Northwest Side Homes with Penthouse Style

Our website features the best real estate search for homes, condos, land and foreclosure properties available in Northwest_Side and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes.

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire.

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood!

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Newest Northwest Side Homes with Penthouse Style

$849,900

3 Beds ⋅ 2 Baths ⋅ 12711917 MLS ⋅ NEW Status

Better than new and hard to recreate at this price! This stunning penthouse residence at The Iowan combines the quality of luxury 2022 new construction with tens of thousands of dollars in thoughtful upgrades already completed for you. No need to wait months for new construction! Located in West Town, this sophisticated 3-bedroom, 2-bath penthouse offers the rare combination of an elevator building, two side-by-side garage parking spaces, and an expansive private rooftop deck with sweeping treetop and skyline views. Floor-to-ceiling windows flood the home with natural light, while the open-concept floor plan is perfect for both everyday living and entertaining. The chef's kitchen is beautifully appointed with Wolf and Sub-Zero appliances, an oversized island, custom pantry cabinet, and a designer backsplash that extends seamlessly from the countertops. Throughout the home, the owners elevated nearly every space with custom California Closets featuring Elfa systems, upgraded paint finishes, designer lighting, additional recessed lighting, motorized window shades in the living room and primary suite, custom window treatments throughout, an Ecobee smart thermostat, and a convenient keyless entry system. The luxurious primary suite feels like a private retreat with dual custom closets, additional linen and storage cabinetry, heated floors, a soaker tub and a spa-inspired steam shower. Even the secondary bedrooms have been enhanced with updated lighting and custom closet systems, a built-in safe in the guest room and charming wall molding to add designer character to the nursery. Outdoor living is just as impressive. The massive private rooftop deck is already equipped with a gas line for a fire pit, and both the rooftop deck and balcony have been professionally sealed for long-term durability. Two attached garage parking spaces are included and are accessed through their own garage door - making city parking a breeze. The association offers a dedicated bike rack in the garage for added convenience. The building itself has continued to improve since completion, the HOA recently updated the foyer with new flooring and fresh paint, while residents also enjoy annual exterior window washing. Perfectly situated in one of Chicago's most vibrant neighborhoods, you'll enjoy easy access to neighborhood favorites along Chicago Avenue, Division Street, and Milwaukee Avenue, including award-winning restaurants, coffee shops, breweries, boutiques, parks, and convenient public transportation. This is a rare opportunity to own a truly turnkey luxury penthouse where every detail has already been thoughtfully upgraded and offering a level of finish and functionality that's rarely found, even in brand-new construction.

2405 W Iowa Street Unit #402, Chicago

$225,000

1 Beds ⋅ 1 Baths ⋅ 12717657 MLS ⋅ NEW Status

Charming and spacious top floor condo in the heart of Chicago's desirable Old Irving Park neighborhood! Separate living room and dining room with hardwood floors throughout and canned lighting. Chefs' dream kitchen with plenty of counter, cabinet space and stainless-steel appliances. Full size master bedroom with courtyard views and a full bathroom just steps away. Attached balcony overlooking the courtyard. One assigned parking space is included. Coin laundry, storage and party room with a bar are located in the basement. Pet friendly building. Fantastic location with the Blue Line, Edens Expressway, shops, restaurants and night life. Move in ready! Available now!

4200 N Keystone Avenue Unit #3B, Chicago

$770,000

3 Beds ⋅ 2 Baths ⋅ 12716745 MLS ⋅ NEW Status

Easy city living. Modern boutique elevator building. Walkable location. Bright, California-inspired design. This newer construction 3-bedroom, 2-bath home offers effortless city living with a lighter, airy aesthetic. Flooded with natural light, the home features an open-concept floor plan and elevated finishes throughout. The kitchen serves as the showcase of the home, with sleek Scavolini cabinets, striking waterfall countertops, and an easy flow into the expansive living and dining areas, making it ideal for both entertaining and everyday living. A balcony extends directly off the main living space, creating an easy indoor-outdoor connection. Perfect for grilling. The thoughtfully designed split floor plan offers privacy and functionality, with the primary suite tucked away on one side of the home and two additional bedrooms positioned on the opposite wing. The serene primary suite feels like a true retreat, featuring heated floors with refined finishes. Additional highlights include a private section of the rooftop deck with skyline views, concrete soundproofing between floors, one heated garage parking space equipped with an EV charger, and an unbeatable location. Surrounded by some of the neighborhood's best restaurants, boutiques, cafes, and convenient public transportation, this home is truly turnkey.

1523 N Western Avenue Unit #3A, Chicago

$950,000

4 Beds ⋅ 3 Baths ⋅ 12716618 MLS ⋅ NEW Status

*Construction Now Complete* Experience the pinnacle of modern luxury at THE ASH BUCKTOWN, one of the neighborhood's most exciting new developments. ***Unit 303 comes with 2 electric car ready carport parking spaces!*** Built with a focus on privacy and performance, the entire building is engineered for superior soundproofing with a sealed shell structure, concrete walls separating units around the perimeter, blown-in cellulose insulation between floors coupled with closed-cell spray foam, Maxxon acoustic soundproofing rubber mattes, 1-inch of Maxxon Gypcrete concrete flooring, and the absence of traditional can lights-ensuring peace and privacy. Crafted with impeccable attention to detail, this 4 -bedroom, 2.5-bath condo features an expansive open floor plan with soaring nearly 10-foot ceilings, solid-core 8-foot doors, and floor-to-ceiling European windows that fill the space with natural light while offering superior sound insulation. The chef's kitchen is a showcase of European design, with sleek cabinetry, oversized quartz countertops with waterfall edges, and a premium stainless steel appliance package-perfect for both everyday living and entertaining. The living room is flooded with an abundance of natural light and flows seamlessly onto a covered private balcony, preset with gas and electricity, that's ready for year-round enjoyment. Designer bathrooms are spa-inspired, featuring heated floors, large-format tile, double-sink vanities, Japanese Style Smart Toilets, and oversized rain showers with handheld wands. Every detail has been optimized for comfort and quality. Custom trim details and curated lighting complete the modern, sophisticated aesthetic. Located in one of Chicago's most vibrant neighborhoods, this home offers premier access to Bucktown/Wicker Park dining, boutique shopping, parks, and the Damen/Milwaukee Blue Line just minutes away. This is a rare opportunity to own a truly exceptional residence in one of the city's most desirable locations.

2072 N Western Avenue Unit #303, Chicago

$1,300,000

4 Beds ⋅ 3 Baths ⋅ 12716549 MLS ⋅ NEW Status

Experience the pinnacle of modern luxury at THE ASH BUCKTOWN, one of the neighborhood's most exciting new developments. This meticulously designed 4-bedroom, 2.5-bath penthouse offers stunning, unobstructed Chicago skyline views directly from the main living space. 1 Indoor Heated Electric Car Ready parking space and 1 tandem storage space included. Built with a focus on privacy and performance, the entire building is engineered for superior soundproofing with a sealed shell structure, concrete walls separating units around the perimeter, blown-in cellulose insulation between floors coupled with closed-cell spray foam, Maxxon acoustic soundproofing rubber mattes, 1-inch of Maxxon Gypcrete concrete flooring, and the absence of traditional can lights-ensuring peace and privacy. Crafted with impeccable attention to detail, this Penthouse features an expansive open floor plan with soaring 10-foot ceilings, solid-core 8-foot doors, and floor-to-ceiling European windows that fill the space with natural light while offering superior sound insulation. The chef's kitchen is a showcase of European design, with sleek cabinetry, oversized quartz countertops with waterfall edges, and a premium stainless steel appliance package-perfect for both everyday living and entertaining. The living room is flooded with an abundance of natural light and flows seamlessly onto a covered private balcony that's ready for year-round enjoyment. Designer bathrooms are spa-inspired, featuring heated floors, large-format tile, double-sink vanities, Japanese Style Smart Toilets, and oversized rain showers with handheld wands. Every detail has been optimized for comfort and quality. Custom trim details and curated lighting complete the modern, sophisticated aesthetic. Penthouse unit features private staircase access to an approx. 1,500 sq/ft rooftop deck with breathtaking Chicago skyline views. Located in one of Chicago's most vibrant neighborhoods, this home offers premier access to Bucktown/Wicker Park dining, boutique shopping, parks, and the Damen/Milwaukee Blue Line just minutes away. This is a rare opportunity to own a truly exceptional residence in one of the city's most desirable locations.

2072 N Western Avenue Unit #PH-403, Chicago

$1,300,000

3 Beds ⋅ 3 Baths ⋅ 12716479 MLS ⋅ NEW Status

*Construction Now Complete* Come experience the pinnacle of modern luxury at THE ASH BUCKTOWN, one of the neighborhood's most exciting new developments. ***2 Indoor Heated Electric Car Ready Parking Spaces Included***This meticulously designed 3-bedroom + Office, 2.5-bath penthouse offers stunning, unobstructed Chicago skyline views directly from the main living space. Built with a focus on privacy and performance, the entire building is engineered for superior soundproofing with a sealed shell structure, concrete walls separating units around the perimeter, blown-in cellulose insulation between floors coupled with closed-cell spray foam, Maxxon acoustic soundproofing rubber mattes, 1-inch of Maxxon Gypcrete concrete flooring, and the absence of traditional can lights-ensuring peace and privacy. Crafted with impeccable attention to detail, this Penthouse features an expansive open floor plan with soaring 10-foot ceilings, solid-core 8-foot doors, and floor-to-ceiling European windows that fill the space with natural light while offering superior sound insulation. The chef's kitchen is a showcase of European design, with sleek cabinetry, oversized quartz countertops with waterfall edges, and a premium stainless steel appliance package-perfect for both everyday living and entertaining. The living room is flooded with an abundance of natural light and flows seamlessly onto a covered private balcony that's ready for year-round enjoyment. Designer bathrooms are spa-inspired, featuring heated floors, large-format tile, double-sink vanities, Japanese Style Smart Toilets, and oversized rain showers with handheld wands. Every detail has been optimized for comfort and quality. Custom trim details and curated lighting complete the modern, sophisticated aesthetic. Penthouse unit features private staircase access to an approx. 1,500 sq/ft rooftop deck with breathtaking Chicago skyline views. Located in one of Chicago's most vibrant neighborhoods, this home offers premier access to Bucktown/Wicker Park dining, boutique shopping, parks, and the Damen/Milwaukee Blue Line just minutes away. This is a rare opportunity to own a truly exceptional residence in one of the city's most desirable locations.

2072 N Western Avenue Unit #PH-401, Chicago

$699,500

2 Beds ⋅ 2 Baths ⋅ 12716229 MLS ⋅ NEW Status

2446 W Augusta Boulevard Unit #PH, Chicago

$774,900

2 Beds ⋅ 2 Baths ⋅ 12711331 MLS ⋅ NEW Status

Stunning newer-construction penthouse in the heart of red-hot East Ukrainian Village! Thoughtfully designed with exceptional craftsmanship, premium finishes, and extensive custom upgrades throughout. The sun-drenched great room features soaring floor-to-ceiling windows, a wood-burning fireplace, and oversized sliding glass doors that open to a spacious private terrace, creating the perfect indoor-outdoor living experience. The chef's kitchen is beautifully appointed with Thermador Professional Series appliances, custom double-stacked cabinetry with glass display uppers, designer lighting, and elegant quartz countertops. Retreat to the spa-inspired primary suite featuring heated floors, a luxurious steam shower with multiple shower heads, and sophisticated porcelain tile accented by striking mosaic and hexagonal details. The beautifully finished guest bath continues the home's high-end aesthetic. A rooftop penthouse room provides the ideal space for a home office, fitness area, or staging lounge for unforgettable rooftop entertaining. The expansive private roof deck showcases breathtaking panoramic skyline and city views, while the covered outdoor living room with a fireplace creates the perfect setting for cozy evenings or entertaining year-round. With three private outdoor living spaces, this home truly embraces Chicago indoor-outdoor living. Additional highlights include hardwood floors throughout, garage parking, in-unit laundry, and dedicated storage. All of this is just steps from East Ukrainian Village's acclaimed restaurants, cafes, boutiques, parks, and nightlife-one of Chicago's most sought-after neighborhoods.

1817 W Iowa Avenue Unit #3, Chicago

$649,900

2 Beds ⋅ 2 Baths ⋅ 12701095 MLS ⋅ ACTIVE Status

Experience the perfect harmony of sophistication and urban convenience in this sun-drenched East Village penthouse. Nestled on a quiet, tree-lined street, this top-floor residence features an expansive open-concept layout defined by gleaming hardwood floors, custom fireplace built-ins, and a chef-inspired kitchen equipped with granite countertops and high-end appliances. The primary suite serves as a true private retreat, boasting a spa-like bath with a dual vanity, jetted tub, and separate shower. With a new in-unit washer/dryer, updated furnace and A/C, and an integrated sound system, this home offers turn-key comfort in the heart of Chicago's most coveted neighborhood. Step outside to your large rear deck, where a custom spiral staircase provides direct access to an incredible rooftop opportunity - the perfect canvas for creating your own private skyline sanctuary. Located just minutes from the CTA, renowned boutiques, and the vibrant dining scene of Wicker Park, this home is more than just a property; it is an exceptional lifestyle opportunity. Schedule your private tour today to secure this rare East Village gem.

876 N Hermitage Avenue Unit #3, Chicago

$1,200,000

3 Beds ⋅ 3 Baths ⋅ 12706738 MLS ⋅ ACTIVE Status

We are excited to introduce 2023 W Augusta, Ukrainian Villages newest boutique luxury development. Built by highly experienced developers, this five unit building sits on an extra wide 48 foot lot, providing expansive floor-plans and exceptional natural light. Penthouse homes consist of Three large bedrooms and 2 1/2 bathrooms with fully finished private roof decks with city and skyline views. Nearly completed and ready for Occupancy no detail has been overlooked. In the main living space, expansive ceiling heights are anchored by large direct vent gas fireplaces with custom built-ins and stone surrounds. The custom built kitchen features white oak cabinetry, oversized island with beautiful white quartz waterfall counters, full hight back splash, all stainless Bosch appliances and undercount lighting. The oversized primary bedrooms include custom built walk-in closets and a serene primary bath with heated floors, dual vanity, glass encased shower and sleek soaking tub. 2nd and 3rd bedrooms are spacious and filled with natural light. Additional features include 3/4" Oak hardwood flooring throughout, Oversized crow moldings, full size in-unit Front Load laundry and on-site garage parking. Some Lighting still available for Selection.

2023 W Augusta Boulevard Unit #3E, Chicago

$995,000

5 Beds ⋅ 5 Baths ⋅ 12685461 MLS ⋅ ACTIVE Status ⋅ Terraces Of Old Irving BLDG.

Enjoy maintenance-free living in the largest Single Family model of The Terrances of Old Irving Park! Nestled in a secure cul-de-sac, this newly renovated 5BR 4.5BA 4000+ sf hidden oasis features open floor plan with formal living, formal dining, granite black-SS kitchen with eat-in island and breakfast area, generous family room with gas fireplace and a large barbecue deck overlooking a private brick yard. Next to kitchen are the conveniences of two offices, movie theatre (or homeschool classroom), mudroom, oversized walk-in pantry with a 2nd frig. The magnificent 14-foot-tall master suite offers cathedra ceilings, wet bar, fireplace, two walk-in closets and an electric staircase access to a bonus room. The Carrara Marble master bath has steamer, skylight rain double-shower, dual Jacuzzi, and a make up station. Entertain yourself in the bright English basement featuring 9 large windows, wet bar, spacious gym, game room, sewing/craft station and the 5th BR. All 5 large bedrooms have private full bath access with bidet setups. 2 Jacuzzis, 3 sets of washers/dryers. 3 sets of HVAC systems, oversized attached heated garage with electric car charger, a large workshop with sink, and 150 sf walk-in storage. Owner-managed association provides private tennis court, basketball court, pet park, nature-walking trail, and covers lawn care, snow removal, water/sewer/garbage bills. Amazing schools! Walk to parks, playgrounds, YMCA, grocery, blue line/Metra/bus, a new hospital. 2 minutes from the highway exit Koster, minutes to stores, restaurants. Broker owned property. Seller financing available! Schedule a showing today!

4249 N Kolmar Avenue Unit #4249, Chicago

$379,000

3 Beds ⋅ 3 Baths ⋅ 12643217 MLS ⋅ ACTIVE Status ⋅ Galewood BLDG.

Beautiful and spacious two-story penthouse in Chicago's desirable Galewood neighborhood offering 3 bedrooms, 2.5 bathrooms, and approximately 1,500 square feet of living space. This well-maintained home features an open-concept living and dining area filled with natural light, hardwood floors, soaring 9-foot ceilings, and a cozy gas fireplace. The large eat-in kitchen is designed for both everyday living and entertaining, featuring 42" European cabinetry, granite countertops, top-of-the-line stainless steel appliances, an oversized island, and abundant storage space. A beautiful staircase leads to the second level, creating a unique and functional layout with generously sized bedrooms and flexible living space. Enjoy three private balconies, providing plenty of room for relaxing or entertaining. The spacious primary suite offers a walk-in closet and a private spa-like bath featuring a jetted soaking tub and body jets for a true spa experience at home. The additional full bathroom also offers luxury finishes and features a steam shower with built-in bench seating and integrated controls designed to create a relaxing steam room experience. The home includes an in-unit washer and dryer. Conveniently located near the Galewood Metra station, shopping, restaurants, parks, and other neighborhood amenities. A dedicated parking space is also included. A maximum of two pets are permitted. Property is being sold AS-IS.

6906 W Medill Avenue Unit #2E, Chicago

Start Your Search

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 our company are marked with the MRED Broker Reciprocity logo or the Broker Reciprocity thumbnail logo (the MRED logo) 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 accuracy of all information, regardless of source, including but not limited to square footages and lot sizes, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. 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.

Copyright 2026 MRED LLC. All rights reserved.

Based on information submitted to the MLS Grid as of . All data is obtained from various sources and has not been, and will not be, verified by broker or MLS Grid. MRED supplied Open House information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the DMCA) provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to DMCAnotice@theMLSGRID.com.

The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner’s behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.

Some listings have been excluded from this website.