Hi Ann - Woodbridge and Orange is located just outside of New Haven, in New Haven County. They share the same school district, each having their own elementary and jr high, but one high school which serves Orange, Woodbridge and Bethany; Amity Regional High School. They're know for their above-average school system. I would advise you to visit the below link to view all high school's in CT & their 2010 SAT scores. You will find these towns under Amity Regional High School.
Woodbridge is a suburban community with approx 10K residents. Taxes may seem higher as Woodbridge has more property (most on 1.5+acres), homes tend to be a little larger than you will find in Orange, and you will find an array style of homes. Woodbridge homes are tucked away so if you do not mind traveling 10-15 minutes to get to different places (shopping, movies, gas stations, bank, friends, etc) then it may be for you. Orange has approx 14K residents and borders urban areas. Homes in Orange tend to be on acre lots and consist mainly of ranches and capes. If you're also looking in this direct area you should not leave out Milford. Milford runs directly along the shoreline and has approx 50K residents, however, if you're looking for a home and have younger children then Milford should not be overlooked. There are many sought after areas in Milford. Milford is known to have Fairfield ammenties but at a less expensive price. Taxes in Milford are a little high compared to Orange, but the homes also tend to be larger. Milford also offers trash and bulk-trash pick-up where Orange and Woodbridge do not.
You will find all the shopping you need on RT1 in Milford and Orange. Milford is known as "furniture row" and has every car dealership known. You will be minutes to every store including outlets!
Growing up in these areas I do know them quite well. If you are not working with a Realtor, which I assume you're not, I would love to spend the time with you and show you all around and help you find the right home for your family. You can email me at RltrKar@aol.com, call me at 203-535-5706 or visit my website at www.RealEstateGalleryCT.com. Good luck with your search.