Homes for Sale in 33042

/32
$1,689,000
- 3 Beds
- 2 Baths
- 2,144 Sq Ft
1151 Sugarloaf Blvd, Summerland Key, FL 33042

Truly unique and private estate property on the desired Sugarloaf Blvd. in Sugarloaf Shores. Ground level CBS house sits on 2 waterfront lots. Totaling over 1.3 acres of land and approx. 400 ft. of canal front. Amazing view up the canal to the open water. The large floor plan featuring 3 bedrooms, 2 baths, den/office and fireplace. Kitchen has stainless appliances, quartz countertops and lots of

Wendy Zintsmaster Truman & Co. (KW)

1151 Sugarloaf Blvd, Summerland Key, FL 33042
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/45
$1,950,000 Open Fri 12PM - 2PM
- 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
/41
$1,599,900
- 4 Beds
- 3 Baths
- 1,704 Sq Ft
951 Lagoon Dr, Summerland Key, FL 33042

Need space for family and friends? Come see this 4 bedroom/ 3 Full Baths Summerland Cove Isles beautiful & spacious home today. Features open floor plan, large storage area below with a tackle room, metal roof, impact windows and shutters. French doors lead outdoors to a large screen porch overlooking the beautiful deep canal. Great kitchen area with a gas stove, family room, dining room, laundry

Beata Sharpe Coldwell Banker Vanguard Realty

951 Lagoon Dr, Summerland Key, FL 33042
/47
$1,255,000
- 2 Beds
- 2 Baths
- 864 Sq Ft
1021 Caribbean Dr E, Summerland Key, FL 33042

COASTAL RETREAT in desirable SUMMERLAND KEY COVE situated on a prime canal! Calling all BOATERS that seek deep draft flow-through water - you'll be to the Atlantic or Gulf in minutes. Slip away to your Keys retreat - move-in ready! You'll love the remodeled kitchen and baths so you can spend your time splashing in the pool or sipping a cool drink under the tiki. Completely furnished with

Donna Pezzi Keller Williams Key West Compass Realty

1021 Caribbean Dr E, Summerland Key, FL 33042
/39
$1,199,000
- 3 Beds
- 2 Baths
- 1,400 Sq Ft
164 Tortuga Ln, Summerland Key, FL 33042

JUST REDUCED $206,000Now Offered at $1,119,000 Welcome to 164 Tortuga Lane, a solid concrete stilted home perfectly positioned on a wide canal with quick access to open water. Recently repriced over $200,000 below original list, this is one of the best values in the Lower Keys waterfront market.This move-in-ready property features 3 bedrooms, 2 bathrooms, 1,400 sq ft of living space, and a 6,000

Kathryn Baldwin Berkshire Hathaway HomeServices Knight & Gardner Realty

164 Tortuga Ln, Summerland Key, FL 33042
/43
$1,275,000
- 3 Beds
- 2 Baths
- 1,380 Sq Ft
1032 Caribbean Dr E, Summerland Key, FL 33042

The ''COPPER TOP'' - Solid construction with a metal roof located on a beautiful flow-through canal in Summerland Key Cove. This 3 bedroom, 2 bath home checks all the boxes. You'll love the modern remodeled kitchen with vaulted ceilings in the living area, tiled floors throughout and a screened in balcony that allows you to open up the house and enjoy the breezes. Furnished for your

Donna Pezzi Keller Williams Key West Compass Realty

1032 Caribbean Dr E, Summerland Key, FL 33042
/49
$1,199,000
- 3 Beds
- 2 Baths
- 1,408 Sq Ft
27426 Martinique Ln, Summerland Key, FL 33042

Motivated seller offers new price reduction on this elevated 3 bedroom 2 bath home with 60 ft concrete dock and 120 ft waterfront! Boater's dream with canal access to open water and NO bridges. Updates include roof, impact windows and doors, complete kitchen remodel, and bath in 2018. Central A/C replaced in 2024. Exterior painted 2022. Screened porch offers perfect place to start your

Susan Hawkinson Bascom Grooms Real Estate (KW)

27426 Martinique Ln, Summerland Key, FL 33042
/40
$1,205,400
- 3 Beds
- 2 Baths
- 1,056 Sq Ft
27350 Barbados Ln, Ramrod Key, FL 33042

Paradise Found: Boater's Dream & Poolside Oasis!Welcome to your slice of island paradise! This fully furnished, turn key 3-bedroom, 2-bathroom coastal retreat offers the perfect blend of luxurious living and peace of mind, designed for those who love the water, sunshine, and ultimate relaxation.Step into a spacious, open-concept layout. Flooded with natural light, thanks to hurricane impact

Natallie Liz Expert Realty LLC (HQ)

27350 Barbados Ln, Ramrod Key, FL 33042
/46
$1,225,000
- 3 Beds
- 2 Baths
- 1,250 Sq Ft
43 Venetian Way, Summerland Key, FL 33042

Beautifully updated 3 bedroom 2 bath home, with effective build date of 2015 and completely renovated in 2018 including New Electrical, Plumbing, HVAC, Roof, Tankless Water heater, Flooring, Kitchen, Bathrooms, Windows, & Doors, landscaping/sprinkler system, TESLA charging station and an amazing new paved driveway installed in 2021. This is a split floor plan for privacy with amazing screened

Lori Cameron Buy The Keys

43 Venetian Way, Summerland Key, FL 33042
/35
$1,380,000
- 3 Beds
- 2 Baths
- 2,100 Sq Ft
22822 John Silver Ln, Summerland Key, FL 33042

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Halley Haack Coldwell Banker Schmitt Real E

22822 John Silver Ln, Summerland Key, FL 33042
/42
$1,299,000
- 3 Beds
- 2 Baths
- 2,081 Sq Ft
27038 Angelfish Rd, Summerland Key, FL 33042

Owner financing possible **Stunning 3-Bedroom, 2-Bath Home on 15,000 Sq Ft Lot with Resort-Style Pool and Spa**Welcome to your dream home! This spacious 3-bedroom, 2-bathroom property offers everything you need for comfortable living and entertaining. Nestled on a generous 15,000 sq ft lot, you'll enjoy plenty of space both indoors and outdoors. The centerpiece of this property is the luxurious

Louis Paez Coldwell Banker Schmitt Real Estate Co. (KW)

27038 Angelfish Rd, Summerland Key, FL 33042
/16
$1,195,000
- 3 Beds
- 3 Baths
- 1,400 Sq Ft
17171 Seagrape Ln, Summerland Key, FL 33042

RARE OPPORTUNITY HERE! This home is perfect for a DIY, Flipper or builder. Bring your imagination as it's located in very desirable location of Sugarloaf Shores where homes are over 2++ million dollars. It just needs a makeover but has great bones and many things you won't get now. Full 2 car garage with impact doors and shop. Legal downstairs bath. Large lot on 70' wide flow through canal.

Marie Howe Century 21 Circle - Key West

17171 Seagrape Ln, Summerland Key, FL 33042
/43
$1,999,900
- 3 Beds
- 2 Baths
- 2,156 Sq Ft
1165 Lagoon Dr, Summerland Key, FL 33042

Exceptional waterfront pool home in Summerland Key! This beautifully updated 2156sqft concrete home is located in the desirable neighborhood of Summerland Cove, known for its incredible boating access, deep-water flow through canals and close location to Key West (just 24 miles). Enjoy the ocean and lagoon views from the kitchen, living room, dining room, loft and screened patio, or from the 64'

Laura Koski The Keyes Company (Tequesta)

1165 Lagoon Dr, Summerland Key, FL 33042
/35
$1,299,000
- 3 Beds
- 2 Baths
- 2,392 Sq Ft
28565 Anne Bonny Rd, Summerland Key, FL 33042

Spacious canal front home in desirable Jolly Roger Estates on Little Torch Key! No details were spared in the recent renovation transformation, resulting in impeccable design and comfort, and the result is a serene and comforting destination, perfect for family getaways or as an income generating investment property. Kitchen updates include stainless steel appliances and granite countertops,

Banks Prevatt Coldwell Banker Schmitt RE Co. Lower Keys Office

28565 Anne Bonny Rd, Summerland Key, FL 33042
/40
$998,000
- 2 Beds
- 2 Baths
- 1,086 Sq Ft
22846 Port Royal Ln, Cudjoe Key, FL 33042

Stunning open-water views, unforgettable sunsets over the bay, and direct ocean access from this beautifully updated 2BD/2BA Cudjoe Key retreat! Enjoy panoramic bay views, a highly sought-after private boat launch (no longer permitted to be built), and canal with quick access to the Atlantic and Back Country. Upgrades include hurricane-rated impact windows and sliders, a new hurricane-proof

Diane Corliss Coldwell Banker Schmitt Lower Keys (KW)

22846 Port Royal Ln, Cudjoe Key, FL 33042
/25
$569,700
- 2 Beds
- 1 Bath
- 718 Sq Ft
701 Spanish Main Dr Unit 335, Cudjoe Key, FL 33042

Licensed nightly rental. Brand new raised Sea Wall!! Discover island living at 701 Spanish Main Dr, Unit 335 in Cudjoe Key, FL. 2Bd/1Ba successful vacation rental located in a premium location on the water with open water views and features a 35' concrete seawall for docking a boat. Dock is equipped with dock posts, cleats, water, and storage. Large patio space to enjoy paradise overlooking the

Sarah Dolson Keller Williams Key West Compass Realty

701 Spanish Main Dr Unit 335, Cudjoe Key, FL 33042
/24
$580,175
- 2 Beds
- 2 Baths
- 816 Sq Ft
701 Spanish Main Dr Unit 79, Cudjoe Key, FL 33042

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

Sarah Dolson Keller Williams Key West Compass Realty

701 Spanish Main Dr Unit 79, Cudjoe Key, FL 33042
/9
$199,500
- Land
Vacant Picard Ln, Cudjoe Key, FL 33042

Waterfront vacant lot waiting for you: Build your dream home here! Located in the highly desireable Cutthroat Harbor Estates neighborhood. This is a fantastic opportunity to build your dream home,complete it with a boat dock to enjoy the Florida Keys Lifestyle. This property is situated on a quiet street with only 2 homes to pass by, and you're boat will be in the open water. It's off the beaten

lee Sanders KeyIsle Realty

Vacant Picard Ln, Cudjoe Key, FL 33042
/19
$745,000
- Land
28587 Peg Leg Rd Little Torch Alley, Little Torch Key, FL 33042

Vacant Land on Canal waiting on permit 41.5 points today for a 3497 sq.foot house with a roof top area. Permit number# SFDUP -2025-0096 Four-bedroom three-bathroom house. Builder will build for the buyer price and terms to be negotiated Dock and plans are included. Ranked for next quarter to be delivered a permit. Pictures shown as built house.

Barbara Eads Barbara Eads Realty

28587 Peg Leg Rd Little Torch Alley, Little Torch Key, FL 33042
/60
$5,500,000
- 3 Beds
- 3 Baths
- 2,088 Sq Ft
481 E Shore Dr, Summerland Key, FL 33042

Exceptional Investment Opportunity in the Lower Florida Keys! Owner and private financing are available. This is one of the very few vacation rental properties licensed for daily, weekly, or monthly rentals. Boasting an impressive occupancy rate and generating up to $400,000 annually, this property offers stress-free, passive income in Summerland Key, a premier location. Discover a rare gem in

Mariana Zaleska-Montadas Berkshire Hathaway HomeServices Keys Real Estate

481 E Shore Dr, Summerland Key, FL 33042
/6
$275,000
- Land
27313 Antigua Rd, Ramrod Key, FL 33042

Build Your Dream Home in the Florida Keys! Currently in ROGO! You can submit an updated application to maximize your point to reach 43.5 Points! Seller has full plans/engineering and and additional 2 point lot that comes with this purchase! An exceptional opportunity awaits in Ramrod Key, FL! This vacant lot is currently in ROGO AND includes a 2-point dedication lot--bringing your potential

Pamela Stangler Expert Realty LLC

27313 Antigua Rd, Ramrod Key, FL 33042
/13
$85,000
- Land
- 4.00 Acres
- $21,250 per Acre
LOT 8 Little Knockemdown Key Unit AKA Parcel 23, Summerland Key, FL 33042

Offshore island 4 acre lot in the heart of the Great White Heron Wildlife refuge is suitable for temporary camping and exploration. World class flats fishing for bonefish, tarpon, permit and redfish nearby. Located on Southwest end of Little Knockemdown Key. Accessible by kayak, paddle board and shallow draft vessels. Privacy and nature abound here on Little Knockemdown Key - No roads or

Banks Prevatt Coldwell Banker Schmitt RE Co. Lower Keys Office

LOT 8 Little Knockemdown Key Unit AKA Parcel 23, Summerland Key, FL 33042
/29
$239,000
- Land
701 Spanish Main Dr Unit 621, Cudjoe Key, FL 33042

RV Lot 621 - Priced to Sell!! Calling investors, locals and snowbirds - This is an active vacation rental, it also has rights to build a home, or just enjoy this for yourself year round or as a second homebase. Lushly Landscaped 35' x 69' Lot with Ocean Views & Full Hookups. This beautifully landscaped RV lot offers amazing privacy and is located in the gated, community of Venture out on Cudjoe

Kelly Gardner Bluescape Real Estate

701 Spanish Main Dr Unit 621, Cudjoe Key, FL 33042
/28
$999,999
- 3 Beds
- 3 Baths
- 1,859 Sq Ft
146 Sugarloaf Dr, Summerland Key, FL 33042

Canal-Front Home in Sugarloaf - Boat Lift Included - Enjoy the ultimate Keys lifestyle in this well-maintained 3-bedroom, 2-bath canal-front home in beautiful Sugarloaf Key. Located on a quiet street, this move-in ready property offers direct boating access and your own private dock with boat lift--perfect for easy access to both the Gulf and Atlantic with no bridges. Inside, the home features an

Joe Dudek Expert Realty LLC (HQ)

146 Sugarloaf Dr, Summerland Key, FL 33042
/35
$1,199,000
- 2 Beds
- 2 Baths
- 1,420 Sq Ft
2231 Middle Torch Rd, Summerland Key, FL 33042

Opportunities like this are few and far between. This extraordinary offering includes two adjoining 2.5-acre parcels, totaling 5 acres of land -- Truly a rare find in the Florida Keys. Each lot measures 110 x 990 feet, offering an abundance of space, privacy, and potential.The property features two dwellings -- a single-family residence and a manufactured dwelling on the other -- each with 1

Stephany Duvall Engel & Volkers Marathon

2231 Middle Torch Rd, Summerland Key, FL 33042
/52
$439,000
- 2 Beds
- 2 Baths
- 864 Sq Ft
701 Spanish Main Dr Unit 635, Cudjoe Key, FL 33042

Transient Rental License! Welcome to the epitome of comfort and convenience in this Palm Harbor fully furnished two-bedroom, two-bath home located within the highly desirable Venture Out Community. This immaculate home is nestled around tropical landscaping with a relaxing patio out back. Step into the open concept living room and well-equipped eat-in kitchen, featuring a full line of new

Kim Babenzien Expert Realty LLC (HQ)

701 Spanish Main Dr Unit 635, Cudjoe Key, FL 33042
/31
$759,000
- 3 Beds
- 2 Baths
- 1,364 Sq Ft
27235 Mariposa Rd, Summerland Key, FL 33042

Welcome to your perfect Keys retreat--low-maintenance, move-in ready, and full of charm! This 3-bedroom, 2-bath home offers a spacious 1,364 sq ft layout plus a screened-in porch with peaceful canal and backyard views. Inside, you'll find tall ceilings, crown molding, and tile flooring throughout. The kitchen is well-appointed with stainless appliances and granite counters.Built to last with

Brent Bishop Internet Realty of the Florida Keys

27235 Mariposa Rd, Summerland Key, FL 33042
/42
$2,300,000
- 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
/32
$1,099,000
- 3 Beds
- 2 Baths
- 1,392 Sq Ft
17137 Bonita Ln W, Summerland Key, FL 33042

Enjoy this ideal custom built Keys home located in beautiful Sugarloaf Shores! A very welcoming home with 3 bedrooms, 2 baths and a lovely enclosed porch with a captivating tong and groove ceiling. Attractive wood flooring throughout the living room, dining area and bedrooms with tile in the kitchen and baths. Two solid wide staircases lead up to the main entrance and another descending to

Tommy Gomez Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key

17137 Bonita Ln W, Summerland Key, FL 33042
/15
$285,000
- Land
701 Spanish Main Dr Unit 147, Cudjoe Key, FL 33042

Spacious RV lot with nightly rentals allowed. 35' x 69' RV lot offers ample space for your outdoor living. Venture Out is a 24hr manned gated community with amentities including - Boat Ramp and fueling station, Marina store. Tennis, Pickleball, Bocce, Basketball courts and a playground for the little ones. This golf cart friendly and beautifully maintained property is the perfect balance of

Jenifer Hirsch Bluescape Real Estate

701 Spanish Main Dr Unit 147, Cudjoe Key, FL 33042
/18
$1,150,000
- 3 Beds
- 2 Baths
- 1,544 Sq Ft
715 Caribbean Dr E, Summerland Key, FL 33042

Take advantage of a rare lease-to-own opportunity!Experience the ultimate boater’s lifestyle in this premier waterfront retreat, nestled in the exclusive Summerland Key Cove community. This ground-level 3-bedroom, 2-bath home offers 2,246 sq ft of comfortable living space, featuring impact-resistant windows and a canal front with deep-water access. Enjoy seamless access to both the Atlantic

Yohane Carcases Compass Florida, LLC.

715 Caribbean Dr E, Summerland Key, FL 33042
/35
$875,000
- 2 Beds
- 2 Baths
- 948 Sq Ft
22878 Privateer Dr, Summerland Key, FL 33042

Adorable 2 bed, 2 bath home with many new improvements! New impact windows and doors, new hardie-board siding installed on exterior of house, newer 60 foot concrete dock with cut-ins for a boat lift, roof replaced in October 2017 and newer hot water heater. All the heavy lifting has been done on this house located in sought after Cudjoe Key. Quick boating access to the Gulf and Atlantic,

Pamela Stangler Expert Realty LLC

22878 Privateer Dr, Summerland Key, FL 33042
/2
$65,000
- Land
0 Bk 2 Lt 24 Windward Beach Estate Unit 615586, Little Torch Key, FL 33042

ROGO lot worth 2 points for DEDICATION purposes. Seller has county ROGO Letter of Land Dedication verifying lot is eligible for land dedication/2 points. Want to build quicker? This is a path. Buyer to verify points and process with Monroe County. See Documents tab for letter.

Donna Pezzi Keller Williams Key West Compass Realty

0 Bk 2 Lt 24 Windward Beach Estate Unit 615586, Little Torch Key, FL 33042
/40
$344,999
- 2 Beds
- 1 Bath
- 720 Sq Ft
701 Spanish Main Dr Unit 625, Cudjoe Key, FL 33042

Step in to your new tropical paradise! This cozy 2 bedroom, 1 bathroom mobile home in Cudjoe Key offers affordable keys living. Enjoy all of the amenities that come with being located in the well known Venture Out community. Venture Out is an individual owned residential condominium community with 24 hour gated security, located only 19 miles from the vibrant city of Key West! Parking for one

Kim Babenzien Expert Realty LLC (HQ)

701 Spanish Main Dr Unit 625, Cudjoe Key, FL 33042
/37
$965,000 Open Fri 11AM - 1PM
- 2 Beds
- 2 Baths
- 912 Sq Ft
681 W Indies Dr, Summerland Key, FL 33042

This charming 2-bedroom, 2-bath home is your slice of paradise in the Lower Keys. Nestled on the open water, the property offers ocean views that will take your breath away. Enjoy your morning coffee or evening cocktails on the screened-in porch, perfect for relaxing and soaking in the coastal breeze. With a swim dock right out back, you'll have easy access to the crystal-clear waters for a

Karen Haack Coldwell Banker Schmitt RE Co. Lower Keys Office

681 W Indies Dr, Summerland Key, FL 33042
/39
$625,000
- 4 Beds
- 2 Baths
- 864 Sq Ft
27213 Old State Road 4a Unit 4a, Summerland Key, FL 33042

Private Solar-Powered Oasis in the Heart of Ramrod Key!Welcome to your tropical retreat in the Lower Keys! This spacious 4-bedroom, 2-bathroom home offers privacy, sustainability, and island living at its best--nestled quietly behind Boondocks on Ramrod Key with no immediate neighbors.Enjoy your own fenced backyard, perfect for kids, pets, or entertaining, plus large raised growing bins ready for

Michele Adams Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys

27213 Old State Road 4a Unit 4a, Summerland Key, FL 33042
/44
$997,000
- 2 Beds
- 2 Baths
- 779 Sq Ft
701 Spanish Main Dr Unit 214, Cudjoe Key, FL 33042

Welcome to your own piece of paradise in the heart of Cudjoe Key located in the gated community of Venture Out, where the island breeze and good vibes never stop!Live the island life in this turnkey 2 Bedroom, 2 Bath open water gem that's fully furnished and ready to rock your flip-flops off! Kick back on the oversized covered porch upstairs and catch the cool ocean vibes - it's your front-row

Kelly Gardner Bluescape Real Estate

701 Spanish Main Dr Unit 214, Cudjoe Key, FL 33042
/56
$295,000
- 1 Bed
- 1 Bath
- 368 Sq Ft
701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042

Welcome to this well-maintained home located in the desirable all-age community of Venture Out on Cudjoe Key. This home offers more than meets the eye, featuring a spacious addition that includes a carpeted living area and a versatile flex room currently used as an extra sleeping space--ideal for guests or a home office.While the exterior is modest, the inside offers a comfortable, well-kept

Kimberly Didrichsons Bluescape Real Estate

701 Spanish Main Dr Unit 533, Cudjoe Key, FL 33042
/35
$699,000
- 3 Beds
- 2 Baths
- 1,077 Sq Ft
28212 Gato Rd, Summerland Key, FL 33042

NATURE LOVERS PARADISETucked away in the heart of the Lower Keys, this unique property on Little Torch Key offers the ultimate in privacy and natural beauty. Surrounded by lush native vegetation and thriving wildlife, this home is a tranquil haven for those seeking peace and quiet -- a true escape from the everyday.Set on a generously sized lot, the home is bordered by mature tropical foliage

Donna Pezzi Keller Williams Key West Compass Realty

28212 Gato Rd, Summerland Key, FL 33042
/60
$539,000
- 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

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

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