Upper Matecumbe Key Islamorada Waterfront Homes, Condos, and Properties for Sale, Florida Keys Real Estate

Total Listings 20
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79901  Overseas Highway 416 For Sale, MLS 588574
$979,900
Upper Matecumbe Key Islamorada
Palms Of Isla   - MM: 80.00
3 Bed, 3 Baths, 1,484 SqFt Days Listed: 4
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

Breathtaking Ocean views from this 3 bedroom 2 bath unit that is centrally located in Islamorada at The Palms of Islamorada. You have floor to ceiling windows that provide spectacular ocean views from the Livingroom, Kitchen, master bedroom and guest bedroom with panoramic ocean views from the large private open terrace. All 3 bedrooms have walk-in closets and closets throughout the condo for plenty of storage space. Kitchen has wood cabinets, granite countertops with stainless steel appliances and 2 ovens that come in handy when entertaining. Some of the many features of the gated complex are covered parking, ocean front pool and spa, tiki hut, gym, clubhouse with kitchen and a kayak launch with storage rack. Steps away from Bud and Marys for all of your boating needs.

81801  Overseas Highway 617 For Sale, MLS 588546
$425,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
1 Bed, 1 Baths, 681 SqFt Days Listed: 5
Condotel - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Dock Privileges

Location makes this King Suite with kitchenette at the historic Cheeca Lodge & Spa the exception. Palm trees and tropical landscape surrounds this top level unit creating a private oasis. Steps from the new beachfront pool and tiki bar this luxury unit has direct views of the crystal clear lagoon with island waterfall. Relax in the inviting soaking tub encompassed by beautiful marble after a day spent on the beach. Enjoy a glass of wine on the private screened porch with the calming sounds of the waterfall in the background. The suite features well appointed furnishings, a plush king bed, and a sleeper sofa for additional sleeping. This is an income producing property allowing 28 fabulous owner days! Cheeca handles all vacation rentals making your investment hassle free. Cheeca offers a

79901  Overseas Highway 507 For Sale, MLS 588507
$470,000
Upper Matecumbe Key Islamorada
Palms Of Isla   - MM: 80.00
2 Bed, 2 Baths, 981 SqFt Days Listed: 7
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat RampConcrete

Oceanfront, Top Floor, Completely Renovated 2 Bedroom, 2 Bath Condo Unit at The Palms of Islamorada. All the work has been done, no need for the expensive and timely pain of a condo remodel. New kitchen and baths, new windows and shutters, new AC and hot water heater. The complex features an oceanfront pool and hot tub, a relaxing beach, his and hers gyms, an outdoor grill and tiki area, kayak/SUP launch ramp and gorgeous open-water views of Alligator Lighthouse and Terra Key. The Palms is conveniently located near Lazy Days Restaurant, Midway Cafe and Coffee Bar, Amara Cay Resort and Bud n Marys Marina. Downtown Islamorada, offers a wide array of restaurants and shops and is less than a mile away.

80221  Overseas Highway  For Sale, MLS 588502
$5,700,000
Upper Matecumbe Key Islamorada
Unplatted Upper Mate   - MM: 81.20
4 Bed, 4 Baths, 3,195 SqFt Days Listed: 8
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

COCOMOS is a picturesque, and tropical, island retreat, on a beautiful 3-acre ocean-front estate, just a short walk away from the art district in Islamorada. This property is secluded with a private, electronically gated entry. Outdoor amenities include 250 of pristine sandy beach, pool with waterfall and ocean-front pool deck, outdoor shower, huge furnished Chickee with full summer kitchen, new dock, pond, great lawn and lush landscaping. The main house hosts 3 bedrooms and 3 baths with two living rooms and two kitchens. The guest house hosts 2 queen beds, a sleeper sofa, kitchen, bath and 2 ocean-front patios.

83201  Old Highway 202 For Sale, MLS 588355
$565,000
Upper Matecumbe Key Islamorada
Beacon Reef   - MM: 83.00
2 Bed, 2 Baths, 1,275 SqFt Days Listed: 19
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Assigned Dock,Boat S

Downtown Islamorada 2/2 ocean view condo with great dockage, resort-style pool, coveted covered parking space directly below the unit, and the best location by land or sea! Great boating location for fishing and diving within view of Aliigator Lighthouse and the Islamorada Sandbar. Walking/biking distance to fine dining, shopping and all the downtown art festivals and full moon celebrations. This condo is on the second floor so it has a private walk-down staircase off the back porch to quickly access the pool and dock. It is also an end unit so it has three extra windows (one in each bathroom and one in the master) and all the windows and sliding doors are all updated to impact glass. The baths are both updated as well. Best priced condo in Beacon Reef!

83257  Old Highway  For Sale, MLS 588229
$2,500,000
Upper Matecumbe Key Islamorada
The Russell Estates   - MM: 83.50
5 Bed, 5 Baths, 3,000 SqFt Days Listed: 27
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 pottery studio & or huge 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.

80639  Old Hwy Highway 201 For Sale, MLS 588059
$3,350,000
Upper Matecumbe Key Islamorada
Maison Matecumbe   - MM: 81.00
4 Bed, 4 Baths, 3,274 SqFt Days Listed: 36
+3.08% ($100,000) 1 Price Change : Last Change 32 Days Ago
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Other Dockage155ft.

Nestled in tranquil bay overlooking Alligator Reef, in the heart of Islamorada, Maison Residences offers the only 4-bedroom condominiums in Islamorada. A rare opportunity to own in a luxurious community featuring its own private white sandy beach and a 155 Day Dock. At only a 90 minute drive from Miami, this remarkable paradise offers the perfect playscape for swimming, boating, fishing and more. Resort style pool and spa can be viewed from the oversized living terrace. Just a short distance from the islands finest restaurant, parks and marinas, this quiet, private and gated community brings a new standard of living to The Florida Keys. Pre-construction in final phase with expected date of delivery end of 2020. ADA Compliant, Smart home, 10 Ceilings and more.

82762  Overseas Highway 4 For Sale, MLS 588011
$925,000
Upper Matecumbe Key Islamorada
Madeira Bay   - MM: 82.50
3 Bed, 3 Baths, 1,956 SqFt Days Listed: 40
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Ramp,Boat Slip,

WATERFRONT GATED ENCLAVE IN ISLAMORADA! Enjoy partial bayviews and your own dedicated boat slip directly on Florida Bay. This tri-level 3B/2B home is located just one home off Florida Bay on Upper Matecumbe Key in Madeira Bay, a gated community of only 8 single family residences with shared pool & dock. Open floor plan with vaulted ceilings, tiled floors, multiple sliding glass doors to decks on both living levels. Ground level enclosure is above base flood and permitted living area w/plumbing for bathroom. Truly a must see property to appreciate this unique setting with a Bayview & Dockage!

83201  Old Highway 205 For Sale, MLS 587914
$695,000
Upper Matecumbe Key Islamorada
Beacon Reef   - MM: 83.00
2 Bed, 2 Baths, 1,275 SqFt Days Listed: 46
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Assigned Dock,Dock P

Updated Oceanfront 2/2 Condo with Ocean Views & Dockage! This is the downtown Islamorada condo youve been waiting for with nothing left to do! Elegantly updated kitchen, updated flooring, updated baths and fully furnished and offered turn key so its ready to move right into and enjoy! Step out on to your private balcony and take your private spiral stairs directly to the pool gate! Going boating? Take the spiral stairs down to your storage closet, grab your poles and go! Beacon Reefs one-of-a-kind dock features step-down finger piers for easy loading for any size boat up to 38 ft. with power, water and even ice at the end of the dock! Ocean view gym, clubhouse, beach-entry pool w/oversized hot tub and high-end tropical landscaping make this condo feel like a premier luxury resort!

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: 51
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,

81801  Overseas Highway 735 For Sale, MLS 586656
$339,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
1 Bed, 1 Baths, 358 SqFt Days Listed: 138
Condotel - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

Here is your chance to own a great, income-producing piece of the iconic Cheeca Lodge & Spa in the heart of Islamorada. This beautiful double queen bedded resort view room is a great investment and can be your vacation spot for up to 28 days per year! Cheeca has long been the resort of choice for families, romantic getaways and more than one President. You will have your choice of 3 great restaurants, 2 bars, 2 pools (with a 3rd coming soon), 6 lighted tennis courts, a 9-hole, par 3 golf course, a Spa and workout facility, along with Camp Cheeca for kids. This unit has experienced over 80% occupancy and offers a great return on investment.

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: 201
-11.76% ($2,000,000) 1 Price Change : Last Change 68 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.

83201  Old Highway 422 For Sale, MLS 585352
$850,000
Upper Matecumbe Key Islamorada
Beacon Reef   - MM: 83.00
2 Bed, 2 Baths, 1,275 SqFt Days Listed: 231
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Assigned Dock,Boat S

What a View! Rare 2/2 condo with an expansive full ocean view from the minute you open the door! This direct oceanfront residence in beautiful Beacon Reef offers a front row view of the deep blue Atlantic, Alligator Lighthouse and Beacon Reefs one-of-a-kind dock complete with tiki hut and lovely evening lighting. Move-in ready with updated kitchen and baths PLUS a coveted covered parking spot to tandem park two cars or keep your boat/trailer onsite. Beacon Reef is located in downtown Islamorada near everything by land or sea. By boat, the Islamorada sandbar is minutes away along with great fishing and diving. By land, the new Publix is across the street and downtown is less than a mile away with fine dining, shopping, events and local nightlife. Resort-style pool, spa, gym & more!

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: 282
-5.66% ($219,000) 1 Price Change : Last Change 218 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.

83201  Old Highway 221 For Sale, MLS 584344
$775,000
Upper Matecumbe Key Islamorada
Beacon Reef   - MM: 83.00
2 Bed, 2 Baths, 1,275 SqFt Days Listed: 298
-4.91% ($40,000) 1 Price Change : Last Change 235 Days Ago
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: First Come Dock36ft.

Exquisite direct oceanfront condo in the luxury community of Beacon Reef and located directly on the beach. Walk down your private exterior stairs and you are right on the most beautiful sandy beach in Islamorada. This is the Florida Keys condo with the ocean views and beach you have been dreaming of. The condo offers 2 bedrooms, 2 baths, renovated kitchen and bathrooms, gorgeous balcony, Jacuzzi tub, plenty of closet space, and new appliances. 5 star community amenities include sandy beach, boat dockage, zero-entry pool and hot tub, pier with seating and fishing stations, clubhouse and fitness center with ocean views & poolside tiki hut with grills.

80639  Old Highway 302 For Sale, MLS 581214
$1,185,000
Upper Matecumbe Key Islamorada
Maison Matecumbe   - MM: 81.00
3 Bed, 3 Baths, 1,946 SqFt Days Listed: 504
-15.05% ($210,000) 2 Price Changes : Last Change 77 Days Ago
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

Exclusive gated oceanfront condo in the heart of Islamorada. This one-story residence offers three bedrooms and two bathrooms, and is in turnkey condition. The property also has covered parking and an excellent rental history. Amenities include a sandy beach, a beautiful new pool, and a convenient location near shops, dining, the Arts District, and marinas that will book fishing and diving excursions.

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: 582
+4.55% ($50,000) 1 Price Change : Last Change 189 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: 589
-20.03% ($701,000) 4 Price Changes : Last Change 77 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!

79901  Overseas Highway 515 For Sale, MLS 578881
$1,195,000
Upper Matecumbe Key Islamorada
Palms Of Isla   - MM: 80.00
3 Bed, 3 Baths, 1,484 SqFt Days Listed: 657
-14.34% ($200,000) 1 Price Change : Last Change 54 Days Ago
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

Beautifully renovated 3 bedroom condominium in the Palms of Islamorada. Top floor end unit in southerly building with open ocean views. Walk to fine dining, great fishing boats, both offshore & back country, and a great diving/snorkeling operation. Large private balcony with view of Alligator Light. Unit has been converted to 2 bedroom but will be returned to 3 bedroom if Buyer desires.

79901  Overseas Highway 205 For Sale, MLS 578165
$599,000
Upper Matecumbe Key Islamorada
Palms Of Isla   - MM: 80.00
2 Bed, 2 Baths, 981 SqFt Days Listed: 700
+20.04% ($100,000) 2 Price Changes : Last Change 54 Days Ago
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

Beautifully renovated 2 bedroom condominium in the Palms of Islamorada, walk to fine dining, great fishing boats, both offshore and back country, and a great diving/snorkeling operation. Total restoration down to the studs including new wiring, plumbing, walls, flooring, and ceilings. Offered completely furnished with all amenities TVs, new appliances including washer/dryer. Ready to enjoy starting the day of closing.

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 12-10-2019.

Broker's Edge Realty
92300 Overseas Hwy Suite 303
Key Largo, Florida 33070

1(800) 692-3605
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