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Islamorada Condos for Sale - Condominiums, Florida Keys Real Estate

See all MLS listings of condos for sale in Islamorada below.  This popular Florida Keys real estate market includes not only affordable Islamorada condos, but a range of luxury waterfront condominiums as well, with a variety of options in great condo communities like Bay Harbour and Beacon Reef.  The market includes condos in Upper Matecumbe, Lower Matecumbe, Windley Key, and Plantation Key.  Many condominiums in Islamorada offer top amenities including resort-style swimming pools, boat dockage and more. 

Total Listings 45
Order By:

$249,000
Lower Matecumbe
Mat Ocean View   - MM: 76.50
1 Bed, 1 Baths, 518 SqFt Days Listed: 54
Condo - Active - Waterfront No
Side of Island: Ocean - Dockage: n/a

This is a terrific opportunity to purchase a renovated 1Bd/ 1Ba Condo in Islamorada with all the boating, fishing, and diving amenities available. Unit is renovated and if you like the color purple you will love this unit!. Includes hurricane shutters and one car garage. Maintenance Fees are $1,275.00 per Quarter.Features include dockage, boat storage, boat ramp, heated pool & clubhouse, tennis court, chickee hut and BBQ area. The only units in the area with a garage. On site property caretaker, Building Insurance and standard cable are included in the condo fee. Rentals are allowed.

$285,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
1 Bed, 1 Baths, 358 SqFt Days Listed: 139
-13.64% ($45,000) 3 Price Changes : Last Change 24 Days Ago
Condotel - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Dock Privileges

Located in the heart of downtown Islamorada, Cheeca Lodge & Spa. Be a part of a world-class resort, without the worries!! 27 acres of tropical landscaping, 9-hole golf course, pickle ball, tennis courts, 3 heated pools, full array of water sports, fishing pier, private fishing and boat trips, fine and casual dining, 2 tiki bars, concierge, shopping, camp Cheeca for the kids, Lovely spa and fitness facility! MOTIVATED SELLERS! Passive Investment Income producing property allowing owner to occupy unit for 28 days yearly!

$315,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
1 Bed, 1 Baths, 380 SqFt Days Listed: 376
Condotel - Active - Waterfront No
Side of Island: Ocean - Dockage: Dock Privileges

Welcome to your double queen corner resort room at the historic Cheeca Lodge & Spa. This rare top floor unit features extra high ceilings, two queenbeds, one luxurious bathroom with soaking tub and separate shower. Income producing property allowing 28 fabulous owner days! Cheeca handles all vacation rentals making your investment hassle free. The resort offers a spa, Camp Cheeca for the kids, beachfront pool, 9-hole par 3 golf course, lush gardens, bike path, tennis courts, pickle ball court, fitness center, 5 star dining, tiki bar, beach, dock, water sports, and fishing. COMBINE with UNIT 730 for TOTAL PRICE of $645,000! Cheeca is located in the heart of Islamorada and in walking distanced to shopping, galleries, restaurants, breweries, and island festivities.

$325,000
Plantation Key
Sea Gulls   - MM: 90.00
1 Bed, 1 Baths, 756 SqFt Days Listed: 104
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

Enjoy you own piece of paradise nestled in the quiet and private neighborhood of Sea Gulls Condominiums. This unit offers TOP FLOOR, expansive views of the ocean and neighboring harbor. Waterviews on both sides! Stunning sunrise views greet you each morning in this well maintained 1 bed/1 bath condo. Updated kitchen and bathroom. First floor amenities are currently under construction and will include a weight room, yoga studio, clubhouse and enhanced swimming pool and deck. Put in your kayak or paddle board on the gorgeous sandy beach. Excellent location near restaurants, parks, shopping and much more! 1.5 hrs to MIA airport and 2 hrs to Key West. Make sure to check out the aerial video under the photos tab!

$339,000
Plantation Key
Executive Bay   - MM: 87.20
2 Bed, 2 Baths, 1,356 SqFt Days Listed: 45
Townhouse - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: First Come Dock

Excellent Islamorada location and now pet friendly! End-unit townhouse in popular Executive Bay Club with two bedrooms and two FULL bathrooms. Nightly sunsets from the beach - plus dockage, clubhouse, pool and tennis. Peek-a-boo ocean views from the living room and master bedroom, washer and dryer right in the unit. Both bedrooms are freshly painted and the huge master has a large loft which makes a third sleeping area or mini office. Grill and chill on the back patio. Complex is next door to Islamoradas gem - Founders Park with a full service marina, trails, tennis, huge pool complex and so much more. Leave the car at home and walk to events like the Nautical Flea Market and Island Fest. Executive Bay Club is just down the road from Plantation Key School, close to restaurants/shopping

$339,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
1 Bed, 1 Baths, 358 SqFt Days Listed: 464
Condotel - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

Here is your chance to own a great, income-producing piece of the iconic Cheeca Lodge & Spa in the heart of Islamorada. This beautiful double queen bedded resort view room is a great investment and can be your vacation spot for up to 28 days per year! Cheeca has long been the resort of choice for families, romantic getaways and more than one President. You will have your choice of 3 great restaurants, 2 bars, 2 pools (with a 3rd coming soon), 6 lighted tennis courts, a 9-hole, par 3 golf course, a Spa and workout facility, along with Camp Cheeca for kids. This unit has experienced over 80% occupancy and offers a great return on investment.

$355,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 81.80
1 Bed, 1 Baths, 550 SqFt Days Listed: 376
Condotel - Active - Waterfront No
Side of Island: Ocean - Dockage: Dock Privileges

Welcome to your King Suite at the historic Cheeca Lodge & Spa. This rare top floor unit features extra high ceilings, one bedroom, one bathroom, and a full kitchen. Income producing property allowing 28 fabulous owner days! Cheeca handles all vacation rentals making your investment hassle free. The resort offers a spa, Camp Cheeca for the kids, beachfront pool, 9-hole par 3 golf course, lush gardens, bike path, tennis courts, pickle ball court, fitness center, 5 star dining, tiki bar, beach, dock, water sports, and fishing. Sleeper sofa in living area for additional sleeping. COMBINE with UNIT 731 for TOTAL PRICE of $645,000! Cheeca is located in the heart of Islamorada and in walking distance to shopping, galleries, restaurants, breweries, and island festivities.

$389,000
Plantation Key
Executive Bay   - MM: 87.00
2 Bed, 2 Baths, 1,351 SqFt Days Listed: 17
Townhouse - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: First Come Dock

Beautiful Executive Bay Club! This spacious updated end unit townhouse is located across from the pool and steps away from the bayfront and dock. Offering 2 bedrooms & 2 bathrooms with a loft and over 1,350 square feet of living space with impact windows and a beautiful back yard patio. This bayfront complex is located in Islamorada featuring a gated entrance, pool, tennis courts, first come first serve dockage, beach, club house and 2 pets are allowed. Founders Park is next door offering many activities including the famous Nautical flee market. Dont miss this outstanding opportunity to live in Paradise!

$395,000
Plantation Key
Sea Gulls   - MM: 90.00
2 Bed, 2 Baths, 1,179 SqFt Days Listed: 134
-7.93% ($34,000) 1 Price Change : Last Change 79 Days Ago
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

Escape to your Islamorada condo with Endless Ocean Front Breezes and Views ! This 5th Floor Unit offers 2 Spacious Bedrooms, 2 Full Bathrooms, Updated Kitchen and Bathrooms, and a Over-Sized Screened in Porch Accessible from the Living Room and Both Bedrooms. Master Bedroom has a Fantastic Built-In TV and Shelving Unit, Dual Sink Vanity, and Walk-In Closet.Sea Gulls Condominium Complex Features a Oceanside Relaxing Pool, Multiple Tiki Huts, and a Beautiful Sandy Beach ideal for Kayaking and Paddle Boarding. Perfect Location, Private yet Close to Everything! Whether youre looking for the Keys Life or a Weekend Getaway this one will not Disappoint!

$415,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 81.80
1 Bed, 1 Baths, 550 SqFt Days Listed: 52
Condotel - Active - Waterfront No
Side of Island: Ocean - Dockage: Dock Privileges

HISTORIC CHEECA LODGE & SPA located in the heart of Islamorada! Exceptional income producing property with onsite rental management. This King Suite features a beautiful one bedroom, one bath and a full kitchen. You will enjoy the outstanding amenities including 5-star dining, spa, pools, beach, tiki bar, dock, 9-hole par 3 golf course, tennis courts, fitness center, water sports and lush tropical gardens throughout. Cheeca Lodge is located within walking distance to outstanding restaurants, galleries, breweries, shopping and Islamoradas famous art district.

$425,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
1 Bed, 1 Baths, 361 SqFt Days Listed: 568
+6.25% ($25,000) 1 Price Change : Last Change 358 Days Ago
Condotel - Active - Waterfront No
Side of Island: Ocean - Dockage: Dock Privileges

Cheeca Lodge & Spa double queen suite. The perfect way to get yourself into the Keys; excellent rental income, turn key-opportunity. Enjoy 5 star dining, beach, spa, pools, 9-hole par 3 golf course, Camp Cheeca for the kids, and so much more! Cheeca Lodge is located Oceanside in the heart of Islamorada and walking distance to Islamoradas famous art district, fine dining and shopping.

$425,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
1 Bed, 1 Baths, 550 SqFt Days Listed: 568
+6.25% ($25,000) 1 Price Change : Last Change 358 Days Ago
Condotel - Active - Waterfront No
Side of Island: Ocean - Dockage: Dock Privileges

Cheeca Lodge & Spa king suite with lagoon view! The perfect way to get yourself into the Keys; excellent rental income, turn key-opportunity. Enjoy 5 star dining, beach, spa, pools, 9-hole par 3 golf course, Camp Cheeca for the kids, and so much more! Cheeca Lodge is located Oceanside in the heart of Islamorada and walking distance to Islamoradas famous art district, fine dining and shopping.

$425,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
1 Bed, 1 Baths, SqFt Days Listed: 568
+6.25% ($25,000) 1 Price Change : Last Change 358 Days Ago
Condotel - Active - Waterfront No
Side of Island: Ocean - Dockage: Dock Privileges

Cheeca Lodge & Spa lagoon view king suite. The perfect way to get yourself into the Keys; excellent rental income, turn key-opportunity. Enjoy 5 star dining, beach, spa, pools, 9-hole par 3 golf course, Camp Cheeca for the kids, and so much more! Cheeca Lodge is located Oceanside in the heart of Islamorada and walking distance to Islamoradas famous art district, fine dining and shopping.

$445,000
Plantation Key
Executive Bay   - MM: 87.00
2 Bed, 2 Baths, 1,362 SqFt Days Listed: 26
Townhouse - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: Assigned Dock,Dock P

Great location, gated community, community dockage, beach, club house, pool, tennis courts, manager on site in the heart of the Village of Islamorada next door to Islamoradas Founders Park are the ingredients for a fantastic Florida Keys getaway, seasonal vacation home or full time residence. We are talking about the Executive Bay Club. 2 bedrooms with a loft for 3rd. Most everything one comes to the Florida Keys for in a nice residential atmosphere close to shopping, entertainment, restaurants, fish and dive charters, marinas, hospital and dont forget about the sunsets! Call today for an appointment to see G6 Executive Bay! Across the drive literally to the pool and clubhouse, just steps away from the bay front beach and docks. Come experience what Executive Bay has to offer today

$449,000
Plantation Key
Plantation By The Sea   - MM: 87.50
2 Bed, 2 Baths, 981 SqFt Days Listed: 282
-18.36% ($101,000) 5 Price Changes : Last Change 74 Days Ago
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Other Dockage

Are you looking for open oceanfront views? Then this is for you! Beautifully updated townhouse style condo with fabulous ocean views and in unit washer and dryer. The kitchen island has room for prepping AND entertaining while enjoying ocean views. The open floor plan allows you to see the ocean from the front door through the living space and to the veranda. Upgraded with impact windows and sliding glass doors this townhome is ready for a new family to enjoy Keys living at its finest. Additional features include travertine floors, Stainless Steel appliances, granite countertops, custom lighting fixtures and crown molding. This unit also has an assigned covered parking space.

$465,000
Upper Matecumbe Key Islamorada
Palms Of Isla   - MM: 80.00
2 Bed, 2 Baths, 1,053 SqFt Days Listed: 184
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

Islamoradas best kept secret, The Palms. This light and bright two bedroom and two bathroom condo has an oceanfront covered balcony and views for days! The Palms has terrific amenities such as an oceanfront pool, large hot tub, tiki bar, grill area, indoor gym facility, and a concrete walkway that will directly take you into the ocean. In a gated and secure complex, this unit has an assigned covered parking spot. Ideally located within walking distance to marinas and restaurants, this opportunity is waiting for you!

$575,000
Lower Matecumbe
Islamorada South   - MM: 76.50
2 Bed, 2 Baths, 1,079 SqFt Days Listed: 101
Condo - Active - Waterfront No
Side of Island: Ocean - Dockage: Boat Ramp,Dock Privi

Splendor of Islamorada South - no remodeling necessary. This 2 bedroom 2 1/2 bath unit has been completely remodeled. The expanded custom kitchen with wood cabinets and granite countertops opens to the living room and screened porch. Guest bedroom and bath round out the first level. Head up the stairs to your private master suite with screened balcony. Spacious garage perfect for storing your weekend toys. Large carport is ideal for covered outdoor entertaining. Bring your boat! There is always space on the dock for your 25 boat. Clean your catch dockside on the cleaning table. Secured boat and trailer storage is available. It is just a short jaunt to the ocean or the bay. For an intimate complex, the amenities are grand.

$645,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 81.80
2 Bed, 2 Baths, 908 SqFt Days Listed: 398
Condotel - Active - Waterfront No
Side of Island: Ocean - Dockage: Dock Privileges

Welcome to your double unit corner suite at the historic Cheeca Lodge & Spa. This rare top floor unit features extra high ceilings, two bedrooms, two bathrooms, and a full kitchen. Income producing property allowing 28 fabulous owner days! Cheeca handles all vacation rentals making your investment hassle free. The resort offers a spa, Camp Cheeca for the kids, beachfront pool, 9-hole par 3 golf course, lush gardens, bike path, tennis courts, pickle ball court, fitness center, 5 star dining, tiki bar, beach, dock, water sports, and fishing. Sleeper sofa in living area for additional sleeping. Cheeca is located in the heart of Islamorada and in walking distanced to shopping, galleries, restaurants, breweries, and island festivities.

$669,000
Lower Matecumbe
Las Maravillas   - MM: 75.70
2 Bed, 2 Baths, 1,104 SqFt Days Listed: 90
Townhouse - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: First Come Dock

Rare opportuniuty to own the end unit closest to the bay, pool and dock at at Las Maravillas Townhouses on Lower Matecumbe in the Village of Islamorada. 2 spacious bedrooms with Jack and Jill Bathroom on top floor along with laundry. Main level has living room, dining area and full kitchen. Four balconies, covered parking for boat or two or more cars on ground level with spacious storage closet. Las Maravillas is an intimate enclave of 10 contiguous townhouses in a gated tropical setting with bay front location and shared dockage for its residents. Come see Las Maravillas for yourself today!

$699,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
2 Bed, 2 Baths, 908 SqFt Days Listed: 184
-7.91% ($60,000) 2 Price Changes : Last Change 11 Days Ago
Condotel - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Dock Privileges

Come to the World Famous Cheeca Lodge & Spa Resort. Featuring Premier Income Producing Unit , approximately 50k a year. Only One of four Luxurious 2/2 available. Cheeca handles all vacation rentals making your investment hassle free. 28 exquisite and exclusive days for owners use. On 27acres with tropical landscaping. Enjoy 5 star dining, beach, spa & fitness, 3 heated pools, fishing pier, tennis & pickleball, & a 9-hole par 3 golf course. Private fishing excursions & Plenty of watersports. Camp Cheeca for the kids, and so much more! Paradise Awaits You!

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 10-31-2020.

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