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Jackson Park Highlands Real Estate and Neighborhood Information

Get to know Jackson Park Highlands

Jackson Park Highlands, one of the most historic and attractive neighborhoods in the south side of Chicago, is situated in a small pocket of the larger South Shore community that rests next door to scenic Jackson Park. Beautiful Victorian era mansions are commonplace in Jackson Park Highlands. Instead of tightly-packed rows of houses, these grand homes are spread out atop oversized green grass lots with matured trees and privacy hedges separating the properties even more. Not all real estate in Jackson Park Highlands is up market, there are also very nice mid-century split-levels and redbrick courtyard condominiums that provide ample living space for couples and families with smaller budgets.

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Jackson Park Highlands Real Estate

As a result of its historically exclusive status, today the tree-lined residential streets of Jackson Park Highlands offer some of Chicago’s largest and most attractive properties in the city. Of course, with the prestige of living in such an elegant neighborhood, homebuyers can expect the real estate here to be some of the more expensive on the south side.

The immense detached single-family dwellings that sit on large green lots are most common in the neighborhood, although several low-rise condo and apartment buildings were erected in the area in the 1950s and ‘60s. The main multi-unit residential buildings are mostly along Jackson Park Highlands’ wide border thoroughfares. The massive vintage-style, redbrick courtyard condominiums typically offer one-, two-, and three-bedroom units that range in price from to the mid $100,000s to the low $200,000s.

Several of Jackson Park Highlands’ beautiful houses, built in the early 1900s, would be considered mansions by today’s standards and continue to maintain the awe-inspiring grandeur. One of the great design approaches used by the architects of the neighborhood’s residences of the time period was to construct these homes set back on 50-foot-wide plots of land leaving generous front lawn space and room for faultlessly trimmed hedges and wrought-iron front gates. Such features were innovative at the time, and were later incorporated into typical suburban neighborhood planning. Other infrastructural advancements enjoyed by the residents of Jackson Park Highlands back in its emergence were the use of underground utilities and—most notably—it is one of the only Chicago neighborhoods that doesn’t have alleys between streets.

There is a wide variety of homes in the Jackson Park Highlands that span from towering three-story Victorians with room-size pillared porches and back garages to more modern split-levels with attached garages. All in all, the properties in this once elite south side Chicago neighborhood are impressively magnificent with a timeless charm that persists throughout the years. Detached single-family houses in Jackson Park Highlands start in the low $300,000s, but the price tag for many of these century-old homes can easily be in the $700,000 or $800,000 range.


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