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Is Pittsboro the next Cary? Growth, zoning fights, and a market at a crossroads

Chatham Journal

By Gene Galin

Pittsboro, NC – The question hovering over Chatham County’s courthouse square and new subdivisions alike sounds half like a boast and half like a warning: Is Pittsboro becoming the next Cary? A year of market data suggests the town and its surrounding communities are no longer a “hidden” alternative to Wake County prices, even as higher mortgage rates and a slower national housing cycle have cooled the most frantic bidding wars. At the same time, the forces reshaping the area—mega-development at Chatham Park, the planned Storyliving by Disney community called Asteria, and renewed attention to infrastructure and zoning—are colliding with local concerns about pace, parking, and who benefits. The result is a market that remains attractive, but more complicated: sellers still see eye-popping appreciation compared with the last decade, buyers have more leverage than they did in 2021–2022, and landowners face increasingly high-stakes decisions where the fine print can matter as much as the price.

The Market Snapshot: Cooling Isn’t the Same as Collapsing

If the past few years were defined by speed—list today, show tomorrow, multiple offers by Sunday—recent numbers tell a slower, more selective story.

In Pittsboro, Redfin reports a January 2026 median sale price of about $515,000, roughly down 1.9% year over year, with homes taking about 73 days to sell on average. At the county level, Redfin reports Chatham County’s median sale price in January 2026 at about $629,000, down 12.6% year over year, with the market still moving—just not sprinting.

That apparent contradiction—Pittsboro steadier while the county shows a sharper year-over-year dip—highlights one of the key challenges in interpreting “market update” headlines in fast-changing places: Chatham County isn’t one market. It’s a patchwork of price bands and product types, from established neighborhoods near downtown Pittsboro to newer homes in master-planned communities, rural tracts with development potential, and higher-end custom builds on larger parcels.

National conditions matter, too. Mortgage rates remain elevated compared with the post-pandemic lows, shaping what buyers can afford and how quickly deals close. A 30-year fixed-rate mortgage hovering near 6%, can mean hundreds of dollars a month in added payments versus the 3% era—enough to turn “maybe” buyers into “not yet,” and to encourage sellers to hold onto homes financed at lower rates.

Yet “higher rates” doesn’t automatically translate into “no demand.” It often translates into a more normal housing market: more time on market, more inspection negotiations, and more attention to value rather than momentum.

Why People Keep Asking “Next Cary”

The “next Cary” framing is really shorthand for two questions: Will Pittsboro and Chatham County keep absorbing Triangle growth—and will they change in the process?

In my conversation with real estate broker Eric Andrews, he answers my lightning-round question about whether Chatham County real estate is overrated or underrated: “Probably underrated,” he says, arguing that people are underestimating “the impact of Disney and what’s coming to this area.” (While our conversation itself is informal and local in tone, it captures a widely shared sentiment: growth is no longer hypothetical.)

That “Disney” reference isn’t just a metaphor. Storyliving by Disney—the company’s residential-community brand—has announced Asteria, planned within the broader Chatham Park development. Disney’s Asteria page describes the community as located outside Raleigh and positioned as the brand’s second such community. (Storyliving by Disney) Regional reporting has described Asteria as a Disney-branded residential community planned within Chatham Park, with the Chatham Park/Asteria storyline now a recurring feature in how outsiders talk about Pittsboro’s future.

The other driver is the gravitational pull of Wake County prices. Andrews discusses a proposed cricket facility in Moncure and frames it bluntly: the project is intended to serve Wake County users because “the land is too darn expensive in Wake County,” making Chatham a place where recreation, housing, and even commercial projects can still find room—at least for now.

This is the fundamental “next Cary” dynamic: the Triangle’s jobs and amenities push demand outward, and the next ring of communities responds with housing supply, development proposals, and the political fights that come with them.

Chatham Park and Asteria: The Development Engine (and the Debate)

Chatham Park isn’t new, but its scale—and the pace at which decisions around it are now shaping the town’s identity—continues to put Pittsboro in a category few small towns ever enter.

The Town of Pittsboro describes Chatham Park as a major planned development with multiple “Small Area Plans,” including the South Village Small Area Plan approved on Nov. 10, 2025. That kind of planning framework matters because it influences where roads go, where retail concentrates, how housing types mix, and how quickly future phases can move.

For residents, the debate is often less about whether growth will happen than about how—and for whom. Public radio reporting from WUNC has emphasized both the sheer scale of Chatham Park and the public unease that can come with it, noting plans that include thousands of residential units and massive non-residential buildout, while framing Asteria as a flashpoint in the broader conversation about change.

In practical market terms, Chatham Park and Asteria shape expectations. They can raise the perceived “story” of the region—more attention, more interest, more speculative thinking—and they can also increase real demand if development attracts new residents, new retail, and new jobs. But large projects can also concentrate benefits, strain infrastructure, and generate distrust when residents feel decisions are moving faster than community input.

That tension shows up repeatedly in local conversations: planning board debates, rezoning hearings, and the smaller controversies that hint at larger fears—like a church project being “shot down,” or neighbors fighting for parking protections near a proposed sports facility.

Planning and Zoning: Where the Big Picture Becomes Personal

We talked about the fact that planning decisions aren’t abstract; they determine whether projects live or die.

Early in our conversation, Eric references a “big community church” that “got shot down,” with uncertainty about whether it went to court and how it ultimately turned out. Even without the specifics, the subtext is familiar in fast-growing communities: zoning, traffic, and neighborhood compatibility can turn what one group sees as a community asset into what another group sees as a disruption.

Later, the cricket-field discussion becomes a case study in how these conflicts play out. I recall earlier efforts to establish cricket fields that foundered not because the concept lacked supporters but because the proposal didn’t resolve core neighbor concerns—especially parking and overflow impacts. He summarizes the concern as: residents nearby didn’t want visitors “parking in our driveways and in our yards,” and a proposal can fail if it doesn’t produce a workable solution.

This aligns with what planning departments often see in public hearings: many residents can tolerate change in theory, but not chaos in practice. Parking, traffic, stormwater, noise, and lighting are the issues that turn growth into a doorstep problem.

And in Chatham County, cricket fields are not merely hypothetical. The county’s official rezoning page for “The Pavilion at New Hill Rezoning” describes a request involving approximately 66 acres at 3378 Christian Chapel Church Rd. for a recreation facility, including attached application and site-plan materials. An earlier county page also documents a “Triangle Cricket League” rezoning request for cricket fields and facilities.

To residents skimming headlines, one sports facility might not seem like a market mover. But it can be—because it illustrates the broader transformation underway: Chatham County is increasingly a place where regional demand (sports leagues, jobs, housing) seeks space, and local systems must decide how to accommodate it.

The Cricket Field Question: Public Cost, Private Benefit, and Regional Demand

The cricket-field issue triggers a familiar local reaction: skepticism about who is paying and why.

We talked about community questions along these lines: Why would the county or town pay for a cricket field when they aren’t funding baseball fields in the same way? The conversation then pivots to the developer’s role—framing the facility as a private investment responding to perceived demand, and noting that the facility would charge users rather than charging spectators.

What’s notable here isn’t the sport; it’s the argument. In growth regions, local governments constantly balance public investment with private development, often using incentives, infrastructure support, or zoning flexibility to shape outcomes. Residents, in turn, watch for mismatches—projects that feel like subsidies for newcomers, or amenities that don’t serve existing communities.

There’s also a regional logic at work. Andrews says bluntly that there aren’t “a tremendous amount of cricket players in Chatham County,” implying the facility is aimed at Wake County demand—people willing to drive 30–45 minutes because land and facilities are harder to secure in Wake. Whether one views that as smart regionalism or as catering to outsiders often depends on where one sits.

From a market perspective, these projects can add to an area’s attractiveness—more amenities, more recreation, more reasons to move nearby. But they can also inflame political opposition, slowing approvals and creating uncertainty that affects both developers and homeowners.

Downtown Pittsboro vs. Master-Planned Retail: Two Models, One Future

One of the most revealing moments in the transcript comes when Andrews is asked what property type he would buy and hold for 20 years. His answer: commercial property downtown, if he could find it.

His reasoning is essentially a “two engines” theory:

In his view, the two are not purely competitors; they are “riding coattails of one another.” Downtown’s appeal helps sell Chatham Park’s residential growth, while new residents and new retail can create more customers and attention for downtown.

This interplay matters because it shapes where investment goes. If downtown commercial becomes scarce, pricing can rise and lease negotiations can tighten. If national retail expands too quickly, it can pull activity away from local businesses. The market outcome depends not just on demand, but on execution: connectivity, parking, walkability, and whether downtown remains an experience rather than merely a place on the way to somewhere else.

Sellers in 2026: The “Where Are You Going?” Reality Check

Andrews offers a piece of advice that real estate agents across the country have been repeating as the market normalizes: if you’re excited about what your home is worth, you still have to answer the next question—“Where you gonna go?”

That’s the lock-in problem of the current era. Many homeowners bought or refinanced when rates were far lower than today’s. Selling a home with a low-rate mortgage can mean buying the next home at a much higher borrowing cost, even if the price is similar. Even small rate differences can reshape affordability, particularly for move-up buyers.

For sellers, this reality can produce three outcomes:

  1. They still sell—but only if the move is essential (job change, family needs, downsizing).
  2. They keep the home and renovate, accepting construction timelines and supply delays.
  3. They list higher and wait, hoping the market meets them—sometimes successfully, sometimes not.

Landowners: Where the Stakes—and the Timeframes—Get Bigger

If the residential market has shifted from sprint to jog, land sales operate in a different time zone altogether.

Andrews stresses a point that many landowners learn too late: selling land requires specialized experience, and the agent who is excellent at neighborhood home sales may not be equipped for land deals involving entitlements, zoning contingencies, and multi-year timelines.

He describes a key split:

That two-year window can be profitable or punishing depending on contract structure. Andrews claims he has “made a decent living” from landowners who had property tied up for years and “got nothing” at the end—an anecdotal warning, but a common one in development markets: inexperienced sellers can sign contracts that give buyers control without adequate compensation if approvals fail.

The lesson for Chatham County landowners, especially as development pressure increases, is not simply “sell” or “don’t sell.” It’s “treat it like a sophisticated transaction.” That means understanding:

In a region where projects can hinge on planning-board decisions and neighborhood opposition, these details are not “lawyer stuff.” They are the difference between a life-changing sale and years of limbo.

Affordability, Incentives, and the New Negotiation Era

Even in high-demand regions, affordability is now the organizing principle of the housing story.

Affordability pressures have pushed some builders to offer incentives—rate buy-downs, price cuts, and closing-cost assistance—while warning that incentives may lose effectiveness if broader economic uncertainty persists. Housing affordability highlights a different—but related—pressure point: when home values rise quickly, property-tax burdens can feel increasingly heavy for homeowners, creating a dilemma where selling is profitable but replacement housing is hard to afford.

For Pittsboro and Chatham County, these dynamics show up in practical ways:

The market is still active, but it’s less forgiving—and that can be healthier for buyers, even if it frustrates sellers who anchored expectations to peak-era pricing.

The Civic Side of a Housing Story: Trust, Process, and Identity

A housing market is never just numbers. It’s also belief: belief that growth will be handled fairly, belief that infrastructure will keep up, belief that a place will remain itself even as it changes.

We touch on the fact that civic undercurrent comes through in small remarks: uncertainty about lawsuits, questions about why certain amenities get support, and jokes about stereotypes that outsiders hold about Chatham County. Those moments matter because they reveal something deeper—an ongoing negotiation about identity.

Pittsboro’s growth story sits at an intersection:

The “next Cary” question, in that sense, may be less about whether Pittsboro becomes a larger city and more about whether it can grow without losing the qualities that made people want to live there in the first place.

Pittsboro Isn’t Becoming Cary—But It’s Entering the Same Conversation

Pittsboro is not Cary. But the town is now grappling with the same set of pressures that define high-growth metros: affordability constraints, contested zoning decisions, regional demand spilling across borders, and development that brings both opportunity and conflict.

For readers wondering what to do next, the guidance is straightforward:

Pittsboro’s future is being written in real time—one subdivision approval, one downtown lease, one contentious parking plan at a time. Whether it becomes “the next Cary” may be the wrong measure. The better question is whether Pittsboro can become the next Pittsboro—bigger, yes, but still recognizable to the people who call it home.

Watch on YouTube – Is Pittsboro the next Raleigh? (2025 Market Update)

“Pittsboro’s Growth: Community Planning Challenges and Market Changes”

00:17 Community planning decisions impact project outcomes in Pittsboro.

02:23 Cricket facility in Chatham County aims to serve Wake County players.

04:15 Understanding land value and the importance of experienced agents.

06:16 Building a house in Pittsboro takes about a year due to various delays.

08:29 A TikTok broadcaster brings success and family connections to the real estate team.

10:31 Celebrating a large family Christmas in a spacious home.

12:30 Pittsboro offers a friendly community with business opportunities.

14:44 Pittsboro is evolving with new local businesses and community focus.

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