Islamorada Homes for Sale, Single Family Houses, MLS Home Listings

Houses for sale in Islamorada are some of the most highly sought after and prolific in the Florida Keys real estate market.  Islamorada homes are spread out over a relatively large area, including those in Upper and Lower Matecumbe Key, Plantation Key, and Windley Key.  Many are drawn to this area for its abundance of attractions, including popular restaurants and leisure destinations, as well as for the incredible sport fishing in the area.  Its designation as the Sport Fishing Capital of the World makes the waterfront properties for sale in Islamorada even more highly in demand.  See all MLS listings of single family houses for sale in Islamorada below.

Total Listings 95
Order By:

132 N Hammock Road  For Sale, MLS 584607
$425,000
Upper Matecumbe Key Islamorada
Hammock   - MM: 83.50
2 Bed, 2 Baths, 1,569 SqFt Days Listed: 224
-5.35% ($24,000) 1 Price Change : Last Change 90 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

This single family home is located on Upper Matecumbe Key. It is a 2 bedroom 1 bath home with a bonus room perfect for office or workshop. There is an extra large living room and a dining area with vaulted ceiling accented with tongue and groove finish. The kitchen has new refrigerator, stove and dishwasher. There is room for boat and/or trailer storage in the oversize yard which has an established sapodilla tree as well as papaya trees.

110  Knowles Street  For Sale, MLS 586123
$459,000
Upper Matecumbe Key Islamorada
Coral View   - MM: 83.00
3 Bed, 3 Baths, 2,008 SqFt Days Listed: 122
-10.86% ($55,900) 3 Price Changes : Last Change 34 Days Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Charming and spacious 3 bedroom, 2 bath home for sale in the heart of Islamorada. New roof in 2017. Remodeled kitchen and bathrooms. Covered patio with hot tub. Laundry room with plenty of storage. More than meets the eye inside and out. Large lot offers plenty of room to park cars, boats and other toys. Close to shopping, restaurants and parks.

84961  Old Highway 23 For Sale, MLS 587700
$495,000
Windley Key
Galen Beach   - MM: 85.00
2 Bed, 2 Baths, 705 SqFt Days Listed: 4
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Dock Privileges,Othe

Move right into your fully furnished Oceanside Escape....catch the beautiful Florida Keys Sunrises and Ocean Breezes! Located in Windley Key Mobile Home Park Condo. This meticulously maintained newer stilt home offers 2 bedroom and 2 full baths metal roof, impact windows, open porch, carport for two, storage, chickee hut and Chicago brick patio to entertain with tropical landscape. Comes tastefully furnished. Home is built for 180mph wind velocity and has a Transferable Structural Warranty good till 2023. This rare quaint association has 48 units which sits overlooking the Atlantic Ocean. Low Association fees. Amenities include jetty to sit and soak up some Vitamin Sea, fish cleaning station, Marina, Sm boat ramp etc..... Must see!

114  Gumbo Limbo Road  For Sale, MLS 585909
$549,000
Plantation Key
Bay Ridge   - MM: 87.50
3 Bed, 3 Baths, 1,274 SqFt Days Listed: 137
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: Dock Privileges

Warm and inviting three-bedroom, two-bathroom home offering casual elegance with Old Florida style. Built in the late 1960s, nestled under a Gumbo Limbo tree with tropical landscaping, this classic ground-level home in the charming neighborhood of Bay Ridge is waiting for new owners. The Bay Ridge community is known for its homeowners marina and pool, and is centrally located bayside on Plantation Key. Many unique features of this home include a ballast stone accent wall made from local wrecks, a separate spacious garage, a beautiful screened breezeway, and an abundance of natural light cascading over amazing authentic wood floors. This homes appeal is timeless.

100  Coconut Lane  For Sale, MLS 587656
$549,000
Plantation Key
Plantation Beach   - MM: 87.50
2 Bed, 2 Baths, 956 SqFt Days Listed: 7
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: Boat Ramp,Other Dock

Coconut Lane....... This 2014 custom CBS home is in exclusive Plantation Beach, Islamorada.... a quiet residential area. The home sits on the western side of the island within a short walk to the private homeowners beach and park. This two bedroom two bath home has custom hardwoods, a granite-stainless steel kitchen, custom tile, high ceilings, impact windows, doors and a spacious great room. Enjoy the large and private back yard garden from the 400 sq. ft. of screened in patio and entertainment area. The native and lush tropical landscaping on this 10,500 sq. ft. lot adds a lot of natural privacy and great ambience as you enter the driveway. Launch your boat from the private park ramp and watch the sunset on Floridas Bay every night!

102  Jerome Avenue  For Sale, MLS 587676
$595,000
Upper Matecumbe Key Islamorada
Grove Park   - MM: 81.50
3 Bed, 3 Baths, 1,344 SqFt Days Listed: 5
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

nice ground level home on a quiet and shady lot in the heart of Islamorada, X flood zone, great neighborhood, walking distance to great restaurants and shopping, close to fishing and diving charters, double car garage gives plenty of storage, screened entertainment & relaxation area provides nice outdoor sitting space, tile throughout, fresh paint inside & outside, vaulted ceilings, indoor toilets, breakfast bar, washer & dryer in garage, low maintenance grounds.

168  Iroquois Drive  For Sale, MLS 585437
$665,000
Lower Matecumbe
Lower Mat Beach   - MM: 74.00
3 Bed, 3 Baths, 1,232 SqFt Days Listed: 168
+6.40% ($40,000) 1 Price Change : Last Change 76 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift,Boat Ramp5

This 3 bedroom 2 bath home in the sought after location of Lower Matecumbe in Islamorada boasts over 50 of dockage, 4,000 lb boat lift and a private boat ramp! Immediate access to ocean or bay for all your boating needs! Downstairs storage, covered fish cleaning station and gazebo for shaded entertainment! Home took some damage from the hurricane. Installation of new metal roof has been scheduled along with new flooring to be installed. Great opportunity to own a home in the Florida Keys! Easy to show! Option to purchase with adjacent lot at 172 Iroquois Dr. for $1,050,000.

133  Royal Lane  For Sale, MLS 586148
$669,000
Plantation Key
Plantation Beach   - MM: 87.50
3 Bed, 3 Baths, 2,450 SqFt Days Listed: 120
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

If youre looking for a Solid Place to start your future in the Fabulous Florida Key look no further. This home was built by a Concrete Contractor for himself, and it Passed with Flying Colors during Irma. Great Elevation X Zone with wonderful interior trimming such as Ceder, and a Hickory Cabinet Kitchen to boot. This home makes you feel like your home; and you basically have a whole other house downstairs for Friends, Family, and those unexpected guests that always pop in LOL. Other Bonuses like being right around the Corner from Founders Park, and just minutes away from a multitude of activities, make this centrally located home even more attractive; an the only traffic you will see 99% of the time is just your neighbors. Cant Beat That!

203  Dogwood Lane  For Sale, MLS 584311
$674,900
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
2 Bed, 2 Baths, 1,682 SqFt Days Listed: 243
-9.89% ($74,100) 3 Price Changes : Last Change 155 Days Ago
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Move in before the Holidays! Historical beautifully restored Conch house in the Heart of Islamorada! Restored like new along with rare Old Florida ambiance. President George W. Bush would visit and dine here after fishing with former owner Capt. George Hommel! House is about 100 from open ocean beach, fenced yard, tropical landscaping, 3-4 car pavered parking. Restoration (2 years ago) includes metal roof, impact windows and doors, all new high efficiency split mini A/C, new high end exceptional kitchen and appliances, lighting. Quartz counters, big pantry! New 2blinds, drapes. Huge Florida/Bonus room, screened porch, pergola, large CBS workshop! Rubberized exterior paint. Close to Discovery Center, Islander Resort, restaurants, boutiques. Owner is real estate agent.

81212  Old Highway  For Sale, MLS 586288
$699,000
Upper Matecumbe Key Islamorada
Misc Upper Matacumbe   - MM: 81.20
2 Bed, 2 Baths, 728 SqFt Days Listed: 111
-17.76% ($151,000) 2 Price Changes : Last Change 31 Days Ago
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Mango House... A magical, modern, Island-style Villa with the ideal location! This newly renovated Villa features 2 bedrooms, 2.5 baths, and a custom pool featuring a private lounging beach. Located conveniently on the Old Road at Mile Marker 81.2 and just a walk or golf cart ride to all the restaurants, breweries, and boutiques on Morada Way and Upper Matecumbe Key. Originally built in 1961, this home is NEW from the ground up, and features brand new appliances, electrical, plumbing, windows, doors and more, but still keeps its 1960s design and charm.

129  San Marco Drive  For Sale, MLS 586261
$729,000
Plantation Key
Venetian Shores   - MM: 86.00
3 Bed, 3 Baths, 1,400 SqFt Days Listed: 113
-8.76% ($70,000) 3 Price Changes : Last Change 1 Day Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Assigned Dock,Basin,

Turn Key waterfront 3/2 concrete home in sought after neighborhood of Venetian Shores. Included in the sale is boat slip #14 in Marina which holds upto a 40ft boat. Open floor plan, SS appliances and granite countertops in kitchen. Vaulted ceiling in Kitchen and living room make room spacious and open. Large waterfront screened porch with french doors on waterside. Downstairs has large enclosed storage area, covered seating/lounge area and bbq. Pool plans have been approved...This property has a vacation rental history as well, to help offset cost.A MIUST SEE!! Least expensive property in the neighborhood!! MOTIVATED SELLERS

104  Anglers Way  For Sale, MLS 585447
$735,000
Windley Key
Anglers Reef   - MM: 85.00
2 Bed, 2 Baths, 1,376 SqFt Days Listed: 167
-1.34% ($10,000) 1 Price Change : Last Change 17 Days Ago
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None,Other Dockage

Islamorada conch style home at Anglers Reef now available. 2 bedrooms, each with full bathroom and balconies; living areas and kitchen w/half bath on main level. Stay as many days as you wish and rent it when youre not in town. Qualifies for 7-day minimum vacation rental license and has strong vacation rental history; making this an excellent investment opportunity. Tropically landscaped and gated community of 52 single family homes offers heated pool with two beach areas. Anglers Reefs oceanfront marina with 35 slips, some available to rent weekly or longer. Conveniently situated between Miami and Key West airports. Prime Florida Keys location near restaurants, boutique shopping, art galleries and world class sportfishing. Paddleboard, kayak, snorkel, dive and relax from this retreat.

179  Azalea Street  For Sale, MLS 587253
$749,000
Plantation Key
Plantation Key Colony   - MM: 90.00
4 Bed, 4 Baths, 1,761 SqFt Days Listed: 36
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 50ft.Concrete

Price reduced on this 4 bedroom 4 bathroom all concrete canal front home in Plantation Key Colony. The upstairs is a 2/2. Tiled throughout this open floor plan with all wood kitchen cabinets overlooking the canal with a 24 x 8 screened in porch. There is a spiral staircase leading to the concrete roof top and concrete walk way around a majority of the second floor. One of the few legal downstairs consisting of a 2/1 apartment , an efficiency and a large storage area with Washer and Dryer. All of the downstairs is wheelchair accessible via concrete walkways to driveways. Ceiling fans in all rooms. Aluminum windows (awning and single hung). All concrete 50 dock on a wide free flowing canal which never accumulates seagrass. Ready for immediate occupancy. Call today this one wont last.

131  Anglers Way  For Sale, MLS 587606
$749,999
Windley Key
Anglers Reef   - MM: 85.00
2 Bed, 2 Baths, 1,167 SqFt Days Listed: 9
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: Other Dockage

Anglers Reef, priced to sell! Islamoradas Upscale Oceanfront Gated Community, This home features 2 bedrooms, 2.5 bathrooms with 2 private carports and 4 porches with some water views. Upgrades include hardwood floors, kitchen with granite countertops and SS appliances with breakfast bar and lots of cabinet space, impact doors & windows, freshly painted inside and outside. The community features a private beach, pool and marina on the Atlantic Ocean. Home has been in rental program for over 5 years. Own your vacation home for free and more. Great investment. Dock Slip can be purchased at an additional price.

116  Galleon Road  For Sale, MLS 586561
$785,000
Plantation Key
Treasure Harbor   - MM: 86.50
4 Bed, 4 Baths, 2,915 SqFt Days Listed: 88
-1.26% ($10,000) 1 Price Change : Last Change 8 Days Ago
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Extremely well maintained all concrete 4 bedroom, 2.5 bath pool home. Down stairs offers a massive garage with plenty of room for 2 or 3 cars and your boat and personal water crafts. Impact sliders lead out to the covered lanai pool area with a very private rear yard. (No neighbors behind you.) Come up the solid concrete stairway to a huge great room with souring ceilings and cupola. Ceramic tile and laminate wood flooring through out. Large kitchen with wood cabinets, granite tops and stainless appliances. There is a large master suite with walk in closet and large master bath with granite tops, large roman tub and separate shower. Bedroom three and four share a Jack and Jill bathroom. Large screened porch over looking the pool and private mangrove rear yard. Lots of wild life to observe

77340  Overseas Highway  For Sale, MLS 587336
$799,000
Lower Matecumbe
Matecumbe Ocean Bay   - MM: 77.00
2 Bed, 2 Baths, 928 SqFt Days Listed: 29
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Concrete

Perfect opportunity to build your dream home in the Florida Keys, Village of Islamorada. Adjacent buildable lots on either side available For Sale for a total of 102,802Sq.Ft. to build your dream family compound (lots are listed for sale altogether or each individually- see Listing #587337 - Lot 4, 5 & 6/587338 - Lot 4/587339 - Lot 6). Property is on the Bay Side next to Robbies, just minutes to Tea Table and access to ocean.

122  South Drive  For Sale, MLS 584620
$805,000
Plantation Key
Plantation Lake Estates   - MM: 87.00
3 Bed, 3 Baths, 2,300 SqFt Days Listed: 224
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: Boat Ramp,Dock Privi

Location, location! Plantation Lake Estates is a super desirable gated community directly across from Islamoradas Founders Park. This concrete 3BD/3BA home has it all with a concrete roof, impact windows, a huge ocean view concrete rooftop deck, updated kitchen & baths, private top floor custom master suite, whole house automatic generator, new 3.5 ton central A/C, 2 garages & a large separate workshop. The neighborhood also has a private boat ramp with immediate ocean access plus temporary dockage. Founders Park, the central city-owned park across the street, offers a sandy bayfront beach, playground, sports fields, tennis courts, Olympic pool and dive complex, amphitheater and fair grounds for community festivals & events. Must see to appreciate... call today!

100  Venetian Drive  For Sale, MLS 586439
$875,000
Lower Matecumbe
White Marlin Beach   - MM: 74.50
2 Bed, 2 Baths, 1,080 SqFt Days Listed: 97
-1.69% ($15,000) 1 Price Change : Last Change 49 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.

132  San Marco Drive  For Sale, MLS 586416
$899,000
Plantation Key
Venetian Shores   - MM: 86.00
5 Bed, 5 Baths, 2,447 SqFt Days Listed: 99
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Boat Slip

This spectacular two-story home in Venetian Shores on Plantation Key is modern and spacious.Move-in ready property includes 3bedrooms/ 2baths upstairs with 2 bedroom/1 bath guest suite downstairs. Enjoy an open floor plan with an updated eat in kitchen, wood cabinetry and granite countertops. The large master en-suite includes a walk-in closet and stunning water views. Other features spotlight a spa, a separate laundry room, screened in porches, impact resistant windows and metal roof. This offering includes an assigned boat slip #20 with lift in Venetian Shores Yachting Association Marina. Relax in your private backyard with enough room to add a pool.

136  Anglers Way  For Sale, MLS 583979
$899,999
Windley Key
Anglers Reef   - MM: 85.00
2 Bed, 2 Baths, 1,314 SqFt Days Listed: 260
-14.29% ($150,001) 1 Price Change : Last Change 12 Days Ago
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: Other Dockage

Looking for a second home that pays for itself? Or an investment property with an even higher return? This beautiful home situated in Islamorada, better known as Village of the Islands, can be purchased with as little as $262.5k down & less than $6k a month while generating rental income to offset the mortgage payments. All rental numbers can be verified along with supplying the new owner & entire roadmap on how to maximize their return while owning a piece of paradise.Live the world famous tropical lifestyle and fish for dinner half of the year, cover your mortgage by charging others to enjoy the same experience the other half!Located in Angers Reef. Remodeled 2/3 home has 2 carports, ocean views & lots of upgrades. The Community has 2 sandy beaches, community pool & Docks

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 10-14-2019.

Shoreline Properties
92300 Overseas Hwy Suite 303
Key Largo, Florida 33070

1(800) 692-3605
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