Homes for Sale near Monroe County Detention Center

• 

  

  

  /9

  $799,900 Open Sun 11AM - 12:30PM

  • 2 Beds
  • 2 Baths
  • 1,017 Sq Ft

  1014 Truman Ave Unit 3, Key West, FL 33040

  1014 Truman Avenue - Modern Island Elegance in the Heart of Key WestWelcome to a Key West retreat where modern design meets the island's laid-back charm. This immaculate two-bedroom, two-bath condominium has been masterfully remodeled with designer finishes, offering a home that's as stylish as it is functional.Step inside to a sunlit, open-concept living space where clean lines and bamboo

  Dominic Paolillo Jr. Truman & Co. (KW)

  1014 Truman Ave Unit 3, Key West, FL 33040
• 

  

  

  /33

  $1,995,000

  • 4 Beds
  • 3 Baths
  • 2,423 Sq Ft

  1516 17th Terrace, Key West, FL 33040

  Stunning in Sunrise Shores! Discover this corner property situated on a spacious lot exceeding 13,000 sq ft. The main residence boasts over 1,783 sq ft of living space, complemented by a guest cottage of 640 sq ft. This well-maintained property has been lovingly cared for by the owners.Main Home Features:Three Bedrooms and Two BathroomsThoughtful layout featuring:A generous family room A large

  Bascom Grooms Bascom Grooms Real Estate (KW)

  1516 17th Terrace, Key West, FL 33040
• 

  

  

  /22

  $1,795,000 Open Sun 11AM - 2PM

  • 2 Beds
  • 2 Baths
  • 1,193 Sq Ft

  915 Washington St, Key West, FL 33040

  Located in the highly sought-after Casa Marina neighborhood, 915 Washington Street offers a unique blend of privacy, style, and functional design. This newly renovated 2-bedroom, 2-bathroom residence sits on a 3,600 sq ft corner lot and features 1,193 sq ft of thoughtfully designed living space.A fully renovated kitchen anchors the open-concept layout, complemented by vaulted ceilings and ample

  Will Langley Berkshire Hathaway HomeServices Knight & Gardner Realty

  915 Washington St, Key West, FL 33040
• 

  

  

  /12

  $339,000

  • 3 Beds
  • 1 Bath
  • 720 Sq Ft

  G59 Miriam St, Stock Island, FL 33040

  Just minutes from Bernstein Park, local marinas, restaurants, the Key West Golf Club, and a short ride to Duval Street, this property is ideally situated to enjoy all the Lower Keys have to offer. Set on a 3,669 SqFt lot with no HOA--and yes, you own the land--this 1968 mobile home is being sold AS IS. It's a strong candidate for replacement, renovation, or future development.

  Keys Team Bryant and Kat Expert Realty LLC (HQ)

  G59 Miriam St, Stock Island, FL 33040
• 

  

  

  /35

  $375,000

  • 2 Beds
  • 2 Baths
  • 644 Sq Ft

  6800 Maloney Ave Unit 12, Stock Island, FL 33040

  If you are looking for something affordable & close to Key West, this is it. Harbour Shores is just 1 mile from Key West. Beautifully renovated, and ready for immediate occupancy, this 2 bedroom 1.5 bath home has been meticulously cared for by the current owner. Freshly painted, new ACs, new ceiling fans, new closets, and more. Set in a lush tree canopy with a large deck to enjoy the outdoors.

  Caroline Bauer Key West Sales, LLC

  6800 Maloney Ave Unit 12, Stock Island, FL 33040
• 

  

  /34

  $1,400,000

  • 3 Beds
  • 2 Baths
  • 1,312 Sq Ft

  1719 Washington St, Key West, FL 33040

  Welcome to this beautiful 3-bedroom, 2-bath stilted family home, perfectly designed for comfort and modern living. Nestled in a popular neighborhood, this elevated residence offers peace of mind, stunning natural views, and thoughtfully planned spaces for the whole family and guests. Sunlight pours through large windows, illuminating the open-concept living and dining areas - an ideal setting for

  LaReta Morrison eXp Realty LLC

  1719 Washington St, Key West, FL 33040
• 

  

  /87

  $3,795,000

  • 5 Beds
  • 6 Baths
  • 3,006 Sq Ft

  1022 Packer St, Key West, FL 33040

  Custom Bahamian Style Estate built in 2005! 3006 sq.ft. in Old Town X-Zone. 5 bedrooms and 5 and a half baths with generous front porches on both floors and a 2nd floor wrap around balcony in the back overlooking the pool and gardens. Spacious covered outdoor living area complements the large pool & spa. Luxurious chef's kitchen, top of the line appliances, open to great room/dining area with

  Dawn Thornburgh Beach Club Brokers (KW)

  1022 Packer St, Key West, FL 33040
• 

  

  /47

  $2,499,000 Open Sat 11AM - 2PM

  • 4 Beds
  • 2 Baths
  • 1,628 Sq Ft

  409 Grinnell St, Key West, FL 33040

  Dating back to the 1880s and appearing on the 1889 Sanborn Fire Maps, 409 Grinnell Street stands as one of Old Town Key West's most authentic restorations. Recognized with the Historic Florida Keys Foundation Star Award, this four-bedroom, two-bath residence blends historic craftsmanship with the comfort of modern island living. The layout flows easily with spacious living and dining areas, a

  Zainya Zimmerer Berkshire Hathaway HomeServices Knight & Gardner Realty

  409 Grinnell St, Key West, FL 33040
• 

  

  /33

  $825,000

  • 1 Bed
  • 1 Bath
  • 510 Sq Ft

  732 Olivia St, Key West, FL 33040

  Unlock the charm and potential of Old Town Key West living! Tucked away in the heart of Old Town, just a few blocks from world-famous Duval Street, 732 Olivia Street offers a rare opportunity to own a charming piece of Key West history. This one-bedroom, one-bath cottage with a versatile loft has been lovingly held by the same owner for over 45 years. Situated on a generous sized lot, the

  Jimmy Lane Island Life Realty Experts

  732 Olivia St, Key West, FL 33040
• 

  

  /8

  $540,000

  • 2 Beds
  • 2 Baths
  • 1,073 Sq Ft

  3930 S Roosevelt Blvd Unit N401, Key West, FL 33040

  Exceptional opportunity to own one of only 12 oversized 2-bedroom, 2-bath units at Las Salinas, offering the same square footage as the 3-bedroom layouts. This top-floor penthouse residence provides enhanced privacy and quiet living, with just three units of this type on the level.The spacious floor plan features the largest kitchen in the complex, an open living/dining area with abundant natural

  Steven Koleno Beycome of Florida, LLC

  3930 S Roosevelt Blvd Unit N401, Key West, FL 33040
• 

  

  /37

  $2,099,000 Open Sat 1PM - 3PM

  • 3 Beds
  • 2 Baths
  • 1,530 Sq Ft

  1213 Washington St, Key West, FL 33040

  Welcome to your island oasis... boasting an open floor plan with single-story living, this well-designed 3BR/2BA home is located in one of Key West's most desirable neighborhoods. Enter through a classic white picket fence and generous courtyard to the open-concept living area, featuring a chef's kitchen with beautiful granite countertops and a spacious dining room that flows seamlessly to the

  Nancy Coward Keller Williams Key West Compass Realty

  1213 Washington St, Key West, FL 33040
• 

  

  /22

  $599,000

  • 2 Beds
  • 1 Bath
  • 691 Sq Ft

  2521 Flagler Ave Unit 4, Key West, FL 33040

  This is your chance to own a piece of paradise in the middle of Key West. This two bedroom home is located in a prime midtown location and has been completely renovated with all the modern amenities you could want. The vinyl plank flooring, recessed lighting, and lighted crown moldings create a sleek and stylish look, while the stone countertops, wood cabinetry, and stainless steel appliances

  Jimmy Lane Island Life Realty Experts

  2521 Flagler Ave Unit 4, Key West, FL 33040
• 

  

  /79

  $2,849,000

  • 4 Beds
  • 3 Baths
  • 2,321 Sq Ft

  16 Azalea Dr, Key West, FL 33040

  Welcome to 16 Azalea Drive, a completely reimagined home that embodies sophisticated coastal living, blending modern elegance with meticulous attention to detail at every turn. Thoughtfully redesigned from the ground up, this 4-bedroom, 3-bath property spans nearly 2,400 sq ft of refined living space. The open layout creates a seamless flow between the living, dining & kitchen areas, each curated

  Tommy Mack Coastal Collection Real Estate Inc.

  16 Azalea Dr, Key West, FL 33040
• 

  /2

  $285,000

  • Land

  B50 9th Ave, Stock Island, FL 33040

  Vacant land offering, ROGO Exemption determination submitted. Mobile home on property is not owned by land owner. Close to Key West, park, restaurants. New homes can be built in this subdivisionNOTE zoing is URM

  Darlene Thomas Beach Club Brokers (KW)

  B50 9th Ave, Stock Island, FL 33040
• 

  /2

  $285,000

  • Land

  B38 9th Ave, Stock Island, FL 33040

  Land is available for purchase, mobile home on lot is owned by tenant who is paying rent. ROGO Exemption determination submitted. Many single family homes in neighborhood. Close to Key West.NOTE zoning is URM

  Darlene Thomas Beach Club Brokers (KW)

  B38 9th Ave, Stock Island, FL 33040
• 

  

  /34

  $1,995,000

  • 1 Bed
  • 3 Baths
  • 1,526 Sq Ft

  830 Caroline St, Key West, FL 33040

  Endless possibilities await with this mixed-use building perfectly positioned in the heart of Old Town's Historic Seaport neighborhood. This rare property blends residential and commercial flexibility in one of Key West's most sought-after locations.The second floor features a stylish studio apartment with two lofts, wood floors, a full bath, vaulted ceilings, peekaboo water views, and a private

  Solaris Gregory Expert Realty LLC (HQ)

  830 Caroline St, Key West, FL 33040
• 

  

  /21

  $1,100,000

  • 1 Bed
  • 1 Bath
  • 420 Sq Ft

  817 Terry Ln, Key West, FL 33040

  Step into a piece of Old Town Key West history.Built in 1928, this storybook Old Town cottage captures everything to love about Key West including its timeless character and that easy island rhythm you can feel the moment you arrive.Light, bright, and beautifully furnished, it's move-in ready, the perfect turn-key retreat for anyone dreaming of a second home or an easy vacation rental in the

  Mykael Marinelli American Caribbean Real Estate, Christie's International Real Estate

  817 Terry Ln, Key West, FL 33040
• 

  

  /27

  $2,299,000

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft

  703 Elizabeth St, Key West, FL 33040

  Perched at the highest island elevation referred to as Solares Hill you will find this timeless Old Town gem. A perfect blend of style and charm welcome you to an open concept floor plan with cathedral ceilings and wall of French doors that overlooks a tropical backyard oasis with heated pool, deck and brick patio. Thoughtful finishes that will stand the test of time throughout include built in

  Wendy Zintsmaster Truman & Co. (KW)

  703 Elizabeth St, Key West, FL 33040
• 

  

  /5

  $440,000

  • 2 Beds
  • 2 Baths
  • 696 Sq Ft

  3312 Northside Dr Unit 607, Key West, FL 33040

  2 BEDROOMS 2 BATHROOMS WITH BALCONY, GATED COMMUNITY, HUGE POOL, TENNIS COURT ,PLENTY OF PARKING AND WALKING DISTANCE OF SHOPPING, GROCERIES, RESTAURANTS AND MOVIE THEATRE.

  Bigya Niroula (Rihanna) eXp Realty LLC KW Branch

  3312 Northside Dr Unit 607, Key West, FL 33040
• 

  

  /45

  $869,000

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

  21 Whistling Duck Ln, Key West, FL 33040

  Welcome to your tropical retreat at 21 Whistling Duck, nestled within the serene gates of the Key West Golf Club. This beautifully updated three (3) bedroom and two-and-a-half (2.5) bath residence combines relaxed living with premium, refined finishes, all within beautiful resort-style surroundings.Step through your white picket fence, up to your front porch and into the foyer of this open &

  Bobby Coe RE/MAX Keys Connection (KW)

  21 Whistling Duck Ln, Key West, FL 33040
• 

  

  /37

  $1,442,100

  • 2 Beds
  • 1 Bath
  • 759 Sq Ft

  1020 Fleming St, Key West, FL 33040

  Welcome to 1020 Fleming Street, an adorable Conch Cottage situated on the corner of prestigious Fleming Street and Nassau Lane. Built in 1918, this two (2) bedroom and one (1) bath charming and historic home is the perfect retreat in Old Town, Key West. Once a famous Old Town Grocery Store.Step inside your white picket fence and into one of two brick-paved courtyards, complete with a fire pit

  Bobby Coe RE/MAX Keys Connection (KW)

  1020 Fleming St, Key West, FL 33040
• 

  

  /20

  $1,290,000

  • 2 Beds
  • 2 Baths
  • 1,458 Sq Ft

  702 Florida St, Key West, FL 33040

  BRAND NEW ROOF with new Kitchen Skylights! This beautiful single-story CBS home is on a desirable corner lot within the highly sought-after Meadows neighborhood. Close to the Historic Seaport and the iconic Duval Street, this charming 2-bedroom, 2-bathroom home, built in 1972, offers a light and bright open floor plan, ideal for entertaining. The kitchen features stainless steel appliances and

  Moe Smyth Island Life Realty Experts

  702 Florida St, Key West, FL 33040
• 

  

  /24

  $1,345,000

  • 4 Beds
  • 2 Baths
  • 1,660 Sq Ft

  625 Whitehead St, Key West, FL 33040

  Prime Old Town Mixed-Use Property - Live, Work, or Invest! Ideally situated in Old Town Key West, this Historic Residential Office (HRO) zoned property offers a rare opportunity for both residential and commercial use. Previously, home to a successful spa, it's perfectly suited for continuing as a business or transforming into a private residence. Filled with character, the space features

  Kate Green Old Town Realty

  625 Whitehead St, Key West, FL 33040
• 

  

  /23

  $1,199,999

  • 3 Beds
  • 2 Baths
  • 1,714 Sq Ft

  1510 18th St, Key West, FL 33040

  Lowest priced home in desirable Sunrise Shores! Just 425 feet from Jimmy Buffett's former Sunrise Drive compound, enjoy scenic morning walks past multi-million dollar waterfront estates and magnificent ocean sunrises along South Roosevelt Blvd. This versatile property boasts an enormous front yard with room for multiple vehicles, boats, and RVs - an entertainer's dream. You'll find joy every day,

  Steven Koleno Beycome of Florida, LLC

  1510 18th St, Key West, FL 33040
• 

  

  /29

  $539,000

  • 2 Beds
  • 2 Baths
  • 772 Sq Ft

  3635 Seaside Dr Unit 104, Key West, FL 33040

  Experience stunning Key West sunsets from your private balcony. This quiet residence is tucked away from the pool area, offering peaceful living with no pool noise and beautiful sunset views over the lush salt ponds. Surrounded by mangroves and wildlife, enjoy daily encounters with herons, ospreys, and pelicans, all just minutes from the turquoise waters of Smathers Beach.Inside, the comfortable

  Brenda Donnelly Brenda Donnelly Real Estate LLC

  3635 Seaside Dr Unit 104, Key West, FL 33040
• 

  

  /51

  $3,199,000

  • 2 Beds
  • 3 Baths
  • 1,120 Sq Ft

  512 Amelia St, Key West, FL 33040

  Charming, colorful, and unmistakably Key West--512 Amelia Street is where island life unfolds with ease. Enjoy your own private pool and the flexibility of a Transient License, allowing nightly rentals. Nestled in a serene pocket of Old Town, this home is surrounded by swaying palms, historic streets, and the gentle breezes of the nearby ocean. A home to love and a place guests will never want to

  Andy Birrell Berkshire Hathaway HomeServices Knight & Gardner Realty

  512 Amelia St, Key West, FL 33040
• 

  

  /17

  $235,000

  • Land

  5555 College Rd Unit 5, Key West, FL 33040

  Well-positioned 30' wet slip located at Sunset Marina on the gated side of the property. This floating concrete dock can accommodate a vessel up to 35' in length and offers deep water access with a 6' control depth -- perfect for easy navigation to both the Gulf and Atlantic waters.Sunset Marina is a full-service marina with on-site fuel, bait, and marina store. Owners enjoy access to secured

  Jimmy Lane Island Life Realty Experts

  5555 College Rd Unit 5, Key West, FL 33040
• 

  

  /83

  $1,400,000

  • 6 Beds
  • 7 Baths
  • 1,306 Sq Ft

  1824 Fogarty Ave, Key West, FL 33040

  This 4-unit tropical compound spans nearly 9,500 sq. ft. and includes a spacious 3BD/3.5BA main home plus three charming 1BD/1BA cottages. Enjoy resort-style living with a pool, tiki bar, and lush outdoor space. This property offers flexibility for employee housing, long-term rentals, or a 'Key West Melrose Place'-style retreat. Centrally located near beaches, dining, and Old Town--live and earn

  Krystal Thomas eXp Realty LLC

  1824 Fogarty Ave, Key West, FL 33040
• 

  

  /29

  $2,299,000

  • 3 Beds
  • 2 Baths
  • 1,516 Sq Ft

  1116 Elgin Ln, Key West, FL 33040

  This quintessential two story, 3/2 Key West home is situated in the Historic Seaport District on a quiet lane with coveted off street parking.....The original structure can be traced back to the 1850s and has many beautiful historic features such as Dade County Pine walls and flooring. The home has a wonderful open design with the kitchen overlooking the large, vaulted living/dining area. A wall

  Rob Severin Rob Severin Real Estate Co

  1116 Elgin Ln, Key West, FL 33040
• 

  

  /71

  $6,750,000

  • 5 Beds
  • 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 desirable

  Bobby Coe RE/MAX Keys Connection (KW)

  411 Louisa St, Key West, FL 33040
• 

  

  /25

  $1,449,000

  • 4 Beds
  • 3 Baths
  • 1,767 Sq Ft

  1527 von Phister St, Key West, FL 33040

  Centrally located in the heart of Key West, this beautifully restored traditional Conch-style home offers two legal units and exceptional versatility.The first-floor residence features two bedrooms and two bathrooms, a charming covered front porch, and thoughtfully updated interiors that maintain authentic island character. Upstairs, a bright and airy two-bedroom, one-bath home enjoys its own

  Key West Luxury Finders Preferred Properties (KW)

  1527 von Phister St, Key West, FL 33040
• 

  

  /10

  $1,824,900

  • 9 Beds
  • 7 Baths
  • 3,687 Sq Ft

  1821 Harris Ave, Key West, FL 33040

  Triplex with Stunning Rent Roll ($172,800/year)- This income-producing triplex features three well-maintained units, each offering 3 bedrooms and 2 bathrooms. The front unit, originally larger than the rear units and spans one level--ideal for tenants seeking single-story living. The rear units are two-story layouts, with bedrooms and baths upstairs and kitchen/living areas on the main level.

  Kayley Arn Coldwell Banker Realty - Aventura

  1821 Harris Ave, Key West, FL 33040
• 

  

  /18

  $699,500

  • 2 Beds
  • 1 Bath
  • 612 Sq Ft

  1042 United St, Key West, FL 33040

  Discover your perfect Key West getaway at 1042 United Street -- a charming single-story cottage with two bedrooms, one bath, and all the island character you've been dreaming of. Relax on the inviting front porch with your morning coffee, then unwind on the private back patio after a day of sun and sea. Bright, open interiors and a seamless indoor-outdoor flow make this home ideal for easy

  Barbara Crespo Keller Williams Key West Compass Realty

  1042 United St, Key West, FL 33040
• 

  

  /5

  $1,068,000

  • 6 Beds
  • 2 Baths
  • 1,694 Sq Ft

  1916 Seidenberg Ave, Key West, FL 33040

  Duplex with Solid Rent Roll ($91,800/year) - This income-producing duplex features 2 well-maintained units, each offering 3 bedrooms and 1 bathrooms. Units are rented for $3,850 and $3,800 per month on long-term leases ($91,800/year). Perfectly positioned near the coast and only a short ride from the energy of downtown.

  Kayley Arn Coldwell Banker Realty - Aventura

  1916 Seidenberg Ave, Key West, FL 33040
• 

  

  /63

  $3,395,000 Open House 11/30

  • 4 Beds
  • 4 Baths
  • 2,488 Sq Ft

  102 Admirals Ln, Key West, FL 33040

  The ultimate lock-and-leave Key West retreat awaits in the heart of Old Town! Perfect for those seeking a low-maintenance getaway without the upkeep of a large yard or pool, this residence offers effortless luxury living and the convenience of a fly-in, fly-out lifestyle.Located on exclusive Admirals Lane within the award-winning Truman Annex, this is the largest townhouse in the community. The

  Lisa Swanson The Agency Florida Keys

  102 Admirals Ln, Key West, FL 33040
• 

  

  /16

  $593,500

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

  3930 S Roosevelt Blvd Unit N304, Key West, FL 33040

  Experience the easygoing charm of island life in this thoughtfully updated 3-bedroom, 2-bath condo, in the desirable resort-style living in Las Salinas. Light pours into the open-concept living space, creating a warm and inviting atmosphere that feels like home. The primary suite includes a private balcony that overlooks the pool and steps away from the newly updated fitness center. The modern

  Kayley Arn Coldwell Banker Realty - Aventura

  3930 S Roosevelt Blvd Unit N304, Key West, FL 33040
• 

  

  /12

  $1,100,000

  • Land

  619 Front St Unit 21, Key West, FL 33040

  BEST MARINA LOCATION IN KEY WEST!Coveted and rarely available slip at the Galleon Resort in Historic Key West Harbor is now available.At the Galleon Resort, enjoy stunning sunset vistas, viewings of lighted boat parades and a two-block walk to Duval Street! The Historic Key West Seaport district is a stone's throw away where you can dine, drink and listen to live music at a multitude of great

  Dawn Gonet Berkshire Hathaway HomeServices Knight & Gardner Realty

  619 Front St Unit 21, Key West, FL 33040
• 

  

  /44

  $6,850,000

  • 3 Beds
  • 3 Baths
  • 4,200 Sq Ft

  103 Front St, Key West, FL 33040

  103 Front Street is a one of a kind masterpiece of architectural design and modern aesthetic. Built in the early 1900s, this imposing structure has been thouroughly restored and updated into a stunning home. The interior features a large great room with soaring ceilings, custom beams and woodwork. A dramatic staircase leads to a second floor walkway which is open to the main level. On one end is

  Laura McChesney Preferred Properties (KW)

  103 Front St, Key West, FL 33040
• 

  

  /91

  $3,995,000

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

  919 Thomas St, Key West, FL 33040

  Charming Multifamily Compound in Historic Key West, Florida. Discover the allure of old historic Key West with this exceptional multifamily 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 of Key West

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

  919 Thomas St, Key West, FL 33040
• 

  

  /85

  $1,489,000

  • 2 Beds
  • 2.5 Baths
  • 2,292 Sq Ft

  1616 Atlantic Blvd Unit 5, Key West, FL 33040

  Rare Luxurious Atlantic Oceanfront Concrete 3 story home. 2 Bedrooms 2 1/2 bathrooms located in a private gated community. Ocean views from your balconies. This exquisite home has stainless steel appliances, custom cabinetry, vaulted ceilings, tiled carport, oversized well-manicured, private back yard. Huge storage room with built in shelving. This rare unit has the largest backyard in the

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

  1616 Atlantic Blvd Unit 5, Key West, FL 33040

Showing Results 81 - 120, Page 3 of 10