View All Uptown Chicago IL Penthouse Homes Listings

2 Beds ⋅ 2 Baths ⋅ 12698250 MLS ⋅ CLOSED Status

Enjoy penthouse living in this spacious 2-bedroom, 2-bath condo in the heart of Uptown, offering a functional layout, quality finishes, and an exceptional location. Oak hardwood floors, high ceilings, and abundant natural light enhance the open-concept living and dining area, complete with a gas fireplace for added warmth and character. The kitchen features granite countertops, 42-inch custom cabinetry, and newer stainless steel appliances, providing ample storage and workspace. The primary suite includes a marble ensuite bath with a dual-sink vanity, whirlpool tub, and separate glass-enclosed shower. A generously sized second bedroom offers flexibility for guests, a home office, or additional living space. The rear south-facing deck extends the living area outdoors and is ideal for relaxing or entertaining. Constructed of brick and limestone, the building also features a brand-new roof. One garage parking space and a dedicated storage unit are included. Conveniently located near the lakefront, Montrose Beach, Montrose Harbor, parks, walking and biking trails, neighborhood restaurants, shopping, and public transportation, including the Wilson Red Line station for easy access to downtown and beyond.

825 W Eastwood Avenue Unit #3W, Chicago

$450,000

2 Beds ⋅ 2 Baths ⋅ 12501461 MLS ⋅ CLOSED Status

This spacious 2 bed, 2 bath penthouse condo in an elevator building offers an impressive urban retreat with 10-foot ceilings and sunlit south-facing views. The open-concept living and dining area boasts a fireplace and hardwood floors, seamlessly connecting to a private balcony ideal for grilling and relaxation. The kitchen features stainless steel appliances and a large peninsula. The expansive primary bedroom includes a sitting area and luxurious en suite with a double vanity, soaking tub, and separate walk-in shower. Additional amenities include in-unit laundry and heated indoor parking. Residents can also enjoy a common rooftop deck with stunning views. Conveniently located with easy access to shopping, dining, parks, the CTA Wilson Red Line L Stop, and just a short distance from Montrose Beach.

4603 N Racine Avenue Unit #403, Chicago

$620,000

2 Beds ⋅ 2 Baths ⋅ 12494166 MLS ⋅ CLOSED Status

Live the dream in Andersonville in this extra-wide, 2 bedroom + Office duplex-up penthouse condo offering over 2,100 sq ft of sun-filled living space. The open layout features an island kitchen with white cabinets, granite countertops, and a mosaic tile backsplash, flowing into a spacious living room with hardwood floors and a gas fireplace. A dramatic wall of south-facing windows fills the home with light and overlooks the beautiful, tree-lined Winona Street. Upstairs, enjoy an enormous open loft area - perfect for a home office or family room. Meticulously maintained, this home includes numerous updates: new roof (2019), reinforced masonry (2020), skylight (2022), washer & dryer (2022), and newer appliances - oven ('22), dishwasher ('20), refrigerator ('25). The building is pet friendly with no special assessments planned and approx. $18K in reserves. Unit also has extra storage is in the basement. The deck was sealed in 2024. The six-unit building is self-managed, rentals are allowed, and the association has been extremely well cared for. Enjoy Andersonville's best just steps away - cafes, boutiques, and award-winning dining on Clark Street, plus nearby Argyle's "Little Saigon" and the Argyle Red Line stop. Experience bright, beautiful living in one of Chicago's most beloved neighborhoods.

1224 W Winona Street Unit #3E, Chicago

$425,000

2 Beds ⋅ 2 Baths ⋅ 12440836 MLS ⋅ CLOSED Status

Timelessly elegant corner penthouse, located in an intimate 12-unit elevator building in the heart of Uptown. This extra-wide, light-filled condo offers an expansive layout featuring spacious kitchen with stainless steel appliances, granite countertops, abundant cabinet storage and a breakfast bar that comfortably seats four. The adjacent dining area, with space for a large dining room set, flows seamlessly into the bright living room complete with a cozy gas fireplace and access to one of the two private balconies-perfect for relaxing or entertaining. Enjoy generously sized bedrooms with ample natural light and closet space. The luxurious primary suite easily fits a king-sized bed and includes two double-hung closets, second private balcony, and a spa-inspired en suite bath with a steam shower, separate soaking tub, and double vanity. The second bedroom is versatile-ideal as a bedroom, home office, or both. Central a/c, in-unit laundry, covered gated parking and separate storage cage complete this home. Have peace and quiet as the condo is not on the Sheridan side of the building. Ideal building offers on-site exercise room. Unbeatable location-walk to the lakefront, Wilson or Lawrence Red Line stops just two blocks away, neighborhood restaurants, shops, and iconic live music venues like the Green Mill, Aragon Ballroom, and Riviera Theatre.

4725 N Sheridan Road Unit #4C, Chicago

$560,000

3 Beds ⋅ 2 Baths ⋅ 12433185 MLS ⋅ CLOSED Status

Introducing an Andersonville sun-drenched 3 bed, 2 full bath sprawling the entire 2nd floor penthouse in an intimate 2 flat all brick building. Perfectly nestled on a picturesque treelined street in the heart of south Andersonville. Enter through your private interior staircase to the massive living area beaming with natural light from large south facing bay windows adjourned with exposed brick, a decorative fireplace, and high ceilings. Attached to the front-facing living room you will find one of two outdoor spaces - perfect for morning coffee or simply enjoying the neighborhood ambience. Back inside, you'll notice the generously sized living room offers cozy nooks for added charm and practicality to accommodate for modern living like a second home office or an additional dining area. The quintessential Chicago vintage layout effortlessly flows from the open living room to the bright and sizable kitchen. Eat-in kitchen recently updated with quartz countertops, a brand new range hood (actually exhausts to the exterior), new fridge, new dishwasher, new light fixtures and hardware, and features 32" cabinets including a custom pantry as well as stainless-steel appliances and timeless subway tile backsplash. An additional private deck attached to the kitchen for convenient grill-to-table summer nights and effortless lounging. Down the hall from the kitchen you'll find 3 bright bedrooms, 2 full bathrooms, a huge storage closet, a utility closet with a new water heater, and a stackable washer/dryer. Two of the three bedrooms will comfortably fit a king size bed plus furniture with sizable closets in each. The third bedroom does not have a closet and is best suited for a full size or smaller bed, home office, or hobby room. Both bathrooms are modernized and spacious with newer vanities and light fixtures, classic white tiles, and soaking tubs. Additional storage in the basement and 2 car parking in the extra-long tandem exterior parking space are included in the price. A+ location just 1 block from everything Clark St has to offer including the Farmers Market on Wednesdays, a bodega for last minute pick-ups, and tons of local hot spots like Bar Roma, Dollop, multiple cafes, Four-sided, Hop Leaf, Simon's, The Chicago Magic Lounge, Lady Gregory's, Andersonville Galleria, and so much more! This Andersonville condo is truly a rare find, offering charm and functionality in a prime location near multiple train and bus lines for an easy commute. With tons of shopping in a neighborhood dedicated to sustainability and local artisans, there is truly something for everyone. Make it yours and enjoy the ultimate urban living experience!

1464 W Carmen Avenue Unit #3, Chicago

$645,000

2 Beds ⋅ 2 Baths ⋅ 12357038 MLS ⋅ CLOSED Status

Flooded with natural light, this extra-wide penthouse in the heart of Andersonville offers rare indoor-outdoor living and exclusive roof rights with the potential to build a private rooftop deck and enjoy skyline views. With over 1,680 square feet, this top-floor 2 bed, 2 bath condo features a bright, open layout with soaring ceilings. The spacious living area includes a separate dining space, gas fireplace, custom built-ins, and a wall of west-facing windows. The kitchen is anchored by a granite island with bar seating and includes stainless steel appliances and ample cabinetry. Sliding doors lead to a front-facing balcony, perfect for morning coffee. The oversized second bedroom works well as a guest room and home office. The king-sized primary suite offers a walk-in closet, private balcony, and en-suite bath with dual vanity and walk-in shower with bench. The second full bath includes a soaking tub and built-in storage. Additional features include hardwood floors, recessed lighting, central air, in-unit laundry, an in-unit storage closet, and additional garage storage. Located in a well-maintained boutique building. Includes garage parking and a second covered carport space. The unbeatable location is just steps to Clark Street's shops, dining, nightlife, CTA access, and more! Sorry, no elevator.

5051 N Clark Street Unit #4S, Chicago

$337,500

2 Beds ⋅ 2 Baths ⋅ 12209761 MLS ⋅ CLOSED Status

Stunning top-floor penthouse condo with East and South exposures that bring in natural light throughout the day!! Open living at it's finest, with a kitchen, dining room and fireplace. In unit washer/dryer. Two tier exterior patio/deck and roof top with grill and plenty of seating areas. Water and cable/internet included in assessments. One gated parking included in price (#11). Minutes to Red Line, walk to parks, coffee shops, pubs, eateries and Lake Michigan! Come tour today!

1114 W Leland Avenue Unit #3B, Chicago

$465,000

2 Beds ⋅ 2 Baths ⋅ 12184513 MLS ⋅ CLOSED Status

SUNDAY OH CANCELED - SUNDAY OH CANCELED Enter into this stunning 2-bedroom 2-bathroom penthouse condo located in historic Uptown. You will be greeted with abundant natural light that fills the open concept living space that boasts soaring, vaulted ceilings. Your Juliet balcony overlooks a quiet tree lined street and your living room is centered on a cozy fireplace, ideal for those cold Chicago winters. The modern kitchen features 42" maple cabinets, granite countertops, a generous island, and plenty of storage. Down the hall you will find the guest bedroom, the in-unit laundry and the full guest bathroom. As you continue into the grand, primary suite, you will notice the high ceilings, an entire wall of closets for all the storage one could want, and a wonderfully light-filled en suite bath. Finally, you will come to the amply sized rear deck with access from the hallway or the primary suite, perfect for hosting gatherings, grilling, or your very own peaceful getaway. There are 2 garage spaces (one garage spot plus a car lift above). A short walk to lake Michigan, the Lawrence CTA Red Line station, endless restaurants, and entertainment all at your doorstep. Do not miss this opportunity!

849 W Lakeside Place Unit #3W, Chicago

$926,500

3 Beds ⋅ 2 Baths ⋅ 12069306 MLS ⋅ CLOSED Status

Rarely available top floor customized penthouse in one of Andersonville's premier condo buildings - the Renslow - a boutique 14 unit elevator building. This is the first penthouse unit available on the market since the building's 2021 debut. If you enjoy outdoor entertaining, you will love the 700 square foot private roof deck, which is the second largest in the building and situated in the desirable southeast corner. An Italian Pratic pergola is integrated with custom metal railings, wood privacy screens and Trex decking. Remote controlled sunshades, lighting and louvres make this pergola a showstopper, perfect for entertaining large groups who will be amazed at the dramatic view of the downtown Chicago skyline. Step inside the home for the epitome of modern and intimate luxury living. Located away from bustling Clark Street, this corner unit provides unparalleled privacy. Nestled amidst lush trees, the home beams with sunlight from large windows which provide both south and east exposure not to mention clearance above neighboring buildings. The interiors are accentuated by wide-plank white oak hardwood floors. You will love the spacious kitchen with its expansive island, built-in beverage fridge, microwave drawer, tall sleek cabinetry, striking black hardware, Thermador Professional Series appliances, and white quartz countertops with waterfall edges. Adjacent to the open-concept kitchen, the living and dining areas blend harmoniously, further enhanced by modern lighting fixtures and the home's second outdoor space. The high ceilings and 8-inch modern baseboards amplify the expansive feel of the home. Retreat to the luxurious master suite, boasting dual customized walk-in closets, a room spacious enough for a king-sized bed, and an en-suite bathroom with dual vanity sinks, radiant flooring, and a rejuvenating steam shower. The home's secondary and third bedrooms, situated in a distinct wing, offer both space and privacy. Additional features include built-in surround speakers throughout the home (entire Sonos system will be transferred), maximized organization with built-out closets in every room, convenient in-unit laundry, a secure attached garage parking space located next to an electric charging station with the option to rent a second parking space nearby, and a generously sized walk-in storage room on the first floor of the building. Andersonville, rich-in Swedish heritage, is renowned for its eclectic mix of independent shops, charming boutiques, and diverse eateries, offering residents a truly unique urban village experience. Close proximity to the Argyle Red Line and Lawrence Metra. Steps from all of the restaurants and shops: Bar Roma, Hopleaf, Meetinghouse, Calo, Jeni's Ice Cream, local coffee shops, Orange Theory, and much more. Schedule your private showing today and act fast on this amazing home!

5015 N Clark Street Unit #403, Chicago

$467,000

2 Beds ⋅ 1 Baths ⋅ 12056365 MLS ⋅ CLOSED Status

Gorgeous penthouse, available for the first time in 18 years located in the heart of Andersonville. This 2 bed 1 bath condo has all of its original woodwork, stained glass windows, hard wood floors throughout, and two sunrooms off of the front and back with both northern and southern exposure. This unit has a unique layout, with distinct spaces with a long hallway separating them allowing for an expansive feel. Off the entrance of the unit you find a large living room, gas fireplace with built-ins and a cozy sunroom. Down the hall you have two spacious bedrooms and bathroom. At the end of the hallway you enter into a sophisticated dining room with wainscoting which opens to the second sunroom off the back and into the updated kitchen. Brand new oven and dishwasher, with newer counter depth fridge. This kitchen has a nice blend of cabinetry and open shelving making this a dreamy space to cook in. Off the kitchen is a private porch that takes you to the shared backyard and garden space. Rounding out this top floor unit is a garage parking space included. Laundry in basement, with potential to add in-unit. The location of this property couldn't be better, a short stroll to Clark street where plenty of shopping and restaurants await and easy access to get to the lake.

1408 W Carmen Avenue Unit #3, Chicago

$375,000

2 Beds ⋅ 2 Baths ⋅ 12050847 MLS ⋅ CLOSED Status

ONE BLOCK FROM THE LAKE, at the nexus of Edgewater/Uptown/Andersonville. Gorgeous top floor end unit penthouse condo with high ceilings, warm exposed brick, & tons of natural light. Desirable split floor plan with 2 bedrooms & 2 full baths. Gourmet eat-in kitchen with all new stainless steel appliances (brand new 5/2024), granite counters, & balcony for grilling. Primary suite is generously sized with full en suite spa bath and separate private balcony! Large bay windows in living room. Full sized front-loader washer & dryer in-unit. Brand new (5/2024) Carrier central AC & forced air heat. Hardwood floors throughout. Custom paint 5/2024. Take the express bus & get downtown in 15 min! Four blocks to the heart of Andersonville! Easy street parking & monthly parking available close by. Super fast high speed fiber internet is available for an additional $30/mo. Building has newer roof (2014), and beautiful wrought iron gate surrounds the building. Steps to Mariano's, the lakefront, Argyle Red Line CTA, LSD, & buses, and everything Edgewater/Uptown/Andersonville have to offer!

1019 W Winona Street Unit #3, Chicago

$850,000

3 Beds ⋅ 2 Baths ⋅ 11951823 MLS ⋅ CLOSED Status

STUNNING 3 BED/2 BATH PENTHOUSE CONDO COMING TO MARKET SOON. NEWER CONSTRUCTION; OPEN FLOOR PLAN; 3 SEPARATE OUTDOOR SPACES WITH A MAGNIFICENT ROOF TOP DECK WITH GORGEOUS VIEWS--THE PERFECT ENTERTAINING SPACE. ONE CAR GARAGE.

1453 W Foster Avenue Unit #3, Chicago

$625,000

3 Beds ⋅ 3 Baths ⋅ 11955886 MLS ⋅ CLOSED Status

SPACIOUS, 3-STORY PENTHOUSE on a beautiful tree-lined street. This property lives like a single family home & has a wonderful extra-wide layout with large room sizes, real oak hardwood floors through out, high ceilings, tons of windows for great light & 2 private balconies; one off the living room & another off the master suite which has double sinks & luxurious steam shower & tub. This unique space is NOT like every other condo out there...starting with the gorgeous 2-sided custom fireplace between the living & dining rooms & the exceptionally large & open kitchen w/high-end quality appliances. This home is perfect for entertaining & has a 3rd floor family room that could also be a fantastic home office, studio or guest suite. All this JUST TWO BLOCKS FROM CLARK STREET with all its wonderful shops & restaurants, 1.5 BLOCKS FROM THE REDLINE "L" & 4 blocks from the lakefront & the Express Bus stop which takes you downtown in about 10 minutes.

1225 W Carmen Avenue Unit #2N, Chicago

$510,000

3 Beds ⋅ 2 Baths ⋅ 11837604 MLS ⋅ CLOSED Status

Welcome to this luxurious top-floor penthouse located in Uptown Chicago. Featuring an open floor plan with West and North exposure flooding the space with natural sunlight throughout the day. With three bedrooms and two full bathrooms, this spacious unit boasts elegant hardwood floors, crown molding, and an array of features that make it a perfect retreat. Make your way into the kitchen equipped with stainless steel appliances, granite countertops and a huge breakfast bar. Step into the primary bedroom that features an en suite bathroom with both a separate shower and a relaxing whirlpool tub. In addition to the primary suite, the second and third bedrooms are impressively spacious and come with ample closet space. The third bedroom has French doors and can be converted into an office space; den or a separate living area, offering you various options to make the most of the space. Cozy fireplace creates a warm ambiance on chilly nights. Covered parking space in a heated garage for added convenience and security. This penthouse condo offers your own private rooftop deck and separate patio where you can enjoy the stunning city view & front row seats to the Air and Water show. Now that is what I call luxury outdoor living without leaving your home! The owners have taken great care with all major items that are newer. Roof, rooftop decks, high-performance windows (2020). HVAC ,humidifier, and HWT (2018) Double coat deck staining (2022).Located just steps away from the new Wilson Red Line station and other transportation, making commuting a breeze. Close to everything Uptown and Sheridan Park have to offer, including Lake Shore Drive, Foster Dog Beach, shops, and many restaurants. Don't miss this opportunity to own a remarkable home in one of Chicago's most sought-after neighborhoods!!

4603 N Racine Avenue Unit #401, 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.

Uptown, Chicago IL · Curated MLS Search

Penthouse Homes in Uptown, Chicago IL

An editorially curated view of every active penthouse homes listing in Uptown, Chicago IL. Updated in real time from the local MLS, presented without the noise.

Browse Active Listings

Uptown, Chicago IL Market Snapshot

Inventory here shifts week to week. The listings on this page pull straight from the MLS, so what you see is what's actually for sale right now.

Next Steps in Uptown, Chicago IL

Speak with an Agent

Call (312) 788-7079

Local Uptown, Chicago IL expertise

Data Brief

Full Uptown, Chicago IL Market Report

Pricing trends & absorption

Browse Everything

All Uptown, Chicago IL Listings

Every active property

← Back to Uptown, Chicago IL Homes for Sale