Search Chicago Penthouses on the MLS Below:, $400,000 - $500,000

All Listings Under $100,000 $100,000 - $200,000
$200,000 - $300,000 $300,000 - $400,000 $400,000 - $500,000
$500,000 - $600,000 $600,000 - $700,000 $700,000 - $800,000
$800,000 - $900,000 $900,000 - $1,000,000 Over $1,000,000
49 Properties Found. Page 1 of 5

Welcome Home To This Spectactular Duplex Pentho...

NEW Photo of Listing #10372006
prevnext 1 of 17 images

$500,000 Contingent

  • 3 Beds
  • 2 Baths
  • 1,800 ft²

Residential

1818 West Belmont Avenue #4, Chicago, IL

MLS® #10372006

Welcome Home To This Spectactular Duplex Penthouse With Unobstructed City Views From Huge Private Roofdeck In Highly Coveted Roscoe Village. This 1800 Sq Ft 3 Bedroom/2 Bath Features Wide Open Floorplan With 10 Foot Ceilings, Fireplace, Hardwood Floors Throughout, Private Master Bedroom Suite On ...

Spectacular Townhome With A Contemporary Open C...

NEW Photo of Listing #10371983
prevnext 1 of 8 images

$499,900 Active

  • 3 Beds
  • Baths

Residential

6135 North Ravenswood Avenue #2, Chicago, IL

MLS® #10371983

Spectacular Townhome With A Contemporary Open Concept Layout. Enter The Bright South Facing Space - Large Living Room Offers A Gracious Seating Area. Sleek White Cabinetry With Quartz Countertop Including A Large Island With Waterfall Edge. High End Stainless Steel Appliances And Fixtures. Pr...

Streeterville Penthouse W/ Amazing City Scape A...

REDUCED 3% Photo of Listing #10327284
prevnext 1 of 21 images

$499,900 Active

  • 1 Beds
  • Baths
  • 1,025 ft²

Residential

240 East Illinois Street #3102, Chicago, IL

MLS® #10327284

Streeterville Penthouse W/ Amazing City Scape And Lake Views At 240 Illinois, City Front Plaza. Full Amenity Building Right Off Michigan Ave - Not On The Lower Level With Easy Access To Everything. Brand New Whole Foods On The Lower Level! This 1000+ Sqft All Glass Corner One Bedroom Has Views Th...

Take A 3d Tour, Click On The 3d Button & Wa...

prevnext 1 of 21 images

$499,888 Contingent

  • 3 Beds
  • 2 Baths

Residential

2129 West Belmont Avenue #4e, Chicago, IL

MLS® #10330746

Take A 3d Tour, Click On The 3d Button & Walk Around. Watch A Custom Drone Video Tour, Click On Video Button! Live In The Heart Of Roscoe Village In This Boutique Elevator Building. This Extra Wide 3bed/2bath Condo Will Check All Your Boxes. Modern Kitchen W/stainless Steel Appliances, Granit...

This Rare Corner Loft In Intimate Bldng Located...

NEW Photo of Listing #10377582
prevnext 1 of 14 images

$499,500 Active

  • 2 Beds
  • 2 Baths

Residential

300 West Grand Avenue #503, Chicago, IL

MLS® #10377582

This Rare Corner Loft In Intimate Bldng Located In The Heart Of River North. It Offers Mass 12' Ceilings And Is Flooded W/ Naturl Lght. With Beautiful Views To The S & E, This 2bd/2bth Home Prvdes True Urban Living. There Are Upgrds Galore. The Mstr Bth Has Been Newly Rmlded W/ Delta &am...

West Town Penthouse. 1500 Asf Of Extra-wide, Su...

prevnext 1 of 20 images

$499,500 Active

  • 2 Beds
  • 2 Baths
  • 1,460 ft²

Residential

1516 West Grand Avenue #4w, Chicago, IL

MLS® #10354811

West Town Penthouse. 1500 Asf Of Extra-wide, Sunny & Spacious Urban Living. Great Square Foot/$$ Value! Close To Cafes, Cta, Etc. Super-quiet Top Floor Condo Features High Ceilings, Great Closet Space & Two Separate Cubby Areas For Wine Storage And/or Desk Space (see Pix). Wood-burning Fi...

Fabulous Top Floor Wicker Park Condo With Priva...

prevnext 1 of 22 images

$499,000 Contingent

  • 2 Beds
  • 2 Baths

Residential

1515 North Claremont Avenue #3, Chicago, IL

MLS® #10373263

Fabulous Top Floor Wicker Park Condo With Private Rooftop Deck And Amazing Skyline Views! The High Ceilings, Hardwood Floors Throughout, And Abundant Sunlight Make This Condo Feel Like Home. The Spacious Open Floor Plan, And The Private Rooftop Make For Great Entertaining! You'll Also Love...

Absolutely Stunning Duplex-up In Ukrainian Vill...

NEW Photo of Listing #10361500
prevnext 1 of 26 images

$499,000 Contingent

  • 3 Beds
  • 3 Baths
  • 2,000 ft²

Residential

2527 West Chicago Avenue #2, Chicago, IL

MLS® #10361500

Absolutely Stunning Duplex-up In Ukrainian Village! This Unit Has Been Impeccably Cared For, With A Handsome Dark Brick Exterior And Fully Updated And Light-filled Interior Located Near Transit, Tons Of Hot-spot Restaurants, Bars, And More. Spacious And Flowing Floor Plan With Tall Ceilings, Oak ...

Amazing 2br/2ba Extra-wide Penthouse In Unbeata...

prevnext 1 of 22 images

$499,000 Contingent

  • 2 Beds
  • 2 Baths
  • 1,300 ft²

Residential

1125 West Belmont Avenue #4, Chicago, IL

MLS® #10347387

Amazing 2br/2ba Extra-wide Penthouse In Unbeatable Lakeview Location! Sunny Top Flr Corner Unit, 13' Tall Ceilings, Lots Of Wndws & Unobstructed View Of Skyline From Bdrms, Terrace & 800 Sf Pvt Rooftop Deck! Top Of Line Finishes - Cherrywood, Granite, Ss, Walk-in Clsts, Jetted Tub ...

Fabulous Top-floor Penthouse Condo On A Quiet O...

NEW Photo of Listing #10372257
prevnext 1 of 11 images

$495,000 Active

  • 2 Beds
  • 2 Baths
  • 1,400 ft²

Residential

1615 North Claremont Avenue #3s, Chicago, IL

MLS® #10372257

Fabulous Top-floor Penthouse Condo On A Quiet One-way Bucktown Street. This Extra-wide Two-bedroom Two-bath Home Boasts Open Floor Plan With 17-foot Vaulted Ceilings And West-facing Windows Letting In Tons Of Natural Light. Gas Fireplace Located In The Living Room Large Kitchen Includes Custom Wh...

Calling All Roof Deck Lovers. Amazing, Top Flo...

NEW Photo of Listing #10371488
prevnext 1 of 16 images

$495,000 Active

  • 2 Beds
  • 2 Baths

Residential

1247 North Bosworth Avenue #3s, Chicago, IL

MLS® #10371488

Calling All Roof Deck Lovers. Amazing, Top Floor Penthouse 2 Bed/2 Bath Located In The Heart Of Wicker Park. Steps From Division Blue Line Stop & Hottest Area Of Bars, Restaurants And Shopping. High-end Finishes Include: Hardwood Floors, Custom Cabinets/shelving, $20k Master Bath Renovation...

Fantastic Top Floor 2br/2ba Condo In Lakeview! ...

NEW Photo of Listing #10351923
prevnext 1 of 15 images

$489,900 Contingent

  • 2 Beds
  • 2 Baths

Residential

3211 North Racine Avenue #3, Chicago, IL

MLS® #10351923

Fantastic Top Floor 2br/2ba Condo In Lakeview! This Beautiful Home Features A Huge Private Rooftop Deck With Awesome Skyline Views In Addition To The Large Back Deck. The Main Living Space With Huge Windows Is Wide Enough For A Dining Table Boasts 2-story Vaulted Ceilings, Bright South & West...

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 May 26th, 2019 at 4:06pm CDT.