Having lived in Marion county and worked in Portland for years, I have had the opportunity to help several clients do just what you are proposing. There are many great 55+ places in the Portland Area. Call me with any specific questions.
Any move needs to be planned out. From your comment your haven't listed your property for sale yet. Plus, you haven't indicated (and you probably should NOT on an open forum message board such as Trulia) how much your buying price range will be. With all things "purchase" the bottom line is . . . well . . . the bottom line. How much is in your purchase budget? (Again, this type of information should not be posted on a message board).
Finding a home to purchase is all about the buyers bottom line, the avialability of inventory in that price range and area.
Your comments don't address or answer the many questions I would have of a buyer who is contemplating a move. Do you need to sell in order to buy? What's your time frame? What's your budget? etc.
I do not work in Salem (but know a very good agent in the area). It would seem to me that you need to find two agents, one in Salem that will market your property for sale and another in the Metro Portland area that will assist you in indentifying properties that may work for you that are within your budget and price range.
Carla Muss-Jacobs, Principal Broker/Owner
EBA Portland, LLC
Exclusive Buyers Agent
Assisting Buyers in Metro Portland since 1999
Your property in SE Salem appears to have a variety of possible uses to potential buyers. For this reason, I would highly recommend you obtain the services of a Real Estate Broker who knows your area and can help determine what we call the highest and best use of your property. This is what will bring the highest value to your property and bring the most money out of a sale. With all of the zoning regulations, etc. I would not recommend you take this on yourself. I would be happy to refer you to a great agent in your area.
As for your search in Portland, I would love the opportunity to work with you. I am knowledgeable about the 55+ communities and I can help you figure out the areas of Portland that might best fit your lifestyle. Please do not hesitate to contact me with any questions you may have.
Real Estate Broker, Windermere
(503) 522-5803 direct
If you like, I can refer you to a good Broker who handles the Salem area. I would be happy to help you with your search in the Portland metro area as well. Let me know if I can be of service to you.
RE/MAX equity group
9200 SE Sunnybrook Blvd., Ste 100
Clackamas, OR 97015
Also, see this older Trulia thread for some ideas on area for 55 plus... click below: