$3,200,000
Active
1d
$3,200,000
131 Ojibway
Islamorada, FL 33070
4 bd4 ba3,715 sqft
Indian Waterways
Islamorada, FL
Investment Properties in Islamorada
Income-producing properties and rental investments in Islamorada, Florida. Browse active MLS listings and communities with List & Sell FL.
0
Communities
Islamorada
City
1%
Listing Fee
Active Listings
32 active listings
$2,450,000
Active
$2,450,000
179 Azalea
Islamorada, FL 33070
4 bd4 ba1,800 sqft
Plantation Key Colony 1st
$3,275,000
Active
1d
$3,275,000
59 Plaza Del Sol
Islamorada, FL 33036
5 bd3 ba2,922 sqft
Port Antigua Plat No 3 &
$1,700,000
Active
21d
$1,700,000
133 Anglers
Islamorada, FL 33036
2 bd2.5 ba1,170 sqft
Anglers Reef
$2,950,000
Active
34d
$2,950,000
80902 OLD
Islamorada, FL 33036
4 bd3 ba3,550 sqft
Coral Cove
$1,199,999
Active
1d
$1,199,999
111 ANGLERS
Islamorada, FL 33036
2 bd2.5 ba1,376 sqft
Anglers Reef
$4,899,000
Active
14d
$4,899,000
115 Villa Bella
Islamorada, FL 33036
4 bd4 ba2,476 sqft
Venetian Shores
$18,499,000
Active
31d
$18,499,000
87429 Old
Islamorada, FL 33036
6 bd8 ba6,692 sqft
Plantation Beach
$24,995,000
Active
22d
$24,995,000
82719 Old
Islamorada, FL 33036
7 bd10.5 ba10,182 sqft
Strattons Subd
$1,950,000
Active
42d
$1,950,000
161 Palermo
Islamorada, FL 33036
3 bd2 ba1,190 sqft
Venetian Shores No 1
$999,999
Active
49d
$999,999
100 IROQUOIS #5
Islamorada, FL 33036
3 bd3 ba1,710 sqft
Lower Matecumbe Beach
$2,350,000
Active
67d
$2,350,000
316 Dr
Islamorada, FL 33036
3 bd3.5 ba0 sqft
Plantation Lake Estates
$2,740,000
Active
62d
$2,740,000
122 Court Contessa
Islamorada, FL 33036
3 bd3.5 ba2,374 sqft
Port Antigua Plat No 5 &
$3,750,000
Active
85d
$3,750,000
74049 Overseas
Islamorada, FL 33036
4 bd4 ba2,596 sqft
Lower Matecumbe Beach
$2,100,000
Active
51d
$2,100,000
82891 Overseas
Islamorada, FL 33036
3 bd3.5 ba2,036 sqft
Ocean View
$649,000
Active
67d
$649,000
81801 Old #754
Islamorada, FL 33036
1 bd1 ba550 sqft
Strattons
$10,950,000
Active
67d
$10,950,000
77350 Overseas
Islamorada, FL 33036
6 bd6.5 ba6,577 sqft
Matecumbe Ocean Bay Sec 2
$2,500,000
Active
113d
$2,500,000
107 Valencia
Islamorada, FL 33036
3 bd2.5 ba1,632 sqft
Venetian Shores No 2
$29,000,000
Active
128d
$29,000,000
75090 Overseas
Islamorada, FL 33036
4 bd5.5 ba8,194 sqft
Matecumbe Ocean Bay (75.0)
$699,000
Active
139d
$699,000
81801 Overseas Highway #714
Islamorada, FL 33036
1 bd1 ba550 sqft
Hotel Condominium At Cheeca Lodge, Bldgs 1 8 (6
$649,000
Active
150d
$649,000
118 Cortez #B
Islamorada, FL 33036
2 bd2 ba1,079 sqft
Islamorada South
$25,000,000
Active
126d
$25,000,000
82768 Overseas
Islamorada, FL 33036
7 bd10 ba8,288 sqft
Islamorada
$298,000
Active
168d
$298,000
84961 Old Hwy 17
Islamorada, FL 33036
1 bd1 ba0 sqft
Windley Key Mobile Home P
$5,999,000
Active
185d
$5,999,000
1101 Mastic
Islamorada, FL 33036
8 bd6 ba3,649 sqft
Strattons Subdivision Pb2-
Information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data deemed reliable but not guaranteed. © 2026 Beaches MLS, Inc.
About Investment Properties in Islamorada
Investment Properties in Islamorada, FL
Looking for investment properties in Islamorada? Here is what to know about this part of the County market. Investment and multi-family properties in Islamorada range from single-family rentals to two-, three-, and four-unit buildings across County. A two-to-four-unit property can be owner-occupied with one unit while the others help cover the payment, a strategy often called house-hacking.
Financing options go beyond a standard mortgage: FHA covers owner-occupied 2-to-4-unit buildings with a low down payment, and DSCR loans qualify on the property's rental income rather than your tax returns. Run the numbers on rent versus price, budget for insurance and maintenance, and understand Florida landlord basics before you buy.
Frequently Asked Questions
Investment Properties in Islamorada FAQ
How do I finance an investment property in Islamorada?+
Options include conventional investor loans, FHA for owner-occupied 2-to-4-unit buildings at a low down payment, and DSCR loans that qualify on rental income with no tax returns. The right one depends on whether you will live in a unit.
What is house-hacking a duplex or triplex in Islamorada?+
You live in one unit and rent the others, using the rental income to offset your mortgage. FHA financing at a low down payment makes owner-occupied 2-to-4-unit buildings a common path.
How do I evaluate a Islamorada rental's return?+
Compare the expected rent to the purchase price and operating costs to estimate the cap rate and cash flow. We can share rent comparables and recent sales for the specific building type.
Do I need a property manager for a County rental?+
Not necessarily, but many out-of-area owners use one. Factor management cost into your return if you will not self-manage.