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Strattons Homes for Sale, Upper Matecumbe Islamorada, Florida Keys

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Total Listings 14
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81801  Overseas Highway 731 For Sale, MLS 587846
$315,000
Upper Matecumbe Key Islamorada
Strattons - MM: 82.50
1 Bed, 1 Baths, 380 SqFt Days Listed: 256
Condotel - Active - Waterfront No
Side of Island: Ocean - Dockage: Dock Privileges

Welcome to your double queen corner resort room at the historic Cheeca Lodge & Spa. This rare top floor unit features extra high ceilings, two queenbeds, one luxurious bathroom with soaking tub and separate shower. Income producing property allowing 28 fabulous owner days! Cheeca handles all vacation rentals making your investment hassle free. The resort offers a spa, Camp Cheeca for the kids, beachfront pool, 9-hole par 3 golf course, lush gardens, bike path, tennis courts, pickle ball court, fitness center, 5 star dining, tiki bar, beach, dock, water sports, and fishing. COMBINE with UNIT 730 for TOTAL PRICE of $645,000! Cheeca is located in the heart of Islamorada and in walking distanced to shopping, galleries, restaurants, breweries, and island festivities.

81801  Overseas Highway 732 For Sale, MLS 591257
$330,000
Upper Matecumbe Key Islamorada
Strattons - MM: 82.50
1 Bed, 1 Baths, 358 SqFt Days Listed: 19
Condotel - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Dock Privileges

Located in the heart of downtown Islamorada, Cheeca Lodge & Spa. Be a part of a world-class resort, without the worries!! 27 acres of tropical landscaping, 9-hole golf course, pickle ball, tennis courts, 3 heated pools, full array of water sports, fishing pier, private fishing and boat trips, fine and casual dining, 2 tiki bars, concierge, shopping, camp Cheeca for the kids, Lovely spa and fitness facility! Passive Investment Income producing property allowing owner to occupy unit for 28 days yearly!

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: 344
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.

81801  Overseas Highway 730 For Sale, MLS 587845
$355,000
Upper Matecumbe Key Islamorada
Strattons - MM: 81.80
1 Bed, 1 Baths, 550 SqFt Days Listed: 256
Condotel - Active - Waterfront No
Side of Island: Ocean - Dockage: Dock Privileges

Welcome to your King Suite at the historic Cheeca Lodge & Spa. This rare top floor unit features extra high ceilings, one bedroom, one bathroom, and a full kitchen. Income producing property allowing 28 fabulous owner days! Cheeca handles all vacation rentals making your investment hassle free. The resort offers a spa, Camp Cheeca for the kids, beachfront pool, 9-hole par 3 golf course, lush gardens, bike path, tennis courts, pickle ball court, fitness center, 5 star dining, tiki bar, beach, dock, water sports, and fishing. Sleeper sofa in living area for additional sleeping. COMBINE with UNIT 731 for TOTAL PRICE of $645,000! Cheeca is located in the heart of Islamorada and in walking distance to shopping, galleries, restaurants, breweries, and island festivities.

81801  Overseas Highway 750 For Sale, MLS 581494
$419,000
Upper Matecumbe Key Islamorada
Strattons - MM: 82.50
1 Bed, 1 Baths, SqFt Days Listed: 689
-6.89% ($31,000) 1 Price Change : Last Change 342 Days Ago
Condotel - Active - Waterfront No
Side of Island: Ocean - Dockage: Dock Privileges

Excellent opportunity to own this one-of-a-kind suite unit at the locally historic Cheeca Lodge & Spa. Its convenient in-town location means its walking distance to dining, shopping, and entertainment. Enjoy all the resort has to offer. Amenities include a par-three nine-hole golf course, five-star dining, kid-friendly features like Camp Cheeca, a spa, pools, beaches, and so much more.

81801  Overseas Highway 625 For Sale, MLS 585197
$425,000
Upper Matecumbe Key Islamorada
Strattons - MM: 82.50
1 Bed, 1 Baths, SqFt Days Listed: 448
+6.25% ($25,000) 1 Price Change : Last Change 237 Days Ago
Condotel - Active - Waterfront No
Side of Island: Ocean - Dockage: Dock Privileges

Cheeca Lodge & Spa lagoon view king suite. The perfect way to get yourself into the Keys; excellent rental income, turn key-opportunity. Enjoy 5 star dining, beach, spa, pools, 9-hole par 3 golf course, Camp Cheeca for the kids, and so much more! Cheeca Lodge is located Oceanside in the heart of Islamorada and walking distance to Islamoradas famous art district, fine dining and shopping.

81801  Overseas Highway 624 For Sale, MLS 585195
$425,000
Upper Matecumbe Key Islamorada
Strattons - MM: 82.50
1 Bed, 1 Baths, 361 SqFt Days Listed: 448
+6.25% ($25,000) 1 Price Change : Last Change 237 Days Ago
Condotel - Active - Waterfront No
Side of Island: Ocean - Dockage: Dock Privileges

Cheeca Lodge & Spa double queen suite. The perfect way to get yourself into the Keys; excellent rental income, turn key-opportunity. Enjoy 5 star dining, beach, spa, pools, 9-hole par 3 golf course, Camp Cheeca for the kids, and so much more! Cheeca Lodge is located Oceanside in the heart of Islamorada and walking distance to Islamoradas famous art district, fine dining and shopping.

81801  Overseas Highway 621 For Sale, MLS 585196
$425,000
Upper Matecumbe Key Islamorada
Strattons - MM: 82.50
1 Bed, 1 Baths, 550 SqFt Days Listed: 448
+6.25% ($25,000) 1 Price Change : Last Change 237 Days Ago
Condotel - Active - Waterfront No
Side of Island: Ocean - Dockage: Dock Privileges

Cheeca Lodge & Spa king suite with lagoon view! The perfect way to get yourself into the Keys; excellent rental income, turn key-opportunity. Enjoy 5 star dining, beach, spa, pools, 9-hole par 3 golf course, Camp Cheeca for the kids, and so much more! Cheeca Lodge is located Oceanside in the heart of Islamorada and walking distance to Islamoradas famous art district, fine dining and shopping.

82236  Overseas Highway 6 For Sale, MLS 589720
$485,000
Upper Matecumbe Key Islamorada
Strattons - MM: 82.50
2 Bed, 2 Baths, 616 SqFt Days Listed: 144
-1.22% ($6,000) 1 Price Change : Last Change 27 Days Ago
Condo - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Ramp,Boat Slip,

WEEKLY RENTALS W/BOAT DOCKAGE-Great Investment Property with transient zoning license. This Bayside 2 Bedroom 2 Bath Updated Ground Level Condo is located right in the Heart of Islamorada near great restaurants, entertainment, and shopping. Enjoy year round spectacular sunsets! HOA includes Boat Basin, 1 boat slip in Marina to accommodate up to 26 boat for each unit, boat ramp, and storage, plus laundry room in building.

82236  Overseas Highway 7 For Sale, MLS 589722
$485,000
Upper Matecumbe Key Islamorada
Strattons - MM: 82.50
2 Bed, 2 Baths, 616 SqFt Days Listed: 144
-1.22% ($6,000) 1 Price Change : Last Change 27 Days Ago
Condo - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Slip

WEEKLY RENTALS W/BOAT DOCKAGE-Great Investment Property with transient zoning license. This Bayside 2 Bedroom 2 Bath Updated Condo on 2nd Floor is located right in the Heart of Islamorada near great restaurants, entertainment, and shopping. Enjoy year round spectacular sunsets! HOA includes Boat Basin, 1 boat slip in Marina to accommodate up to 26 boat for each unit, boat ramp, and storage, plus laundry room in building.

81801  Overseas Highway 730 & 731 For Sale, MLS 587529
$645,000
Upper Matecumbe Key Islamorada
Strattons - MM: 81.80
2 Bed, 2 Baths, 908 SqFt Days Listed: 278
Condotel - Active - Waterfront No
Side of Island: Ocean - Dockage: Dock Privileges

Welcome to your double unit corner suite at the historic Cheeca Lodge & Spa. This rare top floor unit features extra high ceilings, two bedrooms, two bathrooms, and a full kitchen. Income producing property allowing 28 fabulous owner days! Cheeca handles all vacation rentals making your investment hassle free. The resort offers a spa, Camp Cheeca for the kids, beachfront pool, 9-hole par 3 golf course, lush gardens, bike path, tennis courts, pickle ball court, fitness center, 5 star dining, tiki bar, beach, dock, water sports, and fishing. Sleeper sofa in living area for additional sleeping. Cheeca is located in the heart of Islamorada and in walking distanced to shopping, galleries, restaurants, breweries, and island festivities.

81801  Overseas Highway 742 & 743 For Sale, MLS 590718
$759,000
Upper Matecumbe Key Islamorada
Strattons - MM: 82.50
2 Bed, 2 Baths, 908 SqFt Days Listed: 64
Condotel - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Dock Privileges

World Famous Cheeca Lodge & Spa Resort. Premier Income Producing Unit , approximately 50k a year. Only One of four Luxurious 2/2 available. Cheeca handles all vacation rentals making your investment hassle free. 28 exquisite and exclusive days for owners use. Enjoy 5 star dining, beach, spa, pools, 9-hole par 3 golf course, Camp Cheeca for the kids, and so much more!

189  Carroll Street  For Sale, MLS 585953
$1,699,990
Upper Matecumbe Key Islamorada
Strattons - MM: 82.50
5 Bed, 5 Baths, 3,741 SqFt Days Listed: 397
-8.11% ($150,010) 2 Price Changes : Last Change 41 Days Ago
Multi-Units - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Two homes on one lot zoned multi-family. Selling as one package, (189 & 191). Homes are tenant occupied. The total rent roll is $4,800, (below market rate). 189 Carroll Street is a three-bedroom, two-bathroom residence, featuring tile and bamboo flooring throughout, with partial ocean views from the upstairs patio. The spacious master bedroom offers a large walk-in closet. Other features include cultured marble countertops in all the bathrooms, Moen fixtures, American Standard sinks and tub, and a 14-foot-by-10-foot patio off the dining and living rooms. 200-amp electrical box and nice landscaping in place. 191 Carroll Street offers some water views, three master bedrooms, and three bathrooms with a large patio off the first-floor master. Same additional features as 189 Carroll Street.

209 E Carroll Street  For Sale, MLS 590112
$7,900,000
Upper Matecumbe Key Islamorada
Strattons - MM: 82.50
8 Bed, 8 Baths, 4,931 SqFt Days Listed: 122
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

FairWinds~A unique two acre oceanfront estate, discretely situated in downtown Islamorada on Upper Matecumbe Key. FairWinds reflects elegance, beauty, seclusion, along with many amenities. Inside the gates are enchantingly lush tropical gardens with carefully cultivated native specimens leading to the shimmering pastel blues of the Atlantic ocean, which gently caresses the 250+ feet of secluded sandy beach. This very special compound blends privacy with abundant recreational opportunities, ideally suited to create cherished memories with family and friends. FairWinds offers a grand main house, complete with a wrap-around porch, wide verandas and stunning ocean views, perfect for memorable gatherings of family and friends. Watch the sun rise beyond the historic Alligator Reef Lighthouse

Most Recent Sales - (24) - Strattons as of 2020-07-03
Sale Date Address Sale Price $/SF List Price Sq. Ft. Type Bd/Ba Days Listed
05-21-2020 81906 Overseas Highway 6 $1,200,000 $647 $1,250,000 1,852 Single Family 3/3 745
05-01-2020 116 Madeira $1,062,500 $340 $1,350,000 3,120 Multi-Units 6/4 107
04-17-2020 81906 Overseas Highway 4 $1,000,000 $539 $1,050,000 1,852 Single Family 3/3 711
02-28-2020 81906 Overseas Highway 3 $900,000 $502 $900,000 1,790 Single Family 3/3 662
02-28-2020 81906 Overseas Highway 5 $1,090,000 $588 $1,150,000 1,852 Single Family 3/3 662
02-24-2020 81906 Overseas Highway 2 $850,000 $474 $850,000 1,790 Single Family 3/3 658
01-21-2020 81801 Overseas 617 $385,000 $565 $425,000 681 Condotel 1/1 47
12-18-2019 183 Carroll $1,300,000 $1,031 $1,400,000 1,260 Single Family 2/1 64
12-03-2019 203 Dogwood $632,500 $376 $674,900 1,682 Single Family 2/2 293
09-03-2019 81975 Old $400,000 $400 $435,000 1,000 Single Family 2/2 105
07-31-2019 128 Madeira $4,500,000 $1,327 $4,750,000 3,389 Single Family 4/4 269
07-24-2019 81801 Overseas 637 $380,000 $690 $395,000 550 Condotel 1/1 146
07-15-2019 154 Carroll $899,000 $334 $995,000 2,685 Single Family 4/4 242
06-26-2019 81801 Overseas 737 $310,000 $563 $350,000 550 Condotel 1/1 206
05-28-2019 211 Carroll $462,500 $600 $525,000 770 Single Family 2/1 352
05-28-2019 204 Dogwood $462,500 $529 $535,000 873 Single Family 1/1 294
04-05-2019 81801 Overseas 714 $360,000 $654 $399,000 550 Condotel 1/1 641
04-04-2019 81801 OVERSEAS 633 $380,000 $479,000 Condotel 1/1 90
03-07-2019 81641 Old $1,050,000 $480 $1,100,000 2,184 Multi-Units 2/1 108
02-26-2019 115 Carroll $510,000 $657 $579,000 776 Single Family 4/2 148
02-22-2019 127 Madeira $305,000 $286 $299,000 1,064 Single Family 2/1 40
01-10-2019 81801 Overseas 617 $390,000 $572 $430,000 681 Condotel 1/1 79
07-20-2018 81910 Overseas $1,150,000 $597 $1,150,000 1,925 Multi-Units 3/3 1
07-10-2018 82230 Overseas $3,900,000 $2,131 $4,100,000 1,830 Single Family 6/4 148
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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 07-03-2020.

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Key Largo, Florida 33070

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