Divider
Content Divider

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:

$599,000
Plantation Key
Executive Bay   - MM: 87.00
2 Bed, 2 Baths, 1,345 SqFt Days Listed: 25
Townhouse - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: Dock Privileges,Firs

Be ready to be captivated by this stunning townhome in the sought-after Executive Bay Club! The home features 2 beds, 3 baths, a spacious kitchen, an open floor plan, outdoor living space, and an additional loft area. Entertain guests on the backyard patio while savoring delightful afternoons. The community offers numerous perks, including a gated entrance with 24-hour security, a pool, clubhouse, tennis courts, and an array of amenities. Located in the heart of Islamorada, youll have convenient access to top-notch restaurants, shopping, and the renowned Founders Park. (Owner / Agent)

$635,000
Plantation Key
Executive Bay   - MM: 87.00
2 Bed, 2 Baths, 1,365 SqFt Days Listed: 226
-5.93% ($40,000) 3 Price Changes : Last Change 39 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.

$640,000
Plantation Key
Executive Bay   - MM: 87.00
2 Bed, 2 Baths, 1,358 SqFt Days Listed: 125
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 $640,000, 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.

$650,000
Plantation Key
Executive Bay   - MM: 87.00
2 Bed, 2 Baths, 1,357 SqFt Days Listed: 55
Condo - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Dock Privileges,Boat

Experience the ultimate Florida Keys lifestyle in this spacious 2-bedroom, 3-bath condo located in the highly sought-after, gated Executive Bay Club. With manned security for added peace of mind, this unit offers a versatile sleeping loft and a cozy office/sleeping nook, providing ample space for family and guests.The bright kitchen boasts granite countertops, stainless steel appliances, beverage bar with wine cooler and a tankless hot water system. The master bedroom features its own private bathroom, while both bedrooms include plantation shutters for added privacy and style. You will enjoy this units close location to the pool and sandy beach, as well as easy access to community amenities like the clubhouse, dockage, pickle ball, tennis and basketball courts--all just steps away from Founders Park, where local festivals and events take place throughout the year. Pet owners will appreciate that the community allows 2 approved pets, making it a perfect fit for animal lovers. Dont miss this fantastic opportunity--ask about the rental income potential!

$664,900
Plantation Key
Executive Bay   - MM: 87.00
2 Bed, 2 Baths, 1,355 SqFt Days Listed: 136
-2.08% ($14,100) 1 Price Change : Last Change 27 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!

$785,000
Plantation Key
Executive Bay   - MM: 87.00
2 Bed, 2 Baths, 1,355 SqFt Days Listed: 149
-21.11% ($210,000) 4 Price Changes : Last Change 2 Days Ago
Townhouse - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: First Come Dock

Stunning Islamorada 3/2 plus loft with new private community beach, marina and dock. Being sold fully furnished and fully equipped with high end furnishings. All new inside with new kitchen, new bar, new built-ins fishing cabinets and storage, 2 brand new Bathrooms with showers, new extended loft area, new high end appliances, new full size Washer/Dryer, new BBQ area with new patio pavers and private palms trees, serena & lily furniture, 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. Sleeps easily over 10 people. King 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!

$795,000
Upper Matecumbe Key Islamorada
Sand Pebbles   - MM: 80.50
5 Bed, 5 Baths, 3,264 SqFt Days Listed: 309
-36.40% ($455,000) 5 Price Changes : Last Change 4 Days Ago
Condo - Active - 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.

$925,000
Lower Matecumbe
Sandy Point   - MM: 74.50
2 Bed, 2 Baths, 1,206 SqFt Days Listed: 14
Condo - Contingent - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Dock Privileges,Firs

Spectacular sunsets and a tropical beach vibe await you at this rarely offered Sandy Point Condo! Upon entering on the ground level ascend the open stairway to the main living level offering dining area, custom galley kitchen with large pantry, half bath, and living room with large windows looking out over the glistening waters of Florida Bay. Awaken to beautiful bay views from the second level primary bedroom. Your friends and family members will be comfortable in the guest bedroom with peek-a-boo beach and bay views. A full bath separates the bedrooms, and there is also a good size storage closet at the top of the stairs. Your personal laundry is located on the ground level enclosed within the covered parking area which will accommodate two vehicles. Additional storage for all your boating and fishing toys is also on the ground level. New impact windows and door were recently installed (April 2024), and a newer 3.5 ton 16 SEER Lennox AC system installed in 2021. Concrete dockage with fish cleaning table is available to you for up to a 30 foot vessel. The most sought after fishing waters are within a close cast away, and access to the Atlantic Ocean from the bay is nearby through Channels Two and Five bridges. After a day on the water enjoy a stroll down your private beach and wade into the shallow, sandy bottom bay for a swim, or sit under the tiki hut and enjoy a cool beverage while watching the sun set on another day in paradise. Whether you are searching for a fulltime Islamorada home, or a weekend getaway, Sandy Point is the perfect place for you!

$950,000
Plantation Key
Executive Bay   - MM: 87.00
2 Bed, 2 Baths, 1,359 SqFt Days Listed: 66
-4.90% ($49,000) 1 Price Change : 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! Boasting 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, along with 6 mooring pilings. Perfectly located to enjoy offshore fishing in the Atlantic Ocean or backcountry fishing in the Florida Bay. 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. 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.

$950,000
Plantation Key
Executive Bay   - MM: 87.00
3 Bed, 3 Baths, 1,500 SqFt Days Listed: 154
-4.52% ($45,000) 1 Price Change : Last Change 2 Days Ago
Condo - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Dock Privileges,Firs

Experience the magic of breathtaking sunsets every evening from the comfort of your own backyard! This stunning townhome-style end unit offers an unparalleled living experience, enhanced by its meticulous remodeling and prime location offering a luxurious retreat with 2 bedrooms, an AC finished loft area, and 3 full baths. As you step inside, youre greeted by a bright and airy open living floor plan adorned with tile flooring that leads seamlessly to your back patio, just steps away from the beach and docking area. The custom kitchen, boasting plenty of space, all wood cabinetry, granite countertops, and stainless steel Whirlpool appliances--perfect for entertaining guests and creating culinary delights. Relax and unwind in the primary bedroom with its en suite full bathroom, offering a private sanctuary within your home. Added conveniences include a front load washer and dryer for your laundry needs. Exciting news--theres a new marina/dockage is completed. The HOA at Executive Bay Club, a private gated community located next to Founders Park, allows for 2 domestic pets of any size. Enjoy a host of amenities including a heated/chilled pool, clubhouse, sandy beach area, dock privileges, tennis courts/pickleball, basketball, and more! This is a must-see property that promises a lifestyle of luxury and leisure in a prime location. Dont miss out on the opportunity to make this your dream home!

$999,998
Lower Matecumbe
Bay Harbour   - MM: 75.00
2 Bed, 2 Baths, 1,473 SqFt Days Listed: 206
Condo - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: None

Experience the pinnacle of Florida Keys living with this stunning 2-bedroom, 2.5-bathroom condominium in the Bay Harbour complex. Located in the heart of Islamorada, unit 102 is beautifully appointed with high-end finishes and offers breathtaking views of the water and marina. Key Features Include: Spacious Living: Spanning a generous floor plan, this unit features two sizable bedrooms, each complemented by its own ensuite, and a guest half bathroom for optimal convenience.Luxurious Appointments: Each room is meticulously designed with luxury and comfort in mind, featuring modern decor and top-of-the-line amenities.Stunning Views: From the private screened balcony, enjoy fabulous, views of the sparkling water of Captains Cove and the Atlantic Ocean across the way, providing a serene backdrop to your daily living.Prime Location: Situated within a sought-after community that offers a wealth of amenities including a pool, spa, tennis and pickleball courts, community room, gym, covered parking, guest parking, and direct access to boating facilities.Investment Potential: With the allowance for weekly rentals, this property presents a valuable investment opportunity, perfect for generating rental income.Lifestyle & Convenience:Bay Harbor Condominiums not only offer luxurious living but also a lifestyle of ease and entertainment. Whether youre indulging in the on-site amenities or exploring the local attractions of Islamorada, life here is sure to be exceptional.Invest in Your Dream:Whether as a permanent residence or a lucrative investment property, unit 102 at Bay Harbor is an excellent choice for discerning buyers seeking luxury, location, and lifestyle in the Florida Keys. Come live where others vacation in the fabulous Florida Keys!

$1,225,000
Lower Matecumbe
Bay Harbour   - MM: 75.00
3 Bed, 3 Baths, 2,026 SqFt Days Listed: 232
-3.92% ($50,000) 1 Price Change : Last Change 93 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: 2
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.

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 11-28-2024.
Back To TopMore Info
Terms / Privacy / Accessibility ADA