Old Town Real Estate

Old Town Real Estate

Welcome to Old Town, a vibrant neighborhood nestled in the heart of Chicago, Illinois. Known for its rich history and eclectic charm, Old Town is a unique blend of old-world architecture and contemporary living that captivates residents and visitors alike. Once a hub for the city's German immigrants in the 19th century, this area has transformed into a lively community that celebrates its heritage while embracing modernity.

Strolling through Old Town, you'll be enchanted by the picturesque tree-lined streets and beautifully preserved Victorian-era buildings. The iconic St. Michael's Church stands as a testament to the neighborhood's historical roots, while trendy boutiques, art galleries, and cozy cafes line the bustling avenues. The area is also home to the renowned Second City comedy club, where laughter and creativity thrive, making it a cultural hotspot for entertainment enthusiasts.

Old Town is not just a feast for the eyes; it’s also a haven for food lovers. With an array of dining options, from upscale restaurants to charming bistros, there’s something to satisfy every palate. The weekly farmers' market is a must-visit, offering fresh produce and artisanal goods that showcase the local flavor.

Families will appreciate the close-knit community feel, excellent schools, and nearby parks that provide ample green space for outdoor activities. With easy access to public transportation, Old Town is just a stone's throw away from downtown Chicago, offering the perfect balance of urban convenience and suburban tranquility.

Whether you’re looking to buy a home or simply explore, Old Town is a neighborhood that invites you to experience its warmth and character. Come discover why so many have chosen to call this charming enclave their home!

Newest Listings in Old Town

$489,900
2 Beds ⋅ 2 Baths ⋅ 12644953 MLS ⋅ NEW Status ⋅ 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
$839,000
3 Beds ⋅ 2 Baths ⋅ 12723464 MLS ⋅ NEW Status ⋅ River North BLDG.
Welcome home to this sun-drenched 3-bedroom, 2-bathroom penthouse at The Stanton-a boutique 14-unit elevator building perfectly positioned where River North meets Old Town. This top-floor, east-facing residence boasts an expansive open floor plan flooded with morning light and seamless indoor-outdoor living with a private, oversized deck right off the main living space. Modern, high-end finishes span throughout, highlighted by a chef-caliber kitchen designed for effortless entertaining. All three bedrooms offer generous footprints and deep storage, including dual walk-in closets in the primary suite. The primary ensuite serves as a private spa, complete with a walk-in steam shower, double vanity, and a deep Jacuzzi tub. Unmatched urban convenience comes built-in: two heated garage parking spaces, a dedicated storage unit, bike storage, and a shared rooftop deck with panoramic skyline views. Step outside your door to Target, Mariano's, Jewel-Osco, Starbucks, and New City, with the vibrant dining, nightlife, and boutique shopping of Wells Street just a half-mile away.

1317 N Larrabee Street Unit #401, Chicago
$375,000
2 Beds ⋅ 2 Baths ⋅ 12718745 MLS ⋅ NEW Status ⋅ Alcott House BLDG.
Welcome to effortless city living at Alcott House in Sandburg Village! This spacious and sun-drenched 2-bedroom, 2-bathroom corner condo delivers an incredible blend of comfort, style, and iconic Chicago views. Oversized windows wrap the home in natural light, framing stunning panoramas and breathtaking views of the city skyline, Lincoln Park, and Lake Michigan. Step right out from the large living room onto your private oversized balcony, the ultimate spot for morning coffee or evening sunsets against the backdrop of the skyline. The expansive living room flows seamlessly into the adjacent dining area, creating an ideal setup for entertaining. An updated kitchen features a spacious layout open to the living and dining spaces, complete with a convenient breakfast bar for casual meals or a bright workspace. Generously sized bedrooms are thoughtfully separated for maximum privacy. The primary bedroom overlooks Lincoln Park with gorgeous lake views and features an adjacent updated primary bathroom boasting an oversized walk-in shower and sleek white tile and fixtures. The second bedroom offers fantastic versatility as a guest room, home office, or den. Alcott House Amenities feature a 24-hour doorman, responsive on-site maintenance staff, a scenic rooftop deck, a newly renovated laundry room, on-site dry cleaners, and an assigned storage locker. Sandburg Village offers access to a fantastic fitness center, outdoor pools and tennis/pickleball courts (seasonal) all available with nominal membership fees. This prime location is perfectly nestled at the vibrant intersection of Old Town and the Gold Coast, putting the best dining, shopping, transit, and lakefront recreation right outside your door.

1460 N Sandburg Terrace Unit #1412A, Chicago
$815,000
3 Beds ⋅ 3 Baths ⋅ 12726187 MLS ⋅ NEW Status
Experience the comfort and space of a single-family home in this expansive Old Town duplex, offering approximately 2,000 square feet of interior living space plus 350 square feet of private outdoor areas. Nestled within a charming, classic Chicago brick building, this exceptional residence combines timeless character with modern convenience. The thoughtfully designed floor plan features soaring ceilings, oversized windows, hardwood floors, and all bedrooms conveniently situated on the upper level. The main living area provides exceptional flexibility with multiple gathering spaces, including a spacious living room, dedicated office or den area, breakfast nook, and an impressive formal dining room. From here, step out onto a large private deck ideal for outdoor dining, entertaining, grilling, or simply relaxing. The kitchen is equipped with abundant cabinetry, granite countertops, and stainless steel appliances. Upstairs, the generous primary suite offers a luxurious en-suite bath complete with dual vanities, a glass-enclosed shower, and a deep soaking tub. The bedroom also opens to a sun-filled private deck with attractive city views. A secondary bedroom features an adjoining bonus room that can easily serve as a walk-in closet, home office, study space, or playroom. An additional bedroom and full bath complete the upper level. Ample closet space and a dedicated utility room provide outstanding storage throughout. Located on a picturesque, tree-lined block of Mohawk Street surrounded by multi-million-dollar homes, this residence also benefits from permit parking. Enjoy easy access to the Brown and Red Line trains, the vibrant restaurants and shops of Old Town, and the nearby Clybourn Corridor-all just moments from your doorstep.

1445 N Mohawk Street Unit #2, Chicago
$260,000
1 Beds ⋅ 1 Baths ⋅ 12725009 MLS ⋅ NEW Status
Welcome home to this beautifully fully renovated 1-bedroom, 1-bathroom condo in the heart of Old Town. Thoughtfully updated from top to bottom, this move-in-ready residence features modern finishes, an open and functional layout, and stunning lake views that provide the perfect backdrop to everyday living. The stylish kitchen boasts contemporary cabinetry, sleek countertops, stainless steel appliances, and quality finishes that seamlessly flow into the bright living and dining area. The spacious bedroom offers ample closet space, while the beautifully renovated bathroom showcases timeless finishes and attention to detail throughout. Enjoy breathtaking views of Lake Michigan from the comfort of your home, along with abundant natural light pouring through oversized windows. Ideally situated in one of Chicago's most sought-after neighborhoods, you'll be just steps from the lakefront, Lincoln Park, the beach, top-rated restaurants, boutique shopping, grocery stores, nightlife, public transportation, and everything Old Town has to offer. Whether you're a first-time buyer, looking for an in-town residence, or seeking a turnkey investment opportunity, this exceptional condo combines modern style, an unbeatable location, and spectacular views in one incredible package.

1360 N Sandburg Terrace Unit #2104C, Chicago
$475,000
2 Beds ⋅ 2 Baths ⋅ 12723788 MLS ⋅ ACTIVE Status
Welcome to 1460 N. Sandburg Terrace, Unit 711, a beautifully renovated 2-bedroom, 2-bath southwest corner unit with abundant light and sweeping views of the city skyline. The open living spaces feel bright and inviting, with wide-plank flooring and oversized windows framing the gorgeous views. The updated kitchen features white cabinetry, quartz countertops, stainless steel appliances, a subway tile backsplash, and an expansive waterfall island with generous seating. A separate beverage nook adds another thoughtful touch, while the adjoining dining area and spacious living room create an easy flow for everyday living and entertaining. Both bedrooms are generously sized and offer excellent closet space, natural light, and room for a desk or additional furniture. Two updated full baths include clean, modern finishes, black fixtures, and beautifully tiled showers. Just off the living room, the private balcony offers a wonderful place to relax and take in the southwest views overlooking the neighborhood and skyline. Residents enjoy 24-hour door staff, a rooftop deck, bike storage, and access to Sandburg Village's seasonal outdoor pools, fitness center, and tennis/pickleball courts, with additional fees applying to select amenities. Heated garage parking may also be available for lease. Located in the heart of Old Town with easy access to the lakefront, dining, shopping, and public transportation, this move-in-ready condo offers modern finishes, comfortable room sizes, and an incredibly convenient location.

1460 N Sandburg Terrace Unit #711, Chicago
$1,495,000
4 Beds ⋅ 4 Baths ⋅ 12723758 MLS ⋅ ACTIVE Status
Beautifully Recently-Updated Old Town Single-Family Home | 4 Bedrooms | 3.1 Baths | Attached 2-Car Garage. Move right into this beautifully updated, sun-filled Old Town home offering oversized rooms, soaring ceilings, hardwood floors throughout, and an attached 2-car garage. Meticulously maintained with extensive recent improvements, including two newer HVAC systems (2024 & 2023), upgraded engineered rear deck with new stairs and concrete footings, a fully remodeled gas fireplace in Family room, renovated basement bath, refreshed four-season sunroom with new PTAC heating and cooling system, new flooring, insulation, and glass, plus a complete interior repaint, new lighting, and numerous mechanical and exterior improvements. The welcoming living room is filled with natural light and centered around a fireplace, while the formal dining room is perfect for entertaining with an adjoining Butler's pantry featuring stone countertops, a wine refrigerator, and beverage refrigerator. The heart of the home is the open kitchen with white cabinetry, quartz countertops, stainless steel appliances, a large island with breakfast seating, and a separate dining area overlooking the family room. The spacious family room, anchored by a corner fireplace, flows effortlessly into the stunning four-season sunroom and private deck, creating the perfect space for everyday living or entertaining year-round. Upstairs, skylights flood the home with natural light. The spacious primary suite offers its own private deck, a custom walk-in closet, and a spa-like bath with a double vanity, whirlpool tub, and separate shower. Additional 2 bedrooms share a beautifully appointed bath with stone finishes, a double vanity, a whirlpool tub, and a separate shower. A conveniently located laundry room completes the second level. The recently renovated walk-out English lower level offers incredible flexibility with a large recreation/media room, a fourth bedroom currently used as an office, a beautifully updated full bath, abundant storage, and direct access to the backyard and patio. Located on one of Old Town's most desirable streets, you'll enjoy being just steps from Lincoln Park, the Zoo, North Avenue Beach, and all of the restaurants, boutiques, coffee shops, and nightlife along Wells Street. Catherine Cook School is just one block away, with Immaculate Conception and Franklin Fine Arts Center nearby, plus easy access to LaSalle College Prep, Walter Payton College Prep, and Lincoln Park High School. An exceptional home that combines timeless character, extensive updates, and an unbeatable Old Town location.

1454 N Wieland Street, Chicago
$310,000
1 Beds ⋅ 1 Baths ⋅ 12723631 MLS ⋅ ACTIVE Status ⋅ Sandburg Village BLDG.
Perched on the 26th floor of Cummings House in the Gold Coast's Carl Sandburg Village, this freshly renovated 1-bedroom, 1-bath condo pairs sweeping skyline views with one of Chicago's most walkable addresses. Inside, wood laminate floors and crown molding run through a bright, open living and dining area set beneath a wall of windows - imagine watching the city light up from your sofa every evening. A 2026 renovation reset the kitchen and bath. The kitchen anchors the space with quartz countertops, solid wood cabinetry, and a peninsula with breakfast-bar seating, backed by a brand-new GE stainless steel appliance package - refrigerator, range, dishwasher, and microwave - with room left for a proper dining table. The generously scaled bedroom is tucked off its own hall, next to the updated bath finished in porcelain tile with an engineered marble countertop and a solid wood vanity. Cummings House is a full-service building with door staff, security, on-site management and engineering, elevators plus a service elevator, a bike room, party room, sundeck, and pool, surrounded by the community gardens and landscaped terraces that thread through Sandburg Village. Monthly assessments cover heat, water, doorman, TV/cable, internet, and Wi-Fi, plus exterior maintenance and trash removal - translation: most of the monthly bills are handled before you've unpacked. A first-floor storage unit is included, on-site laundry is steps away, and heated garage parking is available through the building. Out the front door on Schiller Street, you're a short walk to the Clark/Division Red Line and the Sedgwick Brown Line, with the 22, 36, 151, and 156 buses close by, Potash Markets and Jewel-Osco for groceries, and Old Town's Wells Street restaurants, Lincoln Park, and North Avenue Beach all within reach. The unit sits in the Ogden International School of the Americas (K-8) and Lincoln Park High School attendance areas - a perfect blend of skyline living and everyday neighborhood ease.

1360 N Sandburg Terrace Unit #2603C, Chicago
$342,000
1 Beds ⋅ 1 Baths ⋅ 12722561 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
$585,000
2 Beds ⋅ 2 Baths ⋅ 12687405 MLS ⋅ ACTIVE Status
Exceptional Old Town residence offering an impressive blend of space, natural light, and location. Situated a short stroll to the vibrant restaurants, boutiques, and entertainment along Wells Street, this expansive 2-bedroom, 2-bathroom home, recently updated, features an open floor plan and generously sized rooms throughout. Designed for both everyday living and entertaining, the thoughtfully configured floor plan features a huge main living area anchored by a cozy gas fireplace and framed by oversized south-facing windows that fill the home with sunshine throughout the day. The living room opens to the private west facing terrace, offering the perfect setting for morning coffee, evening relaxation, and grilling.The open-concept layout flows seamlessly into the dining area and updated kitchen, creating an inviting atmosphere for gatherings of any size. A huge west facing window provides another source of natural light. Numerous recent improvements, to the unit and the building, enhance the home's appeal.The kitchen showcases an abundance of cabinets in a neutral white, stone countertops,stainless appliances, a large island, and a full height tile backsplash. The spacious primary suite features a walk-in closet and a spa bath in marble and porcelain, with a dual-sink vanity, soaking tub, and separate shower. The second bedroom is generously proportioned and filled with natural light. There is a niche that fits a desk set up. Abundant storage can be found throughout the home. Additional features include new HVAC and laundry, a dedicated exterior parking space, a shared guest parking space. A beautiful home in Old Town, this home places you steps from some of Chicago's best dining, shopping, parks, and nightlife in one of Chicago's most desirable neighborhoods!

308 W Evergreen Avenue Unit #2, Chicago
$945,000
2 Beds ⋅ 2 Baths ⋅ 12719723 MLS ⋅ ACTIVE Status
Perfectly positioned in the heart of Old Town on iconic Wells Street, this sprawling corner 2-bedroom, 2-bath residence offers the ideal blend of luxury, space, and location. The highlight is an impressive 59' x 8' private west-facing terrace with a motorized retractable awning, where you can unwind with breathtaking sunsets while enjoying the serenity of the neighborhood-all just steps from Wells Street's renowned restaurants, charming cafes, and designer boutiques. Inside, this completely gut-renovated home showcases exceptional craftsmanship and thoughtful design throughout. The stunning kitchen features quartz countertops, stainless steel appliances, a stylish dry bar, and designer lighting. The expansive living room is anchored by a beautiful gas fireplace, creating a warm and inviting space for relaxing or entertaining. The grand primary suite offers a private retreat with a spacious sitting area, direct terrace access, a custom walk-in closet, and a luxurious en suite bath complete with a steam shower. Additional highlights include a brand-new LG stackable washer and dryer, abundant closet space, generous cabinetry, and exceptional storage throughout. A premium deeded heated indoor garage parking space is included. Enjoy unparalleled convenience with easy access to the Red, Brown, and Purple CTA lines, as well as multiple bus routes on LaSalle. Everyday essentials are just around the corner with Jewel-Osco, Fresh Market, and Aldi nearby, while some of Chicago's most beloved destinations-including Second City, the lakefront, and the Lincoln Park Farmers Market-are only moments from your front door. Boutique, 100 perc owner occupied, pet friendly, elevator building. Terrace has gas and water.

1414 N Wells Street Unit #409, Chicago
$1,450,000
3 Beds ⋅ 4 Baths ⋅ 12713927 MLS ⋅ ACTIVE 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
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.