A comfortable retirement in Highland Park typically requires $140,000-$190,000/year for a couple. Lake County property taxes on typical Highland Park retiree homes ($650K-$1.2M) commonly run $13,000-$25,000/year, generally lower than equivalent Cook County properties. Most Highland Park retirees need $2.3-$4.0 million in invested assets at retirement.
Highland Park is one of the larger and more established North Shore communities, with housing stock ranging from modest mid-century homes to substantial historic properties along Sheridan Road and the lakefront. Median home value of $550K reflects this range, but the typical retiree home in established neighborhoods is $700K-$1.2M with corresponding property tax of $14K-$25K annually.
The Lake County tax structure is generally favorable vs Cook County, same Illinois state tax exemptions on retirement income, but property tax rates roughly 10-15% lower than equivalent Cook County properties. For a $900K home, the savings vs Cook County might be $2K-$4K/year, meaningful over a 30-year retirement.
Healthcare is excellent: NorthShore Highland Park Hospital is in the community, Lake Forest Hospital and Evanston Hospital are nearby. Pre-Medicare couples typically spend $22K-$32K on private insurance; Medicare couples spend $9K-$14K. The Ravinia Festival, Highland Park Library, and Park District facilities are major lifestyle assets that attract retirees and add quality of life beyond what spending alone reflects.
Key facts
- Median Highland Park home: ~$550K; established retiree homes commonly $700K-$1.2M
- Property tax: typically $13K-$25K/year, somewhat lower than Cook County equivalents
- Pre-Medicare healthcare (couple): $22K-$32K/year
- Post-Medicare healthcare (couple): $9K-$14K/year
- Estimated portfolio needed at retirement: $2.3M-$4.0M
- Lake County: lower property tax than Cook for comparable property; same favorable IL retirement income tax treatment
Is Highland Park cheaper than Wilmette or Winnetka for retirement?
Generally yes, particularly on property tax. Highland Park's Lake County location reduces property tax by 10-15% vs equivalent Cook County properties. Median home values are also lower in Highland Park than Winnetka ($1.6M+) or Wilmette ($800K+). The cost difference can be $5K-$15K/year in property tax alone, plus the difference in housing cost if downsizing or moving in. Highland Park offers comparable amenities (Ravinia, lakefront, strong schools, established community) at meaningfully lower carrying cost.
