Affordable Neighborhoods in Cookeville: Winsor Hill Winsor Hill is a small subdivision located within Cookeville city limits. The number one selling point for this neighborhood is it's location in town, and proximity to the Hwy 111 on/off ramp. The Winsor Hill neighborhood is a dream come true for someone who has a daily commute.  In less than 2 minutes, you can be on Hwy 111 or I-40.  Of course, it's also one of the more affordable neighborhoods in Cookeville. Based on the past two years of sales, prices in the Winsor Hill subdivision range from $100k - $140k.  Despite the modest price point, this is a tidy little neighborhood of cute homes. Winsor Hill tends to be especially popular with young couples, college students, and retirees because of the small, low maintenance yards. Of cour... 05/19/2011