All Forum Posts by: Jen Whitehead

Hi Laura, I own two short term rentals on Little Sebago and one in Old Orchard Beach. I do short term rentals during the summer but then rent mid-term from September/October through May. Let me know if you'd like to chat sometime!

Quote from @Dee Shiozaki:

Quote from @Jen Whitehead:

 My husband and I have two properties that we used second home loans and in both cases my lender knows that we also rent out to help cover the costs. You just have to spend so many weeks there to be considered second home. In both cases, we only put 10 percent down. I'd be happy to share my lenders contact info with you. She works for Annie Mac and they're a national lender. Good luck!

what lender ?  I talked to rocket they said though it is 10% down min they usually end up being 25% down.  

Both of them are with Harbor One Mortgage. 

Everyone had great points above but something that stood out to me is that you said option 2 is in a good location. If you have good, established relationships with contractors then I would take option 2 any day! This is where you can really gain some sweat equity and potentially have better tenants over time.

Hi Melanie, That's so exciting!!! I have a duplex in Westbrook and Buxton coming on the market this spring.

We have had long term rentals in Westbrook and Washington DC but I have a lot of fun with our STR rentals in OOB and Little Sebago Lake. During the winter, I'm able to rent them out mid term. They've given me the best return, especially the OOB property.

What type of investment properties will you start with?

You've had some great suggestions already but I just wanted to add that in our STR in Old Orchard Beach, Maine we had a finished garage space that we turned into an arcade. Everyone who has stayed has commented on that room and how both kids and adults LOVE it so much. I haven't seen anyone else in my market with a game room like this so I feel like it's helps me stand out. I can charge the same as the rentals right on the beach and we're a few blocks away.

We have a skee ball game, an old school cocktail table style arcade machine for two people, a newer NBA jam for four people, foosball table, mural wall with neon sign for instagram photos and a closet with beach supplies. 

Our rentals are in beach and lake areas of Maine so we do STR's during the summer months and switch to mid term from Sept/Oct to May. So we offer furnished but we do not provide the towels and linens during the mid-term rental. The monthly rentals are discounted but slightly greater than what local long term rentals charge in the same areas. For example, 2 bedroom apartments in Old Orchard Beach year round are about 1600-1800 month. Our mid term rentals we get $2000-2400 monthly during what is considered "off season" in Old Orchard Beach.

There are lenders that are knowledgeable about short term rentals and their bread and butter are DSCR loans that will take into account projected income. I think it may be against the rules to post specific companies here.

I have a friend/client that owns a multi-unit, (3 units) in Portland, Maine and does VERY well with short term rentals. It's a three story building with one unit on each floor. This building is from the early 1900's and has no soundproofing. Like others have mentioned, make sure that you make it clear in your advertising that it is an apartment building and you should be fine. 

The best way is to call the code enforcement office for the town/city that you're looking to have a STR.

@Ahmad Mian, The three areas that you mentioned have similar histories. They're all cities on a river, which made them great for trade. They all had very successful mills, that began to shut down in the 80's and 90's. This caused the area's economies to become depressed. But the past couple of decades have shown how Mainers are resilient and will always come back stronger. The mills have been restored and used for local businesses, artists and amazing restaurants. I have lived and have family in the Westbrook and Lewiston areas and my office is in Saco, next door to Biddeford.

All three of these areas, but especially Lewiston, all have room to continue their growth. Lewiston recently won a major $30 million grant, called the Choice Neighborhood Grant. This area also has some of the best cash flow in the state. It hasn't always had great appreciation and there is still some stigma around the "tree streets" neighborhood but it also has a lot going for it, being only 45 minutes from Portland, Bates College, more diversity than most of the state and excellent hospitals. 

Please let me know if you have any other specific questions, I'd be happy to help!