Homes for Sale near Monroe County School District Virtual Instruction Program

• 

  

  

  /27

  $1,249,000

  • 3 Beds
  • 2 Baths
  • 1,395 Sq Ft

  1209 Pearl St, Key West, FL 33040

  Charming historic duplex ideally located within walking distance to the White Street Gallery District, Old Town, and Key West beaches. The ground-floor unit features a 2BD/1BA layout with a separate living room and updated kitchen, off-street parking, and good size yard with room to add a pool. A covered outdoor living area spans the length of the property and is surrounded by tropical

  Will Langley Berkshire Hathaway HomeServices Knight & Gardner Realty

  1209 Pearl St, Key West, FL 33040
• 

  

  

  /4

  $109,000

  • Land
  • 0 Acre

  1801 N Roosevelt Blvd, Key West, FL 33040

  The most affordable living accommodation in all of Key West. The 1993 Catalina 28' sailboat is being conveyed with a leasehold at the City's Garrison Bight Marina. The slip will accommodate a 48-50' vessel with a 12' maximum beam if a replacement is desired. Garrison Bight Marina is a liveaboard community and provides pumpout, laundry and bath facilities, 2 parking passes and patrolled security.

  Randy Moss Coldwell Banker Schmitt RE Co

  1801 N Roosevelt Blvd, Key West, FL 33040
• 

  

  /2

  $375,000

  • Land

  Unlisted Address

  Great opportunity and location to ow a deep water slip. Minutes from Key West. Enjoy the laid back atmosphere of Safe Harbour Marina.

  Marc Ulanowski Equestrian Sotheby's International Realty

  Unlisted Address
• 

  

  

  /36

  $4,600,000

  • 4 Beds
  • 4 Baths
  • 3,066 Sq Ft

  1227 Washington St, Key West, FL 33040

  Offering 'Turn Key' - Move in Ready. This beautiful Key West home on two lots just blocks from the Atlantic Ocean has undergone a total property renovation including a magnificent addition. Quality materials and custom finishes have been utilized to produce a luxurious yet casually elegant 4BR/3.5BA single level home with two cottages, generous gated off street parking, heated/chilled pool and

  Nancy Swift Location 3 Real Estate of KW Inc (KW)

  1227 Washington St, Key West, FL 33040
• 

  

  

  /3

  $300,000

  • Land

  6000 Peninsular Ave, Key West, FL 33040

  Exceptional opportunity to own a dry rack boat slip accommodating vessels up to 35 feet at sought-after Stock Island Marina, offering some of the best boating access in the Florida Keys with quick, direct entry to the Atlantic Ocean. This covered, secure rack storage provides convenient launch and retrieval along with well-maintained marina facilities designed for ease and protection. Ideal for

  Rebecca Cobo Berkshire Hathaway HomeServices Knight & Gardner Realty

  6000 Peninsular Ave, Key West, FL 33040
• 

  

  /74

  $2,199,000

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

  1609 United St, Key West, FL 33040

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

  Tammy Stiles Berkshire Hathaway HomeServices Knight & Gardner Realty

  1609 United St, Key West, FL 33040
• 

  

  /33

  $850,000

  • 2 Beds
  • 2 Baths
  • 648 Sq Ft

  906 Truman Ave Unit 2, Key West, FL 33040

  Old Town First floor 2 Bedroom, 2 Bath condo, pool side!. Great Old Town location, close to Restaurants, '' Walk on White' , Grocery store, and a short walk or bicycle ride to Duval street. This wonderful 2 bedroom, 2 bath condo is one of 4 units and is located steps from the shared pool. Unique to this condo is an outside covered area with a Grill, wet-bar, and seating, exclusively for use with

  Elaine Coyle Keller Williams Key West Compass Realty

  906 Truman Ave Unit 2, Key West, FL 33040
• 

  

  /60

  $7,695,000

  • 11 Beds
  • 11 Baths
  • 3,034 Sq Ft

  525 Simonton St, Key West, FL 33040

  A Rare Investment Opportunity in the Heart of Old Town Key West. NIGHTLY rentals allowed. Introducing The Watson House--one of the largest and most versatile TRANSIENTLY licensed estates in Key West. Situated just one block off Duval Street on iconic Simonton Street, this 11-bedroom, 11-bath compound spans two distinct residences: a stately 7-bedroom mansion and a sleek, modern 4-bedroom

  Paige Bethel Island Home Realty Inc.

  525 Simonton St, Key West, FL 33040
• 

  

  /13

  $995,000

  • Land

  6810 Front St Unit S-LL-1C, Stock Island, FL 33040

  One of the largest LIVEABOARD slips in the Florida Keys.Perfect for large yachts and wide beam catamarans...Survey shows 100' long by 34' wide...but can accommodate up to 125' LOA boat.Safe Harbour Marina is a deep water (14' min.) protected port and recreational marina. Originally constructed in the late 1950's and located in the heart of the last vestiges of the commercial fishing and shrimping

  Jerry Hughes Old Town Realty

  6810 Front St Unit S-LL-1C, Stock Island, FL 33040
• 

  

  /36

  $1,695,000 Open Thu 1PM - 3PM

  • 3 Beds
  • 3 Baths
  • 1,553 Sq Ft

  322 Southard St, Key West, FL 33040

  Charming Old Town property located on the desirable Southard Street location. Within walking distance to beaches, dining and Duval Street art gallery's and night life. Historic Key West character, large lot with room for a pool, two beautiful porches to sit back and enjoy the amazing weather we are blessed with. Behind the charming white picketed fence you'll find coveted parking for multiple

  Shirley Carey Berkshire Hathaway HomeServices Knight & Gardner Realty

  322 Southard St, Key West, FL 33040
• 

  

  /48

  $4,998,000

  • 4 Beds
  • 5 Baths
  • 3,336 Sq Ft

  1006 Fleming St, Key West, FL 33040

  MOTIVATED SELLERS! Exceptional Old Town estate with pool, gardens, and 2 guest houses in the heart of Key West. This impeccable property blends timeless architecture with modern updates across three beautifully appointed structures. Behind a privacy wall & gate, the estate includes a grand main residence and two guest houses (both with kitchenettes), offering a total of four bedrooms and

  Terri Spottswood Truman & Co. (KW)

  1006 Fleming St, Key West, FL 33040
• 

  

  /22

  $898,000

  • 2 Beds
  • 1 Bath
  • 568 Sq Ft

  1218 Packer St Unit Rear, Key West, FL 33040

  Nestled in an X flood zone in Old Town , this lovely conch cottage has been well cared for, meticulously maintained and lightly used as a seasonal getaway. The two-bedroom, one-bath residence is fully furnished and move-in ready, offering a perfect blend of charm, comfort, and thoughtful design. Behind the private gate, the home immediately feels welcoming and serene, creating a true island

  Robert Donahue Key West Luxury Real Estate Inc (KW)

  1218 Packer St Unit Rear, Key West, FL 33040
• 

  

  /35

  $1,350,000

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

  97 Seaside North Ct Unit 97, Key West, FL 33040

  Quietly set within the gated Seaside Residences community, 97 Seaside Court North is a 2-bedroom, 3-full-bath, light-filled end-unit townhome offering privacy, volume, and a distinctly calm island feel. Built with solid masonry construction and impact-rated windows and doors, the home provides durability, security, and peace of mind. Solar panels paired with a Generac battery storage system

  Richard Patten Your Keys Real Estate, LLC

  97 Seaside North Ct Unit 97, Key West, FL 33040
• 

  

  /34

  $635,000 Open Sat 1PM - 3PM

  • 2 Beds
  • 2 Baths
  • 772 Sq Ft

  3675 Seaside Dr Unit 342, Key West, FL 33040

  Welcome to your private slice of paradise at 3675 Seaside Dr Unit 342 -- a desirable end unit offering added privacy, extra natural light, and a peaceful coastal setting. Thoughtfully designed, this bright and airy residence features open living spaces perfect for both everyday comfort and effortless entertaining.The well-appointed kitchen flows seamlessly into the dining and living areas,

  Joanne Allen Berkshire Hathaway HomeServices Knight & Gardner Realty

  3675 Seaside Dr Unit 342, Key West, FL 33040
• 

  

  /58

  $1,250,000

  • 4 Beds
  • 3 Baths
  • 2,664 Sq Ft

  1409 4th St, Key West, FL 33040

  Don't miss this rare opportunity to own a legal duplex on a spacious 10,000 SqFt corner lot! The main residence, solid CBS construction, offers 2 bedrooms, 2 bathrooms, and a generous 2,004 SqFt of living space. The open-concept layout features a large living room, a well-appointed kitchen with an adjoining dining area, and plenty of natural light. There's also a garage, laundry room, and

  Keys Team Bryant and Kat Expert Realty LLC (HQ)

  1409 4th St, Key West, FL 33040
• 

  

  /42

  $1,825,000 Open Sun 12PM - 2PM

  • 3 Beds
  • 4 Baths
  • 1,489 Sq Ft

  1120 Seminary St, Key West, FL 33040

  Nestled in the prestigious Casa Marina neighborhood, 1120 Seminary Street offers the quintessential Key West lifestyle with a perfect blend of charm, luxury, and tropical serenity. Located in an X Flood Zone. This enchanting bungalow boasts 2 bedrooms and 2.5 baths within the main home, where an open floor plan invites effortless entertaining and everyday living. Rich Dade County Pine accents on

  Henry Shultz Compass Florida, LLC

  1120 Seminary St, Key West, FL 33040
• 

  

  /30

  $820,000

  • 1 Bed
  • 1 Bath
  • 740 Sq Ft

  817 Eaton St Unit 1, Key West, FL 33040

  Old Town Condo Near Duval:Bright 1-bedroom, 1-bath condo located in the heart of Historic Old Town Key West. Featuring high ceilings and an open floor plan, this residence is filled with natural light. Just steps from Duval Street, dining, shopping, and entertainment. Ideal as a vacation rental, investment property, or personal island retreat.OWNERS MAY HAVE A PET WITH ASSOCIATION APPROVAL.

  Letisia Powell Robert Slack LLC

  817 Eaton St Unit 1, Key West, FL 33040
• 

  

  /31

  $499,500

  • 2 Beds
  • 2 Baths
  • 772 Sq Ft

  3635 Seaside Dr Unit 314, Key West, FL 33040

  Make an offer NOW and CATCH THE SUNSET every day from your third floor private balcony in this beautifully maintained 2-bedroom, 2-bathroom condo. It comes with a coveted carport (a $15,000 value alone) right next to the elevator, a separate storage unit and plenty of upgrades: NEW washer/dryer, NEW refrigerator, NEW water heater, NEW dishwasher, NEW oven/range, NEWLY painted. The split floor

  Heather Carruthers Berkshire Hathaway HomeServices Knight & Gardner Realty

  3635 Seaside Dr Unit 314, Key West, FL 33040
• 

  

  /50

  $1,695,000

  • 2 Beds
  • 2.5 Baths
  • 1,352 Sq Ft

  5960 Peninsular Ave Unit 105, Key West, FL 33040

  Experience coastal living at its finest in this stunning oceanfront condominium, where luxury meets comfort. Nestled along the pristine shoreline, this rare 2 bedroom, 2.5-bath end unit residence offers breathtaking views of the Atlantic Ocean, creating a serene backdrop for your everyday life. The open concept living area invites natural light, seamlessly blending indoor and outdoor spaces.

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

  5960 Peninsular Ave Unit 105, Key West, FL 33040
• 

  

  /37

  $4,750,000

  • 4 Beds
  • 5 Baths
  • 2,716 Sq Ft

  709 Eaton St, Key West, FL 33040

  Step into the enchanting world of Key West history at 709 Eaton Street, a meticulously preserved gem built circa 1847 in the iconic Seaport neighborhood. Historic charm and modern comfort, this home delivers 4 bedrooms, 4.5 baths, with 3 bedrooms, 3.5 baths conveniently located on the first level. The upstairs consists of the primary bedroom suite with an additional private study as well as a

  Will Langley Berkshire Hathaway HomeServices Knight & Gardner Realty

  709 Eaton St, Key West, FL 33040
• 

  

  /16

  $2,033,000

  • 2 Beds
  • 1 Bath
  • 888 Sq Ft

  1 & 2 Aronovitz Ln, Key West, FL 33040

  Rare opportunity on desirable Aronovitz Lane in the heart of Key West! This unique offering includes two properties being sold together, creating exceptional flexibility for investors, builders, or lifestyle buyers.The package includes a vacant lot with the ability to rebuild its original two-unit footprint, a true rarity in Key West, presenting an exceptional chance to develop new construction

  Alexa Morgan Buy The Keys

  1 & 2 Aronovitz Ln, Key West, FL 33040
• 

  

  /35

  $749,000

  • 2 Beds
  • 3 Baths
  • 900 Sq Ft

  18 Golf Club Dr, Key West, FL 33040

  Introducing this stunning new listing with the best lake view on the golf course, this meticulously maintained and updated 2-bedroom, 2 1/2-bathroom, 900 sqft townhome in Key West Golf Course community offers serene vistas of the 6th hole. Ideally positioned near the community entrance for easy access, this home features a host of impressive updates including a custom kitchen renovation, wood

  Solaris Gregory Expert Realty LLC (HQ)

  18 Golf Club Dr, Key West, FL 33040
• 

  

  /31

  $1,299,000

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

  414 Virginia St, Key West, FL 33040

  Lovely 3 bedroom 2 bath home in the midst of Old Town just off Duval St. Central AC with nice room sizes and great lot size. Flood Zone Z500. Ready to sell As-Is. Seller motivated but firm on price.

  Bernard Isler Isler Realty & Investments LLC

  414 Virginia St, Key West, FL 33040
• 

  

  /59

  $4,990,000

  • 4 Beds
  • 4 Baths
  • 2,441 Sq Ft

  720D Simonton St, Key West, FL 33040

  KEY WEST'S UNLIKELY SANCTUARY | DUAL TRANSIENT LICENSES While most Old Town properties embrace tropical pastels and wooden shutters, this exceptional compound stands as a bold architectural departure. With its striking modern aesthetic, raw concrete elements, and serene private courtyard, this is where minimalist design meets maximum investment potential, just one block from Duval Street. | THE

  The Spottswood Team Truman & Co. (KW)

  720D Simonton St, Key West, FL 33040
• 

  

  /58

  $1,800,000

  • 4 Beds
  • 3 Baths
  • 1,943 Sq Ft

  408 William St, Key West, FL 33040

  Blending timeless character and modern comfort this home is nestled on one of Old Town's most coveted streets. Come discover this captivating home steeped in rich history. The kitchen has been thoughtfully redesigned with granite counters, new stainless-steel appliances & now has an open layout that enhances both function and flow. The Richard Roberts home, originally transported from Green

  Terri Spottswood Truman & Co. (KW)

  408 William St, Key West, FL 33040
• 

  

  /16

  $392,000

  • 2 Beds
  • 3 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 a

  Gwendolyn Esbensen Berkshire Hathaway HomeServices Knight & Gardner Realty

  3314 Northside Dr Unit 46, Key West, FL 33040
• 

  

  /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
• 

  

  /31

  $1,495,000

  • 3 Beds
  • 2 Baths
  • 1,352 Sq Ft

  5960 Peninsular Ave Unit 110, Key West, FL 33040

  Wake up to panoramic Atlantic Ocean views from this spacious condo in Oceanside Marina. Located in a gated waterfront community, this residence offers a relaxed coastal lifestyle with an open layout, coastal breezes, and stunning open-water views. Currently setup as a 2-bedroom layout, but can easily be converted before closing to a 3-bedroom if the buyer desires. Owners enjoy resort-style

  Will Langley Berkshire Hathaway HomeServices Knight & Gardner Realty

  5960 Peninsular Ave Unit 110, Key West, FL 33040
• 

  

  /68

  $1,400,000

  • 3 Beds
  • 3 Baths
  • 1,392 Sq Ft

  31 Coral Way, Key West, FL 33040

  Active nightly vacation rental located just minutes from Old Town Key West; this beautifully maintained 3-bedroom, 3-bathroom home offers the perfect blend of resort-style amenities and island living.This home features an open-concept floor plan with vaulted ceilings, abundant natural light, and a well-appointed kitchen complete with brand new stainless steel appliances and granite countertops.

  Krystal Thomas eXp Realty LLC

  31 Coral Way, Key West, FL 33040
• 

  

  /39

  $1,475,000

  • 5 Beds
  • 3 Baths
  • 1,898 Sq Ft

  1707 George St, Key West, FL 33040

  Escape to your own tropical paradise in Key West with this stunning turnkey family home and guest cottage, perfectly designed for relaxed island living or a savvy investment opportunity. Tucked behind private off-street parking, the lushly landscaped and fully fenced yard sets the tone for this serene retreat. The single-story ranch-style main home has been completely renovated and offers four

  Dawn McComish Lokation Real Estate

  1707 George St, Key West, FL 33040
• 

  

  /44

  $2,785,000

  • 3 Beds
  • 4 Baths
  • 3,049 Sq Ft

  1006 Seminary St, Key West, FL 33040

  NEW PRICE: This exceptional turnkey three-bedroom, three bath and one half-bath residence is located in the prestigious Casa Marina neighborhood, one of Key West's most sought-after enclaves. Showcasing timeless Spanish Colonial architecture, the home offers a bright, open floor plan enriched with elegant architectural details and enchanting stained glass accents throughout.The main level is warm

  Elizabeth Chamberlain Truman & Co. (KW)

  1006 Seminary St, Key West, FL 33040
• 

  

  /43

  $2,999,000

  • 4 Beds
  • 4 Baths
  • 1,968 Sq Ft

  510 Margaret St, Key West, FL 33040

  510 Margaret Street and 3 Scheppens Lane deliver an unparalleled island retreat. Ideally positioned on one of the most coveted streets in the heart of Old Town, this light-filled 4BD/4BA compound offers both comfort and privacy. The beautifully updated 3BD/3BA main residence features restored Dade County Pine walls, striking hardwood floors, Verde granite countertops, Thermador stainless

  Brenda Donnelly Brenda Donnelly Real Estate LLC

  510 Margaret St, Key West, FL 33040
• 

  

  /45

  $1,243,000

  • 3 Beds
  • 2 Baths
  • 1,168 Sq Ft

  1713 Rose St, Key West, FL 33040

  Welcome to 1713 Rose Street! This is your chance to purchase a well-maintained 3/2 pool home in Mid Town West! As its namesake suggests, Rose is one of the sweetest streets in midtown. Two blocks from the beaches, it is nestled away with its three sister streets, in a quiet, serene neighborhood full of wonderful residents. A 5 minute walk to White Street Pier, Higgs Beach, Salute Restaurant,

  Dawn Gonet Berkshire Hathaway HomeServices Knight & Gardner Realty

  1713 Rose St, Key West, FL 33040
• 

  

  /55

  $3,999,000

  • 4 Beds
  • 3 Baths
  • 2,271 Sq Ft

  813 Thomas St, Key West, FL 33040

  NOW offered fully furnished! Located on a rare double lot in the coveted X flood zone, discover an extraordinary opportunity to own a luxurious sanctuary in the heart of Old Town Key West. Built in 2002 and a complete renovation in 2025, the furnished 3BD/2BA main home masterfully fuses island-contemporary style with timeless sophistication. Additional features include wrap-around porches,

  Brenda Donnelly Brenda Donnelly Real Estate LLC

  813 Thomas St, Key West, FL 33040
• 

  

  /21

  $699,000

  • 2 Beds
  • 1 Bath
  • 646 Sq Ft

  620 Thomas St Unit 291, Key West, FL 33040

  Perfectly situated second floor Shipyard unit is now available for sale. Front and back decks provide for a perfect spot for morning coffee or afternoon Happy Hours. Impact windows and doors provide peace and security. Brand new roof and fresh paint means no assessments and a wonderfully clean appearance. You can not beat this location as you are two blocks from Duval St and a very short walk to

  Mike Caron Keller Williams Key West Compass Realty

  620 Thomas St Unit 291, Key West, FL 33040
• 

  

  /52

  $875,000

  • 2 Beds
  • 2 Baths
  • 1,221 Sq Ft

  2601 S Roosevelt Blvd Unit 223C, Key West, FL 33040

  Well maintained 2BD/2BA condo that was converted from a 3BD for extra living space. Offering resort style amenities, and strong rental appeal. Unit features open living area, private balcony, impact windows and sliders. Ideal for fulltime residence, second home, or investment opportunity.located in a professionally managed waterfront community with two pools (heated), tennis courts, assigned

  Shirley Carey Berkshire Hathaway HomeServices Knight & Gardner Realty

  2601 S Roosevelt Blvd Unit 223C, Key West, FL 33040
• 

  

  /10

  $499,000

  • 2 Beds
  • 1 Bath
  • 644 Sq Ft

  6800 Maloney Ave Unit 20, Stock Island, FL 33040

  This 2-bedroom one bath manufacture home, is located in Harbour Shores a well run condominium association park with very reasonable fees of $200 a month. This home sits on one of the bigger lots with provides off street parking with its own private driveway. The park also offers boat docking at very good rates for owners with easy ocean access. The home has a newer roof and central air

  Louis Paez Coldwell Banker Schmitt Real Estate Co. (KW)

  6800 Maloney Ave Unit 20, Stock Island, FL 33040
• 

  

  /43

  $775,000

  • 2 Beds
  • 1 Bath
  • 732 Sq Ft

  828 White St Unit 1, Key West, FL 33040

  Located in the heart of Old Town Key West's sought-after White Street Gallery District, this beautifully renovated 2-bedroom, 1-bath condo offers the perfect blend of island charm, outdoor living, and investment potential. A rare highlight is the expansive private outdoor space, featuring two distinct areas: an open-air sun deck ideal for relaxing and entertaining, and a screened lanai with

  Michelle Blades Realty Executives Florida Keys Old Town

  828 White St Unit 1, Key West, FL 33040
• 

  

  /28

  $790,000

  • 2 Beds
  • 1 Bath
  • 1,292 Sq Ft

  2016 Fogarty Ave, Key West, FL 33040

  Welcome to 2016 Fogarty Avenue in Midtown Key West -- a charming 2-bedroom, 1-bath wood-frame home situated on a full 5,000 sq. ft. lot in one of the island's up-and-coming neighborhoods.Inside, vaulted ceilings create an airy sense of space, complemented by warm wood flooring throughout. The nicely appointed kitchen offers ample cabinetry and workspace, flowing easily into the main living area

  Kirksten Irick Preferred Properties (KW)

  2016 Fogarty Ave, Key West, FL 33040
• 

  

  /47

  $1,795,000

  • 3 Beds
  • 3 Baths
  • 2,205 Sq Ft

  421 United St, Key West, FL 33040

  This super cute historic Old Town Key West 2,205 sq. ft. Conch-style home is perfectly positioned just steps from famous Duval Street and one block from the ocean, South Beach, and the Southernmost Point. If you're seeking the best location in Key West--walkable, vibrant, and effortless--this property is unmatched. The sun-filled first floor showcases timeless Dade County pine, cherry floors, and

  Timothy Swanson The Agency Florida Keys

  421 United St, Key West, FL 33040

Showing Results 321 - 360, Page 9 of 10