Skip to main content

Chestnut Hills Homes in Gerton with Preserve Trail Access

Chestnut Hills in Gerton has the feel of a tucked-away mountain cottage enclave, where winding lanes, wooded lots, and long views set the tone from the start.

Active
3
Recently Sold
25

Active & Pending Listings

About Chestnut Hills

Community overview based on MLS listing data for Chestnut Hills, Gerton

First Impressions

Chestnut Hills in Gerton has the feel of a tucked-away mountain cottage enclave, where winding lanes, wooded lots, and long views set the tone from the start. The neighborhood sits in the Hickory Nut Gorge area, with winter mountain views, mature hardwoods, rhododendron, and a landscape that feels closely tied to the surrounding ridgelines and trails.

"A vintage mountain retreat with trail access, wooded privacy, and an unmistakable cottage-country character."

Home Styles & Community Feel

The homes here lean classic and character-rich rather than uniform. Many properties are vintage cottages and cabins from the 1920s through the 1950s, with some later mountain homes mixed in. Wood interiors, stone fireplaces, screened porches, rocking-chair porches, and updated kitchens show up often, and several homes also offer flexible lower levels, workshops, or guest space. Lot sizes tend to be generous for a mountain setting, with wooded acreage, sloping ground, and occasional creek frontage adding to the sense of seclusion. It is the kind of place where older architecture and newer updates coexist comfortably.

Amenities & Daily Rhythm

Chestnut Hills has a community fishing pond, a large commons area, and access to hiking right nearby, including the Wildcat Rock and Florence Preserve trail systems. Some listings also point to a community center, pavilion, and library, which gives the neighborhood a small, gathered-around-the-common-space rhythm. Short-term rentals are allowed in at least some community remarks, and Spectrum high-speed internet is available, which broadens how owners use the homes. The overall pace feels shaped by porches, trail time, and mountain views rather than dense development.

"Porches, trails, and a shared pond give the neighborhood its everyday mountain rhythm."

Location & Schools

Chestnut Hills sits along the Chestnut Hill Road, Chestnut Hill Loop, Thomasville Lane, and Thomasville-adjacent roads in Gerton, with the community positioned between Asheville and Hendersonville. Public remarks place Asheville about 20 to 25 minutes away, Hendersonville about 30 to 35 minutes away, Lake Lure and Chimney Rock around 15 to 20 minutes away, and grocery, post office, and bank access about 12 minutes out. Nearby destinations include Bearwallow Mountain, the Upper Hickory Nut Gorge Trailhead, Bearwallow Creek, Bear Wallow Preserve Trail, Florence Preserve, Wildcat Rock, Chimney Rock State Park, and Lake Lure. School assignments are Edneyville Elementary, Apple Valley Middle, and North Henderson High, placing the community within a familiar Henderson County school pattern.

Questions about Chestnut Hills?

Palmetto Park Realty Team · Gerton

Ask about Chestnut Hills — we answer fast

Own a home in Chestnut Hills?

See what it's worth — your home's own sale history plus recent Chestnut Hills sales, free.

What's my home worth?

Nearby Communities

Communities similar to Chestnut Hills

Recently Sold in Chestnut Hills 25 recently sold in Chestnut Hills, Gerton with dates and property details

Recently Sold

25 recently sold in Chestnut Hills, Gerton

Property Sold Sold Price Days on Market Size Sold to Ask Sold $/SF
85 Chestnut Hill Road sold home in Gerton, SC 85 Chestnut Hill Road 3 bd · 2 ba Jun 8 2026 $435,000 39 1,256 sq ft 100.0% $346
220 Bearwallow Subdivision Road sold home in Gerton, SC 220 Bearwallow Subdivision Road 3 bd · 1 ba Jul 22 2022 $308,000 42 1,440 sq ft 94.8% $214
427 Chestnut Hill Loop sold home in Gerton, SC 427 Chestnut Hill Loop 2 bd · 2 ba Apr 13 2022 $365,000 34 1,110 sq ft 104.3% $329
163 Chestnut Hill Road sold home in Gerton, SC 163 Chestnut Hill Road 2 bd · 2 ba Sep 16 2021 $245,000 43 1,283 sq ft 103.4% $191
471 Chestnut Hill Loop Road sold home in Gerton, SC 471 Chestnut Hill Loop Road 3 bd · 3 ba Jun 15 2021 $700,000 40 2,890 sq ft 100.7% $242
106 Chestnut Hill Road sold home in Gerton, SC 106 Chestnut Hill Road 3 bd · 2 ba Apr 16 2020 $301,000 267 1,450 sq ft 94.4% $208
45 Thomasville Lane sold home in Gerton, SC 45 Thomasville Lane 3 bd · 2 ba Mar 12 2020 $190,000 223 1,880 sq ft 95.2% $101
85 Chestnut Hill Road sold home in Gerton, SC 85 Chestnut Hill Road 3 bd · 2 ba Feb 13 2020 $298,000 138 1,256 sq ft 93.4% $237
220 Bearwallow Subdivision Road sold home in Gerton, SC 220 Bearwallow Subdivision Road 3 bd · 1 ba Sep 24 2019 $171,000 64 1,440 sq ft 100.6% $119
284 Chestnut Hill Loop Road sold home in Gerton, SC 284 Chestnut Hill Loop Road 2 bd · 2 ba Dec 20 2018 $170,000 36 1,328 sq ft 97.1% $128
57 Chestnut Hill Road sold home in Gerton, SC 57 Chestnut Hill Road 2 bd · 2 ba Nov 20 2017 $184,000 60 1,220 sq ft 94.6% $151
72 Chestnut Hill Road sold home in Gerton, SC 72 Chestnut Hill Road 2 bd · 1 ba Jan 10 2017 $205,000 481 1,344 sq ft 91.1% $153
101 Windfall Circle #04,05 sold home in Gerton, SC 101 Windfall Circle #04,05 3 bd · 3 ba Nov 29 2016 $269,000 53 2,333 sq ft 96.4% $115
107 Chestnut Hill Road Lot 7, PT 5&8 sold home in Gerton, SC 107 Chestnut Hill Road Lot 7, PT 5&8 3 bd · 2 ba Jul 5 2016 $325,000 34 1,856 sq ft 98.8% $175
264 Chestnut Hill Road 2,3,4 & 5 G sold home in Gerton, SC 264 Chestnut Hill Road 2,3,4 & 5 G 2 bd · 2 ba May 19 2016 $154,000 66 956 sq ft 102.7% $161
95 Chestnut Hill Road sold home in Gerton, SC 95 Chestnut Hill Road 2 bd · 1 ba Mar 11 2016 $139,000 121 812 sq ft 99.4% $171
000 Chestnut Hill Loop sold home in Gerton, SC 000 Chestnut Hill Loop Mar 11 2016 $125,000 114 83.5%
57 Ne Chestnut Hill Road sold home in Gerton, SC 57 Ne Chestnut Hill Road 2 bd · 2 ba Nov 30 2015 $100,000 142 1,122 sq ft 83.3% $89
300 Chestnut Hill Loop Rd sold home in Gerton, SC 300 Chestnut Hill Loop Rd 3 bd · 2 ba Oct 30 2015 $130,000 373 1,092 sq ft 96.3% $119
45 Thomasville Lane sold home in Gerton, SC 45 Thomasville Lane 3 bd · 2 ba Dec 19 2014 $147,500 277 1,880 sq ft 86.8% $78
33 Thomasville Lane sold home in Gerton, SC 33 Thomasville Lane 1 bd · 1 ba Nov 3 2014 $70,000 24 557 sq ft 88.1% $126
147 Chestnut Hill Road sold home in Gerton, SC 147 Chestnut Hill Road 3 bd · 3 ba Feb 20 2014 $178,000 308 3,425 sq ft 79.1% $52
238 Chestnut Hill Road sold home in Gerton, SC 238 Chestnut Hill Road Nov 25 2013 $8,000 189 50.3%
45 Thomasville Lane sold home in Gerton, SC 45 Thomasville Lane 2 bd · 2 ba Oct 4 2013 $91,000 15 1,462 sq ft 92.4% $62
85 Chestnut Hill Road sold home in Gerton, SC 85 Chestnut Hill Road 3 bd · 2 ba Aug 14 2012 $204,000 53 1,243 sq ft 94.9% $164

Market Trends

Closed sales from MLS history for Chestnut Hills, Gerton

Below trend-line threshold — city median shown for context

$100k $200k $300k $400k 20222023202420252026 $287k Gerton Sales closed per quarter peak 1

The Chestnut Hills real estate market shows buyer's market conditions. Homes typically sell within 65 days. With 3 active listings and 1 home sold in the past year, buyers have more negotiating power and time to decide.

Pricing

Median Price
$535,000
Average Price
$389,667
$/Sq.Ft (Q1)
$116

Property Details

Avg Bedrooms
2.6
Avg Bathrooms
2.0
Avg Lot Size
0.58 acres

Market Activity

Active Listings
3
Sold Last Year
1
Median Days to Sell
65 days

Community Info

Median Year Built
1950
New Construction
0%

Recently Off Market Properties

Listings taken off the market in the past year in Chestnut Hills, Gerton

1 property
Looking for similar properties?

These homes are no longer available, but they show recent pricing and listing activity in Chestnut Hills. Our agents can help you watch for new listings in this area.

Contact an agent
Call Map

Add a place

Listing alerts

Save this search

Choose a name and how often you want new-match alerts.

You can remove alerts any time from Saved searches.