Old Town Homes with Roof Deck Exterior features

Our website features the best real estate search for homes, condos, land and foreclosure properties available in Old Town 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 Old Town Homes with Roof Deck Exterior features

$385,000

2 Beds ⋅ 1 Baths ⋅ 12764375 MLS ⋅ Old Town Square BLDG.

This beautifully maintained home features hardwood flooring throughout and a cozy wood-burning gas fireplace in the living room. The open kitchen is a standout, with granite countertops, an under-mount sink, and a stylish backsplash. In-unit washer/dryer and organized closets add everyday convenience. 2nd bdrm does not have a window, could also be a great office or den space! A tandem exterior parking space is included, along with an outdoor area perfect for grilling or relaxing and a common roof deck. This Old Town gem is set in a private gated courtyard right across from a park. This home offers the best of Old Town living - minutes from shops, restaurants, grocery stores, and much more.

301A W Goethe Street Unit #201, Chicago

230 W Division Street Unit #1501, Chicago

$599,000

2 Beds ⋅ 2 Baths ⋅ 12712603 MLS

Experience elevated city living in this exceptional designer corner penthouse, ideally situated in one of Old Town's most sought-after residential buildings - The Venetian. This stunning 2BR/2BA + Den is located in the heart of Old Town. It offers unbelievable southern & western skyline views from the open living/dining rooms which open to your wrap around balcony. It is an entertainers dream! Adorned with Brazilian cherrywood flooring, the home boasts soaring 11-foot ceilings which give the space a grandness that truly set it apart. The primary suite has both northern and western exposure with beautiful views of Lake Michigan. It features a massive walk-in closet with custom built in's and a large marble bathroom with dual vanity & shower/tub combo. The 2nd bedroom also features lake views as well as a large closet with built in's. There is also a large partially enclosed den that functions as a great office/flex space. The building has a top notch fitness center, rooftop deck, beautiful garden terrace, and 24 hour door person. Heated deeded garage parking for Additional $30k.

230 W Division Street Unit #1501, Chicago

$759,900

3 Beds ⋅ 2 Baths ⋅ 12751067 MLS

WELL DESIGNED AND OVERSIZED THREE BEDROOM CONDO IN OLD TOWN OFFERS A SPACIOUS AND FUNCTIONAL FLOORPLAN. THIRD FLOOR UNIT WITH TREE LINED VIEWS AND GREAT NATURAL LIGHT. UPDATED KITCHEN WITH WHITE CABINETRY, MARBLE COUNTERTOPS AND BACKSPLASH, FISHER & PAYKEL APPLIANCES, AND ISLAND WITH BREAKFAST BAR. LARGE LIVING ROOM WITH GREAT WINDOWS, GAS FIREPLACE WITH TRAVERTINE SURROUND, AND SEPARATE DINING AREA. XL PRIMARY SUITE WITH WALK-IN CLOSET, MARBLE BATH WITH DUAL SINK VANITY, AND ACCESS TO REAR DECK. SPACIOUS SECONDARY BEDROOMS AND RENOVATED FULL BATH WITH WALK-IN STEAM SHOWER. SIDE BY SIDE LAUNDRY. THIS UNIT FEATURES HARDWOOD FLOORING THROUGHOUT, CUSTOM TRIM WORK, CROWN MOLDING, WAINSCOTING, RECESSED LIGHTING, 9' CEILINGS, AND GENEROUS STORAGE THROUGHOUT. PRIVATE ROOF DECK WITH PERGOLA, BUILT-IN DINING TABLE, AND VIEWS OF OLD TOWN. GARAGE PARKING INCLUDED. WALKABLE TO WELLS ST, LINCOLN PARK, TRANSPORTATION, AND MORE.

1547 N Hudson Avenue Unit #3, Chicago

1360 N Sandburg Terrace Unit #2701C, Chicago

$534,900

2 Beds ⋅ 2 Baths ⋅ 12761116 MLS

Presenting this spectacular brand new gut renovated rare two bedroom two bathroom, corner unit with balcony on the 27th floor of Cummings House. Be the first to live in this unit with a modern open floor-plan that takes advantage of the wide open views across the city and lake. The workmanship and finishes are to the highest standards. Central to the unit is the open chef's kitchen where you can enjoy cooking and entertaining while taking in the stunning views.The custom cabinets are white gloss flat panel with black accent hardware, under-cabinet LED lighting. Quartz counters and a large island with waterfall edge and breakfast bar. High end appliances - French-door refrigerator, Bosch panel dishwasher, Sharp microwave drawer, slide-in range. Finished with black/gold lighting and new recessed led lights. The kitchen flows into the dining area which has a matching white gloss flat panel built-in credenza with additional cabinet storage. The open spacious living room has two full exposures of windows creating a bright airy feel. The large balcony has sliding doors from the living room to provide the perfect outdoor extension of the living space, relax enjoying a lake breeze with lake views to the east, city skyline to the south and beautiful sunsets to the west. The floor plan provides for a split layout of the two bedrooms and bathrooms. The bedrooms are both very spacious and have professionally organized closets with automated lights, recessed LED lighting overs the beds, they also have space to accommodate a desk area. The bathrooms are fully rehabbed- new walk-in shower with rain head and body sprays, sliding glass door, fully tiled in contemporary style, new vanity with quartz top, finished with black/gold accented fixtures, hardware, large mirror & lighting. Throughout the unit there are new wide plank light wood color floors, new electrical, new plumbing, new recessed led lighting. Painted throughout with contemporary soft color palette. There is plenty of storage in the unit, all professionally organized, also a storage cage is included in the building. Cummings House is a well run building with good reserves, many recent major updates completed including new elevators and renovated hallways & laundry room, facade restoration. There's a rooftop sundeck, 24 hour door staff, maintenance & management are onsite. Monthly assessment includes heat, TV cable and high speed (1GB) internet service (everything except electricity). Leased parking in attached parking garage currently has a waitlist. Sandburg Village amenities include 2 outdoor pools & sundecks, tennis courts, hospitality rooms- (some additional fees) The landscaped courtyards, play lot, commercial facilities provide a welcoming community environment. Highly desirable location, convenient for transportation - 1 block to train/subway, buses at door, access to Lake Shore Dr, bike path. Nestled between Gold Coast / Old Town, close to downtown, Lincoln Park. Enjoy all attractions of the neighborhood - restaurants, nightlife, shopping, new Jewel, Lakefront trail, beach, Investor friendly building (no rental cap, no Airbnb) Pets allowed.

1360 N Sandburg Terrace Unit #2701C, Chicago

$485,000

2 Beds ⋅ 1 Baths ⋅ 12754756 MLS

This beautifully updated 2-bedroom condo in a boutique 4-unit building in desirable Old Town checks every box that matters in real estate: price, value, and location. Between the low property tax ($4,779 in 2025) and modest HOA dues ($245/month), the overall cost of ownership here comfortably beats renting a comparable unit in the neighborhood. Numerous major updates, including designer kitchen(2025), water heater (2023), new roof, furnace / air conditioning, and maintenance-free high efficiency Andersen windows (all in 2020), alleviate just about all other financial worries. Nothing about this home is generic; rather, it showcases exquisite detail, including elegant tray ceilings, refinished hardwood floors, fresh neutral paint throughout, and new carpeting in both spacious bedrooms. In-unit laundry and deeded / gated parking space included. Common amenities include a massive roof top deck with sweeping Chicago skyline views. Location undeniably second to none. This quiet nook on the outskirts of the vibrant Old Town entertainment district is 5 min. to Brown line Sedgwick stop, 10 min to Redline North / Clybourn, 20 min. to North Ave Beach, and everything in between! A block away, set in a backdrop of iconic Chicago skyline, brand new beautifully designed Chicago Park No. 598 at 1514 N. Larrabee, easily rivals a historic Oz park, featuring a playground, adult outdoor fitness area, running track, state-of-the- art dog park, and vast green spaces. An extra perk for this amazing location is permit street parking always and readily available. This unmatched synergy of value and premier location offered by this incredible condo simply cannot be replicated.

1407 N Mohawk Street Unit #1, Chicago

$480,000

2 Beds ⋅ 2 Baths ⋅ 12753995 MLS ⋅ Old Town Square BLDG.

Discover your dream urban retreat in the heart of Chicago's dynamic Old Town with this captivating top-floor, 2-bedroom, 2-bathroom sanctuary. Step into luxury as you enter this meticulously crafted residence boasting an updated kitchen, sleek hardwood flooring throughout the main living area, and the cozy ambiance of a gas fireplace. Embrace the serenity of your own private balcony with treetop and courtyard views, perfect for unwinding after a busy day in the city. Indulge in the comfort of the primary bedroom, featuring a spacious walk-in closet and an ensuite bathroom for ultimate relaxation. A generously sized second bedroom awaits, accompanied by another full bathroom steps away. Ascend to the common roof deck and be mesmerized by panoramic views of Chicago's iconic skyline, a breathtaking backdrop to your urban lifestyle. Your slice of heaven awaits just one floor above you. Don't miss the opportunity to make this gem your own and experience the epitome of city living in style. 2 parking spaces (tandem space, front to back) included!

301 W Goethe Street Unit #304C, Chicago

1455 N Sandburg Terrace Unit #2306B, Chicago

$319,900

1 Beds ⋅ 1 Baths ⋅ 12753898 MLS ⋅ Gold Coast Galleria BLDG.

Welcome to this stunning, fully renovated 1-bedroom, 1-bathroom condo perfectly situated on the border of Gold Coast and Old Town! This updated residence features breathtaking east-facing views, modern finishes, and a bright, open layout designed for effortless city living. Throughout the home, you'll find an expansive kitchen with island seating, ample closet space, an electric fireplace, and a stylishly renovated bathroom. The well maintained community offers an impressive array of amenities, including a 24-hour doorperson, outdoor swimming pools, pickleball courts, a rooftop deck showcasing spectacular skyline and lake views, and a lush, landscaped courtyard. The location is hard to beat being just a few blocks to Wells Street, Lincoln Park, the Lakefront, and Division St. Whether you're searching for your first home, a city retreat, or a move-in-ready investment, this exceptional condo delivers the perfect combination of style, convenience, and location. Don't miss the opportunity to call one of Chicago's most sought-after neighborhoods home! No rental cap, parking available for lease through the building.

1455 N Sandburg Terrace Unit #2306B, Chicago

1360 N Sandburg Terrace Unit #2912, Chicago

$486,000

2 Beds ⋅ 2 Baths ⋅ 12730600 MLS

Rarely available top-floor corner penthouse at Cummings House! This beautifully renovated 2-bedroom, 2-bath residence features a private balcony and spectacular northwest views stretching from Lake Michigan across the Chicago skyline to the western horizon-enjoy gorgeous light and views from sunrise to sunset. Recent renovations include a custom kitchen with marble countertops and newer stainless-steel appliances, newer A/C units, refinished window interiors, custom closets in both bedrooms, and upgraded bathroom with plumbing improvements. Cummings House is a well-managed building with healthy reserves, new elevators, renovated hallways, 24-hour door staff, onsite management and maintenance, plus a rooftop sundeck conveniently accessible from this floor. Sandburg Village amenities include two outdoor pools, tennis courts, sundecks, hospitality rooms, and landscaped courtyards. Ideally located between Gold Coast and Old Town, just one block from the train and minutes from the lakefront, beaches, dining, shopping, nightlife, and Lincoln Park. Investor-friendly with no rental cap. Pets allowed. Garage parking only $165/month.

1360 N Sandburg Terrace Unit #2912, Chicago

$5,200,000

7 Beds ⋅ 6 Baths ⋅ 11755660 MLS

Nestled on the prestigious North Park Avenue, Significant Mansion stands as a remarkable architectural gem in the vibrant Old Town/Gold Coast neighborhood. This custom-built residence, constructed from exquisite masonry brick and limestone, spans an impressive 8,000 square feet and occupies a generous double lot measuring 50 feet in width. The property boasts an expansive side yard and entrance, multiple balconies, and a covered rooftop deck, crowned by a magnificent turret tower that presents breathtaking panoramic views of the city skyline and the lush, tree-lined surroundings. Featuring seven bedrooms and five and a half bathrooms, this home is a testament to meticulous design and thoughtful attention to detail. Inside, the residence showcases soaring 12-foot ceilings, rich hardwood flooring, a coffered ceiling in the living room, elaborate crown moldings, and stately 8-foot doors. The ambiance is further enhanced by three elegant wood-burning fireplaces, a five-stop elevator, and a well-appointed gym on the top floor that overlooks an impressive professional indoor basketball court. The spacious chef's kitchen is a culinary enthusiast's dream, equipped with a Wolf range cooktop and custom copper hood, built-in Wolf convection ovens, a commercial Thermador refrigerator, and luxurious granite countertops. Custom cabinetry, a large center island with counter seating, and a separate dining area create a seamless flow into the grand family room, which features yet another wood-burning fireplace. The spectacular three-season room invites relaxation with its own wood-burning fireplace and provides access to an outdoor grilling patio complete with a built-in DCS chef's grill. The home also includes a convenient mudroom with laundry facilities and direct access to the stunning side yard. The expansive primary suite is a private retreat, featuring a walk-out balcony, a dedicated staircase leading to a unique turret office, and two generous walk-in closets. The en suite bathroom is a luxurious haven, offering a double vanity, a spacious steam shower, and a jetted bathtub. Additional bedrooms are equally generous, each equipped with walk-in closets, en suite baths, and walk-out balconies. The lower level is designed for entertainment, featuring a cozy fireplace and a potential wine storage room, alongside two sizable bedrooms with walk-in closets and a full bath. Additional highlights of this extraordinary residence include a spacious attached 2.5-car garage, an automated privacy gate, a snowmelt driveway, a central vacuum system, geothermal radiant heating, Marvin windows, multiple laundry rooms, and a Sonos multi-room sound system throughout the home. Perfectly suited for entertaining large families, this unique property is ideally located near a wealth of entertainment options, exquisite dining, top-tier schools (including Latin and Parker), parks, and the picturesque lakefront. This is truly a one-of-a-kind home that promises an unparalleled living experience.

1515 N North Park Avenue, 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.