11AM - 2PM

  • 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

  

  Sandra Tuttle

  Island Welcome Real Estate

  (786) 869-3656

  22974 Anne Bonny Ln, Summerland Key, FL 33042
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  /39

  $495,000

  • 1 Bed
  • 1 Bath
  • 754 Sq Ft

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

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

  

  Ian Calderwood

  Bluescape Real Estate

  (786) 551-4336

  701 Spanish Main Dr Unit 182, Cudjoe Key, FL 33042
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  /20

  $224,500

  • Land

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

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

  

  Ian Calderwood

  Bluescape Real Estate

  (786) 418-4615

  701 Spanish Main Dr Unit 658, Cudjoe Key, FL 33042
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  /71

  $1,395,000

  • 3 Beds
  • 3 Baths
  • 1,700 Sq Ft

  16941 Driftwood Ln, Summerland Key, FL 33042

  There are homes that check boxes, and then there are homes that speak to you the moment you step inside. This custom, meticulously crafted 3BR/3BA, 1,700 sq ft CBS masterpiece in the heart of Sugarloaf Shores is the latter, where thoughtful design, quiet elegance, and a touch of whimsy blend into a living experience that feels both luxurious and deeply personal.Set just 19 minutes from Key West,

  

  Coby Taylor

  Taylor & Assoc. RE, Inc.

  (855) 606-6133

  16941 Driftwood Ln, Summerland Key, FL 33042
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  /44

  $1,150,000

  • 3 Beds
  • 2 Baths
  • 1,467 Sq Ft

  21855 Spain Blvd, Summerland Key, FL 33042

  Just over An acre of paradise in the Florida Keys--21855 Spain Boulevard is more than a home, it's a private retreat designed for those who value both space and privacy. Rarely does a property offer this combination of land, privacy, all just moments from open water. Set on over an acre of lush, natural landscape, the residence is thoughtfully positioned to create a sense of sanctuary from the

  

  Matthew Sheehan

  Ocean Sotheby's International Realty

  (786) 882-7957

  21855 Spain Blvd, Summerland Key, FL 33042
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  /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.

  

  Terrance Sullivan

  Ocean Sotheby's International Realty

  (786) 204-2360

  755 Sawyer Dr, Summerland Key, FL 33042
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  /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

  

  Ian Calderwood

  Bluescape Real Estate

  (305) 570-4554

  701 Spanish Main Dr Unit 625, Cudjoe Key, FL 33042
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  /43

  $1,599,000

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft

  17152 Marlin Dr, Summerland Key, FL 33042

  Nestled on a very quiet street in the exclusive community Sugarloaf Shores, this beautifully remodeled CBS Pool Home offers the perfect blend of privacy, entertainment and island charm. Situated on a massive 12,700 sq. ft. lot, this property is a lush sanctuary for gardeners and boaters alike. The backyard is a true private resort, designed for the ultimate outdoor lifestyle featuring a heated

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 692-4942

  17152 Marlin Dr, Summerland Key, FL 33042
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  /44

  $1,699,000

  • 3 Beds
  • 3 Baths
  • 1,998 Sq Ft

  17094 Coral Dr, Summerland Key, FL 33042

  This beautifully appointed home is located in prestigious Sugarloaf Shores, an upscale coastal community of waterfront homes just 15 miles from the magic of Key West. As you enter the 3 Bedroom 2 Bath 2,000 sq. ft. home a massive Great Room greets you highlighted by a true chef's Kitchen offering lots of custom cabinetry, stainless appliances, 2 wine coolers and large center island for friends

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 244-7125

  17094 Coral Dr, Summerland Key, FL 33042
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  /48

  $2,299,000

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

  22542 Jolly Roger Dr, Summerland Key, FL 33042

  Welcome to coastal living in one of the most desirable neighborhoods in Cudjoe Key. This beautifully renovated 4-bedroom, 3-bath oceanfront residence sits proudly on a rare double lot, offering unmatched space, privacy, and breathtaking open-water views. Step inside to discover a bright, airy living space with stylish coastal finishes, vaulted ceilings, and walls of windows that frame the

  

  Emily Lombard

  Ocean Sotheby's International Realty

  (786) 952-5159

  22542 Jolly Roger Dr, Summerland Key, FL 33042
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  /6

  $400,000

  • Land

  21865 Spain Blvd, Summerland Key, FL 33042

  Over TWO acres of pristine land with native plants winding roads, storage sheds, and grassy areas. Natural Ponds and native wildlife greet you as you explore and walk through this expansive property. Birds, deer, turtle and natural hammock make this a one of kind spot, perfect for enjoying the untouched way the keys used to be! This offering is LAND only, Please also see home at 21855 Spain Blvd

  

  Matthew Sheehan

  Ocean Sotheby's International Realty

  (305) 614-8634

  21865 Spain Blvd, Summerland Key, FL 33042
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  /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

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (645) 300-6302

  21082 6th Ave, Summerland Key, FL 33042
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  /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

  

  Ian Calderwood

  Bluescape Real Estate

  (786) 882-1915

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

  

  Terrance Sullivan

  Ocean Sotheby's International Realty

  (786) 465-7217

  755 & 744 Sawyer Dr, Cudjoe Key, FL 33042
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  /37

  $999,000

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  22954 Buccaneer Ln, Summerland Key, FL 33042

  Welcome to 22954 Buccaneer Ln, a quintessential Florida Keys waterfront escape. Perfectly positioned on a rare corner canal lot, this property offers 191 feet of concrete dockage with quick, unobstructed access to open water--ideal for serious boaters. The exterior's inviting Keys-style cedar siding blends seamlessly with lush tropical landscaping, creating a relaxed island vibe from the moment

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (645) 230-1509

  22954 Buccaneer Ln, Summerland Key, FL 33042
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  /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

  

  Michelle Howerton

  Brenda Donnelly Real Estate LLC

  (855) 548-0123

  22892 Jolly Roger Dr, Summerland Key, FL 33042
• 

  

  /19

  $225,000

  • Land

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

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

  

  Ian Calderwood

  Bluescape Real Estate

  (786) 761-5180

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

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 952-7261

  20838 5th Ave W, Summerland Key, FL 33042
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  /60

  $524,000

  • 2 Beds
  • 1 Bath
  • 667 Sq Ft

  701 Spanish Main Dr Unit 602, Cudjoe Key, FL 33042

  Oceanfront Paradise Awaits!Unit 602 in Venture OutExperience the epitome of Florida living in this charming Two-bedroom, one-bathroom mid-rise mobile home nestled within an exclusive gated community.This beautiful canal front home with ocean views from the backyard home boasts:* Prime Canal front Location: Enjoy breathtaking ocean views and direct access to the water from your private 35 ft

  

  Ian Calderwood

  Bluescape Real Estate

  (786) 981-9841

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

  (786) 841-6970

  701 Spanish Main Dr Unit 172, Cudjoe Key, FL 33042
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  /55

  $1,500,000

  • 3 Beds
  • 2 Baths
  • 1,467 Sq Ft

  21865 Spain Blvd, Summerland Key, FL 33042

  Majestically positioned at the end of Spain Blvd, within the Prestigious Cudjoe Acres neighborhood. Discover 21855 & 21865 Spain Blvd. A Property that offers the kind of privacy that's almost impossible to find in the Florida Keys. Set on over 3 acres of land, this one-of-a-kind property is surrounded by naturally occurring native plants, mature trees, and freshwater ponds that encourage local

  

  Matthew Sheehan

  Ocean Sotheby's International Realty

  (645) 215-8837

  21865 Spain Blvd, Summerland Key, FL 33042
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  /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

  

  Sandra Tuttle

  Island Welcome Real Estate

  (786) 756-9163

  743 Pattison Dr, Summerland Key, FL 33042
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  /33

  $299,000

  • 1 Bed
  • 1 Bath
  • 690 Sq Ft

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

  Cozy 1-Bedroom 1-bathroom Mobile Home with Enchanting Florida RoomLocated inside the very desirable Venture Out Gated Community.This charming and very well kept mobile home offers a comfortable and affordable living space. Key Features:* Fully tiled.* Comfortable Bedroom: With plenty of large windows. * Fully equipped kitchen with table, chairs and a built in desk.* Full Bathroom: Includes

  

  Ian Calderwood

  Bluescape Real Estate

  (786) 550-7131

  701 Spanish Main Dr Unit 21, Cudjoe Key, FL 33042
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  /17

  $675,000

  • Land

  17215 Keystone Rd, Sugarloaf Shores, FL 33042

  Cleared canal-front lot in Sugarloaf Shores with building permit in place and first inspection not due until December 2026! Positioned on the desirable no-bridge side, this expansive 27,716 sq. ft. residential parcel is surrounded by multi-million-dollar homes and offers easy access to the open water where days are enjoyed paddling and kayaking through mangrove-line creeks or heading out to

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 957-7959

  17215 Keystone Rd, Sugarloaf Shores, FL 33042
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  /38

  $995,000

  • 3 Beds
  • 2 Baths
  • 2,080 Sq Ft

  687 & 689 Crane Blvd, Sugarloaf Key, FL 33042

  A truly special offering for those who value strength, design, and the uncommon. Built to endure, this elevated solid poured concrete home features an insulated and Gaco coated, concrete roof, concrete floors, and an open, vault-like design with soaring ceilings--bringing an airy, artsy, and industrial-chic feel to island living.Located in highly desirable Sugarloaf Key, just 20 minutes from Key

  

  Sandra Tuttle

  Island Welcome Real Estate

  (786) 807-6597

  687 & 689 Crane Blvd, Sugarloaf Key, FL 33042
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  /47

  $569,900

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  701 Spanish Main Dr Unit 510, Cudjoe Key, FL 33042

  Oceanfront Paradise Awaits!Unit 510 in Venture OutExperience the epitome of waterfront Florida 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 35 ft seawall.* Community Boat Ramp and boat washdown station.*

  

  Ian Calderwood

  Bluescape Real Estate

  (786) 686-7983

  701 Spanish Main Dr Unit 510, Cudjoe Key, FL 33042
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  /10

  $499,000

  • Land

  63 Sugarloaf Dr, Sugarloaf Shores, FL 33042

  Welcome to the lowest priced waterfront lot with an active building permit on prestigious Sugarloaf Key. This oversized 14,706 sq. ft. canal-front property features no-bridge ocean access, granting you instant entry to world-class fishing, diving, and boating. Located in the premier residential enclave of the Sugarloaf Shores, this lot includes an active building permit for a custom 2,120 sq.

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (305) 834-4054

  63 Sugarloaf Dr, Sugarloaf Shores, FL 33042
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  /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

  

  Ian Calderwood

  Bluescape Real Estate

  (844) 482-8589

  701 Spanish Main Dr Unit 333,334, Cudjoe Key, FL 33042
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  /45

  $1,599,000

  • 3 Beds
  • 2 Baths
  • 1,788 Sq Ft

  17227 Allamanda Dr, Summerland Key, FL 33042

  Welcome to your own slice of paradise in the desirable Sugarloaf Shores neighborhood of the Lower Keys! This beautifully designed 3 bedroom, 2 bath home offers 1,788 sq. ft. of inviting living space that perfectly blends comfort, quality, and the laid-back island lifestyle. Located on the no-bridge side of Sugarloaf Shores, this property provides quick water access to world-class fishing, diving,

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (855) 803-0852

  17227 Allamanda Dr, Summerland Key, FL 33042
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  /9

  $472,000

  • 2 Beds
  • 1 Bath
  • 460 Sq Ft

  6 Beach Dr, Key West, FL 33040

  Rare DOUBLE LOT on OPEN WATER with BOATING ACCESS and ROGO EXEMPT LETTER IN HAND!! This lot can be cleared providing huge wide water sunset views and the ability to add dockage with shallow boating access. Located in the Saddlebunch Keys, just 10 minutes from all of the superior dining and nightlife of Key West, Florida. Repair trailer that is on site under the 50% rule, or build your dream home

  

  Anneliese Dietrick

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 756-8747

  6 Beach Dr, Key West, FL 33040
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  /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

  

  Lisa Ferringo

  Coldwell Banker Schmitt Lower Keys (KW)

  (786) 551-4933

  51 Drost Dr, Summerland Key, FL 33042
• 

  

  /4

  $285,000

  • Land

  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

  Taylor & Assoc. RE, Inc.

  (786) 876-6382

  Unlisted Address
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  /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.

  

  Jennifer Weeks

  Select Properties of NWFL

  (786) 882-8127

  21470 Overseas Hwy, Cudjoe Key, FL 33042
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  /49

  $1,145,000

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

  22737 Blackbeard Ln, Cudjoe Key, FL 33042

  Welcome home to your coastal oasis! This stunning brand-new elevated home features three bedrooms, two bathrooms, with an open concept living room and kitchen plus a covered 10x30 porch. Additional features include impact resistance windows and doors, metal roof, Azek decking, powder coated aluminum railings, custom concrete dock (8x20) with a permitted 12,000 Ibs. boat lift with 298 sq. ft. of

  

  Terry Garcia

  Keller Williams Key West Compass Realty

  (786) 321-8407

  22737 Blackbeard Ln, 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

  

  Ian Calderwood

  Bluescape Real Estate

  (786) 613-4104

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

  

  /31

  $430,000

  • 2 Beds
  • 1 Bath
  • 415 Sq Ft

  21857 Disturbed Pine Rd, Summerland Key, FL 33042

  Acre of Privacy, your Keys cottage/bungalow in the woods. Artist retreat, man cave or maybe just because you love privacy and want an escape. Connected to the house by sidewalk and decking is a Screen porch 13 X 18 plus a storge room 9 X 12. Additionally, there are 2 carports, 3 sheds. Space in yard to park your cars, boats, RV. Property is 'Rogo Exempt' if you want to build new and create your

  Rose Dell Keller Williams Key West Compass Realty

  21857 Disturbed Pine Rd, Summerland Key, FL 33042
• 

  

  /39

  $499,000

  • 2 Beds
  • 2 Baths
  • 618 Sq Ft

  701 Spanish Main Dr Unit 411, Cudjoe Key, FL 33042

  Affordable waterfront Living in the Lower Keys! This waterfront 2-bedroom, 2-bath mobile home is located in Venture Out, a gated, resort-style community offering endless activities and true Island living at a price point rarely found on the water.Enjoy direct boating to open water, just minutes from the Atlantic and Gulf, making this a boaters dream. Located at Mile Marker 23, you're only 20

  Suzanne Moore Suzanne Moore Real Estate

  701 Spanish Main Dr Unit 411, Cudjoe 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
• 

  

  /59

  $1,569,999 New Construction

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

  142 Peg Leg Ln, Cudjoe Key, FL 33042

  Welcome to your dream coastal retreat! Perched on concrete stilts with sweeping views, 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

  Alejandro Perez Amerifirst Realty

  142 Peg Leg Ln, Cudjoe Key, FL 33042
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  /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

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