Not to be redundant, but among these towns, more depends on lifestyle. Lexington, for example, provides a Rt 2, Rt 3, Rt 128/I95 easy access while Winchester is I93, and Weston/Wellesley ate I90.
This link is to Boston Magazines "Best Places to Live" article. All 4 are called 'Recession Proof".
I live in Lexington & I am doing business in all 4 of those towns. When working with a Buyer, I have a Buyer Wish List that identifies the "lifestyle needs" to will help choose the town(s) to concentrate on.
They are all fantastic communities but I my bias to Lexington can't be hidden. To your question about investement worth - Weston, Wellesley and Winchester are comparable to Lexington in pricing. While Wayland is a great community, I wouldn't compare to the other four towns. Weston and Wellesely have much higher median home prices to Lexington's (by almost double). There's some crazy statistic out there about the percentage of Lexington HS students application/acceptance to Harvard - it's very high. Hope this is helpful...
I work in Lexington and my brother lives in Winchester. I've financed homes in all of the communities you've mentioned and each time my borrowers have found the "ideal" home- the one best suited for their specific preferences and finances. That's where chatting with a local real estate professional comes in handy.
Anyhow, as everyone has said- these are all very good towns to live in that will be able to bounce back pretty good as far as house values.
I would deem Wayland on the "lower" scale of a group of excellent choices. Lower in home prices as well, but still a good town.
Much depends on where you and/or your wife will be working. Winchester is going to be the closest to downtown Boston. You should also check out the tax rates in these towns. I'm not sure how they measure.
If you need any financing help or have any related questions, feel free to contact me anytime. Thanks, and good luck,
I agree with the previous agents, great towns, different but all of them great. If I may suggest, Ask your buyer's agent for a 10 year report on those towns. If you do not have a buyer's agent you should hire one. Then each house is very individual and unique. List all the pro and cons, for all the houses that you will visit and based on your budget and your lifestyle, wants, needs etc for you and your family you should be able to make the best decision. Yanni