"Beautiful and Convenient, if you can afford it"
Woodmont Blvd between Estes and Hillsboro is another frequently traveled road that must simply wish it could be left alone. With the cheapest house listed there now at $1.1M, there are likely better places to spend your cash. However, the road itself is picture perfect, with large mature lawns and huge, old trees. Likewise the draw of having the conveniences of Green Hills right on your doorstep must be almost too much to bear. The schools nearby are good, with Hillsboro High being less than a mile, and MBA, Harpeth Hall and Ensworth all within two in either direction. Homes here range from old and traditional to new builds on sites of tear-downs. The traffic can be heavy, though, with people using the street as a shortcut between Green Hills and Belle Meade/West End, and thus I would still - no matter how tempted, give pause before buying right on the streetfront itself. Behind Woodmont you have quieter areas with still large and prestigious homes, and it may be worth exploring those as an alternative to moving out of town or giving up the conveniences that living in this locale would provide.