535 E Chestnut Gap Rd, Hendersonville, NC 28792
Property image
Property image
OFF MARKET

535 E Chestnut Gap Rd
Hendersonville, NC 28792

  • 3 Beds
  • 3.5 Baths
  • 2,954 sqft

$917,500

Trulia Estimate
as of Aug 20, 2026
Est. Refi. Payment $5,153/mo*
Refinance Your Home

$917,500

Trulia Estimate
as of Aug 20, 2026
Est. Refi. Payment $5,153/mo*
Refinance Your Home
3 Beds
3.5 Baths
2,954 sqft

Home Value

Trulia Estimate
$918K
Since last month
Increased$34K (+3.8%)
Since last year
Increased$133K (+16.6%)
Since last sale
Increased$605K (+183.3%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +244% in the last 10 years
MonthEstimated value
2026
August 2026$935K
July 2026$901K
June 2026$925K
May 2026$921K
April 2026$903K
March 2026$910K
February 2026$753K
January 2026$726K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
321 Benjamins Way #48, Hendersonville, NC
0.53
Single-Family Home
$579,000
10/27/25
3
2
1,960
410 Rockwood Dr, Hendersonville, NC
0.83
Single-Family Home
$525,000
03/16/26
3
3
2,922
227 Sean Way, Hendersonville, NC
0.65
Single-Family Home
$540,000
09/12/25
3
2
2,210
121 Rockwood Dr, Hendersonville, NC
0.72
Single-Family Home
$380,000
08/25/25
3
2
1,240
112 Chestnut Ln, Hendersonville, NC
0.96
Single-Family Home
$410,000
07/13/26
3
2
1,797
201 Chestnut Gap Rd, Hendersonville, NC
0.47
Single-Family Home
$3,500
04/29/26
4
3
1,680
406 Prestwood Ln, Hendersonville, NC
1.16
Single-Family Home
$600,000
01/29/26
3
3.5
2,620
42 Wild Pheasant Run, Hendersonville, NC
1.08
Single-Family Home
$515,000
10/08/25
3
2
2,038
73 Montchannin Hts, Hendersonville, NC
1.13
Single-Family Home
$497,000
11/04/25
3
2
1,639
39 Creekwalk Ln, Hendersonville, NC
1.26
Single-Family Home
$469,999
08/29/25
3
2
2,028

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
519 Chestnut Gap Rd, Hendersonville, NC 28792
0.39
$695,700
3
3.5
4,584
Off Market
149 Cold Springs Rd, Hendersonville, NC 28792
0.42
$699,000
3
3
2,629
Off Market
112 Lynn Estate Rd, Hendersonville, NC 28792
0.44
$320,000
3
2
2,032
Recently Sold
172 Cold Springs Rd, Hendersonville, NC 28792
0.45
$709,700
3
2.5
2,020
Off Market
31 Kayla Susan Rd, Hendersonville, NC 28792
0.48
$312,600
3
2
1,620
Off Market
153 Hackleburg Ln, Hendersonville, NC 28792
0.53
$475,000
3
3
1,495
For Sale
Ashton Ln, Hendersonville, NC 28792
0.55
-
-
-
-
Off Market
321 Benjamins Way #48, Hendersonville, NC 28792
0.53
$579,000
3
2
1,960
Recently Sold
/ Off Pace Rd, Hendersonville, NC 28792
0.58
-
-
-
-
Off Market
227 Sean Way, Hendersonville, NC 28792
0.65
$649,500
3
2
2,210
For Sale
660 Pace Rd, Hendersonville, NC 28792
0.70
$317,600
2
1.5
819
Off Market
529 Pace Rd, Hendersonville, NC 28792
0.71
$585,500
3
1
1,172
Off Market

Local Information

  • Map ViewExplore the area around 535 E Chestnut Gap Rd.
  • Schools1 Preschool School2 Elementary Schools1 Middle School2 High Schools
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1926
Living Area
2,954 sqft
Price/Sqft
$311

About this House

Discover a piece of history nestled on 9 acres of picturesque countryside that stands as a testament to timeless craftsmanship and architectural splendor. Located in a serene setting, this estate offers not just one, but three homes, each with its own unique charm and character. The centerpiece of this estate is the 1920s stone home, exuding vintage charm and modern allure. Stepping inside, you are greeted by spacious rooms adorned with original hardwood floors, large windows that invite natural light to dance across the living spaces and two grand fireplaces that serve as the heart of the home, perfect for cozy evenings and gatherings. The second home is an adorable, updated two bedroom carriage house with a large front porch overlooking the neighboring apple orchard. The third is an income producing short term rental that sits at the top of the gently sloping hill. This is a truly stunning, one-of-a-kind property looking for it's next custodian.
535 E Chestnut Gap Rd, Hendersonville, NC 28792 is a 3 bedroom, 4 bathroom, 2,954 sqft single-family home built in 1926. It last sold for $330,000 on Feb 15, 2008 (74% below the $1,250,000 asking price). It is currently off market. The Trulia Estimate is $917,500, with a rent estimate of $3,716/month.
Contact this Building
Property Website

Home Details for 535 E Chestnut Gap Rd

Interior Features

Heating & Cooling
Heating: Electric, Pellet StoveAir ConditioningCooling System: Central AirHeating Fuel: Electric
Appliances & Utilities
DryerRefrigerator

Property Information

Year Built
Year Built: 1926
Property Type / Style
Property Type: Single Family Home

Price and Tax history

DateEventPrice
Dec 20, 2024
Source: BHHS broker feed #4163215
ListingRemoved
$1,250,000
Sep 24, 2024
Source: Canopy MLS as distributed by MLS GRID #4163215
PriceChange
$1,250,000
Price decreased by 4%
Jul 27, 2024
Source: Canopy MLS as distributed by MLS GRID #4163215
Listed For Sale
$1,299,000
Feb 15, 2008
Source: N/A
Sold
$330,000

Market trends in Hendersonville

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$417K
$12.5KMoM
Sale-to-List Price
—
Price per sq ft
$250
$6MoM
Available listings
523
7MoM

Around this home

What Locals Say about Hendersonville

At least 251 Trulia users voted on each feature.

  • 86 % Say car is needed

  • 77 % Say it's dog friendly

  • 77 % Say yards are well-kept

  • 75 % Say there's holiday spirit

  • 75 % Say parking is easy

  • 69 % Say it's quiet

  • 64 % Say there's wildlife

  • 60 % Say people would walk alone at night

  • 53 % Say neighbors are friendly

  • 52 % Say they plan to stay for at least 5 years

  • 49 % Say kids play outside

  • 44 % Say streets are well-lit

  • 33 % Say there are sidewalks

  • 30 % Say there are community events

  • 29 % Say it's walkable to restaurants

  • 29 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Ron Layton
    "Neighborhood is about 26 years old, so have many older folks who are gradually moving out and being replaced with younger families. Very good middle and high schools within a mile of neighborhood."
    0
    Flag
  • Lblbpint
    "I actually live outside the city limits in a little town called Edneyville and it is very country with no sidewalks but beautiful."
    0
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  • Lblbpint
    "We moved here in 2017 from FL to get away from the heat and overcrowding. The beauty of the mountains and people here made this home!!!"
    0
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  • Valerie Mccord
    "Hendersonville quickly became my hometown. Very welcoming, kind people. Lots of resources, stores and parks available to most every part of Hendersonville that you visit. It’s also close to Asheville, which is just a fun, beautiful town lots of events and things to do there. I think my favorite thing in Hendersonville is probably the pinball museum. You pay one flat rate get a wristband and you can come and go as you please for the whole day right in the heart of downtown Hendersonville. "
    0
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  • Lblbpint
    "Annual Apple Festival! Lots of apple picking farms and fruit n veggie stands. Beautiful parks, hiking trails, and drives on the Blue Ridge Parkway."
    0
    Flag
  • Kerry Sinclair
    "Traffic moves fast on chimney rock road and there are some amber alerts. Otherwise it’s a safe neighborhood "
    0
    Flag
  • Hugh Kimbrough
    "Mountain proximity is a big feature here. Beautiful mountain town. Near Asheville. Price increases are the biggest drawback "
    1
    Flag
  • Trulia User
    "I live just outside this neighborhood and find the people and homes to be friendly. The main road, Balsam, is a through road and occasionally has speeding vehicles. Also, neighborhood does not have sidewalks."
    10
    Flag
  • Trulia User
    "yes we all have dogs my dogs I’ve never been happier anywhere else with picturesque mountain views, tall basking, trees, and kind, friendly neighbors. It’s a very positive natural beautiful environment to have your furry family members. The lots are large, so they have plenty of room to run around and play most houses here are fenced and private, which helps with barking when watching the passerby’s."
    1
    Flag
  • Trulia User
    "lived in two homes in the area since 2012. its been a good place to grow up in and find my own roots in. Neighbors are nice. roads are well taken care of even in snow and ice. there is always pretty fast service the few times we've lost power. lots of critters and pretty sights and really good eats nearby. the schools are all excelent. couldn't ask for a better area."
    7
    Flag
  • Trulia User
    "Neighborhood get togethers. Main Street parties, parades and special events. Apple festival and many excellent micro breweries. close to hospital and shopping and exercise. Great walking and bicycle trail. "
    4
    Flag
  • Trulia User
    "we've been here 35 years and there is just no place like it. quiet, beautiful lake, wildlife. it has it all! "
    0
    Flag
  • Trulia User
    "Quaint houses close to downtown and conveniences such as doctors, dental and grocery stores. I’m retired so I do not have to worry about commuting time. Traffic is generally light."
    2
    Flag
  • Mollybernard85
    "Very clean and quiet area. Hendersonville has amazing schools and downtown has a lovely charm. We have beautiful pumpkin patches setting up for Halloween. Beautiful community!"
    12
    Flag
  • Michelle B.
    "Best place to raise children. Very family orientated schools. family frendly place lots of apple farms , state park near by. lots of out door activities. "
    1
    Flag
  • Oz15071617
    "Most commutes require transportation if you get beyond the city. However there is public transportation in the city. City is very walkable or accessible by bike. Traffic is very light in off peak hours but very heavy during the day due to influx of tourists and workers from out of the area. Bigger chain stores still very accessible via interstate, probably within 15 to 30 minutes depending on destination (Arden, Skyland, Asheville or Greenville). "
    0
    Flag
  • Ivonne N.
    "There are many parks in our area with lots of families with children and pets. We love where we live and I hope you do too!"
    2
    Flag
  • Kellyatism
    "Great small town feel. Friendly people. Multicultural. Lots of farms. 2 good community hospitals and a level 1 trauma center close also. Lots of doctors and dentist. Fun, family oriented festivals and events downtown. Good restaurants and conveniences like Sams club and grocery stores. "
    7
    Flag
  • 12mustachio
    "occasionally Hendersonville will shut down the main street for events. Apple festival being the main one, but there is a lot of charm in this small town. "
    0
    Flag
  • Stephanie T.
    "Anderson county is a wonderful place to raise. I am raising my three grandkids in Henderson County and I love the school system. The community bands together for the good of each other. We attend church 10 minutes from my house they offer school daycare and a wanna"
    0
    Flag
  • Vonschummer
    "Nice quiet walkable neighborhood. Close to schools, churches, hospital etc. houses and lawns maintained. Close proximity to all conveniences such as big box hardware, multiple grocery stores to choose from. Only twenty minutes to the airport."
    4
    Flag
  • Trulia User
    "We look out for each other, and it’s a quite place. There’s a lot of nature, also. There are get together, though we haven’t attended. "
    1
    Flag
  • Unspecified
    "Love the feel of living in a town instead of a city. Really feel safe and comfortable living here. Would recommend raising a family or retiring here."
    1
    Flag
  • Ray A. C. B.
    "We have quite a few dog owners that walk them on a regular basis. There have been several on no leash, which could present a problem. It's not the dogs fault, just owners. "
    5
    Flag
  • Jennifer A.
    "People help each other out in this area. When it snows we all work together. When someone is sick we help them out."
    0
    Flag
  • Dawn D.
    "I see dogs sometimes. A lot of them are in fenced in back yard. I’ve only dogs loose seldom. Great area for dogs."
    0
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  • Dawn D.
    "It’s not as busy as Asheville. Pretty much anywhere you live in Hendersonville you’re able to access I26 very easily. Hendersonville has nice neighborhoods that are very safe."
    0
    Flag
  • Dawn D.
    "Great area for dogs, there’s even a dog park in some locations. Plus there’s plenty of sidewalks and trails that you can walk your dog. People usually always keep their dogs on leashes. I’ve never felt uncomfortable walking my dog in any neighborhood where I live."
    0
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  • Trulia User
    "Downtown offers many different events year round that can be enjoyed by all members of the community."
    1
    Flag
  • Nhoerman
    "We drive ourselves everywhere we go. There is a lot of traffic on 25 going into Hendersonville. Going into Blue Ridge Mall is usually wall to wall traffic. "
    5
    Flag
  • Erick.renteria92a
    "I love Hendersonville, always calm and I feel like a nice place for my kids , even now that I live at East Flat Rock ."
    0
    Flag
  • Cheri I.
    "They would love it here. There are many residents that have dogs and they are always out walking them. They all clean up after the dog too"
    0
    Flag
  • TeresaD
    "We purchased a home in Flat Rock Lakes two years ago. The neighborhood is beautiful and quiet with all lovely and unique homes."
    3
    Flag
  • Nadine
    "Well behaved dog!! And always clean up after immediately!’ My dog and I are very friendly yet respectful. I wish there were sidewalks and streetlights. And less traffic. "
    0
    Flag
  • Nelson I. C.
    "Very friendly and nice Recommended for a small family. very quiet place with nice people. "
    0
    Flag
  • Pattymcdowell80
    "Very quiet neighborhood with children at play and dogs barking. You are in the county but right across the street is Walmart and big Sam’s and all kinds of food places to choose from."
    1
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 535 E Chestnut Gap Rd

  • What is 535 E Chestnut Gap Rd estimated to be worth?
    Trulia's estimated value for 535 E Chestnut Gap Rd in Hendersonville, NC is $917,500.
  • What is the price history for 535 E Chestnut Gap Rd?
    535 E Chestnut Gap Rd in Hendersonville, NC last sold for $330,000 in February 2008.
  • Is Hendersonville a buyer's or seller's market?
    Hendersonville is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Hendersonville?
    The median sale price in Hendersonville is $417K. That is down $12.5K from the prior month.
  • Does 535 E Chestnut Gap Rd have air conditioning?
    Yes, 535 E Chestnut Gap Rd in Hendersonville, NC has air conditioning.

Explore by feature - Pet Friendly

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Off Market Homes Near 535 E Chestnut Gap Rd

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