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Islamorada Homes 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 homes for sale below are on the gulf side / bay side.

Total Listings 56
Order By:

$475,000
Lower Matecumbe
White Marlin Beach   - MM: 74.50
5 Bed, 5 Baths, 2,900 SqFt Days Listed: 53
Fractional Ow - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 55ft.Cut/Natural

New co-ownership opportunity: Own one-eighth of this professionally managed, turnkey home by Pacaso. Tucked within the coveted White Marlin Beach enclave, this canal-front retreat captures the essence of refined Florida Keys living. Framed by swaying palms and a gracious front entry, the 5-bedroom, 3.5-bathroom residence offers a seamless blend of comfort and coastal elegance.The open-concept main level is bathed in natural light, with soaring ceilings, oversized windows, and glass doors that connect the living area to the private pool and tranquil canal beyond. A bright, gourmet kitchen anchors the space with JennAir appliances, dual sinks, and generous cabinetry--ideal for effortless entertaining. A bay window in the dining area frames serene views of the pool.The main-floor primary suite features a custom walk-in closet and direct access to the patio and pool. Upstairs, a second spacious bedroom offers a large closet and a Jack-and-Jill bath shared with an adjoining guest room. Two additional bedrooms provide ample accommodations for family and guests. The home comes fully furnished and professionally decorated.

$650,000
Upper Matecumbe Key Islamorada
Coral View   - MM: 81.00
3 Bed, 3 Baths, 2,016 SqFt Days Listed: 249
-31.58% ($300,000) 7 Price Changes : Last Change 13 Days Ago
Single Family - Contingent - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

This lovely home is classic Keys on the outside, with modern elegance on the inside. Secluded on high ground in the heart of downtown Islamorada, this accommodating three-bedroom, two-bath residence offers abundant space for relaxation and entertainment, including an inviting back porch, surrounded by lush landscaping that enhances the serene atmosphere. The expansive front and back yards provide ample room for outdoor activities and gatherings. Ideally situated, you are within easy walking distance to the beaches, great restaurants, and grocery shopping. Experience the perfect blend of comfort and convenience in this idyllic retreat.

$1,075,000
Lower Matecumbe
White Marlin Beach   - MM: 74.50
3 Bed, 3 Baths, 1,888 SqFt Days Listed: 56
PreConstructi - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

Your tropical dream awaits with the lowest-priced waterfront lot featuring an active building permit in Islamorada. Imagine waking up to sunlit mornings, salty breezes, and the soft embrace of warm sand beneath your feet. Welcome to White Marlin Beach, where your vision of paradise comes to life.Vacant lots with active building permits are a rare find, and this one is ready for you to create your dream retreat. Picture a three-bedroom, four-bathroom island escape blending coastal charm with modern luxury. Two spacious, sunlit stories are designed for relaxation, complete with an elevator to ensure comfort and convenience. Expansive porches invite you to unwind, sip your morning coffee with bay views, feel the ocean breeze in your hair, and enjoy evenings under a canopy of stars. New construction offers more than a fresh start--it brings favorable insurance rates, a solid foundation, and the confidence of quality craftsmanship.This is your gateway to maritime bliss. The private homeowners park features one of the few sandy beaches in the Keys, perfect for building sandcastles, watching sunsets, and creating cherished memories.This property offers convenient access to vibrant dining, boutique shopping, and an inspiring arts scene. Its more than just a property; its an invitation to embrace the island lifestyle.Opportunities like this dont wait. Ready to turn your dream into reality? Dive into your future at White Marlin Beach--your tropical oasis is calling!

$1,100,000
Plantation Key
Bay Ridge   - MM: 87.50
3 Bed, 3 Baths, 1,682 SqFt Days Listed: 280
-4.26% ($49,000) 1 Price Change : Last Change 112 Days Ago
Single Family - Contingent - Waterfront No
Side of Island: Bay/Gulf - Dockage: Dock Privileges,Othe

Welcome to your charming ground-level concrete home nestled in the highly sought-after Bay Ridge subdivision in Islamorada! This property, situated on a corner lot, boasts a prime location within the coveted X flood zone. Step into this spacious abode offering 3 bedrooms, 2 bathrooms, and bonus room with a built-in bar, ideal for accommodating family gatherings and entertaining guests. The layout provides ample flexibility to tailor the space to your unique lifestyle preferences. Outside, you will enjoy the spacious corner lot offering mature landscaping and lush green lawn along with a brick-paved circular driveway. Immerse yourself in the incredible community amenities, including a beautiful marina, inviting pool, and convenient boat ramp, perfect for enjoying the lifestyle at your leisure. For outdoor enthusiasts, nearby Founders Park offers a sandy beach, olympic-size pool, boat ramp, ball fields, tennis/pickleball courts, and a dedicated dog park. Whether you choose to enjoy the property in its current state or embark on a journey of customization to fulfill your vision, the options are boundless.

$1,125,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
3 Bed, 3 Baths, 2,808 SqFt Days Listed: 27
-2.17% ($25,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: Dock Privileges

MOTIVATED SELLERS! Paradise Found: Renovated Jungle Treehouse in Islamorada. This fully renovated CBS home blends modern upgrades with Old Florida charm in a peaceful secluded location. Featuring 3 bedrooms, 3 full baths, and a large downstairs flex space, its perfect for relaxing or entertaining. Set on an oversized 15,000+ sq ft lot with lush landscaping and a rooftop deck, the home feels like a private retreat. Upgrades includes, new buried electrical lines and panels, and impact windows throughout. Enjoy access to a shared day dock with a full easement--great for kayaking, swimming, or fishing in the bay. (Note: boating rights not included.) Located in the heart of Islamorada, this home offers elegance, privacy, and island living at its finest.

$1,574,900
Plantation Key
Indian Waterways   - MM: 89.00
3 Bed, 3 Baths, 1,769 SqFt Days Listed: 75
-3.08% ($50,100) 2 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Ramp

This is it!! Your Florida Key Oasis! Quintessentially Key-z, this home has it all ... and then some. Located in the very desirable Indian Waterways Community of Tavernier on Plantation Key. Stylish Two Bedroom / Two Bath Main house plus a super inviting 1/1 guest house that your guests will never want to leave! Relax and entertain in the canal front Tiki hut as you enjoy tropical breezes. Cool off on the Custom Outdoor Shower after you dock your boat. Composite Dock ensures longtime enjoyment. And an Outstanding Double-sided Garage + storage room is a major Bonus!!! As Well as the personal boat ramp, that is perfect for launching/storing a flats boat, skiff, Jet Ski, or Kayak. Both the Main House and Guest House boast gorgeous, exposed wood-beamed ceilings that are gleaming works of Art. Large Bedrooms and stylishly updated Bathrooms. Great privacy with a nature preserve across the Street CBS Construction and a White Picket Fence add to the irresistible charm of this property that personifies Tropical Chic. Super Close proximity to Tavernier Creek via the famous Toilet Set Cut. World Class deep water, reef, and backcountry fishing are mere minutes away as are incredible diving, snorkeling, Lobstering, and sandbar-ing! Come Grab a slice of Florida Keys Living!

$1,590,000
Plantation Key
Plantation Beach   - MM: 87.50
3 Bed, 3 Baths, 2,117 SqFt Days Listed: 28
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Nestled on a generous half-acre lot in one of Plantation Keys most sought-after neighborhoods, this stunning 3-bedroom, 2.5-bath home with a dedicated office offers the perfect blend of comfort, style, and island living. Boasting 2,117 sq ft of interior space, this property also includes a small guest quarters--ideal for extended family or visiting friends.Step inside to discover a bright, open-concept layout with tasteful finishes and an easy flow from the living room to the dining area and kitchen. The dedicated office provides the flexibility to work from home in peace, while the spacious primary suite offers a private sanctuary complete with an en-suite bath. Step outside and youll find an entertainers paradise. The heated swimming pool with a waterfall is perfect for year-round enjoyment, while the covered outdoor entertainment area and cozy fire pit create the ideal setting for gatherings under the stars. The oversized two-car garage offers ample room for vehicles, tools, and toys--plus extra space for your boating or fishing gear. Lush tropical landscaping surrounds the home, offering privacy and a true sense of tranquility just minutes from schools, marinas, restaurants, and all that the Florida Keys lifestyle has to offer. The community offers one of the most premier homeowner parks in the Upper Keys with an exceptional blend of amenities and natural beauty. Enjoy a private beach, boat ramp, and temporary dockage--perfect for boating enthusiasts. Soak in breathtaking sunsets over the water and take advantage of a tranquil setting that captures the best of Florida Keys living.Whether youre looking for a full-time residence, vacation home, or investment opportunity, this rare gem on Plantation Key has it all.

$1,650,000
Lower Matecumbe
White Marlin Beach   - MM: 74.50
3 Bed, 3 Baths, 1,278 SqFt Days Listed: 34
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Ramp

Discover the ultimate waterfront retreat in the heart of Islamorada, in the highly sought after neighborhood of White Marlin Beach. This captivating 3-bedroom, 2-bathroom gem is a dream come true. The interior features an open floor plan with 9-foot ceilings and ceramic tile. Embrace the coastal lifestyle with stunning water views right from your backyard and revel in the convenience of a private boat ramp and dock. Take a short trip just a couple blocks away to your private homeowners park with sandy beach. Safety and security are paramount, thanks to the fully fenced yard with electric sliding gate and impact windows and doors. The one-car garage, carport and shop provide space for multiple vehicles and hobby projects.

$1,660,000
Lower Matecumbe
White Marlin Beach   - MM: 74.50
3 Bed, 3 Baths, 1,380 SqFt Days Listed: 146
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 18ft.

BEAUTIFUL WATER FRONT WHITE MARLIN BEACH HOME. THIS NEWLY UPDATED CBS CONSTRUCTION HOUSE HAS A PRIVATE BAY FRONT WHITE MARLIN BEACH HOME OWNER PARK DOWN THE STREET. HIGH END APPLIANCES WITH VAULTED CEILINGS, IMPACT DOORS/WINDOWS AND METAL ROOF. THE HOME FEATURES A BEAUTIFUL DOCK THROUGH THE MANGROVES WHICH CAN ACCOMMODATE A 22 FT BOAT WITH DIRECT ACESS TO THE BAY. PLEASE CONTACT LISTING AGENT FOR SHOWINGS.

$1,699,000
Upper Matecumbe Key Islamorada
Hammock   - MM: 83.50
4 Bed, 4 Baths, 2,277 SqFt Days Listed: 18
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Stunning new custom home in the heart of Islamorada. This exceptional, brand-new ground-level home was thoughtfully designed and expertly crafted with meticulous attention to detail. A professional interior designer curated high-end fixtures and elegant finishes throughout, creating a polished and inviting living space.Offering a rare 4-bedroom, 3-bathroom split floorplan, the home features a spacious open-concept layout ideal for both everyday living and entertaining. Soaring 10-foot vaulted ceilings and oversized 8-foot doors define the homes modern architectural style.Additional highlights include a two-car garage, a heated swimming pool, and quality construction that sets a new standard for homes in the area.Located in desirable downtown Islamorada, youre close to popular restaurants, shopping, a grocery store, and a beloved brewery. With new construction permits currently suspended in Islamorada, opportunities like this are becoming increasingly rare.Dont miss your chance to own one of the last newly built homes in this prime location - this property truly checks all the boxes.

$2,049,000
Plantation Key
Plantation Key Colony   - MM: 90.00
3 Bed, 3 Baths, 1,295 SqFt Days Listed: 330
-1.91% ($40,000) 1 Price Change : Last Change 65 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits,Boat Lift,Dav

**Waterfront Paradise: Solid Concrete Home on Deep Water Canal**Nestled along a serene deep water canal, this exquisite solid concrete home awaits its new owner. Embark on a brick paver driveway that leads to a turn-key residence designed to impress.As a boaters paradise, this property boasts a private boat lift, davit, clean out station, and outdoor shower. Access to the communitys boat ramp allows for effortless excursions.Step inside and be captivated by the beautifully furnished interior with breathtaking canal views. The open floor plan seamlessly blends the gourmet kitchen, dining area, and living room, offering an inviting space for entertaining and relaxation. Top-of-the-line appliances and entertainment areas elevate the living experience.The spacious master bedroom and bathroom provide a luxurious oasis with access to a large screened balcony. The master bathroom features a soaking tub, separate shower, and double vanity.The downstairs level offers an enclosed garage with two bay doors and ample storage. A custom-made bar, full bathroom, and additional storage space create a versatile flex room perfect for various uses.The propertys tranquil exterior features lush landscaping, gardens, and a charming front porch. The rear stairs provide convenient access to the waterfront.With a straight shot to the bay and just around the corner from the ocean via Tavernier Creek, this home offers unparalleled access to the water. The neighborhood community offers a boat ramp for members.This dream home is a rare find. Dont miss this opportunity to own a piece of paradise. Call today to schedule a private showing and experience the beauty of this solid concrete waterfront residence. Call Today!

$2,100,000
Lower Matecumbe
White Marlin Beach   - MM: 74.50
3 Bed, 3 Baths, 1,263 SqFt Days Listed: 35
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davit Pads50ft.

Welcome to paradise! This inviting home features an open-concept living area, complete with a master bedroom, a guest bedroom, a large loft that houses two cozy queen beds, and two bathrooms. This well-maintained three-story home offers ample storage, including a convenient ground-level storage area and workshop. Step outside to enjoy a brand-new refreshing saltwater pool, expansive patio and lush turf. Nestled on a cul-de-sac street, this home is set back from the Overseas Highway in a golf-cart-friendly community. From your 50 dock its quick access to bay and ocean through the Channel #2 and Channel #5 bridges. Relish stunning sunsets at your private neighborhood beach, complete with relaxing chairs, tiki huts, and grills to cook your catch. New metal roof in 2022, newer central A/C and many updates make this the perfect primary residence, second home or turn-key vacation rental!

$2,200,000
Plantation Key
Kahiki Harbor   - MM: 91.00
4 Bed, 4 Baths, 1,708 SqFt Days Listed: 108
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits,Other Dockage

Now Available! One-of-a-kind Opportunity in the desirable Kahiki Harbor neighborhood. 165 waterfront Corner Lot. Vintage 4 bedroom / 3 bath Custom built Keys home. 2/2 upstairs and a Great Room with all doors opening to the walk-around porch. Downstairs has 700 of additional enclosed storage, laundry, bathroom and two bedrooms. The home sits in the peaceful Kahiki Harbor neighborhood with deep water dockage all the way around the property. Davits and a concrete dock at one end, with additional dockage areas, a Gazebo and a Sailboat Launch Ramp following the corner of the 8,760 oversized lot. The large yard offers potential for a pool and outside entertaining areas. Endless possibilities await!- Build your Dream Home on this Unique and One-of-a-Kind Property, just off Tavernier Creek and minutes from the Ocean or Bay.

$2,222,000
Lower Matecumbe
Port Antigua   - MM: 74.50
3 Bed, 3 Baths, 1,560 SqFt Days Listed: 25
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits60ft.Concrete

Well priced and ready for a new family! This home has been UPDATED beautifully and has 3 bedrooms and 2 baths on the main living level. It is just waiting for a new family to begin living their best Port Antigua life! The downstairs breezeway affords a large shady area for entertaining or relaxing. Upstairs you will be greeted by an open expansive floor plan. All the windows and doors are now impact resistant and the CBS construction and concrete roof will give you peace of mind if there is a storm on the horizon. The main living level features an open floor plan with the kitchen, dining and living areas spanning the canalside of the home. All the bedrooms have ample closet space and the laundry room provides additional storage. On the ground level there is a very large storage enclosure for all of your boating paraphernalia that needs to be kept out of the weather and a large open entertaining area. Dont delay, this could be your dream home in Port Antigua!!

$2,300,000
Lower Matecumbe
Fantasy Harbor   - MM: 77.00
3 Bed, 3 Baths, 2,000 SqFt Days Listed: 243
-4.17% ($100,000) 1 Price Change : Last Change 70 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Basin99ft.

Make all of your Florida Keys fantasies come true at Fantasy Harbor! Were willing to bet you never even knew this gated community on Islamoradas Lower Matecumbe existed. This concrete harborfront home is being offered for the very first time. Upstairs 2 bedroom 2 bathrooms suites with open and spacious harborview living areas plus downstairs bedroom and bathroom with a bonus party hut reminiscent of relaxing Bahamian nights after a day on the water. Quiet & private living situated just off the Florida Bay in a protected harbor with 99 concrete seawall on cap rock plus boat lift. This one is a winner!

$2,300,000
Lower Matecumbe
Port Antigua   - MM: 74.50
2 Bed, 2 Baths, 1,178 SqFt Days Listed: 168
-8.00% ($200,000) 1 Price Change : Last Change 94 Days Ago
Single Family - Contingent - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift

This solid concrete home is located in one of Lower Matecumbes most sought-after subdivisions, offering 75 feet of prime waterfrontage on a peaceful canal with serene nature views--no neighboring homes across canal. The ground level features a permitted bath, a spacious workshop, and a carport with soaring high ceilings, providing ample storage.Enjoy your private slice of paradise with a dock complete with a Tiki hut for shade, and a 16,000 lb. 4-post boat lift, ideal for boating enthusiasts. The expansive backyard offers plenty of space to build your dream pool.With a little polish, this gem has endless potential to become your perfect waterfront oasis! Dont miss out on this unique opportunity!

$2,395,000
Lower Matecumbe
Port Antigua   - MM: 74.50
2 Bed, 2 Baths, 1,228 SqFt Days Listed: 88
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift70ft.Concre

What does everyone want? The smallest house in the best neighborhood! This is the one! This home has been beautifully updated and is being sold furnished including kitchen wares, dishes and linens. Dont worry about the weather, impact windows and doors have been installed throughout including the 3 skylights in the concrete roof! The pleasing open floor plan will easily accommodate your friends and family and triple sliding glass doors open to the second floor terrace. A separate laundry room is conveniently located by the kitchen. Both bedrooms have sliding glass doors to an open terrace that let in lots of natural light. Downstairs youll find ample storage and a 70 ft. concrete dock with fishcleaning stand and boat lift. The yard is very low maintenance with river rock in the front with a nice concrete driveway and artificial turf in the back. This is the one youve been waiting for, easy Keysy living in Port Antigua!

$2,499,999
Lower Matecumbe
Port Antigua   - MM: 74.50
3 Bed, 3 Baths, 2,432 SqFt Days Listed: 490
-13.79% ($400,001) 3 Price Changes : Last Change 36 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits65ft.

Welcome to this exquisitely designed home located in beautiful Port Antigua. This is an entertainers delight featuring marble flooring throughout the home. It boasts 2 full kitchens, one of which is outdoors so you can bring your fresh catch in from the boat and start cooking immediately while the smell of night blooming jasmine envelops you.There is a fully fenced in yard for your furry friends. Youll have a 65 foot dock for your boat to spend days on the crystal clear blue waters that surround our beautiful islands.This home has 3 bedrooms and 3 1/2 baths, a beautiful indoor bar with the ability to add another shower in the downstairs half bathroom.Youll be proud to call this house home.

$2,599,000
Lower Matecumbe
Port Antigua   - MM: 74.50
3 Bed, 3 Baths, 2,010 SqFt Days Listed: 84
-3.74% ($101,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift45ft.

Welcome to Port Antigua!This beautiful Key West-style home in Port Antigua boasts an open floor plan with a spacious kitchen featuring a large center island. The main living area on the second floor includes three bedrooms and two bathrooms, while the first floor offers an entertainment room that could serve as a fourth bedroom.Two sets of sliding glass doors lead to a screened-in porch overlooking the canal, perfect for enjoying the waterfront views. The home is equipped with high-impact-resistant windows and doors for added security and energy efficiency.Boaters will appreciate the 45-foot concrete dock with a 15,000 lb-rated boat lift, making it easy to enjoy life on the water. As part of Port Antiguas Homeowners Association, residents have exclusive access to a private beach with breathtaking year-round sunsets.This is a fantastic opportunity to embrace the Keys lifestyle--dont miss out!

$2,695,000
Upper Matecumbe Key Islamorada
Madeira Bay   - MM: 82.50
4 Bed, 4 Baths, 2,728 SqFt Days Listed: 56
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: Assigned Dock,Boat S

Open Bay Views, Boat Dockage and more... all in the Heart of Downtown Islamorada! Have you been dreaming of living downtown, but cant find a home with dedicated boat dockage and open water views? If so, this custom home in Madeira Bay is your dream come true! Enjoy open water views from the porch, living room, kitchen, loft and bedroom plus soaring ceilings and lots of living space. The Madeira Bay gated community is a hidden treasure of only 8 homes tucked in behind one of Islamoradas most beloved local restaurants in a peaceful private neighborhood. In addition to the community dock there is also a community pool and a gradual shoreline for launching a boat, paddle board or kayak or for wading directly into the bay with your rafts and floats! Stunning great room opens to the bay view porch on the main living level where there are also three bedrooms and two full baths in a split plan. There is also an open loft bedroom with full bath upstairs off the great room featuring beautiful bay views. The fully permitted downstairs is connected by internal spiral stairs and adds a separate ground level entrance plus a spacious second living room, wet bar area for entertaining, plus a private guest bedroom with a full bath and outdoor porch. There is also an attached garage for protected parking and/or storage. The downtown location offers immediate access to shopping, fine dining, bars, galleries, art studios and all the regular local art festivals, full moon parties and events. Madeira Bay homes rarely come on the market and this one is a must see!

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 06-15-2025.
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