Homes for Sale near Monroe County School District Virtual Instruction Program

• 

  

  

  /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! Renovations in progress. 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

  Walt Lee Berkshire Hathaway HomeServices Knight & Gardner Realty

  909 Grinnell St, Key West, FL 33040
• 

  

  /2

  $2,500

  5950 Peninsular Ave Unit 640, Key West, FL 33040

  Prestigious boat slip for rent at Ocean's Edge Marina, suitable for boats up to 50FT located on the North pier with ample water access boasting a 6ft control depth. Features include a nearby fuel station and access to the hotel pool for tenants. Ideal for water enthusiasts seeking a premium marina experience. Daily, monthly or long term rentals available. Air bnb's or houseboats are not allowed.

  Hana Tomita Berkshire Hathaway HomeServices Knight & Gardner Realty

  5950 Peninsular Ave Unit 640, Key West, FL 33040
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  /29

  $1,195,000

  • 3 Beds
  • 2 Baths
  • 1,052 Sq Ft

  2911 Seidenberg Ave, Key West, FL 33040

  Welcome to your dream home in the heart of Key West's MidTown! This beautifully updated 3-bedroom, 2-bathroom residence blends modern comfort with island charm. Step inside to a spacious, open-concept living area designed for both relaxing and entertaining. The true highlight is the private backyard oasis — featuring a sparkling pool surrounded by fresh tropical landscaping, an expansive deck,

  Terrance Sullivan Buy The Keys (KW)

  2911 Seidenberg Ave, Key West, FL 33040
• 

  

  

  /55

  $1,245,000

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

  243 Golf Club Dr, Key West, FL 33040

  Beautifully maintained Golf Club home overlooking the 17th hole in the Sanctuary. This home is located on one of the largest lots in the development. New flooring upstairs, a new cooktop stove, a new kitchen sink, new light fixtures, and freshly painted exterior within the past 3 years. The home features a private carport for two vehicles and a detached storage unit. The Key West Golf Club

  Jessica Prescott Coastal Collection Real Estate Inc.

  243 Golf Club Dr, Key West, FL 33040
• 

  

  

  /85

  $12,500,000

  • 5 Beds
  • 5.5 Baths
  • 5,485 Sq Ft

  94 Driftwood Dr, Key West, FL 33040

  Where the essence of the Florida Keys meets refined coastal luxury, 94 Driftwood Drive stands as a rare bayfront sanctuary in coveted Key Haven. Just moments from the vibrancy of Key West, this residence offers a lifestyle defined by serenity, sophistication, and seamless access to world-class culture, cuisine, and adventure. Framed by spectacular water views from every room, the home's

  Eric Rizzo Ocean Sotheby's International Realty

  94 Driftwood Dr, Key West, FL 33040
• 

  

  /23

  $844,000

  $5K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,342 Sq Ft

  1425 Eliza St, Key West, FL 33040

  3 bedroom single-family home offering the opportunity to add a second bathroom within the existing roofline. Relax on the covered front porch and enjoy the Key West lifestyle. The private backyard provides space for a pool or outdoor entertaining. A great chance to renovate and make this home your own.

  Sean Farrer, P.A. Coastline R.E. & Property Mgmt. (KW)

  1425 Eliza St, Key West, FL 33040
• 

  

  /34

  $645,000

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

  28E 12th Ave, Key West, FL 33040

  This three-bedroom, two-bath elevated CBS home sits on a fully fenced 3,570-square-foot lot with a practical, well-proportioned layout that makes every inch count. The primary suite has an ensuite bath, while the two guest bedrooms share a second full bath. The property is fully fenced and features a carport & off street parking. This is the kind of home you put your stamp on. The bones are

  Krystal Thomas eXp Realty LLC Southernmost Branch

  28E 12th Ave, Key West, FL 33040
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  /36

  $2,895,000

  • 4 Beds
  • 4.5 Baths
  • 3,220 Sq Ft

  1320 South St, Key West, FL 33040

  Built in 2008, this expansive 3,220 sq ft residence sits on a nearly 5,000 sq ft lot and offers the perfect blend of comfort, style, and location. Centrally situated, you're just moments from beautiful beaches, top-tier dining, vibrant bars, museums, and all the attractions the area has to offer.Upstairs features three generously sized bedrooms, each with its own en suite bathroom and walk-in

  Daniel Skahen Preferred Properties (KW)

  1320 South St, Key West, FL 33040
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  /25

  $1,286,000

  • 5 Beds
  • 3 Baths
  • 1,752 Sq Ft

  2515 Staples Ave, Key West, FL 33040

  Fully renovated duplex offering immediate income and long-term upside in the heart of Mid-Town Key West. This property delivers the flexibility that today's buyer-investors want, offering a primary residence with income, a vacation retreat, or a pure investment opportunity. Live in one unit while generating strong rental income from the other or maximize returns with two income streams.

  Ea Ruth Loffreno Real Estate

  2515 Staples Ave, Key West, FL 33040
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  /54

  $1,450,000

  • 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
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  /2

  $1,300,000

  • 7 Beds
  • 5 Baths
  • 2,957 Sq Ft

  2016 Roosevelt Dr, Key West, FL 33040

  Builder/Contractors Dream ! Rare 4 unit new development opportunity, 7,000 square ft lot available in Midtown Key West.

  Richard Weston Weston Premier Realty, Inc

  2016 Roosevelt Dr, Key West, FL 33040
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  /3

  $825,000

  • Land
  • 6,000 Sq Ft
  • $5,989,500 per Acre

  3705 Eagle Ave, Key West, FL 33040

  **NOW OFFERING OWNER FINANCING** Build your Key West dream from the ground up! This rare, vacant 6,000sf lot sits on one of the most desirable blocks of Eagle Avenue in New Town - an established, residential neighborhood known for its tranquility and convenience. With beneficial use already approved by the City of Key West Planning Department, the groundwork is in place to move forward with

  Terri Spottswood Truman & Co. (KW)

  3705 Eagle Ave, Key West, FL 33040
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  /17

  $869,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft

  2515 Staples Ave Unit A, Key West, FL 33040

  Fully renovated and move-in ready, this property delivers the flexibility that today's buyer-investors want, offering a primary residence, a vacation retreat, or an investment opportunity. Unit A features a spacious 3-bedroom, 2-bath layout with two entrances, a private Porch and Patio with lawn, strong rental demand. Short-term rentals restricted to 28 days. Extensively updated in 2020-2021 for

  Ea Ruth Loffreno Real Estate

  2515 Staples Ave Unit A, Key West, FL 33040
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  /37

  $860,000

  • 2 Beds
  • 2 Baths
  • 1,339 Sq Ft

  3365 Flagler Ave, Key West, FL 33040

  Welcome to 3365 Flagler Avenue, a beautifully updated and meticulously maintained 2 bed, 2 bath townhome in the Villas of Key West. Built of solid CBS construction and spanning 1,339 square feet, this two-story home is located above flood, has off-street parking and no HOA fees.The interior features a bright, open floor plan with Saltillo tile floors, updated lighting, and smart home

  Becky Newman Better Homes and Gardens Real Estate Destinations

  3365 Flagler Ave, Key West, FL 33040
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  /34

  $1,025,000

  • 2 Beds
  • 2 Baths
  • 1,311 Sq Ft

  1800 Atlantic Blvd Unit 427C, Key West, FL 33040

  This spacious two-bedroom, two-bath penthouse condo boasts a stunning balcony with ocean views, making it the perfect place to relax and enjoy the breathtaking scenery. The beautifully designed kitchen features a breakfast bar, granite countertops, and stainless steel appliances, making it a chef's dream come true. The stunning living room and dining room are flooded with natural light, creating

  Tommy Mack Coastal Collection Real Estate Inc.

  1800 Atlantic Blvd Unit 427C, Key West, FL 33040
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  /36

  $2,299,999

  New Construction Open Thu 10AM - 12PM

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

  1716 Laird St, Key West, FL 33040

  This brand new home is a beauty! Completed in 2025, this 2 story , Cat 5 home, with Impact windows and doors, Hardiboard siding , has 4 Bedrooms, 3 bathrooms, a large spacious Living/ Dining/ Kitchen occupying the majority of the First level, with a downstairs bedroom and bath. The second floor has 3 bedrooms and 2 baths. The outside - back yard is incredible, with about a 30 foot long chickee

  Elaine Coyle Keller Williams Key West Compass Realty

  1716 Laird St, Key West, FL 33040
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  /22

  $1,000,000

  $300K PRICE DROP

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

  6810 Front St Unit SNL13&B4SA, Stock Island, FL 33040

  This is a unique opportunity to own 1200 sq feet of beautifully renovated condo space along with a 40nft deep water slip. The unit comes with one assigned off street parking space. Taxes, water, insurance, building and common area maintenance are covered under the dues.Weekly vacation rentals allowed for the condo.

  Marc Ulanowski Equestrian Sotheby's International Realty Inc.

  6810 Front St Unit SNL13&B4SA, Stock Island, FL 33040
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  /51

  $1,775,000

  Open Sun 1PM - 3PM

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

  101 Front St Unit 23, Key West, FL 33040

  Completely renovated and being offered turn-key, 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

  Loren Rea Truman & Co. (KW)

  101 Front St Unit 23, Key West, FL 33040
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  /50

  $1,300,000

  • 3 Beds
  • 2 Baths
  • 784 Sq Ft

  611 Grinnell St Unit 4, Key West, FL 33040

  Embrace the enchantment of Old Key West Charm in this Beautifully Updated Historic Conch 3 Bedroom-2 Bath Home, featuring a Tropical Landscaped community Pool creating ultimate relaxation. This timeless Conch Cottage is nestled in a secure gated compound of six Key West Style Cottages. Low HOA Fee $288 Monthly includes Pool and Landscaping maintenance. This home is in an X500 Flood Zone, Banks do

  Daniel Cloud Water Vista Realty, Inc.

  611 Grinnell St Unit 4, Key West, FL 33040
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  /19

  $6,000

  • 2 Beds
  • 2.5 Baths
  • 728 Sq Ft

  1002 Thomas St, Key West, FL 33040

  Located in the heart of Old Town Key West! Walk, bike or drive your golf cart to famous restaurants, bars, tourist attractions and beaches. This 2 bedroom 2.5 bath home is being rented annually, fully furnished and includes two of street parking spaces, a rare find in Old Town! OWNER PAYS water, electric trash and internet. One small dog is allowed upon approval by the owner and for a

  Jessica Prescott Coastal Collection Real Estate Inc.

  1002 Thomas St, Key West, FL 33040
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  /24

  $1,175,000

  $175K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,260 Sq Ft

  115 Front St Unit 102, Key West, FL 33040

  HARBOUR PLACE | TRUMAN ANNEX. This waterfront gated community boasts amazing ocean views from the pool and patio areas. Unit 102 has an open floor plan that seamlessly connects the dining and living areas, leading out to a private balcony. This residence features two bedrooms, including a spacious primary suite with a large walk-in closet and a full bathroom. The second bedroom is also generous

  Bascom Grooms Bascom Grooms Real Estate (KW)

  115 Front St Unit 102, Key West, FL 33040
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  /38

  $1,225,000

  • 2 Beds
  • 2.5 Baths
  • 1,240 Sq Ft

  1075 Duval St Unit R10, Key West, FL 33040

  Tucked away in the heart of Old-Town Key West!Welcome to 1075 R10 Duval Street offers the perfect blend of privacy, island charm, and effortless living. This thoughtfully designed 2-bedroom, 2.5-bathroom residence features 1,240 square feet of living space and is ideally positioned in a quiet, off-the-street setting while remaining just moments from shopping, dining, beaches, Boating and all that

  Bobby Coe RE/MAX Keys Connection (KW)

  1075 Duval St Unit R10, Key West, FL 33040
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  /40

  $1,099,000

  $2K PRICE INCREASE

  • 1 Bed
  • 1 Bath
  • 666 Sq Ft

  1445 S 1445 Roosevelt Blvd Unit 411, Key West, FL 33040

  Fully furnished TRANSIENT LICENSED condos in Coconut Mallory Marina & Resort — listed separately but offered together as a rare investment package. Known as The Poolside Cottages (Units #411 & #412), these charming 1BR/1BA cottages are conveniently located near the pool and feature private patios, vaulted ceilings, updated interiors, and sleeping space for up to six guests per unit. Each unit is

  Jonathan Minerick Homecoin.com

  1445 S 1445 Roosevelt Blvd Unit 411, Key West, FL 33040
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  /37

  $1,689,000

  $111K PRICE DROP

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

  21 Bougainvillea Ave, Key West, FL 33040

  Once in a lifetime opportunity rare T-Channel Home 90 seconds to open water. Well Built Concrete Block Concrete Sumptuous 500' Living Room View. Garage and Room for Your RV Seize-The-Day Deep water Key Haven waterfront home with immediate Gulf and Atlantic access just minutes from Key West. Located at 21 Bougainvillea Avenue in Key Haven, this rare boating property offers 62 feet of solid

  Robin Nilsson Keller Williams Key West Compass Realty

  21 Bougainvillea Ave, Key West, FL 33040
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  /12

  $575,000

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

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

  Experience the relaxed charm of island living in this nicely updated third-floor 3-bedroom, 2-bath condo located in the highly desirable Las Salinas community. Filled with natural light, the open-concept layout creates a bright and welcoming atmosphere that feels comfortable from the moment you walk in. The thoughtfully designed kitchen features quartz countertops, stainless steel appliances, and

  Monika Rydzak eXp Realty LLC KW Branch

  3930 S Roosevelt Blvd Unit N304, Key West, FL 33040
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  /38

  $1,799,000

  • 7 Beds
  • 5 Baths
  • 2,349 Sq Ft

  800 Elizabeth St, Key West, FL 33040

  Tucked into one of Old Town's most peaceful and charming pockets, this unique multi-unit property offers the perfect blend of classic Key West character and flexible living. At 800 Elizabeth Street, you'll find a quintessential two-story Conch home featuring 5 bedrooms and 3 bathrooms, soaring ceilings, and timeless architectural details. Start your mornings on the inviting front porch and wind

  Jenny Perry Preferred Properties (KW)

  800 Elizabeth St, Key West, FL 33040
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  /33

  $780,000

  • 2 Beds
  • 2.5 Baths
  • 900 Sq Ft

  25 Kingfisher Ln, Key West, FL 33040

  Tucked away on a quiet private cul-de-sac in the highly sought-after Key West Golf Club community, 25 Kingfisher Lane offers a rare blend of privacy, convenience, and island charm. With easy parking and an exceptional setting, this light-filled residence stands out from the rest.This beautifully positioned home features an expansive wraparound deck, larger than most, along with additional windows

  Terri Spottswood Truman & Co. (KW)

  25 Kingfisher Ln, Key West, FL 33040
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  /43

  $2,595,000

  $205K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,049 Sq Ft

  508 Grinnell St, Key West, FL 33040

  Traditional key West home impeccably maintained, boasts three bedrooms, three full baths with plenty of closets throughout the home. Large private lot with a heated pool featuring a waterfall. Nice size cabana room that has a/c and heat with ample closet space can be a fourth bedroom. This home has large rooms for entertaining, quaint front porch and off street parking. A true treasure.

  Marc Ulanowski Equestrian Sotheby's International Realty

  508 Grinnell St, Key West, FL 33040
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  /18

  $3,450

  • 2 Beds
  • 2 Baths
  • 1,175 Sq Ft

  Unlisted Address

  Fully furnished La Brisa condo available through December 15, 2026. Electric, water and wi-fi included up to $200 per month. Washer and dryer in the unit. Covered carport, storage unit, central a/c, salt ponds view. Secured entry and building. La Brisa has an EV charging station, car wash area, tennis/pickleball court, barbecues, heated pool and hot tub and saunas No smoking, no pets, background

  Suzanne Washburn Coldwell Banker Schmitt Real Estate Co. (KW)

  Unlisted Address
• 

  

  /14

  $1,196,000

  $103K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 943 Sq Ft

  719 Elizabeth St, Key West, FL 33040

  Location, Location, Location! Old Town in X-Flood Zone on Solaris Hill with Off Street Parking! Quintessential conch cottage has a cozy front porch & has been in the same family for decades. All wood structure shows a glimpse of wood boards behind the existing interior paneling. This is believed to be the much-desired Dade County Pine. Roof and main electrical panel replaced (w/ permits) in 2014.

  Walt Lee Berkshire Hathaway HomeServices Knight & Gardner Realty

  719 Elizabeth St, Key West, FL 33040
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  /43

  $3,600,000

  • 4 Beds
  • 3 Baths
  • 1,920 Sq Ft

  514 Emma St, Key West, FL 33040

  514 Emma is a wonderful single-family home located in Truman Annex. The first floor features a large, updated chef's kitchen with double wall ovens, double refrigerator/freezers and a large island. There is a guest bedroom, and a full bathroom as well as a dining area. French doors in the living area, open to the large rear porch and pool. There is a carport on the rear of the property, PLUS a

  Behmke The Compass Realty (KW)

  514 Emma St, Key West, FL 33040
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  /17

  $775,000

  • 2 Beds
  • 2 Baths
  • 862 Sq Ft

  1004 Watson St Unit 2, Key West, FL 33040

  Positioned in the coveted X flood zone, this 2 bedroom 2 bath residence is a refined expression of Key West's enduring charm. As one of only two units in a boutique townhome setting, it offers a rare sense of privacy and ease. Granite countertops and stainless-steel appliances elevate the efficient galley kitchen. At the heart of the home, the primary suite serves as a tribute to island heritage,

  Brenda Donnelly Brenda Donnelly Real Estate LLC

  1004 Watson St Unit 2, Key West, FL 33040
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  /9

  $20,000

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

  3675 S Roosevelt Blvd Unit week 43, Key West, FL 33040

  Selling week 42 and 43. High Tourist season. Fantasy Fest and Halloween. These weeks can be sold as deeded weeks or as points to add to an existing portfolio. Across from Smathers beach. There is an ocean view and amazing Sunrise views. Princess Balcony. 2 Bedroom Villa.

  Jenny Murphy Keller Williams Key West Compass Realty

  3675 S Roosevelt Blvd Unit week 43, Key West, FL 33040
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  /42

  $598,000

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

  3930 S Roosevelt Blvd Unit E308, Key West, FL 33040

  Renovated 3-bedroom 2-bathroom unit with a peak a boo view of the Atlantic from the 3rd floor. The largest floorplan in Las Salinas. New paint, newer appliances and flooring. Granite countertops, stainless steel appliances, custom closets with additional storage, crown molding and more. Las Salinas is located across the street from the Atlantic, ideal for enjoying the sunrise. Footsteps from the

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

  3930 S Roosevelt Blvd Unit E308, Key West, FL 33040
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  /33

  $839,000

  • 2 Beds
  • 2 Baths
  • 944 Sq Ft

  1124 Olivia St Unit 321, Key West, FL 33040

  *** BEST PRICED 2/2 CONDO IN OLD TOWN *** Lionsgate community, heart of Old Town, one of Key West's most coveted small communities, known for its heated saltwater pool, lush tropical landscaping, and neighbors who actually know each other.Unit 321 sits on the second floor with vaulted ceilings, exposed beams, and an open layout that lives significantly larger than 944 sq ft. The kitchen and

  Juan Benitez Benitez Keller Williams Key West Compass Realty

  1124 Olivia St Unit 321, Key West, FL 33040
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  /28

  $1,349,900

  $49K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,434 Sq Ft

  928 United St, Key West, FL 33040

  FLIP FLOPS INLCUDED! Some homes are just addresses. This one is a lifestyle. Tucked into the heart of Old Town Key West, this beautiful historic Conch home is wrapped in the warmth of original Dade County pine and rich hardwood floors -- the kind of craftsmanship that simply isn't built anymore. The main house offers three bedrooms and a fully renovated bath, anchored by a large kitchen with

  Dawn McComish LPT Realty, LLC

  928 United St, Key West, FL 33040
• 

  /2

  $375,000

  Unlisted Address

  Great opportunity and location to own 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
• 

  

  /7

  $899,000

  • 1 Bed
  • 1 Bath

  2330 Staples Ave, Key West, FL 33040

  Discover a rare investment opportunity in the heart of Key West. This spacious corner duplex lot at 2330 Staples St and 1428 6th St offers incredible potential with two separate addresses and alley access for three convenient side entrances. The large lot features a charming, spacious cottage complete with a full kitchen, a bedroom with ample closet space, a stylish bathroom, and an attached

  Giancarlo Espinosa Virtual Realty Group FL Keys Inc

  2330 Staples Ave, Key West, FL 33040
• 

  

  /38

  $749,900

  • 2 Beds
  • 1 Bath
  • 780 Sq Ft

  1825 Venetia St, Key West, FL 33040

  If you've been searching for a move-in ready slice of Key West in the heart of Midtown, 1825 Venetia Street delivers. This renovated 2-bedroom, 1-bath concrete block home sits on a fully fenced lot with a private tropical backyard designed for island living -- complete with a covered deck, lanai, outdoor shower, fruit trees, and multiple sitting areas that make the outdoors feel like an extension

  Jimmy Lane Island Life Realty Experts

  1825 Venetia St, Key West, FL 33040
• 

  

  /3

  $300,000

  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

Showing Results 281 - 320, Page 8 of 10