Monroe Homes with Waterfront

Monroe Homes with Waterfront

Monroe County, located in the state of Florida, is a captivating region known for its stunning natural beauty and vibrant waterfront lifestyle. Situated in the southernmost part of Florida, Monroe County is home to the famous Florida Keys, a chain of islands renowned for their crystal-clear turquoise waters, white sandy beaches, and abundant marine life.

One of the most sought-after features in Monroe County real estate is waterfront properties. With a high percentage of homes offering waterfront views, residents have the luxury of enjoying breathtaking sunsets, boating, fishing, and various water activities right from their own backyard. Whether it's a charming beachfront cottage, a luxurious oceanfront estate, or a cozy canal-front home, Monroe County offers a diverse range of options for those seeking a waterfront lifestyle.

Living in Monroe County also means having access to an array of outdoor recreational opportunities. From exploring the stunning coral reefs while scuba diving or snorkeling to kayaking through the mangrove forests, there is no shortage of adventures to embark on. The county is also home to several state parks and nature reserves, providing ample opportunities for hiking, birdwatching, and wildlife spotting.

In addition to its natural wonders, Monroe County boasts a vibrant arts and cultural scene, with numerous galleries, museums, and theaters. The region also offers a variety of dining options, ranging from fresh seafood shacks to upscale waterfront restaurants, where residents can indulge in delicious cuisine while enjoying breathtaking views.

Whether you are looking for a peaceful retreat or an active waterfront lifestyle, Monroe County, Florida, offers the perfect blend of natural beauty, recreational opportunities, and cultural experiences.

Newest Monroe Homes with Waterfront

4 Beds ⋅ 3 Baths ⋅ NS1088280 MLS

Set within Coco Plum area of Marathon, this waterfront residence presents a rare opportunity to own a premier canal-front property in the Florida Keys. Offering direct boating access to open water, this home embodies the ultimate island lifestyle for the avid boater and coastal enthusiast. The property features a desirable waterfront setting, elevated construction, and an exceptional layout that provides the perfect bones to transform it into your dream home. With endless potential for customization, this residence is ideal for creating a modern coastal retreat or luxury Keys estate tailored to your vision. Located on a quiet, highly sought-after street, it offers both privacy and convenience, just minutes from beaches, dining, and all that Marathon has.

2100 Avenue H, Marathon

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

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

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

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

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

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

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

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

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

5 Beds ⋅ 5 Baths ⋅ W7882829 MLS

LOCATION LOCATION LOCATION DIRECTLY ON THE GULF W/ GULF OF AMERICA AND MARINA VIEWS! Welcome to an extraordinary opportunity to own a newly constructed, luxury waterfront residence in the heart of the Florida Keys. Located in the exclusive Emerald Landings community in Marathon, this exceptional home offers breathtaking open-water views, a private 50' boat slip included, and a rare private beach, kayak launch, blending high-end coastal living with unmatched boating convenience. Thoughtfully designed for both luxury and functionality, this stunning property features 5 bedrooms and 5 bathrooms, including two spacious primary suites with private balconies overlooking the water. An open-concept floor plan showcases a chef's kitchen with quartz countertops and waterfall island, seamlessly flowing into the living and dining areas--ideal for entertaining or relaxing with panoramic sunset views. Outdoor living is elevated with a heated resort-style pool, expansive patios, and multiple spaces designed for al fresco dining and sunset gatherings. Premium finishes, coastal-inspired design, and modern technology are found throughout the home, offering a turn-key experience for owners and guests alike.This property is the perfect investment opportunity, boasting a proven short-term rental history and strong income potential, while also serving as an ideal future personal residence for those dreaming of a private retreat in the Keys. Whether used as a high-performing vacation rental, a seasonal escape, or a full-time waterfront home, this property offers unmatched versatility. Centrally located near world-class boating, dining, shopping, and beaches, this rare offering combines luxury, location, and lifestyle--a true Keys dream home with income-producing potential. Being offered furnished.

805 39th Street Gulf, Marathon

Rare opportunity to own a stunning ocean view double lot with 107 feet of canal frontage in sought-after Big Pine Key! Currently #5 in ROGO, this prime property comes with approved building plans—available upon request. The spacious lot offers ample room for your dream home with direct canal access and breathtaking open-water views. Buyers may have the ability to modify the existing plans—please confirm options with the Monroe County Planning Department. Lot 1 & 2 being sold together, will not sell separately. Don’t miss your chance to build in one of the Keys’ most desirable locations!

2080 Coral Way, Big Pine Key

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