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701 Spanish Main Dr Unit 140, Cudjoe
$399,900
2 Beds ⋅ 1 Baths ⋅ 618353 MLS
This charming and meticulously maintained property is perfect for anyone looking to start enjoying the tropical paradise of the Florida Keys. It comes fully furnished with a cozy coastal style and features 2 bedroom, 1 bathroom, and an enclosed patio area with a pull-out bed and living area. The living room is bright and spacious, while the kitchen is open and easily accessible for entertaining on the patio. The garden patio at the entrance is an ideal spot to admire the beautiful mornings and evenings outside. Conveniently located in the popular Venture Out Park, this property offers all the amenities you could want. This includes a ships store, marina with fuel docks, boat ramp, large, heated pool with a saltwater filtration system, spa, showers, kiddie pool, tennis courts, pickleball courts, and even a post office, all within a secure, guard-gated entrance. Additionally, Venture Out allows for daily, weekly, and monthly rentals, making it a true paradise!

701 Spanish Main Dr Unit 140, Cudjoe

914 S Emerald Dr, Key Largo
$399,750
2 Beds ⋅ 2 Baths ⋅ 618726 MLS
SUPER BRIGHT AND SPACIOUS!! THIS 2/2 HOME IS LOCATED IN SILVER SHORES AN ''OVER 55'' FULLY GATED COMMUNITY! THE HOME HAS BEEN REMODELED WITH AN OPEN FLOOR PLAN DESIGN AND ALL FLOORING IN THE HOME IS TILED FOR EASY MAINTENANCE. THE HOME COMES FULLY FURNISHED AND IT HAS AN OVERSIZED FRONT SCREEN PORCH SO YOU CAN ENJOY THE FRESH AIR AS YOU ARE ABLE TO GET A CROSS BREEZE WHEN YOU OPEN THE FRONT SLIDING DOOR AND THE SIDE DOOR WHICH IS ALSO IN A COVERED SCREENED AREA. SILVER SHORES FEATURES A CLUBHOUSE, HEATED AND CHILLED POOL, A MARINA, SHUFFLEBOARD, TENNIS, PICKLEBALL, AND BOCCE COURTS. PLUS LOTS OF FUN PARTIES, EVENTS AND ACTIVITIES FOR THOSE THAT LIKE TO STAY ACTIVE. YOU WILL LOVE LIVING IN SILVER SHORES EITHER ON A FULL TIME, SEASONAL, OR JUST WEEKENDS. THE SELLER HAS PAID THE INITIAL $25K ON THE SPECIAL ASSESSMENT.

914 S Emerald Dr, Key Largo

220 14th St, Key Colony
$399,000
5 Beds ⋅ 5 Baths ⋅ 621357 MLS
Discover an effortless way to experience the Florida Keys with this one-eighth ownership opportunity, a beautifully appointed waterfront residence in sought-after Key Colony Beach. Part of the Pacaso co-ownership program, this fully furnished and professionally managed home offers a sophisticated approach to second-home ownership. Set along a peaceful canal, the two-story residence features covered balconies, tropical landscaping and private dockage with convenient access to both the Atlantic Ocean and Gulf of Mexico. Inside, the light-filled great room features high ceilings and opens directly to the covered outdoor kitchen, dining area and pool. The gourmet kitchen is designed for gathering with Thermador appliances, white cabinetry, custom range hood, generous counter space and a large island with seating. The primary suite offers a spa-inspired bath with dual vanities, soaking tub and tiled shower. Four additional bedrooms, each with a private bath, provide plenty of space for family and guests. Upstairs, a second family room with wet bar and wine refrigerator opens to a balcony overlooking the canal. Outside, an east-facing pool and hot tub welcome the morning sun, while the covered outdoor kitchen and dining area make year-round entertaining easy. Private dockage puts boating, fishing and days on the water just steps from home. Professionally designed, fully furnished and managed through Pacaso, this property offers the opportunity to own your share of the Florida Keys lifestyle and simply arrive, settle in and enjoy.

220 14th St, Key Colony

218 Schooner Ln, Duck
$399,000
621297 MLS
Rare oversized lot in the heart of Duck Key: 12,099 SF, a lot and a half, well above the typical 7,500 to 7,800 SF lots found throughout the island. The property offers 128' of frontage with a 100' lot depth, exceptional dimensions for a custom island retreat. The lot sits in a favorable flood zone, has no wetlands, and is free of invasive plant species, a clean canvas ready for design. Public sewer is available; no plans or ROGO permit convey with the sale, so buyer to verify with the county. Three houses down, new construction on a 7,500 SF lot recently sold for $2,000,000, underscoring the upside on a lot nearly double the size. Owner will consider owner financing with a minimum 50% down payment. Duck Key delivers the authentic Keys lifestyle: crystal clear waters, easy access to deep drops just outside the island for world-class deep sea fishing, and nearby sandbars like Grassy Key for weekend gatherings. The island is home to a Michelin-rated chef's restaurant, and an optional HOA offers a pool, tennis courts, and additional amenities. Duck Key also has a marina where owners can arrange paid boat storage ahead of storms or hurricanes. Unlike much of the Keys, Duck Key enforces monthly rather than weekly rental minimums, preserving a quieter, more residential feel with less transient tourism, the calm, tropical, island-style living Duck Key is known for. 2025 property taxes were $1,388, which does not reflect any exemptions.

218 Schooner Ln, Duck

27305 Guadaloupe Ln, Ramrod
$399,000
621287 MLS
Permitted to build your Florida Keys retreat at 27305 Guadalupe Lane on Ramrod Key. This vacant lot offers a documented permitting history for a single-family modular home. Permit shows ROGO approval and a permit revision approving 75 cubic yards of fill and land clearing. Certain green-building requirements, including solar panels, a cistern and a gray-water recycling system, are not reflected in the existing permit documents, potentially representing savings of $50,000 or more. Buyer will need to obtain updated home plans, as the modular home referenced in the existing permit is no longer available and will be subject to County review and approval. Permit documents are available under the Documents tab in the MLS. Buyer to verify current permit validity, ROGO allocation status, approved site work, environmental requirements and all remaining development conditions.

27305 Guadaloupe Ln, Ramrod

2600 Overseas Highway Unit 48, Marathon
$399,000
2 Beds ⋅ 3 Baths ⋅ 620168 MLS
Classic Keys Beach House Vibe with Proven Rental Income! Discover the ultimate Florida Keys getaway and investment opportunity with this 2-bedroom, 2.5-bathroom beachfront townhouse at Tranquility Bay Beach Resort in Marathon. Perfectly situated on the highly sought-after ''quiet side'' of the resort, this villa offers serene Gulf views and immediate proximity to the adult-only pool, the beach and the beautifully manicured Jack Nicklaus-designed putting greens. Tranquility Bay is a world-class, full-service resort featuring a pristine private beach, a beachside Tiki bar, three sparkling swimming pools (including a dedicated kids' pool and a tranquil adult pool), and the award-winning gourmet dining experience at the Butterfly Cafe. This property is a hands-free, turn-key investment. Owners are required to participate in the exceptional onsite nightly rental program, which completely manages the property for you. In 2025, this unit generated $51,000 in rental income to the owner. Enjoy up to 5 weeks of personal paradise each year while letting the resort handle the rest. Don't miss your chance to own a piece of the Keys lifestyle that pays you back!

2600 Overseas Highway Unit 48, Marathon

135 Airstream Ln, Tavernier
$399,000
2 Beds ⋅ 1 Baths ⋅ 618336 MLS
This two bedroom, one bathroom home within the Village of Islamorada is perfectly situated with close proximity to the Florida Bay and breathtaking bay and sunset views! Property is on a 3,600 SF parcel. A large screened porch is attached for lovely outdoor living. Separate laundry facility and storage building on site. Also included is a Keys style concrete guest cottage behind the home. This property has an immediate building right should you choose to demo and rebuild. A quote is available to demo and re-build a 1,169 SF, three bedroom, three bathroom new modular residence. The home is conveniently located near Founders Park, restaurants, schools and shopping. This is a fantastic opportunity to find your place in the Florida Keys!

135 Airstream Ln, Tavernier

812 Fleming St Unit 2, Key West
$399,000
1 Beds ⋅ 1 Baths ⋅ 614786 MLS
Boutique commercial, ground floor office condo for sale in Old Town at Seafoam Condominiums. Only one of two Commercial units in the building. This 665 sf. office is turnkey and perfect for Professionals looking for a small office to own vs. paying rent every month. Great location and close to everything in Old town either by walking or biking. Exterior has several large pane windows for natural light inside. To enter off the sidewalk there are a set of gorgeous, hand made mahogany french doors. Also, there is an interior side door for private access. Interior has 12' ceilings and the layout includes front seating area with a receptionist window, administrators office and private office in rear. Half bath is ADA compliant. This unit has been totally renovated and ready to move in. Renovations include new Brazilian cherry wood floors & keystone flooring in the bathroom. upgraded electric and lighting, freshly painted, Central AC and wireless Security system. Seafoam building has coded entrance, atrium hallways and large in-ground concrete pool exclusively for Condo owners and guests. HOA fee of $1,286/mos. includes insurances and reserves. Includes Liability, Wind and Flood insurance. Building has never flooded and in X flood zone. Building is up to date with SIRS and milestone inspections. Additional $587/mos. special assessment for windstorm insurance. Same owner since 2008. Owner will consider lease with Option to Purchase. Asking rent is $4,000/mos.

812 Fleming St Unit 2, Key West

48 Shoreland Dr, Key Largo
$399,000
614821 MLS
.Exceptional corner lot available in Key Largo on the corner of Shoreland and Transylvania Avenues in Largo Sound Park. This highly desirable location at MM103 ocean side is a stones throw from the Hideaway, marina and dive facilities. Neighborhood owners park and ramp is just a few yards down the street in view for easy access to Largo Sound, Pennecamp Park, the reef and open ocean access. A short ride through nearby Adams Cut takes you to the back county, Florida Bay and the best in back country fishing. This lot is in the building permit system waiting on it's turn build. Get in now and put your finishing touches on the plans while you can. Quaint, quiet and close to all that is Key Largo, this location puts you close to the charm of Key Largo but just off the beaten path. Call today for more information.

48 Shoreland Dr, Key Largo

143 S Indies Dr, Duck
$398,000
618535 MLS
Ready to build! This property includes a transferable development right (TBR) that is already secured to the lot, making it ROGO-exempt and ready to build today. Even better, the TBR does not expire, giving you the flexibility to build now or hold the property and build later with no time pressure. Situated on a spacious corner lot on a desirable street, the property is located just one block from Club Duck Key, where members enjoy resort-style amenities including a swimming pool, jacuzzi, tennis and pickleball courts, and a clubhouse -- all enhancing the relaxed island lifestyle Duck Key is known for. For boaters, the location is equally appealing. Store your boat at Duck Key Marina and enjoy convenient, seamless access to the open water, world-class fishing, and endless days on the bay or ocean. Just minutes away, the renowned Hawks Cay Resort offers additional dining, marina services, watersports, and spa amenities, giving owners the option to enjoy a full resort experience close to home. Duck Key is widely regarded as one of the most desirable communities in the Middle Keys, prized for its peaceful atmosphere, well-maintained homes, boating lifestyle, and easy access to both Marathon and Islamorada. With no ROGO wait, no uncertainty, and a build-ready path forward, this is a rare chance to design and build your dream home in paradise -- on the only ROGO-exempt lot currently available on Duck Key.

143 S Indies Dr, Duck

408 Calle Limon, Marathon
$397,000
620904 MLS
It is no secret that the Sombrero Beach neighborhood is one of the most highly sought after established neighborhoods in all of Marathon. Rarely does a vacant lot become available with a building right already attached to it. What makes this 7,125 sqft lot even more rare is that this one comes with approved plans to build a 4 bed, 3 bath, 1966 sqft living home with a 299 sqft rear porch & 75 sqft front porch by the well-respected local builders, Design Center. To make things even easier for the buyers, a local lender is offering up to 80% LTV Construction Financing, allowing you to purchase the lot and fund the construction all at once. It is important to note that this building right is designated SOLEY for local Marathon residents who will make this their Homesteaded primary residence for a minimum of 2 years. This provides a great opportunity for a local family to live in this incredible neighborhood that is walking distance to Sombrero Beach and minutes to Marathon High School. Don't miss the rare opportunity.

408 Calle Limon, Marathon

24285 W Caribbean Dr, Summerland
$395,000
620006 MLS
Purchase this deep draft canal front LOT in Summerland Key in the Florida Keys. The building permit is in-process for a 3 bedroom/ 2 bath stilted single family residence (cost of the home is additional). The plans shown are for a 1320 sq ft' 3/2 elevated Affinity home with features that include impact doors and windows and built to 180 mph which is great for your insurance rates. This canal has incredibly easy access to the Atlantic and Gulf with deep draft. Buy the land now and when your permit comes in, you can start building or you can change the plans. Price does not include the home and will increase as construction progresses. Limited lots are available in this upscale neighborhood. DOCK permit update from Army Corp.

24285 W Caribbean Dr, Summerland

5701 Overseas Highway Unit 1, Marathon
$395,000
1 Baths ⋅ 619320 MLS
The Premier Office in First Professional Centre! Secure the only unit in this 17-unit complex with direct Overseas Highway frontage for maximum brand exposure. Unit 1 offers 1,128 SF of versatile space--significantly larger than the standard units in the building. The professional floor plan features a welcoming reception area with a built-in desk, three spacious private offices, a convenient kitchen area, and a half bath. Surrounded by windows, the space is flooded with natural light, creating an inviting environment for clients and staff alike. Ideal for medical, legal, accounting or other professionals. Currently occupied but will be delivered vacant as of July 1st. Own the best-positioned office in Marathon today, please call for a private showing.

5701 Overseas Highway Unit 1, Marathon

Vacant Lot Vacant, Big Pine
$395,000
614178 MLS
Prime Commercial Fishing Property in the Florida Keys! Discover a rare opportunity to own and operate a commercial fishing business in the coveted Commercial Fishing Special District of Big Pine, FL. This unique zoning allows unparalleled access to open water, making it a fisherman's paradise. Here are the highlights: - Buildable Property: Your vision can come to life with ease on this buildable lot. - AE Flood Zone: Favorable flood zone location for peace of mind. - Endangered Species Free: Not restricted by endangered species listings. - Commercial Vessel Accommodation: Control depth tailored to fit commercial fishing vessels. - Large Corner Lot: Expansive nearly 1/2 acre lot, offering ample space. - Bayside Location: Situated in Big Pine on the tranquil Bayside, with quick access to the water. This property represents a rare and valuable investment opportunity with its unique zoning, generous lot size, and prime location. It stands out as one of the few remaining parcels that cater specifically to the commercial fishing industry. Act now to secure this sophisticated and financially advantageous piece of real estate in the beautiful Florida Keys! Contact us today for more information or to schedule a viewing. Don't miss out on this exclusive chance to elevate your business!

Vacant Lot Vacant, Big Pine

3314 Northside Dr Unit 46, Key West
$392,000
2 Beds ⋅ 3 Baths ⋅ 615693 MLS
This is a SHORT SALE and is subject to lender approval. Opportunity for you to have an island of Key West lifestyle! Whether a primary home or investment, this condo should be on your list -- great location, multi-level living, and covered deeded parking. Located near the center of the island conveniently located close to shopping plazas, movie theater, schools and dining as well as being just a few minutes from the heart of Old Town Key West. With two bedrooms and two bath, plus a central area half bath, and private patio, this home is an attractive option for any Buyer wanting Key West island living. The condo complex has a large pool for residents' use and the monthly condo fee includes exterior building insurance and maintenance. It is a great day to be in Key West each and every day!

3314 Northside Dr Unit 46, Key West

325 Calusa St Unit # 58, Key Largo
$390,000
2 Beds ⋅ 1 Baths ⋅ 621020 MLS
Priced to sell ! Spacious 1750 sq ft lot in desirable Calusa Campground, Key Largo. Discover your slice of paradise in the highly sought- after community. fulls keys living at an affordable price! Fully set up for comfort, relaxing and convenience. Property features a well maintained trailer that sleeps up to 10, paver and tiled surfaces throughout, covered carport/patio ideal for outdoor living and utility shed for extra storage. Enjoy resort style amenities: boat launch, golf-cart friendly streets, swimming pool, clubhouse, laundry facility, tennis, basketball, children's playground, picnic area and beautiful bay front Sunsets. Lot is rentable for short-or long term stays. The perfect Key's retreat or income-producing property.

325 Calusa St Unit # 58, Key Largo

31368 Ave E, Big Pine
$385,000
3 Beds ⋅ 2 Baths ⋅ 620783 MLS
Nestled in a quiet neighborhood on Big Pine Key, this property presents a rare opportunity to create your own Lower Keys retreat. Situated on a spacious 10,000 sq ft lot, the 3 bedroom, 2 bathroom home features an expansive floor plan with all-new sub-flooring already in place, providing a solid foundation for your vision. Whether you're looking to thoughtfully renovate the existing home or take advantage of its ROGO exemption status to build new, the possibilities are yours to explore. Experience the laid-back charm of Big Pine Key, where community parks, local restaurants and bars, shopping, and nearby boat ramps are all just minutes away. This property offers the perfect opportunity to create the island home you've always imagined in a peaceful setting in the Lower Keys.

31368 Ave E, Big Pine

2539 Coolidge St, Other
$384,900
1 Beds ⋅ 1 Baths ⋅ 621037 MLS
Fabulous opportunity to own this beautifully updated concrete home in ''The Presidents'' section of Hollywood, ideally located just 3 miles from the beach and approximately 1 mile from the boutique shops, restaurants, and entertainment of Hollywood Boulevard. Situated in desirable Flood Zone X, this property offers the significant advantage of being outside the high-risk flood zone--an important consideration for insurance costs. The well-maintained home features a generously sized primary bedroom with an updated ensuite bath featuring a frameless glass shower enclosure and an enormous walk-in closet. An enclosed sleeping porch provides flexible additional space for futons or beds, making this an excellent primary residence, couples' retreat, or potential vacation property. The inviting galley kitchen features wood cabinetry, granite countertops, and stainless steel appliances, while tiled floors throughout provide easy-care Florida living. A separate laundry room includes a new washer and dryer. An oversized, security-enclosed carport offers tremendous additional potential and could possibly be converted to create another bedroom and bath or private in-law suite with its own exterior entrance, subject to applicable permitting and approvals. Enjoy the enduring quality and peace of mind of CBS concrete construction, impact windows and doors, a new roof, and a central A/C system that is just one year old. Enjoy the enormous, fully fenced tropical yard that spans from street to street, with a dedicated alleyway street providing convenient rear access. Mature fruit trees, numerous palms, and charming brick walkways punctuate the lush outdoor setting and create a wonderful sense of privacy. With plenty of room for a pool, tiki hut, outdoor kitchen, or expansive entertaining area, the possibilities are endless for creating your own private South Florida resort lifestyle! Live the Florida lifestyle in the heart of Hollywood,close to the beach, dining, shopping, and

2539 Coolidge St, Other

2000 Coco Plum Dr Unit 302, Marathon
$379,000
1 Beds ⋅ 2 Baths ⋅ 621184 MLS
Perched above the shimmering Coco Plum Channel, this beautifully reimagined one bedroom, one- and-a-half bath residence at Bonefish Towers offers ocean views from every window -- a rare opportunity to own in one of Coco Plum 's most coveted addresses. Thoughtfully renovated throughout, the residence showcases a crisp, coastal-inspired aesthetic complemented by raised ceilings in the master bath, kitchen, and foyer. Every detail has been elevated, from the brand-new impact windows and sliding glass doors to the updated air conditioning, kitchen, flooring, electric blinds and so much more. This home is being offered furnished. As one of only thirteen residences in the building with two balconies, it offers an exceptional setting for indoor-outdoor living and unobstructed water views. Resort amenities in the community include a heating swimming pool, update fitness center, tennis/pickleball court, waterfront tiki hut/fishing station, waterfront BBQ area, 24 hour security and plenty of parking. The building is in great shape with two new elevators, a new roof and new exterior paint.

2000 Coco Plum Dr Unit 302, Marathon