Divider
Content Divider

Middle Keys Real Estate for Sale, Homes and Condos in the Florida Keys

Total Listings 425
Order By:

$799,000
Marathon
Puerta Del Sol   - MM: 50.50
4 Bed, 4 Baths, 2,074 SqFt Days Listed: 126
Multi-Units - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Triplex in the heart of Marathon. Configured as 3/1, 1/1, and studio apartment. Great income property fully occupied. On 10,000 sf lot with large storage in back. Great quiet neighborhood close to the ocean.

$799,000
Marathon
Coco Plum Villas   - MM: 54.50
2 Bed, 2 Baths, 1,280 SqFt Days Listed: 31
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Cut/Natural

Enjoy this DIRECT Oceanfront end unit that offers a serene coastal lifestyle with stunning views! This well-maintained furnished condo is an ideal choice for those seeking a permanent home or a relaxing vacation getaway! Call today to schedule a tour!

$799,500
Marathon
Ocean Isles Fishing   - MM: 52.50
1 Bed, 1 Baths, 1,136 SqFt Days Listed: 307
Condo - Active - Waterfront No
Side of Island: Ocean - Dockage: Boat Ramp,First Come

Brand New Oceanfront Complex never lived in. Concrete construction in the heart of Marathon. This complex allows minimum seven day rentals. Impact doors & windows, metal roof, aluminum railings. Oceanfront club house for everyone to enjoy, a boat ramp and new marina with boat slips for homeowners only. The marina gives you ocean or gulf access thru Vaca Cut.

$799,900
Marathon
Marameade Amd   - MM: 49.50
2 Bed, 2 Baths, 1,053 SqFt Days Listed: 177
Half Duplex - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 32ft.

Extraordinary in every way! Casa Kokomo is your ticket to chic island living. Enjoy and/or make money from Day One! Exquisitely furnished and updated and super comfortable 2 bedroom / 1 Bath waterfront half-duplex that is the perfect getaway and/or investment property that is ideal for pampered vacation rentals. 7-day rentals permitted. Gated and serenely private. Exceptional and fresh updates throughout the entire home. Newer central and ductless A/Cs, new stainless kitchen with Gas stove, freshly updated bathroom, updated water heater, metal roof. Light bright and relaxing Sunroom overlooks the canal, relaxing hot tub and alfresco dining. 32-foot concrete dock with easy access to open water. Great parking. Close proximity to Sombrero Beach. Major shops, Theater, restaurants, and Boutiques are less that 1/4 mile away. World-class fishing, diving, and sandbar hopping are just a quick boat ride away. Phenomenal rental potential. Sellers have started short term rentals this year with exceptional results. Opportunity is Knocking ... Loudly!!

$800,000
Marathon
Bonefish Towers   - MM: 54.50
1 Bed, 1 Baths, 513 SqFt Days Listed: 84
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

Beautiful 5th floor unit with the view of the Gulf, the Marina, Pool and Tiki Hut.This unit has been completely renovated from floor to ceiling, including plumbing, electrical, AC and all new windows.This has been renovated with the top of the line appliances, flooring and fixtures.Truly an amazing unit at Bonefish Towers with views to enjoy all day!Come see for yourself it is move in ready nothing to fix just bring your clothes.This complex offers a secure building, brand new roof, new elevators a Tennis Court, Beautiful updated bath house and new gym area and new equipment, a Fish cleaning dock, shuffleboard, community patio with grills, Tiki huts one on the point and one near the pool area.Also, a car wash station.

$800,000
Duck Key
Plantation Island   - MM: 61.00
2 Bed, 2 Baths, 1,170 SqFt Days Listed: 23
Single Family - Active - Waterfront No
Side of Island: Median - Dockage: None

Affordable Duck Key Home with Endless PotentialHeres your chance to own a slice of paradise on the highly desired Duck Key! This estate-sale property is an incredible entry-level opportunity to enjoy island living with plenty of room to make it your own.The main level features an open-concept living, kitchen, and dining area that extends to a large deck overlooking your private in-ground pool--a perfect spot for morning coffee or evening sunsets. With two bedrooms and two baths on the main floor, theres plenty of space for relaxation and guests.The lower level includes covered parking, a large storage room, and a patio that opens directly to the pool area. The 7,500-square-foot lot offers endless outdoor opportunities, including space to park your boat, store vehicles, or add a tiki hut or outdoor kitchen to create your dream island retreat.While the home needs some updates, its brimming with potential to become a full-time residence, vacation escape, or investment property. If youve been waiting for a chance to be on Duck Key at a fantastic value--this is it!

$817,500
Key Colony
Key Colony Beach   - MM: 53.50
2 Bed, 2 Baths, 1,573 SqFt Days Listed: 14
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Convenient, spacious and private are many of the words used to describe this elegant ranch style island home. Featuring an attached carport where you can simply drive to your front door! There are no long flights of stairs to climb, offering ease and comfort. This single floor home is elevated above flood and has low transferable insurance. When you enter the home you will be impressed by the spacious floor plan, high vaulted ceilings, and large private screened in porch overlooking the private, tropical fenced in back yard. The impressive interior accommodations include Brazilian cherry hardwood flooring throughout, upgraded LED lighting for energy savings and an updated kitchen with granite counter tops. The exterior of this home boasts a newer roof from 2018 and a new 13.5KW generator offering safety and security. There is also a separate office and laundry room that is accessed from the covered parking area, or back porch. Close and conveniently located near grocery stores, hospital, restaurants, and major shopping outlets. Catch the evening sunset at the Sunset Park. There is also a community golf course, tennis, pickleball and bocce courts located right down the street. The owners have generously offered to pay for one year passes to the private beach, only five minutes walking distance away. This private island sanctuary on Key Colony Beach offers the ideal combination of island living and modern conveniences. Imagine all that awaits you in this friendly island neighborhood! Call now to schedule your very own private showing, this opportunity will not last!

$820,000
Marathon
Grassy Key   - MM: 58.90
3 Bed, 3 Baths, 1,230 SqFt Days Listed: 185
Single Family - Contingent - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Welcome to 71 Dorsett Dr. This 3 bedroom / 2 bath concrete home is waiting for you to move in. Enter the home from a generous platformed staircase to enjoy spacious living areas with updated kitchen, separate laundry room, all new impact windows, new roof and updated bath. There is covered parking for 2 plus off-street parking and room on the side for your boat trailer, as well as a large enclosed workshop and tons of lower level space. There is much more to this property than meets the eye. There are a few nearby public boat ramps and the property owners on Dorsett enjoy some private boat ramp privileges. Please call for more information. Schedule a walk thru of your new Keys Home today!

$825,000
Marathon
Harbor Isle   - MM: 48.50
3 Bed, 3 Baths, 1,279 SqFt Days Listed: 78
Mobile Home - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift60ft.Concre

This home is in an excellent location on a deep water canal and Boot Key Harbor protection. Easy Boat access to Atlantic & Gulf. Walk or Bike to restaurants, beach, grocery stores and Home Depot, Boat ready with 15,000 lb. Lift on a 60 concrete seawall. This fully furnished 2 Bedroom 2 Bath home is the epitome of comfort & convenience, offering a wide range of features that cater to a relaxing and easy going lifestyle. A 3rd bedroom was converted to open social space with a Murphy Bed for additional Guest. The Home is incased in durable vinyl siding and features impact windows, providing a safe haven from the elements. The Interior has been thoughtfully upgraded,, featuring ceramic tile flooring. An open concept living/dining/kitchen that fosters a sense of unity and togetherness. The Kitchen is a Chefs delight with sleek Granit countertops, wine cooler, ample cabinet space, double pantry & stainless steel Appliances. Facing the Canal there is wall to wall Bay Windows providing full water view & sunlight. A Common Bathroom boasting a double vanity, 2 Large Bedrooms with a King bed and Bathroom in Master Suite and a Queen bed & Futon in 2nd Bedroom. Each room if fitted with window treatments & Blackouts for added privacy and comfort. Ample Closet space ensuring all your storage needs & a Washer/Dryer. For outdoor lovers the screened porch is a perfect retreat. It comes with comfortable fans for those warmer days & a built in Hot Tub for ultimate relaxation. A 2nd covered porch facing the canal with views of Boot Key Harbor & partial Sunsets. Property boast a fish cleaning station, water & electric on the Dock. An outdoor shower adds a touch of luxury to your beach days. The storage/workshop offers ample space for your tools & projects. Partially fenced, features trailer storage & excellent parking options. If you are looking for a vacation home, permanent residence or Rental Income 835 25th St. offers an affordable waterfront lifestyle thats hard to beat.

$829,400
Marathon
Flamingo Island   - MM: 49.50
3 Bed, 3 Baths, 1,120 SqFt Days Listed: 71
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Welcome to 598 Copa D Oro, a charming retreat located in the highly sought-after neighborhood of Flamingo Island in Marathon. 3 bedroom 2 bathroom home with fantastic bonus room buyers must see to appreciate. Perfectly situated near Sombrero Beach, offering easy access to restaurants, entertainment, and the turquoise blue waters of the Florida Keys. The open floor plan creates a welcoming space for gatherings, and the private balcony provides a peaceful spot to enjoy the tropical breezes.Set on a spacious lot, this property offers ample room for boats, trailers, storage, or parking, making it ideal for boating enthusiasts. With quick access to open water, youll enjoy some of the best fishing and water activities the Keys have to offer. Whether youre looking for a permanent residence, a vacation home, or an investment opportunity, this property captures the essence of island living. Dont miss your chance to make it yours!

$834,999
Marathon
N Marathon Shores   - MM: 51.50
3 Bed, 3 Baths, 1,693 SqFt Days Listed: 134
-4.57% ($40,001) 3 Price Changes : Last Change 45 Days Ago
Single Family - Contingent - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

For the entertainer in you! This home is so well laid out for entertaining, both inside & out! This beautifully upgraded and well maintained home exudes a vibe of peace & tranquility the moment you step inside! Youll fall in love with the spaciousness of the split floor plan offering 3 bedrooms and 2 full baths. Youll love the ease of entertaining in the upgraded chefs kitchen and outdoor cooking area! Youll love the ease of maintenance with impact resistant doors and windows! Youll love the oversized corner homesite with fully fenced back yard thats big enough to add a pool!What we love about this home is the location! You are steps from the boat ramp, just minutes from shopping & dining and an easy drive to the airports in Miami and Key West!Book your private tour now and see what we mean! This is truly a must see with almost 1700sf of living space under air!

$835,000
Key Colony
Monte Christo   - MM: 53.50
2 Bed, 2 Baths, 1,260 SqFt Days Listed: 22
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

Stunning Oceanfront Condo with Breathtaking Views ! Step into coastal luxury with this beautifully designed 2 bedroom 2 bathroom oceanfront condo at Monte Christo. Situated just steps from the golden sands of the beach, this unit captures the essence of beachside living where sunrise and sunset views are unmatched. The master suite is your own private retreat, with a king-sized bed, direct patio access, and, of course, those stunning ocean views. The second bedroom is equally as inviting, with ample closet space and a serene atmosphere. Updated Kitchen and Laundry room inside the unit. This Unit is currently in the Vacation Rental Program.Other amenities include 2 resort-style pools, assigned detached one-car garage, tennis court and shuffleboard. With its prime location on Key Colony Beach, youll have easy access to all the best restaurants, shopping, and entertainment, yet still enjoy the tranquility of oceanfront living.Dont miss your chance to own this piece of paradise. Schedule a tour today and experience the magic of living on the beach.

$849,000
Duck Key
Marina Vil Hwks Cay   - MM: 61.00
3 Bed, 3 Baths, 1,364 SqFt Days Listed: 656
-43.21% ($646,000) 9 Price Changes : Last Change 2 Days Ago
Condo - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Other Dockage

Seller has this property listed with VRBO. Rental income for 2024 was over $80,000 for the year. Wide water views from this beautiful renovated furnished condo boasting a fantastic floor plan compared to other condos, is attractively decorated with an updated and modern coastal look. Many windows for natural light and a huge L-shaped balcony boasting pocket sliding doors for indoor/outdoor living space. Kitchen has white countertops, newer SS appliances, and a terrific bar/butlers pantry w/ wine refrigerator. Main bedroom opens to the balcony, has large step-in shower and dual sinks. Other features include impact glass windows & doors, natural stone floors, plantation shutters, a barn door, extra storage and covered parking (trucks & pets OK). Full-time residents can homestead this property and receive mail or use as a vacation home with the option to rent through on-site Hawks Cay or personally through rental outlet of your choice (Airbnb, VRBO, VACASA, etc.). Optional membership to resort fitness center, tennis, kids and adult activities. Seller will respond to all offers.

$849,990
Marathon
Seawatch   - MM: 53.50
3 Bed, 3 Baths, 1,602 SqFt Days Listed: 102
-2.91% ($25,510) 1 Price Change : Last Change 1 Day Ago
Condo - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Other Dockage,None

Be prepared to fall in love with Seawatch in Marathon. Featuring 48 units situated on 17 lush acres of manicured grounds, this community is ideal for those who enjoy seclusion and amenities galore. Recently completing Floridas required Milestone Inspection with Reserve Study almost finalized, relax at Unit 104 in Building 6 that features two bedrooms plus a bonus room (used as an office) and two updated bathrooms. Feel one with nature amidst views of the natural hammock and peek-a-boo views of the on-site marina. Step into the stunning Chefs kitchen featuring Carrera quartz countertops and backsplash with a modern, waterfall edged peninsula, white-oak cabinets, and all new appliances including two dishwasher drawers. Find updated ocean blue interior and closet doors with glass paneling. Open the new impact sliders to enjoy a true indoor-outdoor space and plant sanctuary amidst the 400 square foot screened-in porch. Master bathroom is complete with a marble topped double vanity and new glass shower enclosure. Custom shelving in the master closet too. Contemporary guest bathroom with custom tile flooring and walls, opaque glass and black hardware shower enclosure, glass sink, and Carrera quartz topped vanity. With an additional bonus room that would easily convert into a third bedroom, enjoy room for all. If that is not enough, stay active at the tennis & pickleball courts or workout at the on-site gym. Relax by the brand new million-dollar pool and spa. Store your vessel, boat trailer, or even golf cart in the storage barn with 35-foot tall ceilings. Grill out at the on-site pool cabana or host gatherings at the clubhouse. With all of these amenities, youll never want to leave... but if you do, enjoy immediate access to the Gulf or Ocean through Vaca-Cut from the on-site marina (boat slips for rent). With the conveniences of Marathons private airport, grocery stores, and restaurants nearby, this is the way to enjoy the finer things in the Florida Keys!

$859,000
Key Colony
Key Colony Beach   - MM: 53.50
2 Bed, 2 Baths, 900 SqFt Days Listed: 92
Half Duplex - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 30ft.Concrete

Half Duplex in the beautiful community of Key Colony Beach. Remodeled with top quality finishes. Entry doors are Anderson impact, windows are Dbl. Pane PGT, sliding glass doors are Low-E Anderson. All stainless appliances, granite counters, 7 insulation in ceiling throughout, tile flooring, Key Colony Beach offers convenience to its own post office, restaurants, marina, shopping, par 3 golf course, pickleball and tennis courts, basketball, bocce ball, horseshoes. Marathon Airport is only 10 minutes away, Key West International Airport is a 1-hour drive.

$869,000
Key Colony
Monte Christo   - MM: 53.50
2 Bed, 2 Baths, 1,260 SqFt Days Listed: 55
-3.34% ($30,000) 1 Price Change : Last Change 2 Days Ago
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

This is a rare opportunity to own the best priced DIRECT OCEANFRONT 2 bedroom, 2 bathroom condo in Key Colony Beach. Located in the highly exclusive Monte Christo complex, this 1,260 sq. ft. unit offers breathtaking ocean views from the kitchen, dining room, living room, and master bedroom. This meticulously maintained condo is move-in ready, with furniture negotiable, allowing you to personalize the space to your liking. Plus, enjoy the benefits of condo living with no maintenance responsibilities, so you can spend more time enjoying the views and less time on upkeep. The Monte Christo community offers fantastic amenities, including two pools, tennis and shuffleboard courts, and a detached one-car garage. Situated in an ideal location, youre just minutes from Million Air Marathon Airport, Baptist Fishermens Community Hospital, local dining, parks, and marinas, with a short walk to the golf course and professional pickleball courts. Not only is this a beautiful home, but its also a strong investment opportunity with rental bookings already secured for 2025, making it ready to generate immediate rental income. Whether youre looking for a serene oceanfront retreat or a profitable vacation rental, this condo offers unmatched value, comfort, and convenience. Schedule your showing today.

$875,000
Marathon
Sombrero Anglers C N   - MM: 49.50
2 Bed, 2 Baths, 950 SqFt Days Listed: 26
Half Duplex - Contingent - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift44ft.

This charming ELEVATED 2 bedroom, 1 bathroom half-duplex offers the perfect blend of coastal living, privacy, and convenience. Tucked just off Sombrero Beach Road in a peaceful, low traffic neighborhood, this home provides direct deep water access to the Ocean and Gulf via Sisters Creek, ideal for boaters and water enthusiasts. The spacious balcony overlooks a serene lagoon, offering stunning views and easy access for kayaks and paddleboards. Only 1.3 miles from Sombrero Beach, this location combines tranquility with convenience.While Sombrero Beach Road is nearby, the property itself is set on N Anglers Drive, a quiet street free from heavy traffic. Youll also enjoy the nearby walkways and bike path along Sombrero Beach Road, perfect for morning strolls, runs, or bike rides, adding an extra level of ease to your outdoor routine.The home features a metal roof installed in 2017, offering enhanced hurricane protection and potential wind insurance credits. Additional features include a signature swim spa, a 15,000 lb boat lift with a concrete dock, a 475 enclosed storage space downstairs, a metal shed, and a carport with off street parking. Whether youre looking for a full time residence, vacation getaway, or an investment property, this waterfront gem offers exceptional value and endless potential.

$875,000
Duck Key
Village At Hawks Cay   - MM: 61.00
2 Bed, 2 Baths, 950 SqFt Days Listed: 25
Townhouse - Active - Waterfront No
Side of Island: Ocean - Dockage: Dock Privileges,Boat

This beautiful villa at 7101 Harbor Village has 2 bedrooms 2.5 Bathrooms is the combination of luxury, convenience, and investment potential. It includes a deeded boat slip (Unit #29) that can accommodate a 33-foot boat, making it an excellent choice for boating enthusiasts. The villa is currently managed by the owner, and rental income and sellers disclosure details are available upon request. This property offers a prime location with direct access to the ocean, making it a great place to enjoy the Florida Keys lifestyle. The home features granite countertops and stylish finishes, creating a comfortable and modern living space. If you are looking for an investment, this villa can be rented daily. You can choose to enroll it in the Hawks Cay rental program or continue renting it privately. If you prefer, you can keep it as your private getaway and not rent it at all.The villa is close to popular attractions like Angler & Ale, Hawks Cay Resort, and other local restaurants and shops. If you want even more amenities, you can join Club Duck Key, which offers access to a pool, hot tub, tennis, and pickleball courts, social events, and a clubhouse with a full kitchen for an annual membership fee. The home is also just a short drive to Marathon, where you can find grocery stores, restaurants, and other essentials. Key West is about an hour away, and Miami is just a two-hour drive.This is a rare opportunity to own a villa in a highly desirable location. Whether you want a vacation home, an investment property, or both, this villa offers flexibility and great potential. Contact us today to learn more or schedule a private tour.

$875,000
Key Colony
Key Colony Point   - MM: 53.50
3 Bed, 3 Baths, 1,750 SqFt Days Listed: 46
-9.79% ($95,000) 1 Price Change : Last Change 2 Days Ago
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

Here is your perfect Keys Condo with Open Ocean Views & Breathtaking Sunsets! exceptional updates and robust weekly rental history with all excellent reviews. Visit: www.vrbo.com/802170. This residence offers exactly what youve been seeking. The spacious primary suite provides a breathtaking view of the expansive ocean & seamlessly connects to the balcony. The generously sized guest suite, features a walk-in shower and dual vanities, ensuring your guests experience maximum comfort, possibly making it hard for them to leave. The well-designed kitchen is a haven for chefs, ready for delightful meals in the dining room or on the balcony. Key Colony Point welcomes you home with its fantastic pool area, pier, tennis courts, shuffleboard and beachside relaxation, the perfect setting for grilling by the azure waters. Nestled in the Gem of the Florida Keys, Key Colony Beach, this property allows you to explore the entire city on foot or bike, accessing three restaurants, golf, pickleball, marina, tennis courts, playgrounds, post office and Sunset Park. Marathon executive airport is just 5 minutes away, Key West airport is an hour away and Miami airport is approximately a 2-hour drive. Your island getaway awaits you in this idyllic Key Colony Beach residence.

$879,000
Marathon
Little Venice   - MM: 53.00
2 Bed, 2 Baths, 941 SqFt Days Listed: 113
-7.47% ($71,000) 4 Price Changes : Last Change 16 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 52ft.Concrete

ONE OF THE BEST PRICED CANAL HOME IN MARATHON! Charming Key Lime Time - Your Waterfront Retreat Awaits!Step into the ultimate Keys escape with Key Lime Time, a picturesque Conch house currently a successful vacation rental, now available for you to make your own.Open Concept Living Area: Retro-inspired with a cozy vibe, this space is perfect for relaxing nights in, featuring plenty of seating for all to gather.Two Cozy Bedrooms: Both furnished with queen beds and a shared modern bathroom, offering comfort and tranquility after a day of exploring.Outdoor Screened Porch: Enjoy your morning coffee or unwind in the evening while taking in serene water views - the perfect spot to relax and soak in the Florida Keys lifestyle.Fully Equipped Kitchen: Whether youre cooking up a feast or mixing tropical drinks, this kitchen has everything you need, including a double oven, air fryer, grill, drip and Keurig coffee makers, and a blender.Sunset Fishing Off the Dock: Drop a line from the dock and catch snapper as you watch the stunning sunset paint the sky - a true Keys experience.Deep Water Dockage: A 52-foot dock with synthetic decking and a custom floating dock offers easy access for your boat and water adventures. The open-water Atlantic Ocean is just a few homes away! Located on a turquoise canal in the heart of Little Venice, Marathon, Key Lime Time provides direct access to both the Atlantic and Gulf waters, making it ideal for boating, fishing, and enjoying the tranquility of waterfront living. Whether youre seeking a peaceful getaway or a savvy investment opportunity, this enchanting home has it all.Dont miss your chance to own this perfect piece of paradise!

The information being provided by the Florida Keys MLS is exclusively for consumers' personal, non-commercial use, and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. Data last updated on 02-24-2025.
Back To TopMore Info
Terms / Privacy / Accessibility ADA