Homes for Sale near Monroe County Detention Center

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  /48

  $3,299,000

  • 5 Beds
  • 3 Baths
  • 2,608 Sq Ft

  1420 White St, Key West, FL 33040

  Stunning Grand Key West Historic Home Newly Renovated into a Gorgeous Single Family Home with High Ceilings, Architectural Moldings, and Imported Tiles . This Home has undergone a Massive Transformation with the current owners paying great attention to New Spaces and Natural Light. There are so many possibilities to enjoy this Classic European Inspired Home. There are two Primary Suites, one on

  Lisa Lennon Berkshire Hathaway HomeServices Knight & Gardner Realty

  1420 White St, Key West, FL 33040
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  /45

  $3,200,000 Open Sun 12PM - 3PM

  • 5 Beds
  • 6 Baths
  • 2,760 Sq Ft

  1224 Florida St, Key West, FL 33040

  Nestled in a quiet Old Town neighborhood, this elevated three-story home blends timeless craftsmanship with contemporary design. Thoughtfully constructed for style and strength, 1224 Florida features five spacious bedrooms--each with its own en-suite bath--and an open, light-filled layout that flows seamlessly from indoors to out. The recently renovated chef's kitchen is equipped with premium

  Brenda Donnelly Brenda Donnelly Real Estate LLC

  1224 Florida St, Key West, FL 33040
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  /25

  $699,000

  • 3 Beds
  • 2 Baths
  • 1,104 Sq Ft

  317 Cross St, Key West, FL 33040

  This 3 bedroom, 2 bathroom home is a great family home or investment opportunity; situated on a large 5625 sf corner lot within walking distance of the neighborhood park. It is currently configured with the main section having 2 bedrooms, living area, kitchen and a full bathroom plus an adjoining guest section that has it's own living area, kitchen, bedroom, full bathroom and it's own separate

  Rob Severin Rob Severin Real Estate Co

  317 Cross St, Key West, FL 33040
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  /49

  $2,599,000

  • 4 Beds
  • 4 Baths
  • 1,854 Sq Ft

  1320 Eliza St, Key West, FL 33040

  Welcome to the School House on Eliza!1320 Eliza Street is a stunning corner-lot property that exudes old-world charm and proudly served as a historic schoolhouse in Key West.This four (4) bedroom with two (2) full bathrooms with two (2) half bathrooms home sits on a tropically landscaped corner lot with great outdoor living and a perfect heated pool. A brand new roof was just installed.The main

  Bobby Coe RE/MAX Keys Connection (KW)

  1320 Eliza St, Key West, FL 33040
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  /27

  $648,888

  • 3 Beds
  • 2 Baths
  • 1,050 Sq Ft

  3314 Northside Dr Unit 55, Key West, FL 33040

  Excellent Family Home or Investment Opportunity! Step into your new life in this beautifully elevated three-bedroom, two-bathroom home featuring new impact doors and windows, a for-year-old AC system, new kitchen, and a newer roof (only three years old with two years of warranty remaining). Bright and airy, the main floor is filled with natural light and positive energy, offering a spacious

  Yulia Vakhtenko Keys Top Realty LLC

  3314 Northside Dr Unit 55, Key West, FL 33040
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  /54

  $1,100,000

  • 5 Beds
  • 3 Baths
  • 1,488 Sq Ft

  2922 Flagler Ave, Key West, FL 33040

  With five bedrooms and three bathrooms, it seems perfect for families or hosting guests. The location ensures easy access to fantastic dining, coffee shops, and shopping, along with recreational options like sports venues and schools. The emphasis on beautiful finishes and an inviting floor plan suggests a luxurious yet comfortable living space, ideal for entertaining. Plus, the proximity to the

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

  2922 Flagler Ave, Key West, FL 33040
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  /19

  $2,095,000

  • 8 Beds
  • 4 Baths
  • 3,383 Sq Ft

  905 Grinnell St, Key West, FL 33040

  Located in the heart of Key West's Historic District, 905 Grinnell Street is a distinctive multi-unit property that blends architectural character with strong investment performance. Originally built as a church, the structure has been thoughtfully converted into four residential units totaling 3,383 square feet. Each unit is individually metered and currently leased, offering a stable and

  Team Kaufelt Truman & Co. (KW)

  905 Grinnell St, Key West, FL 33040
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  /35

  $1,949,000

  • 2 Beds
  • 3 Baths
  • 1,357 Sq Ft

  3841 N Roosevelt Blvd Unit 332, Key West, FL 33040

  Experience ultimate elegance at Key West's Beachside Resort & Residences! This third-floor Condominium offers the perfect blend of luxury, flexibility, and investment potential. Featuring two transient licenses and a lockout configuration, this property includes both a Signature King Room and a Resort View Suite, which can be used together or separately for optimal rental income.The Signature

  The Spottswood Team Truman & Co. (KW)

  3841 N Roosevelt Blvd Unit 332, Key West, FL 33040
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  /33

  $1,949,000

  • 2 Beds
  • 3 Baths
  • 1,357 Sq Ft

  3841 N Roosevelt Blvd Unit 315, Key West, FL 33040

  Experience ultimate elegance at Key West's Beachside Resort & Residences! This first-floor Condominium offers the perfect blend of luxury, flexibility, and investment potential. Featuring two transient licenses and a lockout configuration, this property includes both a Signature King Room and a Resort View Suite, which can be used together or separately for optimal rental income.The Signature

  The Spottswood Team Truman & Co. (KW)

  3841 N Roosevelt Blvd Unit 315, Key West, FL 33040
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  /12

  $859,500

  • 2 Beds
  • 2 Baths
  • 1,464 Sq Ft

  3711 Eagle Ave, Key West, FL 33040

  Located on the very desirable upper end of Eagle Avenue, this duplex offers a compelling opportunity in one of Key West's most sought-after residential neighborhoods. The main house is a full renovation project, ideal for those looking to customize or redevelop. A build-back letter from the City of Key West is in place, preserving the ability to rebuild and reimagine the property to suit your

  Terri Spottswood Truman & Co. (KW)

  3711 Eagle Ave, Key West, FL 33040
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  /3

  $859,500

  • Land

  3705 Eagle Ave, Key West, FL 33040

  Rare opportunity to own a vacant, buildable 6,000 sq ft lot in Key West's New Town neighborhood. Located on sought-after Eagle Avenue, and on one of the best blocks too, this prime residential parcel offers the chance to design and build a custom home in a well-established setting. Beneficial use allocation has already been granted by the City of Key West Planning Department, streamlining the

  Terri Spottswood Truman & Co. (KW)

  3705 Eagle Ave, Key West, FL 33040
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  /41

  $2,550,000

  • 3 Beds
  • 4 Baths
  • 1,818 Sq Ft

  1231 Washington St, Key West, FL 33040

  Prime Mid-Town location - walk or bike to White Street pier, Tennis and Pickle ball, and Higgs Beach. Spanning over 1800 square feet, This home is easy one level living, completely fenced, has multiple off street parking spaces- covered and uncovered, and a remote control entrance gate for parking. The Main home has 2 bedrooms, 2 full bathrooms,, an additional private jetted tub area and an

  Elaine Coyle Keller Williams Key West Compass Realty

  1231 Washington St, Key West, FL 33040
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  /43

  $949,999

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

  33D 11th Ave, Key West, FL 33040

  SHOWSTOPPER! This stunning home is filled with high-end details and thoughtful design. The chef's kitchen is a true centerpiece, featuring Viking appliances, Italian quartz countertops, and custom finishes that will inspire your inner gourmet. There is also an additional room with laundry that could be used for a bedroom, office or whatever you need it to be. Outdoors, the covered patio is built

  Michaele Meadows Ocean Sotheby's International Realty

  33D 11th Ave, Key West, FL 33040
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  /21

  $1,825,000

  • 2 Beds
  • 3 Baths
  • 1,959 Sq Ft

  1011 Truman Ave, Key West, FL 33040

  1011 Truman Avenue is a stylish mixed-use property located in the heart of Old Town, Key West. The building includes three legal units with one covered off street parking space and sits in the desirable X-Flood Zone. The ground floor features a 795 sq. ft. professional office space with an industrial feel and a half bath, along with a 416 sq. ft. one-bedroom unit that includes a full bathroom and

  Claude Gardner Berkshire Hathaway HomeServices Knight & Gardner Realty

  1011 Truman Ave, Key West, FL 33040
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  /38

  $2,400,000

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

  1109 Stump Ln, Key West, FL 33040

  Nestled on a tranquil lane in Old Town Key West, this classic Conch home is designed for relaxed island living. The property offers multiple entertainment spaces both indoors and out, with the expansive living area and kitchen opening to a great covered patio . Enjoy a large pool surrounded by spacious decks and lush landscaping for lounging and privacy. Inside, you'll find 3 bedrooms 2.5 baths

  Terri Spottswood Truman & Co. (KW)

  1109 Stump Ln, Key West, FL 33040
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  /58

  $3,295,000

  • 3 Beds
  • 4 Baths
  • 2,746 Sq Ft

  1126 von Phister St, Key West, FL 33040

  Beautiful. Historic. Ideal for Entertaining When you walk through the beautiful front door of this stunning two-story historic home, you will be amazed by the high ceilings, large open concept living area with original hardwood floors. High arches separate the entryway and the two different seating areas.Host all your gatherings in the large dining room that has a vaulted ceiling with wood

  Jody Clark Key West Luxury Real Estate Inc (KW)

  1126 von Phister St, Key West, FL 33040
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  /28

  $875,000

  • 2 Beds
  • 1 Bath
  • 1,292 Sq Ft

  2016 Fogarty Ave, Key West, FL 33040

  2016 Fogarty Avenue, Key WestMidtown 2/1 on a full 5,000 SF lot with great kitchen, rear deck, storage, and room for a pool. Wood floors, washer/dryer, easy layout, rising neighborhood near beaches & Old Town.

  Kirksten Irick Preferred Properties (KW)

  2016 Fogarty Ave, Key West, FL 33040
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  /47

  $2,999,999

  • 2 Beds
  • 4 Baths
  • 1,596 Sq Ft

  405 Petronia St, Key West, FL 33040

  Heart of Old Town Key West. Very rare FULLY RENTED income producing mixed-use property. 2/2 residential, office plus a detached restaurant. Seller financing is available to immediately start your investment opportunity! Call now for your private showing.

  Bobby Coe RE/MAX Keys Connection (KW)

  405 Petronia St, Key West, FL 33040
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  /44

  $1,125,000

  • 3 Beds
  • 3 Baths
  • 1,060 Sq Ft

  32 Golf Club Dr, Key West, FL 33040

  3BR/2.5BA 2 story townhouse with its own private pool and professionally landscaped yard with lush vegetation for ultimate privacy. The downstairs boasts an open concept living room, dining area and kitchen. The living area opens to the outdoor porch, pool and tropically landscaped yard with irrigation and lighting. Upstairs you will find the primary bedroom with en-suite bathroom and great

  Jenna Blackwell Berkshire Hathaway HomeServices Knight & Gardner Realty

  32 Golf Club Dr, Key West, FL 33040
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  /42

  $4,595,000

  • 4 Beds
  • 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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  /10

  $549,000

  • 1 Bed
  • 1 Bath
  • 368 Sq Ft

  1318 Duncan St Unit 3, Key West, FL 33040

  Great opportunity to own your own home or have an excellent source of rental income. Currently the least expensive detached residence in Key West. This renovated one bedroom condo cottage overlooking the large communal pool is just one block to vibrant White St with its cafes and restaurants, gourmet food stores, galleries and yoga studios. A short walk or bike ride to the beaches and the heart

  Rob Severin Rob Severin Real Estate Co

  1318 Duncan St Unit 3, Key West, FL 33040
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  /23

  $799,000

  • 2 Beds
  • 2 Baths
  • 862 Sq Ft

  1004 Watson St Unit 2, Key West, FL 33040

  Centrally located in flood X zone of Old Town, this 2-bed, 2-bath townhouse is classic Key West charm at its best. The galley kitchen offers abundant cabinetry, granite countertops, and stainless-steel appliances. High ceilings with wood-finished crown molding add warmth and character throughout. The spacious primary suite showcases beautiful Dade County pine and a private en-suite bath. Central

  Brenda Donnelly Brenda Donnelly Real Estate LLC

  1004 Watson St Unit 2, Key West, FL 33040
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  /34

  $1,250,000

  • 3 Beds
  • 2 Baths
  • 866 Sq Ft

  711 Galveston Ln, Key West, FL 33040

  Nestled down a private and picturesque lane, this charming conch-style cottage offers the perfect blend of island charm and comfort. Featuring 3 bedrooms and 2 full baths, the home is thoughtfully designed for relaxed living and effortless entertaining.Step into a beautifully landscaped backyard with a newly built pergola--ideal for dining and unwinding in the spa beneath the stars. Though

  Monique Thiel Sunshine State Realty Services

  711 Galveston Ln, Key West, FL 33040
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  /22

  $599,000

  • 3 Beds
  • 2 Baths
  • 1,069 Sq Ft

  3930 S 3930 Roosevelt Blvd Unit S303, Key West, FL 33040

  Looking for a move-in condo in Key West that's high and dry, close to the airport and on the quiet side of the island? Want to wake up to the sunrise and nice sea breezes while enjoying a cup of coffee on your balcony? This 3 bedroom, 2 bath condo at Las Salinas Condominiums checks off all the boxes for Key West living. Whether this will be your easy-to-maintain Key West getaway home, permanent

  Edward Salazar Bascom Grooms Real Estate (KW)

  3930 S 3930 Roosevelt Blvd Unit S303, Key West, FL 33040
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  /38

  $829,000

  • 3 Beds
  • 2 Baths
  • 1,060 Sq Ft

  30 Whistling Duck Ln, Key West, FL 33040

  Roomy and meticulously maintained 3 Bedroom/2 Bathroom semi-detached house, with large, landscaped rear and side yard overlooking the 7th hole at the Key West Golf Club. This homey, well-maintained townhouse is private and located near the entrance to the neighborhood for easy coming and going - and parking. Rented occasionally for $10,000 per month.This 1,060 square foot unit offers tile

  Terry Schmida Berkshire Hathaway HomeServices Knight & Gardner Realty

  30 Whistling Duck Ln, Key West, FL 33040
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  /31

  $615,000

  • 2 Beds
  • 2 Baths
  • 800 Sq Ft

  3029 N Roosevelt Blvd Unit 54, Key West, FL 33040

  Tucked inside the sought-after Key Cove community, this updated 2-bedroom, 1.5-bath townhome blends island charm with modern touches -- a great fit for a first-time homebuyer, VA loan buyer, or investor looking for a low-maintenance Key West property. Key Cove properties RARELY come on the market. The first floor offers a bright, open living and dining area that flows easily into the kitchen,

  Paige Bethel Island Home Realty Inc.

  3029 N Roosevelt Blvd Unit 54, Key West, FL 33040
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  /27

  $520,000

  • 2 Beds
  • 2 Baths
  • 804 Sq Ft

  3930 S Roosevelt Blvd Unit S111, Key West, FL 33040

  Welcome to Las Salinas! This beautifully maintained end unit with extra windows and fully furnished 2-bedroom, 2-bathroom condo offers comfort, convenience, and island living at its finest. Located on the east end of Key West, this move-in ready unit features an open floor plan with a spacious living and dining area, a private balcony and a well-appointed kitchen.The primary bedroom includes an

  Andrea Otava Last Key Realty, Inc (KW)

  3930 S Roosevelt Blvd Unit S111, Key West, FL 33040
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  /17

  $425,000

  • 2 Beds
  • 2 Baths
  • 784 Sq Ft

  6620 Maloney Ave Unit 14, Key West, FL 33040

  Well-maintained and move-in ready, this 2/2 home offers the best of island living. The home features spacious screened porches that expand your living area outdoors, ideal for relaxing or entertaining. A newly installed roof provides peace of mind, and the property's thoughtful upkeep makes it a great investment or full-time residence.

  Alexa Morgan Buy The Keys

  6620 Maloney Ave Unit 14, Key West, FL 33040
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  /25

  $383,000

  • 1 Bed
  • 1 Bath
  • 528 Sq Ft

  3312 Northside Dr Unit 405, Key West, FL 33040

  Own in Key West under 400k. Excellent investment as primary residence, second home, or rental property. This one bed one bath condo is conveniently located in a shopping area with easy access to Duval and US 1. It is one of the few gated communities in Key West. You have ample parking, storage, pool, tennis courts, laundry, on site management, etc. The unit has new flooring, new AC unit, new

  Karen Angle Coldwell Banker Schmitt Real Estate Co.

  3312 Northside Dr Unit 405, Key West, FL 33040
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  /21

  $599,000

  • 3 Beds
  • 2 Baths
  • 1,071 Sq Ft

  3930 S Roosevelt Blvd Unit E301, Key West, FL 33040

  Enjoy island living in this bright and spacious 3-bedroom, 2-bath condo at 3930 S. Roosevelt Blvd, Unit E. 301 in Key West's sought-after Las Salinas community. With over 1,000 square feet of well-designed living space, this unit offers a comfortable open floor plan, a private balcony off the master bedroom, and ample storage. The condo features a newer air-conditioning system, ensuring your

  Barbara Crespo Keller Williams Key West Compass Realty

  3930 S Roosevelt Blvd Unit E301, Key West, FL 33040
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  /37

  $1,199,000

  • 2 Beds
  • 2 Baths
  • 1,261 Sq Ft

  1209 Truman Ave Unit 5, Key West, FL 33040

  This is the one! Perfectly laid out two (2) bedroom and two (2) bathroom condo, with a den/office that could be an extra bedroom, in The Heart of Old Town Key West, with off-street parking.This amazing location comes with a a covered lanai, that will greet you each and every time you come home. Several sets of French Doors will lead you from your outdoor Oasis, that is a perfect Key West garden,

  Bobby Coe RE/MAX Keys Connection (KW)

  1209 Truman Ave Unit 5, Key West, FL 33040
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  /48

  $684,000

  • 2 Beds
  • 2 Baths
  • 900 Sq Ft

  14 Kingfisher Ln, Key West, FL 33040

  Welcome to 14 Kingfisher Lane at the Key West Golf Club Community. This lovely townhome is located in a gated residence community. Enjoy the best of island living with 2 Bedrooms & 2 en-suite bathrooms. Take in refreshing breezes and tranquil golf course views from your screened-in back porch with serene lake views and a view of the 2nd Tee of the golf course.The open-concept kitchen and living

  Christopher Orth Berkshire Hathaway HomeServices Knight & Gardner Realty

  14 Kingfisher Ln, Key West, FL 33040
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  /25

  $2,789,000

  • 3 Beds
  • 3 Baths
  • 2,212 Sq Ft

  3206 Riviera Dr, Key West, FL 33040

  Welcome to 3206 Riviera Drive, Key West - a stunning canal-front retreat designed for the ultimate Key West lifestyle. This fully gated residence offers 60 feet of waterfront with no neighbors across, creating unmatched privacy and serene water views.Inside, a bright open floor plan with a wall of glass impact sliders connects indoor living to the outdoors. The spacious kitchen features a large

  Will Langley Berkshire Hathaway HomeServices Knight & Gardner Realty

  3206 Riviera Dr, Key West, FL 33040
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  /30

  $799,000

  • 2 Beds
  • 2 Baths
  • 1,030 Sq Ft

  2119 Flagler Ave, Key West, FL 33040

  Charming Key West Single-Family Home on Oversized Lot - Room for a Pool! Welcome to your island retreat! Located in a desirable central Key West neighborhood, this well-maintained 2-bedroom, 2-bathroom single-family home sits on a spacious 5,000 sq ft (50x100) lot--offering ample space for a pool, tropical gardens, or even a guest cottage (with proper approvals).Inside, you'll find a bright and

  Jody Clark Key West Luxury Real Estate Inc (KW)

  2119 Flagler Ave, Key West, FL 33040
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  /40

  $2,850,000

  • 3 Beds
  • 3 Baths
  • 1,519 Sq Ft

  610 Griffin Ln, Key West, FL 33040

  Tucked away on a quiet lane in the heart of Old Town Key West, this rare compound blends timeless island charm with exceptional privacy--just steps from premier dining, shopping, and entertainment. Three distinct dwellings are arranged around a serene brick courtyard with a heated cocktail pool, creating an inviting retreat in one of the most sought-after neighborhoods in Key West.The main home

  Brenda Donnelly Brenda Donnelly Real Estate LLC

  610 Griffin Ln, Key West, FL 33040
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  /33

  $1,575,000 Open Sat 12PM - 2PM

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

  1612 Washington St, Key West, FL 33040

  Discover this newly listed, stunningly renovated home with a pool in Mid Town West! This midcentury modern gem is located in the heart of Key West, just a short bike ride from Old Town, pickleball courts, beach, dining, and more.Currently set up as two separate units, this property offers numerous options. It can serve as a primary residence with rental income, accommodate multi-generational

  Bascom Grooms Bascom Grooms Real Estate (KW)

  1612 Washington St, Key West, FL 33040
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  /50

  $979,900

  • 2 Beds
  • 3 Baths
  • 1,152 Sq Ft

  1611 Josephine St, Key West, FL 33040

  Exquisite 3-Level Midtown Key West Townhome. Close to Everything! Welcome to your private island get away in the heart of Midtown Key West, just two blocks from Higgs Beach, 10 min walk to Smathers Beach & less than a mile from the iconic Duval Street. This meticulously upgraded 2-bedroom, 2.5-bath, 3-level town home spans 1,152 sq. ft. and boasts a split floor plan with en-suite bathrooms for

  Stephen Hachey

  1611 Josephine St, Key West, FL 33040
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  /51

  $3,399,000

  • 4 Beds
  • 3 Baths
  • 1,734 Sq Ft

  1501 White St, Key West, FL 33040

  Key West Oasis - A Tropical Compound Steps from the Sea. House, Pool & Guest Retreat located near by Casa Marina and steps from Old Town. Welcome to your own private tropical compound just blocks from the beach, tennis and pickleball courts, and the iconic White Street Pier where you're perfectly positioned for sunrise strolls, sunset views, and everything in between. Nestled on a lush corner lot

  Miriam Novotny Compass Florida, LLC

  1501 White St, Key West, FL 33040
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  /27

  $2,350,000

  • 3 Beds
  • 3 Baths
  • 1,325 Sq Ft

  115 Front St Unit 101, Key West, FL 33040

  Prior to the development of Truman Annex which was a notable Naval base located in the center of Key West, now has many upscale homes and condos. This newly renovated 3-bedroom, 3-bathroom residence blends historic charm with cutting-edge contemporary design by interior designer David Smith.Step inside to soaring open ceilings with exposed ductwork and striking geometric lighting. Smart home

  Key West Luxury Finders Preferred Properties (KW)

  115 Front St Unit 101, Key West, FL 33040
• 

  

  /22

  $505,000

  • 2 Beds
  • 2 Baths
  • 808 Sq Ft

  3930 S Roosevelt Blvd Unit 208N, Key West, FL 33040

  Nice 2-bedroom, 2-bath condominium in the desirable Las Salinas community of Key West. Designed for comfort and style, this residence features a kitchen with granite countertops and stainless steel appliances. Floor-to-ceiling mirrors enhance the natural light, while oversized double closets in both bedrooms and an exterior storage locker provide ample storage. Enjoy your morning coffee with

  Sean Farrer Coldwell Banker Schmitt Real Estate Co. (KW)

  3930 S Roosevelt Blvd Unit 208N, Key West, FL 33040

Showing Results 161 - 200, Page 5 of 10