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Cudjoe Key, FL Houses for Sale

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  • /49

    $1,998,000

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

    22542 Jolly Roger Dr, Summerland Key, FL 33042

    SELLER FINANCING AVAILABLE! This Beautiful Oceanfront Home in Cudjoe Key has undergone a full renovation and awaits its new owner! All new impact doors and windows, new AC, new flooring throughout and a stunning custom kitchen with granite countertops and stainless steel appliances are a few of the many updates in this amazing renovation . Offering Four generous size bedrooms with Three full

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    Emily Lombard

    Ocean Sotheby's International Realty

    (786) 788-8217

    22542 Jolly Roger Dr, Summerland Key, FL 33042
  • /28

    $1,375,000 Open Sat 10AM - 1PM

    • 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

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    Sandra Tuttle

    Island Welcome Real Estate

    (786) 869-3656

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

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    Matthew Sheehan

    Ocean Sotheby's International Realty

    (786) 882-7957

    21855 Spain Blvd, Summerland 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
  • /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

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    Lisa Ferringo

    Coldwell Banker Schmitt Lower Keys (KW)

    (645) 230-1509

    22954 Buccaneer Ln, Summerland Key, FL 33042
  • /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

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    Michelle Howerton

    Brenda Donnelly Real Estate LLC

    (855) 548-0123

    22892 Jolly Roger Dr, Summerland Key, FL 33042
  • /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

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    Lisa Ferringo

    Coldwell Banker Schmitt Lower Keys (KW)

    (786) 952-7261

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

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    Matthew Sheehan

    Ocean Sotheby's International Realty

    (645) 215-8837

    21865 Spain Blvd, Summerland Key, FL 33042
  • /61

    $2,250,000

    • 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

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    Sandra Tuttle

    Island Welcome Real Estate

    (786) 756-9163

    743 Pattison Dr, Summerland Key, FL 33042
  • /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

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    Lisa Ferringo

    Coldwell Banker Schmitt Lower Keys (KW)

    (786) 551-4933

    51 Drost Dr, 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
  • /43

    $1,799,999

    • 4 Beds
    • 2 Baths
    • 2,074 Sq Ft

    22562 Jolly Roger Dr, Summerland Key, FL 33042

    Jolly Roger Drive on Cudjoe Key, where custom design meets open water views. This 4-bedroom, 2-bathroom residence showcases a designer kitchen with Viking appliances and high-end finishes, perfect for entertaining. The first floor offers two guest bedrooms, an office, and a full bath, while the second floor features a spacious guest room and the primary suite with a private balcony, ensuite bath,

    Krystal Thomas eXp Realty LLC

    22562 Jolly Roger Dr, Summerland Key, FL 33042
  • /45

    $1,950,000

    • 2 Beds
    • 2 Baths
    • 1,281 Sq Ft

    489 Sawyer Dr, Summerland Key, FL 33042

    OCEANFRONT & CANALFRONT GEM-- A Rare Slice of ParadiseThis exceptional 17,560 sq. ft. property offers the best of both worlds with stunning open water views and protected canal frontage. The main home is a beautifully maintained 2 bedroom, 2 bath residence featuring 155 feet of sweeping ocean vistas, impact windows and sliding glass doors, and a layout designed to showcase breathtaking sunrises

    Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

    489 Sawyer Dr, Summerland 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
  • /43

    $1,125,000

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

    22837 Calico Jack Cir, Summerland Key, FL 33042

    Seller says Bring Offers....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

    Beata Sharpe Coldwell Banker Vanguard Realty

    22837 Calico Jack Cir, Summerland Key, FL 33042
  • /65

    $1,099,000

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

    165 Cutlass Ln, Summerland Key, FL 33042

    Discover Your Dream Waterfront Home in the Florida Keys! This stunning canal-front residence boasts 4 spacious bedrooms and 3 bathrooms. With 2,448 sq. ft. of thoughtfully laid-out living space, this home is perfect for accommodating large families and entertaining guests.Step onto the expansive covered balconies on both floors, where you can relax and take in the serene canal views. The generous

    Justyn Ewald Expert Realty LLC (HQ)

    165 Cutlass Ln, Summerland Key, FL 33042
  • /2

    $324,999

    • 2 Beds
    • 2 Baths
    • 980 Sq Ft

    37 Yardarm Rd Unit 1, Cudjoe Key, FL 33042

    This sale is for one 6000 square foot lot with a home in need of repairs or replacement.

    Joseph Ordini Keller Williams Key West Compass Realty

    37 Yardarm Rd Unit 1, Cudjoe Key, FL 33042
  • /9

    $849,000

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

    22920 Privateer Dr, Summerland Key, FL 33042

    Mariner's Dream - Your Waterfront Paradise Awaits! Welcome to this elevated, stilted two-story home offering 1,560 SqFt of living space and a versatile 4th bedroom that doubles as a den. Situated on a deep, wide, and pristine canal in the desirable Cutthroat Harbor Estates of Cudjoe Key, this home provides the perfect canvas for renovation. With new windows and siding (Completed 2023), much of

    Robin Nilsson Keller Williams Key West Compass Realty

    22920 Privateer Dr, Summerland Key, FL 33042
  • /39

    $1,100,000

    • 3 Beds
    • 2 Baths
    • 2,198 Sq Ft

    21073 7th Ave, Summerland Key, FL 33042

    Florida Keys Waterfront Paradise - 80' Dock & No Bridges to Open Water!Nestled in a boater's paradise, this 2,198 sq. ft. 3-bed, 2-bath home offers a split floor plan for privacy and comfort. Inside, the spacious kitchen boasts stainless steel appliances, generous cabinet space, and ample corian counter space perfect for cooking up your fresh catch. The open-concept living and dining area flows

    Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

    21073 7th Ave, Summerland Key, FL 33042
  • /41

    $2,450,000

    • 2 Beds
    • 2 Baths
    • 1,577 Sq Ft

    1176 Thatch Ln, Summerland Key, FL 33042

    Unobstructed Ocean views, your own Private Oasis! On a canal with easy access to both the Ocean and Back Country. Whether you're seeking a full time residence, vacation getaway, or income-producing investment, this waterfront gem checks every box! Huge 24,829 Sqft LOT with plenty of room to add on. The home has consistent vacation rentals booked 4+ months out of the year, every year!! (income

    Jonathan Minerick Homecoin.com

    1176 Thatch Ln, Summerland Key, FL 33042
  • /42

    $2,200,000

    • 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
  • /69

    $2,249,000 Pre-Foreclosure

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

    125 Colson Dr, Summerland Key, FL 33042

    THIS PROPERTY IS A ONE OF A KIND! A TRUE ''UNICORN!'' TRANSIENT LICENSE FOR NIGHTLY RENTALS ALLOWED! OPEN WATER VIEWS! ALMOST 2 ACRES TOTAL WITH 4 LOTS! 5 bedrooms and 3 baths in this charming and OLD FLORIDA KEYS STYLE PROPERTY! Privacy, lush vegetation, stunning Open water views, balconies from almost every room! Original hardwood floor, tons of character and warmth in this lovely home! Large

    Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

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

    $1,549,000

    • 3 Beds
    • 2 Baths
    • 1,872 Sq Ft

    20841 8th Ave W, Cudjoe Key, FL 33042

    Meticulously maintained and located in the desirable boating community of Cudjoe Gardens, this nearly 1,900 sq ft home includes 90 feet of dockage, a 10,000 lb boat lift, hurricane impact windows, doors, and garage door, as well as a gorgeous pool creating your own private oasis. A boater's paradise with easy access to both ocean side and gulf side! The inside boasts 3 spacious bedrooms and an

    Collin Tingle Coldwell Banker Schmitt Lower Keys (KW)

    20841 8th Ave W, Cudjoe Key, FL 33042
  • /59

    $2,950,000 Open Sun 1PM - 3PM

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

    20844 4th Ave W, Summerland Key, FL 33042

    SOLD TURNKEY! PRICE INCLUDES FURNISHINGS, 2006 PONTOON BOAT & 2021 JET SKI! A remarkable waterfront estate in the prestigious neighborhood of Cudjoe Gardens. When you first walk up one of the two brick paver driveways on this over sized lot you will find two entrances, beautiful landscaping, tropical fruit trees, key limes, mangoes, lemons, bananas and avocados! This stunning concrete residence

    Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

    20844 4th Ave W, Summerland Key, FL 33042
  • /45

    $899,999

    • 3 Beds
    • 2 Baths
    • 950 Sq Ft

    23012 Snapper Ln, Summerland Key, FL 33042

    Welcome to 23012 Snapper Lane in Beautiful Cudjoe Key, FL.This Three (3) bedroom and Two (2) bathroom elevated, waterfront on a corner lot is the one you have been looking for, with a great price too!This home is built to last and has been meticulously cared for. Come bring your boat and sit back and enjoy your favorite beverage on this oversized backyard. Tons of storage for all your toys, and

    Bobby Coe RE/MAX Keys Connection (KW)

    23012 Snapper Ln, Summerland Key, FL 33042
  • /38

    $1,599,000

    • 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
  • /29

    $899,000

    • 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
  • /125

    $1,190,000

    • 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, &

    Lindsay Ryan EXP Realty LLC

    22748 Blackbeard Ln, 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
  • /23

    $3,750,000

    • 4 Beds
    • 4.5 Baths
    • 3,228 Sq Ft

    22815 Port Royal Ln, Summerland Key, FL 33042

    DIRECT OCEAN FRONT 323FT of Water Frontage- BOATERS PARADISE FOUND with room for 3 Boats on unobstructed sunset view over open water - oversized corner lot with water on 2 sides at end of a private road offering picture perfect sunsets in a protected bay! INCOME PRODUCING!, includes 175' of open water and 148' of canal frontage featuring a 90' concrete dock, and a private kayak launch. The main

    Rhonda Gailey Gailey Enterprises Real Estate

    22815 Port Royal Ln, 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
$899,000
Median Single Family Sale Price
$1,145,000
Average Price Per Sq Ft
$844
Number of Homes for Sale
8
Last 12 months Home Sales
12
Months of Supply
8.00
Median List Price
$1,175,000
Median Change From 1st List Price
7%
Median Home Sale Price YoY Change
-35%
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