Homes for Sale near Monroe County Detention Center

• 

  

  

  /10

  $3,491,000

  • 16 Beds
  • 8 Baths
  • 6,000 Sq Ft

  1716 Bertha St, Key West, FL 33040

  EMPLOYEE HOUSING, DEVELOPERS, CONDO CONVERSION! 1714 Bertha St and 1716 Bertha St are two fourplexes with 16 bedrooms and 8 baths, 8 units of 2/1 each, comprising 6,000 sq ft of Floor Living Area on 8,755 sq ft of land, offered with the vacant lot adjacent to 1714 Bertha St, a bonus 5,765 sq ft lot comprising a total of 14,529 sq ft of land. Both buildings have new metal roofs as of 2024.

  Jeffrey Dunaway Key West Realty, LLC (KW)

  1716 Bertha St, Key West, FL 33040
• 

  

  

  /15

  $5,197,000

  • 10 Beds
  • 9 Baths
  • 7,193 Sq Ft

  1005 Flagler Ave, Key West, FL 33040

  INVESTORS, DEVELOPERS, CONDO CONVERSION--1005 FLAGLER AVE AND 1009 FLAGLER AVE--Two fourplexes in the highly desirable Casa Marina neighborhood on 18,371 sq ft of land, with 7,193 sq ft of Floor Living Area, for a total of 10 bedrooms and 9 baths. 1005 Flagler is 4 units, 3 of which are 1/1, ground floor unit #1 is a 3/2 with a courtyard. There's an on site coin laundry, as well as a garage and

  Jeffrey Dunaway Key West Realty, LLC (KW)

  1005 Flagler Ave, Key West, FL 33040
• 

  

  

  /47

  $3,999,000

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

  919 Thomas St Unit A,1-3, Key West, FL 33040

  This is the entire four-unit Lighthouse View Condominium Association. It is currently four lucrative long-term rentals. Enter thru the electric gate to a bricked courtyard with parking for several cars and many bicycles and access to a covered carport. The main residence is secluded in the rear with its own private heated pool, hot tub and expansive garden with brick terrace. A free-standing two

  Mabry Binnicker Preferred Properties (KW)

  919 Thomas St Unit A,1-3, Key West, FL 33040
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  /32

  $1,680,000

  • 3 Beds
  • 2 Baths
  • 1,463 Sq Ft

  1211 Catherine St, Key West, FL 33040

  This charming historic home is located just steps off vibrant White St and close to the beach, tennis courts, pickle ball and a short walk to famous Duval St. It's close to the action but in a tranquil area of the White St District.This property has many great features such as 10ft high ceilings through out the entire home, abundance of large windows, open floor plan with spacious living area,

  Haydee Stewart Bascom Grooms Real Estate (KW)

  1211 Catherine St, Key West, FL 33040
• 

  

  

  /35

  $580,000

  • 2 Beds
  • 2 Baths
  • 1,032 Sq Ft

  3210 Eagle Ave, Key West, FL 33040

  NEW LISTING! Welcome to Key West Estates, a charming family community ideally situated just a short bike ride from the beautiful beaches, vibrant Duval Street, delightful restaurants, the theater, and shopping centers. This peaceful neighborhood features light one-way traffic and no HOA fees, making it a perfect place to call home.Step inside to discover an inviting open floor plan that

  Bobby Baker Brightwild Real Estate

  3210 Eagle Ave, Key West, FL 33040
• 

  

  /64

  $4,250,000

  • 5 Beds
  • 7 Baths
  • 2,681 Sq Ft

  1311 Grinnell St, Key West, FL 33040

  This stunning home in Casa Marina is a complete restoration of the original historic structure. Just 5 blocks from Higgs Beach and 6 blocks from Duval Street this property has a large master bedroom and two guest bedrooms on the main floor all with private baths and their own entrances opening to over 900 square feet of wraparound porches. The wide entrance hallway has an additional 1/2 bath and

  Jennifer Newman Truman & Co. (KW)

  1311 Grinnell St, Key West, FL 33040
• 

  

  /20

  $1,750,000

  • 2 Beds
  • 1 Bath
  • 759 Sq Ft

  1020 Fleming St, Key West, FL 33040

  Discover your dream surfer's cottage on a tropical island! Built in 1918, this charming home still showcases elements of its historic architecture, blending timeless character with a unique coastal vibe. Located at 1020 Fleming Street in the Historic Seaport area of Old Town Key West, you'll be just a short walk from amazing restaurants, great bars, and some of the best fishing and diving

  Patrick Godsell Key West Luxury Real Estate Inc (KW)

  1020 Fleming St, Key West, FL 33040
• 

  

  /40

  $1,749,000

  • 3 Beds
  • 3 Baths
  • 1,897 Sq Ft

  1033 Catherine St, Key West, FL 33040

  Step into Key West history with a modern twist at the Kali Zoi House, a meticulously maintained gem nestled in lush tropical surroundings in Old Town Key West. Originally built in the early 1900s & updated in 1988, this fully furnished home offers nearly 1,900sqft of spacious living. Located near everything (Duval Street, beaches, etc.), this home combines historic charm with unbeatable

  Madeleine Lowe Expert Realty LLC (HQ)

  1033 Catherine St, Key West, FL 33040
• 

  

  /23

  $894,000

  • 2 Beds
  • 2 Baths
  • 1,469 Sq Ft

  1800 Atlantic Blvd Unit 217B, Key West, FL 33040

  New Price Reduction.Two bedroom two bath spacious condominium located in the highly desirable 'B' building at 1800 Atlantic. These units do not come on the market very often. Featuring an extra large floor plan with access to the spacious balcony from both bedrooms and the living room. Currently on an annual lease that expires August 15th 2025. The unit is being sold turn key. There is a demand

  Julia Besson Century 21 All Keys Inc (KW)

  1800 Atlantic Blvd Unit 217B, Key West, FL 33040
• 

  

  /31

  $875,000

  • 3 Beds
  • 2 Baths
  • 1,386 Sq Ft

  1901 S Roosevelt Blvd Unit 308N, Key West, FL 33040

  This spacious 3-bedroom, 2-bath condo at La Brisa offers breathtaking views of the serene salt ponds, providing a tranquil retreat while still offering convenient access to both Old Town and New Town Key West.Step into resort-style living with amenities that cater to relaxation and recreation. Take a dip in the sparkling pool, unwind in the spa and sauna, or enjoy a friendly match on the tennis

  Justyn Ewald Expert Realty LLC (HQ)

  1901 S Roosevelt Blvd Unit 308N, Key West, FL 33040
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  /33

  $1,649,500

  • 2 Beds
  • 4 Baths
  • 1,824 Sq Ft

  28 Seaside Ct S, Key West, FL 33040

  Discover the ultimate coastal retreat in this exquisite ocean view townhome, where luxury meets convenience in a serene gated environment. This three-level masterpiece exemplifies modern coastal living, with resilient construction designed to endure nature's elements while captivating the eye.Enjoy effortless movement throughout the home with a private elevator leading you to spacious living

  Hana Tomita Berkshire Hathaway HomeServices Knight & Gardner Realty

  28 Seaside Ct S, Key West, FL 33040
• 

  

  /22

  $2,895,000

  • 4 Beds
  • 3 Baths
  • 2,880 Sq Ft

  1100 South St, Key West, FL 33040

  Located in the highly regarded Casa Marina neighborhood, this exceptional property offers a unique opportunity to own a piece of Key West history. Ernest Hemingway the iconic literary figure once called this house his Winter retreat during 1928 -1929, where he penned the timeless classic, 'A FAREWELL TO ARMS.'' This sprawling single story property spans an impressive 8100 square feet, occupying a

  Key West Luxury Finders Preferred Properties (KW)

  1100 South St, Key West, FL 33040
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  /11

  $449,000

  • 3 Beds
  • 2 Baths
  • 924 Sq Ft

  25D 10th Ave, Stock Island, FL 33040

  Come share in the ''Key West'' address on ''up & coming'' Stock Island. Excellent opportunuty for a CASH BUYER! Just minutes from Key West proper, yet nestled in a tranquil area, with world-class dining, entertainment & beaches close at hand. Attractive price point in this charming mobile home on a generously sized corner lot with soft St. Augustine grass beneath your feet,. Plenty of room to

  Robin Mitchell Keller Williams Key West Compass Realty

  25D 10th Ave, Stock Island, FL 33040
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  /30

  $2,290,000

  • 4 Beds
  • 5 Baths
  • 2,376 Sq Ft

  1730 United St, Key West, FL 33040

  Exceptional newly built (2023) 4-bedroom, 4 1/2-bath home situated on a corner lot in Key West, featuring a large saltwater, heated pool and hot tub. This home offers a blend of luxury and practicality with highlights including: a corner lot location, soaring ceilings on both levels, crown molding, and a full ensuite bath in every bedroom. The open-concept first floor is perfect for entertaining,

  Tammy Stiles Berkshire Hathaway HomeServices Knight & Gardner Realty

  1730 United St, Key West, FL 33040
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  /26

  $980,000

  • 2 Beds
  • 2 Baths
  • 1,095 Sq Ft

  1312 Catherine St, Key West, FL 33040

  This charming duplex has much to offer. A great location, two very nice one bedroom, one bath units, each with their own entry and outdoor space and it's in move in condition. The first floor features a primary bedroom with Dade Pine walls and a large closet. The kitchen/living/dining area opens to the private exterior deck. Upstairs the 1/1 has high ceilings and natural light. It has a porch in

  Laura McChesney Preferred Properties (KW)

  1312 Catherine St, Key West, FL 33040
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  /25

  $2,295,000

  • 3 Beds
  • 3 Baths
  • 1,681 Sq Ft

  531 Frances St, Key West, FL 33040

  Welcome home to 531 Frances Street, located in the heart of old town Key West within walking distance to shops, restuarants, harbor walk and Duval. From the white picket fence to the wide front porch, this charming home is a classic. The first floor features an open floor plan with high ceilings and gorgeous natural light. The living room, dining and kitchen all open to the decked pool area. A

  Laura McChesney Preferred Properties (KW)

  531 Frances St, Key West, FL 33040
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  /19

  $743,000

  • 1 Bed
  • 1 Bath
  • 500 Sq Ft

  617 Fleming St Unit 6, Key West, FL 33040

  You can't beat this location, it's superb! This delightful 1/1 condo in the coveted Campbell Courtyard has a well-documented rental history as a monthly vacation rental. Secure and private, the Campbell Courtyard is a long-established small association of only 9 units. The front porch looks out to the pool. Offered fully furnished, this is a must see!

  Tyler Caudell Key West Realty, LLC (KW)

  617 Fleming St Unit 6, Key West, FL 33040
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  /47

  $2,195,000

  • 3 Beds
  • 4 Baths
  • 1,522 Sq Ft

  816 Ashe St, Key West, FL 33040

  This beautifully renovated conch home is a proud recipient of the 2024 Historic Florida Keys Foundation Preservation Award. Originally built in 1906, it has been meticulously restored from the ground up, essentially making it a brand-new property. The home features off-street parking, a heated/chilled pool, and comes fully furnished, offering a turnkey experience. Situated within walking distance

  Bascom Grooms Bascom Grooms Real Estate (KW)

  816 Ashe St, Key West, FL 33040
• 

  

  /21

  $4,999,000

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

  515 Amelia St, Key West, FL 33040

  Discover the charm of Casa Grande, a stunning TRANSIENT residence with a strong rental history. Nestled on a tranquil dead-end street, just one block from the vibrant Duval Street in Key West, this exceptional home offers off-street parking for two vehicles.Designed for entertaining, Casa Grande features an expansive open floor plan that seamlessly connects the spacious living room to the

  Jenny Perry Preferred Properties (KW)

  515 Amelia St, Key West, FL 33040
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  /30

  $998,000

  • 2 Beds
  • 2 Baths
  • 1,700 Sq Ft

  608 Roberts Ln, Key West, FL 33040

  OLD TOWN CONCH HOUSE on a lovely Lane tucked away but close to all of your favorite shops, cafes and Key West attractions! First time on the market in over 45 years! This historic home built by the Roberts Family is located on a quiet cul-de-sac lane in Old Town Key West. Tucked away and just off Frances St, 608 Roberts Lane (formerly known as Cates Lane as well as Darwin Court dates back to the

  Bascom Grooms Bascom Grooms Real Estate (KW)

  608 Roberts Ln, Key West, FL 33040
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  /18

  $689,000

  • Land

  5950 Peninsular Ave Unit 674, Key West, FL 33040

  Florida Keys living beckons at this oceanfront marina community. Aptly named Oceanside Marina. Includes parking, dock-box, electric/water hookup as well as laundry/bath facilities. Docks received complete refurbishment in 2017. Adjacent hotel built in 2017 offers 6 pools, restaurant, dog park, hourly shuttles downtown, fuel dock, kayak tours, charter fishing. Live aboard your vessel or rent out

  Zachary Bentley Coastal Collection Real Estate Inc.

  5950 Peninsular Ave Unit 674, Key West, FL 33040
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  /59

  $4,300,000

  • 4 Beds
  • 5 Baths
  • 3,204 Sq Ft

  22 Floral Ave, Key West, FL 33040

  This 4b/4.5ba luxurious home boasts Gulf of Mexico & deep canal waterfront living in Key West. It includes hurricane shutters, impact windows, metal roof with solar panels, and automated blinds. Ample parking with 2 large garages & driveway for 3 cars. 1st floor has a Chef's kitchen, a dining room perfect for hosting parties, a luxurious master suite with walk-in custom closets and the en-suite

  22 Floral Ave, Key West, FL 33040
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  /21

  $620,000

  • 1 Bed
  • 1 Bath
  • 610 Sq Ft

  1402 Olivia St Unit 2, Key West, FL 33040

  Motivated Seller! Bring all offers. Charming little hide-away in the beautiful and sought-after Meadows neighborhood of Key West. Lovely french doors welcome you in from the shared second story deck. This cozy one bedroom unit has everything you'll need including an updated kitchen with granite, stone and stainless steel. Gorgeous mosaic tile in the bathroom as well as a custom glass shower

  1402 Olivia St Unit 2, Key West, FL 33040
• 

  

  /41

  $2,695,000

  • 3 Beds
  • 2 Baths
  • 2,090 Sq Ft

  117 Key Haven Rd, Key West, FL 33040

  Elevation, Location and Strength, 117 Key Haven Road was built to stand the test of time. With it's Elevated concrete construction, metal roof and impact windows and doors, this home offers excellent protection of your investment and safety for your family and high quality comfort.It's combination of large 9300 sq ft. lot, excellent deep water access and stunning open water views of the bay and

  Suzanne Moore Suzanne Moore Real Estate

  117 Key Haven Rd, Key West, FL 33040
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  /3

  $1,399,000

  • Land

  1513 Seminary St, Key West, FL 33040

  Discover an incredible opportunity in the heart of Key West! This 7,500 sq. ft. lot is cleared, ready for the construction of your dream single-family home. With a transferable building permit in hand, the possibilities are endless. Enjoy the perfect blend of privacy and convenience, just moments from everything Key West has to offer. Don't miss out on this rare chance to create your ideal

  Tammy Stiles Berkshire Hathaway HomeServices Knight & Gardner Realty

  1513 Seminary St, Key West, FL 33040
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  /20

  $3,295,000

  • 3 Beds
  • 3 Baths
  • 2,100 Sq Ft

  728 Love Ln, Key West, FL 33040

  Located in Old Town Key West, and on one of the most sought after tranquil lanes, sits this perfectly updated home in the X zone. Upon entering, the foyer seamlessly flows into an open-concept living room and kitchen. You're welcomed by a breathtaking cathedral ceiling that enhances the sense of space, while large pocket doors draw your gaze to the outdoors. An expansive lanai extends the living

  Key West Luxury Finders Preferred Properties (KW)

  728 Love Ln, Key West, FL 33040
• 

  

  /5

  $950,000

  • Land

  5645 Macdonald Ave, Stock Island, FL 33040

  A rare opportunity to purchase a buildable 50x125 vacant lot that is located directly in the prime commercial corridor of Stock Island. The liberal zoning of Mixed Use (MU) is ideal for redevelopment and allows for many different uses. This lot conveys with (3) three residential unit vested rights and a minimum of 2754 square feet of commercial NROGO building rights that can be either developed

  Terry Garcia Keller Williams Key West Compass Realty

  5645 Macdonald Ave, Stock Island, FL 33040
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  /41

  $1,249,000

  • 4 Beds
  • 3 Baths
  • 1,740 Sq Ft

  1215 Bay St, Key West, FL 33040

  This charming four-bedroom, three-bathroom duplex is a rare find, nestled on a generous 7,500 sq. ft. lot that provides plenty of room for relaxation, gardening, or entertaining. Surrounded by lush foliage, the property offers a serene sense of privacy and seclusion, making it a perfect retreat. Centrally located, you'll enjoy easy access to shopping, dining, and the beach, with Old Town Key West

  Justyn Ewald Expert Realty LLC (HQ)

  1215 Bay St, Key West, FL 33040
• 

  

  /17

  $2,175,000

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

  1115 Fleming St, Key West, FL 33040

  This home has not been sold in over 100 years! The property sits on the corner of world famous Millionaire Row and one of the last not to be renovated. Do not buy someone else's overpriced flip. Bring your imagination, contractor and bring this home back to its original beauty. The lot is almost 5000 SF and runs from Fleming St. to Stickeny Lane, where there is ample off-street parking. The 1890

  Derek Epperly Keys Atlantic Realty

  1115 Fleming St, Key West, FL 33040
• 

  

  /21

  $1,550,000

  • 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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  /17

  $650,000

  • 1 Bed
  • 1 Bath
  • 640 Sq Ft

  816 South St Unit 4, Key West, FL 33040

  Experience the charm of this bright and airy 1-bedroom, 1-bathroom Southpark Condominium located in the prestigious Casa Marina neighborhood. Known for its tranquil atmosphere and prime location, this condominium is just a short stroll from Higgs Beach, the beloved Salute! on the Beach, and the iconic Louie's Backyard, where you can enjoy breathtaking ocean views and savor fine dining. Enjoy two

  Team Kaufelt Truman & Co. (KW)

  816 South St Unit 4, Key West, FL 33040
• 

  

  /23

  $1,440,000

  • 3 Beds
  • 3 Baths
  • 1,296 Sq Ft

  308 Peacon Ln, Key West, FL 33040

  Now priced to sell with this $50,000 price improvement! Enjoy Key West living on one of our most picturesque Old Town lanes. Located in the heart of the historic district and near the seaport, everything you want in Key West is right out your door. Built in the early 1900s, over the years the home was converted into a legal 2-unit property with separate water & electric accounts, however easily

  Vic Musmanno Coldwell Banker Schmitt Real Estate Co. (KW)

  308 Peacon Ln, Key West, FL 33040
• 

  

  /23

  $735,000

  • 2 Beds
  • 1 Bath
  • 643 Sq Ft

  409 Margaret St Unit 202 / B, Key West, FL 33040

  Close to the Historic Seaport, restaurants, art galleries, and more!. Recently renovated, this 2 bedroom, 1 bath condo has high impact windows and door, washer/ dryer, tankless hot water heater, new flooring, kitchen, mini splits, appliances, and is being sold furnished! Prime Old Town location, walk or bike to everything! This is easy island living- close to everything, and no need for a car.

  Elaine Coyle Keller Williams Key West Compass Realty

  409 Margaret St Unit 202 / B, Key West, FL 33040
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  /30

  $1,668,000 Open Sun 1PM - 3PM

  • 3 Beds
  • 2 Baths
  • 1,051 Sq Ft

  1202 Whitehead St, Key West, FL 33040

  This beautifully restored old Key West home offers the perfect tropical escape. Located just a block from Duval Street, Garden of Roses combines historic charm with modern upgrades, making it an ideal vacation home. Currently being rented as a monthly vacation rental!Enjoy a spacious layout with 3 bedrooms, a high-end kitchen, and bright, open living areas. Relax outdoors with a private hot tub,

  Richard Haskins Buy The Keys

  1202 Whitehead St, Key West, FL 33040
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  /58

  $2,895,000

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

  3615 Eagle Ave, Key West, FL 33040

  Welcome to 3615 Eagle Avenue, a stunning, spacious, custom built residence surrounded by it's own private botanical garden. The oversized double door entryway indicates what awaits you on the inside. Large sweeping rooms with high cathedral ceilings, gorgeous tile floors, double doors opening to the garden from every room, all designed with one-level living and an emphasis on engaging one eye to

  Suzanne Moore Suzanne Moore Real Estate

  3615 Eagle Ave, Key West, FL 33040
• 

  

  /60

  $4,850,000

  • 5 Beds
  • 4 Baths
  • 3,148 Sq Ft

  202 Admirals Ln, Key West, FL 33040

  Investment opportunity! Weekly rentals are allowed! Nestled within the highly sought-after Truman Annex in Old Town Key West, 202 Admirals Lane exudes coastal charm and luxury living at its finest. Boasting 5 bedrooms and 4 full bathrooms, this meticulously maintained residence showcases beautifully renovated bathrooms and a private pool oasis, offering an idyllic retreat for residents and

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

  202 Admirals Ln, Key West, FL 33040
• 

  

  /59

  $1,299,000

  • 3 Beds
  • 3 Baths
  • 1,850 Sq Ft

  2816 Flagler Ave, Key West, FL 33040

  Rare opportunity to purchase a stunning, only 7-year-old, 3 bedroom, 2 and 1/2 bath, 1,850 square foot, elevated home that is centrally located on the island. The Enclave on Riviera is a gated community that was built to the highest levels of the Florida Green building standards and includes a pool (complete with Tiki Hut!) and private access to kayaking and paddleboarding on the Riviera canal.

  Karen Lane Berkshire Hathaway HomeServices Knight & Gardner Realty

  2816 Flagler Ave, Key West, FL 33040
• 

  

  /63

  $3,100,000

  • 5 Beds
  • 4 Baths
  • 2,711 Sq Ft

  1419 Thompson St, Key West, FL 33040

  Stately Key West home has undergone a stunning renovation but maintains classic Keys charm with a beautiful wood staircase, stained glass window and transom, Dade County pine walls, and wraparound porches on both levels. Centrally located in Key West this home is the perfect island residence with POOL! The main level offers plenty of room for entertaining with large spaces for conversation,

  Bascom Grooms Bascom Grooms Real Estate (KW)

  1419 Thompson St, Key West, FL 33040
• 

  

  /51

  $4,295,000

  • 5 Beds
  • 3 Baths
  • 3,300 Sq Ft

  1319 Olivia St, Key West, FL 33040

  Built in 1943, and Originally owned within the Singleton Estate, 1319 Olivia St. is more than just a home, it's a legacy, embodying beauty, elegance and history at every turn.Ideally located within the heart of the meadows, this Historic Grand Dame is one of the most impressive homes in Key West today, known for it's stunning architecture and superb craftsmanship.Both kitchen and living rooms

  Suzanne Moore Suzanne Moore Real Estate

  1319 Olivia St, Key West, FL 33040
• 

  

  /35

  $1,399,000

  • 2 Beds
  • 3 Baths
  • 960 Sq Ft

  231 Southard St, Key West, FL 33040

  For the first time, the Key West home of famed landscape architect and Martha Stewart co-star Fernando Wong is available. Welcome to your dream townhouse nestled in the heart of the exclusive Truman Annex, just steps away from the restaurants, shops and bars on Duval Street. This professionally decorated 2-bedroom, 2.5-bathroom townhouse offers the perfect blend of modern comfort and island

  Carrie Howe Keller Williams Key West Compass Realty

  231 Southard St, Key West, FL 33040

Showing Results 281 - 320, Page 8 of 11