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$5,495,000
5 Beds ⋅ 6 Baths ⋅ A12064822 MLS
“Discover Sunset Paradise – a stunning new construction Gulf-front retreat built in 2023 in the heart of Marathon, Florida Keys. This turnkey, fully furnished single-family home offers approximately 3,219 square feet of luxurious living space on a spacious 0.43-acre lot with direct open-water Gulf access.Boasting 5 bedrooms and 4.5 bathrooms (main house plus a separate guest cabana with A/C), this property sleeps up to 12 and is ideal for large families, multi-generational getaways, or premium vacation rentals. Built with durable concrete construction (CBS), it features bright, coastal-inspired interiors with panoramic Gulf views, a gourmet kitchen, and expansive living areas that flow seamlessly to outdoor entertainment spaces. It also includes a 4-car garage.Step outside to your private waterfront oasis: enjoy a beautiful heated pool with jacuzzi (perfect for year-round use, including winter), covered decks, and a massive 74-foot concrete dock ideal for boating, fishing, kayaking, or simply relaxing by the water. Additional highlights include a pergola, fish-cleaning station, bait freezer, and ample room for boat trailer storage.This home is a proven income producer with an active short-term rental license and established bookings through VRBO, Airbnb, and the highly regarded local management company Florida Keys Vacation Rentals. It is sold fully furnished and turnkey – ready for immediate enjoyment or continued rental success.

735 50 Street Unit Gulf, Marathon, Key West
$889,000
3 Beds ⋅ 2 Baths ⋅ A12064540 MLS ⋅ C BLDG.
This ground-floor unit was thoughtfully converted from three bedrooms into a spacious two-bedroom, two-bath residence -- each with its own ensuite -- plus an open dining room and wet bar built for Keys-style living: relaxed, social, and always ready for company. Kitchen and bathrooms are fully renovated. Marble floors throughout. Soundproof impact doors and windows. Dual-zone split A/C systems mean cool bedrooms and comfortable common areas -- no compromises in the tropics.Hurricane-rated glass doors frame a lush garden view and open directly to the resort-style pool -- engineered for outward visibility with true privacy from outside. An elevated private patio puts the pool, tennis courts, and tropical grounds steps away.HOA includes cable, security, building insurance, exterior maintenance, and exterminating -- predictable carrying costs, no surprise weekends managing a property.In 50 years since 1974, Key West by the Sea has never flooded through a single named storm. The City and State recently completed a raised stormwater system and elevated South Roosevelt -- infrastructure built for the next 50 years.Old Town, Duval Street, the Historic Seaport, Mallory Square -- all a short bike ride away. You're connected to everything Key West is, and then you come home to a quiet, gated community that feels a world apart.Full-time residence, mainland escape, or the life you've been working toward, #103C is ready. Key West isn't accidental. You choose it. Choose this.

2601 S Roosevelt Boulevard Unit 103C, Key West
$875,000
3 Beds ⋅ 3 Baths ⋅ B26059106 MLS
Excellent investment opportunity. This condo unit comes with a 25 X 60 deep water slip. The unit has been divide into three separate rental spaces. one bedroom, full bathroom with a kitchenette and two separate sleeping rooms with full bathrooms. Minutes from Key West.

6810 FRONT Street Unit B-15 & Slip 22, Key West
$2,499,000
2 Beds ⋅ 3 Baths ⋅ A12061218 MLS
Experience modern waterfront living at this exceptional 2-bed, 2.5-bath oceanfront home on Geiger Key, where contemporary design meets exceptional engineering. Envisioned by original owner and renowned author Reese Palley, the residence was designed to maximize breathtaking open-water views, natural light, and indoor-outdoor living. Remote-controlled blinds reveal an endless blue horizon, while expansive walls of impact glass and soaring cathedral ceilings create a dramatic sense of openness. The elegant, open-concept floor plan features clean architectural lines and spacious living areas. Engineered by structural and civil engineer Joel Roseblatt, the home was intentionally “over-engineered” for strength and durability. Reinforced concrete block construction and rare hollow-core concrete floor and roof systems provide remarkable structural integrity, fire resistance, thermal efficiency, and quiet security. Encompassing 3,672 sq. ft. under roof, the home offers expansive covered outdoor spaces for entertaining, waterfront dining, or peaceful mornings overlooking the water. Approximately 270' of concrete dockage and immediate ocean access provide an ideal setting for boating, world-class fishing, and sunset cruises. Located minutes from Key West yet surrounded by the tranquility of Geiger Key, 156 Sea Lane was built to endure for generations. See the “Supplement” tab for additional history on the property’s architecture and design.

Key West
$899,000
1 Beds ⋅ 1 Baths ⋅ A11989737 MLS
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 garage--perfect for comfortable living or rental income. The second unit has been demolished, providing a blank canvas to rebuild your dream home or expand your investment portfolio. Alternatively, you can choose to demolish the existing cottage and build two brand-new units on this generous lot. Mature landscaping surrounds the property, offering privacy and a serene atmosphere. With two separate ROGOs ready to go and the Staples side of the lot free from flooding, you can start building immediately. Don't miss this unique chance to own a versatile property in a prime Key West location with endless possibilities. Whether you're looking to renovate, rebuild, or develop, this property is your gateway to maximizing value and enjoying the vibrant lifestyle of Key West. Act now and make this exceptional property yours!

2330 Staples Avenue, Key West
$899,000
3 Beds ⋅ 2 Baths ⋅ A11989717 MLS
olid CBS construction home with a durable metal roof, ideally located within walking distance to marinas, restaurants, and local shops. This 3-bedroom, 2-bathroom property offers an elevated position with glimpses of the water from one side.Enjoy a spacious backyard perfect for entertaining, complete with an above-ground pool and plenty of room to relax or expand. The property also features off-street parking ideal for an RV or boat, plus ample street parking for guests.A great opportunity to own a well-built home in a prime Key West location with both convenience and lifestyle at your doorstep.

2311 Patterson Avenue, Key West
$1,850,000
B26047886 MLS
701 Simonton Street offers a standout commercial presence in the heart of Old Town Key West, positioned on the highly visible corner of Simonton and Angela Streets. This single-story commercial building features 1,745 square feet of functional interior space on a 6,510 square foot lot, with 8+ off-street parking spaces and a convenient drive-through parking layout. The existing floor plan includes five private offices, a reception/lobby area, storage, central air conditioning, and a security system, creating flexibility for many uses. Frame construction, a metal roof, and an X flood zone location add practical appeal for an owner-user or investor. Located in the Historic Neighborhood Commercial (HNC-1) zoning district, this corner property offers strong visibility, convenient access, and rare on-site parking in one of Key West's most established and walkable Old Town locations.

701 Simonton Street, Key West
$2,685,000
4 Beds ⋅ 5 Baths ⋅ B26044978 MLS
Brand-new construction in one of Key West's most desirable residential neighborhoods, the Casa Marina area of Old Town, just blocks from upper Duval Street and four blocks from the beach. This 4 bedroom, 4.5 bath single-family home blends modern durability with relaxed island living, offering the ease of low-maintenance ownership in the highly sought-after X flood zone. Built in 2026 to Florida's toughest standards, the home features concrete board siding, impact doors and windows, and an elevated first floor. The construction is designed to withstand winds up to 180 MPH. Inside, spacious living areas with high ceilings flow comfortably to a private outdoor retreat with an inground pool and water features. All bedrooms are en-suite, with one located on the first floor. A $15,000 builder appliance credit allows you to choose the finishes and appliance brands, at cost, that best suit your lifestyle. Off-street parking adds everyday convenience, while reclaimed wood accents from the historic schooner Western Union bring a meaningful connection to Key West history into the architecture. Quiet, private, and close to everything, this home offers luxury, walkability, and the best of Key West living.

1316 Royal Street Unit 6, Key West
$225,000
B26041179 MLS
Great opportunity to own a deep water slip minutes from Key West.

6810 Front Street, Key West
$37,500
2 Beds ⋅ 2 Baths ⋅ 1077507 MLS
Experience deeded ownership of the same week each year (Week 45) at the highly desirable Galleon Resort. This timeshare offers a fantastic location and some of the most spectacular sunsets in Key West. Filled with light, the unit features a private balcony overlooking the resort pool and waterfront. Enjoy views of passing sails and evening cruises, along with warm Gulf breezes and live acoustic music from the resort's tiki bar. Owners may place the unit in the on-site Galleon Concierge rental program. Comparable units during this week rent for apx. $3,885-$5,775 per week. Annual dues are $1,585 (2025), with taxes around $262 yearly. Enjoy the property yourself or generate rental income. Week 45 (Sep. 1st-8th) is an ideal time to visit, offering beautiful weather and a relaxed island atmosphere. Located in the heart of Old Town, just two blocks from Duval Street and next to the Historic Seaport Marina. The resort features a gym, BBQ area, private beach, pool and hot tub, 1 parking space

617 Front Street, Key West
$26,000
2 Beds ⋅ 2 Baths ⋅ 1076554 MLS
Welcome to your dream coastal retreat, where breathtaking Gulf and Marina views await you from this desirable PENTHOUSE, top-floor end-unit deeded Timeshare week 37! Nestled within a secure, gated community, this resort-style property offers exceptional amenities, one unassigned parking space, a sauna, fitness center, and the on-site Pirates Cove Café. Enjoy front-row views as Coast Guard vessels and iconic pirate ships pass by just beyond your balcony. In the evenings, open the doors to take in the warm Gulf breeze and the soothing sounds of the water. Week 37 offers an ideal getaway--featuring warm weather, fewer crowds, and a relaxed island atmosphere! Ideally located just two blocks from the iconic Duval Street and steps from the marina and Key West's Historic Seaport, you'll be surrounded by endless options for dining and entertainment. Stay or rent it out! Similar units have rented for approx. $4,165 to $6,195 for the week. Photos and view of a closely similar unit but not exact.

617 Front Street, Key West
$49,900
2 Beds ⋅ 2 Baths ⋅ 1076108 MLS
Welcome to your dream coastal retreat, where breathtaking Gulf and Marina views await from this desirable 3rd-floor lockout unit deeded timeshare week 46- where 2 units can be combined into one or separate. Nestled within a secure, gated community, this resort-style property offers exceptional amenities, one unassigned parking space, a sauna, fitness center, and the on-site Pirates Cove Café. Enjoy Key West's renowned annual Boat Float Week featuring an international event with thrilling races, lively race villages, and prime spectator viewing areas right to your island doorstep! Ideally located just two blocks from the iconic Duval Street and steps from the marina and Key West's Historic Seaport Village, you'll be surrounded by endless options for dining, shopping, and entertainment. Stay or rent it out! This unit's potential rental income ranges from $3,885 to $5,775 for the week. Photos and views are of a closely similar unit but not exact.,

617 Front Street, Key West
$32,500
2 Beds ⋅ 2 Baths ⋅ 1075831 MLS
Top floor Penthouse end unit! Experience premium waterfront ownership with this deeded timeshare week 36 in the highly coveted building at the Galleon Resort. This unit offers one of the most beautiful Key West Sunsets at the resort. The residence boasts windows for abundant natural light and a balcony that maximizes the breathtaking waterfront setting. Enjoy front-row views as Coast Guard vessels and iconic pirate ships pass by just beyond your balcony. In the evenings, open the doors to take in the warm Gulf breeze and the soothing sounds of the water. Walk downstairs or take the elevator to enjoy the Galleon's on-site Tiki bar with live music, the Pirates Cove restaurant, a private beach, a pool, and a hot tub! Week 36 (September 5th-12th) offers an ideal getaway--featuring warm weather, fewer crowds, and a relaxed island atmosphere. Stay or rent it out! This unit's potential rental income ranges from $3,885 to $5,775 for the week. Photos and views of a similar unit, but not exact

617 Front Street, Key West
$65,000
2 Beds ⋅ 2 Baths ⋅ 1074332 MLS
Experience premium waterfront ownership with this deeded timeshare week 36 in the highly coveted Building C at the Galleon Resort. This PENTHOUSE, end-corner unit offers one of the most desirable locations in the resort, featuring unobstructed, straight-on views of the Gulf of Mexico. The residence boasts soaring vaulted ceilings, additional windows for abundant natural light, and multiple balconies that maximize the breathtaking waterfront setting. Enjoy front-row views as Coast Guard vessels and iconic pirate ships pass by just beyond your balcony. In the evenings, open the doors to take in the warm Gulf breeze and the soothing sounds of the water. Stay or rent it out! This unit's potential rental income ranges from $4,165 to $6,195 for the week, Week 36 (2026: September 5th-12th) offers an ideal getaway, featuring warm weather, fewer crowds, and a relaxed island atmosphere! Photos and view of a closely similar unit, but not exact

617 Front Street, Key West
$640,000
2 Beds ⋅ 2 Baths ⋅ B26012772 MLS
Million dollar views! Ocean and Gulf views make this an affordable waterfront gem. Situated in the quiet and peaceful Bay Point neighborhood, this home is only 17 miles from Key West allowing quick city access and return to waterfront bliss. This Keys-style fish camp offers a waterfront manufactured home with 2 bedrooms and 2 baths. The side yard is a leafy oasis or reconfigured for parking. Enjoy easy living on 62' of ocean front with spectacular sunset views!

4 Shore Drive, Key West
$59,000
2 Beds ⋅ 2 Baths ⋅ 1073847 MLS
PENTHOUSE! Beautiful straight-on views of the Gulf, Pool, Beach, Sunsets, and Tiki Bar. Enjoy week 32 in this Timeless Timeshare and celebrate Lobster Week and the Rum Festival. The Galleon resort has Elevators, a rooftop deck, a gated parking garage, a sauna, an exercise room, and the Pirates Cove Cafe and Outdoor gas grills, which are located on the Marina side of the Galleon. Stay or rent it out! This unit's potential rental income ranges from $4,165 to $6,195 for the week. New 2026 furnishings! The penthouse has tall, vaulted ceilings and extra windows, allowing for natural light. This unit sleeps six with 2 beds, 2 baths, and a sleeper sofa. These photos are of a similar unit taken next door. Two sets of French doors with plantation shutters lead you out to your private balconies--5-piece primary suite with a jetted soaking tub and a walk-in shower. Enjoy the active waterways and boats as they sail by--photos and views of a closely similar unit, but not an exact .

617 Front Street, Key West
$42,000
2 Beds ⋅ 2 Baths ⋅ 1073845 MLS
Views of the famous Key West Sunset, Gulf of Mexico and pool await you when you arrive at this 4th-floor end- deeded timeshare unit. The live music from the Tiki bar saunters up to the balconies. This highly desirable winter week is magical enjoy the warm weather and Christmas boat parades while Key West is all dressed up for the holidays. Enjoy the private beach, pool, hot tub, sauna, outdoor gas grills located on the marina. Tiki Bar, Privates Cove cafe, exercise room or just steps away walk out the the Historic Key West Seaport Village for a delicious dinner or happy hour and just 2 blocks away is Famous Duval Street. The fully furnished unit has been updated with new furnishings. With 2 beds and 2 baths,, plus a sofa couch, this unit sleeps 6. Stay or rent it out! This unit's potential rental income ranges from $5,705 to $7,595 for the week. Highly rated resort - enjoy panoramic Key West views from the rooftop! Photos and Views are closely similarthe to unit but not exact.

617 Front Street, Key West
$59,900
2 Beds ⋅ 2 Baths ⋅ 1073844 MLS
On the Gulf of Mexico this 4th floor end unit Timeshare is on the water and overlooks the Key West Marina. 2 bed 2bath with sofa couch sleeps 6. Week 50 is a very sought after week that offers ideal winter weather, a relaxed island atmosphere and peak rental demand. Enjoy the decorative Christmas boat parades from your own personal view balconies and experience Key West all dressed up for the holidays. Enjoy the private beach, heated pool and hot tub, Tiki Bar, fitness center on onsite Pirates Cove cafe. In addition there are gas grills out on the marina. The C building in one of the most desirable buildings. Elevators, gated parking garage and lot. Brand new furnishings. The roof has a top deck to enjoy the most glorious Key West sunsets. Just steps away from the Historic Key West Seaport and 2 blocks from famous Duval Street. Photos and views are of a similar unit; the exact unit's layout is similar. Stay or rent it out! This week has rental potential of approx. $ 5,565-$ 7,595.

617 Front Street, Key West
$149,900
B26007496 MLS
The ultimate waterfront living in the middle of Key West with this 34' 1987 Corker Holiday Mansion Houseboat on a state of the art floating dock at the City's Garrison Bight Marina. Fully furnished and new air conditioning. Low slip fee of $ 680 per month includes 2 parking passes, 2 clean laundry and shower facilities, free pump out and patrolled security. Very favorable Lease terms and conditions were just approved by the City. Sold together with the leasehold slip for a seamless transition into your new marina lifestyle

1801 N Roosevelt Boulevard, Key West
$62,000
2 Beds ⋅ 2 Baths ⋅ 1073028 MLS
Penthouse! What an incredible opportunity to own this fabulous penthouse at the Galleon Resort. Enjoy the unmatched appeal of owning a deeded Key West timeshare during the final week of the year, Week 52- one of the most desirable weeks in the Florida Keys! This prime holiday week offers Key West's legendary New Year's Celebrations, including live music, fireworks, and iconic Duval Street events. The Penthouse boasts expansive, straight-on views of the Gulf. Pool, hot tub,, private beach and Tiki bar, where a local guitarist performs nearly every day or night. There are elevators and one unassigned parking space. There is a sauna and exercise room, and the Pirates Cove cafe. Gated community. This Penthouse is located just two blocks from Famous Duval Street, and steps away from the marina and Key West's Historic Seaport. Daily Stay your week or rent it out. Rental rates for this unit range from $5,705 to $ 7,875 for the week.Photos and the view are of a similar unit, but not an exact

617 Front Street, Key West
$999,999
3 Baths ⋅ R11168914 MLS
Income producing Duplex in Old Town Key West! The Owner would prefer to hold the financed note for a new owner. Fully renovated offering strong income potential and turnkey condition. Recent upgrades include a new roof, siding, impact windows, updated kitchens and baths, and new flooring in the rear unit. The downstairs features two lockout units--rear unit with large private backyard, and front unit with private front porch. Upstairs treetop unit is currently tenant-occupied. Centrally located directly across from Bayview Park, this property offers consistent rental demand and separate electric. X Flood zone with plenty of room for a pool in the backyard.

1018 Georgia Street, Key West
$799,000
3 Beds ⋅ 1 Baths ⋅ R11167247 MLS
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. Being sold As-Is.

1425 Eliza Street, Key West
$235,000
R11163184 MLS
LIVE IN PARADISE AFFORDABLE LIVEABOARD Houseboat & Slip! It's a TRUE KEY WEST LIFESTYLE... POF CASH ONLY! If your ready to enjoy life and have a crash pad in the Florida Keys, then come and see this one. 2018 Aqua Lodge Catamaran Houseboat 12'X42 2' Draft Molded Pontoon, FRP Hull No Motors, No batteries 50-amp shore service connection with pump out included with slip Fee $830 a month, parking, bicycle, scooters, Laundry/Bathroom/Showers and 24 hour Patrolman

1801 N Roosevelt M-28 Boulevard, Key West
$269,900
R11163110 MLS
Very well maintained 2017 Trident 45' Houseboat being conveyed with a leasehold slip at City's Garrison Bight Marina , in the middle of Key West ! One of the few seaworthy vessels in the Marina . Low slip fee of $ 908 per month includes free pump out , 2 parking passes , 2 very clean laundry and shower facilities , patrolled security

1801 N Roosevelt Boulevard N, Key West
$4,375,000
5 Beds ⋅ 6 Baths ⋅ R11113482 MLS ⋅ The Seven Palms - A Key West Oasis BLDG.
Welcome home to an exceptional new-construction residence in a private, gated community offering resort-style amenities, a boat slip and nightly rental opportunities. Conveniently located next to Summerland Key Airport, this fully upgraded home features a private elevator, a stunning infinity pool overlooking the water and an expansive rooftop deck perfect for enjoying breathtaking Florida Keys sunsets. Only have two homes remaining.

231 E Shore Drive Unit Unit 6, Key West
$1,799,000
3 Beds ⋅ 3 Baths ⋅ R11007158 MLS
Excellent opportunity whether looking for a private residence or an investment. This condo 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 residence. Assigned off street parking right in front of the unit. This property is being offered turnkey. Vacation Rental history available .This home has all hurricane impact windows and doors. making the unit noiseless.

1011 Simonton Street Unit 1, Key West
$6,499,000
R10804772 MLS
A rare opportunity to own a private island minutes from Key West. There are so many possibilities. A private equestrian estate, ''The Southernmost Stables ''. This property would be an excellent place to host large events or possibly therapeutic programs or retreats.Beautiful beach areas. Easy to get to, as the island has access to the mainland via a 1/2 mile land bridge. The property is also located next to one of the largest mega yacht marinas and close to upscale hotels. The owners currently run a small farm, bee keeping and kids summer camps on the island. One of the few places with untouched nature left in the Florida Keys.

7200 5th Street, Key West
$9,499,000
R10963178 MLS
Nestled along the serene waterfront, these two picturesque parcels offer an unparalleled opportunity to indulge in the quintessential Florida Keys lifestyle. Boasting breathtaking panoramic views of the glistening waters, these two expansive plots of land / bay bottom present the perfect canvas for your dream waterfront retreat and /or commercial ventures. The Northern parcel consists of about 1,400 ft. of pristine shoreline, providing ample space for waterfront activities such as swimming, fishing, kayaking, and paddleboarding with deep water on one side and shallow bay bottom on the other side. Spanning 2.03 acres of Mixed Use upland and a total of 45 acres, including bay bottom. Potential uses on the Northern parcel could be Commercial retail, restaurant uses, or any combination there thereof, imagine a floating restaurant, small marina, Commercial recreation uses including amusement or sea life park, opening doors to community-centric projects that serve the needs of locals and visitors alike. The off shore island along the channel offers great camp sites. With Mixed Use zoning in place, commercial fishing docks are permitted, providing an excellent opportunity for entrepreneurs in the fishing industry to establish a thriving business. The Southern parcel consists of 50 acres of mangrove forest, beach berms, hammocks, and trails with approx. 6 acres of upland. So many possibilities. Build your own Equestrian Estate, ''The Southernmost stables''. This property would be an excellent place to host large events like concerts, weddings, farm to table / wine tastings, or possibly therapeutic programs or retreats. Beautiful beach areas. Easy to get to, as the island has access to the mainland via a ½ mile land bridge. The property is also located next to one of the largest mega yacht marinas and close to two upscale hotels. The Southern parcel of Cow Key can be purchased by itself. See MLS RX-10804772.

7000 5th Street, Key West
$2,595,000
3 Beds ⋅ 3 Baths ⋅ R11067758 MLS
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.

508 Grinnell Street, Key West
$1,100,000
3 Beds ⋅ 2 Baths ⋅ F10500340 MLS
Price Reduced!!! Lovely 3 bedroom 2 bath home in the midst of Old Town just off Duval St. Central AC with nice room sizes and great lot size. Flood Zone Z500. Ready to sell As-Is. Seller motivated but firm on price. Please ask Listing Agent about historical significance of this property.

414 Virginia Street, Key West