Homes for Sale near Key West High School

• 

  

  

  /50

  $2,500,000 New Construction

  • 4 Beds
  • 3 Baths
  • 2,000 Sq Ft

  711 W Indies Dr, Summerland Key, FL 33042

  Stunning Brand New Open Water CBS Construction Home on beautiful Ramrod Key, FL. Minutes to the Atlantic Ocean and World Famous Looe Key the #1 Dive destination in the Continental US.Discover coastal living at its finest with this brand-new 4-bedroom, 3-bathroom home nestled on the sparkling open waters of Ramrod Key. Boasting 2,000 square feet of thoughtfully designed living space, this home

  Greg MacLaren Internet Realty of the Florida Keys

  711 W Indies Dr, Summerland Key, FL 33042
• 

  

  

  /26

  $669,000

  • 3 Beds
  • 2 Baths
  • 1,353 Sq Ft

  29030 Iris Dr, Big Pine Key, FL 33043

  This 3BR spacious canal front home with quick open water access is nestled at the end of a quiet dead-end street. Amidst lush vegetation, this property offers the ultimate sanctuary for those seeking privacy and a connection to the Keys lifestyle. 50ft concrete seawall with 10,000lb boat lift. This home boasts an inviting shaded deck creating the perfect outdoor space for relaxation and

  Justyn Ewald Expert Realty LLC (HQ)

  29030 Iris Dr, Big Pine Key, FL 33043
• 

  

  

  /4

  $1,150,000 Open House 1/04

  • 3 Beds
  • 2 Baths
  • 1,452 Sq Ft

  1018 Georgia St, Key West, FL 33040

  Investors Alert! Legal Duplex in Old Town Key West. This property just had an Extreme Makeover. new roof, new siding, new kitchens, new bathrooms., new sub flooring in the back apartment, new impact windows . An opportunity to own a rental Property in Kew West with great income flow. With all the upgrades the rent will be increased. Downstairs lock out units; the back unit will rent for $2500

  Diana Fiddes Coldwell Banker Schmitt Key Largo

  1018 Georgia St, Key West, FL 33040
• 

  

  /2

  $350,000

  • 2 Beds
  • 2 Baths
  • 980 Sq Ft

  37 Yardarm Rd Unit 1, Cudjoe Key, FL 33042

  This sale is for one 6000 square foot lot with a home in need of repairs or replacement.

  Joseph Ordini Keller Williams Key West Compass Realty

  37 Yardarm Rd Unit 1, Cudjoe Key, FL 33042
• 

  

  

  /12

  $299,000

  • Land

  5555 College Rd Unit 10, Key West, FL 33040

  Incredible chance to own a premier slip in the private/gated Sunset Marina. Located at the end of the Sailfish pier, this 50' by 20' slip allows stress free docking and direct open water access for a wide range of boats. The slip is equipped with its own metered water, electric, and a lockable dock box to store items. HOA fees cover access to parking, the heated pool, spa, and clubhouse. In the

  Mason Kelly Expert Realty LLC (HQ)

  5555 College Rd Unit 10, Key West, FL 33040
• 

  

  /28

  $980,000

  • 4 Beds
  • 3 Baths
  • 1,457 Sq Ft

  31441 Avenue F, Big Pine Key, FL 33043

  This solid all-concrete home, situated on a generous 10,000 sq ft double lot, offers the perfect blend of comfort and style for a growing family. Step into the open-concept living area with vaulted ceilings, creating an airy, welcoming atmosphere. The chef-inspired kitchen features beautiful quartz countertops and stainless steel appliances, perfect for cooking and entertaining. Tile floors

  Austin Kimbler Expert Realty LLC (HQ)

  31441 Avenue F, Big Pine Key, FL 33043
• 

  

  /20

  $1,295,000

  • 4 Beds
  • 2 Baths
  • 1,820 Sq Ft

  29678 Enterprise Ave, Big Pine Key, FL 33043

  Discover an outstanding opportunity in Big Pine Key with this canal-front, stilted duplex featuring two spacious 2 bedroom 1 bath residences and deep-water boating access. This is an exceptional boater's duplex in Pine Channel Estates where you can enjoy income and lifestyle in one place. Enjoy 75 feet of concrete dockage with a convenient step-down and retaining wall, all situated on a clean,

  Kristen Brenner/Margie Casey T Florida Keys Real Estate Group

  29678 Enterprise Ave, Big Pine Key, FL 33043
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  /61

  $1,875,000

  • 2 Beds
  • 2 Baths
  • 1,172 Sq Ft

  876 Gulf Dr, Summerland Key, FL 33042

  Coastal Haven in Summerland Key Cove Isles! Calling all boaters--this move-in-ready waterfront oasis sits on a premier deep-draft canal with quick access to both the Atlantic and Gulf! Extensively updated in 2025 with a new metal roof, spray foam insulation, interior and exterior paint, new LVP flooring, gutters, soffits, fascias, new pool deck, and Trex decking, this home radiates fresh coastal

  Lisa Swanson The Agency Florida Keys

  876 Gulf Dr, Summerland Key, FL 33042
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  /18

  $420,000

  • 2 Beds
  • 2 Baths
  • 1,310 Sq Ft

  256 Mars Ln, Key West, FL 33040

  Unlock the potential of this waterfront property just half a mile from the iconic Geiger Key Marina and Restaurant. Nestled on a generous 5,190 sq ft lot, this 1,310 sq ft mobile home offers direct canal access with a sturdy concrete seawall--ideal for swimming, fishing, kayaking, or simply soaking in the coastal lifestyle.The home is ready for renovations and personal touches. Whether you're

  Monique Thiel Sunshine State Realty Services

  256 Mars Ln, Key West, FL 33040
• 

  

  /49

  $1,875,000

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

  101 Front St Unit 23, Key West, FL 33040

  Completely renovated and move-in ready, The Foundry #23 in Key West's exclusive Truman Annex is a rare gem that blends historic charm with modern luxury. This beautifully updated townhome features custom Hansen & Bringle cabinetry throughout, quartz countertops, and brand-new appliances in the kitchen. The Primary Suite offers ample closet space and a redesigned bath with custom cabinetry and a

  Loren Rea Truman & Co. (KW)

  101 Front St Unit 23, Key West, FL 33040
• 

  

  /38

  $1,149,000

  • 2 Beds
  • 2 Baths
  • 1,316 Sq Ft

  1800 Atlantic Blvd Unit 410A, Key West, FL 33040

  Experience Luxury Living by the Sea.Welcome to your dream coastal retreat--this exquisite 2-bedroom, 2-bathroom luxury condominium offers stunning ocean views from the living area, both bedrooms, and your private balcony. Wake up to the sound of waves and bask in natural light that fills every corner of this beautifully upgraded home and end your day with nightly sunset views.Step inside to find

  Stacy Stahl Realty ONE Group Destination

  1800 Atlantic Blvd Unit 410A, Key West, FL 33040
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  /9

  $163,000

  • Land

  29859 Overseas Hwy Unit A-3, Big Pine Key, FL 33043

  ROGO EXEMPT - Buildable lot! Incredible opportunity to buy a piece of paradise in Florida keys! This residence offers a unique blend of coastal living and modern amenities. Appropriate for those seeking a tranquil retreat while still being conveniently close to local attractions and the beautiful waters of the Florida Keys. Discover the lifestyle you've been dreaming of here. Low HOA fee, just

  Steven Koleno Beycome of Florida, LLC

  29859 Overseas Hwy Unit A-3, Big Pine Key, FL 33043
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  /31

  $3,495,000

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

  1610 South St, Key West, FL 33040

  This British designer has spent over twenty years crafting contemporary properties in a luxurious Caribbean setting. Well-known for attention to detail and a commitment to sourcing the finest materials, this builder's constructions are exceptional. The spacious living room effortlessly merges with the outdoors upon opening the storm-proof sliding doors, creating a seamless transition between

  Rob Severin Rob Severin Real Estate Co

  1610 South St, Key West, FL 33040
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  /37

  $1,775,000

  • 7 Beds
  • 5 Baths
  • 2,236 Sq Ft

  1301 Atlantic Dr, Key West, FL 33040

  MOTIVATED SELLER. SELLER FINANCING OFFERED. This is an excellent INVESTMENT OPPORTUNITY. Located near the Casa Marina Neighborhood, this 6,370 square foot, corner lot, is completely fenced in and private. Plenty of room for parking. 7 bedrooms and 5 bathrooms with 2,236 sq ft of living space. This property has potential for either long term rentals/employee housing grossing nearly 10K per month

  Joyce Craul Expert Realty LLC (HQ)

  1301 Atlantic Dr, Key West, FL 33040
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  /41

  $1,035,000

  • 2 Beds
  • 2 Baths
  • 1,118 Sq Ft

  1606 Flagler Ave, Key West, FL 33040

  Modern Coastal Living Near Key West Beaches - Renovated 2BD/2BA, Impact Windows, Private Outdoor Oasis & Off-Street ParkingBeautifully renovated single-story 2BD/2BA home in Midtown Key West, just minutes to the beach and Edward B. Knight Pier. Features include an open-concept living area, updated kitchen with stainless appliances, beverage bar, and mobile island. The primary suite offers two

  Dustan Carpenter Berkshire Hathaway HomeServices Knight & Gardner Realty

  1606 Flagler Ave, Key West, FL 33040
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  /22

  $625,000

  • 2 Beds
  • 2 Baths
  • 1,128 Sq Ft

  35 Boundary Ln, Key West, FL 33040

  Your piece of paradise here in the lower keys only 9 miles from Kew West and all it has to offer! This is the fish camp you've been looking for or build your new home in paradise here. Spectacular quick deep-water access to the ocean! Many upgrades to this cozy bungalow.

  Marie Howe Century 21 Circle - Key West

  35 Boundary Ln, Key West, FL 33040
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  /98

  $3,249,500

  • 5 Beds
  • 5 Baths
  • 2,721 Sq Ft

  1114 Packer St, Key West, FL 33040

  X FLOOD ZONE! Luxurious Old Town Key West Family Compound with separate Guest House! Nestled in the heart of Key West's historic district, this impeccably remodeled property redefines island elegance. Situated in the coveted X Flood Zone, this home boasts an unparalleled location just steps from iconic Duval Street, world-class dining, vibrant galleries, and pristine beaches. Step inside to

  Will Langley Berkshire Hathaway HomeServices Knight & Gardner Realty

  1114 Packer St, Key West, FL 33040
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  /29

  $799,000

  • 1 Bed
  • 2 Baths
  • 650 Sq Ft

  616 Caroline St Unit 6, Key West, FL 33040

  Situated along one of Old Town's most storied corridors, residence #6 at 616 Caroline Street offers a refined Keys lifestyle just steps from the Historic Seaport, Duval Street dining, galleries, and marinas. Tucked within a boutique setting, this private upstairs home balances character and comfort with a bright, welcoming living area and an efficient layout that makes everyday living--and easy

  Jimmy Lane Island Life Realty Experts

  616 Caroline St Unit 6, Key West, FL 33040
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  /15

  $485,000

  5950 Peninsular Ave Unit 643, Key West, FL 33040

  Exceptional opportunity to own one of the few 50' x 22' liveaboard boat slips in all of Key West, located in the prestigious Oceanside Marina at Ocean's Edge Resort. This premium, deeded deep-water slip offers direct access to the Atlantic Ocean with a 9' control depth ideal for accommodating larger vessels and luxury yachts. Enjoy spectacular open water views in a secure, full-service marina

  Greg Dully RE/MAX All Keys Real Estate

  5950 Peninsular Ave Unit 643, Key West, FL 33040
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  /48

  $1,949,000

  • 3 Beds
  • 4 Baths
  • 1,828 Sq Ft

  807 Washington St Unit 101, Key West, FL 33040

  This unit in the Casa Marina Estates townhomes is unique. As an end unit, it is the only home with a westward exterior wall receiving natural light from all 3 sides. Its location in the quiet, desirable Casa Marina neighborhood is blocks from Higgs Beach and within a short walk to restaurants and nightlife. This comfortable home features an open floor plan with 3 bedrooms, 3 1/2 baths, private

  Jeffrey Dunaway Key West Realty, LLC (KW)

  807 Washington St Unit 101, Key West, FL 33040
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  /53

  $2,300,000

  • 8 Beds
  • 4 Baths
  • 750 Sq Ft

  2322 Seidenberg Ave, Key West, FL 33040

  Development Opportunity. (4) townhouse unit complex situated on a heavily landscaped 10,000 sq ft parcel. Comprised of (2) side by side duplexes legally subdivided as ( 4 ) individual, 750 sq ft licensed units, with (4) separate legal descriptions, parcel numbers, insurance policies, & utilities meters. At one time, there were four individual loans on each of the units as well.**** The only

  Raymond Capas Berkshire Hathaway HomeServices Knight & Gardner Realty

  2322 Seidenberg Ave, Key West, FL 33040
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  /24

  $1,174,000

  • 3 Beds
  • 2 Baths
  • 1,772 Sq Ft

  7 Boca Chica Rd, Key West, FL 33040

  ''Experience Florida Keys living at its best! This stunning 3 bedroom, 2 bathroom canal front home offers everything you need for a perfect coastal lifestyle. The open floor plan creates a spacious and inviting atmosphere, ideal for entertaining or relaxing with family. With impact windows and doors, you can enjoy peace of mind and energy efficiency.The home features a 2 car enclosed garage,

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

  7 Boca Chica Rd, Key West, FL 33040
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  /39

  $969,000

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

  437 Pirates Rd, Little Torch Key, FL 33042

  Now offered in the sought after Jolly Roger Estates, this beautifully maintained one owner, free-flowing canal front home is just 10 years old and move-in ready. Elevated and thoughtfully designed, the 1,296 sq. ft. residence features three bedrooms and two bathrooms with refined details such as crown molding, tray ceilings, tile showers, and an open-concept living area. A new metal roof was

  Jo Ann Cook Ocean Sotheby's International

  437 Pirates Rd, Little Torch Key, FL 33042
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  /3

  $60,000

  • Land

  Lot 10 Rainbow Beach, Big Torch Key, FL 33042

  Tier 1 lot available for ROGO Donation use only. This property cannot be built on and no RV use is permitted. The sale includes a ROGO Dedication Letter valued at 2 points, providing a valuable advantage in the Monroe County permit allocation system.

  Shanti Cope Coldwell Banker Schmitt Key Largo

  Lot 10 Rainbow Beach, Big Torch Key, FL 33042
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  /5

  $139,000

  • Land

  Lot 6 Date Palm Dr, Sugarloaf Key, FL 33042

  Tier 3 Lot.Discover the potential of this expansive 15,000 sq ft dry lot in Sugarloaf Key, just 20 minutes from Key West, FL. Ideal for creating your dream island retreat, this property offers ample space.

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

  Lot 6 Date Palm Dr, Sugarloaf Key, FL 33042
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  /7

  $399,000

  • Land

  2 Dolphin Rd, Key West, FL 33040

  ROGO Exempt lot just 10 minutes from Key West! This spacious lot is ideal for a family home or an investor looking to capitalize on strong rental potential due to its prime location.Enjoy close proximity to Geiger Key Marina & Restaurant, Geiger Key Beach, and convenient access to Big Coppitt Boat Ramp--less than a mile away! From there, it's a straight shot to local favorites like Snipes Key and

  Austin Kimbler Expert Realty LLC (HQ)

  2 Dolphin Rd, Key West, FL 33040
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  /51

  $1,420,000

  • 3 Beds
  • 2 Baths
  • 1,764 Sq Ft

  30890 Granada Ave, Big Pine Key, FL 33043

  Welcome to your tropical oasis--where the true spirit of the Florida Keys comes to life. This spacious 3-bedroom waterfront home blends casual island style with relaxed coastal living, offering 1,764 square feet designed for comfort and ease. High ceilings lined with tongue-and-groove wood immediately set the island tone as you enter the open living space. The kitchen flows seamlessly into the

  Sunnie San Lorenzo KeyIsle Realty

  30890 Granada Ave, Big Pine Key, FL 33043
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  /49

  $6,200,000

  • 4 Beds
  • 5 Baths
  • 5,180 Sq Ft

  30 Cannon Royal Dr, Key West, FL 33040

  European Elegance! Recently updated and freshly painted, this 4BD/5BA Mediterranean villa in gated Shark Key offers 5,180 SF with soaring ceilings, Viking kitchen, office, game room, and breathtaking Gulf views. Enjoy indoor-outdoor living with expansive decks, pool, fireplace, and multiple entertaining areas. Primary suite includes sitting area, wet bar, and private terrace. Impact

  Joanne Allen Berkshire Hathaway HomeServices Knight & Gardner Realty

  30 Cannon Royal Dr, Key West, FL 33040
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  /16

  $800,000

  • 2 Beds
  • 2 Baths
  • 912 Sq Ft

  47 Boundary Ln, Key West, FL 33040

  Owner will offer seller financing. INSURANCE NOT REQUIRED for financing. This home is ideally located on a canal with a 55-foot sea wall, with direct ocean access. This home is located off mile marker 9, a perfect location to be close to Key West, but not too close to the crowds. Enjoy deep water fishing, snorkeling and scuba diving right outside your back door. Boat launch less than a mile away.

  Jenny Murphy Keller Williams Key West Compass Realty

  47 Boundary Ln, Key West, FL 33040
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  /48

  $2,495,000

  • 2 Beds
  • 3 Baths
  • 1,350 Sq Ft

  105 Front St Unit 121, Key West, FL 33040

  Epitome of Paradise!There is an enveloping comfort, an ease and repose, that beckons one away from the world's cares and invites one to lounge, drift away, and dream in this gorgeous waterfront condominium.Enjoy a single level open floor plan with two bedrooms, two full baths and a convenient powder room.Exquisitely decorated to reflect the local island flavor with all new furniture and

  The Behmke Group Keller Williams Key West Compass Realty

  105 Front St Unit 121, Key West, FL 33040
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  /21

  $920,000

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

  27360 Saint Croix Ln, Summerland Key, FL 33042

  Enjoy the Keys lifestyle in one of the Lower Key's most desirable communities - Breezeswept! Here you'll enjoy island living with the convenience of being just a short drive to Key West. This waterfront home sits on a wide canal with 60 feet of concrete dock that includes one 15,000 boat lift, one davit set. The home is offered turnkey with all the furniture if you wish. The canal offers

  Terry Bush Bluescape Real Estate

  27360 Saint Croix Ln, Summerland Key, FL 33042
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  /22

  $300,000

  • Land

  5555 College Rd Unit 9, Key West, FL 33040

  Own your own 40' boat slip (LOA 45') in Sunset Marina, a wonderful, quiet & secure marina on the Gulf in Key West. Positioned at the end of a T-dock on Sailfish Pier, this is a deeded slip, so you own the bay bottom and have unparalleled access with direct deep-water ingress and egress to the Gulf & easy access to the Atlantic.Located on the leeward side of Key West, this marina offers the

  Terri Spottswood Truman & Co. (KW)

  5555 College Rd Unit 9, Key West, FL 33040
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  /43

  $1,299,000

  • 3 Beds
  • 4 Baths
  • 1,932 Sq Ft

  1409 Truman Ave, Key West, FL 33040

  Welcome to 1409 Truman Avenue, a stunning Key West Eyebrow home that combines historical charm with modern amenities. Key Features, Historical Architecture, Enjoy high ceilings, beautiful Dade County Pine throughout, an open staircase, all signature elements of this classic Key West home. Spacious Layout, The home boasts 3 bedrooms one being a large master bedroom with a walk in closet, each with

  Michael Sorah Truman & Co. (KW)

  1409 Truman Ave, Key West, FL 33040
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  /42

  $2,850,000

  • 3 Beds
  • 3 Baths
  • 1,432 Sq Ft

  1108 Curry Ln, Key West, FL 33040

  Experience elegant island living in this pristine home located on a quiet lane in the heart of Old Town Key West. This beautifully designed residence offers the perfect blend of timeless charm and modern luxury.Step inside the 3 bedroom, 2.5 bath main home where sophisticated finishes comfortable living spaces, and abundant natural light create an inviting atmosphere. The open layout flows

  Mitzi Krabill Truman & Co. (KW)

  1108 Curry Ln, Key West, FL 33040
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  /35

  $1,949,000

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

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

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

  The Spottswood Team Truman & Co. (KW)

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

  

  /51

  $837,500 Open House 1/03

  • 3 Beds
  • 2 Baths
  • 1,250 Sq Ft

  29115 Rose Dr, Big Pine Key, FL 33043

  Welcome to this meticulously maintained and updated move-in ready canal-front home that offers the perfect blend of comfort, style, and durability. Featuring an inviting open-concept floor plan, this home boasts three spacious bedrooms and two modern bathrooms, all enhanced by LVP flooring throughout. Built above flood level with just the right number of steps to climb, this home ensures both

  Dave Wiley Coldwell Banker Schmitt Real Estate Co. (KW)

  29115 Rose Dr, Big Pine Key, FL 33043
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  /62

  $1,189,000

  • 2 Beds
  • 2 Baths
  • 1,122 Sq Ft

  125 Sea Ln, Key West, FL 33040

  Stunning! Custom designed and built, elevated CBS home on a canal with an open ocean view. This is a must see. Thoughtfully planned and exquisitely maintained property. 125 Sea Ln is strength, functionality and beauty! Concrete construction with roll down, accordion & Bahama style shutters for the windows plus impact doors. Two bed, two bath, split floor plan has den and kitchen in middle of home

  Walt Lee Berkshire Hathaway HomeServices Knight & Gardner Realty

  125 Sea Ln, Key West, FL 33040
• 

  

  /33

  $399,950

  • 1 Bed
  • 1 Bath
  • 528 Sq Ft

  30170 Linda St, Big Pine Key, FL 33043

  Welcome to your charming new home! This delightful concrete 1-bedroom, 1-bathroom residence features a sturdy metal roof and is nestled on a generously sized, fully fenced lot, offering both comfort and privacy.Step inside to discover energy-efficient LED lighting throughout, complemented by an energy-efficient A/C system to keep you cool. The kitchen features a gas range, perfect for cooking

  Silvestri Team Jeanette & Janessa Silves Coldwell Banker Schmitt Key Largo

  30170 Linda St, Big Pine Key, FL 33043
• 

  

  /57

  $1,650,000

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

  25368 2nd St, Summerland Key, FL 33042

  Experience the perfect blend of character, durability, and Keys style at this quintessential cottage on the oceanside of Summerland Key. This thoughtfully crafted home welcomes you with the warmth of original Miami-Dade cypress floors and soaring ceilings that fill the interior with a sense of openness and timeless charm. Designed for peace of mind, the property boasts a metal roof, Hardie board

  Ally Kelley Ocean Sotheby's International

  25368 2nd St, Summerland Key, FL 33042

Showing Results 241 - 280, Page 7 of 18