Old Town Real Estate

Old Town Real Estate

Old Town, located in the heart of Chicago, Illinois, is a vibrant and historic neighborhood that offers a unique blend of old-world charm and modern amenities. Situated in Cook County, Old Town is known for its rich history, diverse culture, and lively atmosphere.

With its tree-lined streets, picturesque row houses, and beautiful architecture, Old Town exudes a timeless appeal. The neighborhood is home to a variety of housing options, ranging from historic Victorian-era homes to contemporary condominiums, making it an ideal place for people of all ages and lifestyles.

Old Town boasts a thriving arts and entertainment scene, with numerous theaters, art galleries, and music venues. The famous Second City comedy club, where many renowned comedians got their start, is also located in the neighborhood, offering endless laughter and entertainment.

In addition to its cultural offerings, Old Town is known for its eclectic mix of boutiques, specialty shops, and gourmet restaurants. Residents and visitors can explore the neighborhood's unique shops, indulge in delicious cuisine, and savor the vibrant nightlife.

With its prime location, Old Town provides easy access to the rest of Chicago, including downtown and the lakefront. The neighborhood is well-served by public transportation, making it convenient for commuters and those who love to explore the city.

Whether you're looking for a charming historic home, a trendy loft, or a lively and diverse community, Old Town has it all. Experience the best of Chicago living in this iconic neighborhood that seamlessly blends the past with the present.

Newest Listings in Old Town

$650,000
3 Beds ⋅ 2 Baths ⋅ 12755445 MLS ⋅ NEW 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
$425,000
2 Beds ⋅ 2 Baths ⋅ 12754862 MLS ⋅ NEW Status
Unobstructed northern skyline and partial lake views highlight this beautifully updated two bedroom condo in the heart of Old Town. Filled with natural light, the spacious open floor plan offers plenty of room for living and dining, while the split-bedroom layout provides added privacy for guests, roommates, or a home office. The kitchen opens to the living space and features stainless steel appliances, a new backsplash, and floor to ceiling windows. Step outside to the private balcony with new tile and plenty of room to grill, relax, and enjoy the views. The spacious primary suite features a large walk in closet and en-suite bath. Recent updates include new flooring, fresh paint, a new dishwasher, new washer and dryer, updated lighting, and balcony tile. HVAC replaced in 2018. One heated garage space is included. This full amenity building offers 24 hour door staff, a fitness center, rooftop sundeck, renovated fifth floor terrace, dog run, and on site management. Enjoy easy access to Old Town restaurants, shopping, coffee shops, fitness studios, the lakefront, Lincoln Park, and public transportation. Separate storage locker included. Monthly HOA fee includes cable and internet.

230 W Division Street Unit #1107, Chicago
$485,000
2 Beds ⋅ 1 Baths ⋅ 12754756 MLS ⋅ NEW Status
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
$459,000
2 Beds ⋅ 2 Baths ⋅ 12754467 MLS ⋅ NEW Status ⋅ Old Town Village East BLDG.
First 6 Months of HOA fees credited to the buyer at closing! Located in the heart of Old Town, this second-floor 2-bedroom, 2-bathroom condo sits back off a quiet, tree-lined street with a peaceful, park-like setting. Inside, hand-scraped engineered wood floors (installed 2021) run throughout, and large windows bring in tons of natural light along with treetop views. You'll find a gas fireplace, in-unit laundry, a private balcony, and ample storage. The kitchen is finished with stainless steel appliances, including a new refrigerator (2025), microwave (2026), and dishwasher (2021), granite countertops, and a breakfast bar. Both bedrooms are generously sized, and the primary suite includes his-and-her closets and an en-suite bath with dual sinks and granite counters. AC replaced in 2021, as well as the water heater 2021. The condo comes with an assigned, gated parking space, the most desirable spot in the building and closest to the entry, with easy access off the cobblestone drive, plus plenty of guest parking. The monthly assessment covers gigabit internet (Zentro Wireless), water, trash, landscaping, and snow removal. Set right in the center of Old Town, you're blocks from the bars and restaurants on Wells Street, with direct access from the rear entry, plus Seward Park, Lincoln Park and the Lincoln Park Zoo, and the lakefront. Public transportation is easy, with the Red, Purple, and Brown Lines and the #37 bus to the Loop right outside, and three grocery stores, Starbucks, and shopping are all close by. The building is legally designated non-smoking under the City of Chicago's Clean Air Ordinance.

1225 N Orleans Street Unit #602, Chicago
$400,000
2 Beds ⋅ 2 Baths ⋅ 12753518 MLS ⋅ NEW Status ⋅ Eliot House BLDG.
Welcome to The Eliot House at 1255 N. Sandburg Terrace, where modern city living meets casual neighborhood charm. This bright and airy 14th-floor corner residence offers approximately 1,100 square feet of thoughtfully designed living space, featuring two bedrooms and two bathrooms. This unit was fully rehabbed in 2019 thruout and has been lightly lived in as an into town since then. Large windows fill the residence with natural light and showcase sweeping north and west views of the Gold Coast, while a private balcony provides the perfect place to relax and enjoy stunning city views. The well-appointed kitchen includes a range, dishwasher, microwave, and refrigerator. Both generously sized bedrooms can accommodate king-size beds and offer large closets with ample storage. The Eliot House offers an impressive array of amenities, including a doorman, elevator, service elevator, rooftop deck, tennis court, below-ground pool, bike room, common storage, and on-site laundry facilities. Garage parking is available for lease. The building is pet-friendly, subject to restrictions, and has recently completed building updates. Ideally located near vibrant Wells Street, the property is just steps from exceptional shopping, dining, entertainment, and neighborhood conveniences. The unit is being sold fully furnished for no cost to buyer. If that's an issue it can be removed.

1255 N Sandburg Terrace Unit #1411, Chicago
$349,000
1 Beds ⋅ 1 Baths ⋅ 12748722 MLS ⋅ NEW Status
Charm and style define this lovely one-bedroom at 1455 N Sandburg. Professionally designed with classic herringbone hardwood floors, a newly updated kitchen with stone counters, wine storage, a center island with a custom butcher block top, and adjacent dining area. The ample living room features custom-built bookcases and storage, enhanced with traditional library lights, creating a rich ambience for new owner. The spacious bedroom features extensive custom details: newly designed built-in storage with custom sconces and textured wall covering to add richness to the overall design. The eastern-facing balcony brings nature inside with sunlight for flowers and plants and plenty of space for a cafe table and chairs. 1455 Sandburg is central to all transportation: buses, redline CTA, and on-site leased parking available.

1455 N Sandburg Terrace Unit #508, Chicago
$260,000
1 Beds ⋅ 1 Baths ⋅ 12754021 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
$480,000
2 Beds ⋅ 2 Baths ⋅ 12753995 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
$319,900
1 Beds ⋅ 1 Baths ⋅ 12753898 MLS ⋅ NEW Status ⋅ 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
$295,000
1 Beds ⋅ 1 Baths ⋅ 12736182 MLS ⋅ NEW Status
Ideally situated in the heart of Sandburg Village, this 1-bedroom residence at Cummings House offers comfortable city living with a private balcony and beautiful skyline and lake views. The northeast-facing home is filled with natural light and features hardwood floors throughout, an open-concept living area, and a kitchen with abundant cabinetry and a convenient breakfast bar with seating. The bedroom offers beautiful views, while the marble-tiled bathroom and fresh paint throughout give the home a clean, refreshed feel. Residents of Cummings House enjoy an impressive collection of full-service amenities, including an outdoor pool with cabanas, private tennis and pickleball courts, a rooftop deck with panoramic city views, doorman, 24-hour on-call maintenance, on-site garage parking, bike storage, laundry facilities, and a dedicated package and receiving room. Set near the Gold Coast, Old Town, and Lincoln Park, this location puts some of Chicago's best dining, shopping, entertainment, and outdoor recreation within easy reach. North Avenue Beach and the lakefront paths are nearby. Enjoy restaurants such as Small Cheval, Happy Camper, and the 3 Arts Club along with the Chicago History Museum, Second City, and Zanies for entertainment. Your neighborhood grocery options include Fresh Market, Aldi, and Potash Market. Convenient access to the Red and Brown Lines, as well as Clark and LaSalle bus routes, makes getting around the city effortless. Enjoy the best of city living from this beautiful home in one of Chicago's most established residential communities.

1360 N Sandburg Terrace Unit #1106C, Chicago
$1,499,000
4 Beds ⋅ 4 Baths ⋅ 12753212 MLS ⋅ NEW Status
Exceptional luxury living, completely RENOVATED on an unusually deep 25' x 141' lot with a gated private alley and beautiful southern exposure, filling the home with abundant natural light. Extensively and thoughtfully renovated in 2022 and 2023 by Olson Studios, LLC, this sophisticated residence blends timeless design with beautifully curated, high-end finishes. A lush backyard with established perennial gardens creates a private outdoor retreat in the heart of the city. The Exquisite reimagined main level features refinished hardwood floors in a white-oak finish, a gracious living room with a bay window, and a separate dining room enhanced by a widened 4-foot opening to the kitchen, creating an effortless flow for everyday living and entertaining. Completely renovated in 2023, the expansive custom chef's kitchen was enlarged and showcases full-height custom white cabinetry with soft-close doors and drawers, under-cabinet lighting, quartz countertops, and an impressive oversized island. A premium appliance package includes a built-in Sub-Zero refrigerator, Wolf 30" four-burner gas range with 36" built-in hood, Sharp 24" microwave drawer, and Bosch built-in dishwasher. The inviting family room is beautifully appointed with custom built-in bookcases, transom windows, and a wood-burning fireplace with a gas starter, complemented by a Frame TV with concealed A/V components for a seamless, sophisticated finish. Elegant oak railings lead to the second level, complemented by white-oak-finished stairs and upper hallway. The upper level offers three generously proportioned bedrooms. The front bedroom features a dramatic vaulted ceiling, bay window, and spacious walk-in closet, while the second bedroom is exceptionally large with generous closet space. The luxurious primary suite is a serene private retreat, featuring vaulted ceilings and French doors that open to a private balcony. A gorgeous new spa-inspired primary bath completes the suite with an expansive walk-in shower and beautifully appointed finishes. The sun-filled lower level offers exceptional additional living space with high ceilings, a spacious family/recreation room, an open fourth bedroom or flexible guest space, full bath, abundant closets, and an oversized storage room-providing incredible versatility for everyday living, a home office, fitness area, or additional entertaining space. Extensive Renovations & Improvements: July 2022 - Primary and hall bathrooms completely renovated. June 2023 - Kitchen and powder room completely renovated, hardwood floors refinished, new interior doors installed, and fireplace surround updated. Additional upgrades include Andersen windows, a comprehensive security system, and custom closet systems throughout. The home is also prewired for an integrated sound system in the family room, living room, primary suite, and primary bath. The HOA ($475 quarterly)includes snow removal, landscape care, private waste collection, and alley maintenance. Just moments from the lakefront, Lincoln Park and Zoo, North Avenue Beach, and the acclaimed restaurants, cafes, galleries, boutiques, and nightlife of Wells Street. The home also offers convenient access to public transportation and many of Chicago's premier schools, including LaSalle Language, British International, Catherine Cook, Latin School, Walter Payton, and Franklin. A rare Old Town offering tucked between the Gold Coast and Lincoln Park, combining exceptional space, natural light, sophisticated style, and a coveted walk-to-everything location.

331 W Evergreen Avenue, Chicago
$319,000
1 Beds ⋅ 1 Baths ⋅ 12744325 MLS ⋅ ACTIVE Status
Enjoy lake views and a private balcony from this east-facing one-bedroom home in Sandburg Village's James House! The combined living and dining area opens to a spacious balcony, offering room to relax and take in the views. The kitchen features white cabinetry, granite countertops, a tile backsplash, and a breakfast bar for casual dining. Lake views continue into the bedroom, where closet organizers provide practical storage. In-unit laundry adds everyday convenience. Ideally located near Old Town, the Gold Coast, and Lincoln Park, with dining, shopping, the lakefront, and public transportation nearby.

1560 N Sandburg Terrace Unit #1506, 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.