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
Order By:

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!

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.

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.

257  Sunset Drive  For Sale, MLS 584078
$1,990,000
Lower Matecumbe
Lower Mat Beach   - MM: 74.00
3 Bed, 3 Baths, 1,674 SqFt Days Listed: 388
-20.37% ($509,000) 2 Price Changes : Last Change 217 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.

83257  Old Highway  For Sale, MLS 588229
$1,998,000
Upper Matecumbe Key Islamorada
The Russell Estates   - MM: 83.50
5 Bed, 5 Baths, 3,000 SqFt Days Listed: 103
-20.08% ($502,000) 1 Price Change : Last Change 28 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Other Dockage

Natural Beach Oceanfront Estate - enjoy the barefoot elegance of this custom Poured Concrete GREEN island home. Featured in Fine Home Building & Natural Home magazines, historic Red Cross home lovingly remodeled plus 2 thoughtful, Eco friendly architect designed & built additions add modern, artistic feel. Custom Everything! Enjoy living on the best island, separate living spaces, high arched ceilings, private outdoor shower, spacious beachfront drivethrough 3 car garage, fabulous views, orchard, solar panels, cistern, and so much more! If you long for brilliant design where indoor and outdoor living are seamlessly integrated, you will love this home. Please call to schedule your private tour- experience artistic excellence, unity with nature, & sheer bliss.

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

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.

79775  Overseas Highway  For Sale, MLS 585835
$15,000,000
Upper Matecumbe Key Islamorada
Tea Table   - MM: 79.50
5 Bed, 5 Baths, 3,104 SqFt Days Listed: 277
-11.76% ($2,000,000) 1 Price Change : Last Change 145 Days Ago
Off Shore Isl - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davits40ft.

An extremely rare and stunning private island, accessible by car, Terras Key is a gated Caribbean Island located at Mile Marker 79.7 in Islamorada. Jutting into the blue-green waters of the Atlantic Ocean, Terras Key features a 2,000+- driveway enabling you to reach restaurants and shopping easily.Enjoy the conveniences of the modern world, including all utilities, while surrounded with the privacy of your own +15.5 Acre Island with miles of open water views and views of Alligator Reef Light. The compound includes 5 bedrooms and 4 baths, pool, cabana, dockage, and a tennis court. This extraordinary private island is a landmark in Islamorada and the Florida Keys and has not been offered for sale for over 27 years.

75180  Overseas Highway  For Sale, MLS 585065
$1,595,000
Lower Matecumbe
Unplatted Lower Mate   - MM: 76.00
3 Bed, 3 Baths, 1,803 SqFt Days Listed: 327
-10.89% ($195,000) 3 Price Changes : Last Change 167 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!

100  Venetian Drive  For Sale, MLS 586439
$799,000
Lower Matecumbe
White Marlin Beach   - MM: 74.50
2 Bed, 2 Baths, 1,080 SqFt Days Listed: 230
-10.22% ($91,000) 5 Price Changes : Last Change 19 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.

191  Plantation Avenue  For Sale, MLS 587978
$1,490,000
Plantation Key
Plantation Key Colony   - MM: 90.00
3 Bed, 3 Baths, 2,380 SqFt Days Listed: 117
-9.70% ($160,000) 2 Price Changes : Last Change 4 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 40ft.

ESPRIT - Architecturally modern residence encased in majestic tropical gardens that awaken the senses and are host to monarch butterflies, jasmine, gardenia, and birds of paradise. This rare custom 3BA/2.5BA CBS home offers a concrete roof, custom flooring throughout & hurricane rated windows and doors. Open and spacious kitchen with indoor/outdoor dining areas overlooking the water is designed with accent lighting and the newest modern appliances. Fast Bay to Ocean access via either nearby Tavernier Creek or Snake Creek with marina amenities available right up the canal teeming with manatee and porpoise. Rooftop party deck has 10 person hot tub and offers 360 degree views of Plantation Key and waterways adorned with beautiful birds, starry skies, breathless sunrises and romantic sunsets.

137  Severino Drive  For Sale, MLS 586960
$1,595,000
Plantation Key
Venetian Shores   - MM: 86.00
5 Bed, 5 Baths, 2,728 SqFt Days Listed: 197
-8.81% ($154,000) 2 Price Changes : Last Change 30 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.

158  Biscayne Boulevard  For Sale, MLS 584578
$1,399,000
Lower Matecumbe
Port Antigua   - MM: 74.50
3 Bed, 3 Baths, 2,069 SqFt Days Listed: 358
-8.50% ($130,000) 1 Price Change : Last Change 183 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Boat Slip

LOCATION,LOCATION, LOCATION...Rare find, just steps away from the bay with direct access.This property is located in a very desirable location in Port Antigua. This 3 bedroom 2 bath remodeled home has a private beach and boat ramp. Custom wood cabinetry with Island, stainless steel appliances, Travertine fireplace, Vaulted Ceiling, florida room with sliding glass doors that open up to the bay views and a deep water dockage with boat lift and cleaning station. downstairs has an extra room with storage with all your fishing needs. Seller is motivated and will entertain offers.

262  Navajo Street  For Sale, MLS 589079
$1,995,000
Plantation Key
Indian Waterways   - MM: 89.00
3 Bed, 3 Baths, 3,506 SqFt Days Listed: 46
-8.28% ($180,000) 1 Price Change : Last Change 4 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift110ft.

If youve been watching this home, now is your opportunity to get it at a great price. The ultimate in modern luxury designed and built by prominent local interior designer. Superbly finished with only the finest materials, every element enhances the next on this priceless masterpiece. Ideally situated along 110 of waterfront leading to one of Islamoradas favorite bays. The second and third floors combine for the main living area which leads to the all-encompassing rooftop deck. The first floor offers a separate living quarters for guests. Full outdoor kitchen alongside the state-of-the-art pool that features complete perimeter overflow and smart phone automation. The stage is set for a show-stopping Keys lifestyle!

149  Stromboli Drive  For Sale, MLS 586541
$2,200,000
Plantation Key
Venetian Shores   - MM: 86.00
5 Bed, 5 Baths, 3,884 SqFt Days Listed: 222
-8.14% ($195,000) 1 Price Change : Last Change 66 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift100ft.

NEW LOOK, NEW PRICE, EASY & READY TO SHOW! Exquisite Waterfront Pool Home with 100ft. of Dock! This elegant home features 5 bedrooms, 4 bathrooms, including 2 master suites, rich mahogany wood stair cases, porcelain tile floors, gourmet state of the art kitchen, custom built pool with heater & chiller, 33,000 lb boat lift, 100ft. of dock with electric & water, outstanding views of Snake Creek, 3 separate garages, batting cage, workshop, storage galore, gated entrance, & generator located in beautiful Venetian Shores. This one of a kind home has it all!

305  North Drive  For Sale, MLS 582775
$1,195,000
Plantation Key
Plantation Lake Estates   - MM: 87.00
3 Bed, 3 Baths, 2,345 SqFt Days Listed: 469
-7.72% ($100,000) 1 Price Change : Last Change 357 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 68ft.

Tucked away in the exclusive Plantation Lake Estates private and gated community, this 3B/3B, immaculate gem is the perfect island retreat. This impressive, Islamorada garden house is situated in the most tranquil setting with expansive lake-front views from all levels, including the expansive Widows Walk. Deep-water dockage, straight shot out to the open ocean, plus easy access to the bay via Snake Creek. 2B/2B, plus loft upstairs and a full 1B/1B plus kitchenette downstairs. Storage galore inside and outside. House is set up to receive generator power. Included in the real property sale price are the bromeliads, all of the orchid collection and all staghorn ferns attached to trees.

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!

134  Milano Drive  For Sale, MLS 587406
$1,995,000
Plantation Key
Venetian Shores   - MM: 86.00
5 Bed, 5 Baths, 3,576 SqFt Days Listed: 157
-7.17% ($154,000) 1 Price Change : Last Change 96 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift100ft.Concr

Islamorada Venetian Shores 5BD/5BA with 100 dock and boat lift! This one has it all including a custom pool with spa and waterfall, elevator to all three floors and a totally private master suite on the 3rd floor with side den/office. On the ground floor is an elegant entry foyer and a spacious 1/1 guest apartment (above flood), plus a large garage and poolside cabana room. Enjoy Instant big boat access to both the ocean and bay from 100 wide, deep canal. Spacious home offers over 5,000 sf including porches, separate guest quarters and garage. There are booked rentals already in place and the house has a strong rental history to help offset costs. New flooring, camera system, brick driveway, impact glass, landscaping and more!

189  Sunset Drive  For Sale, MLS 585442
$1,350,000
Lower Matecumbe
Lower Mat Beach   - MM: 74.00
2 Bed, 2 Baths, 1,040 SqFt Days Listed: 301
-6.90% ($100,000) 2 Price Changes : Last Change 42 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.

158  Key Heights Drive  For Sale, MLS 588557
$7,900,000
Plantation Key
Key Heights   - MM: 88.50
5 Bed, 5 Baths, 6,183 SqFt Days Listed: 81
+6.84% ($506,000) 1 Price Change : Last Change 58 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Basin,Boat Lift,Boat

Only the finest of materials, appliances, whole house systems and true attention to detail make up this custom-built bayfront estate which exemplifies all the best in quality home construction. Enjoy sweeping open water views and unequaled casual Keys living from the security and comfort of expansive spaces set with a classic understated design. Amenities include: Vaulted ceilings of Yellow Alaskan Cedar Spanish Limestone floors Large screen theater/media room Gym Grand master suite with private balcony Two guest suites Two den/office spaces (both can be utilized as addl bedrooms) Solid maple cabinetry Wolfe & Subzero Appliances Multi-head shower systems Mahogany interior doors Security system Anderson impact/insulated windows

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

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