Is it an option to refinish what you have with a new stain and then stain the whole floor together?

I had been advised that it wouldn't be possible to get them to match even doing this

^ agree, i’d wait until i had the budget to make it all one continuous flooring

i will say it will make the room seem so much bigger

I'd select a new paint for all the walls and replace the carpet and not install the wood.

Sand down the old flooring, install new unfinished flooring in the new area then finish all the same to get an even look. If someone says they can not do that then look for another company as they do this all the time weaving in new flooring so it can look seamless. BUT also compare that cost to putting in all new flooring. Also have you looked under the carpet? Is there wood flooring under it? You never know.

Sand the old get unfinished new and stain all to match. BTW I would choose maple over oak every time . That carpet looks like you ran out of money and went cheap for the LR.

Just deleted my suggestions since the other two--Patricia and Lorraine--are what you should do.

A good flooring professional will know how to expertly weave new into old and sand and refinish both so they look the same. I've seen it done dozens of times with floors that are 100 years old.

Thank you to all who responded it helped to solidify a plan. I will be pursuing what it takes to get hardwood weaved in. Actually I just read an old real estate listing that described the wood as 'custom cherry flooring with walnut accents ', so although the new realtor said this was maple, it is apparently cherry.

It is near impossible to get new flooring to match existing. Sometimes even refinishing existing and new flooring won't give you the result you want. IMO it is usually best to replace all flooring at one time. In lieu of that will advise that you differentiate between the flooring as you have now. In our projects, if we have carpeting, it's usually done in upstairs bedrooms. You could choose another flooring to replace your present carpeting.

Just for the heck of it, here's an alternative to matching:

https://www.houzz.com/discussions/6541912/step-down-living-room#n=36