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$949,000
3 Beds 2 Baths 619680 MLS
Where boating lifestyle and modern coastal design align, this fully renovated 3-bedroom, 2-bathroom home in Cudjoe Key delivers exceptional waterfront living. This completely reimagined residence is ideally positioned on a premier corner canal lot, offering approximately 190 feet of concrete seawall and dockage along two waterways, an exceptional setting for boating and waterfront enjoyment. Thoughtfully renovated throughout, the home showcases a clean coastal-modern design with new impact windows and doors, an elevated interior finish, and a beautifully updated kitchen featuring sleek cabinetry, premium surfaces, and an open layout ideal for entertaining. Light-filled living spaces flow seamlessly onto the newly replaced covered rear porch, where tranquil canal views create the perfect backdrop for relaxed indoor/outdoor living. The exterior stairs have also been recently replaced, complementing the home's refreshed and well-maintained feel. Boating enthusiasts will appreciate the 10,000 lb boat lift, expansive seawall/dockage, and quick access to open water via Cudjoe Bay. Downstairs, a large enclosure provides abundant storage space for tools, fishing gear, and boating equipment, an invaluable feature for Keys living. Located on a quiet street in an established neighborhood, this property offers a rare combination of modern updates and generous waterfront in the Lower Florida Keys.

22953 John Silver Ln, Cudjoe

$6,999,000
8 Beds 6 Baths 619673 MLS
Spectacular Bayfront Estate with Guesthouse in the Heart of Islamorada. & 7 Day Rental Potential, Seller Financing Available. Experience luxury coastal living at its finest in this exceptional Gated bayfront estate, ideally situated in the heart of Islamorada. Set on a rare peninsula with over 225 feet of prime waterfront, this property offers unmatched privacy, panoramic views, and direct access to both the Florida Bay and Atlantic Ocean. The main residence features 7 spacious bedrooms and 5 beautifully appointed bathrooms designed with both elegance and comfort in mind--perfect for entertaining or hosting large gatherings. A dramatic third-floor Birds Nest Sky Lounge features 360-degree glass walls and a walkout rooftop deck, capturing breathtaking vistas in every direction. Expansive living areas and thoughtfully designed spaces capture stunning water views from every angle. A Whole House Generator for peace of mind. A private 1-bedroom, 1-bathroom guesthouse provides the ideal retreat for visitors, accommodating extended family, or potential rental income or creating a secluded retreat. For boating enthusiasts, the estate includes an impressive 85+ foot deep-water yacht slip and four boat lifts, offering seamless access to both the Bay and Ocean--an unparalleled fishing advantage in the Florida Keys. Step outside to your own waterfront oasis, where a gorgeous heated bayfront pool invites relaxation while you take in breathtaking sunset views and the tranquil surroundings. Blending luxury, comfort, and premier waterfront access, this remarkable estate presents a rare mixed-use opportunity in one of Islamorada's most coveted locations. Seller will consider all reasonable offers.

1101 Mastic St, Islamorada

$699,000
1 Beds 1 Baths 619668 MLS
Welcome to the iconic Cheeca Lodge & Spa Resort--a rare opportunity to own a premier, income-producing property in the heart of Islamorada. This beautifully appointed one king-bedded room with kitchen, private screened in balcony, with owners closet, offers the ideal blend of personal retreat and investment potential. Set within one of the Florida Keys' most celebrated resorts, owners and guests enjoy a true luxury experience, featuring exceptional dining, new ballroom, two tiki bars, a full-service spa, fitness center, and multiple resort-style pools, 9 hole, Par 3 golf course, The property boasts direct beach and dock access, along with lighted tennis courts, pickleball courts and a wide array of water sports, all surrounded by lush tropical landscaping. Nightly rentals are permitted, creating strong income potential, while professional onsite management provides seamless maintenance and guest services. Ideally located just moments from Islamorada's renowned restaurants, galleries, breweries, shopping, and vibrant art district, this is a unique chance to own within one of the Keys' most historic and sought-after destinations.

81801 Overseas Hwy Unit # 729, Islamorada

$795,000
1 Beds 1 Baths 619656 MLS
Large, Bayfront parcel with over 43' of easily accessible dockage with 12,000 lb. boat lift, and a 2019 Heartland Landmark 365 Phoenix 5th Wheel . Rare offering; one of only twenty Bayfront lots available in Calusa Campground. Take in beautiful open-water views with easy access to the shimmering Florida Bay, which is perfect for boating, fishing, and long, sun-soaked days on the water. Whether you're craving adventure or a peaceful escape, this home offers the best of both worlds in seamless balance. Calusa is a lively, amenity-filled community built for relaxation and recreation alike. Residents enjoy a playground, tennis and basketball courts, a sparkling pool, plus a convenient boat ramp and dock--everything you need to embrace the Keys lifestyle. With round-the-clock security and handy on-site services like propane and ice, everyday living is effortless. Opportunities like this don't come along often.

325 Calusa St Unit 222, Key Largo

$1,149,000
619655 MLS
Waterfront commercial investment opportunity with 100 feet of dockage on a 13,500 sq ft lot, offering both canal frontage and open ocean views--an increasingly scarce combination in the Upper Keys. Ideally located just outside Port Antigua and White Marlin Beach, the property benefits from strong visibility and proximity to established boating and residential communities. The site features convenient eastbound ingress and egress, supporting efficient operations and customer access. Zoned Commercial Fishing, it allows for a diverse range of income-producing uses, including charter services, boat rentals, marine repair, seafood distribution, restaurant or other waterfront commercial ventures. With direct water access, substantial dockage, and flexible zoning, this parcel is well-positioned for long-term appreciation and immediate revenue potential in a supply-constrained coastal market.

74520 Overseas Hwy, Islamorada

$32,500
2 Beds 2 Baths 619654 MLS
Top floor unit! Experience premium waterfront ownership with this deeded timeshare 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. Located just steps from the rooftop terrace, this unit also provides easy access to some of the best sunset views in Key West. Week 36 (September 5th-12th) offers an ideal getaway--featuring warm weather, fewer crowds, and a relaxed island atmosphere. This is a rare opportunity to own a premier week in one of the resort's most sought-after units. This condo is nestled in the heart of Old Town, just two blocks from Duval. And right next to the Historic Seaport Key West Marina. 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 heated in-ground pool and hot tub, an exercise room, and a built-in BBQ grill. The Galleon resort also offers fantastic raffles for owners and daily poolside bingo. Place your unit with the on-site Galleon Concierge Management and place it in the rental pool. Rental prices for a 2-bed, 2-bath unit this week are approximately $3,885 to $ 6,195 per week. Dues are $1,585 (2025) paid annually, and taxes are approximately $262 per year. So, for less than $2K a year, stay at this incredible resort and enjoy for yourself, or rent it out. Jet skis and bikes are available on-site for rent. The week includes 1 unassigned parking space. This is a great opportunity to own a deeded week at an exceptional, highly rated resort!

617 Front Unit B-51 Penthouse Week 36, Not Provided

$398,000
2 Beds 1 Baths 619652 MLS
An exceptional opportunity to own this charming 2-bedroom, second-floor condominium, in Cocoplum Terraces, ideally situated on a 200-foot-wide canal with direct ocean access and no bridges. Weekly rentals are possible. Located just one-half mile from beautiful Cocoplum Beach and park, this waterfront community offers the true Florida Keys boating lifestyle. Amenities include assignable boat slips, on-site boat and trailer storage, Kayak Storage, a high-quality boat ramp with loading dock, and a heated swimming pool at the water's edge. Enjoy peaceful views from your private balcony overlooking the pool and waterway, an updated kitchen with sit up bar, updated flooring and views from your private patio/porch area.

105 Ave D Unit 110, Marathon

$1,175,000
3 Beds 2 Baths 619645 MLS
Welcome to your piece of paradise in Breezeswept Beach Estates, where laid-back island living meets premier canal-frontage. From here, it's an easy cruise to open water--perfect for early morning fishing runs, sunset sails, or spontaneous sandbar days. Inside, this bright and breezy retreat has been thoughtfully updated with stainless steel appliances, sleek Silestone countertops, and warm hickory cabinetry--bringing that effortless coastal style to life. Step outside and the vibe continues: low-maintenance artificial turf and durable Trex decking, ready for paddleboards, kayaks, or just dangling your feet in the water. With 60 feet of concrete seawall, there's plenty of room to dock your boat and head out whenever the mood strikes. A two-car garage and generous downstairs storage mean all your gear--from fishing rods to beach cruisers-has its place. The fully fenced yard offers the perfect setting for private entertaining, backyard barbecues, and easy island nights under the stars. Breezeswept Beach Estates features a voluntary association that fosters a friendly, connected community and maintains a neighborhood website for just $25/year. The only thing missing...is you.

27395 Saint Lucie Ln, Ramrod

$2,380,000
3 Beds 2 Baths 619644 MLS
Experience the ultimate Key West waterfront lifestyle with this private tropical retreat on the highly coveted Riviera Canal--one of the island's only canals offering direct boating access to world-class fishing and diving. Tucked behind a gated entrance, this beautifully landscaped property welcomes you into a lush, secluded garden setting that feels like your own hidden oasis in the heart of Key West. This meticulously maintained 3-bedroom, 2-bath ground-level pool home blends comfort, style, and functionality. Inside, you'll find elegant travertine flooring throughout, granite countertops, stainless steel appliances, and a wet bar--perfect for entertaining. The thoughtfully designed layout features two separate living areas, with both the main living space and the primary suite opening through hurricane-impact sliding glass doors to the backyard. Step outside to your private resort-style escape, where a stunning in-ground concrete pool overlooks the tranquil canal. Enjoy peaceful water views, frequent visits from manatees, and the natural privacy provided by protected mangroves across the water. The screened, covered lanai creates the perfect setting for outdoor dining and relaxation year-round. Boaters will appreciate the 15,000 lb boat lift, allowing you to go from home to open water in minutes. Additional premium features include a newer generator with large propane tanks, outdoor shower, electric gate, automated irrigation and landscape lighting, covered carport, and secure off-street parking for two vehicles. Located just minutes from Key West International Airport, dining, and local attractions, this exceptional property offers the perfect blend of convenience, privacy, and island luxury. Whether you're seeking a full-time residence or a vacation escape, this waterfront home is a rare opportunity to own a true piece of paradise.

3108 Riviera Dr, Key West

$639,000
2 Beds 2 Baths 619635 MLS
Spectacular peekaboo open water views abound with this updated 2 bed/2 bath canal front home with 35 foot seawall. Located in a gated community with tons of amenities. New kitchen w/Caesar quartz countertops, full backsplash, new stainless steel appliances, Koehler sink, modern, white cabinets with an abundance of storage, including a large center Island. Open concept floor plan with open water views from the dining area and deck, dedicated dining nook and large porch off the dining room complete with balmy breezes and canal views. Large en-suite master bed/bath with ample size guest bed/bath. House comes furnished with a Keys vibe, just bring your swimsuit, your boat and get ready to enjoy the beautiful water and activities in the Florida Keys!

701 Spanish Main Dr Unit 495, Cudjoe

$745,000
3 Beds 3 Baths 619632 MLS
Spacious 3BR/3BA custom home in desirable Bahia Mar (MM 102.4)! Meticulously maintained, exceptionally clean, and move-in ready, this solidly built home offers privacy, comfort, and endless potential. (Square footage does not include the downstairs guest suite with bedroom, bath, and kitchenette.)Situated on one of the community's most desirable low-traffic streets with no front neighbors, you'll enjoy tropical landscaping, park-like views, refreshing ocean breezes, and abundant natural light throughout. Soaring Dade County pine ceilings, impact windows and doors, a 2021 metal roof, spacious great room, generous attic storage, and covered patios create the perfect Keys retreat. The open kitchen features granite countertops, custom cabinetry with pull-outs, lazy Susan storage, pantry, wine cooler, and quality appliances. Flexible living areas offer space for a home office, gym, hobby room, or additional sleeping area. The private lower-level guest suite is ideal for visitors, extended family, entertaining, or potential rental income. Bring your boat, RV, and all your toys! Ample parking, covered parking, and plenty of room to add a pool make this property even more appealing. While Bahia Mar does not have a private homeowners' boat ramp, you're just minutes from some of the Florida Keys' finest public boating and waterfront destinations. Launch at nearby John Pennekamp Coral Reef State Park, offering a public boat ramp, world-famous coral reefs, snorkeling, diving, kayaking, glass-bottom boat tours, beaches, and nature trails. You're also close to Key Largo Park, Caribbean Club boat ramp, public docks, full-service marinas, waterfront dining, fishing, pickleball courts, shopping, and the mainland for easy commuting. Whether you're searching for a full-time residence, weekend getaway, or investment opportunity, this immaculate home offers outstanding value, an unbeatable Upper Keys lifestyle, and room to make it your own.

1033 Valencia Rd, Key Largo

$920,000
619630 MLS
Experience the ultimate Florida Keys waterfront lifestyle with this rare oversized boat slip located in the highly sought-after Coco Plum Beach neighborhood of Marathon. Situated in the exclusive Coco Plum Beach Yacht Club. Boasting an impressive 22-foot x 80-foot slip with a 65 foot dock, this slip is perfectly suited for accommodating larger vessels with ease. Positioned on the oceanside, you'll enjoy direct, bridge-free access to open water - an exceptional advantage for avid boaters and anglers alike. Tucked at the very end of a secure, gated section of the marina, this prime location offers enhanced privacy along with quick effortless navigation straight to the ocean. Enhancing the experience is a generous 11' x 30' tiki hut creating an inviting outdoor living space just steps from your vessel. The slip is fully equipped with Electric, water and pump out services for maximum convince. A dedicated storage unit provides ample space for all your boating gear and equipment. The marina offers convenient amenities including a community pavilion, bathhouse, and on-site laundry facilities. With a premium location and a strong rental income potential, opportunities like this - featuring large slips paired with land based living amenities - are increasingly rare. Don't miss your chance to own a unique piece of paradise. Survey on file; Dimensions 38' x 82' x 68'

100 Ve I, Unit A, Marathon

$199,000
619623 MLS
This is a property for someone thinking about the future, not just today. The lot measures 110' x 110' (just over a quarter acre), is cleared, and sits on a 100-foot-wide, boatable canal with quick access to open water. It's directly across from Cocoplum Beach, giving it a quiet, natural setting that's hard to find. You'll notice there are already homes on this street, including next door, and the two streets leading in show a similar pattern -- one side built out, the other still open. These larger parcels create space, privacy, and a peaceful feel tucked away from US-1. As it stands today, the lot does not meet current density requirements to be built on as a standalone parcel. A site condition letter from the City will be obtained and provided so buyers have a clear understanding of its current status. There are also three adjoining privately owned lots. While there are no guarantees, a future owner could explore the possibility of assembling multiple parcels or changes over time that may affect what's allowed. This is best suited for someone who understands the current limitations, doesn't need to build right away, and sees value in holding a unique piece of property for the long term.

Ave M, Marathon

$2,890,000
5 Beds 4 Baths 619621 MLS
Huge Direct Oceanfront Compound -- One-of-a-Kind with 276-Foot Concrete Dock Adjacent to World-Famous John Pennekamp, Coral Reef State Park & Molasses Reef. Discover a truly exceptional and private oceanfront compound designed for boating enthusiasts, investors, or multi-generational living. Spread across three expansive lots, this rare property includes two distinct homes and direct water access -- a combination that's nearly impossible to find in today's market. The primary residence features a Modern Style 3 bedrooms and 2 full baths, offering bright, comfortable living spaces and sweeping ocean views. The second home, complete Modern Style 2 bedrooms and 2 baths on a separate meter, is ideal for guests, or extended family. Step outside to unparalleled oceanfront living with a 276-foot concrete dock, perfect for accommodating large vessels, fishing, and launching watercraft. The grounds offer generous room for entertaining, expansion, or simply enjoying the peaceful surroundings of this secluded coastal haven. Highlights: 3 lots with two homes and a 276-ft dock, Turn-Key Direct ocean access -- idea for boating on the Ocean or Bay. Steps from John Pennekamp Coral Reef State Park Perfect for entertaining, investing, or creating a family retreat Unmatched privacy and coastal lifestyle potential. Seller will consider all reasonable offers.

34 Atlantic Dr, Key Largo

$850,000
2 Baths 619620 MLS
FOR SALE: Mellow Ventures LLC - Premier Eco-Tour & Luxury Houseboat Rental Company in the Florida Keys Step into one of the most unique lifestyle and income-producing businesses in the Florida Keys. Mellow Ventures LLC is a turnkey, multi-stream eco-tour and hospitality operation with a proven track record, established brand presence, and rare waterfront assets perfectly positioned for continued growth. Operating out of Key West, this boutique adventure company has built a reputation for intimate, sustainable experiences on the water—guided eco tours, private charters, island excursions, and custom adventures designed to showcase the natural beauty of the Lower Keys. In addition to its successful charter business, the sale includes two custom-built luxury houseboats, currently operating as high-demand short-term rentals. These floating suites offer a one-of-a-kind Airbnb experience that consistently generates strong occupancy and premium nightly rates. Each vessel blends modern comfort with an immersive waterfront setting, providing an unforgettable stay for guests seeking something truly special. Highlights Include: -Well-established eco-tour & charter business with brand recognition in Key West -24' Twin Vee -Two fully custom houseboats designed for nightly rentals -Strong Airbnb track record with exceptional occupancy -Multiple revenue streams: eco tours, private charters, overnight rentals -Turnkey operation with booking systems, media assets, furnishings & equipment -Excellent online reviews and repeat clientele -Ideal opportunity for owner-operator or investor seeking passive/managed income -Rare waterfront lifestyle business in a world-renowned destination This is a unique chance to acquire a thriving, experiential Keys business blending adventure tourism with boutique hospitality—a lifestyle investment that generates real returns.

Rat, Key West

$999,000
6 Beds 2 Baths 619618 MLS
Duplex with Solid Income - $91,800/Year This income-producing duplex offers two spacious units, each featuring 3 bedrooms and 1 bathroom--an ideal setup for steady, long-term rental demand. Currently leased at $3,850 and $3,800 per month, the property delivers a strong annual income of $91,800. Situated on a 4,400 sq. ft. lot in a desirable location near the coast, this property is just a short ride from the energy of downtown, making it highly attractive to tenants who want both convenience and lifestyle. Each unit is separately configured, providing flexibility for investors or owner-occupants. The rear unit benefits from off-street parking--a valuable feature in this market. Built with durable Indian Block construction, the property offers long-term structural integrity with room for future value-add opportunities.

1916 Seidenberg Ave, Key West

$1,500,000
9 Beds 7 Baths 619617 MLS
Right in the heart of Key West, this income-producing triplex is the kind of property investors are always asking for--strong numbers, solid layout, and a location that never goes out of style. The property features three spacious units, each offering 3 bedrooms and 2 bathrooms, making them highly desirable for long-term tenants. The front unit stands out with its single-level design--larger than the others and perfect for tenants who prefer the ease of one-story living. The two rear units are thoughtfully designed as two-story layouts, with living, kitchen, and entertaining space on the main level, and all bedrooms and bathrooms tucked upstairs for privacy. From an investment standpoint, the numbers speak for themselves. The units are currently rented at $6,500, $4,500, and $3,400 per month, bringing in a total annual income of $172,800 on long-term leases--steady, reliable cash flow in one of the most in-demand rental markets in the country. And then there's the location. You're just minutes from the coastline and a quick ride to downtown Key West, where all the restaurants, nightlife, and charm come together. Tenants love it here--which is exactly what you want as an owner. Whether you're looking to expand your portfolio or secure a high-performing asset in the Florida Keys, this triplex checks all the boxes.

1821 Harris Ave, Key West

$2,800,000
4 Beds 3 Baths 619615 MLS
SPECIAL DAILY TRANSIENT LICENSE!!! Experience one of the Lower Keys' rarest offerings at 21640 Overseas Highway,an extraordinary 1.2 acre open-water estate with panoramic ocean views, resort style amenities, and true investment upside. Opportunities like this almost never come to market from Key West to Summerland. With 3,286 sq ft per appraisal, this 4-bedroom waterfront residence delivers the scale, privacy, and setting luxury buyers search for but rarely find. From the moment you enter, the home is designed around the water. Expansive living areas, soaring ceilings, and oversized windows frame endless blue views while natural light fills the interior. The spacious layout offers multiple entertaining zones, generous bedroom suites, and the kind of footprint that allows a buyer to enjoy immediately or elevate into a signature Keys showplace. Outside is where this property separates itself from nearly everything else on the market. The massive parcel creates room to breathe, entertain, and enjoy waterfront living on a level almost impossible to replicate today. A private pool, sandy beach area, dockage, mature tropical grounds, and open-water backdrop combine to create a true resort atmosphere. Sunrise coffee, sunset cocktails, paddleboarding, boating, and stargazing all happen from your own backyard. Under the home, an immense garage / storage / workshop space offers rare functionality for collectors, boating gear, vehicles, trailers, hobbies, or business use. Very few waterfront homes in the Keys offer this level of usable enclosed space. For investors, this property's transient rental license potential is a major value driver. Large open-water estates with acreage and premium amenities command exceptional demand in the vacation market. With the right presentation and management plan, this is the type of asset that can serve as both a personal retreat and a high-performing income property. Lets take a look!!!

21640 Overseas Hwy, Cudjoe

$1,150,000
2 Beds 2 Baths 619610 MLS
Welcome to 1025 Elgin Lane, an exquisite residence nestled in the heart of Key West's Historic Seaport District. This recently updated home seamlessly blends historic charm with modern comforts, offering an unparalleled living experience in one of Florida's most sought-after locales. The interiors are adorned with original Dade County Pine walls and flooring, exuding warmth and character that pay homage to the home's rich heritage. Recent enhancements have elevated the home's functionality and aesthetic appeal including a new foundation, beautiful new flooring, tastefully updated bathrooms, and fresh paint inside and outside. The home features high ceilings with exposed beams and French doors that open to a private patio. This outdoor space is perfect for morning coffee or evening gatherings under the stars. The second-floor primary suite offers a private sanctuary, complete with a walk-in closet and an en-suite bathroom featuring a classic clawfoot tub. The downstairs bedroom is generously sized and includes a walk-in closet. The private patio, accessible through French doors, is ideal for alfresco dining and relaxation. The front porch offers a quiet spot to enjoy the tranquility of Elgin Lane, a quiet lane that ensures privacy and minimal traffic. A designated off-street parking space adds to the convenience of this property. A private walkway provides direct access to Eaton Street, placing local bakeries, shops, and the vibrant Seaport just steps away. Situated less than a block from the renowned Old Town Bakery and just two blocks from the lively Seaport, this home offers unparalleled access to Key West's finest dining, shopping, and entertainment venues. Whether you're seeking a serene personal retreat or a lucrative investment property, this residence offers an exceptional opportunity to own a piece of Key West's storied history.

1025 Elgin Ln, Key West

$574,000
2 Beds 1 Baths 619605 MLS
Only 6 homes in from the Beach! Located in the highly desirable Largo Sound Park neighborhood, this concrete conch home offers exclusive access to a private community park featuring a sandy beach, boat ramp, and pavilion with restrooms- all for you to enjoy the Keys lifestyle! Full of character and Old Florida charm this 2 bedroom home features a bright and open floor plan with terrazzo floors and a new roof in 2023. Off of the kitchen, there is a huge screened patio under roof that connects to a workshop - great for additional living space with excellent potential! The fully fenced yard provides ample room for multiple vehicles and a boat trailer. The spacious backyard offers endless possibilities, with plenty of room to add a pool, create an outdoor entertaining area, or simply enjoy the wide open space. This is a great opportunity to own in Largo Sound Park right by the Homeowner's park and make this house your very own! This rare location is something truly special! Live the Keys lifestyle!

56 Se Marlin Ave, Key Largo