Homes for Sale in Monroe County FL with 5-Bedrooms

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  /79

  $2,990,000

  • 6 Beds
  • 4 Baths
  • 3,047 Sq Ft

  901 46th St, Marathon, FL 33050

  Wake up to endless Gulf views and fall asleep to breathtaking sunsets at this rare waterfront estate.Tucked away at the end of a quiet road, this unique multi-family property sits directly on the Gulf, offering unmatched privacy, open water views, and direct boating access. Whether you're looking for a dream home, vacation getaway, or income-producing investment, this property delivers it all.The

  Bonnie Sanderson Florida Keys Real Estate Group

  901 46th St, Marathon, FL 33050
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  /55

  $24,995,000

  • 7 Beds
  • 10.5 Baths
  • 10,182 Sq Ft

  82719 Old Hwy, Islamorada, FL 33036

  Experience unparalleled oceanfront living at the Chateau On The Ocean, a turnkey private estate set within an exclusive enclave in Islamorada. Here elevated coastal living reflects the sophistication of what has been referred to as the Hamptons of Miami. From the moment you arrive, a striking sense of privacy, scale, and intention is evident, with architecture and surroundings that feel truly

  Pamela DiMartino Coldwell Banker Realty

  82719 Old Hwy, Islamorada, FL 33036
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  /61

  $1,950,000 Open Sat 11AM - 1PM

  • 5 Beds
  • 3 Baths
  • 2,146 Sq Ft

  530 White St, Key West, FL 33040

  Wonderful large home with a 7400 square foot yard!. Currently configured as 3 units, this property can be lived in as is or renovated for maximum potential. Located on the corner of White street and Stump lane, this property has beautiful grounds, room for a large pool, a workshop, decking, and off street parking. The First level features 2 units, each one has 2 bedrooms and 1 bath. Each unit is

  Elaine Coyle Keller Williams Key West Compass Realty

  530 White St, Key West, FL 33040
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  /44

  $15,950,000

  • 6 Beds
  • 7.5 Baths
  • 6,680 Sq Ft

  20 Avacado St, Islamorada, FL 33036

  BAYSIDE, DEEP WATER, BREATHTAKING GULF VIEWSWelcome to one of Islamorada's premier rare bayside estate properties - a remarkable parcel that stretches from Overseas Highway all the way to the Bay. The home bestows privacy, unobstructed Gulf Views, and a deep-water basin for calm dockage cable of accommodating substantial vessels with immediate access to world class sportfishing waters.The

  Steven Koleno Beycome of Florida, LLC

  20 Avacado St, Islamorada, FL 33036
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  /53

  $2,075,000

  • 5 Beds
  • 3 Baths
  • 3,234 Sq Ft

  320 5th St, Key Colony Beach, FL 33051

  Spacious and sophisticated waterfront home situated on a wide canal with desirable eastern exposure, offering serene views of the in-ground pool and 100-foot-wide canal. Designed for both entertaining and everyday comfort, the home features a covered patio on the lower level and a generous wooden deck on the upper level, connected by elegant spiral stairs leading to a dedicated entertainment area

  Baris Leyla Coastal Collection Real Estate Inc.

  320 5th St, Key Colony Beach, FL 33051
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  /2

  $1,300,000

  • 7 Beds
  • 5 Baths
  • 2,957 Sq Ft

  2016 Roosevelt Dr, Key West, FL 33040

  Builder/Contractors Dream ! Rare 4 unit new development opportunity, 7,000 square ft lot available in Midtown Key West.

  Richard Weston Weston Premier Realty, Inc

  2016 Roosevelt Dr, Key West, FL 33040
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  /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
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  /53

  $3,995,000

  • 5 Beds
  • 3 Baths
  • 2,640 Sq Ft

  105 Palo de Oro Dr, Islamorada, FL 33036

  Waterfront pool home with dockage in Venetian Shores offered furnished. Experience the ultimate Florida Keys lifestyle in this beautifully updated canal-front residence designed for relaxed coastal living and effortless entertaining. The home offers 5 bedrooms and 3 bathrooms, with approximately 2,640 square feet of living space, including 3 bedrooms and 2 bathrooms upstairs totaling

  Jamie Engel Coldwell Banker Schmitt Islamorada

  105 Palo de Oro Dr, Islamorada, FL 33036
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  /140

  $5,995,000

  • 5 Beds
  • 4.5 Baths
  • 4,660 Sq Ft

  90 Tingler Ln, Marathon, FL 33050

  Private oceanfront estate behind the gates of Tingler Island, one of Marathon's most exclusive and sought-after communities. Designed in timeless Caribbean West Indies style, this exceptional residence is perfectly oriented with coveted southern exposure--capturing refreshing ocean breezes, warm natural light, and the rare privilege of both sunrise and sunset views over open water.Set along a

  Nate Bartlett Berkshire Hathaway HomeServices Keys Real Estate

  90 Tingler Ln, Marathon, FL 33050
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  /65

  $5,750,000

  • 6 Beds
  • 6 Baths
  • 3,751 Sq Ft

  906 Johnson St, Key West, FL 33040

  Experience the grandeur of this exceptional six bedroom, five and a half bath estate located on one of the most exclusive streets in Key West. A stunning wall of bougainvillea and the stately front porch welcome you to this 3,751 square foot property on an expansive 10,750 square foot lot that embodies historic Key West architecture. The main residence features four bedrooms, three and half baths

  Regan Butler Truman & Co. (KW)

  906 Johnson St, Key West, FL 33040
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  /45

  $999,000

  • 5 Beds
  • 3 Baths
  • 2,912 Sq Ft

  34 Seagate Blvd, Key Largo, FL 33037

  Tropical retreat on the ocean side of Key Largo offering over 2,900 SF of air-conditioned living space. This solid concrete and rebar residence features 5 bedrooms, 3 spacious full baths, garage, two balconies, and a large patio terrace. Designed with soaring 10-13 ft ceilings throughout, the home includes 24 hurricane-impact doors and windows, metal roof, and is built above flood level.

  Richard Feldman Miami Waterfront Realty, LLC

  34 Seagate Blvd, Key Largo, FL 33037
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  /94

  $3,500,000

  • 5 Beds
  • 4 Baths
  • 3,060 Sq Ft

  17249 Bonefish Ln E, Sugarloaf Key, FL 33042

  Experience the ultimate island lifestyle in this breathtaking waterfront residence located in the prestigious Sugarloaf Shores subdivision. Situated on a massive 25,482 sq. ft. lot, this property offers rare privacy with plenty of room to breathe.Built with solid CBS construction, this 5-bedroom, 4-bath home is designed to capture the beauty of its surroundings. The open living space and

  Daniel Urban Expert Realty LLC (HQ)

  17249 Bonefish Ln E, Sugarloaf Key, FL 33042
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  /6

  $899,000

  • 5 Beds
  • 2 Baths
  • 1,501 Sq Ft

  1432 Eliza St, Key West, FL 33040

  EXCELLENT OPPORTUNITY! EXCELLENT LOCATION!This duplex offers several terrific options for the buyer -- from building a brand new home in a prime location to a top to bottom renovation project. In either case, you could choose to make it your own, or make it an income producing investment by living in one side and renting out the other or even renovating it to sell. Additionally, this property

  Ralph Sanchez Century 21 All Keys Inc (KW)

  1432 Eliza St, Key West, FL 33040
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  /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
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  /91

  $3,895,000

  • 7 Beds
  • 7.5 Baths
  • 3,015 Sq Ft

  919 Thomas St, Key West, FL 33040

  Charming Single family home with multiple guest cottages in Historic Key West, Florida. Discover the allure of old historic Key West with this exceptional compound, perfectly situated in a vibrant neighborhood. This property offers a unique blend of charm and modern comfort, making it an ideal investment or family retreat. The compound consists of 4 units, each exuding the distinctive character

  Richard Lively Coldwell Banker Schmitt Real Estate Co. (KW)

  919 Thomas St, Key West, FL 33040
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  /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
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  /60

  $4,995,000

  • 5 Beds
  • 6.5 Baths
  • 5,281 Sq Ft

  251 S Ocean Shores Dr, Key Largo, FL 33037

  Experience breathtaking 180-degree, unobstructed views of the Atlantic Ocean from this exceptional Key Largo oceanfront home, complete with a deeded 50' boat slip just steps away and within view. This spacious, turnkey residence features wraparound floor-to-ceiling windows and sleek invisible glass railings, seamlessly framing the ocean from most rooms.Offering 5 bedrooms and 6.5 bathrooms, this

  Claire Johnson Coastal Realty of the Florida Keys

  251 S Ocean Shores Dr, Key Largo, FL 33037
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  /72

  $16,900,000

  • 6 Beds
  • 6.5 Baths
  • 3,862 Sq Ft

  95410 Overseas Hwy, Key Largo, FL 33037

  Escape to your own tropical paradise with this dreamy, ultra-luxurious 6-acre estate on Key Largo Bay, just one hour south of Miami. This extraordinary private retreat features a main residence w/in-law suite, plus three accessory dwelling units, offering a total of 6 bedrooms, 6 full bathrooms, and 1 half baths, perfect for hosting family and friends or creating a secluded personal sanctuary.

  Alexander Sepkowski Better Homes & Gdns RE Fla 1st

  95410 Overseas Hwy, Key Largo, FL 33037
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  /73

  $1,099,000

  • 5 Beds
  • 2 Baths
  • 1,888 Sq Ft

  3836 No Name Rd, Big Pine Key, FL 33043

  Introducing No Name Retreat - Rare waterfront opportunity with exceptional development potential featuring 140 feet of direct water frontage and expansive 14,420 sq ft lot. The property currently includes a full duplex plus an additional buildable vacant lot, offering endless possibilities for investors, builders, or someone looking for extra room next door. Live on the water while generating

  Saara Staten Engel & Volkers Marathon

  3836 No Name Rd, Big Pine Key, FL 33043
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  /129

  $6,200,000

  • 5 Beds
  • 6 Baths
  • 3,000 Sq Ft

  24200 Overseas Hwy, Summerland Key, FL 33042

  Welcome to an unparalleled coastal lifestyle, where modern luxury meets the ultimate boater's paradise. This extraordinary compound, nestled along a prime stretch of the Florida Keys waterfront, has been completely reimagined for the discerning owner who demands both sophisticated living spaces and robust functionality. This pristine oceanfront estate is situated on a manicured one-acre gated

  Sylvia Werling Keller Williams Key West Compass Realty

  24200 Overseas Hwy, Summerland Key, FL 33042
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  /55

  $3,595,000

  • 6 Beds
  • 4 Baths
  • 3,333 Sq Ft

  820 12th St, Key Colony Beach, FL 33051

  Luxurious waterfront home offering sweeping views of Shelter Bay and 75 feet of deep-water (5 ft) dockage with direct ocean or Gulf access via Vaca Cut, just minutes to open water, a true boater's delight. Custom built by D'Asign Source, this six-bedroom 3.5-bath residence spans over 3,300 square feet and comes fully furnished (with select seller exclusions), making it ideal as a turnkey vacation

  Ea Ruth Loffreno Real Estate

  820 12th St, Key Colony Beach, FL 33051
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  /57

  $1,599,000

  • 5 Beds
  • 5 Baths
  • 2,952 Sq Ft

  426 Calle Limon, Marathon, FL 33050

  High-performing vacation rental located in the highly sought-after Sombrero Beach neighborhood, just a short walk to the beach. This fully furnished, turnkey property offers immediate income potential while also delivering an exceptional Keys lifestyle -- truly a home that checks every box.Featuring 5 bedrooms and 5 bathrooms, the residence is thoughtfully designed for both guests and owners,

  Sam Williams Coldwell Banker Schmitt Real Estate Co.

  426 Calle Limon, Marathon, FL 33050
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  /57

  $14,495,000

  • 7 Beds
  • 8 Baths
  • 7,358 Sq Ft

  44 Card Sound Rd, Key Largo, FL 33037

  Coastal elegance meets modern luxury in this newly built estate offering 7,358 SF under A/C plus over 2,800 SF of covered outdoor living. Featuring 7 bedrooms and 8.5 baths, the light-filled open floor plan showcases high-end finishes and exceptional craftsmanship throughout. Enjoy an elevator, chef's kitchen with designer cabinetry and premium appliances, two expansive living rooms (upstairs and

  Olga Grant Swenson & Ecuyer Realty

  44 Card Sound Rd, Key Largo, FL 33037
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  /91

  $12,450,000

  • 5 Beds
  • 6.5 Baths
  • 5,390 Sq Ft

  301 Ixora St, Duck Key, FL 33050

  Welcome to Villa Splendida in exclusive Duck Key, Florida. This custom built estate has been curated from the gated entrances to the 180' of protected ocean front dockage. Featuring a classic Mediterranean styling the spacious grounds host a variety of mature tropical plantings, fruit trees, and ease of maintenance turf throughout. The home itself is spacious and comfortable allowing elegant flow

  Lynn Lucas Berkshire Hathaway HomeServices Keys Real Estate

  301 Ixora St, Duck Key, FL 33050
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  /62

  $3,800,000

  • 5 Beds
  • 3 Baths
  • 2,464 Sq Ft

  87950 Overseas Hwy, Islamorada, FL 33036

  Tired of waiting on Uber or Freebee? Why not make this stunning bayfront estate your own private slice of paradise, right in the heart of Islamorada? Just a flip-flop stroll away from local favorites like MEAT Eatery, Shima, Marker 88, and City Hall Cafe, this property places you at the vibrant core of island living. Behind its private, fully fenced grounds, you'll discover sweeping bay views and

  Alina Davis Coldwell Banker Schmitt Islamorada

  87950 Overseas Hwy, Islamorada, FL 33036
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  /18

  $3,999,999

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

  17229 Oleander Ln, Summerland Key, FL 33042

  Modern luxury seamlessly blends with relaxed tropical living in this oversized, brand-new construction home located on Sugarloaf Key. This elevated three-story residence features 5 bedrooms and 5 bathrooms all en suite, offering approximately 3,700 square feet of thoughtfully designed living space on a 10,000-square-foot lot. Designed with both lifestyle and functionality in mind, the home

  Justyn Ewald Expert Realty LLC (HQ)

  17229 Oleander Ln, Summerland Key, FL 33042
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  /11

  $1,175,000

  • 8 Beds
  • 4 Baths
  • 2,780 Sq Ft

  500 22nd Street Ocean Unit 1-4, Marathon, FL 33050

  Seller Financing Available! Attention investors and business owners: This four-unit apartment building presents a compelling opportunity in the heart of the Florida Keys, offering immediate income with long-term strategic value. Each of the four units features a comfortable two-bedroom, one-bath layout, with long-term tenants currently in place, providing stable cash flow from day one. Each

  Sam Williams Coldwell Banker Schmitt Real Estate Co.

  500 22nd Street Ocean Unit 1-4, Marathon, FL 33050
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  /47

  $2,290,000

  • 5 Beds
  • 4 Baths
  • 2,366 Sq Ft

  1519 Johnson St, Key West, FL 33040

  Discover the perfect blend of modern elegance and island charm in this updated 5-bedroom, 4-bathroom Key West retreat. Just blocks from the beach and moments from the vibrant energy of Duval Street, this fully furnished home is ideal for full-time residency or a high-performing investment property. Step inside to an inviting open floor plan featuring gorgeous gray-blue tile flooring and a stylish

  Lisa Frins Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

  1519 Johnson St, Key West, FL 33040
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  /53

  $2,375,000

  • 5 Beds
  • 4 Baths
  • 2,772 Sq Ft

  205 S Point Dr, Summerland Key, FL 33042

  Experience elevated waterfront living at this stunning South Point Sugarloaf Key retreat, where open-water serenity meets refined island design. This exceptional five-bedroom, four-bathroom residence is thoughtfully designed to host family and guests with ease, featuring a desirable split-floor plan and expansive living spaces framed by endless turquoise views.The primary suite is a private

  Dawn McComish Lokation Real Estate

  205 S Point Dr, Summerland Key, FL 33042
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  /38

  $5,995,000

  • 5 Beds
  • 7 Baths
  • 4,387 Sq Ft

  910 Watson St, Key West, FL 33040

  More than a residence and rarer than legend, 910-914 Watson Street stands as one of the most iconic private estates in all of Key West--a once-in-a-generation offering where historic gravitas, tropical scale, and modern refinement converge behind gated walls in the heart of Old Town. Just moments from Truman Waterfront Park and beloved local favorites such as 5 Brothers Coffee and Cafe Sole, this

  Team Kaufelt Truman & Co. (KW)

  910 Watson St, Key West, FL 33040
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  /48

  $2,275,000

  • 5 Beds
  • 4 Baths
  • 3,132 Sq Ft

  321 Calzada de Bougainvillea, Marathon, FL 33050

  Spacious, two-level single family within walking distance to beautiful Sombrero Beach. Five bedrooms, high ceilings, marble baths. Screened in pool, roof top deck perfect for sunsets, star gazing, sunbathing, and watching the July 4th fireworks! Active vacation rental. 100 ft of water frontage on approximate 100 ft wide canal with shore power for boats. Two tiki seating areas, fish cleaning

  Bonnie Sanderson Florida Keys Real Estate Group

  321 Calzada de Bougainvillea, Marathon, FL 33050
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  /4

  $6,200,000

  • 5 Beds
  • 5 Baths
  • 4,624 Sq Ft

  36 Cannon Royal Dr, Big Coppitt Key, FL 33040

  Don't miss this rare and exceptional opportunity to have your dream waterfront masterpiece begin construction in 2026! Located in the prestigious, gated community of Shark Key, 36 Cannon Royal is an extraordinary west-facing lot that spans nearly 14,500 square feet and boasts approximately 130 feet of waterfront, delivering breathtaking sunset views over the Gulf waters. The sale of this property

  Brenda Donnelly Brenda Donnelly Real Estate LLC

  36 Cannon Royal Dr, Big Coppitt Key, FL 33040
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  /74

  $2,199,000

  • 6 Beds
  • 5 Baths
  • 2,570 Sq Ft

  1609 United St, Key West, FL 33040

  This versatile 3-family property offers a rare blend of privacy & income potential. Designed as 3 distinct residences, each with a private entrance and it's own kitchen and w/d, the property is ideal for an owner-occupant seeking rental income or an investment for long term, vacation rentals or family compound. Main Level - Primary Residence: The spacious downstairs layout features a 2 bed, 2

  Tammy Stiles Berkshire Hathaway HomeServices Knight & Gardner Realty

  1609 United St, Key West, FL 33040
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  /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
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  /16

  $1,089,000

  • 5 Beds
  • 2 Baths
  • 1,976 Sq Ft

  16 Shoreland Dr, Key Largo, FL 33037

  A amazing 5 bedroom 2 Bath solid concrete home, including the roof overlooking Largo Sound, in Key Largo, Florida! Updated Kitchen and Baths, new appliances and more. The corner lot is Zoned SC a rarity to find, and allows for a daily rentals, requires special licensing, we can help with that. Directly across the street is water access, for swimming, fishing, sun bathing, kayaking. Walk on over

  Larry Roth The Keyes Company

  16 Shoreland Dr, Key Largo, FL 33037
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  /75

  $3,350,000

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

  580 & 590 10th St, Key Colony, FL 33051

  Exceptional canal-front opportunity with proven income potential. This expansive 7-bedroom, 7-bath residence offers outstanding flexibility as a legal duplex with an interior lockout, allowing it to function seamlessly as a large single-family home or as two separate living spaces. The configuration includes a generous 5BR/4BA main residence paired with a private 2BR/2BA guest wing, topped off by

  Nate Bartlett Berkshire Hathaway HomeServices Keys Real Estate

  580 & 590 10th St, Key Colony, FL 33051
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  /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
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  /25

  $4,995,000

  • 5 Beds
  • 5 Baths
  • 4,822 Sq Ft

  112 N Bounty Ln, Key Largo, FL 33037

  Beautifully designed and built for comfort and function, this 5-bedroom, 5-bathroom + office home offers 4,822 sq. ft. of living space with porcelain tile floors, marble bathrooms and 8' doors throughout. The property is fully fenced with two electric gates, an intercom system and a 3-car garage plus a covered car porch. The lower-level enclosure is legal and adds valuable flexibility. The entry

  Courtney Conley Serhant Florida LLC - Coconut Grove

  112 N Bounty Ln, Key Largo, FL 33037
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  /88

  $5,950,000

  • 6 Beds
  • 8 Baths
  • 4,094 Sq Ft

  723 Eaton St, Key West, FL 33040

  This unique three residence property is ideally located just steps from the Historic Seaport and Fausto's grocery store in the heart of Old Town. A newly constructed building offers a spacious 3-bedroom, 3.5-bath main residence overlooking the pool, with a generous 2-bedroom, 2.5-bath apartment above. At the front of the property, a charming 1-bedroom, 1-bath home features a large garden with

  Kirksten Irick Preferred Properties (KW)

  723 Eaton St, Key West, FL 33040
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  /21

  $1,379,000

  • 6 Beds
  • 3 Baths
  • 2,434 Sq Ft

  1401 5th St, Key West, FL 33040

  Rare Opportunity: Three Charming Homes on Adjacent Lots - Unlimited Potential!Discover the perfect investment opportunity with these three vintage 2-bedroom, 1-bathroom homes, nestled on separate adjoining lots and being sold together as a single package. Situated in a desirable location, this unique offering provides incredible flexibility for visionary buyers.Each home offers cozy layouts that

  Stacy Stahl Realty ONE Group Destination

  1401 5th St, Key West, FL 33040

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