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

Total Listings 115
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133  Sunset Drive  For Sale, MLS 586113
$2,495,000
Lower Matecumbe
Lower Mat Beach   - MM: 74.00
4 Bed, 4 Baths, 2,689 SqFt Days Listed: 256
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 20ft.

ISLAMORADA BEACHFRONT OASIS! Enjoy a natural sandy beach right outside your front door on sought after Sunset Drive on Lower Matecumbe Key. Listen to ocean waves wash up on your shoreline & lull you to sleep every night. Remodeled 4B/3B residence with great attention to detail, gourmet kitchen, separate dining area, living room with fireplace, vaulted ceilings, guest bedroom wing on main level, interior stairs encased in brazilian wood leading to 3rd level private master suite overlooking the Atlantic. Panoramic open water views from all 3 levels makes you feel as if you live on top of the water! A relaxing, elegant, turnkey home offered fully furnished for added convenience. Protected dockage on canal front outparcel. Permits applied for docking a larger vessel via boat slip @ dock.

75333  Overseas Highway  For Sale, MLS 587348
$2,499,000
Lower Matecumbe
Mat Ocean Beach   - MM: 75.00
3 Bed, 3 Baths, 2,182 SqFt Days Listed: 161
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

Gorgeous ocean front Lower Matecumbe home. Nothing but views and natural light from this 2002 built concrete fortress. Large, natural, sandy beach with new pool and outdoor kitchen allow for entertaining options that amaze. Inside tastefully updated and well maintained with all the comforts a family could need. Plenty of storage downstairs for all your water toys and enclosed garage area for the fishing enthusiasts tackle. Wade the shallows for Bonefish or just take in the breathtaking beauty of the ocean, whatever you desire this home brings your dream of keys living to life! Freshly painted exterior and interior. New ACs 2017. Popular monthly rental and offered furnished!

82994  Overseas Highway 23 For Sale, MLS 579971
$2,499,000
Upper Matecumbe Key Islamorada
Penn Key Club   - MM: 83.00
3 Bed, 3 Baths, 1,812 SqFt Days Listed: 665
-28.60% ($1,001,000) 5 Price Changes : Last Change 46 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!

91  Iroquois Drive  For Sale, MLS 588753
$2,595,000
Lower Matecumbe
Lower Mat Beach   - MM: 74.00
3 Bed, 3 Baths, 4,004 SqFt Days Listed: 69
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 42ft.

OCEAN VIEW GATED ESTATE WITH POOL, BEACH & DOCKAGE! This beautiful resort style ocean view home is situated on a point lot with over 1/2 acre of land offering over 4,000 sq ft of living space, 3 bedrooms, 3 bathrooms with 2 ocean front master stes, open floor plan w/soaring ceilings, oceanfront porch, 6 car garage, lush tropical landscaping surrounding a putting green, elevator, deep water dockage with immediate ocean & bay access. Located in the Sports Fishing Capital of the World, Islamorada, Florida Keys. Dont miss this outstanding opportunity!

161  Sunset Drive  For Sale, MLS 589029
$2,700,000
Lower Matecumbe
Lower Mat Beach   - MM: 74.00
3 Bed, 3 Baths, 2,940 SqFt Days Listed: 48
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

Sunrise on Sunset!Sweeping views to the open ocean from this super sturdy concrete home with concrete roof. Stately home sits on a double sized lot and fronts a real & rare sandy beach. Open floor plan, cathedral ceiling, new kitchen, new impact windows & doors, oceanfront porch with wrap around balcony, oodles of storage plus bonus 1BA/1BA downstairs. Located between Alligator & Tennessee Lights and just north of Channel 2 & 5 bridges for quick bay access. Owner has architectural plans for pool ready for permitting so buy now and you can decide where it goes! Lot across street in permitting available as a package with home or cattycorner canal lot 16 also available. See MLS #s 589029 & 589026.

110  Bayview Isle Drive  For Sale, MLS 574354
$2,850,000
Plantation Key
Venetian Shores   - MM: 86.00
4 Bed, 4 Baths, 3,240 SqFt Days Listed: 1100
-22.97% ($850,000) 4 Price Changes : Last Change 125 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.

75445  Overseas Highway  For Sale, MLS 586728
$2,999,000
Lower Matecumbe
Matecumbe Ocean Bay   - MM: 75.00
4 Bed, 4 Baths, 3,185 SqFt Days Listed: 208
-7.44% ($241,000) 1 Price Change : Last Change 42 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Other Dockage

OCEANFRONT ESTATE! Behind the gate and concrete wall surrounding this property, you will find the most beautifully remodeled, four bedroom, four and one-half bath home, overlooking the Atlantic Ocean. Three en suite bedrooms feel like master suites with phenomenal views. Fourth bedroom and adjacent bath located its in own wing. Open gathering space with built-in workspace and wet bar; amazing modern kitchen. Featuring a sandy beach complete with horseshoes & hammock, a grand, in-ground pool, boat ramp, concrete seawall and potential for dockage! Three exterior terraces/lanais for entertaining or private sunbathing all with incredible ocean views. The half bath is serviceable by a door leading to pool. One car garage and plenty of parking outside for vehicles/RV. Paradise Found!

191  Plantation Shores Drive  For Sale, MLS 589884
$2,999,000
Plantation Key
Plantation Shores   - MM: 90.00
4 Bed, 4 Baths, 3,401 SqFt Days Listed: 6
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 86ft.Concrete

Oceanfront, custom concrete luxury home, offering 85.5ft. of protected dockage! Beautiful Waterfront Pool and Spa! Unobstructed Sunrise Views, beautiful Kitchen, Impact Doors and Windows, 4 bedrooms, 4 full baths, open floor plan, garage, lots of storage for all of your water toys! This home has it all!! Great for entertaining lower level poolside area! Truly a must see!

80531  Old Highway  For Sale, MLS 584600
$3,200,000
Upper Matecumbe Key Islamorada
Unplatted Upper Mate   - MM: 82.00
3 Bed, 3 Baths, 2,044 SqFt Days Listed: 358
-17.29% ($669,000) 2 Price Changes : Last Change 66 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

75971  Overseas Highway  For Sale, MLS 588803
$3,295,000
Lower Matecumbe
Mat Ocean Bay   - MM: 75.00
4 Bed, 4 Baths, 6,065 SqFt Days Listed: 66
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None,Other Dockage

Stunning Beachfront Estate & Income Property! A successful weekly vacation rental, Turtle Nest Estate has achieved an average gross income of $200,000/year so this property could potentially be self-funding! Booked leases and will be transferred to buyer upon sale. In addition to rental income, you can also enjoy your own tropical beachfront paradise in desirable Islamorada near all the most popular diving and fishing spots. Relax on the 150-foot beach, soak in some rays by the pool, or enjoy nearby fine dining, entertainment & local attractions. This luxurious home offers more than 6,000 sf under air, an oceanfront pool with integrated hot tub, a wade-in sandy beach and an observation pier. Two-car garage, elevator, theater room, split plan, guest wing & more!

161 & 154  Sunset Drive  For Sale, MLS 589027
$3,300,000
Lower Matecumbe
Lower Mat Beach   - MM: 74.00
3 Bed, 3 Baths, 2,940 SqFt Days Listed: 48
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davit Pads,Davits89f

Sunrise on Sunset!Sweeping views to the open ocean from this super sturdy concrete home with concrete roof. Stately home sits on a double sized lot and fronts a real & rare sandy beach. Open floor plan, cathedral ceiling, new kitchen, new impact windows & doors, oceanfront porch with wrap around balcony, oodles of storage plus bonus 1BA/1BA downstairs. Located between Alligator & Tennessee Lights and just north of Channel 2 & 5 bridges for quick bay access. Owner has architectural plans for pool ready for permitting so buy now and you can decide where it goes! This listing offered with 89 wide canal lot in permitting for an additional home, concrete dock & davits in place. Ocean front house may be purchased separately. Cattycorner canal lot 16 also available. See MLS #s 589027&589026

144  Bayview Drive  For Sale, MLS 573791
$3,395,000
Lower Matecumbe
Safety Harbor   - MM: 74.00
3 Bed, 3 Baths, 3,805 SqFt Days Listed: 1133
-12.93% ($504,000) 18 Price Changes : Last Change 76 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.

160  Stromboli Drive  For Sale, MLS 585753
$3,500,000
Plantation Key
Venetian Shores   - MM: 86.00
5 Bed, 5 Baths, 4,353 SqFt Days Listed: 280
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Concrete

Great views of Snake Creek and out to the ocean from this beautiful 5 bedroom home on almost 1/2 acre of creekfront lot in Venetian Shores. Approximately 130 along Snake Creek and approximately 160 along the canal. Home features split level with 4 bedrooms on 1st level, large living/kitchen area with screened balcony on mid level and master bedroom on top level, all connected with soaring open foyer. Nice pool with spa, screened outdoor grilling area, 9 hole putt-putt golf course along creek and canal, large garage, davits and nicely landscaped grounds.

262  Sunset Drive  For Sale, MLS 584415
$3,600,000
Lower Matecumbe
Lower Mat Beach   - MM: 74.00
4 Bed, 4 Baths, 2,835 SqFt Days Listed: 368
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift90ft.

Mesmerizing water views from just about every room in this four-bedroom, three-and-a-half bathroom home including downstairs guest quarters. This beautiful house with beach access has a multitude of amenities such as natural coral accents, a gourmet kitchen with custom wood cabinetry, double ovens, and bar seating. The wonderful outdoor living spaces include an in-ground pool with a heater, chiller, lights and a waterfall, and terraces with open ocean views. Additional amenities include dockage for two boats, electric shutters, a multi-car garage, a workshop, and an elevator with etched glass artistry. The third floor is all master suite with elevator access, dual walk-in closets, an office, a sitting area, a spacious master bathroom, and two balconies for sunrise and sunset views.

77001  Overseas Highway  For Sale, MLS 588012
$3,750,000
Lower Matecumbe
Mat Ocean Bay   - MM: 77.00
6 Bed, 6 Baths, 4,696 SqFt Days Listed: 116
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat RampRip Rap

Tucked away on two exquisite oceanfront acres with sandy beach is this perfect island retreat. Lush tropical gardens with tall coconut palms cocoon the 5 bedroom, 5 1/2 bath 4700SF residence plus separate poolside guest quarters. A welcoming foyer opens to a showcase stairway which leads to the top floor master suite with private oceanfront balcony and spacious master bath with double walk-in closets.The open living area with endless ocean views boasts exquisite finishes such as tiled custom bar, polished porcelain tile floors, and soothing colors reflecting the casual Keys life style. The gorgeous kitchen features a granite-topped island with high quality appliances, a pantry and laundry room. Wrap-around porches offer lazy ocean gazing over the sandy beach to the sparkling Atlantic...

298  South Drive  For Sale, MLS 581391
$3,800,000
Plantation Key
Plantation Lake Estates   - MM: 87.00
4 Bed, 4 Baths, 3,938 SqFt Days Listed: 567
-23.85% ($1,190,000) 5 Price Changes : Last Change 2 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.

80639  Old Highway 101 For Sale, MLS 587835
$3,995,000
Upper Matecumbe Key Islamorada
Maison Matecumbe   - MM: 81.00
4 Bed, 4 Baths, 2,997 SqFt Days Listed: 127
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

Welcome to Maison Residences, your private oceanfront retreat in Islamorada. Enjoy open ocean views as soon as you step inside the front door! The view widens as you walk through the kitchen and dining area to the living area and the open lanai. This same view can be enjoyed from the luxurious master bedroom and balcony. Nature lovers can watch the wading birds feeding in the shallows, the pelicans diving for breakfast and porpoises playing without leaving your porch. Views of the lawn, palm trees, beach, dock and ocean will fill our mind and entice you to come back often. This smart home was finished with great attention to detail and features 10 ft. ceilings, 9 ft. doors, 2 AC units with 3 zones, Wolf and SubZero appliances, privately keyed elevator, 86 ft. resort style pool,

1108  Venetian Boulevard  For Sale, MLS 585884
$3,995,000
Plantation Key
Venetian Shores   - MM: 86.00
5 Bed, 5 Baths, 4,696 SqFt Days Listed: 272
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Davits120f

This Venetian Shores Bay Front home offers everything for the serious boater. With 120 of concrete dock, a 60,000 # extra wide boat lift and davits for your bay boat this home can handle all your vessels. There is plenty of depth and a wide channel (88) will accommodate boats as large as 65 with easy ocean access through Snake Creek. The third floor is an open concept living room, dining room and kitchen with built in cabinets has expansive open water views. There are 3 bedrooms with fantastic views on the second floor. The master has his and her bathrooms and walk-in closets. The ground floor has two bedrooms with a Jack and Jill bathroom. There is also a storage room for all of your boating accessories. With over 12,000 sq ft this is one of the largest lots in Venetian Shores

88547  Old Highway  For Sale, MLS 576121
$4,500,000
Plantation Key
Key Heights   - MM: 88.50
4 Bed, 4 Baths, 4,103 SqFt Days Listed: 968
+4.65% ($200,000) 6 Price Changes : Last Change 500 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!

240  Costa Bravo Drive  For Sale, MLS 589104
$4,550,000
Lower Matecumbe
Port Antigua   - MM: 74.50
4 Bed, 4 Baths, 4,134 SqFt Days Listed: 45
-0.98% ($45,000) 1 Price Change : Last Change 5 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift90ft.

Celebrate sunset views EVERY night from this beachfront Port Antigua home which also has dockage across Costa Bravo Dr. on the protected canal. The main living level boasts an open floor plan and vaulted ceilings, 3 bedrooms, 3 baths plus an office! The kitchen is open to the living and dining areas so that you can enjoy views of the bay while preparing the days catch and features a large cooking island with ample seating, Stainless steel GE Profile and Jenn-Air appliances. Enjoy bay views from the living area where 12 ft. sliding glass doors pocket out of sight and open to a spacious covered porch. Everything tastes better when you are enjoying bay views from the dining area. Another set of 12 ft. sliding glass doors in the dining area pocket to let the outside in. In addition.....

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 02-24-2020.

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92300 Overseas Hwy Suite 303
Key Largo, Florida 33070

1(800) 692-3605
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