Upper Matecumbe Key Islamorada Homes for Sale, Single Family Houses, MLS Home Listings

Homes for sale in Upper Matecumbe are highly in demand, greater still as a part of the larger area known as Islamorada.  Islamorada is known for its superior off-shore fishing, large assortment of restaurants, and great areas for shopping - and Florida Keys real estate buyers looking at Upper Matecumbe houses have access to all this and more.  Upper Matecumbe Key properties are often located waterfront, and are typically characterized by a unique Florida Keys charm.  See all MLS listings of houses for sale in Upper Matecumbe Key Islamorada below.

Total Listings 12
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.

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.

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.

82762  Overseas Highway 4 For Sale, MLS 582266
$925,000
Upper Matecumbe Key Islamorada
Madeira Bay   - MM: 82.50
3 Bed, 3 Baths, 1,956 SqFt Days Listed: 368
-2.63% ($25,000) 1 Price Change : Last Change 147 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Boat Ramp,

BAY VIEWS & BOAT SLIP IN ISLAMORADA! Waterfront gated enclave of 8 single family homes in Madeira Bay centrally located in the heart of Upper Matecumbe Key. Tri-level 3B/2B residence just one home off the bay, nice water views plus dedicated boat slip w/boat lift directly on Florida Bay. Open floor plan, vaulted ceilings, tiled floors, 2 central ac units, multiple sliding glass doors to bayside patios on both living levels. Ground floor offers carport, above flood guest quarters of 304 SqFt, large sundeck, low maintenance yard with lots of native foliage. Common areas include gated entry, pool, boat ramp & dock. Enjoy this unique peaceful location/setting in the Village of Islands.

117  Seashore Drive  For Sale, MLS 586735
$959,000
Upper Matecumbe Key Islamorada
Green Turtle Beach   - MM: 81.20
3 Bed, 3 Baths, 2,624 SqFt Days Listed: 75
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

The Tamarind House... Youll enjoy this family style residence and the island life in this expansive 2,624s.f. Florida Keys home. Located in a quiet, serene area of Islamorada, just a few blocks to all the restaurants, galleries, and boutiques you might want to keep you entertained. With a double carport and workshop on the ground floor, youll have plenty of parking and storage. The second floor features a spacious, open floor plan kitchen, bar, dining and living room with soaring ceilings! A nice walk-in shelved pantry closet is also part of the kitchen. To complete the main floor there are two guest bedrooms each with walk in closets, that share a large laundry room and a full bathroom.The third floor very private master is custom designed to provide a quiet refuge, along

81906  Overseas Highway  5 For Sale, MLS 580100
$1,150,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
3 Bed, 3 Baths, 1,852 SqFt Days Listed: 525
+4.55% ($50,000) 1 Price Change : Last Change 132 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Basin

NEW CONSTRUCTION. CORAL COVE an intimate gated community of 9 site-built homes in the heart of downtown Islamorada. Bayfront with boat basin and dock, each home has its own private pool, state of the art amenities and details plus light and bright natural stone and wood finishes and just steps away from all that Islamorada has to offer.Developers are FL licensed real estate agents.

82994  Overseas Highway 23 For Sale, MLS 579971
$2,799,000
Upper Matecumbe Key Islamorada
Penn Key Club   - MM: 83.00
3 Bed, 3 Baths, 1,812 SqFt Days Listed: 532
-20.03% ($701,000) 4 Price Changes : Last Change 20 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!

80531  Old Highway  For Sale, MLS 584600
$3,650,000
Upper Matecumbe Key Islamorada
Unplatted Upper Mate   - MM: 82.00
3 Bed, 3 Baths, 2,044 SqFt Days Listed: 225
-5.66% ($219,000) 1 Price Change : Last Change 161 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None,Other DockageCo

A one-of-a-kind 4.33-acre estate on Upper Matecumbe Key. Enter the gate and follow the classic brick driveway to one of Islamoradas most private settings. The main house, which is 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.

200  Atlantic Street  For Sale, MLS 579361
$7,900,000
Upper Matecumbe Key Islamorada
Misc Upper Matacumbe   - MM: 82.00
8 Bed, 8 Baths, 4,744 SqFt Days Listed: 573
-1.25% ($100,000) 1 Price Change : Last Change 377 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

Bunny Key, a premiere historic Islamorada oceanfront plantation. It has been over two decades since this property has been available. Known by its provenance that starts as the LaBranche Fishing Camp in 1937, where it is said the owner and author penned many a fishing tale with the ocean as his muse and passion for fly fishing as his motivation. Once you enter the gate you will be entranced by the prettiest beach on the island of Islamorada with an estimated 240 feet lining the Atlantic ocean. The main home and guest wing of 3 bedrooms radiate character at every corner, reminiscent of a time gone by with the inviting Old Florida porch stepping out on to the beach. The Kitchen is lined in custom Pecky Cypress cabinets and stone counters which blends beautifully with the Dade County

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: 144
-11.76% ($2,000,000) 1 Price Change : Last Change 11 Days Ago
Single Family - 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.

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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