If you were going to vacation with an eye to maybe buying a second home .. would you prefer Chatham or Orleans .. with an eye on best beaches .. programs for children .. long term appreciation .. Suggestions as to what areas within the town would be great as well ..

Either town will hold its value because both are essentially built-out...there is very little available undeveloped land to be purchased. I prefer Orleans because it has more accessible shoreline, is more of a year-round town, and is not as congested in the summer. 60% of the tax-payers in Chatham are non-residents so the town is very busy in the summer with tourists and second-homeowners yet rather empty in the winter. People in Chatham tend to go to Orleans to shop in the winter. Chatham has beaches on Nantucket Sound and Pleasant Bay that are nice for kids because the water is warmer and calmer. It also has some access by boat to the outer beaches on the Atlantic which are owned by the National Seashore. Parking in Chatham, during the summer, can be a problem. Orleans has a more constant, yet aging, year-round population and serves as the commercial center for the outer cape but has many areas that are quiet and residential. The beaches in Orleans are popular with the "younger set", Nauset Beach is a popular teen-late 20's scene and Skaket Beach on the bay-side is nice for younger kids. East Orleans and South Orleans are the priciest areas in that town but anything near the water anywhere on the outer cape will still cost you dearly. For a better value, you might consider Brewster and Eastham, both smaller towns with fewer services but lovely beaches and close enough to Orleans and Chatham to shop etc. Brewster has Rt. 6A, a scenic, historic road along the Bay side of the cape, while Eastham is known for its fabulous National Seashore Ocean Beaches as well as for its lovely bay beaches.
I hope this helps. You might want to check out the individual town's Chamber of Commerce site for each town to get more specific information about tax rates, population etc

This is absolutely wonderful information .. I appreciate all your time and effort ... We are heading down for a few days in February to looking around .. and will let you know our thoughts .. Again ... much appreciation to you ..