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Explore Similar Homes Within 2 Miles of Craig Key, FL

  • /49

    $1,675,000 Open Sat 11AM - 1PM

    • 3 Beds
    • 3 Baths
    • 2,034 Sq Ft

    159 Iroquois Dr, Islamorada, FL 33036

    Discover island living at its finest in this beautifully remodeled 3-bedroom, 3-bath ''Florida Modern'' CBS home, ideally located in the desirable Lower Matecumbe Beach neighborhood of Islamorada.A light-filled open-concept layout seamlessly connects the living, dining, and kitchen areas--perfect for entertaining or relaxed island living. The home features three spacious bedrooms and three full

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    Pierre Bellion

    Ocean Sotheby's International Realty

    (645) 600-8447

    159 Iroquois Dr, Islamorada, FL 33036
  • /89

    $4,997,000

    • 5 Beds
    • 7 Baths
    • 3,597 Sq Ft

    113 Court Contessa, Islamorada, FL 33036

    Introducing one of the most exceptional homes ever offered in prestigious Port Antigua! Casa Contessa is a 2023 modern coastal estate built by the seller for the seller, with every feature intentionally selected to be top-tier. This 5BR/6.5BA, 3,597 sq ft residence is engineered to perfection with full CBS construction, impact windows/doors, and a true concrete roof.Tucked on a quiet cul-de-sac,

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    Coby Taylor

    Taylor & Assoc. RE, Inc.

    (645) 238-6287

    113 Court Contessa, Islamorada, FL 33036
  • /35

    $450,000

    • 5 Beds
    • 4 Baths
    • 2,907 Sq Ft

    134 Nautilus Dr, Islamorada, FL 33036

    New co-ownership opportunity: Own one-eighth of this professionally managed, turnkey home by Pacaso. Tucked within the coveted White Marlin Beach enclave, this canal-front retreat captures the essence of refined Florida Keys living. Framed by swaying palms and a gracious front entry, the 5-bedroom, 3.5-bathroom residence offers a seamless blend of comfort and coastal elegance.The open-concept

    Joseph Maehler Pacaso Inc.

    134 Nautilus Dr, Islamorada, FL 33036
  • /65

    $2,999,000

    • 3 Beds
    • 3 Baths
    • 1,830 Sq Ft

    101 Madeira Ct, Islamorada, FL 33036

    Welcome to your coastal retreat in the highly sought-after Port Antigua neighborhood--where relaxed Keys living meets exceptional boating access and resort-style amenities. Residents enjoy a private homeowner's beach and boat ramp, enhancing the ease of life on the water. This solid CBS construction home offers approximately 75 feet of dockage, a 12,000 lb boat lift, and a convenient fish

    Alina Davis Coldwell Banker Schmitt Islamorada

    101 Madeira Ct, Islamorada, FL 33036
  • /34

    $975,000

    • 4 Beds
    • 3 Baths
    • 1,710 Sq Ft

    100 Iroquois Dr Unit 5, Islamorada, FL 33036

    This fully furnished waterfront townhome offers 36 feet of dockage and a beautifully renovated interior designed for effortless Keys living. Thoughtfully updated and tastefully decorated, the home is move-in ready and ideal for full time living or weekend getaway. The layout is exceptionally well-suited for multigenerational living or hosting family and friends, with two bedrooms and two

    Nancy Hershoff Coldwell Banker Schmitt Islamorada

    100 Iroquois Dr Unit 5, Islamorada, FL 33036
  • /92

    $6,500,000

    • 3 Beds
    • 3 Baths
    • 2,684 Sq Ft

    158 Sapodilla Dr, Islamorada, FL 33036

    The prettiest, most perfect Keys home you ever did see. Discover one of the most beautifully updated homes in the Florida Keys, set on two spacious lots on Sapodilla Drive. This exceptional property has been completely reimagined with high-quality upgrades throughout, including a brand-new metal roof, a stunning pool and spa, and a private dock with boat lift offering protected dockage and

    The Florida Keys Sold Sisters Ocean Sotheby's International Realty

    158 Sapodilla Dr, Islamorada, FL 33036
  • /57

    $3,350,000

    • 4 Beds
    • 3.5 Baths
    • 3,182 Sq Ft

    145 Venetian Dr, Islamorada, FL 33036

    TURN KEY Canal-Front Islamorada Home with Pool, Dock & Private Beach AccessLuxury canal-front home in Islamorada offering spacious living, refined coastal design, and exceptional outdoor amenities. This meticulously maintained residence features a flexible split floor plan with a main-level living area, wet bar, bedroom, and full bath overlooking the outdoor kitchen and resort-style pool.Upstairs

    Kelsey Caputo Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

    145 Venetian Dr, Islamorada, FL 33036
  • /33

    $1,100,000

    • 3 Beds
    • 2.5 Baths

    101 Gulfview Dr Unit 116, Islamorada, FL 33036

    This beautifully maintained 3-bedroom, 2.5-bath condo offers the perfect blend of comfort, style, and resort-level amenities, all within a gated, private setting in Lower Matecumbe. Step inside to an inviting open-concept layout featuring high ceilings, abundant natural light, and a generous living and dining area ideal for relaxing or entertaining. The well-appointed kitchen includes ample

    Judy Rossignol Paradise Florida Keys Real Est

    101 Gulfview Dr Unit 116, Islamorada, FL 33036
  • /14

    $2,250,000

    • Land

    129 Porto Vista Ct, Islamorada, FL 33036

    BPAS AWARD LETTER IN HAND. PERMIT READY FOR PICK UP! BUILD RIGHT AWAY. 150 FT CONCRETE DOCK AND SEAWALL. Welcome to Port Antigua, this highly coveted neighborhood is know for its beautiful sandy beach, wide crystal-clear canals, and deep-water dockage.129 Porto Vista Ct is located on a quiet cul-de-sac. This oversized 8,436 sq ft lot provides space, privacy, and exceptional dockage! Quick Ocean

    Jessica Pinder

    129 Porto Vista Ct, Islamorada, FL 33036
  • /36

    $2,200,000

    • 3 Beds
    • 2 Baths
    • 1,228 Sq Ft

    121 Lisbon Ct, Islamorada, FL 33036

    What does everyone dream of? The smallest house in the best neighborhood -- and this one delivers. Welcome to easy, breezy living in Port Antigua, where charm, quality, and location come together beautifully.This thoughtfully updated home is being offered fully furnished -- from stylish pieces down to kitchen wares, dishes, and linens -- making your transition to the Keys seamless. Just bring

    Alina Davis Coldwell Banker Schmitt Islamorada

    121 Lisbon Ct, Islamorada, FL 33036
  • /39

    $3,524,000

    • 7 Beds
    • 4 Baths
    • 3,524 Sq Ft

    110 Gulfview Dr, Islamorada, FL 33036

    A Keys compound built to enjoy now-grow into the future, or internally convert to a 3,524 sq ft primary home without structural changes, while retaining a Waterfront Transferable Development Right (TDR/TBR) in Islamorada (approx. $650K value).Exceptional opportunity in the coveted White Marlin Beach community at MM74, this canal-front luxury family compound offers rare multi-family autonomy,

    Karen Jenkins EXP Realty, LLC

    110 Gulfview Dr, Islamorada, FL 33036
  • /37

    $3,100,000

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

    114 Sunset Dr, Islamorada, FL 33036

    Artfully updated canal-front pool home on beloved Sunset Drive with deeded access to one of the prettiest beaches in the area! This delightful residence was recently remodeled from top to bottom by a local and renowned builder and features a bright open floor plan, modern kitchen with stainless steel appliances, and coastal-inspired finishes throughout. Bonus pre-firm 1BA/1BA downstairs. The

    The Florida Keys Sold Sisters Ocean Sotheby's International Realty

    114 Sunset Dr, Islamorada, FL 33036
  • /81

    $6,490,000

    • 5 Beds
    • 5.5 Baths
    • 5,456 Sq Ft

    137 Sapodilla Dr, Islamorada, FL 33036

    Big, beautiful, and exceptionally solid, this waterfront Islamorada residence is perfectly situated on Sandy Cove Basin with protected deep-water dockage for multiple boats and direct bay access. A gated, pavered double driveway leads to an inviting foyer where marble floors and a private elevator welcome you.The elevated living level features a spacious great room with fireplace and coral

    Leslie Leopold Ocean Sotheby's International Realty

    137 Sapodilla Dr, Islamorada, FL 33036
  • /102

    $10,900,000

    • 6 Beds
    • 4.5 Baths
    • 4,394 Sq Ft

    186 & 165 Bayview Dr, Lower Matecumbe, FL 33036

    A refined expression of waterfront living, this six-bedroom, four-bath residence is set on a desirable over 1/2 acre lot with panoramic water views from every room. Offering 220+ linear feet of concrete dockage with three boat lifts, the property is exceptionally suited for large vessels with effortless access to the open Florida Bay/Gulf or Ocean via Channel 5 bridge. Two separate parcels

    The Florida Keys Sold Sisters Ocean Sotheby's International Realty

    186 & 165 Bayview Dr, Lower Matecumbe, FL 33036
  • /44

    $935,000

    • 2 Beds
    • 1.5 Baths
    • 1,322 Sq Ft

    109 Costa Bravo Dr, Islamorada, FL 33036

    Rare offering at Sandy Point Condo in Port Antigua! Enjoy the best of both worlds - beachfront living & protected dockage for your boat. Enter through the ground level & up the stairs to the main living area, where you'll find water views from your living space, an expansive galley kitchen with upgraded Fisher Paykel appliances & dining room, and a convenient half bathroom. The second set of

    Courtney Conley Serhant Florida LLC - Coconut Grove

    109 Costa Bravo Dr, Islamorada, FL 33036
  • /69

    $4,695,000

    • 3 Beds
    • 3 Baths
    • 1,973 Sq Ft

    241 Tollgate Blvd, Islamorada, FL 33036

    Near-new luxury home in coveted Toll Gate Shores, Islamorada, Florida. Near perfection, describes this newly constructed 3-bedroom, 3-bath residence offering single-level living with elevator access in the highly sought-after waterfront Keys community. Completed in 2024/2025 by renowned local contractor CBT Construction, the home blends modern luxury with a relaxed tropical elegance. The

    Keith Allen Coastal Realty of the Florida Keys

    241 Tollgate Blvd, Islamorada, FL 33036
  • /72

    $6,500,000

    • 5 Beds
    • 7 Baths
    • 5,153 Sq Ft

    430 Palm Dr, Islamorada, FL 33036

    Experience modern coastal luxury in Islamorada, where elevated design meets premier waterfront living. Built in 2017, this custom contemporary estate offers over 5,100sf of thoughtfully designed living space, set just 2 lots from the bay and across from a tranquil mangrove preserve that enhances both privacy and natural beauty.Boaters will love the setup - 100' of dockage with 2 elevator boat

    Claire Johnson Coastal Realty of the Florida Keys

    430 Palm Dr, Islamorada, FL 33036
  • /52

    $2,495,000

    • 4 Beds
    • 3 Baths
    • 2,294 Sq Ft

    439 Palm Dr, Islamorada, FL 33036

    VA Assumable!Experience refined waterfront living in the Florida Keys, where luxury meets effortless access to world-class boating and fishing. This exceptional canal-front residence is thoughtfully designed for discerning buyers who value privacy, convenience, and a true connection to the water.A private dock with newly added 15,000 lb boat lift provides seamless access to open water, allowing

    Caroline Hendrix Coldwell Banker Schmitt Islamorada

    439 Palm Dr, Islamorada, FL 33036
  • /60

    $3,200,000

    • 5 Beds
    • 3 Baths
    • 3,052 Sq Ft

    117 El Capitan Dr, Islamorada, FL 33036

    Newly remodeled waterfront home located in the highly desirable Port Antigua subdivision of Lower Matecumbe. This expansive residence offers five bedrooms and three bathrooms with an open living floor plan.The main living level features three bedrooms and two bathrooms, complemented by a spacious living, dining, and kitchen area--ideal for entertaining and relaxed Keys living. The lower level

    Lisa Frins Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

    117 El Capitan Dr, Islamorada, FL 33036
  • /38

    $5,600,000

    • 4 Beds
    • 4 Baths
    • 2,478 Sq Ft

    166 Bayview Dr, Islamorada, FL 33036

    Welcome to 166 Bayview Drive, a rare bayfront estate in the prestigious Safety Harbor neighborhood of Lower Matecumbe Key. Located at Mile Marker 74, this property offers direct access to Florida Bay and the Atlantic Ocean, placing you in the heart of Islamorada's world-class boating and sportfishing scene.The home enjoys unobstructed water views and nightly sunsets that paint the sky in

    Judy Rossignol Paradise Florida Keys Real Estate, a Luxury Brand

    166 Bayview Dr, Islamorada, FL 33036
  • /15

    $1,050,000

    • Land

    172 Iroquois Dr, Islamorada, FL 33036

    ACTIVE PERMIT - this waterfront lot is ready to build your dream Keys residence, no waiting in the lengthy line for a building allocation. The least expensive lot with TDR in the entire Village. Located in prestigious Lower Matecumbe Key in the Village of Islamorada on a private cul-de-sac. This lot is cleared and contains a 72' dock with a 5,000lb. boat lift in place. Canal has a navigable depth

    Lindsey Davis Ocean Sotheby's International Realty

    172 Iroquois Dr, Islamorada, FL 33036
  • /13

    $1,075,000

    • Land

    142 Gulfview Dr, Islamorada, FL 33036

    ACTIVE BUILDING AND DOCK PERMITS. START BUILDING TODAY! Your tropical dream awaits with the lowest-priced waterfront lot featuring an active building permit in Islamorada. Imagine waking up to sunlit mornings, salty breezes, and the soft embrace of warm sand beneath your feet. Welcome to White Marlin Beach, where your vision of paradise comes to life.Vacant lots with active building permits are a

    Eric Rizzo Ocean Sotheby's International Realty

    142 Gulfview Dr, Islamorada, FL 33036
  • /33

    $1,599,000

    • 3 Beds
    • 2 Baths
    • 1,278 Sq Ft

    121 Venetian Dr, Islamorada, FL 33036

    Discover the ultimate waterfront retreat in the heart of Islamorada, in the highly sought after neighborhood of White Marlin Beach. This captivating 3-bedroom, 2-bathroom gem is a dream come true. The interior features an open floor plan with 9-foot ceilings and ceramic tile. Embrace the coastal lifestyle with stunning water views right from your backyard and revel in the convenience of a private

    Ray Palacios TruRes Real Estate, Inc.

    121 Venetian Dr, Islamorada, FL 33036
  • /54

    $1,699,000

    • 4 Beds
    • 2 Baths
    • 1,680 Sq Ft

    164 Venetian Dr, Islamorada, FL 33036

    Boater’s dream home in White Marlin Beach, Islamorada. Unique 2-story single-family home with split layout, two 800 square feet 2BD/1BA units. Separate entrances and laundry in each unit, 70' dock with private boat ramp on a tranquil mangrove canal. This property is facing mangrove with maximum privacy, just 7 homes from the bay! Plenty of parking for RVs/trailers. Enjoy access to the White

    Po Yen Hsueh Compass Florida, LLC

    164 Venetian Dr, Islamorada, FL 33036
  • /58

    $7,995,000

    • 4 Beds
    • 5 Baths
    • 4,048 Sq Ft

    91 Iroquois Dr, Islamorada, FL 33036

    Discover paradise in Islamorada, where you can enjoy beautiful ocean views, protected dockage, and resort-style amenities. This home blends luxury living with the Florida Keys lifestyle and is designed with both entertainment and relaxation in mind. Concrete construction and equipped with impact windows/doors, Interlock Aluminum Slate Roofing and a solar generator, this home can weather any

    Eric Smith Coastal Realty of the Florida Keys

    91 Iroquois Dr, Islamorada, FL 33036
  • /16

    $880,000

    • Land

    149 Iroquois Dr, Islamorada, FL 33036

    This exceptional canal-front vacant lot on Lower Matecumbe Key represents a truly prime piece of cleared real estate. The permit for this property is ready to be picked up, allowing you to bypass typical delays and start construction immediately. Seize this rare opportunity to build your dream home in a highly sought-after Keys location. THIS PROPERTY has a permit ready to be picked up at the

    Nancy Hershoff Coldwell Banker Schmitt Islamorada

    149 Iroquois Dr, Islamorada, FL 33036
  • /80

    $2,900,000

    • 3 Beds
    • 3 Baths
    • 2,374 Sq Ft

    122 Court Contessa, Islamorada, FL 33036

    An unparalleled waterfront sanctuary in the prestigious and private beachside of Port Antigua, where luxury meets the laid-back charm of the Florida Keys. This impeccably upgraded home offers the perfect blend of refined coastal living and island serenity -- ideal for those seeking an exceptional full-time residence or a serene island escape. 3 Bedroom; 3 Full Bathrooms + extra 1/2 Bath; Private

    Lourdes Martin-Rosa The Keyes Company

    122 Court Contessa, Islamorada, FL 33036
  • /82

    $6,150,000

    • 6 Beds
    • 7 Baths
    • 5,100 Sq Ft

    194 Buttonwood Ln, Islamorada, FL 33036

    Welcome to 194 Buttonwood Lane, a rare waterfront sanctuary nestled in the prestigious Safety Harbor enclave. This meticulously designed 6-bedroom, 7-bathroom residence seamlessly blends architectural elegance with modern comfort. The heart of the home features a chef's kitchen outfitted with top-of-the-line appliances, custom cabinetry, and breath taking stone finishes on the countertops and

    Mike Jones Fairchild Partners, Inc.

    194 Buttonwood Ln, Islamorada, FL 33036
  • /46

    $8,950,000

    • 8 Beds
    • 10 Baths
    • 5,392 Sq Ft

    162 Bayview Dr, Islamorada, FL 33036

    Nestled in the exclusive Safety Harbor enclave of Islamorada, this stunning Gulfside estate offers an unparalleled blend of luxury and tranquility. Situated on a prime point, the property boasts breathtaking open water views and the added advantage of protected dockage, making it a boater's paradise. With a concrete seawall, two boat lifts equipped with power and water, and a fish cleaning

    Nancy Muniz Coldwell Banker Realty - Coral Gables

    162 Bayview Dr, Islamorada, FL 33036
  • /81

    $3,500,000

    • 4 Beds
    • 3 Baths
    • 2,519 Sq Ft

    133 Sunset Dr, Islamorada, FL 33036

    The Ospreys are back! Welcome to The Osprey's Nest; your perch by the Ocean in one of Islamorada's most coveted locations. Wake up to the sunrise and take a stroll down the turtle nesting beach, while also having the convenience of protected canalside dockage across the street. 20' dock but brought in stern-to, can accommodate larger boats. Spacious floor plan for all to enjoy, third story

    The Florida Keys Sold Sisters Ocean Sotheby's International Realty

    133 Sunset Dr, Islamorada, FL 33036
  • /22

    $1,550,000

    • 3 Beds
    • 2 Baths
    • 1,278 Sq Ft

    121 Venetian Dr, Islamorada, FL 33036

    Discover the ultimate waterfront retreat in the heart of Islamorada, in the highly sought after neighborhood of White Marlin Beach. This captivating 3-bedroom, 2-bathroom gem is a dream come true. The interior features an open floor plan with 9-foot ceilings and ceramic tile. Embrace the coastal lifestyle with stunning water views right from your backyard and revel in the convenience of a private

    Robert Santana TruRes Real Estate Inc.

    121 Venetian Dr, Islamorada, FL 33036
  • /112

    $5,999,999 New Construction

    • 5 Beds
    • 5.5 Baths
    • 5,320 Sq Ft

    181 Nautilus Dr, Islamorada, FL 33036

    Brand new 2026 coastal luxury in Islamorada's White Marlin Beach. 181 Nautilus Dr offers the ultimate Keys lifestyle with 5 bedrooms, 5.5 baths, and 5,320 SF of living area across three levels. Served by a private elevator that opens on all floors. Designed for indoor/outdoor living, enjoy a resort-style pool and a modern outdoor setting ideal for entertaining. Built for peace of mind with impact

    Karla Gil Coldwell Banker Realty - Coral Gables

    181 Nautilus Dr, Islamorada, FL 33036
  • /29

    $14,900,000 New Construction

    • 5 Beds
    • 8 Baths
    • 6,367 Sq Ft

    236 Costa Bravo Dr, Islamorada, FL 33036

    A rare architectural masterpiece by renowned architect Max Strang, this modern coastal estate in Port Antigua, Islamorada, redefines luxury waterfront living. Set on a private sandy beach, the residence offers 5 bedrooms, 6 full baths and 2 half baths across 6,367 SF of interior space and 10,483 total SF. Strang's signature tropical modernist design showcases natural materials, clean lines, and

    Courtney Conley Serhant Florida LLC - Coconut Grove

    236 Costa Bravo Dr, Islamorada, FL 33036
  • /113

    $5,000,000 New Construction

    • 5 Beds
    • 5 Baths
    • 4,064 Sq Ft

    88 W Plaza Del Lago, Islamorada, FL 33036

    Experience elevated coastal living in this elegant Port Antigua retreat. Thoughtfully designed for comfort, privacy, effortless entertaining and situated in a prime waterfront location, this beautiful resort-style residence offers generous living spaces, including both upstairs and downstairs primary suites, three additional guest suites, a dedicated office, shaded porches on both levels and a

    The Florida Keys Sold Sisters Ocean Sotheby's International Realty

    88 W Plaza Del Lago, Islamorada, FL 33036
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