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5950 Peninsular Ave Unit 693 & 694, Stock Island
$2,550,000
617986 MLS
Discover the largest boat slip in Key West's premier marina. This expansive 142.5-foot live aboard slip, located at the end of the T-Head in Oceanside Marina, offers unmatched convenience, security, and direct deep-water ocean access—ideal for large yachts or luxury vessels. In the past this slip has been home to yachts up to 130 feet in length. It can also be used for multiple vessels. As part of the Oceans Edge Resort, owners and guests enjoy world-class amenities, including six resort pools, on-site dining, a fitness center, and a variety of games and a dog park. The marina itself provides everything you need for effortless docking and maintenance, including pump-out service, Wi-Fi, water, electric hookups, and a fuel dock. This rare offering combines luxury, accessibility, and resort-style living—perfect for those seeking the ultimate Key West boating experience.

5950 Peninsular Ave Unit 693 & 694, Stock Island

5635 Macdonald Ave, Stock Island
$1,700,000
2 Beds ⋅ 3 Baths ⋅ 616957 MLS
Imagine a home that's as playful and dynamic as you are. An indoor space big enough to provide you with the freedom to play, create, and unwind — all under your own roof. A place that's more than just a residence — it's a reflection of how you love to live in a setting where space is a luxury. You might find yourself lounging in your garage and the smell of aged leather with a hint of motor oil hangs subtly in the air- not unpleasant, but nostalgic. You're sipping something smooth, low light casting warm glows off chrome fenders and polished wood. The space around you isn't just a living room - it's a personal museum, a garage gallery, a grown-up playhouse built with passion. The building is 2,730 sq. ft. total; Upstairs Apartment with 2 bed/2 baths is 805 sq. ft.; Garage with full bath is 1,925 sq. ft. Built in 2019 above flood and to withstand 180 MPH wind standards. Owners are licensed Real Estate agents.

5635 Macdonald Ave, Stock Island

5960 Peninsular Ave Unit 105, Stock Island
$1,450,000
2 Beds ⋅ 3 Baths ⋅ 618324 MLS
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. Enjoy panoramic ocean views through floor-to-ceiling impact windows, perfect for entertaining or simply soaking in the beauty of the sea. The heart of the home features a gourmet kitchen with top-of-the-line Viking appliances, ensuring that culinary enthusiasts can create gourmet meals with ease. Sleek granite & quartz countertops and custom cabinetry provide both style and functionality. Elegant Living Spaces with beautiful African Mahogany hardwood floors flow throughout the main living areas, adding warmth and sophistication. The living room is designed for relaxation, complete with modern fixtures and tasteful accents. Each of the bedrooms offers ample space, with the master suite boasting a huge walk-in closet and an en-suite bathroom with an ocean view. The bathrooms are outfitted with high-end finishes. Outdoor Oasis. Step onto your private balcony to enjoy morning coffee or sunset cocktails while listening to the soothing sounds of the waves. The condo complex also features access to resort-style amenities, including a heated pool, hot tub and direct marina access. Located in a sought-after community, this gated condo places you close to fine dining, shopping, and recreational activities, allowing you to fully immerse yourself in the vibrant coastal lifestyle. This luxurious oceanfront condo is a rare find, combining elegance, comfort, and breathtaking views. Prewired for surround sound and surveillance. 2 covered parking spaces convey. Whether you seek a permanent residence or a vacation getaway, this property is sure to impress.

5960 Peninsular Ave Unit 105, Stock Island

55 Coral Way, Stock Island
$1,250,000
3 Beds ⋅ 3 Baths ⋅ 615593 MLS
$151,000 PRICE REDUCTION! Here is your chance to purchase a TRUE TRANSIENT 3BR/3BA 1420 sq ft home. OCTOPUS'S GARDEN is one of only 8 stand alone units in the Coral Hammock gated community and has generated up to $157,000 in gross annual income. This income-producing home is being offered as a turnkey purchase, whimsically decorated with furnishings that reflect the laid-back, quirky island life style of Key West. You will be just down the street from the famous Hogfish Bar & Grill, Roostica Pizzeria, Hurricane Hole Marina & Restaurant and Chico's Cantina. The Key West Golf Club is just across the street. You will be just a short bike or Uber ride from Old Town Key West. THE COMMUNITY & GROUNDS... This freestanding home has two off street parking spaces directly in front, with a grassy lawn that surrounds the house. The front porch offers a shaded area to sit and relax. The back porch is perfect for a BBQ and the big back yard is great for the kids. An enormous communal swimming pool surrounded by plenty of chaise lounges directly across from your front door. Access to the clubhouse includes a shaded patio area overlooking the pool, as well as an indoor gathering area and a private fitness center with cardio equipment and free weights. FEATURES... **New impact doors and windows installed recently **New HVAC system installed in April 2025 with warranty **Interior and all exterior walls, and trim freshly painted **All decks freshly painted **Range, dish washer & microwave all replaced within the last three years **New furnishings & art work recently installed. **High quality flooring installed. **Home is scheduled for preventative termite tenting July 20. ** Washer and Dryer ** Ceiling Fans ** TVs in Living Room & All Bedrooms ** Fully Equipped Kitchen ** Linens and Towels included ** Community Pool Access ** Assigned Off-street Parking for 2 cars ** Fitness Center ** Clubhouse available for private parties

55 Coral Way, Stock Island

5178 Overseas Hwy, Stock Island
$1,042,500
6 Baths ⋅ 617871 MLS
Southernmost Golf Cart Rental - NEW INVENTORY PRUCHASED! TOTAL OF 31 HIGH END LUXURY CARTS! Turnkey Business Opportunity, Golf Cart Rental business offering strong immediate income and excellent growth potential servicing Stock Island & Key West, Florida. Southernmost Golf Cart Rental is a well-established, high-demand operation with 5 Star Reviews and known for its excellent Customer Service catering to the island's thriving tourism market. The business features a premium fleet of 31 loaded, 4 and 6 seater Club golf carts all equipped with Bluetooth sound systems, lights, Premium seats, Locked storage, and USB charging ports. Two of which are the brand new 'pontoon style golf carts'. Also, beach chairs, and YETI coolers, with convenient delivery and pickup services across Key West. Inventory also includes a 2 door Jeep Wrangler, Scooters, flat bed and enclosed Trailer, as well as office furniture, appliances, inventory for maintenance/repairs for Golf Carts, premium accessoriesMaintenance tools, chargers, branding, and digital assetsWebsite, booking system, and customer database. Financial InformationGross Revenue Available to qualified buyers as well as full inventory list with signed NDA/CA. Included in sale price, Sales & Operations Training and Online Presence: Active website and social media accounts. Building Lease and Business License and staff in place to resume business as usual with Unlimited Growth Opportunity!

5178 Overseas Hwy, Stock Island

5511 5th Ave, Stock Island
$1,000,000
2 Baths ⋅ 611994 MLS
Rare Warehouse Opportunity in Key West! Discover a unique investment opportunity with this spacious 5,484 sq ft warehouse located on Stock Island. Built in 1982, this two-story concrete structure offers versatile storage and office space, making it ideal for a variety of business needs. This space was once set up for 24 kennels but could now be used for storage units. Key features include: • Two loading dock doors—one with ramp access and one at truck loading dock height. • Four upstairs offices with a bathroom, plus an additional downstairs office, kitchen and bathroom. • Central air conditioning throughout the building. • Mixed-use zoning (MU) allows for flexible business operations. • Lot size: 7,458 sq ft, providing ample space for operations and storage. Located in the heart of Stock Island, this property is just minutes from downtown Key West, offering convenient access to major roads, businesses, and the waterfront. Don't miss out on this prime commercial space—perfect for investors or business owners looking to expand in the Key West area!

5511 5th Ave, Stock Island

7a 7th Ave, Stock Island
$780,000
2 Beds ⋅ 2 Baths ⋅ 618717 MLS
Refined Island Living with Privacy, Pool & Designer Finishes just minutes from Key West. Welcome to your private tropical retreat. This beautifully maintained 2 bedroom, 2 bath home blends thoughtful upgrades, designer details, & flexible living space - all surrounded by lush landscaping & mature fruit trees that create exceptional privacy. Inside, you'll immediately notice the luxurious Phillip Jeffries wallpaper throughout the home, adding depth, texture, & high-end sophistication rarely found at this price point. Solid hardwood interior doors (2023), updated lighting, ceiling fans, cabinet hardware, & modern fixtures complete the polished interior. The spacious primary suite is a true sanctuary featuring an ensuite bath with a fully tiled walk-in shower, Multi-jet shower system with rain head & arm head, Walk-in closet plus additional bonus closet, Attached side room perfect for an office, dressing room, yoga space, or easily reconfigurable third bedroom New window treatments with blackout shades. The guest bedroom includes a built-in queen Murphy bed that conveys with the sale, maximizing flexibility for guests while maintaining usable space. The kitchen offers wood countertops & updated appliances including a 2-year-old Whirlpool range, Samsung refrigerator, microwave, & stainless dishwasher. A dedicated laundry space with Kenmore front-load washer & dryer conveys. Additional updates include a new hot water heater (2022), Nest thermostat, impact-rated exterior door (2023), & accordion shutters for storm protection. Step outside to enjoy a fully fenced yard, above-ground swimming pool, beautiful landscaping & fruit trees for privacy & off-street parking. The roof was replaced in 2018. This home can easily be configured back to a 3 bedroom, offering flexibility for future needs. This is not just another island home, it's a thoughtfully upgraded, design-forward property offering privacy, function, and charm in one complete package.

7a 7th Ave, Stock Island

30f Cross St, Stock Island
$765,000
3 Beds ⋅ 2 Baths ⋅ 617516 MLS
Lowest priced home built to current code in the Key West zip code! Here's your chance to own a brand new 3 bedroom, 2 bathroom home with all the features you've been looking for—and then some. This home checks all the boxes: split floor plan, tile floors throughout, beautiful wood cabinets, quartz or granite countertops, and a full set of stainless steel appliances. It's the perfect blend of comfort, style, and durability. Enjoy Florida living with an 8' x 20' open porch made from low-maintenance composite decking—great for morning coffee or relaxing in the evenings. The yard is fully fenced, landscaped, and ready for pets or weekend BBQs. Underneath, there's a 300 sq.ft. storage enclosure, giving you plenty of space for bikes, tools, or beach gear. This home is built to the latest building codes, with impact windows and doors, concrete siding, a metal roof, and central A/C—all of which help keep insurance rates reasonable and your home safe and sound. Bonus: If you act quickly, you can still pick out your colors and finishes—make it truly your own before it's done! This is a solid new build with all the modern upgrades and none of the hassle. Come take a look and make it yours.

30f Cross St, Stock Island

317 Cross St, Stock Island
$640,000
3 Beds ⋅ 2 Baths ⋅ 616800 MLS
This 3 bedroom, 2 bathroom home is a great family home or investment opportunity; situated on a large 5625 sf corner lot within walking distance of the neighborhood park. It is currently configured with the main section having 2 bedrooms, living area, kitchen and a full bathroom plus an adjoining guest section that has it's own living area, kitchen, bedroom, full bathroom and it's own separate entrance. The large yard has 2 off-street parking spaces as well as Mango, Key Lime, Sour Orange and banana trees. Additional benefits include a metal roof and freshly painted exterior. All furniture except for the electronics are being included in the sale. The home has never flooded since being owned in 2006 or in storm Wilma in 2005.

317 Cross St, Stock Island

5030 5th Ave Unit 9, Stock Island
$580,000
3 Beds ⋅ 3 Baths ⋅ 619958 MLS
This move in ready townhome is located within the Islander Village HOA, a Local's Only Middle Income Workforce Community. Lush landscaping, pool, dog park and community park are all part of this lovely neighborhood On the first floor you will find 9' ceilings, a ½ bath, kitchen and living room. On the second floor there are 3 bedrooms and 2 full bathrooms. The home has front and back porches and is over a garage for 2 cars. Built in 2016, the home has a metal roof, impact windows and doors, and roof clips for low insurances of approximately $4,200 total annually. Additionally, the HOA dues are very low at $165 a month. FHA Financing with as little as 3.5% down. If you would like to join the Islander family, please call for more information on the home, community, mortgage options and County Workforce restrictions

5030 5th Ave Unit 9, Stock Island

E14 11th Ave, Stock Island
$559,000
3 Beds ⋅ 2 Baths ⋅ 617054 MLS
Charming 3 Bedroom 2 Bathroom Home Near Dining, Shopping, and Boating. Welcome to your new oasis! This delightful three-bedroom, two-bathroom home is perfectly nestled in a vibrant neighborhood, just moments away from an array of restaurants, shopping centers, and fishing spots. Enjoy an open-concept layout that seamlessly connects the living, dining, and kitchen areas, perfect for entertaining or relaxing with family. The well-appointed kitchen boasts, ample counter space, and a breakfast bar, making meal prep a breeze. The master suite features an en suite bathroom for added privacy. Step outside to a private backyard, ideal for weekend BBQs, gardening, or simply unwinding after a long day. A covered outdoor dining area is an added bonus. Situated just a short drive to Key West's popular dining options and shopping destinations, plus easy access to local fishing spots, this home is a dream for those who love to explore. Whether you're a family seeking a cozy retreat or a couple looking for a vibrant community, this home offers the perfect blend of comfort and convenience. Don't miss out on this incredible opportunity—schedule a showing today!

E14 11th Ave, Stock Island

5030 5th Ave Unit 80, Stock Island
$501,500
2 Beds ⋅ 3 Baths ⋅ 618379 MLS
This lovely townhome is located within the Islander Village HOA. This Local's Only Workforce Community has a pool, dog park and community park. The home is extensively renovated and the perfect home for a local with discerning tastes. The home has 9' ceilings on the first floor a custom kitchen, 1/2 bath, living room, and back porch. On the second floor is a large primary bedroom with 3 closets and private bathroom. Additionally you will find a second bedroom and full bathroom on the second floor. The home has a metal roof and impact windows and doors for low insurances (approximately $4,200 a year for all 3 policies). The HOA fee is low at $165 a month. Please call for more information on the home, community, mortgage and County Middle Income Workforce restrictions.

5030 5th Ave Unit 80, Stock Island

6800 Maloney Ave Unit 112, Stock Island
$485,000
2 Beds ⋅ 2 Baths ⋅ 618147 MLS
Open Water Views in Harbor Shores. A nice community near Key West. 2 bedroom/2 bath mobile home with private back patio deck and small front patio deck surrounded by tropical plants. Concrete dock. The place is cute and cozy! A great place to escape the cold. Your Keys getaway. Front has a concrete patio or driveway. Need notice to show, rented till July 31 2026. Renter willing to stay. No trespassing, by appointment only. Association has dock spaces they rent out limited to 21 ft. boat. You may park a small boat or kayak behind your place. The community docks is $85 per month, but is currently booked up. The boat can stay there as long as rules are followed and no hurricane is forecasted. No cost to use the boat ramp for residents. No board approval is required for a sale as long as all paperwork is completed and signed. The association fees are $230. per month which includes sewer, cable tv, and lawn service for common areas. 3 month minimum rental allowed. Declaration of condominium documents, available. No upcoming assessments.

6800 Maloney Ave Unit 112, Stock Island

5950 Peninsular Ave Unit 631, Stock Island
$470,000
619374 MLS
A beautiful 50' live aboard slip at Oceanside Marina (Oceans Edge Resort). Direct deep water access to the Atlantic Ocean make this a perfect Key West getaway for a passionate boater, vacation or permanent Key West home on a boat, or for a charter boat captain. Owners have full access to the resort facilities at Oceans Edge Resort, including six pools, a fitness center, full bath house with laundry facilities, dog park, free pump outs, fuel docks, and much more. A fantastic restaurant and bar are onsite, as well as outdoor movies and at times live music. Unlike most marinas in the Keys, this one has owned bay bottom, so it is an actual parcel of real estate, is financeable, and is not subject to a Florida Bay Bottom lease. Come see one of the best spots in Key West for boaters.

5950 Peninsular Ave Unit 631, Stock Island

6800 Maloney Ave Unit 35, Stock Island
$404,000
2 Beds ⋅ 2 Baths ⋅ 615518 MLS
Welcome to an exceptional opportunity in the quiet, well-kept community of Harbor Shores, just minutes from the heart of Key West. This well-maintained property offers both comfort and flexibility and is ideal for full-time living, a seasonal getaway, or future development. Step inside to an inviting open-concept great room with a split floor plan, offering two spacious bedrooms and a large bonus room that can easily serve as a third bedroom, home office, or gym. At the heart of the home, the oversized kitchen provides abundant space for cooking your fresh catch of the day or entertaining family and friends. Enjoy the Florida Keys lifestyle with thoughtful outdoor features, including a screened-in back porch, a patio perfect for grilling, and a workshop/storage room for all your supplies and gear. A private spiral staircase leads to a rooftop perch where you can soak in beautiful sunrise and sunset views. The oversized private driveway offers space for two vehicles, adding to your everyday convenience. Whether you move in as-is, renovate, or start fresh, the possibilities are wide open since this property is also ROGO-exempt. Located in a well-managed waterfront condominium park, the low $200 monthly HOA covers basic cable, lawn care, sewer, and common area maintenance. Boaters will appreciate the private community boat ramp, with dockage available on a first-come basis for an additional low monthly fee. Enjoy the convenience of being close to local marinas, Lower Keys Medical Center, Key West Golf Club, the International Airport, and all the vibrant shops, dining, and entertainment downtown Key West has to offer.

6800 Maloney Ave Unit 35, Stock Island

5950 Peninsular Ave Unit 643, Stock Island
$400,000
615731 MLS
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 setting known for its world-class boating, sportfishing, and island lifestyle. As part of the Ocean's Edge Resort, owners have access to resort-style amenities including six swimming pools, a state-of-the-art fitness center, full bathhouse with laundry, dog park, on-site gourmet restaurant and bar, fuel dock, pump-out service, parking, and convenient shuttle service to downtown Key West. The slip includes separate metered water and electric, dock box storage and newer docks. Unlike many slips in the Keys, this one features owned bay bottom, making it a true piece of real estate—fully financeable and not subject to a Florida Bay Bottom lease. Whether you're a full-time liveaboard, a weekend cruiser, or an investor looking for a rental income-producing slip, this property offers unmatched flexibility and value in one of the most desirable boating destinations in the country. Buyer to verify slip dimensions and review all condominium documents and marina rules.

5950 Peninsular Ave Unit 643, Stock Island

6810 Front St Unit Slip 12, Stock Island
$375,000
620724 MLS
Per the survey, Slip 12 is 100' x 25' and can accommodate up to 80' LOA x 23' boat. A rare find in the Florida Keys... Slip taxes ($200/yr) are included in the $1,239.82 low quarterly maintenance fee. SAFE HARBOUR MARINA is a deep water protected port and recreational marina with minimum14' depth. Located in the heart of the last vestiges of the commercial fishing and shrimping docks. It is a throwback to the old Key West, with a collection of locals, transplants, snowbirds, artists and craftsmen. 1 dockside assigned parking space, plus moped and bicycle parking. Private gated entrance. Metered electric, cable and wireless internet, city water and pump-out. Restaurant / Bar, secure bath, showers and laundry and dog park on site. 3 miles to Key West Airport, 5 miles to downtown Duval Street / Mallory Square. Key West is the most convenient port in Florida to the Caribbean, Mexico, Gulf States & South America

6810 Front St Unit Slip 12, Stock Island

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