Old Town Real Estate

Old Town Real Estate

Located in the heart of Chicago, Old Town is a vibrant and historic neighborhood that offers a unique blend of charm, culture, and convenience. Situated in Cook County, Illinois, this neighborhood is known for its rich history, tree-lined streets, and well-preserved Victorian-era architecture.

Old Town is a popular destination for both residents and visitors alike, thanks to its close proximity to downtown Chicago and its abundance of amenities. The neighborhood is home to a wide range of shops, boutiques, restaurants, and entertainment venues, making it a hub of activity throughout the year.

One of the highlights of Old Town is its thriving arts scene. The neighborhood is home to several theaters, including the famous Second City comedy club, where many renowned comedians got their start. Additionally, Old Town is known for its annual art fair, which attracts artists and art enthusiasts from all over the city.

In terms of housing, Old Town offers a mix of historic townhouses, single-family homes, and modern condominiums. The neighborhood's well-preserved architecture and tree-lined streets create a picturesque setting that is highly sought after by those looking for a charming and character-filled place to call home.

Old Town also boasts excellent transportation links, with easy access to major highways and public transportation options. This makes it convenient for residents to commute to other parts of the city or explore the wider Chicago area.

Overall, Old Town is a neighborhood that seamlessly combines history, culture, and convenience. With its charming streets, vibrant arts scene, and proximity to downtown Chicago, it's no wonder that Old Town remains a popular choice for those looking to experience the best of city living.

Newest Listings in Old Town

$1,450,000
3 Beds ⋅ 4 Baths ⋅ 12713927 MLS ⋅ NEW Status
One of the defining features of this home is its setting within Old Town Village East - a private, tree-lined horseshoe street that offers guest parking, a rarity in Chicago, and a gated alley where neighbors gather and children play. It is a neighborhood that offers an uncommon sense of community while remaining just minutes from the heart of the city. The home has been thoughtfully renovated with an emphasis on both design and functionality. The first floor was completely reconfigured to improve the original layout, including a remodeled kitchen, relocated powder room, and the addition of a walk-in pantry, creating a more practical and cohesive living space. The main level features custom millwork and wainscoting, while updated lighting, fixtures, switches, outlets, and integrated recessed lighting throughout provide a clean, contemporary aesthetic. Hardwood floors were added to the upstairs bedrooms, and the finished lower level includes two additional bedrooms and a spacious spa-inspired bath, offering exceptional flexibility for guests, extended family, or work-from-home needs. Ideally situated within walking distance of Old Town's restaurants and several of Chicago's most respected schools, including Latin, Walter Payton College Prep, Catherine Cook School, and Immaculate Conception/St. Joseph School (ICSJ), this home combines thoughtful renovations with an exceptional neighborhood setting. A private deck and landscaped outdoor space extend the living area outdoors, complemented by a detached two-car garage. Extensive recent capital improvements further enhance the home's appeal (Roof, Gutters, HVAC (2025/2026).

344 W Scott Street, Chicago
$395,000
2 Beds ⋅ 1 Baths ⋅ 12712810 MLS ⋅ NEW Status

1455 N Sandburg Terrace Unit #2009, Chicago
$4,600,000
10 Beds ⋅ 10 Baths ⋅ 12556436 MLS ⋅ ACTIVE Status

Chicago
$680,000
3 Beds ⋅ 2 Baths ⋅ 12700297 MLS ⋅ ACTIVE Status
Welcome to this spacious 3-bedroom, 2-bath residence in a boutique elevator building at the crossroads of Old Town and Lincoln Park, taking in the best of both neighborhoods! Featuring an open layout with dark hardwood floors, granite countertops, stainless steel appliances, a built-in wine fridge and a custom gas fireplace, this home offers both comfort and functionality. The generous primary suite includes organized closets and a spa-inspired bath with a dual vanity, soaking tub, and separate shower, while two additional bedrooms provide excellent flexibility. Enjoy two private terraces plus a shared rooftop deck with city views. Additional highlights include in-unit laundry, 1 outdoor parking space included, additional storage unit, and bike storage. Ideally located just steps from the Brown Line, Wells Street, restaurants, shopping, parks, and the lakefront.

409 W North Avenue Unit #2E, Chicago
$750,000
2 Beds ⋅ 2 Baths ⋅ 12686934 MLS ⋅ ACTIVE Status
Welcome home to this sun-drenched 2-bedroom, 2-bathroom condo in a boutique elevator building in the heart of Old Town. South-facing windows and soaring ceilings flood the space with natural light, starting with an wide formal foyer finished with custom wall treatments. The updated white kitchen features granite countertops, a tile backsplash, under-cabinet lighting, and a generous peninsula perfect for casual dining-plus a new stove, refrigerator, and dishwasher installed in 2023. It flows seamlessly into an expansive living and dining room anchored by a gas fireplace, and out to a south-facing balcony with sweeping city views, ideal for morning coffee or evening drinks. The primary suite is a true showstopper: at 19 feet wide, it rivals bedrooms in single-family homes, complete with a custom walk-in closet and a spa-like marble bath featuring double sinks, a separate shower and tub, and a linen closet. The second bedroom, also south-facing, is equally gracious, and a well-appointed hall bath rounds out the layout. Both bedrooms have newer carpeting, installed in 2024. Additional highlights include 8-inch wide-plank wood floors, abundant custom closet storage throughout, an in-unit stackable washer/dryer, and a Nest thermostat. A storage unit and heated garage spot #G-16 are included. This well-managed, pet-friendly (max of 3 pets) brick building added a new video doorbell security system. Enjoy an unbeatable location just steps from shopping, restaurants, the lake, and the park. Rentals permitted with a minimum 1-year lease. Monthly HOA: $676.36 ($637.95 / unit & $38.78 / parking) & 2024 Taxes: $14,083.56 w/no exemptions ($13,276.74 /unit & $806.82 / garage parking)

1429 N Wells Street Unit #502, Chicago
$4,600,000
12703290 MLS ⋅ ACTIVE Status
Premier Old Town Development & Cash-Flow Opportunity | Double or Triple Lot Package. An unmatched development canvas awaits in the heart of Old Town, one of Chicago's most coveted and historic enclaves. This rare offering features a flexible double or triple-lot footprint situated on a premier, tree-lined residential street. The package combines immediate high-yield rental income with immense ground-up development potential for a landmark residential or commercial project. The Development Footprint: Rare double or triple-lot ideal for luxury single-family homes, high-end condominiums, or commercial assets. Ready Accessibility: Features an existing curb cut, significantly simplifying site planning and construction logistics. Favorable Zoning: Versatile zoning parameters accommodate diverse architectural visions and maximize buildable square footage. The Income Generator (1455 N. Sandburg) Turnkey Asset: A beautiful, fully leased brick multi-family building anchoring the third parcel to provide immediate carrying income. Upper-Level Units: Three pristine, layout-efficient 2-bedroom, 2-bathroom apartments commanding premium neighborhood rents. Garden-Level Space: An expansive 5-bedroom, 5-bathroom footprint, currently optimized as high-end office space. A Location Without Equal Transit-Oriented: Located just steps from the Sedgwick CTA Brown Line station and express buses on LaSalle Street for effortless commuting. Gold Coast & Lake Access: Walking distance to the shores of North Avenue Beach and the vast green spaces of Lincoln Park. Lifestyle & Amenities: Minutes from the world-class dining, boutique shopping, and vibrant nightlife lining iconic Wells Street.

1455-59 N Sedgwick Avenue, Chicago
$575,000
2 Beds ⋅ 3 Baths ⋅ 12701805 MLS ⋅ ACTIVE Status
Elegant and rare 2 bedroom, 2.5 bath duplex-down condo in the heart of Old Town. This bright and airy home offers an ideal floor plan with generous living and entertaining space across two levels. Recent updates include windows, appliances, furnace, and high-efficiency water heater, providing modern comfort and energy efficiency for years to come. The main level features an open concept living and dining area with abundant natural light which includes a private balcony for seamless indoor and outdoor entertaining. The lower level offers two well-appointed bedrooms and ample storage. The primary suite includes a private bath with a luxurious shower and excellent closet space. Enjoy the convenience of an unbeatable location near parks, restaurants, shopping, and public transportation. Despite its proximity to the train, the unit is remarkably quiet; train noise is virtually unnoticeable from inside the home. 1 outdoor parking spot is included in the price. A rare opportunity to own a move-in-ready and turn-key residence in an unbeatable location.

308 W Evergreen Avenue Unit #1R, Chicago
$275,000
2 Beds ⋅ 1 Baths ⋅ 12701664 MLS ⋅ ACTIVE Status
Sun- Filled, South Facing 2 Bedroom with views of the City and Courtyard. Features impressive hardwood floors, a modern kitchen with granite counters and breakfast bar, New Oven/Range, and New Bedroom Carpeting. An array of Amenities include: 24-hour Door Person, Elevator, Rooftop, Exercise Room, Health Club, 2 Swimming Pools and Sundeck. Rental Garage parking space available. On site Laundry Facilities, Tennis Courts and Bike Room included. This location is an excellent choice for residing in the Old Town Gold Coast Area and steps away from the Lakefront, Lincoln Park, Dining, Shopping, and Public Transportation. Sandburg Village presents a wonderful opportunity to experience the City of Chicago at its finest.

1460 N Sandburg Terrace Unit #803A, Chicago
$340,000
1 Beds ⋅ 1 Baths ⋅ 12697701 MLS ⋅ ACTIVE Status

1560 N Sandburg Terrace Unit #2708J, Chicago
$285,000
1 Beds ⋅ 1 Baths ⋅ 12654505 MLS ⋅ ACTIVE Status ⋅ Sandburg Village BLDG.
Welcome home to this updated south facing condo with sweeping skyline city views from this high floor condo in Old Town. Nothing to do but move in and enjoy city living! This location cannot be beat, Lincoln Park, Wells Street, North Avenue Beach and Michigan Avenue are all right outside your front door. Features include an open kitchen floorplan with extra wide layout, new flooring and fresh paint throughout, granite countertops, stainless steel appliances, and an oversized bedroom that easily fits a king size bed. Built-in 1962, Alcott House is pet friendly and offers 24/7 Doorstaff, on-site management and engineering staff, common laundry, sundeck, fitness center, new hallways, bike room, receiving room and a beautiful sophisticated lobby to welcome you home. Sandburg Village offers two pools and private tennis courts for a small additional yearly fee. Rental parking is available with a wait list, check SpotHero for other nearby options. Sorry, in unit laudry is not permitted. Book your private viewing today. don't miss out on this fantastic opportunity!

1460 N Sandburg Terrace Unit #2303A, Chicago
$347,900
1 Beds ⋅ 1 Baths ⋅ 12696244 MLS ⋅ ACTIVE Status ⋅ Gold Coast Galleria BLDG.
Welcome to this immaculate, fully renovated 1-bedroom, 1-bathroom condo in the heart of Old Town! This stunning residence offers breathtaking views, modern finishes, and a bright, open layout designed for comfortable city living. Perfectly situated just steps from the lake, parks, restaurants, shopping, and public transportation, you'll enjoy the best of everything Old Town has to offer right outside your door. This beautifully maintained, full-amenity building features a 24-hour doorperson, outdoor swimming pools, pickleball courts, a rooftop deck with spectacular skyline and lake views, and a beautifully landscaped courtyard that's perfect for relaxing or walking your dog. Whether you're looking for your first home, a city retreat, or a move-in-ready investment, this exceptional condo offers the perfect blend of luxury, convenience, and lifestyle. Don't miss your opportunity to own a piece of one of Chicago's most sought-after neighborhoods!

1455 N Sandburg Terrace Unit #2306B, Chicago
$815,000
3 Beds ⋅ 3 Baths ⋅ 12687381 MLS ⋅ ACTIVE Status ⋅ Cleveland Court BLDG.
Rarely available and beautifully updated, this sun-drenched exterior townhome in sought-after Cleveland Court offers the perfect blend of space, style, and an unbeatable Old Town location. Overlooking picturesque, tree-lined Blackhawk Street, the home is filled with natural light from four expansive bay windows and features a wide floor plan, soaring ceilings, and newer hardwood floors throughout. Designed for both everyday living and effortless entertaining, the penthouse level boasts a dry bar and an expanded private cedar rooftop deck where you can enjoy Chicago skyline views. The bright and spacious main living level showcases floor-to-ceiling windows, a generous living room with custom remodeled cabinetry surrounding the gas fireplace, a dedicated dining area large enough for hosting family and friends, and an additional flex space ideal for a sitting area or play space. The well-appointed kitchen features maple cabinetry, granite countertops, a breakfast bar, and premium Bosch, Fulgor, and GE Profile appliances, including a new range (2025) and oven (2023). The redesigned bedroom level offers a true retreat, featuring a spacious primary suite with a beautifully remodeled ensuite bath and professionally organized closets. A second bedroom, full bath, private office with French doors, and a cozy den provide exceptional flexibility for today's lifestyle. On the entry level, a true third bedroom with an ensuite bath offers endless possibilities as a guest suite, family room, game room, or private retreat. Additional highlights include all new Pella windows and window treatments (2024) throughout, new HVAC (2024), a dedicated laundry/utility room with side-by-side washer and dryer, an attached one-car garage, and a second parking space on the apron. Step outside and enjoy one of Chicago's most desirable neighborhoods. Just moments from Wells Street's renowned restaurants and boutiques, the Sedgwick Brown Line station, parks, beaches, NewCity, and the Clybourn Corridor, this exceptional home places the very best of Old Town, Lincoln Park, and the Gold Coast at your doorstep. Move-in ready, meticulously maintained, and rarely available-this is the one you've been waiting for. Schedule your private showing today before this exceptional opportunity is gone.

453 W Blackhawk Street, 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.