Use the live search below to see every house for sale in Chestnut Hill, Philadelphia:

• Stone single-family homes

• Twins & row homes

• Historic properties

• Luxury and estate homes near the Wissahickon

Save searches, mark favorites, and ask questions about any property right from this page.

Why Buyers Love Chestnut Hill

Walkable Main Street Vibes

Chestnut Hill’s main drag, Germantown Avenue, is lined with:

• Cafés, bakeries, and restaurants

• Boutiques and galleries

• A neighborhood market and local businesses

Forbes once named Chestnut Hill one of the “top seven urban enclaves” in the country for its mix of shops, architecture, and tree-lined streets.

Historic, Stately Homes

Many streets are lined with:

• Classic ** Wissahickon schist stone homes**

• Large single-family houses with deep lots

• Victorian and early 20th-century architecture

The Chestnut Hill Historic District is listed on the National Register of Historic Places, and side streets are known for manicured gardens and mature trees.

Parks, Trails & Wissahickon Valley

You’re minutes from:

• Wissahickon Valley Park – miles of hiking, biking, and bridle trails

• The Wissahickon Creek gorge, with dramatic scenery and stone bridges

• Neighborhood playgrounds and green spaces

It’s rare to get this much nature while still being in the city.

Easy Access to Center City

Chestnut Hill has two SEPTA regional rail lines (Chestnut Hill East and West) that connect directly to Center City, plus nearby access to major roadways. That makes it a favorite for people who want suburban feel, city address.

Types of Chestnut Hill Houses

You’ll see a mix of:

• Stone single-family homes on quiet streets

• Twins & rowhomes closer to the avenue

• Large estates tucked away on winding roads

• Occasional newer construction infill homes

Each home has its own quirks, history, and personality—part of the fun is finding the one that fits you.

Buying a House in Chestnut Hill: My Process

1. Strategy Call

We’ll talk about:

• Your budget and financing

• Commute and lifestyle priorities

• How important walkability vs. lot size is to you

• Whether historic charm or low-maintenance is more your thing

From there, I set up targeted searches that focus on your version of Chestnut Hill.

2. Neighborhood & Micro-Location Match

Chestnut Hill isn’t huge, but micro-location matters:

• Close to Germantown Ave vs. quieter side streets

• Near train stations vs. tucked deeper into the neighborhood

• Proximity to the Wissahickon, schools, and parks

I’ll help you understand the pros and cons of each pocket so your shortlist actually makes sense.

3. Smart Tours (In-Person or Virtual)

We’ll tour:

• In person when you’re local

• Via live video if you’re relocating and can’t always be here

I’ll point out both the “wow” factors and the not-so-pretty details (age of systems, potential restoration, future resale).

4. Offers That Respect the House and Your Budget

Chestnut Hill homes are unique; pricing isn’t cookie-cutter. I’ll help you:

• Understand what comparable homes really sold for

• Decide when to be aggressive and when to wait

• Structure inspection and appraisal contingencies intelligently

You’ll never be pushed to “just offer more” without understanding why.

5. From Accepted Offer to Move-In

Once you’re under contract, I’ll coordinate:

• Inspections and any repair negotiations

• Appraisal and mortgage milestones

• Title, insurance, and closing logistics

You get clear updates and guidance, not radio silence.

Thinking About Selling a House in Chestnut Hill?

Sell Your Chestnut Hill House for Maximum Exposure

If you already own in Chestnut Hill and you’re thinking about selling, I can help you:

• Price your home based on current demand for historic and luxury houses

• Decide which prep projects are worth doing (and which are not)

• Market your home to local buyers and out-of-town buyers who are specifically hunting for Chestnut Hill and the Wissahickon area

Relocating to Chestnut Hill from Outside Philadelphia?

Many buyers come from:

• Center City / other Philly neighborhoods

• Main Line suburbs

• New York / North Jersey

• Out of state

I can help with:

• Area orientation (Chestnut Hill vs. nearby neighborhoods- Glenside, Oreland, Flourtown)

• Commute expectations and train options

• Coordinating a sale + purchase if you have a home to sell first

We’ll create a realistic game plan so you’re not rushed or overwhelmed.

Ready to Start Looking at Houses in Chestnut Hill?

If you’re even thinking about buying or selling a house in Chestnut Hill, the best next step is a quick conversation.

Tell me what “home” looks like to you, and I’ll send over a curated list of Chestnut Hill houses for sale that actually match your life—not just a random feed of listings.