Homes for Sale near Key West High School

• 

  

  

  /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
• 

  

  

  /55

  $374,000

  • 2 Beds
  • 1.5 Baths
  • 748 Sq Ft

  701 Spanish Main Dr Unit 543, Cudjoe Key, FL 33042

  Transient Rental Vacation Home.Welcome to your ultimate island getaway on Cudjoe Key! Step into this charming coastal oasis nestled on a spacious corner lot in the sought-after Venture Out community. This 2 bedroom, 1.5 bath retreat is the perfect blend of comfort and style that will transport you to a world of relaxation and tranquility. This income-producing home is an active vacation rental

  Kelly Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 543, Cudjoe Key, FL 33042
• 

  

  

  /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
• 

  

  

  /22

  $698,000

  • 1 Bed
  • 2 Baths
  • 836 Sq Ft

  1209 Truman Ave Unit 2, Key West, FL 33040

  Charming Old Town Condo in the Heart of Key West! Don't miss this beautifully updated and move-in ready 1-bedroom condo perfectly situated in the vibrant White Street Gallery District. This charming residence offers easy, low-maintenance living in one of the most walkable and desirable neighborhoods of Old Town Key West.Step outside your front door and enjoy being just moments away from local

  Ellen Gvili Ocean Sotheby's International Realty

  1209 Truman Ave Unit 2, Key West, FL 33040
• 

  

  

  /65

  $1,099,000

  • 4 Beds
  • 2 Baths
  • 1,428 Sq Ft

  1519 4th St, Key West, FL 33040

  Discover the perfect blend of comfort & convenience at 1519 4th Street; a spacious 4-bedroom, 2-bathroom retreat perfectly situated in Midtown Key West. Set on a 5,000 sq. ft. lot, this beautifully refreshed home offers everything you need to enjoy the quintessential Florida Keys lifestyle.Step inside to an inviting open floor plan that flows effortlessly from the kitchen to the living and dining

  Krystal Thomas eXp Realty LLC

  1519 4th St, Key West, FL 33040
• 

  

  /25

  $474,000

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft

  27973 Snapper Ln, Little Torch Key, FL 33042

  Welcome to your dream retreat by the sea! This beautifully renovated 2/2 offers the perfect blend of classic coastal charm and modern upgrades. Recently renovated with a new roof (2021), new doors and windows (2000), new AC units and updated paint throughout. This home is located in a serene waterfront community with an unlimited free-access boat launch located only minutes from the house. Enjoy

  Bill Vaught (REO Vaught Realty LLC Vaught Realty

  27973 Snapper Ln, Little Torch Key, FL 33042
• 

  

  /8

  $224,890

  • 2 Beds
  • 1.5 Baths
  • 780 Sq Ft

  29859 Overseas Hwy Unit A6, Big Pine Key, FL 33043

  Own a Piece of Paradise - A Renovator's Dream!Embrace the possibilities with this project home opportunity. Whether you're looking to renovate the existing structure or replace it with a modern stilt home, the choice is entirely yours.Property Highlights: Spacious Lot: Enjoy one of the larger lots in the area, offering plenty of room for creative outdoor designs.Home Features: A 2-bedroom,

  Elizabeth Greco-DeGrenier Florida Keys Realty, Inc.

  29859 Overseas Hwy Unit A6, Big Pine Key, FL 33043
• 

  

  /4

  $1,500,000

  • Land
  • 10.5 Acres
  • $142,857 per Acre

  169 Overseas Hwy, East Rockland Key, FL 33040

  10.5 Acre +/- Vacant Commercial Zoned ( C-2 ) Site on US #1 on Rockland Key , Bayside as you enter Key West. Approx. 1000 ft of Frontage on US #1 with 6.559 AC +/- of Upland filled from 5 ft to 9 ft elevation. $1,500,000.00 Price is Per Upland Acre. Existing billboard lease. Contact List agent for full package

  Brian Schmitt Coldwell Banker Schmitt Real Estate Co. (KW)

  169 Overseas Hwy, East Rockland Key, FL 33040
• 

  

  /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
• 

  

  /30

  $729,000

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft

  27 Riviera Dr, Key West, FL 33040

  Welcome to your own slice of paradise in beautiful Big Coppitt Key! Just 10 minutes from the vibrant energy of Key West, this bright and beautifully renovated 2-bedroom, 2-bath canal-front home offers the perfect blend of island serenity and coastal convenience.Situated on a quiet canal with direct access to the bay, this adorable tropical retreat is ideal for boaters, kayakers, and sunset

  Dawn McComish Lokation Real Estate

  27 Riviera Dr, Key West, FL 33040
• 

  

  /52

  $685,000

  • 3 Beds
  • 2 Baths
  • 1,076 Sq Ft

  31240 Avenue H, Big Pine Key, FL 33043

  Welcome to your slice of paradise in Big Pine Key! This beautifully updated 3-bedroom, 2-bath home offers move-in-ready comfort with thoughtful upgrades throughout. Step inside to a beautifully renovated kitchen complete with quartz countertops, soft-close cabinetry, and premium finishes. The home offers new luxury vinyl plank (LVP) flooring throughout, blending durability with coastal style. The

  Charity Coffman Brightwild Real Estate

  31240 Avenue H, Big Pine Key, FL 33043
• 

  

  /39

  $730,000

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

  74 Pelican Ln, Big Pine Key, FL 33043

  Completely remodeled property, 2024 roof, new floors, termite treatment done 2025, fully furnished, with an excellent location 30 minutes from Key West, restaurants, schools, beaches, recreational centers and everything you need for a quiet and pleasant life, all close.And it also has a completely habitable game room with independent entrance.If the buyer uses the seller's lender and qualifies,

  Yunior Molina My Realty Group, LLC.

  74 Pelican Ln, Big Pine Key, FL 33043
• 

  

  /18

  $1,395,000

  • 2 Beds
  • 3 Baths
  • 1,216 Sq Ft

  101 Front St Unit 8, Key West, FL 33040

  This beautifully updated Foundry townhome in the exclusive gated Truman Annex community is a dream come true! The floor to ceiling windows and doors at the entry allow sunshine to filter into the main floor living space creating a bright and airy space. The main floor has 11 foot ceilings and double French doors that open to the private front courtyard and porch. The open floor plan allows for an

  Shannon Maska Last Key Realty, Inc (KW)

  101 Front St Unit 8, 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
• 

  

  /46

  $870,000

  • 2 Beds
  • 2 Baths
  • 798 Sq Ft

  3625 Seaside Dr Unit 25105, Key West, FL 33040

  Transient Nightly Rental Just Listed! Come invest into Key West nightly vacation rentals with this affordable condo with great rental numbers.This perfect split floor layout with two (2) bedrooms and (2) bathrooms condo that overlooks the community shared pool for that amazing vacation location. Each bedroom has its own ensuite full bathroom. The kitchen overlooks the spacious living room filled

  Bobby Coe RE/MAX Keys Connection (KW)

  3625 Seaside Dr Unit 25105, Key West, FL 33040
• 

  

  /54

  $899,000

  • 2 Beds
  • 2 Baths
  • 640 Sq Ft

  701 Spanish Main Dr Unit 97, Cudjoe Key, FL 33042

  Luxurious Waterfront Living - Welcome to your perfect coastal oasis in the sought-after community of Venture Out! This contemporary high-rise boasts million-dollar views from every angle, including a screened patio for ultimate enjoyment. With an outside elevator providing easy access, this stunning home features a serene primary suite with stylish decor and a beautiful walk-in shower in the

  Jan Fritz Coldwell Banker Schmitt RE Co.

  701 Spanish Main Dr Unit 97, Cudjoe Key, FL 33042
• 

  

  /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
• 

  /2

  $1,125,000

  • Land
  • 0.86 Acre
  • $1,301,248 per Acre

  0 U S Route 1, Big Pine Key, FL 33043

  Seller will finance with one half down payment for ten years, Commercial zoning, Tier 1 lot.

  Barbara Eads Barbara Eads Realty Inc.

  0 U S Route 1, Big Pine Key, FL 33043
• 

  

  /4

  $31,000

  • Land
  • 0.14 Acre
  • $227,941 per Acre

  0 Adams Rd, Sugarloaf, FL 33042

  No RV's, no camping, no clearing, and most likely unbuildable. No utilities to property. Not surveyed. ROGO LETTER IN HAND FOR 1 ROGO POINT. This lot is for dedication to receive 1 Rogo Point, Buyer Verify with County. Being sold as-is. Include extra time in offers to verify marketable title and conduct due diligence. Owner/Agent.

  Carmen David Xcellence Realty

  0 Adams Rd, Sugarloaf, FL 33042
• 

  

  /36

  $1,850,000

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

  1011 Simonton St Unit 1, Key West, FL 33040

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

  Marc Ulanowski Equestrian Sotheby's International Realty

  1011 Simonton St Unit 1, Key West, FL 33040
• 

  

  /37

  $1,254,000

  • 2 Beds
  • 2 Baths
  • 1,099 Sq Ft

  1901 S Roosevelt Blvd Unit 202W, Key West, FL 33040

  This rare transiently licensed condo is designed to embrace tropical luxury exuding natural light, open concept, practicality and privacy thus creating a serene and inviting environment for you and your guests. Located at La Brisa, a gated condo community, just steps from the beach ,the updated and stylish unit lovingly named 'Serenity by the Sea' is the unforgettable retreat you have been

  Robert Donahue Key West Luxury Real Estate Inc (KW)

  1901 S Roosevelt Blvd Unit 202W, Key West, FL 33040
• 

  

  /23

  $795,000

  • Land

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

  An exclusive offering to purchase a protected deep water yacht slip near Key West proper.Slip measures per survey 100' x 25.7'....HOWEVER can accommodate up to 125' boat. (has 20'' steel tie off pilings approximately 60' from dock)Safe Harbour Marina is a deep water protected port and recreational marina with minimum14' depth.Originally constructed in the late 1950's and located in the heart of

  Jerry Hughes Old Town Realty

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

  

  /117

  $11,000,000

  • 6 Beds
  • 8 Baths
  • 4,894 Sq Ft

  1041 Buttonwood Dr E, Sugarloaf Key, FL 33042

  Masterpiece of Modern Strength & Luxury | Brand-New Concrete Waterfront Estate on Prestigious Sugarloaf Key!This extraordinary new construction stunner is engineered as a rare modern fortress-- built entirely of concrete, built to the most stringent hurricane-resistant codes, and designed for the discerning buyer who demands architectural excellence, security, and elevated coastal living. Set on

  Lisa Swanson The Agency Florida Keys

  1041 Buttonwood Dr E, Sugarloaf Key, FL 33042
• 

  

  /21

  $459,000

  • 1 Bed
  • 1 Bath
  • 454 Sq Ft

  1124 Catherine St Unit 201, Key West, FL 33040

  Charming 1-bedroom, 1-bathroom condo offering 454 square feet of living space. The condo boasts an open floor plan with hurricanes rated windows, one assigned parking spot and also located in the X Flood Zone. The property is just few a few blocks from vibrant Duval Street, known for entertainment and dining options and additionally, it's within walking distance to the dog park, beaches, wildlife

  The Spottswood Team Truman & Co. (KW)

  1124 Catherine St Unit 201, Key West, FL 33040
• 

  

  /24

  $2,340,000

  • 5 Beds
  • 3.5 Baths
  • 2,447 Sq Ft

  29176 Violet Dr, Big Pine Key, FL 33043

  Escape to paradise! 5BR/3.5BA gated home in the Keys. Bamboo floors, fresh paint, screen patio. Elegant accents. Lush landscaping, private pool, hot tub. 2 levels, full bar, gourmet kitchen, walk-out patio. Master w/ walk-in closet. Stargaze from wrap-around porch. Must see this private oasis!

  Cliff Glansen FlatFee.com

  29176 Violet Dr, Big Pine Key, FL 33043
• 

  

  /38

  $5,850,000

  • 6 Beds
  • 8 Baths
  • 3,010 Sq Ft

  421-423 Simonton St, Key West, FL 33040

  Two Transient Homes Now Available For Sale. Just one block off world-famous Duval Street, this rare property offers two homes - each 3 bedrooms, 3.5 baths and private pools. These have strong rental histories. These well-appointed residences blend island charm with modern comfort, featuring open-concept living areas, updated kitchens and private ensuite bedrooms. Thoughtfully designed for guest

  Will Langley Berkshire Hathaway HomeServices Knight & Gardner Realty

  421-423 Simonton St, Key West, FL 33040
• 

  

  /65

  $5,750,000

  • 6 Beds
  • 6 Baths
  • 3,751 Sq Ft

  906 Johnson St, Key West, FL 33040

  Experience the grandeur of this exceptional six bedroom, five and a half bath estate located on one of the most exclusive streets in Key West. A stunning wall of bougainvillea and the stately front porch welcome you to this 3,751 square foot property on an expansive 10,750 square foot lot that embodies historic Key West architecture. The main residence features four bedrooms, three and half baths

  Regan Butler Truman & Co. (KW)

  906 Johnson St, Key West, FL 33040
• 

  

  /13

  $1,899,000

  • 7 Beds
  • 6 Baths
  • 2,790 Sq Ft

  909 Grinnell St, Key West, FL 33040

  Rare opportunity to acquire SEVEN units in the X-Flood Zone in Old Town Key West. That's correct, seven market rate units! That's less than $272K per unit! Recent changes to IRS tax code (such as accelerated depreciation) can benefit RE Investors - ask your tax expert. Prime location, just 1/2 block from cemetery and 1/2 block off Truman Ave. Currently configured as 6 units (but City recognizes

  Walt Lee Berkshire Hathaway HomeServices Knight & Gardner Realty

  909 Grinnell St, Key West, FL 33040
• 

  

  /53

  $985,000

  • 2 Beds
  • 2 Baths
  • 888 Sq Ft

  701 Spanish Main Dr Unit 51, Cudjoe Key, FL 33042

  Panoramic Ocean Views W/ Transient Rental License! This beautifully updated and well-maintained stilt home offers 2 bedrooms and 2 bathrooms, large kitchen with all the necessities, panoramic ocean views, a private 35' concrete seawall for your boat and off street parking for your vehicle. This home has an open deck overlooking the crystal clear waters and a screened deck just waiting for you to

  Kim Babenzien Expert Realty LLC (HQ)

  701 Spanish Main Dr Unit 51, Cudjoe Key, FL 33042
• 

  

  /15

  $399,000

  • 2 Beds
  • 1 Bath
  • 684 Sq Ft

  27977 Coral Shores Rd, Little Torch Key, FL 33042

  This 2 bedroom 1 bath with a screened in covered porch mobile home on just over 4100 sqft waterfront lot with great boating access.

  Dasha Ray Conch Realty LLC (KW)

  27977 Coral Shores Rd, Little Torch Key, FL 33042
• 

  

  /61

  $899,000

  • 3 Beds
  • 2 Baths
  • 1,716 Sq Ft

  27332 St Martin Ln, Ramrod Key, FL 33042

  Welcome to Breezeswept Beach Estates-- In the heart of the Florida Keys! Here, boating, diving, and fishing are a way of life. This waterfront concrete block (CBS) 3-bed, 2-bath home sits on a deep, ocean-side canal just minutes to open water; Looe Key's clear blue reef is about a 15-minute boat ride away, and Key West is roughly 30 minutes by car. Thoughtfully updated for low-maintenance Keys

  Mark Gable Engel & Volkers Marathon

  27332 St Martin Ln, Ramrod Key, FL 33042
• 

  

  /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
• 

  

  /17

  $530,000

  • 1 Bed
  • 1 Bath
  • 525 Sq Ft

  1500 Seminary St Unit 5A, Key West, FL 33040

  Welcome to this charming 1-bedroom, 1-bathroom apartment nestled in the heart of Key West. Located on desirable Seminary Street, this cozy yet functional home offers a perfect mix of comfort, character, and convenience.Step inside to find an open living space with hard flooring throughout the living room, office nook, and bedroom, complemented by easy-to-clean tile in the kitchen and bath.

  Jaime Caballero Key West Vacation Properties & Realty, LLC (KW)

  1500 Seminary St Unit 5A, Key West, FL 33040
• 

  

  /26

  $725,000

  • 1 Bed
  • 1 Bath
  • 513 Sq Ft

  106 Southard St Unit 9, Key West, FL 33040

  The iconic condo called Brucie's Ocean Peek is now available for sale. Currently an active vacation rental it is the perfect spot for a Key West pied a terre,, it can be used for monthly or greater rental. Perfectly situated overlooking the tropically landscaped Shipyard Park, it is close to the heated salt water pool. A separate entrance leads you upstairs to a wonderfully furnished living and

  Mike Caron Keller Williams Key West Compass Realty

  106 Southard St Unit 9, Key West, FL 33040
• 

  

  /17

  $998,000

  • 3 Beds
  • 3 Baths
  • 1,400 Sq Ft

  17171 Seagrape Ln, Summerland Key, FL 33042

  RARE OPPORTUNITY HERE! This home is perfect for a DIY or Builder. Bring your imagination as it's located in very desirable location of Sugarloaf Shores where homes are over 2++ million dollars. It just needs a makeover but has great bones and many things you won't get now. Full 2 car garage with impact doors and shop. Legal downstairs bath. Large lot on 70' wide flow through canal. Bay views.

  Marie Howe Century 21 Circle - Key West

  17171 Seagrape Ln, Summerland Key, FL 33042
• 

  

  /49

  $908,000

  • 2 Beds
  • 2 Baths
  • 1,124 Sq Ft

  3667 S Seas St, Big Pine Key, FL 33043

  Discover your dream waterfront residence in the Florida Keys! Constructed with superior CBS building methods, featuring concrete floors, beams, and decorative railings, this home promises enduring quality. A full concrete seawall and robust 10k lb. boatlift offer convenient access to local sandbars, snorkeling spots, dining venues, and exceptional fishing grounds. The securely enclosed yard

  Scott Brisson KeyIsle Realty

  3667 S Seas St, Big Pine Key, FL 33043
• 

  

  /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
• 

  

  /42

  $650,000

  • Land

  22948 Drake Ln, Summerland Key, FL 33042

  Canal front-vacant lot is ROGO exempt and ready to build on. It corners Drake Lane's dead end and is second from Cudjoe Bay's open water: Views and more views. 70-foot concrete seawall with boat slip/basin and 10,000 pound boat lift make this the perfect location for boater/angler's new home. Previous house removed and lot is ready for your new vision. Electric was in place, buyer to verify FKAA

  Barbara Bowers Preferred Properties (KW)

  22948 Drake Ln, Summerland Key, FL 33042
• 

  

  /68

  $1,900,000

  • 4 Beds
  • 2.5 Baths
  • 1,994 Sq Ft

  27385 Saint Lucie Ln, Summerland Key, FL 33042

  Tropical Keys Oasis -- Waterfront Luxury Living -- Come experience this one-of-a-kind tropical oasis that feels like living at a Keys resort. Surrounded by lush landscaping, vibrant grass is the backdrop for nine coconut palms, five banana trees, two mango trees, and an avocado tree, this property bursts with natural beauty. Vibrant bougainvillea archways create a stunning entry to one of the

  Amedeo Belmonte William Raveis Real Estate

  27385 Saint Lucie Ln, Summerland Key, FL 33042
• 

  

  /44

  $849,000

  • 2 Beds
  • 3 Baths
  • 1,108 Sq Ft

  32 Hilton Haven Rd Unit 9, Key West, FL 33040

  Now is the time to make your move on this exceptional property. After careful repositioning, this home is now offered at an incredible new price-$849,000. creating a rare value in today's market. Remarkable Waterfront Retreat- 32 Hilton Haven #9, Key West, FL. Don't miss your chance - opportunities like this don't last... Welcome to an exclusive waterfront sanctuary in the private community of

  Barbara Crespo Keller Williams Key West Compass Realty

  32 Hilton Haven Rd Unit 9, Key West, FL 33040

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