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

Total Listings 424
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$449,000
Marathon
Little Venice   - MM: 53.00
1 Bed, 1 Baths, 584 SqFt Days Listed: 78
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Charming Conch House that has been fully updated with new roof, impact rated windows & doors, tankless water heater, updated electrical panel, and interior remodel with coastal finishes. This one bedroom & one bath home is affordable retreat for your winter getaway or full-time homestead. Backyard is fully fenced with outdoor spa included for your own tropical ossias. Located in the heart of Marathons Little Venice District. Property can also be used for weekly vacation rentals for cashflow.

$449,000
Marathon
Coco Plum Terraces   - MM: 54.50
1 Bed, 1 Baths, 664 SqFt Days Listed: 67
-4.26% ($20,000) 2 Price Changes : Last Change 10 Days Ago
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Ramp,Other Dock

Welcome to your slice of paradise! This beautifully updated one-bedroom, one-bath condominium offers the ultimate waterfront living experience. Located on a serene 200-foot-wide canal with a 6-foot control depth, its the perfect haven for boating enthusiasts. With assigned boat slips for $500 per year and a community boat ramp steps away, youll have direct access to the water, accommodating boats up to 50 feet in length.Designed for coastal comfort and style, this unit features modern finishes throughout, ensuring a sophisticated and contemporary feel. Whether youre looking for a weekend retreat or an income-generating vacation rental, this property brings in revenue from short-term stays with only a 7 night minimum. Relax and unwind at the heated and chilled pool, or enjoy the tiki hut and boat trailer parking, designed to make your life easier and more enjoyable. With Coco Plum Beach less than 1 mile walk away, stunning views and a private, serene atmosphere, this condominium offers an exceptional lifestyle for both personal enjoyment and investment opportunity.Dont miss out on this rare opportunity to own a piece of luxury waterfront living!

$450,000
Marathon
Key Harbor   - MM: 49.50
1 Bed, 1 Baths, 547 SqFt Days Listed: 103
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Ramp,None

Welcome to Skipjack. Well maintained 1 bedroom, 1 bath 3rd floor unit overlooking the canal. Make this your Florida Keys getaway or establish as a vacation rental. Rent nightly, weekly or monthly with proper licensing.. Skipjack Resort & Marina offers resort amenities - pool, tiki bar, tennis court, restaurant, trailer/rv parking & more. Boat launch on site. Desirable location. Sombrero Beach nearby. Walking distance to restaurants, grocery, drug stores, post office & more. Enjoy sunset views over Boot Key Harbor. Seller offering owner financing. LOW HOA Fee of $618+/- a month (collected quarterly). Easy to view. B&BATVAI

$464,000
Marathon
Island Club   - MM: 50.00
2 Bed, 2 Baths, 1,001 SqFt Days Listed: 26
-1.07% ($5,000) 1 Price Change : Last Change 2 Days Ago
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: First Come DockConcr

Waterfront condo for sale at Island Club, a 23 unit community located in the coveted Sombrero area in Marathon. 2 bedrooms, 2 baths, 1001 SF, split floor plan, with water views from the living room and primary suite. Beautifully updated kitchen that will inspire your inner chef and an ingenious pantry to hold all your extra items. Amenities include first come dockage, waterfront pool, tiki hut, community room with full kitchen, workshop and assigned parking for your convenience. There is also a community laundry but this condo has a washer and dryer in the unit. The primary suite includes an extra spacious walk in closet that every woman (or man) will love. The guest room has an ensuite for privacy and great storage. Island Club is within walking distance to the grocery store, shopping options and just 2 miles from beautiful Sombrero Beach. Dont miss this opportunity to make this condo your full time residence or 2nd home, so you can make every day feel like a vacation. Schedule a showing now and start living the waterfront lifestyle you deserve in the Florida Keys!

$469,900
Marathon
Key Colony Subdivision   - MM: 53.00
1 Bed, 1 Baths, 690 SqFt Days Listed: 272
-6.02% ($30,100) 3 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Fully remodeled 1/1 CBS home in the Florida Keys. Tile flooring throughout, SS appliances, washer/dryer, impact windows and doors, tankless water heater. Marathon allows rentals as little as 7 days. Fenced backyard with screened porch for privacy and entertainment, BBQ area and plenty of parking in front and on side of property with a pull through front and rear gate to facilitate boat and trailer parking. Close to shopping, restaurants and boat ramps. No Association. Come enjoy the Keys lifestyle!!

$475,000
Marathon
Lida Subdivision   - MM: 51.50
3 Bed, 3 Baths, 1,056 SqFt Days Listed: 408
-9.52% ($50,000) 2 Price Changes : Last Change 235 Days Ago
Mobile Home - Contingent - Waterfront No
Side of Island: Ocean - Dockage: None

Accepting backup offers!! Step into this wonderfully appointed, 3 bed, 2 bath home right in the middle of Marathon. This home is being offered fully furnished so you can move right in!Upon entry, youll find a spacious living area that flows into the dining room and well-appointed kitchen, providing a comfortable and functional living space. The three bedrooms offer ample sleeping space for everyone or the possibility of a dedicated home office. Beyond the main living space, adjacent to the kitchen, there is a convenient separate laundry area/mudroom that offers easy access to the beautifully landscaped yard thats just begging for lazy afternoons and BBQ nights. The spacious, covered patio provides an excellent space for hosting events or enjoying the peaceful surroundings. Additionally, a convenient shed offers ample storage options. The property is fenced on three sides, making it extremely private. There is plenty of space to park all your vehicles and toys. The house features central air and heat as well as a maintenance-free, metal roof.Marathon has that laid-back vibe youll love, and this home is right in the middle of it. Turn this spot into your own Keys paradise!

$477,000
Long Key
Outdoor Resorts   - MM: 65.60
2 Bed, 2 Baths, 420 SqFt Days Listed: 5
Mobile Home - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Own you piece of Paradise. Enclosed community with 24-hour Security. 2 bedrooms, 1 bathroom and very spacious with good size parking space to accommodate a boat. You own the land also. Amenities include: Clubhouse, Swimming pool for adults and a kiddie pool for the little ones. Marina, Mini store with gas for boats and vehicles, Tennis and basketball courts, Game Room, Library, Gym, boat trailer storage, Boat Ramp. A Fishermans dream with access to Gulf and Atlantic Ocean within five minutes by crossing the three mile Long Key Bridge. For more information or to view, contact Listing Agent.

$479,000
Key Colony
Cay Condo   - MM: 53.50
2 Bed, 2 Baths, 1,234 SqFt Days Listed: 79
-4.01% ($20,000) 1 Price Change : Last Change 21 Days Ago
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

Discover the charm of oceanfront living at an exceptional value in The Cay Condos, located in the heart of Key Colony Beach. Known for its small-town feel and pristine beaches, this walkable, bikeable island offers a host of amenities, including a par-3 golf course, marina, tennis and pickleball courts, and a variety of local restaurants. This 2-bedroom, 2-bath unit provides a welcoming retreat within a vibrant beachfront community. Residents enjoy a picturesque oceanfront courtyard with a pool, a beachfront tiki hut, a private sandy beach, party room and a community deck perfect for savoring breathtaking sunsets. With first-level living for easy accessibility and a calendar full of community events, this is your chance to embrace the best of Florida Keys living at an affordable price.

$489,000
Long Key
Outdoor Resorts   - MM: 65.60
1 Bed, 1 Baths, 778 SqFt Days Listed: 16
Mobile Home - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: Other Dockage

Fall in Love with this Little Gem in Outdoor Resort.Discover the charm of resort-style living in this lively gated waterfront community spanning 35 acres. This 2-bedroom, 1-bathroom property offers a plethora of amenities & endless charm. Ideal for both personal enjoyment and investment, its highly rented and sought after.Dont miss your chance to own a piece of paradise in this exclusive resort community. Contact us today to schedule a viewing!

$498,000
Marathon
Ocean Isles Fishing   - MM: 52.50
1 Bed, 1 Baths, 850 SqFt Days Listed: 33
Townhouse - Active - Waterfront Yes
Side of Island: Ocean - Dockage: First Come Dock,Boat

Discover your slice of paradise in this charming Marathon townhouse, perfectly positioned in the heart of the Florida Keys. This well-appointed 850-square-foot residence features one bedroom and two full bathrooms, offering an ideal layout for both permanent living and vacation rentals. This beautiful unit is being sold fully furnished and all appliances included. It features a great layout, new stainless-steel appliances, granite countertops and bathroom vanities, and is a wonderfully designed and decorated unit. The community stands out as a boaters dream, complete with dedicated boat docks and direct ocean access. Residents can embrace the authentic Keys lifestyle at the private tiki huts, perfect for socializing or simply unwinding while watching spectacular sunsets. The large community pool provides a refreshing retreat, surrounded by lush tropical landscaping that creates a serene atmosphere.Fishing enthusiasts will appreciate the immediate access to world-class fishing spots, while boating aficionados can easily navigate to either the Atlantic Ocean or Gulf of Mexico. The propertys location in Marathon Shores offers convenient proximity to local restaurants, shopping, and entertainment options.Weekly rentals are permitted, making this property an excellent investment opportunity with strong rental income potential. Whether youre seeking a vacation home, investment property, or permanent residence, this townhouse offers an authentic Keys living experience with all the modern conveniences you desire. Exceptional hands-off property management and vacation rental services can be continued by buyer if desired, to include a rolodex of potential repeat renters. Many who come to visit never want to leave, so buy now while the opportunity is available and enjoy a lifetime of relaxation, fun adventures, boating, fishing, and a great community.

$499,000
Marathon
Misc Key Colony Beach   - MM: 53.00
2 Bed, 2 Baths, 1,040 SqFt Days Listed: 60
-14.70% ($86,000) 2 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Step into the charm and character of Old Florida with this delightful 2-bedroom, 2-bath Keys cottage. Originally a duplex, this unique home has been thoughtfully combined by the owners to create a spacious and inviting single-family retreat. Nestled on an oversized lot, this property offers plenty of room to expand, garden, or simply enjoy the lush tropical surroundings.While the home retains its original charm, it presents a wonderful opportunity for personalization and updating to suit your style. Original Dade County pine ceilings and other unique Keys features.Enjoy the laid-back Keys lifestyle with ample outdoor space for entertaining or relaxing in the Tropics. Located in a quiet, established neighborhood, this property is just a short drive to local marinas, dining, and sandy beaches.Whether youre looking for a weekend getaway or a full-time island escape, this property offers the rare chance to own a piece of classic Florida Keys charm with room to grow. City of Marathon Market Rate Tranferable Building Right (TBR) is available with the property should buyer wish to purchase it.

$499,000
Marathon
Townhomes Of Sisters Creek   - MM: 48.50
3 Bed, 3 Baths, 1,512 SqFt Days Listed: 25
Townhouse - Active - Waterfront No
Side of Island: Ocean - Dockage: None

This spacious, detached pool-side townhome offers the perfect blend of comfort, convenience and coastal living within the secure confines of a gated, pet-friendly community. Covered parking leads to the ground-level foyer with ample storage space, transitioning to the elevated main living areas youll find a private balcony with pool views, laundry area, a convenient half bath and a versatile dining room. Nestled upstairs are the airy bedrooms, and access to the 2nd private balcony. Enjoy low-maintenance living in this well-kept community with affordable HOA fees of just $312/mo. With no transient rentals, its perfect for a full-time home, vacation retreat, or high-demand annual rental. And water access is just around the corner, with nearby public boat ramps and beautiful Sombrero Beach!

$499,000
Long Key
Outdoor Resorts   - MM: 65.60
2 Bed, 2 Baths, 700 SqFt Days Listed: 225
Mobile Home - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

AMAZING KEYS GETAWAY! Completely turn key home ready for you and your family to come make it your own. Community has it all! Basketball, Tennis, Pickeball, Marina, Gas Station, Private Beach, Pool, Banquet Hall, Sauna, Full Gym and Much more! Home is being sold fully furnished with almost everything you need including toys and a 6 seater golf cart! Parking on lot for up to 27 boat and 2 cars. Lots of storage and sleeps 10! Tiki Hut with TV, High Speed Internet, Combo Grill, beautiful turf, outdoor fridge and sink, outdoor shower. There is NOTHING MISSING! Just bring your flipflops and be ready to enjoy yourself!

$499,000
Marathon
Ocean Isles Fishing   - MM: 52.50
1 Bed, 1 Baths, 850 SqFt Days Listed: 76
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: First Come Dock,Boat

Discover the ultimate Florida Keys lifestyle in this 1-bedroom, 1.5-bathroom condo, located in the highly sought-after Ocean Isles Fishing Village. Set on seven acres of beautifully maintained, serene oceanfront grounds, this complex combines modern amenities with an unbeatable location right in the heart of the Keys.This concrete block construction condo offers a spacious two-story layout, ideal for a personal retreat or an income-generating property, with the flexibility of seven-day rentals.Ocean Isles provides a wealth of amenities, including a large oceanfront pool, a clubhouse, tiki huts, and fish cleaning stations for the avid angler. Boating enthusiasts will love the private boat ramp and first-come, deep-water dockage, offering easy access to the ocean. The newly updated marina features a seawall, bulkhead, and docks, ensuring smooth, protected boating for all your aquatic adventures.The central Marathon location makes this condo the perfect home base for exploring the Florida Keys, with world-class fishing, diving, and dining right at your fingertips.This is a rare opportunity to own a slice of paradise in one of the Keys most desirable communities. Schedule your private showing today!

$499,000
Marathon
Harbor Isle   - MM: 48.50
2 Bed, 2 Baths, 1,091 SqFt Days Listed: 23
Mobile Home - Contingent - Waterfront Yes
Side of Island: Ocean - Dockage: 50ft.

Excellent building opportunity in an unbeatable location with exceptional boating access! Situated right off Boot Key Harbor, this property offers a transferable building right and a 50 ft. concrete dock on crystal-clear, deep water canal, providing immediate access to both the ocean and the bay via the iconic Seven Mile Bridge. Boating enthusiasts will appreciate the convenience of nearby restaurants, bait, and fuel docks that the Harbor offers. Thanks to the TBR, construction of a beautiful new custom home could be underway rather quickly! Your investment opportunity awaits!

$499,900
Marathon
Little Venice   - MM: 53.00
2 Bed, 2 Baths, 875 SqFt Days Listed: 60
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Original Keys Conch House! BUILT TO LAST! They dont make them like this anymore! Just think of all the history this adorable conch home has but with all the modern conveniences of a remodeled property with granite counter tops, full backsplash in kitchen and high impact windows! Central location with easy walking distance to restaurants, churches and shopping. Easy installation of fencing and landscaping will make it your own private sanctuary and give space for the kiddos and pets to play. This is a versatile property that would work great for the first time home buyer, investor, work force housing or the snow bird who wants a sunny Keys getaway! Easy to assume flood policy, a breeze to show. Get into your new Keys home today! Ask me about the City grant or Home Town Heros program that helps buyers get into their forever homes!

$515,000
Marathon
Spanish Galleon   - MM: 50.00
2 Bed, 2 Baths, 1,056 SqFt Days Listed: 118
-6.36% ($34,999) 2 Price Changes : Last Change 3 Days Ago
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Assigned Dock,Other

This beautifully updated condo offers full views of Boot Key Harbor from the back and full views of a public golf course in the front. Have coffee enjoying the sunrise over the golf course and cocktails while viewing spectacular sunsets over the open harbor, as boats parade through the channel. Minutes to open water by boat, this complex offers available boat slips for up to 30 boats. Enjoy the pool while watching the harbor dolphins play or shop the many stores Marathon has to offer. This condo is minutes to grocery shopping, dining out and outdoor activities galore. Located minutes from the famous Sombrero Beach for a day in the sand and sun and full service marinas, boat ramps and all your fishing needs at your finger tips. This location is convenient to amenities, yet quite and tranquil for peaceful island life. This condo offers everything on your island wish list with a budget less than half the cost of a single family home. You get it all with the ease and convenience of condo living saving time and money on upkeep and repairs providing endless amounts of island living time. Go fishing, boating, swimming, golfing, and snorkeling instead of maintenance and yardwork. Make the most of island living and enjoy everything the Florida Keys has to offer. Your paradise is waiting! The City of Marathon is prime fishing, diving and dinning and only 45 minutes to the intrigue of historical Key West.

$515,000
Marathon
Sunset Bay   - MM: 56.00
2 Bed, 2 Baths, 874 SqFt Days Listed: 11
Half Duplex - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Quiet comfort and lush greenery surround you in this home. A brick paver driveway leads you to this 2 bed/1 bath remodeled beauty with granite counters, stainless appliances, updated bath, fenced back yard with a dip pool and deck. New roof in 2020, and new shutters in 2024. Walk one block to breathtaking sunsets at the neighborhood park, or hop on your bike and take a ride on the trail just up street. This is what island living is all about.

$518,000
Key Colony
Tall Ocean Beach   - MM: 53.50
1 Bed, 1 Baths, 675 SqFt Days Listed: 24
-2.08% ($11,000) 1 Price Change : Last Change 5 Days Ago
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

Step into a piece of 1960s Keys nostalgia with this sophisticated, charming one-bedroom, one-bath end unit condo. Located in a quaint boutique enclave of only 9 units, youll enjoy a serene and intimate atmosphere. This recently renovated home features an updated kitchen with 42 upper cabinets, quartz countertops, updated bathroom and plank vinyl flooring throughout. Enjoy unobstructed ocean views from the living room, kitchen, bedroom, and your balcony. Direct access to a private sandy beach makes it perfect for a tranquil weekend getaway, full-time residence or snowbird retreat. Modern comforts include an in-unit washer/dryer and jetted whirlpool tub, all wrapped in delightful Keys decor. Key Colony Beach offers everything and more for an ideal island life: a marina, golf course, pickleball, tennis, bocce, and basketball facilities, playgrounds, biking and walking paths, parks, a variety of restaurants, and a convenient post office. Experience the essence of the Florida Keys lifestyle with every visit.

$524,500
Key Colony
Sea Isle Condominium   - MM: 53.50
2 Bed, 2 Baths, 990 SqFt Days Listed: 48
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

Enjoy the convenience of having a private beach access steps away from your door! Come see for yourself why this property has been treasured by the family for over 45 years. Indulge in the beauty of the Florida Keys with this rare opportunity to own a pristine beachfront condo. This freshly painted ground level two-bedroom, two-bathroom haven offers breathtaking views of the Atlantic Ocean from every window. Sip your morning coffee enjoying the morning breeze on the balcony as the waves lap the shores and the sun rises above the horizon. With a private beach access at your feet, you can easily spend your days lounging on the white sandy beach, swimming in the crystal clear water, and soaking up the warm Keys sunshine. The condo itself is a turn-key vacation rental, fully furnished and bookings already in place. With similar oceanfront condos grossing over $75,000 in the past year with quite a few weeks of owner usage, this property has the potential to generate significant rental income. The spacious master bedroom boasts unparalleled views of the ocean, creating a peaceful and serene setting for relaxation. The property also includes a large heated pool, a tiki hut for shade, and a BBQ area for grilling up your catch of the day. Youll have everything you need for the ultimate beach vacation. This is your chance to own a piece of paradise in the coveted Key Colony Beach. Come see for yourself what makes this property special!

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.
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