Key West, FL Homes for Sale with Pool

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  $5,495,000

  • 5 Beds
  • 5.5 Baths
  • 3,219 Sq Ft

  735 50 St Gulf Marathon, Key West, FL 33050

  “Discover Sunset Paradise – a stunning new construction Gulf-front retreat built in 2023 in the heart of Marathon, Florida Keys. This turnkey, fully furnished single-family home offers approximately 3,219 square feet of luxurious living space on a spacious 0.43-acre lot with direct open-water Gulf access.Boasting 5 bedrooms and 4.5 bathrooms (main house plus a separate guest cabana with

  735 50 St Gulf Marathon, Key West, FL 33050
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  /40

  $2,525,000

  • 4 Beds
  • 3 Baths
  • 2,051 Sq Ft

  1427 Washington St, Key West, FL 33040

  Set on a quiet, tree-lined block in one of Key West's most sought-after residential pockets, this thoughtfully reimagined 4BD/3BA residence offers just over 2,000 square feet of refined island living -- the result of a multi-year renovation where no detail was overlooked. The first floor opens to a flexible bedroom or private office alongside a full bath, newly converted and finished to the same

  The Spottswood Team Truman & Co. (KW)

  1427 Washington St, Key West, FL 33040
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  /57

  $2,919,000

  • 3 Beds
  • 4 Baths
  • 3,461 Sq Ft

  3615 Eagle Ave, Key West, FL 33040

  Some homes in Key West give you a view. This one gives you an entire private world.Tucked behind its own gates on a lush 12,000-square-foot lot, 3615 Eagle Avenue is a custom-built retreat where a botanical garden isn't a backyard feature -- it's the whole point. Mature native palms, flowering tropical plants, and a resident population of birds and butterflies surround the home on every

  Suzanne Moore Suzanne Moore Real Estate

  3615 Eagle Ave, Key West, FL 33040
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  $2,549,000

  • 3 Beds
  • 4 Baths
  • 2,469 Sq Ft

  2924 Riviera Dr, Key West, FL 33040

  **Seller Financing Considered** 2924 Riviera Dr is a Must See! Meticulously renovated house on the Riviera Canal. Features 3 bedrooms, 2 full baths & 2 half baths, plus separate pool / canal side cottage. Open & airy living room & kitchen gives you spectacular views of backyard, pool and canal. You can even see the pool and canal from the front door. Owner / Seller is a carpenter. House was

  Walt Lee Berkshire Hathaway HomeServices Knight & Gardner Realty

  2924 Riviera Dr, Key West, FL 33040
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  /2

  $339,000

  • 2 Beds
  • 2 Baths
  • 784 Sq Ft

  5031 5th Ave, Key West, FL 33040

  A BOATER’S DREAM & KAYAKER’S PARADISE—JUST MINUTES FROM KEY WEST!Experience the ultimate Florida Keys lifestyle in the beautiful Sunset Harbor Waterfront Community, where it’s more than just a home—it’s a lifestyle! Boaters will love the convenience of community boat slips with Cow Key Channel just a 2-minute ride away, providing quick access to both the Atlantic Ocean and Gulf. Kayakers can

  Benton Langley Langley Knight Gardner Islamorada

  5031 5th Ave, Key West, FL 33040
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  /61

  $2,200,000

  • 5 Beds
  • 4 Baths
  • 2,096 Sq Ft

  1320 6th St, Key West, FL 33040

  Two Parcels Included!!! Welcome to 1320 6th Street, a fantastic investment opportunity in a prime midtown Key West location. This property features three private units, each offering great rental income potential. Your chance to make money and have a home in paradise. Newly remodeled kitchen in the rental home.Enjoy the large inviting pool and well-maintained grounds, all just minutes from

  Sarah Dolson Coldwell Banker Schmitt Real Estate Co. (KW)

  1320 6th St, Key West, FL 33040
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  /15

  $599,000

  5950 Peninsular Ave Unit 674, Key West, FL 33040

  Great opportunity to own a 60' x 20' deep-water boat slip in the highly sought-after Oceans Edge Resort & Marina on Stock Island. This premier marina offers approximately 8' controlled depth with easy access to both the Atlantic Ocean and the Gulf of Mexico. Owners enjoy access to the resort's exceptional amenities, including six swimming pools, a fitness center, open parking, a fuel dock, dog

  Keys Team Bryant and Kat Expert Realty LLC (HQ)

  5950 Peninsular Ave Unit 674, Key West, FL 33040
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  /45

  $2,249,000

  $51K PRICE DROP

  • 3 Beds
  • 4 Baths
  • 1,724 Sq Ft

  1109 Stump Ln, Key West, FL 33040

  On a quiet lane in Old Town, this classic Conch home offers a setting where life feels just a little slower and a lot more enjoyable. From the moment you step inside, the home draws you outward, where indoor living blends naturally with the surrounding outdoor spaces.The heart of the home is built around entertaining. The living area, kitchen, and dining space come together in a way that

  Terri Spottswood Truman & Co. (KW)

  1109 Stump Ln, Key West, FL 33040
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  /50

  $3,300,000

  • 4 Beds
  • 3.5 Baths
  • 2,573 Sq Ft

  214 Eanes Ln, Key West, FL 33040

  Welcome to 214 Eanes Lane, a classic Key West property offering flexibility, character, and exceptional investment potential in a prime Old Town location. Located in an X flood zone, this property offers added peace of mind and potential savings on insurance--an increasingly valuable feature in today's market.This unique property is configured as two separate units, featuring a main two-story

  Jaime Caballero Century 21 Prestige Realty Group (KW)

  214 Eanes Ln, Key West, FL 33040
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  /37

  $1,799,000

  • 3 Beds
  • 2.5 Baths
  • 1,456 Sq Ft

  2101 Harris Ave, Key West, FL 33040

  There is something special about a home where everything has already been done for you, and at 2101 Harris Avenue, all that is left is to move in and start enjoying it!Completely reimagined from top to bottom in 2025, this beautifully renovated Midtown East home feels fresh, welcoming, and ready for its next chapter. Set on a fully fenced corner lot with all new landscaping, the property

  The Spottswood Team Truman & Co. (KW)

  2101 Harris Ave, Key West, FL 33040
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  /40

  $5,400,000

  • 6 Beds
  • 6.5 Baths
  • 2,993 Sq Ft

  613 Margaret St, Key West, FL 33040

  Step back into timeless Key West soul, where leaf-stamped garden paths, sun-dappled outdoor showers, and the gentle trickle of private pool waterfalls create an unforgettable Old Town sanctuary. Hidden behind a classic wooden gate just moments from the Historic Seaport and Duval Street, this compound offers two private, fully equipped homes on a lush 7,796-sq. ft lot, providing the ultimate

  Brenda Donnelly Brenda Donnelly Real Estate LLC

  613 Margaret St, Key West, FL 33040
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  /37

  $2,250,000

  • 3 Beds
  • 3.5 Baths
  • 1,470 Sq Ft

  1300 Seminary St, Key West, FL 33040

  If you are seeking a private tropical backyard oasis look no further. This charming 2 story home is situated on a corner parcel in a quiet and peaceful mid town neighborhood. Behind the white picket fence, you will be welcomed to a great room with dramatic ceiling heights, wrapped with sliding glass doorwalls that open to over 500 square feet of covered porches. This home has been very well

  Wendy Zintsmaster Truman & Co. (KW)

  1300 Seminary St, Key West, FL 33040
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  /37

  $1,875,000

  $300K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,760 Sq Ft

  1115 Fleming St, Key West, FL 33040

  This rare Key West treasure hasn't changed hands in over a century, and it sits on the most coveted block in Old Town. A true time capsule waiting to be revived, it's the last of its kind not yet renovated--so you won't be buying someone else's overpriced remodel. Bring your imagination and restore this home to its original, sun-soaked beauty. There's not another lot like it in Old Town. The

  Derek Epperly, PA Keys Atlantic Realty

  1115 Fleming St, Key West, FL 33040
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  /34

  $1,375,000

  • 2 Beds
  • 2 Baths
  • 948 Sq Ft

  1216 Packer St, Key West, FL 33040

  Experience the charm and ideal location that make Old Town Key West so special. Located in the desirable X Flood Zone, this two-bedroom, two-bath home offers an inviting layout filled with classic island character. A wine refrigerator provides a convenient touch for entertaining or enjoying a chilled bottle at the end of the day. The outdoor space is a true highlight, featuring a spacious

  Tom Mclaughlin Coldwell Banker Schmitt Real Estate Co. (KW)

  1216 Packer St, Key West, FL 33040
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  /32

  $2,650,000

  • 3 Beds
  • 2 Baths
  • 2,038 Sq Ft

  1500 Atlantic Blvd Unit 414, Key West, FL 33040

  Life is BETTER at the Beach!Enjoy penthouse style living with panoramic ocean views from this two story oceanfront condo!This waterfront setting is simply serene, peaceful and beautiful! Floor to ceiling windows invite natural light, revealing the breathtaking water views from inside as well as the outdoor ocean facing deck - perfect for entertaining, lounging and absorbing

  Behmke The Compass Realty (KW)

  1500 Atlantic Blvd Unit 414, Key West, FL 33040
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  $2,500

  5950 Peninsular Ave Unit 640, Key West, FL 33040

  Prestigious boat slip for rent at Ocean's Edge Marina, suitable for boats up to 50FT located on the North pier with ample water access boasting a 6ft control depth. Features include a nearby fuel station and access to the hotel pool for tenants. Ideal for water enthusiasts seeking a premium marina experience. Daily, monthly or long term rentals available. Air bnb's or houseboats are not allowed.

  Hana Tomita Berkshire Hathaway HomeServices Knight & Gardner Realty

  5950 Peninsular Ave Unit 640, Key West, FL 33040
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  /20

  $239,000

  $20K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 420 Sq Ft

  55 Boca Chica Rd Unit 57, Key West, FL 33040

  Opportunity to enjoy the laid-back Florida Keys lifestyle in a secure, affordable setting, 1 bedroom, 1 bath. Located in the gated Seaside Resort on Big Coppitt Key, this well-maintained community is one of the Keys' best-kept secrets. Residents enjoy access to resort-style amenities, including two swimming pools, gym equipment, a clubhouse, a library/game room, and a marina. You can't beat the

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

  55 Boca Chica Rd Unit 57, Key West, FL 33040
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  /36

  $869,000

  • 2 Beds
  • 1 Bath
  • 680 Sq Ft

  620 Thomas St Unit 149, Key West, FL 33040

  Highly desirable first floor Shipyard condo. This 2 bedroom, one bath unit is located in the Shipyard condominiums in Truman Annex.Large rear deck offers room for that Key West lifestyle. Close to Duval Street and all the downtown and waterfront activities. Includes an assigned parking space and non-transient rental license allowing 28 days or more rentals.

  Behmke The Compass Realty (KW)

  620 Thomas St Unit 149, Key West, FL 33040
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  /13

  $225,000

  5555 College Rd Unit Dolphin 7, Key West, FL 33040

  Best wet slip deal in Key West for up to 35' x 15' boat. Gated secure marina community with Bellingham floating docks, plenty of parking, a clubhouse and pool.This slip keeps your boat out of the water and includes a $30,000 HARBOR HOIST BOAT LIFT.Immediately across marina is fuel dock and ship's store.Drive in and park your car, start up your boat and immediately enjoy ingress /

  Jerry Hughes Beach Club Brokers (KW)

  5555 College Rd Unit Dolphin 7, Key West, FL 33040
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  /3

  $45,000

  • 2 Beds
  • 3 Baths
  • 1,000 Sq Ft

  200 Sunset Ln Unit 534 Week 44, Key West, FL 33040

  Waterfront sunset views from Unit 534 at Hyatt Sunset Harbor! This desirable two-story, 2-bedroom, 3-bath residence features a full kitchen, spacious living area with additional sleeping accommodations, and an exceptional Week 44 ownership period that typically coincides with Key West's renowned Offshore Powerboat Racing World Championships. Enjoy resort amenities including a swimming pool, hot

  Connor Nelson Berkshire Hathaway HomeServices Knight & Gardner Realty

  200 Sunset Ln Unit 534 Week 44, Key West, FL 33040
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  $1,025,000

  • 2 Beds
  • 2 Baths
  • 1,311 Sq Ft

  1800 Atlantic Blvd Unit 427C, Key West, FL 33040

  This spacious two-bedroom, two-bath penthouse condo boasts a stunning balcony with ocean views, making it the perfect place to relax and enjoy the breathtaking scenery. The beautifully designed kitchen features a breakfast bar, granite countertops, and stainless steel appliances, making it a chef's dream come true. The stunning living room and dining room are flooded with natural light, creating

  Tommy Mack Coastal Collection Real Estate Inc.

  1800 Atlantic Blvd Unit 427C, Key West, FL 33040
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  $1,689,000

  $111K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  21 Bougainvillea Ave, Key West, FL 33040

  Boaters Paradise Seize-The-Day in a Key Haven waterfront home with immediate Gulf and Atlantic access just minutes from Key West. This rare boating property offers 62 feet of solid concrete seawall on a clean, free-flowing 100-foot-wide canal. Approximately a two-minute idle to open bay with no bridges and no restrictions -- true open-water access for larger vessels.Enjoy a remarkable

  Robin Nilsson Keller Williams Key West Compass Realty

  21 Bougainvillea Ave, Key West, FL 33040
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  $3,300,000

  • 3 Beds
  • 2 Baths
  • 1,782 Sq Ft

  728 Poor House Ln, Key West, FL 33040

  Old Town charm in the heart of Key West! This two-story Conch-style residence offers an exceptional opportunity to enjoy island living in the highly desirable Old Town Historic District. A two-car driveway provides convenient off-street parking, while a welcoming front porch leads into an inviting interior with wood floors throughout the first level.The well-appointed kitchen features a gas

  Fabiola Acevedo Realty 100

  728 Poor House Ln, Key West, FL 33040
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  /25

  $4,375,000

  New Construction $125K PRICE INCREASE

  • 5 Beds
  • 5.5 Baths
  • 4,103 Sq Ft

  231 E Shore Dr Unit 6, Key West, FL 33040

  Welcome home to an exceptional new-construction residence in a private, gated community offering resort-style amenities, a boat slip and nightly rental opportunities. Conveniently located next to Summerland Key Airport, this fully upgraded home features a private elevator, a stunning infinity pool overlooking the water and an expansive rooftop deck perfect for enjoying breathtaking Florida Keys

  Stephanie Marinucci Serhant

  231 E Shore Dr Unit 6, Key West, FL 33040
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  /74

  $2,199,000

  $100K PRICE DROP

  • 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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  /40

  $2,599,000

  • 3 Beds
  • 2 Baths
  • 1,204 Sq Ft

  812 Carsten Ln, Key West, FL 33040

  Welcome to a stunning transformation of a perfectly located Old Town home. Restored from the ground up to create a single level dream home totaling 3bd/2ba overlooking a beautiful pool and patio. Enjoy an open floor plan where the kitchen is truly the heart of the home complete with top of the line stainless Thermador appliances, quartz countertops and timeless cabinetry with a central island

  Wendy Zintsmaster Truman & Co. (KW)

  812 Carsten Ln, Key West, FL 33040
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  /69

  $1,490,000

  Open Sat 11AM - 1PM

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

  1724 Rose St, Key West, FL 33040

  Welcome to 1724 Rose Street, a spacious single-family home on a generous corner lot in a quiet Midtown neighborhood, close to Key West's beautiful beaches.The main level features an inviting open-concept kitchen, dining, and living area, along with three bedrooms and two baths. Freshly painted inside and out, the home is move-in ready while offering an opportunity to add your own personal

  Ellen Gvili Ocean Sotheby's International Realty

  1724 Rose St, Key West, FL 33040
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  /39

  $1,799,765

  • 3 Beds
  • 3 Baths
  • 1,502 Sq Ft

  1523 Seminary St, Key West, FL 33040

  Discover the perfect blend of island charm, comfort, and versality in this exceptional Key West property featuring a main residence and a spacious guest house. The main home offers 2 bed, and 2 baths thoughtfully designed with bright, open living space and classic Key West character. Added value is the separate guest house featuring an open concept floor plan, a beautiful bathroom, with open

  Christine EckArt Berkshire Hathaway HomeServices Knight & Gardner Realty

  1523 Seminary St, Key West, FL 33040
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  /16

  $392,000

  $178K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,100 Sq Ft

  3314 Northside Dr Unit 46, Key West, FL 33040

  This is a SHORT SALE and is subject to lender approval.Opportunity for you to have an island of Key West lifestyle! Whether a primary home or investment, this condo should be on your list -- great location, multi-level living, and covered deeded parking. Located near the center of the island conveniently located close to shopping plazas, movie theater, schools and dining as well as being just

  Gwendolyn Esbensen Berkshire Hathaway HomeServices Knight & Gardner Realty

  3314 Northside Dr Unit 46, Key West, FL 33040
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  /42

  $4,450,000

  $145K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 2,985 Sq Ft

  1113 Stump Ln, Key West, FL 33040

  Experience the ideal blend of historic charm and modern luxury in this fully renovated and expanded Key West residence, where no detail has been overlooked. Set on a quiet, one-way street in Old Town, this 4-bedroom, 4.5-bath home offers 2,985 square feet of thoughtfully designed living space. Inside, soaring cathedral ceilings and rich Dade County pine walls create a warm, timeless aesthetic.

  Terri Spottswood Truman & Co. (KW)

  1113 Stump Ln, Key West, FL 33040
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  /42

  $699,000

  $51K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,135 Sq Ft

  26D 11th Ave, Key West, FL 33040

  Positioned perfectly on a corner lot with ample outdoor space & private driveway. Welcome to D26 11th Avenue on Stock Island!This three (3) bedroom and two (2) bath home offers a great opportunity for buyers looking to upgrade into a new property, or those simply trying to get into homeownership. Recently renovated and completely fenced-in this home sits on a corner lot with room for a

  Bobby Coe RE/MAX Keys Connection (KW)

  26D 11th Ave, Key West, FL 33040
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  /80

  $6,750,000

  • 5 Beds
  • 4.5 Baths
  • 3,663 Sq Ft

  411 Louisa St, Key West, FL 33040

  Luxurious, Modern, Historic, & Impeccably Remodeled. Welcome to 411 Louisa Street, located in the heart of Old Town Key West, less than a block from Duval Street's top dining and entertainment.This stunning five-bedroom, four-and-a-half-bath residence offers 3,663 sq. ft. of living space on an 8,227 sq. ft.oversized lot, providing rare space and privacy in one of the island's most

  Bobby Coe RE/MAX Keys Connection (KW)

  411 Louisa St, Key West, FL 33040
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  /21

  $649,000

  • 1 Bed
  • 1 Bath
  • 626 Sq Ft

  806 Florida St Unit 5, Key West, FL 33040

  1 bedrooms and 1 bathrooms, you are going to enjoy the 626 sqft that composes this Condominium. Nested in an enjoyable neighborhood (the Meadows), and minutes from local attractions, restaurants, the waterfront, and public park.New washer/dryer, new ceiling fans, high ceilings, stainless steel appliances, tile floors, and an entry deck with hurricane-proof French doors.Plus a large,

  Steven Koleno Beycome of Florida, LLC

  806 Florida St Unit 5, Key West, FL 33040
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  /15

  $199,000

  5555 College Rd Unit 6, Key West, FL 33040

  Own your piece of paradise with Dolphin slip #6 at Sunset Marina, Key West! This deeded 30 foot boat slip is located in one of Key West's most desirable full service marinas, offering a protected harbor and quick access to both the Gulf and the Atlantic. This slip can accommodate vessels up to 35 feet, and includes dockside water and electric. It is located on the gated side of Sunset Marina,

  Laura Hipps Berkshire Hathaway HomeServices Knight & Gardner Realty

  5555 College Rd Unit 6, Key West, FL 33040
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  /47

  $1,500,000

  • 4 Beds
  • 3 Baths
  • 1,800 Sq Ft

  193 Golf Club Dr, Key West, FL 33040

  Located within the private Sanctuary enclave of the Key West Golf Club, this 4-bedroom, 3-bath residence offers rare privacy, coveted west-facing sunset exposure, and direct frontage along the 18th hole of the Rees Jones-designed course, all within the City of Key West.With approximately only 10 homes in the entire Key West Golf Club community offering 1,800 square feet or more of living

  Zachary Goodfellow Keller Williams Key West Compass Realty

  193 Golf Club Dr, Key West, FL 33040
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  $1,799,000

  $186K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,600 Sq Ft

  1011 Simonton St Unit 1, Key West, FL 33040

  Excellent opportunity whether looking for a private residence or an investment. This condo will not disappoint. Artfully renovated very spacious three story . Plenty of outside area including private courtyard with a heated pool. Walk out the front door and just steps away from Duval st. and everything Key West has to offer. This is maintenance free living while it gives the feeling of a private

  Marc Ulanowski Equestrian Sotheby's Internati

  1011 Simonton St Unit 1, Key West, FL 33040
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  /27

  $550,000

  5950 Peninsular Ave Unit 644, Key West, FL 33040

  Now known as Hilton Key West Resort & Marina - Best 50' Slip location in the Marina!...and Seller Financing possible.Rents well when not personally using the slip via on-site rental mgt program.Slip can handle a 51' x 21' boat nicely...Commercial charter or fishing operations okay.Enjoy all the amenities of this gated first class resort and marina to include: six pools, fitness

  Jerry Hughes Beach Club Brokers (KW)

  5950 Peninsular Ave Unit 644, Key West, FL 33040
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  /36

  $2,980,000

  $200K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,373 Sq Ft

  1019 Whitehead St, Key West, FL 33040

  PRICE IMPROVEMENT-Classic Key West charm and sophistication abound, with traditional grace yet modern conveniences, this wasn't just a simple remodel. This was a carefully thought out, complete and careful renovation of this Old Town treasure.This home is carefree, furnished, and turnkey-bring your personal bag and you are home immediately.A worry free and easily maintained 3

  Wade Meyer Real Estate Management of Key West, LLC

  1019 Whitehead St, Key West, FL 33040
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  /41

  $3,800,000

  • 3 Beds
  • 3 Baths
  • 1,933 Sq Ft

  619 Ashe St, Key West, FL 33040

  First time offered in more than 25 years, this beloved Old Town address presents a rare opportunity to own a complete compound on one of Key West's most private and premier streets. Located in the desirable X flood zone, the property features three bedrooms, three baths, and off-street parking for two vehicles. Rich in character and timeless Key West architecture, the home showcases beautifully

  Brenda Donnelly Brenda Donnelly Real Estate LLC

  619 Ashe St, Key West, FL 33040
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  /27

  $1,385,000

  $65K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,558 Sq Ft

  2313 Fogarty Ave, Key West, FL 33040

  There is almost nothing like this in Key West: a 2007-built home, raised from the ground up to modern standards. Rare, move-in ready, and free of the surprises that come with much older homes in town.Elevated above the floodplain, with impact windows and doors rated for 175 mph winds and a 16kW standby generator, this is a home built for real peace of mind, whether you are here year-round or

  Juan Benitez Benitez Keller Williams Key West Compass Realty

  2313 Fogarty Ave, Key West, FL 33040

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