Search Chicago Penthouses For Sale, $400,000 - $500,000

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32 Properties Found. Page 1 of 2

Penthouse 2 Bedroom, 2 Bath With Coveted Privat...

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$499,900 Active

  • 2 Beds
  • 2 Baths
  • 1,350 ft²

Residential

3503 North Sheffield Avenue #3n, Chicago, IL

MLS® #10632349

Penthouse 2 Bedroom, 2 Bath With Coveted Private Rooftop Deck, Garage & Extra Parking Space. Open Layout Connecting Kitchen, Living Room And A Lovely Terrace Overlooking Sheffield. Master Bedroom W/ Juliette Balcony, Separate Shower & Whirlpool Tub. Fantastic Views From Your Own Rooftop Deck Fo...

Top-floor Duplex With Huge Roof-top Deck! If Yo...

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$499,000 Contingent

  • 3 Beds
  • 3 Baths
  • 1,750 ft²

Residential

1504 North Bosworth Avenue #3n, Chicago, IL

MLS® #10656199

Top-floor Duplex With Huge Roof-top Deck! If You Are Looking For A Light And Bright, Move-in Ready Condo In A Fantastic Location, Look No Further! This Unit Just Got A Huge Facelift With New Hardwood Flooring Throughout, 2 Brand New Bathrooms, New Mechanicals And Washer/dryer, And A "modern Farmh...

Enjoy Luxury Living In This 2 Bedroom, 2 Bathro...

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$499,000 Contingent

  • 2 Beds
  • 2 Baths
  • 1,800 ft²

Residential

1645 West School Street #419, Chicago, IL

MLS® #10640801

Enjoy Luxury Living In This 2 Bedroom, 2 Bathroom + Den, Lakeview Penthouse In Burley School District! This Fabulous, Duplexed, Loft-style Home Is Spacious, Unique, And A Cut Above Most Other Properties That You Will Encounter In Your Search. Featuring Gleaming Hardwood Floors, A Gas Fireplace, ...

Be Ready For Spring In This Roscoe Village Pent...

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$499,000 Contingent

  • 3 Beds
  • 2 Baths

Residential

2332 West Belmont Avenue #4, Chicago, IL

MLS® #10639449

Be Ready For Spring In This Roscoe Village Penthouse With This Expansive Private Rooftop Deck! Featuring A Pergola With Built-in Seating, City Views And A Raised Bed Vegetable Garden With Irrigation System, This Will Be An Extension Of Your Home All Summer Long. The Interior Of The Home Feature...

2 Bedroom Residential Property in Chicago, IL

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$499,000 Contingent

  • 2 Beds
  • 2 Baths

Residential

2717 North Southport Avenue #3n, Chicago, IL

MLS® #10635323

Welcome To Your Upgraded Roscoe Village Penthou...

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$495,000 Active

  • 3 Beds
  • 2 Baths
  • 1,590 ft²

Residential

2222 West Belmont Avenue #501, Chicago, IL

MLS® #10585089

Welcome To Your Upgraded Roscoe Village Penthouse Corner Unit In An Elevator Building With Partial Skyline Views, Direct Sunlight, Heated Garage Parking, 2 Private Outdoor Spaces (476 Sq. Ft. Total!), And Viking/sub-zero Appliances! This Unit Features An Open Layout With One Sunny Bedroom Opening...

Click Virtual Tour For Walk-thru Video - Show I...

REDUCED 2% Photo of Listing #10661448
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$489,900 Active

  • 2 Beds
  • 2 Baths
  • 1,535 ft²

Residential

1521 West Haddon Avenue #4c, Chicago, IL

MLS® #10661448

Click Virtual Tour For Walk-thru Video - Show In Person With Social Distancing Or Request A Scheduled Video Walk Thru Call With Our Showing Agent For You And Your Agent. This Penthouse Loft With Soaring Ceilings & Exposed Brick Is Filled With Natural Light & Sits In An Elevator Building. The Open...

Dramatic Penthouse With Cathedral Ceilings, Sky...

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$485,000 Contingent

  • 2 Beds
  • 2 Baths

Residential

849 North Hermitage Avenue #3, Chicago, IL

MLS® #10657270

Dramatic Penthouse With Cathedral Ceilings, Skylights, Tons Of Natural Light, 3 Private Outdoor Spaces Including Private Roofdeck W/interior Staircase Plus Two Car Tandem Parking, Make This Place The Perfect Home! Coveted Open Floorplan Featuring Living Room With Soaring Ceilings, Woodburning Fir...

Welcome To Penthouse Unit 3605. Top Floor In Th...

NEW Photo of Listing #10684549
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$475,000 New

  • 2 Beds
  • 2 Baths
  • 1,310 ft²

Residential

545 North Dearborn Street #3605, Chicago, IL

MLS® #10684549

Welcome To Penthouse Unit 3605. Top Floor In The Building Featuring 10 Foot Ceilings. There Are Fewer Units On This Floor Due To The Penthouse Level. This Custom Designed Condo Has Gorgeous South Facing City Skyline Views In The Desirable River North Neighborhood. Walkout To Your Spacious Balcony...

Penthouse Living On The 606. South Logan Square...

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$475,000 Contingent

  • 2 Beds
  • 2 Baths

Residential

1732 North California Avenue #3, Chicago, IL

MLS® #10672057

Penthouse Living On The 606. South Logan Square All Brick Newer Construction 2/2 With 3 Sunlit Exposures And 3 Dedicated Outdoor Spaces. All Hardwood Floors, High Ceilings, Floor To Ceiling Windows And Stone Fireplace. Custom Cabinetry, Quartz Counters With Long Pennisula And All Stainless Steel ...

Location! Snag This Incredible Two Bedroom/ Two...

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$475,000 Contingent

  • 2 Beds
  • 2 Baths

Residential

630 West Briar Place #4, Chicago, IL

MLS® #10653826

Location! Snag This Incredible Two Bedroom/ Two Bathroom Penthouse Condo With Soaring Ceilings And Skylights On Beloved Briar Place A Half Block From Everything East Lakeview Has To Offer! This Top Floor Penthouse Condo Offers A Gracious Floor Plan That Is Bright And Functional! Well-appointed Li...

Awesome Super Sunny 2 Level Condo In The Heart ...

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$475,000 Contingent

  • 2 Beds
  • Baths
  • 1,445 ft²

Residential

5115 North Clark Street #3b, Chicago, IL

MLS® #10647104

Awesome Super Sunny 2 Level Condo In The Heart Of Andersonville. Elevator Building Duplex Up Penthouse Loft! Floor To Ceiling Windows, Balcony Off Living Room, Gas Fireplace, Huge Kitchen W/ Island, Granite & Ss. Dining Space, Hardwood Floors, Powder Room On Main Level. 2 Beds Upstairs W/carpet T...

Stunning Roscoe Village / North Center 2 Bedroo...

REDUCED 3% Photo of Listing #10577282
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$475,000 Active

  • 2 Beds
  • 2 Baths
  • 1,300 ft²

Residential

3644 North Damen Avenue #3, Chicago, IL

MLS® #10577282

Stunning Roscoe Village / North Center 2 Bedroom / 2 Bath Sun Drenched Penthouse With 800 Square Foot Private Rooftop Deck! Fantastic Open & Expansive Living/ Dining Floor Plan Featuring Soaring Cathedral Ceilings With Skylights, 3 Sides Of Light Exposure, Fireplace With Gas Starter, And Terrace...

Beautiful 3 Bedroom, 2 Bathroom Penthouse In Th...

NEW Photo of Listing #10686621
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$474,900 New

  • 3 Beds
  • 2 Baths
  • 1,760 ft²

Residential

2244 West Belmont Avenue #4w, Chicago, IL

MLS® #10686621

Beautiful 3 Bedroom, 2 Bathroom Penthouse In The Heart Of Roscoe Village. Unique Wide 1760 Square Foot Unit With Updated Kitchen Featuring: Granite Counters, Stainless Steel Appliances, Full-height Cabinets, And Custom Woodwork. Light Filled Living Room Boasts Brazilian Cherry Hardwood Floors, Cr...

***motivated Seller*** Top Floor Corner Double ...

REDUCED 5% Photo of Listing #10629229
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$474,900 Active

  • 2 Beds
  • Baths
  • 1,750 ft²

Residential

33 East Cedar Street #19ab, Chicago, IL

MLS® #10629229

***motivated Seller*** Top Floor Corner Double Unit Penthouse With 2 Master Bedrooms Both With Their Own En-suites!! Remodeled In 2015-16 Entire Living Room / Dining Room / Kitchen / Office Area / Laundry Room With Main Areas Having Hardwood Floors, Crown Molding Throughout, Electronic Remote-co...

Enjoy Your Summer On Your Large Private Rooftop...

NEW Photo of Listing #10685065
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$470,000 Contingent

  • 2 Beds
  • 2 Baths
  • 1,400 ft²

Residential

2144 West Schiller Street #h, Chicago, IL

MLS® #10685065

Enjoy Your Summer On Your Large Private Rooftop Deck With Hot Tub, Gazing At The Chicago Skyline. This Spectacular Penthouse Is On A Tree Lined Street In The Heart Of Wicker Park With Gated Entry. Inside This 2 Bed/2 Bath You'll Love The Open Floor Plan With Hardwood Floors Throughout, Gas Fir...

Lincoln Park Lofty 2 Bed / 2.5 Bath Duplex With...

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$469,900 Active

  • 2 Beds
  • Baths

Residential

2756 North Wolcott Avenue #3s, Chicago, IL

MLS® #10677880

Lincoln Park Lofty 2 Bed / 2.5 Bath Duplex With A 500sf Rooftop Deck + Large Balcony Off The 2-story Living Room And 2nd-floor Family Room Including 2 Out-door Parking Spaces! The Main Level Is Sunny & Airy, Open Kitchen, S/s Appliances, Granite Countertops & Island With Seating For 2, A Combo ...

East Wicker Park Penthouse With Stunning Vaulte...

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$469,000 Contingent

  • 2 Beds
  • 2 Baths
  • 1,350 ft²

Residential

1519 North Bosworth Avenue #3, Chicago, IL

MLS® #10654957

East Wicker Park Penthouse With Stunning Vaulted Cathedral Ceilings And Three Private Outdoor Spaces, Including Private Roof Deck With Interior Staircase! This Beautiful 2 Bed, 2 Bath Top Floor Unit Has Easy Access To The Blue Line, 90/94 And Is Walking Distance To Parks, Restaurants And Shopping...

Sun-filled Penthouse In The Heart Of Lakeview W...

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$469,000 Active

  • 2 Beds
  • 2 Baths
  • 1,200 ft²

Residential

3247 North Racine Avenue #3, Chicago, IL

MLS® #10625533

Sun-filled Penthouse In The Heart Of Lakeview With Vaulted Ceilings, Wood Burning Fireplace And Hardwood Floors Throughout. The Wide Living Room Layout Easily Accommodates A Dining Room Set And Opens To The Kitchen With Stainless Steel Appliances, Custom Backsplash And Granite Counter Tops. Large...

Incredible Sun-filled Clark/belmont Area Pentho...

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$469,000 Active

  • 2 Beds
  • 2 Baths
  • 1,500 ft²

Residential

3217 North Wilton Avenue #4, Chicago, IL

MLS® #10614251

Incredible Sun-filled Clark/belmont Area Penthouse With Rooftop Deck And A Private Balcony Off Master Suite. Private Entry Staircase Welcomes You Home. Inside You'll Discover A Spacious, Extra-wide, Open Floorpan With Cherry Floors Throughout. An Expansive Living Room With Fireplace And Juliet...

Top Floor Sun Filled 2 Bed/2 Bath Condo In Desi...

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$465,000 Contingent

  • 2 Beds
  • 2 Baths
  • 1,250 ft²

Residential

3041 North Racine Avenue #3, Chicago, IL

MLS® #10646800

Top Floor Sun Filled 2 Bed/2 Bath Condo In Desirable Lakeview Location. Vaulted Ceilings And Skylights Add To The Allure Of The Large Living/dining Space With Gas Fireplace That Opens Up To The Beautifully Updated Kitchen. Kitchen Features White Cabinets, Granite Countertops, White Subway Tile Ba...

This Listing Has Floor Plan Pdf, Interactive Fl...

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$465,000 Active

  • 2 Beds
  • 2 Baths
  • 1,600 ft²

Residential

3519 North Sheffield Avenue #3s, Chicago, IL

MLS® #10614742

This Listing Has Floor Plan Pdf, Interactive Floor Plans As A Tour To Help With Remote Showings. All Floor Plans Are Also Pictures At The End Of The Unit Pictures. Bright And Sunny Wrigleyville 2 Bed / 2 Bath Penthouse Just Steps Away From Everything Lakeview Has To Offer. 12 Ft Ceilings And 3 L...

Take In The Vista From Your Private Wrap-around...

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$460,000 Active

  • 2 Beds
  • 2 Baths
  • 1,650 ft²

Residential

2614 North Clybourn Avenue #401, Chicago, IL

MLS® #10672557

Take In The Vista From Your Private Wrap-around Balcony Or From Your Master Bedroom. This Lofted 2 Bedroom 2 Bath Corner Unit Penthouse With Stunning 25ft Floor To Ceiling Walls Of Windows Opens Up To Chicago Skyline Views You Won't Forget. Unlike Most Lofts, This Unit Offers Two, Truly Separate ...

Amazing & Rarely Available Lincoln Square 1,700...

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$455,000 Active

  • 2 Beds
  • 2 Baths
  • 1,740 ft²

Residential

5588 North Lincoln Avenue #505, Chicago, IL

MLS® #10670745

Amazing & Rarely Available Lincoln Square 1,700 Sf Penthouse W/lrg Terr+2 Balc. 2 Bd/2 Ba W/din Rm, Huge Master Suite, Hdwd Flrs, Cherry Cab, Blk Zodiaq Cntr, S/s Appls, Steam Shower, Gas Frpl W/logs, In-unit Laundry Rm. In-floor Radiant Heat, Heat-gas-hot Water Incl In Low Assmt, 2008 Solid & Qu...

The data relating to real estate for sale on this website comes in part from the Broker Reciprocity program of Midwest Real Estate Data LLC. Real Estate listings held by brokerage firms other than Berkshire Hathaway HomeServices KoenigRubloff Realty Group are marked with the Broker Reciprocity logo or the Broker Reciprocity thumbnail logo (a little black house) and detailed information about them includes the names of the listing brokers. Some properties which appear for sale on this website may subsequently have sold and may no longer be available. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed.

Listing information last updated on April 10th, 2020 at 12:05am CDT.