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Islamorada Condos on the Bay / Gulf Side For Sale

Most of the properties in the Florida Keys peninsula are either on the bay / gulf side or on the ocean side of the island. The following Islamorada condos for sale below are on the gulf side / bay side.

Total Listings 13
Order By:

$589,000
Plantation Key
Executive Bay   - MM: 87.00
2 Bed, 2 Baths, 1,358 SqFt Days Listed: 191
-7.97% ($51,000) 1 Price Change : Last Change 28 Days Ago
Townhouse - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Dock Privileges,Boat

Welcome to Executive Bay Club in beautiful Islamorada, Florida Keys! Situated at mile marker 87 on the bayside, just north of Founders Park, this sought-after, pet friendly, community offers a range of top-notch amenities for a truly relaxing and convenient lifestyle. Enjoy access to a community pool, Tennis Courts, sandy bayfront beach, lush landscaping services, a manned front gate, 31 Boat slips for boats up to 28 ft available on a first come, first serve basis, 6 mooring pilings, fishing areas, fish cleaning tables, kayak launch, and much more!This inviting 2-bedroom, 1.5-bath unit, priced at $589,000, boasts updated bathrooms and kitchen, ensuring a modern and comfortable living space. The open and bright floor plan is complemented by back sliding doors that lead to a private patio, offering tree cover for shade and privacy. Perfectly located within the complex, this unit provides easy access to the community center, pool, and tennis courts.Executive Bay Club features 31 boat slips plus 6 mooring pilings, available on a first-come, first-serve basis. Additionally, residents can enjoy a kayak launch and a swim area off the beach. The community also benefits from an online voting system, allowing owners to participate in decision-making efficiently.Experience the best of Florida Keys living at Executive Bay Club - where every day feels like a vacation.

$599,000
Plantation Key
Executive Bay   - MM: 87.00
2 Bed, 2 Baths, 1,365 SqFt Days Listed: 292
-11.26% ($76,000) 4 Price Changes : Last Change 25 Days Ago
Townhouse - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Dock Privileges,Firs

No spiral stairs here! They have been replaced and its so much easier to walk up the stairs. This townhome is located by one of the tennis/pickleball courts and has a very nice open lanai with a cantilever umbrella to provide shade on those beautiful sunshiney Florida Keys days. The kitchen has stainless appliances and the washer and dryer are full size stackers. Both baths have been updated and the downstairs provides a second full bath. The on demand hot water heater guarantees that youll never run out of hot water. A new larger dock has been completed and provides for additional dockage. Other amenities include a large pool, 2 tennis/pickleball courts, community room, sandy beach, kayak and paddleboard storage. Come and enjoy the Executive Bay lifestyle! This townhome has been gently rented and had net rental income of $22,000 in 2023. Rentals began in 2022.

$599,000
Plantation Key
Executive Bay   - MM: 87.00
3 Bed, 3 Baths, 1,358 SqFt Days Listed: 45
Condo - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Dock Privileges,Othe

Discover the epitome of island living within Islamoradas gated community, Executive Bay Club. This meticulously maintained, updated two-story townhouse offers the perfect blend of comfort and convenience.Step inside to find a seamlessly remodeled kitchen with new appliances complemented by a spacious living area, and a full bathroom on the main floor. Whether youre entertaining guests or simply enjoying a quiet evening, the outdoor patio beckons for BBQ gatherings and tennis match viewings.Venture upstairs to find two generously sized bedrooms, each boasting walk-in closets for ample storage. A versatile and private loft space, cleverly separated from the primary bedroom, offers limitless possibilities - from a cozy third bedroom to a private office or storage area.With a generous 1,358 square feet of living space, this townhouse caters to full-time residents, part-time dwellers, or those seeking a lucrative vacation rental opportunity. Situated adjacent to Founders Park, residents enjoy unparalleled access to the finest amenities of the Florida Keys.For boating enthusiasts, first-come-first-serve dockage awaits, with additional slips now completed in the new marina! Now with 26 slips! Marina assessment has been paid by the seller! Now is a great time to buy in Executive Bay Club. Bask in breathtaking sunsets at the beach or take advantage of kayak storage onsite. Plus, with a pet-friendly policy allowing for two pets with no weight restrictions, every member of the family is welcome.Experience the ultimate in coastal living - schedule your private tour today! Easy to show. Dont miss this one! Seller financing possible!

$618,000
Plantation Key
Executive Bay   - MM: 87.00
2 Bed, 2 Baths, 1,355 SqFt Days Listed: 202
-8.98% ($61,000) 3 Price Changes : Last Change 2 Days Ago
Townhouse - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: Dock Privileges,Boat

Discover unparalleled coastal living in the heart of Islamorada, where this exceptional townhouse presents a rare blend of comfort and luxury. Tucked away in an exclusive community, this two-bedroom, two-bathroom townhouse with a loft stands out as the only unit with a private interior elevator, ensuring effortless access and convenience.Step inside to find a thoughtfully designed interior featuring a sunlit living area, a modern kitchen with updated appliances, and a dining space perfect for entertaining. The loft area offers additional flexibility, whether for a home office or extra sleeping quarters, complete with panoramic views of the surrounding tropical landscape.Outside, enjoy resort-style amenities just a short stroll away. Take advantage of a private marina with boat slips, a tranquil beach ideal for relaxation, and a sparkling pool for unwinding under the sun. Sports enthusiasts will appreciate the tennis courts and basketball hoop or kayaking/paddle boarding on the crystal clear bay, offering opportunities for outdoor recreation in a scenic setting.Conveniently situated within walking distance to the marina and a short drive from premier dining, shopping, and entertainment options, this townhouse embodies the essence of Florida Keys living. Whether youre seeking a serene retreat or an active lifestyle, Executive Bay Club provides the perfect balance of privacy and community. Call today for an appointment as this townhome will not last!

$700,000
Plantation Key
Executive Bay   - MM: 87.00
2 Bed, 2 Baths, 1,365 SqFt Days Listed: 17
Condo - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Dock Privileges,Firs

Executive Bay Club - Bayfront Paradise in the Florida KeysDiscover the perfect blend of comfort and coastal charm in this fully furnished and updated 2 (plus loft)-bedroom, 2.5-bathroom condominium type townhome in the sought-after Executive Bay Club nestled along the waters of the Florida Bay. This location offers breathtaking sunsets and an unbeatable Keys lifestyle and easy access to fishing and all water activities on the bay and ocean through Snake Creek only a short distance away. Step inside to find a thoughtfully remodeled kitchen with modern finishes, high end quartz counter tops, stainless appliances and all the storage you may need. Enjoy quiet time or family time or dinner time on your extra large patio / lanai overlooking lush outdoor green spaces. Centrally located on property so its quiet but close enough to all amenities. The interior living area has been updated with tile floors, new custom made wood and welded steel stairs, eliminating the spiral staircase for easier access and enhanced design. The community features exceptional amenities, including a heated pool, clubhouse, tiki huts, kayak storage, and tennis courts, security gate 24/7, an onsite manager and maintenance staff. Boating enthusiasts will appreciate the community dockage, while social butterflies can partake in numerous activities hosted in this vibrant neighborhood. Whether youre lounging by the bayfront, gathering with friends, or exploring the water, this property offers something for everyone.With endless opportunities to relax and entertain, plus the charm of the Florida Keys, this condo is a must-see. Schedule your private showing today and experience the Executive Bay Club lifestyle!

$765,000
Upper Matecumbe Key Islamorada
Sand Pebbles   - MM: 80.50
5 Bed, 5 Baths, 3,264 SqFt Days Listed: 375
-38.80% ($485,000) 6 Price Changes : Last Change 36 Days Ago
Condo - Contingent - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Significant price adjustment ... Owner looking for an offer on this on of a kind property in central Islamorada! Rare opportunity to own this detached Condominium/Home which sits apart and on its own providing a single family home and includes a 2 car garage/storage. Large and spacious two story concrete home offering 5 bedrooms & 3 baths, two living areas, over 3,200 square feet, partially remodeled in 2018, new kitchens, quartz counters, stainless steel appliances, tile floors, central AC, private walkway, porches, and privacy. Separate 2 car garage assigned to this condo. Located on the grounds of the Sand Pebbles Condominium, you will also enjoy the exceptional amenities including a Heated POOL, grand lawn, outdoor grilling area, walkway to watch the daily Sunsets, Bayfront observation deck, trailer storage, and pristine kept grounds. There is simply nothing else like this in Islamorada. Walk to Midway Cafe, Square Grouper, Safe Harbor Angler House Marina, Restaurants & Shops.

$769,000
Plantation Key
Executive Bay   - MM: 87.00
3 Bed, 3 Baths, 1,355 SqFt Days Listed: 24
Townhouse - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Dock Privileges,Firs

All NEW NEXT TO MARINA & POOL Stunning Islamorada 3/2 Townhouse with oversized loft features a new private community beach, marina and dock. Being sold fully furnished and fully equipped with high end appliances, high end furniture and furnishings. ALL NEW inside with new kitchen, new bar, new built-ins fishing cabinet and storage, 2 brand new Bathrooms with showers, new extended loft area, new full size Washer/Dryer, new BBQ area with new patio chicago brick pavers plus private patio shaded area with beautiful palms trees, serena & lily furniture inside, new electric panel, new electric water heater, new 80 smart OLED TV, new area just for refreshments, coffee and bar, new 4 ton AC unit, high end hurricane impact windows and doors that are reflective and cannot see inside. New Electric car charging electric panel exclusive to this unit. Best area in the community next to pool and marina with two pickleball courts and basketball court in the rear. Sleeps easily over 10 people. King bed in the master bedroom, 2 queen mattress in additional bedroom and loft along with 5 twin mattresses. Rented in winter for over $6k a month! Call today! See 3 Videos: https://youtu.be/P8cOME8P_kY; https://youtu.be/b6RmPMU8pvk; https://youtube.com/shorts/BEo0F_YzVFE;

$925,000
Plantation Key
Executive Bay   - MM: 87.00
2 Bed, 2 Baths, 1,359 SqFt Days Listed: 132
-7.41% ($74,000) 2 Price Changes : Last Change 2 Days Ago
Townhouse - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Dock Privileges,Boat

Enjoy the vibrant coastal lifestyle of Keys living in this desirable BAYFRONT townhome located in sought-after Executive Bay Club in Islamorada! This furnished townhome offers 2 bedrooms, 2 bathrooms plus a spacious loft, impact windows and doors, along with an open living layout that flows seamlessly through to the outdoor patio offering breathtaking sunsets and unobstructed Florida Bay views. Step out your back door to the sandy beach and dock with 31 boat slips available on a first-come, first-serve basis, for boats up to 28 at the dock or up to 35 tethered to one of the 6 mooring pilings. Perfectly located to enjoy offshore fishing in the Atlantic Ocean or backcountry fishing in the Florida Bay, as well as multiple dining spots nearby. The community offers a wealth of resort-style amenities, including a sparkling pool, clubhouse, two tennis/pickleball courts, a sandy beach, kayak and paddleboard storage and a pet-friendly environment. The dock and the walkway to the beach with new sand are recent upgrades. In addition, the pool, bathrooms and clubhouse are all being redone with assessments paid by seller. Secured with a manned/gated entrance. Located just minutes away from 5-star restaurants, breweries, and boutique shops, this townhome offers both luxury and convenience in this prime location.

$937,000
Plantation Key
Executive Bay   - MM: 87.00
2 Bed, 2 Baths, 1,403 SqFt Days Listed: 39
Condo - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: First Come Dock,Othe

Come live your best life - RIGHT ON THE BEACH! Enjoy SUNSETS, big views, DOCKAGE and the ideal Islamorada location. Boaters enjoy immediate BAY access and quick and easy OCEAN access via Snake Creek to the south and Tavernier Creek to the north. Youll be at all your favorite fishing, diving and dining spots in no time at all. Or - stay home and enjoy the beach right outside your door! Beautifully updated and lovely, this furnished bay front townhouse-style condo is directly on the beach and has TWO bedrooms PLUS a sleeping loft and THREE FULL bathrooms! Youll love having space to host your friends and family in the Keys. See every sunset from your own private balcony overlooking the beach and the bay. Enjoy sunsets and full bay views from almost every room. Bring your boat! First come dockage for boats up to 28 at the dock or up to 35 tethered to a piling. Trailer storage for up to three days. Impact windows and doors plus a metal roof add to the strength of the concrete building. Paddle boarding and kayaking is a breeze from this spot - and storage is no problem at all! This unit has a truly surprising amount of indoor and private outdoor storage. 11x14 locked storage area under the unit for all your water toys, plus additional space for your bikes and more gear is just outside the front door. Bring your furry friends! Two pets OK - no weight restriction. J4 has very easy access to the pool, clubhouse and tennis & pickle ball courts. Parking spaces are right outside your door. Founders Park is adjacent to Executive Bay Club with even more tennis, pickle ball, sandy beach, full service marina and more! Spiral stair case provides access to the second floor where youll find two full bedrooms and two full baths.... then it continues on up to the private sleeping loft. A third full bath is on the first level. Come find out why so many people love living on the beach at Executive bay Club.

$985,000
Lower Matecumbe
Bay Harbour   - MM: 75.00
2 Bed, 2 Baths, 1,473 SqFt Days Listed: 13
Condo - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Slip40ft.

Beautiful 2 bed, 2 bath condo Bay Harbour in Islamorada. This condo boasts a 40 boat slip. Bay Harbour allows 7-day rentals with a license from the Village. Enjoy the pool, hot tub, tennis & pickleball courts, and the many exciting local activities available in the Keys, including fishing charters, boating excursions, snorkeling, and diving adventures.

$1,225,000
Lower Matecumbe
Bay Harbour   - MM: 75.00
3 Bed, 3 Baths, 2,026 SqFt Days Listed: 298
-3.92% ($50,000) 1 Price Change : Last Change 176 Days Ago
Condo - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Slip30ft.

Bay Harbour condos, located at MM 74.5 on Lower Matecumbe is a very desirable community. BAY HARBOUR ALLOWS 7-DAY RENTALS. Transient Rental License can be obtained from the Village of Islamorada that allows weekly rentals which are restricted in most communities in Islamorada and indeed all of Monroe County. This 2,000 sq. ft three-bedroom, two and a half bathrooms has a view of the sunrise on the Atlantic Ocean. A 30 boat slip is included which allows quick access to Florida Bay and a short ride will bring you to the ocean through channel 2 or channel 5. This gated community boasts a fantastic pool and hot tub along with a gym, clubhouse and tennis courts. Landscaping and maintenance of the property is professionally directed by the on-site property manager. This unit is equipped with propane gas range. Floor plan dimensions in photos are very close estimates. Buyer to verify.

$1,225,000
Lower Matecumbe
Bay Harbour   - MM: 75.00
3 Bed, 3 Baths, 2,026 SqFt Days Listed: 68
Condo - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Boat Slip3

Ideal location in the desirable Bay Harbour community. Convenient access to Florida Bay and the Atlantic Ocean. Community amenities include a pool, hot tub, gym, and clubhouse. Perfect for year-round living or as a vacation rental as Bay Harbour allows 7-day rentals with a Village Vacation Rental License. This condo has a 16,000# boat lift in the designated boat slip.

$2,950,000
Upper Matecumbe Key Islamorada
Bay Colony Villas   - MM: 81.50
4 Bed, 4 Baths, 2,072 SqFt Days Listed: 5
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: First Come Dock150ft

Only sophistication and class represented in Islamoradas most exclusive development, Tarpon Flats. This rare offering has underwent a full high-end renovation to satisfy the most distinguished buyer. The elegant paver driveway leads up to pristine grounds showing off its manicured landscaping. One of only 12 luxury bayfront homes on a sprawling four-acre parcel. The property exudes a unique charm blending Old Florida allure with the timeless essence of Nantucket. Covered parking and a versatile multi-purpose room on the ground floor with a foyer entry. On the second floor you will find an open living space with the kitchen & dining room overlooking the bay, 2 bedrooms/2 bathrooms, and serene positioning for nightly sunsets. The third floor is dedicated to the master suite and maids quarters with more amazing views from the private balcony. If amenities are what youre after, Tarpon Flats delivers on all fronts: a beautiful tennis court with covered seating for spectators, a rare greenhouse to nurture your beloved plants, a waterfront pool & gazebo leading down to the beachfront, and plenty of dockage for your skiff. Come see the exclusivity of Tarpon Flats for yourself.

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 02-02-2025.
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