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Cudjoe Key, FL Houses for Sale

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  • /43

    $949,000 Open Sat 11AM - 1PM

    • 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

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    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (305) 518-1095

    22954 Buccaneer Ln, 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

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    Michelle Howerton

    Brenda Donnelly Real Estate LLC

    (833) 381-1226

    22939 Privateer Dr, Summerland 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

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    Sandra Tuttle

    Island Welcome Real Estate

    (786) 841-9203

    1083 Labat Ln, Cudjoe 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

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    Austin Kimbler

    Expert Realty LLC (HQ)

    (645) 220-0519

    22852 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

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    Anneliese Dietrick

    Coldwell Banker Schmitt Lower Keys (KW)

    (786) 882-7259

    22739 Buccaneer Ln, 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

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    Miriam Novotny

    Compass Florida, LLC

    (786) 667-5744

    20920 5th Ave W, 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,

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    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (844) 970-3222

    51 Sawyer Dr, 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

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    Anneliese Dietrick

    Coldwell Banker Schmitt Lower Keys (KW)

    (645) 241-6029

    22865 Redfish 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

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    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (833) 853-7147

    153 Peg Leg Ln, 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

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    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (833) 614-3802

    21250 Conch Dr, Summerland Key, FL 33042
  • /29

    $1,325,000

    • 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. Perfect 1031 opportunity! This 3-bedroom, 2-bath coastal retreat is being offered fully furnished, with stylish furnishings purchased just two years ago,

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    Sandra Tuttle

    Island Welcome Real Estate

    (786) 869-3656

    22974 Anne Bonny Ln, Summerland Key, FL 33042
  • /125

    $999,000

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

    22748 Blackbeard Ln, Cudjoe Key, FL 33042

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

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    Lindsay Ryan

    EXP Realty LLC

    (786) 807-7897

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

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    Terrance Sullivan

    Ocean Sotheby's International Realty

    (786) 204-2360

    755 Sawyer Dr, Summerland Key, FL 33042
  • /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

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    Terrance Sullivan

    Ocean Sotheby's International Realty

    (786) 465-7217

    755 & 744 Sawyer Dr, Cudjoe Key, FL 33042
  • /39

    $1,499,000

    • 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

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    Lisa Ferringo

    Coldwell Banker Schmitt Real Estate Co

    (786) 952-7261

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

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    Terry Garcia

    Keller Williams Key West Compass Realty

    (786) 321-8407

    22737 Blackbeard Ln, Cudjoe Key, FL 33042
  • /30

    $430,000

    • 2 Beds
    • 1 Bath
    • 415 Sq Ft

    21857 Disturbed Pine Rd, Summerland Key, FL 33042

    Acre Property! I've heard it said privacy is the ultimate luxury. Your Keys bungalow in the woods with a separate screened porch enclosure 13 X 18 plus a storge room 9 X 12. Connected to the house by a wood deck walkway. Artist retreat, man cave or maybe just because you love privacy and want an escape. Lots of potential. Are you handy! Additionally, there are 2 carports, Multiple storage areas.

    Rose Dell Keller Williams Key West Compass Realty

    21857 Disturbed Pine Rd, 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
  • /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
  • /38

    $1,024,000

    • 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
  • /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
  • /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
  • /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
  • /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
  • /61

    $1,675,000

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

    1163 de Lussan Ln, Summerland Key, FL 33042

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

    Jan Fritz Coldwell Banker Schmitt RE Co.

    1163 de Lussan Ln, Summerland Key, FL 33042
  • /69

    $2,195,000

    • 5 Beds
    • 3 Baths
    • 1,903 Sq Ft

    125 Colson Dr, Summerland Key, FL 33042

    TRANSIENT LICENSE FOR NIGHTLY RENTALS BRINGING IN 250k+! WITH OPEN WATER VIEWS! ALMOST 2 ACRES TOTAL WITH 4 LOTS! THIS PROPERTY IS A ONE OF A KIND! A TRUE ''UNICORN!'' Turnkey Vacation Rental with 4 bedrooms and 2 baths in Main House which is a charming and OLD FLORIDA KEYS STYLE PROPERTY! Privacy, lush vegetation, stunning Open water views from the balconies from almost every room! Original

    Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

    125 Colson Dr, Summerland Key, FL 33042
  • /29

    $899,000 Open Sun 12PM - 2PM

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft

    463 Lesrohde Dr, Ramrod Key, FL 33042

    Don't miss the chance to own this exceptional piece of paradise--schedule a private showing today!Be the first to call this stunning, newly constructed Affinity-built home yours! Located in desirable Ramrod Key, this energy-efficient 3-bedroom, 2-bathroom residence boasts premium quality throughout. Featuring high-end fixtures, Pella impact-resistant windows and doors, and thoughtful

    Sarah Dolson Keller Williams Key West Compass Realty

    463 Lesrohde Dr, Ramrod Key, FL 33042
  • /42

    $2,089,000

    • 5 Beds
    • 3 Baths
    • 1,978 Sq Ft

    94 Sacarma Dr, Cudjoe Key, FL 33042

    Rare Licensed Oceanfront Short-Term Vacation Rental in the Lower Florida Keys. Welcome to Fandango, a highly successful transient (daily-weekly) vacation rental home offering an exceptional investment opportunity and a personal retreat. This stunning 5-bedroom, 3-bathroom property, built in 2011 and expanded in 2018, was thoughtfully designed as the ultimate family vacation rental retreat.

    Michelle Blades Realty Executives Florida Keys Old Town

    94 Sacarma Dr, Cudjoe Key, FL 33042
  • /16

    $989,999

    • 3 Beds
    • 3 Baths
    • 960 Sq Ft

    22961 John Avery Ln, Summerland Key, FL 33042

    Boater's Paradise in Cudjoe Key under 1 million! Priced to Sell! Bring all offers!Bring your boat, jet skis, and sense of adventure! This upgraded two-story coastal retreat is designed for water lovers, featuring over 60 feet of dock space complete with shore power, plumbing, and brand-new dual jet ski davits plus a boat lift -- perfect for launching into the Florida Keys lifestyle.The lower

    Rayden Vega Casa Miami Real Estate

    22961 John Avery Ln, Summerland Key, FL 33042
  • /38

    $1,490,000

    • 2 Beds
    • 2 Baths
    • 1,127 Sq Ft

    1113 de Lussan Ln, Summerland Key, FL 33042

    Breathtaking Open Water Home in Cudjoe Key - Comes FULLY FURNISHED!Welcome to paradise! This stunning 2-bedroom, 2-bath home captures magnificent open water views and embodies the ultimate Florida Keys lifestyle.Main Living Area:Step inside to an open-concept kitchen, living room, and dining area bathed in natural light. Every detail is designed to highlight the beauty of the surrounding water

    Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

    1113 de Lussan Ln, Summerland Key, FL 33042
  • /43

    $1,050,000

    • 2 Beds
    • 2 Baths
    • 1,008 Sq Ft

    22837 Calico Jack Cir, Summerland Key, FL 33042

    Open Water Views & Sunset Skies with great boating access describes this Concrete Block Construction Home with pre-stress concrete beams holding up a poured concrete floor. Home features open floor plan with vaulted ceilings, tile floors throughout, partial walk-around, storm shutters, 2018 A/C, impact front door and metal roof. Storage room below and ample parking too. Quick commute to Key West,

    Beata Sharpe Coldwell Banker Vanguard Realty

    22837 Calico Jack Cir, Summerland Key, FL 33042
  • /59

    $1,529,999 Open Sun 11AM - 2PM

    • 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
  • /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

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.

Home Trends in Cudjoe Key, FL

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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