Old Town Homes for Sale

Welcome to Old Town, a vibrant neighborhood located in the heart of Chicago, Illinois. Situated in Cook County, Old Town is a charming community known for its rich history, diverse culture, and lively atmosphere.

Old Town is a sought-after destination for homebuyers, offering a wide range of residential options to suit various preferences and budgets. Whether you're looking for a historic brownstone, a modern condo, or a spacious single-family home, you'll find an array of homes for sale in this neighborhood.

One of the appealing aspects of Old Town is its prime location. With its proximity to downtown Chicago, residents can enjoy easy access to the city's bustling business district, world-class dining, shopping, and entertainment options. Additionally, Old Town boasts excellent transportation links, making it convenient for commuters and those who love to explore the city.

Living in Old Town means immersing yourself in a vibrant community with a unique character. The neighborhood is known for its charming tree-lined streets, historic architecture, and a thriving arts scene. Residents can explore a variety of local galleries, theaters, and music venues, showcasing the area's creative spirit.

When it comes to amenities, Old Town has plenty to offer. From trendy boutiques and specialty shops to cozy cafes and renowned restaurants, there's something for everyone. The neighborhood also boasts beautiful parks and green spaces, providing opportunities for outdoor recreation and relaxation.

Whether you're a first-time homebuyer or looking to upgrade your current living situation, Old Town is a fantastic place to call home. With its rich history, vibrant culture, and diverse real estate options, this neighborhood offers a unique and fulfilling living experience. Explore the homes for sale in Old Town and discover your perfect place in this thriving community.

Newest Old Town Homes for Sale

$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

$899,000

3 Beds ⋅ 3 Baths ⋅ 12748295 MLS ⋅ ACTIVE Status

Located in Charming Old Town, just a 1/2 Block from the Brown Line Stop, this 3 Bedroom, 2.5 Bathroom Red Brick Home offers a Level Yard with a 25' x 30' Private Backyard! Sure to impress is the Open Floor Plan with Tall Ceilings, Exposed Brick and Brazilian Cherry Hardwood Floors that flow from the Living Room into the Dining Room and Kitchen. Create Culinary Delights in the Gourmet Kitchen that is equipped with Upgraded Appliances including a 36" Viking 6 Burner Stove/Oven and Hood, Jenn-Air French Door Fridge, Bosch Dishwasher, Custom Built 42" Cabinets, a Large Island with Seating for 4 and a Walk-in Pantry. The Upper Floor is Home to the 3 Bedrooms including the Primary Bedroom with Custom Elfa Closet Organizers and an EnSuite Bathroom with Walk-In Shower and a 5' Whirlpool Bathtub. The Partially Finished Basement with Epoxy Flooring awaits your Finishing Touches to transform it into the Ultimate Entertaining Space! Additional Home Features include: Perma-Seal Basement System (annual $99 service call paid through 10/02/2027), Levolor Top/Bottom Blinds, Remote Controlled Awning Blinds on 2nd Floor Bath and Rear Main Level Door, Two High Efficiency Dual Zone Central Heat and Central Air, New Roof (2010), Tankless Water Heater, Custom Landscaped Rear Yard with Custom Paver Stones and 3 Deeded Indoor Parking Spaces next door at Royalton Towers (garage is in/out on Sedgwick side and also has a pedestrian entry on N. Orleans) at 1444 N. Orleans Street (spaces G26, G61 and G62 - The Sedgwick Garage Condo Association provides the insurance and maintenance with a monthly association cost of $257.99 for all three spaces). This Prime Location is Moments to: Lincoln Park Venues, Second City, Famous Wells Street Restaurant and Shopping District, Public Transportation, Lincoln Park, Whole Foods, Target, Trader Joes, Nightlife and More.

1436 N Orleans Street, Chicago

$1,445,500

4 Beds ⋅ 4 Baths ⋅ 12741980 MLS ⋅ PRICE CHANGE Status

JUST COMPLETED - RECENTLY UPDATED OLD TOWN SINGLE-FAMILY HOME | 4 BEDROOMS | 3.1 BATHS | ATTACHED 2-CAR GARAGE A newly updated four-season sunroom with year-round heating and cooling opens to the private deck and backyard, creating exceptional indoor-outdoor living. Completely rehabbed in 2019 and recently updated by the current owner, including the exterior and interior. This sun-filled Old Town home offers large rooms, soaring ceilings, oversized windows, hardwood floors throughout, fresh paint, and an extra-long attached 2-car garage. The bright living room features a vintage fireplace & oversized windows overlooking a tree-lined street, while the formal dining room includes an adjoining butler's pantry with stone countertops, a wine refrigerator, and a beverage refrigerator. The open kitchen features white cabinetry, quartz countertops, stainless steel appliances, a large island with seating, and a separate dining area. The spacious family room, with soaring ceilings and a corner fireplace, flows directly into the updated four-season sunroom, updated deck, and backyard-perfect for everyday living and entertaining. Upstairs, skylights provide abundant natural light. The primary suite features a private deck, custom walk-in closet, and spa-like bath with double vanity, whirlpool tub, and separate shower. Two additional bedrooms share a beautifully appointed bath, and a laundry room completes the level. The completely renovated walk-out lower level offers a large recreation/media room, a fourth bedroom currently used as an office, an updated full bath, abundant storage, and direct backyard access. A beautifully updated, move-in-ready home offering exceptional space, indoor-outdoor living, and an unbeatable Old Town location. 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

$5,200,000

7 Beds ⋅ 6 Baths ⋅ 11755660 MLS ⋅ ACTIVE Status

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.