If you’ve driven past the Bobby Drive entrance lately, you’ve probably noticed what we have. Both stone monuments at the entrance are in rough shape.

The right side took a hit from a car several years ago and has been visibly damaged since. The left side is a slower story… the foundation underneath it is failing, and the structure has started to separate. What started as cosmetic wear is now structural. They are past the point of patching.

So we got a quote.

The Quote

A local mason walked the site and put together a full scope for rebuilding the Bobby Drive entrance from the ground up. Here is what the work would involve:

  • Demolition and prep: Remove all stones from the pillars. Remove all broken stones from the walls. Dig 12 inches of dirt out to create a trench.
  • New foundations: Lay rebar, then pour concrete into the trench to create new concrete foundations for both pillars and both wall sections.
  • Rebuild from the ground up: Once the foundations cure, lay blocks on top, fill them with rebar and concrete. Then lay stone on all four sides of each pillar. Rebuild the two 5-foot wall sections, one on each side of the entrance.
  • Finish work: Pour new concrete caps on both walls and both pillar tops. Joint all the stone heads with a proper jointer. Sweep and clean the site.
  • Materials included: stone, brown sand, concrete bags, type S cement, rebar, blocks.

Total cost: $11,000

This is a complete rebuild using the existing design. Same look, but on a new foundation that will last.

The Bigger Question

Here is where it gets interesting.

If we are rebuilding Bobby Drive from scratch, the natural question becomes: what about Harpeth Hills? Do the two entrances need to match?

Right now they do not. They were built at different times with different designs. If we rebuild Bobby Drive and leave Harpeth Hills as-is, we are committing to two different looks at the two entrances to our neighborhood, possibly for the next 30 years.

There is a real argument for matching them. Two entrances. One neighborhood. Cohesive identity. A clear sense of arrival no matter which way you come in.

There is also a real argument against. Harpeth Hills isn’t failing the way Bobby Drive is. Rebuilding something that doesn’t need rebuilding is expensive. And matching to Bobby’s existing design might not be what the neighborhood would choose if we were starting fresh.

We don’t know the answer yet. And honestly, we don’t think the board should answer it on its own.

What Happens Next

This is a neighborhood decision. Not a board decision.

A few things to know:

1. This is a separate fundraiser, not part of the annual budget.

The $11,000 for Bobby Drive (or whatever the final amount is if we decide to match Harpeth Hills) is well beyond what our annual giving covers. Our regular contributions go toward lawn care, lighting, mulch, and basic operating expenses. A monument rebuild is a capital project that requires its own dedicated fundraiser, in addition to what neighbors already give.

2. We need to decide together.

Before we launch a capital campaign, we want input from the community on three questions:

  • Do we rebuild Bobby Drive as-is, using the existing design?
  • Do we expand the project to match Harpeth Hills, creating a unified look at both entrances?
  • Or do we choose a new design for both, taking this as an opportunity to rethink what the entrances should look like?

Each path has a different price tag and a different impact on the neighborhood. We want to hear from you before we commit.

3. We are getting additional bids.

The $11,000 quote is our first one. We are working on getting two or three more so we have a real range, not a single data point. We will share those numbers with the community as they come in.

How to Weigh In

If you have thoughts on any of this, we want to hear them. A few ways to engage:

We will be putting together a more formal survey in the coming weeks so every household has a chance to weigh in. If you want to make sure you are on the email list to receive that survey, add your name and address at the top of grasslandestatestn.com.

Why This Matters

The entrances are the first thing visitors see when they come into our neighborhood. They are the last thing we see when we drive away. They are small things and big things at the same time.

For years, the monuments have been there, quietly doing their job. Now they need our attention, and what we do next will shape the look of this neighborhood for a long time.

We are glad to be making this decision with you.

More soon.

Kyle Chowning, President
Denise Gross, Secretary
Grassland Estates Community Organization, Inc.