Islamorada Waterfront Homes for Sale, Single Family Houses, Open Water, Ocean and Bay / Gulf Views

Waterfront real estate in Islamorada is very popular within the Florida Keys real estate market.  Homes for sale on the water in Islamorada include those that are located on the ocean, the bay, and on the many canals that lead to open water throughout the area.  Since Islamorada draws fishing enthusiasts from around the world, the bayfront and oceanfront homes for sale in Islamorada are great for real estate buyers looking to capitalize on the best features of the area.  Browse all Florida Keys MLS listings of waterfront homes for sale in Islamorada below.

Total Listings 115
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144  Bayview Drive  For Sale, MLS 573791
Lower Matecumbe
Safety Harbor   - MM: 74.00
3 Bed, 3 Baths, 3,805 SqFt Days Listed: 1126
-12.93% ($504,000) 18 Price Changes : Last Change 68 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Basin113ft.

Beyond compare, this Polynesian inspired exquisite keys waterway Harum Designed custom home is 99% complete, pool is in, landscaping is underway. This spectacular home is not to be missed if you are looking for a yachtsmans location w/over 110ft of deep water dockage w/unlimited beam on deep water Hurricane Creek. Cathedral ceilings grace this masterpiece and its 3 bedroom and 3.5 baths is complimented by custom LED lighting, drop down TV. Incredible storage, 2 garages, generous and spacious covered gathering areas. The residence boasts an extraordinary creekside covered balconies overlooking Hurricane Creek with views of the Florida Bay making this a Florida Keys Treasure. The finished work detail is to much to list. Contact agent for full details and showing appointment.

140  Atlantic Lane  For Sale, MLS 588337
Lower Matecumbe
Mar Celeste   - MM: 76.00
5 Bed, 5 Baths, 2,868 SqFt Days Listed: 88
-2.40% ($45,000) 7 Price Changes : Last Change 7 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 220ft.Concrete

OCEANFRONT INVESTMENT OPPORTUNITY! This is your chance to be the 2nd owner of this oceanfront property with 220 concrete, canal dockage. Operated as a vacation rental with extensive, interior renovation in 2015 and exterior renovation, post-Irma in 2017, the main house features Master En Suite with bath/office/den upstairs; main kitchen and living area along with two guest bedrooms with two full baths on the main level with permitted storage downstairs. The attached guest cottage features a kitchette, living room, two guest bedrooms with full bath. From sunrise to sunset, enjoy panoramic ocean views and aquatic wildlife. With gated entry, fencing, & three sides surrounded by water, continue use as a vacation rental or your own private, oceanfront compound-A true Keys Retreat!

88547  Old Highway  For Sale, MLS 576121
Plantation Key
Key Heights   - MM: 88.50
4 Bed, 4 Baths, 4,103 SqFt Days Listed: 961
+4.65% ($200,000) 6 Price Changes : Last Change 492 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift,Davits400f

Open Oceanfront Estate with Deep Dockage on 1.5 Acres on Millionaires Row... Islamoradas premier address. Brand new dock with two new boat lifts to enjoy the best boating in the Keys! Spacious 4,103 s.f. home with 4 bedrooms, 3 full baths, a large heated pool, winding private driveway, and a soaring central atrium surrounded by walls of windows to frame the ocean view. Open ocean views from the living room, Florida room, porches, master bedroom and upstairs loft. Living room with wet bar and pass-through window to the gourmet kitchen and separate dining room, all with Saturnia stone floors. Direct boating access to the best offshore fishing and diving, plus quick Florida Bay access. RE Zoning allows weekly rentals for income potential. Call today!

100  Venetian Drive  For Sale, MLS 586439
Lower Matecumbe
White Marlin Beach   - MM: 74.50
2 Bed, 2 Baths, 1,080 SqFt Days Listed: 223
-10.22% ($91,000) 5 Price Changes : Last Change 11 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

Amazing views from this immaculate 2 bedroom 2 bath waterfront home on pristine canal with access to both Bay and Ocean. Panoramic views of large conservation area and lake allow privacy as there are no rear neighbors. Open concept plan with new metal roof, kitchen has new stainless steel appliances including refrigerator, stove and microwave. 1080 sq ft living area plus large patio and dock for your boat. House is built high enough to allow doubling of square footage by enclosing downstairs area. Opened unfinished attic for added storage space or future loft. Beautiful private homeowners beach on Bayside.

82994  Overseas Highway 23 For Sale, MLS 579971
Upper Matecumbe Key Islamorada
Penn Key Club   - MM: 83.00
3 Bed, 3 Baths, 1,812 SqFt Days Listed: 658
-28.60% ($1,001,000) 5 Price Changes : Last Change 38 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Assigned Dock,Dock P

A classic Islamorada retreat. This private home is located in the exclusive bayfront gated community of Pen Key Club in the heart of Islamorada. The lovely one-story home offers three bedrooms and three bathrooms with panoramic views of the open water from every angle. Enjoy magnificent sunsets while relaxing in the living room or charming sitting areas on the open bay. In addition, the Pen Key Club offers a pool and boat dockage in a protected boat basin. This offering is Florida Keys living at its finest!

110  Bayview Isle Drive  For Sale, MLS 574354
Plantation Key
Venetian Shores   - MM: 86.00
4 Bed, 4 Baths, 3,240 SqFt Days Listed: 1093
-22.97% ($850,000) 4 Price Changes : Last Change 117 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift140ft.

ANCHORS AWEIGH - 140 of deep-water, protected, concrete/paved dockage is enjoyed at this serenely secluded property with sunset views. It is rare to find 2 adjoining lots in Venetian Shores with beautiful bay views, and convenient, direct access to Snake Creek. Remodeled in 2005 & designed to take advantage of magnificent views from every level. Downstairs rec room also used as 5th bedroom.

298  South Drive  For Sale, MLS 581391
Plantation Key
Plantation Lake Estates   - MM: 87.00
4 Bed, 4 Baths, 3,938 SqFt Days Listed: 560
-20.04% ($1,000,000) 4 Price Changes : Last Change 126 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Basin,Boat Lift38ft.

This Islamorada Gem is located in a very private ocean front enclave. The open living/dining area over looks the ocean with 20 ceilings through floor to ceiling windows. Both master suites open to ocean view terraces. A luxurious den with 50 flat screen Apple TV is a quiet retreat. All levels are serviced by elevator. Situated on a gated 1/2 acre lushly landscaped lot with paver drive and two car garage, this home is one of only 4 in the enclave. The 38 protected dock has 20K LB lift in the HOA marina. The new marina park is newly landscaped. Concrete pool and spa has new equipment. A fully equipped poolside bar has new appliances including stainless grill, refrigerator and Ice maker. Quality construction with West Indies design. Offered furnished.

118  Sea Lane  For Sale, MLS 588757
Lower Matecumbe
Mate Lido Beach   - MM: 76.00
3 Bed, 3 Baths, 1,677 SqFt Days Listed: 61
-2.22% ($20,000) 3 Price Changes : Last Change 6 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 75ft.

Spacious waterfront home on ocean side of Lower Matecumbe offering immediate access to the Atlantic, the reef and some of the Keys best access to fishing and water activities. 3 bedrooms & 2 baths in the main part of the house with a 1/1 ground level bonus garage apartment. Vaulted ceilings, fresh kitchen, split level in design. Open living floor plan with large rooms compliment this keys home. 75ft on the water with literally a straight shot out to the Atlantic! Located at MM76, close to all the Village has to offer yet far enough away to enjoy the tranquility of Lower Matecumbe. Call for appointment. Owner Occupied so notice is appreciated and they are ready to make a deal!

75180  Overseas Highway  For Sale, MLS 585065
Lower Matecumbe
Unplatted Lower Mate   - MM: 76.00
3 Bed, 3 Baths, 1,803 SqFt Days Listed: 320
-10.89% ($195,000) 3 Price Changes : Last Change 159 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

Awesome, bayfront, property on Lower Matecumbe with everything a family needs to enjoy the Keys lifestyle! Deep water dockage, natural private sand beach, endless bay views, tiki hut with bar, and thats just outside. Inside enjoy travertine floors, media room, custom glass etched bar, cargo lift, separate laundry room and remolded 1/1 downstairs . Perfect for any fisherman the property is conveniently located with endless access to inshore angling and a short run to ocean with no fixed bridges. Owner financing possible and a realistic price make this a must see. More photos coming soon!

75475  Overseas Highway  For Sale, MLS 588194
Lower Matecumbe
Lower Mat Harbor   - MM: 75.00
3 Bed, 3 Baths, 1,825 SqFt Days Listed: 98
-5.03% ($110,000) 3 Price Changes : Last Change 16 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Ramp,DavitsConc

PLENTY OF ROOM TO LAND YOUR HELICOPTER! Almost an ACRE of Oceanfront property with dockage, pool and garage!! This unique oceanfront peninsula on Lower Matecumbe is just what you are looking for! You have ocean views and almost an acre of property! Enter through the gate and follow the driveway to the parking area and garage. The pool area looks out to the ocean, observation pier and boat dock. This beautifully updated home has a split bedroom plan and open concept living space which allows for ocean views from almost every room. On the main floor, gracious sliding glass doors open from the oceanfront porch to the open living areas and kitchen. The kitchen has granite countertops and the large cooking island has fantastic ocean views. Alligator Lighthouse appears within reach! More....

202  Johnny Road  For Sale, MLS 585260
Plantation Key
Boatmans Colony   - MM: 90.50
2 Bed, 2 Baths, 1,372 SqFt Days Listed: 306
-5.72% ($44,000) 2 Price Changes : Last Change 157 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

Moments to the ocean or bay, this waterfront home is right off Tavernier Creek. The homes unique features include open ceilings with exposed beams, lots of natural light, wood floors, and a huge side porch. The open chefs kitchen features a commercial double oven and gas range. On a corner lot, the property offers two parking areas, plus an RV hookup with 50 amps of power. The upstairs includes a half bathroom, and a renovated master suite with a gorgeous full bathroom. Downstairs there are two bedrooms and one bathroom. Upgrades include a newer roof and air conditioning.

125  Cortez Drive  For Sale, MLS 588045
Lower Matecumbe
Mat Ocean View   - MM: 76.50
2 Bed, 2 Baths, 1,071 SqFt Days Listed: 106
-2.50% ($20,000) 2 Price Changes : Last Change 25 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift,Boat Ramp

Just what youve been looking for?A Keys get away w/immediate access to ocean, the reef, off shore fishing, close to Indian Key Fill Cut to strike out into the back country. This 2 bedroom 1.5 bath is just right! Fresh baths and brand new kitchen cabinets and appliances compliment this all masonry (including roof) residence on Lower Matecumbe. Close to everything that is Islamorada; dining, charters, marinas, Worldwide Sportman, diving/snorkling or hang out in your very own piece of paradise. Full garage to store your toys, 15K boat elevator, 75ft of concrete dock, neighborhood boat ramp. Ground level enclosure is all storage and conforming so home is insurable. Put your finishing touches on this keys treasure and make it your own. Owner occupied so appointment with notice appreciated.

126  Bessie Road  For Sale, MLS 580681
Plantation Key
Tropical Atlantic Shores   - MM: 90.00
4 Bed, 4 Baths, 1,980 SqFt Days Listed: 609
-4.40% ($55,000) 2 Price Changes : Last Change 223 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift65ft.

Calling all families and friends looking for two separate complete living spaces Up and Down! 4 bedrooms and 2 baths, nearly 2,000 square feet of living space. Turn Key, completely updated and renovated waterfront home, including all new electrical and plumbing! Ocean side with direct ocean access. Located In Plantation Key (Islamorada) next to Tavernier Creek, this concrete home including the roof, boasts all impact glass windows , neutral porcelain tiles, custom wood cabinetry, open concept living with bar, Spa style bathrooms, granite counter tops, stainless appliances, extensive brick pavers, a fully fenced yard with custom aluminum work, professional landscaping, electric retractable sunshade, new outdoor kitchen with chiseled travertine , tiki hut at waters edge, 1 Hr to MIA.

189  Sunset Drive  For Sale, MLS 585442
Lower Matecumbe
Lower Mat Beach   - MM: 74.00
2 Bed, 2 Baths, 1,040 SqFt Days Listed: 294
-6.90% ($100,000) 2 Price Changes : Last Change 34 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

Incredible Beachfront Property! This 2 bedroom 2 bathroom beachfront home in this quiet neighborhood close to the excitement and heart of Islamorada offers a sandy beach great for turtle watching, plenty of space for lounging in the sun or just enjoying an afternoon drink on the screened porch overlooking the Atlantic Ocean! Both bedrooms boast a beautifully remodeled en-suite full bathroom and endless views of the beach and open water. Whether this is your vacation home, primary home or a vacation rental property, this home has a little something for everyone.

137  Severino Drive  For Sale, MLS 586960
Plantation Key
Venetian Shores   - MM: 86.00
5 Bed, 5 Baths, 2,728 SqFt Days Listed: 190
-8.81% ($154,000) 2 Price Changes : Last Change 22 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits100ft.Concrete

9-26-19 REDUCED $100,000...This is the perfect home for an extended family with a total of 5 bedrooms and 4 baths with 100 of dockage located in Islamoradas premier neighborhood of Venetian Shores. The main level features an inside foyer and staircase, vaulted living room that opens to a private balcony, updated granite & s.s. kitchen, 3 BRs, 2 BAs (2 Guest BRs plus Mstr Suite - split floorplan - updated baths), and a large terrace with outdoor kitchen + 10 person spa! Theres also a 3rd level loft/family room. Downstairs are 2 Guest Apartments - legally permitted and above flood, 2 car garage, storage room, and a large covered area perfect for games, dining, whatever you dream of! Room for your & your friends boats and minutes to the ocean or bay via Snake Creek.

257  Sunset Drive  For Sale, MLS 584078
Lower Matecumbe
Lower Mat Beach   - MM: 74.00
3 Bed, 3 Baths, 1,674 SqFt Days Listed: 381
-20.37% ($509,000) 2 Price Changes : Last Change 209 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

One of the best values in all of the Florida Keys in a much sought-after location. Being sold by the homes second owner. The first owner was the builder and architect. The home has been completely upgraded and is ready to enjoy. Sit on the deck and watch the fish swim by, or wade out and hook up. This is a true beach house, with endless ocean views, silky sand beach, and clear Atlantic waters to enjoy. This home has the infrastructure to add a third floor for additional space and views. Upstairs there is one bedroom and one bathroom with a large laundry closet space. Downstairs is comprised of two bedrooms and one bathroom. Both levels offer large porches overlooking the Atlantic Ocean and the propertys beautiful beach with views of the sunrise and sunset.

80531  Old Highway  For Sale, MLS 584600
Upper Matecumbe Key Islamorada
Unplatted Upper Mate   - MM: 82.00
3 Bed, 3 Baths, 2,044 SqFt Days Listed: 351
-17.29% ($669,000) 2 Price Changes : Last Change 58 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None,Other DockageCo

Motivated Seller! Owner Finance Possible! One-of-a-kind 3 plus-acre estate on Upper Matecumbe Key. You will follow the classic brick driveway to one of Islamoradas most private settings. The main house, (above the flood zone), offers two bedrooms and two-and-a-half bathrooms, featuring high beamed ceilings, tile floors, and ocean views. A guest cottage offers one bedroom, one bathroom, and a large sitting room. Watch the colors of beautiful sunrises and incredible sunsets reflect off Alligator Lighthouse from all rooms. Look for tailing bonefish and wading birds, or just sit by the pool and relax--Mother Nature is your living room. A caretakers cottage as well as a guest cottage can be added to the property as of right. Two additional lots have the possibility to be rezoned

178 N Coconut Palm Boulevard  For Sale, MLS 589406
Plantation Key
Plantation Key Colony   - MM: 90.00
3 Bed, 3 Baths, 1,486 SqFt Days Listed: 23
-2.88% ($20,000) 1 Price Change : Last Change 5 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Concrete

Canal front home in Plantation Key Colony, 2 bedrooms, 1 bath upstairs and 1 bedroom, 1 bath studio downstairs, with over 1400sf combined. New metal roof in October 2019. Screened 7x24 balcony. 50 seawall dockage with fish cleaning station and outdoor shower, wooden 7x11 work shed, great landscaping in place. Downstairs is above flood according to permit drawings. Close to great schools, restaurants, hospital, and shopping. Great homeowners park with dockage, boat ramp and picnic area.

138  Venetian Way  For Sale, MLS 589154
Plantation Key
Venetian Shores   - MM: 86.00
4 Bed, 4 Baths, 2,055 SqFt Days Listed: 35
-6.80% ($51,000) 1 Price Change : Last Change 17 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: None

Gorgeous Venetian Shores charmer priced to sell. Seller says bring all offers. Captivating island living in large open concept home designed for entertaining as well as family living. Low insurances and easy living withno stairs to climb makes this home stand out from the rest. The beautiful master suite with huge walk in closet, large master bathroom features tub and separate fabulous spacious shower is set apart from the other threebedrooms. An relaxing waterfront screened porch running from the kitchen, across the living area to the master bedroom allows for year round outdoor living. Dockage depending on availability in marina close by, this house is a gem not to be missed. Home is currently Tenant Occupied.

179  Azalea Street  For Sale, MLS 587253
Plantation Key
Plantation Key Colony   - MM: 90.00
4 Bed, 4 Baths, 1,761 SqFt Days Listed: 162
-3.34% ($25,000) 1 Price Change : Last Change 13 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 50ft.Concrete

Price reduced again and the sellers are very motivated! This all concrete 2 story canal front home has one of the few legally permitted downstairs, consisting of two 1 bedroom 1 bathroom apartments. Upstairs is a 2 bedroom 2 bathroom along with a 8 by 24 screened in porch overlooking their 50 wide concrete dock. Very low flood insurance quote of $779.00 for the entire home. Contractors own home originally and he doubled the rebar and poured the walls solid. This home has never been damaged or flooded from a storm. It is located on the only free flowing canal in Plantation Key Colony (PKC). PKC is a highly desired subdivision as it is with in a short walking distance to the schools Grades 1-12. It is located on the 4 lane portion of US1 MM90 bayside 1 hour south of Miami.

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 02-17-2020.

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