Brookline is a fantastic city, with great public schools, but you will have a hard time finding what you are looking for, especially with parking (no street parking permitted), for $400k. Same thing with Newton, Wellesley. I would recommend that you look at Watertown. The schools are good, but do not compare to the towns mentioned above. But, Watertown is on a bus line, not the subway.
Veronique mentioned West Roxbury and Dedham, those towns are very close to Brookline, but again the schools fall short. West Roxbury is part of the Boston school system. West Roxbury is on the Orange Line, which connects to the Green (Brookline).
So, to get the good fixer-upper and be on the T, you will have to decide how far from Brookline you are willing to live, and accept that you will have to take the train into Boston, and then the subway back out.
Try Needham - good schools and on the T (train, not subway). Realtor.com shows two houses between $300k and $400k, but they only have 1 bath, not 1.5.
Good luck.
Wellesley: Fabulous area to live and great school system
2 bedroom that needs some updating on the interiors
http://www.territoryre.com/SF_Property.php?LIST_NO=70672586
Newton: Nice proximity to Boston and great school system:
Here is a place that needs fixing up but is in a good commuter location:
http://www.territoryre.com/SF_Property.php?LIST_NO=70659067
Here is one near the D line and major commuting routes:
http://www.territoryre.com/SF_Property.php?LIST_NO=70711369
Brookline:Great commute for you and fabulous schools
Quaint updated SF:
http://www.territoryre.com/SF_Property.php?LIST_NO=70657179
This place needs a little love but has had some updating, is in a great spot and look at the amazing beamed ceilings, awesome:
http://www.territoryre.com/SF_Property.php?LIST_NO=70709914
Hope this helps :)
I live and work in the Merrimack Valley and North Shore area, and I think you would find it perfect. The area offers an easy commute, as it is surrounded by 3 major Boston commuter routes, and just about every town has a commuter rail station. It's a lovely area with quintessential and SAFE New England neighborhoods. It's a quick drive to the beaches, to Boston, and to skiing, and best of all it's AFFORDABLE!
I publish a Homes & Land Magazine for that area, we have a few thousand listings on our web site that you may want to check out. http://www.HomesAndLandMA.com. Or I would be happy to mail you a copy of the next issue, just let me know! Best of luck with your search.
Cary Bowman
Publisher
Homes & Land Magazine
I would be happy to help you if you need to.
Veronique
617-477-5079
