5,000 Sq Ft Hyde Park Vintage Penthouse Now Just $299,500: 5490 S. South Shore


This 6-bedroom vintage penthouse in the Jackson Shore Apartments at 5490 S. South Shore in Hyde Park came on the market in May 2019.

Jackson Shore Apartments was designed by Rapp & Rapp in 1917. The Rapps mainly designed cinemas in the 1920s.

According to the Chicago Apartments, A Century of Lakefront Luxury, it was the first tall luxury building in East Hyde Park and had the largest units in the neighborhood.

The 12-story building has 20 apartments and a top floor that was meant to be servants quarters.

It’s most distinguishing feature are the cylindrically shaped windows on the north and south sides of the building which were designed to be orangeries (or “sunrooms” in todays parlance).

The 20 units were designed to be like single family homes and are over 5,000 square feet each.

It has a 24-hour doorman. There’s no parking but there is an exercise room and a private enclosed yard with grills.

The building remains a co-op.

If this building looks familiar, that’s because we last chattered about it in September 2019.

See our chatter here.

The listing says there are 6 bedrooms. On the original floor plan there were 4 bedrooms and 2 smaller maid’s rooms with their own “service hall” area.

There still aren’t any pictures of the kitchen in this unit.

If you recall, it has some of its original features including a wood burning fireplace in the living room and original plaster.

There’s no central air but there’s a washer/dryer in the unit.

There’s no parking.

Originally listed in May 2019 for $575,000, it has been reduced to $299,500.

It went under contract shortly after the reduction under $300,000 but has fallen out of contract and has been re-listed.

The HOAs are now $6836 a month and include the property taxes.

This building is in the center of East Hyde Park and is walkable to Trader Joe’s, Whole Foods, the University of Chicago campus and the Museum of Science and Industry.

At $299,500, is this a deal?

Robert Sullivan at Berkshire Hathaway KoenigRubloff still has the listing. See the pictures here.

Unit #10N: 6 bedrooms, 3.5 baths, 5000 square feet, co-op

  • I couldn’t find a prior sales price as it’s a co-op
  • Originally listed in May 2019 for $575,000
  • Reduced several times
  • Was listed in September 2019 at $399,500
  • Reduced
  • Went under contract in November 2020 listed at $299,500
  • Re-listed in December 2020 at $299,500
  • Assessments are now $6836 a month (they were $6409 a month in September 2019) (includes heat, property taxes, doorman, exterior maintenance, lawn care, scavenger, snow removal)
  • Taxes are included in the HOA
  • No central air
  • Washer/dryer hook-ups in the unit
  • Wood burning fireplace
  • No parking but available in the neighborhood for rent
  • Bedroom #1: 16×20
  • Bedroom #2: 13×20
  • Bedroom #3: 15×15
  • Bedroom #4: 15×15
  • Bedroom #5: 10×16
  • Bedroom #6: 9×12
  • Living room: 19×28
  • Dining room: 18×24
  • Kitchen: 16×16
  • Reception Hall/Foyer: 12×15
  • Orangerie: 19×20

28 Responses to “5,000 Sq Ft Hyde Park Vintage Penthouse Now Just $299,500: 5490 S. South Shore”

  1. If you offered to give me this place, I would say no. Those assessments (understanding that taxes are included even) are ridiculous. And they increased recently, which probably means that the building is having trouble covering costs. That, in my experience, is when assessments go up. Imagine what you could rent for $7K/month.

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  2. Just can’t imagine anyone who could afford $7k/month before the mortgage is going to be interested in this property. Nice views, but unit still needs work.

    This looks like one of those buildings where the value of the unit is going to zero because maintenance is so high.

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  3. What a sad property. Its too bad that it has the less desirable lake view, otherwise this would have sold for the initial ask /s.

    Hopefully the new windows are part of whats driving the HOA costs (Doubtful). This could be an awesome retro home, except the picks are probably the only ones not completely screaming “Run Away”. Looks like theres plaster damage (Water?) in the sunroom. and the mis-matched pink tile in the bathroom ( going to be a bitch finding a match)

    Would guess that this is in some sort of probate hell. Must suck having to cut a check for $7/k mo when not living there. Someones inheritance is going up in smoke

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  4. No, this is not a deal, but a monster financial trap that could bankrupt any upper-middle class family financially clueless enough to buy into it. This place has, in fact, been on and off the market a few times over the past 5 years at least. Not only is the HOA high for even a vintage building, at approximately $1.25 a square foot, this is a cooperative building. Coop boards have a great deal more discretion than condominium boards do, and can lob a massive special assessment at you without seeking the approval of the general ownership, and it will be payable immediately. And if you don’t have the cash on hand and can’t get a loan, well, tough. Just turn in your keys- see 5000 S East End co-op to condo conversion.

    This place was built for super-rich people, who haven’t been attracted to outer neighborhoods like Hyde Park for a long time, which is why it is so seemingly cheap at $300K. Large old co-ops with HOA costs of $1 a square foot or more don’t even sell well or quickly in super-wealthy neighborhoods like Lincoln Park or Streeterville, as we can see with units at buildings like 2430 or 2450 N Lakeview languishing on the market for years. Modern buyers expect, and can get, a much higher level of amenity with far lower maintenance costs in new condo towers, without joining a co-operative association and subjecting themselves to granular scrutiny of their personal finances by a coop board.

    I love buildings like this, but fear for their future, because there are fewer buyers all the time who are both willing and able to support them. Hyde Park in particular seems to be full of beautiful old buildings built for mega-millionaires, that are simply impossible for people of “ordinary” semi-wealthy or upper middle class, to support. All it will take to make them completely unworkable and unlivable, is higher energy costs and maintenance costs.

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  5. “and the mis-matched pink tile in the bathroom ( going to be a bitch finding a match)”

    When we bought our current home a couple of years ago, we had one tan-tiled/tub bath and one pink one like this place. We had “Miracle Method” (a franchise I think) turn the tile/tubs white (it cost about $1,600 to do both). Not that that alone should cause anyone to buy this particular place, but this seller might consider doing the same.

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  6. 10S is also for sale–$499:

    https://www.redfin.com/IL/Chicago/5490-S-Shore-Dr-60615/unit-10S/home/164551037

    listing has a floorplan

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  7. 8S had been updated when it sold for $650 in Feb-17:

    https://www.redfin.com/IL/Chicago/5490-S-Shore-Dr-60615/unit-8S/home/108540841

    Seems like the only realistic buyers of any of these units are UC affiliates–could be a workable thing for a school affiliated entity to buy it out, update it in phases, and run it as a faculty (longterm) residence building.

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  8. The definition of a money pit. Starting a go-fund me or Kickstarter campaign to afford the monthly assessments and a separate one to rehab the unit is what’s needed to buy this.

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  9. “Seems like the only realistic buyers of any of these units are UC affiliates–could be a workable thing for a school affiliated entity to buy it out, update it in phases, and run it as a faculty (longterm) residence building.”

    Wouldn’t you just build new?

    It a shame but this is just going to bleed people dry. If you got it for $50/sf and did improvements for $150/sf sell at $225/sf you’re still > $1MM. Hopefully you could get the HOA in the $3k range.

    You still have the problem of selling 21 properties at over $1MM Just call for the wrecking ball

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  10. “selling 21 properties at over $1MM”

    Not sell them–rent them. Reserve a couple/tree for visiting faculty (probably furnished).

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  11. “Not sell them–rent them. Reserve a couple/tree for visiting faculty (probably furnished).”

    As 5000sf apartments/dorms?

    Ken Griffin Towers?

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  12. “As 5000sf apartments/dorms?”

    Like I said: as a faculty (longterm) residence building.

    A perq tied to being a faculty member.

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  13. “A perq tied to being a faculty member.”

    Thats a heck of a perk. They’re endowment could survive the leaching

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  14. Wouldn’t be free, but I bet adding the building to the University’s building management system would reduce the operating costs quite a lot, such that rent could be comparable to the current HOA ‘rent’, while generating maintenance reserves/renovation cost repayment.

    And not that that is a “good” idea–I just don’t think there is another one that is reality-based and preserves the building as residential apartments.

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  15. The building seems like a deconversion candidate. I don’t know how owning in this building makes any kind of financial sense. I’d be curious how many of the other units are occupied and are they of similar size / monthly nut. The universe of people who can pay that kind of coin is pretty small and even smaller when you consider property location.

    I can see the University renovating and maybe use for graduate dorms or maybe semi-luxury faculty housing if the units are big. It would be a nice perk.

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  16. Not it’s not a deal. It wouldn’t even be a deal at zero with that monthly HOA + taxes nut.

    This property has a value of less than zero given what the HOA and Chicago taxman has done to it.

    And of course if negative property values were actually a thing you’d just take the money given to buy it and run and default on the mortgage.

    This property is a disaster.

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  17. I don’t get the concern with the hoa. Any condo in the city over 4K sq ft is going to be a minimum of 7k per month in assessments and taxes. If The neighborhood came back could do quite well.

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  18. “maybe semi-luxury faculty housing if the units are big”

    Russ–it’s 20 units–they’re all (basically) the same size as this one–a legit ~5000 sf, 2 per floor.

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  19. Laura’s comment is spot on. And like her, I fear for the future of these type of buildings. Not just in Hyde Park, but even on the North Side.

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  20. Don’t know their tax split, but it is likely way too high. I know of a similar building that successfully appealed values to average last 3 sales which were the only sales in the past few year. Cut the bill by more than a third.

    The university owns tons of building in the greater Hyde park area. Converting this to faculty housing sounds like an interesting idea. They already offer faulty one of the best schools in the county for their kids. Tuition would normally ring in at 35k per child. My understanding is they don’t pay great relative to peers, but have unmatchable perks like this.

    If the university did buy this, I wonder if they pay taxes at all? Might make this attractive if the expense was a small acquisition + maintenance and they are able to maintain regality, history and charm of the neighborhood. A few years ago I spoke the the guy who heads the university’s real estate acquisitions and mgt and its amazing how much they own and how much of the recent development they are behind. They work hard to curate what goes into their building to try to best serve the long term success of the neighborhood i.e. whole foods.

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  21. … @ AC “If the university did buy this, I wonder if they pay taxes at all?”

    “Hey, cut our taxes or we are selling the whole place to UC!”

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  22. A perq tied to being a faculty member.

    I have not seen perq spelled correctly in AGES. I bet you spell it “psych” instead of “sike”, too.

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  23. Sean, the HOA is indeed very high relative to other vintage buildings of comparable or higher quality.

    For example, an incomparably elegant 4000 sq ft unit that Sabrina featured on this site a few years back, at the beautiful 3400 N Lake Shore Drive condominium, had HOA fees of $2,700 a month, and it was a far better apartment in a much better location than this. Even the taxes on it didn’t bring it to the same level as this. 3400 N Lake Shore, 3300 N Lake Shore, 3530-34 N Lake Shore, and 3800 N Lake Shore, all charge HOA fees that range from $0.60 a sq ft to $0.75 a square foot. You will note that the larger units break down cheaper per square foot than the smaller ones, as there is a “baseline” charge, then a charge per square foot. Even 3750 N Lake Shore,with its indoor pool, TWO manned front desks, and numerous elevator tiers, doesn’t charge any more than this Hyde Park building.

    Just too much money for too little in the way of building amenity.

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  24. “I bet you spell it “psych” instead of “sike”, too.”

    Given that I have a PhD in sikeology, only in certain usages. [WTAF?? sike is used in something other than textspeak or comics??]

    “Even the taxes on it didn’t bring it to the same level as this.”

    Appear that the assessment includes ~$1500/month in taxes, so the comparable is about $1 psf, which is high, but not crazy high, given there are only 20 units, and there is a parking lot.

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  25. Taxes are included in the assessment. Assessments also include approximately $1500 mortgaged portion corresponding to the criminal Life Safety Evaluation Ordinance/shakedown, which required massive expenditure in this building. The expenses on that mortgage are tax–deductible, and will expire in 5 years.

    The building is 24hr full-service for 20 units, impeccably maintained, never had a special assessment (other than the Life Safety shakedown), has ample reserves, and is extremely well run.
    Taking the taxes and expiring mortgage into account, the ~4K HOA is in line with what it takes for 20 units to support full–time staff.

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  26. The user above is correct that HOAs on this unit include taxes and an expiring mortgage associated with city-mandated life safety updates. After that, the assessments primarily cover full-time, full-service staff. The units live like luxurious single family homes, the staff are top-notch, and the enormous yard is a beautifully kept haven for adults and children alike.

    The comments insinuating the building is somehow “distressed” or in need of University rescue are perplexing and without foundation. The building is in excellent financial shape. Also, note that four of these units were sold and updated in the last three years alone. Whoever buys the penthouse will make a stunning home of it!

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  27. Even, no special assessments is really impressive. Most coops like this collect assessments to pay the bills and special assess for anything beyond the ordinary. Follows the logic of letting financially capable and vetted people invest and manage their own money rather than the building holding it for them in CDs.

    Very cool building. There’s an ass for every seat, and you don’t need many to fill a 20 units, especially when residents tend to stay for a very long time.

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  28. How did I miss this one?

    A couple comments: the University sold off the bulk of their residential properties several years ago and isn’t buying any more.

    Theaster Gates lives here along with a lot of very long term residents.

    The windows were replaced about ten years ago with top of the line windows (there were articles about it in trade papers).

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