442 Wayside Dr, Winston Salem, NC 27107
Property image
Property image
SOLD
JUN 5, 2026

442 Wayside Dr
Winston Salem, NC 27107

  • 4 Beds
  • 2 Baths
  • 3,300 sqft (on 0.28 acres)

$50,000

Last Sold: Jun 5, 2026
$15/sqft
Est. Refi. Payment $360/mo*
Refinance Your Home

$50,000

Last Sold: Jun 5, 2026
$15/sqft
Est. Refi. Payment $360/mo*
Refinance Your Home
4 Beds
2 Baths
3,300 sqft
(on 0.28 acres)

Home Value

Trulia Estimate
$50.2K
Since last month
$0 (0%)
Since last year
Decreased$213K (-81%)
Since last sale
Increased$100 (+0.2%)
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 decreased by -62% in the last 10 years
MonthEstimated value
2026
August 2026$50K
July 2026$50K
June 2026$50K
May 2026$206K
April 2026$196K
March 2026$197K
February 2026$204K
January 2026$198K
2025
2024
2023
2022
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
301 Bedford Park Dr, Winston Salem, NC
0.05
Single-Family Home
$235,000
11/20/25
3
2
1,420
307 Wayside Dr, Winston Salem, NC
0.30
Single-Family Home
$77,500
10/30/25
2
2
1,139
449 Bedford Knoll Dr, Winston Salem, NC
0.22
Single-Family Home
$248,000
09/12/25
4
2.5
1,944
467 Bedford Knoll Dr, Winston Salem, NC
0.32
Single-Family Home
$200,000
04/29/26
3
2
1,618
250 Water Lily Cir, Winston Salem, NC
0.37
Single-Family Home
$341,750
09/24/25
4
2.5
2,346
313 Water Lily Cir, Winston Salem, NC
0.31
Single-Family Home
$300,000
07/02/26
4
2.5
2,138
176 Wayside Dr, Winston Salem, NC
0.42
Single-Family Home
$100,000
05/14/26
4
2
2,886
14 Jayson Ln, Winston Salem, NC
0.35
Single-Family Home
$339,000
08/21/25
4
3
1,814
237 Brooks Edge Dr, Winston Salem, NC
0.39
Single-Family Home
$283,500
09/15/25
3
2
1,831

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
301 Bedford Park Dr, Winston Salem, NC 27107
0.05
$235,000
3
2
1,420
Recently Sold
3630 Bedford Park Ct, Winston Salem, NC 27107
0.06
$285,000
4
2.5
1,835
Off Market
445 Wayside Dr, Winston Salem, NC 27107
0.04
$225,200
3
1
1,211
Off Market
3621 Evanston Way, Winston Salem, NC 27107
0.09
$251,500
3
2
1,564
Off Market
3602 Evanston Way, Winston Salem, NC 27107
0.08
$231,900
3
1
1,192
Off Market
262 Farmingdale Ave, Winston Salem, NC 27107
0.12
$284,100
4
2.5
1,601
Off Market
262 Farmingdale Ave #10, Winston Salem, NC 27107
0.13
-
-
-
-
Off Market
490 Wayside Dr, Winston Salem, NC 27107
0.13
$100,500
2
1
828
Off Market
501 E Wayside Dr, Winston Salem, NC 27107
0.15
$123,400
2
1
725
Off Market
448 Bedford Park Dr, Winston Salem, NC 27107
0.14
$301,700
4
2.5
2,024
Off Market
436 Bedford Park, Winston Salem, NC 27107
0.17
$220,400
3
2
1,175
Off Market
225 Farmingdale Ave, Winston Salem, NC 27107
0.22
$241,300
3
2
1,275
Off Market

Local Information

  • Map ViewExplore the area around 442 Wayside Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1935
Lot Size
0.28 acres
Living Area
3,300 sqft
Price/Sqft
$15/sqft

About this House

CASH ONLY SALE! Make an offer! This home will be a great flip home for an investor or add your personal touches and make it your personal home. Tons of SF and possibilities in this home but there is NO heating or A/C so it will need to be a cash sale only! Brick Front! Tons of space, there is two brs & full bath on the main, Huge Bonus is located up stairs w/a deck off the front & back, could be used as a primary br if a closet was added to the space, tile floors on main in kit, dining, bathroom & living room. Large den upstairs that separates the two brs, would be ideal if someone had extended guest staying over or just need privacy spaces in your home. Bay window in Den upstairs & DR, The home needs a total rehab, cleaning up but will make a great home or perfect for a investor. Lots of potential & open spaces, Great location, minutes from downtown Kernersville or Winston Sold "AS IS" buyer to verify info. AGENTS "READ!" AGENT ONLY remarks, NO assignment sales.
442 Wayside Dr, Winston Salem, NC 27107 is a 4 bedroom, 2 bathroom, 3,300 sqft single-family home built in 1935. It last sold for $50,000 on Jun 5, 2026. It is currently off market. The Trulia Estimate is $50,200, with a rent estimate of $1,853/month.

Home Details for 442 Wayside Dr

Interior Features

Heating & Cooling
Heating: Forced AirHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 9
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Brick

Property Information

Year Built
Year Built: 1935
Property Type / Style
Property Type: Single Family HomeArchitecture: conventional

Price & Status

Price
Price Per Sqft: $15/sqft

Community

Units in Building: 1

Lot Information

Lot Area: 0.28 acres

Price and Tax history

DateEventPrice
Jun 5, 2026
Source: N/A
Sold
$50,000
Feb 21, 2023
Source: RE/MAX International
ListingRemoved
Sep 29, 2022
Source: Triad MLS #1082530
PriceChange
$189,900
Price decreased by 5%
Aug 31, 2022
Source: Triad MLS #1082530
Listed For Sale
$199,900
Jul 1, 2005
Source: N/A
Sold
$35,000

Market trends in Winston-Salem

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$272K
$4.17KMoM
Sale-to-List Price
99.1%
Price per sq ft
$167
$2MoM
Available listings
1086
38MoM

Around this home

What Locals Say about Winston-Salem

At least 1046 Trulia users voted on each feature.

  • 86 % Say car is needed

  • 80 % Say parking is easy

  • 79 % Say it's dog friendly

  • 74 % Say yards are well-kept

  • 72 % Say there's holiday spirit

  • 64 % Say kids play outside

  • 62 % Say it's quiet

  • 55 % Say people would walk alone at night

  • 53 % Say streets are well-lit

  • 52 % Say neighbors are friendly

  • 49 % Say there's wildlife

  • 48 % Say they plan to stay for at least 5 years

  • 47 % Say there are sidewalks

  • 41 % Say it's walkable to grocery stores

  • 35 % Say it's walkable to restaurants

  • 28 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "Great neighborhood. "
    0
    Flag
  • Yybq4h9nxz
    "Easy access to downtown, schools and highway for longer commutes. Can walk to some locations, like the park some schools and shops."
    0
    Flag
  • Hannah Frey
    "Most of my neighbors have dogs so this neighborhood is very dog friendly so there’s nothing any dog owners would hate"
    0
    Flag
  • Lydia Acety
    "It’s a long commute but it’s like an adventure and the buses run great around here and the neighborhood is very quiet been here for 2 yrs and wouldn’t change it hope to be here longer"
    0
    Flag
  • Whgf2dztq6
    "Best little big town there is. I live in West End / downtown and plenty to do within walking distance every weekend."
    0
    Flag
  • Jon
    "Near schools but also near transitional neighborhoods and also million dollar homes Lots of walkers "
    1
    Flag
  • Maria Coleman
    "It’s a brand new subdivision that’s very diversified. It’s always clean and the children get along great!!!"
    0
    Flag
  • Bessy Garcia
    "In the area that I live in the public transportation is at least a mile away. The neighbors are very friendly and always greet you. It is very pet friendly as well."
    0
    Flag
  • B69yzy4bvf
    "It was easy commute with great experience and great service to the neighborhood great people. Easy access to transportation "
    0
    Flag
  • Tqmgnr6c7w
    "Everything about Winston salem is unique. The buildings , the people the environment . Everything is perfect "
    0
    Flag
  • Lydia Acety
    "I lived in this neighborhood for one year it is a very tranquil area the neighbors are nice. The atmosphere is very nice."
    0
    Flag
  • Jon
    "Annual July 4 celebration and Christmas street lighting School system events like basketball, football and baseball "
    0
    Flag
  • Nicole Cofield
    "Lots of people have dogs in the neighborhood, but many are not leashed or contained within electric or standard fences. "
    0
    Flag
  • Trulia User
    "Mostly small businesses and medical care facilities but there is some of us that stay here that have small homes that are usually single family homes but great area and safe and clean. "
    0
    Flag
  • Jon
    "July 4th picnic Candles on road at Christmas Friendly block parties Good neighbors Annual Christmas party "
    0
    Flag
  • Prophetharvey21
    "Dog owners would like the closeness to downtown and the walkways downtown. Dog owners would not like that this neighborhood is home to shootouts and drive-bys"
    0
    Flag
  • Cjswife2
    "The area is quiet and family friendly while there isn’t a park in my neighborhood there are parks , outdoor rec spaces very close to take the kids and play ,walk, hike boat or fish "
    0
    Flag
  • Mary Peterson
    "Homeless and drunks frequently walk back and forth between 1st St and the YMCA. The park area and West End in general has become increasingly dangerous over the past couple years. "
    0
    Flag
  • Trulia User
    "I am not sure what is important. I think it is safe. There appears to be a good neighborly vibe in the neighborhood. "
    0
    Flag
  • Trulia User
    "There are lots of dog owners in the neighborhood. Many nice areas to walk your dog and friendly neighbors."
    0
    Flag
  • Trulia User
    "safety is the most important keep your kids safe and comfortable comfortability is a big must for the most part "
    0
    Flag
  • Trulia User
    "Most people let their dogs run loose and people speed up and down the street and there’s always shooting."
    3
    Flag
  • Trulia User
    "Neighborhood appears well kept, houses are nice and people seem friendly. The little are where there are businesses seems nice as well."
    0
    Flag
  • Trulia User
    "very dog friendly! only problem is two busy roads but fine as long as they're leased and kept an eye on!"
    0
    Flag
  • Trulia User
    "Elementary and Middle School events. There is a neighborhood swimming pool. there's a pop warner football team that practices at the school."
    0
    Flag
  • Trulia User
    "Convenient to drive just about anywhere, stores, doctors, etc. Most neighbors keep to themselves. I wouldn’t feel safe walking at night but do in the daytime. "
    1
    Flag
  • Trulia User
    "it's great and pretty and very convenient for day to day living. pet friendly and generally safe. "
    0
    Flag
  • Trulia User
    "lots of traffic in the area, Calvary has a day school if desired. "
    0
    Flag
  • Trulia User
    "I love my neighbors here. It is a very safe and quiet neighborhood. We love that everyone watches out for everyone got cameras!!"
    0
    Flag
  • Trulia User
    "Nothing at all, it can be a lot of improvement to the neighborhood. like speed bumps, cars are going fast."
    0
    Flag
  • Trulia User
    "I've lived in this neighborhood most of my life. It's home. People still show respect towards each other here. "
    0
    Flag
  • Selena S.
    "Very nice 😊 lace to leave but nothing for kids to do. They use to put up the basketball goals and then take it down if too many kids gathered. pool excellent size. keep in mind it’s older neighborhood and lot of the owners and HOA members frown upon the renters"
    1
    Flag
  • Trulia User
    "Park there's a Quarry Park, golf course, and recreation center all on in the same location. real The recreation center has playgrounds, grills,tennis court, basketball court (inside and outside), a shelters, and a swimming pool. The lake is down the street. You can also fish as well. There's a trail that goes around the lake and pass the golf course."
    3
    Flag
  • Trulia User
    "I drive everywhere that I go. There's several hwy around here, and it's close to Peter's Creek Pkwy, south park shopping center and Hanes mall. "
    0
    Flag
  • Trulia User
    "Love living downtown next to restaurants and other fun things. Most thing are within walking distab l"
    0
    Flag
  • Trulia User
    "There are many families in the neighborhood and it makes it feel like home, specially in the summer time."
    1
    Flag
  • Trulia User
    "Afternoon backyard talks, watching out for each other’s pets and kids on the street, and proximity to wake forest soccer games. "
    0
    Flag
  • Trulia User
    "Swim meets at the town pool. Community group that keeps up with the signage at our entrances. It's just a nice area to walk around in. "
    0
    Flag
  • Adam S.
    "Ardmore is a great community. People are always out and about, walking dogs, getting coffee; grabbing groceries... everything is so accessible and being so close to Miller Park is amazing too. "
    3
    Flag
  • B G.
    "No know community events in the immediate area, however just a few miles down Country Club Rd in Lewisville there is a farmers market as well as a community flea market on the weekends during the warmer months of the year."
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 442 Wayside Dr

  • What is 442 Wayside Dr estimated to be worth?
    Trulia's estimated value for 442 Wayside Dr in Winston Salem, NC is $50,200.
  • What is the price history for 442 Wayside Dr?
    442 Wayside Dr in Winston Salem, NC last sold for $50,000 in June 2026.
  • Is Winston Salem a buyer's or seller's market?
    Winston Salem is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Winston Salem?
    The median sale price in Winston Salem is $272K. That is up $4.17K from the prior month.
  • How big is the lot at 442 Wayside Dr?
    The lot at 442 Wayside Dr in Winston Salem, NC is about 0.28 acres (12,196 sq ft).

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