Located on the corner of Jefferson Park Avenue and Brandon Avenue near the UVA hospital compound in front of a bus-stop, Elson Student Health is readily accessible by bus or via a 5-10min walk from central grounds.

UVA Health System
http://www.healthsystem.virginia.edu/home.html
This includes the UVA Hospital/Medical Center, Emergency Room, School of Medicine, School of Nursing, and Health Sciences Library. While Student Health usually takes care of student needs, referrals may be made to the UVA Medical Center if deemed necessary.

Medicine
Many kinds of commonly used medicines, such as lozenges for sore-throat, panadol-type medications for headaches and fever, or flu medication, are available on the shelves at all local supermarkets in Charlottesville, Wal-Mart, as well as at CVS pharmacy outlets located both on Route 29 and Downtown. All of these stores have their own pharmacies where you can obtain prescription medicine, if needed. On-grounds, you can also get basic medication from the UVA Bookstore and all on-grounds convenience stores in addition to at Student Health or the UVA Hospital.

Immunizations
http://www.virginia.edu/studenthealth/NS_StudentInfo.html
http://www.virginia.edu/studenthealth/NSChecklist.html
A list of required vaccinations will be stated in the Pre-Entrance Health Form snail-mailed over to you sometime June-July. While it is possible to get these injections at the vaccination clinic held at the start of every school year, or at the UVA Student Health Center, it may be a lot more economical to get your jabs done in Singapore, where healthcare costs are considerably lower.

UVA generally require the following vaccinations: Measles-Mumps-Rubella (MMR), Hepatitis B, Meningococcal meningitis. Tuberclosis screening is also a must, and you will need to get a chest X-ray done in addition to having your BCG records from primary and secondary school.

Do make sure your health records fulfill these requirements before semester starts, otherwise you will be blocked from course registration!

Alternatively, you can get all your shots for free should the insurance you purchase here in the US covers it. I know for a fact that the Chickering plan covers all immunizations taken at student health.

Health Insurance
http://www.virginia.edu/studenthealth/insurance.html
Since health care costs are high in the US, all UVA students must have health insurance. How this works out is that the student would pay a portion of the fees incurred for a visit to the doctor’s (the “co-payee” fee), and the insurance policy would cover the rest of it. The insurance company will usually issue you a health insurance card, which you should carry in your wallet so that you can quote the policy number when settling medical payment.

In the past, for convenience’s sake, many UVA students purchase the default health insurance policy from The Chickering Group, an insurance company that has been the official health insurance provider at UVA for a number of years.

However, the Chickering plan often comes up to being rather expensive, and some other more affordable options you may want to consider are: getting health insurance online at websites like www.isoa.org. Look at the compass gold plan. Its the only one that satisfies the standards which UVA emplaces upon its students. But its a good 1/3 cheaper than damn chickering. (disclaimer, bitterness is evident from the author due to his being swindled off 1200 USD via chickering)

Health insurance policies can differ greatly, so when comparing policies, do look out for the "co-payment" or "co-payee" fees, as well as the kind(s) of insurance coverage and extent of coverage offered. Not all plans come along with dental insurance or eye-care insurance, and it would probably be a good idea take special note of this.

But as a guideline, a majority of Singaporeans seem to have chosen the compass gold plan. Also if you're currently under a plan in Singapore, check if your plan is similar to chickering, and if it is then you might be able to avoid dealing with insurance altogether if you manage to submit proof of this insurance to UVA.