Browse All Lincoln Square IL Historical Properties for Sale

6 Beds ⋅ 3 Baths ⋅ 12686346 MLS ⋅ CONTINGENT Status

Exceptional opportunity to own one of Lincoln Square's most charming and architecturally significant greystones on one of the neighborhood's most picturesque, tree lined blocks. Beautifully maintained and thoughtfully updated over the years, this timeless two flat with an additional garden apartment showcases true pride of ownership while offering remarkable flexibility for investors, owner occupants, or those seeking the perfect house hacking opportunity in one of Chicago's most coveted neighborhoods. The first floor residence offers two spacious bedrooms and a beautifully renovated bathroom, complemented by an expansive floor plan featuring a gracious living room, sun filled den, formal dining room, and an updated eat in kitchen. Rich original oak hardwood floors, intricate millwork, and a stunning built in hutch have been meticulously preserved, highlighting the home's historic character. The renovated kitchen opens to a private rear porch, an ideal setting for morning coffee, al fresco dining, or entertaining guests. Generous storage can be found throughout the home. The second floor residence features three bedrooms, one updated bathroom, and a dedicated office just off the kitchen, perfect for today's work from home lifestyle. The spacious living room is flooded with beautiful southern sunlight, while the oversized formal dining room provides an inviting space for family gatherings and entertaining. The bright and welcoming garden apartment offers a well designed one bedroom, one bathroom layout with abundant natural light, creating an attractive option for additional rental income, extended family, or guest accommodations. The building has been exceptionally cared for, reflecting decades of thoughtful stewardship and meticulous maintenance. Additional storage and a shared laundry area are conveniently located in the basement. Outside, the professionally designed Zen inspired rear garden creates a peaceful urban retreat. The full masonry three car garage is crowned by an impressive finished rooftop deck, an extraordinary outdoor living space rarely found in the city. The location is simply unmatched. Just one block from the vibrant heart of Lincoln Square, you'll enjoy effortless access to beloved neighborhood restaurants, cozy cafes, boutique shopping, neighborhood taverns, parks, the CTA Brown Line, the Lincoln Square Farmers Market, the Chicago Riverwalk trail system and the year round concerts, festivals, and community events that make this one of Chicago's most treasured neighborhoods. Whether you're looking for a trophy investment, a multi generational home, or an owner occupied property with substantial income potential, this exceptional greystone offers timeless architecture, impeccable condition, enduring value, and outstanding future upside in one of Chicago's strongest and most sought after residential markets.

2230 W Leland Avenue, Chicago

$1,050,000

12675568 MLS ⋅ CONTINGENT Status

*** Multiple Offers Received - Best and Finals Due Monday at 12pm *** Exceptional mixed-use 4 unit investment opportunity in the heart of Lincoln Square! Situated on one of Chicago's most desirable commercial corridors, this fully occupied corner property features two oversized 3-bedroom apartments and two highly visible retail storefronts, creating a rare blend of stable income, future upside, and prime location. The retail component includes a prominent Lincoln Avenue storefront with a full basement and a long-term lease of $2550 escalating each year by $50 extending through 2028, along with a Western Avenue storefront occupied by a long-term tenant who is prepared to execute a new three-year lease. Above the retail spaces are two spacious residential units: a 3-bedroom, 1.5-bath apartment on the second floor renting for $2600 with a lease through 06/2027 and a 3-bedroom, 1-bath apartment on the third floor renting for $2400 with a lease until 07/2026. Both apartments feature central air conditioning, in-unit laundry, hardwood floors, and beautiful original woodwork that reflects the character and charm Lincoln Square is known for. The property also offers the potential to create a rooftop deck above the Western Avenue retail space. Currently zoned B3-3, the property's lot and exceptional location may present future redevelopment potential, including a larger mixed-use or transit-oriented development (buyer to verify). The building is well-maintained, fully occupied, and generates immediate income, while the upcoming vacancy of the third-floor apartment in July 2026 provides a unique opportunity for an owner-occupant, value-add investor, or buyer looking to renovate and bring rents closer to market levels. Located within the highly sought-after Waters Elementary School attendance boundary, this property offers an added layer of appeal for future owner-occupants and tenants alike. Residents and tenants enjoy immediate access to some of Chicago's most beloved restaurants, cafes, shops, and neighborhood destinations. Gene's Sausage Shop & Delicatessen, Garcia's, Barba Yianni, Willow Cafe, Potbelly, Lincoln Square Athletic Club, and OrangeTheory are all just steps away. Commuters will appreciate easy access to the Western Brown Line station, multiple CTA bus routes, and the convenience of living in one of Chicago's most walkable and sought-after neighborhoods. Whether you're seeking a strong long-term investment, an owner-occupied opportunity, or a strategic redevelopment play, 4754 N. Lincoln Avenue offers an outstanding combination of location, income, future potential, and an unbeatable Lincoln Square location. Listing agent is related to the owner and has financial interest in the property.

4754 N Lincoln Avenue, Chicago

$950,000

6 Beds ⋅ 3 Baths ⋅ 12664353 MLS ⋅ CONTINGENT Status

Incredible updated brick multi-unit on an oversized 30x160 lot, nestled on a quiet, tree-lined street in a prime Lincoln Square location. Spacious units are flooded with natural light and feature hardwood floors throughout - beautifully updated while maintaining their classic vintage charm. Enjoy outstanding outdoor living with private back decks and an enormous backyard, plus a garden in-law unit that adds incredible value and versatility. Conveniently located near two Brown Line stops, and all the beloved restaurants, shops, and parks that make Lincoln Square one of Chicago's most sought-after neighborhoods. An exceptional investment opportunity - do not miss this one!

2541 W Argyle Street, Chicago

$849,000

10 Beds ⋅ 4 Baths ⋅ 12544393 MLS ⋅ CONTINGENT Status

Two buildings. 4 units total plus basement. Main building is 3,000 square feet plus basement and has both units occupied. 3 bed, 1 bath in each unit. Full basement (in law). Back building has 2 units, 2,360 square feet and is completely vacant. Condition unknown. In need of major rehab.

2527 W Argyle Street, Chicago

$4,950,000

12255159 MLS ⋅ ACTIVE Status

Exclusively engaged to solicit offers to purchase the fee simple interest of the subject property located at 4810-4820 North Western Ave., Chicago, IL 60625 (the "Property"). This is an urban office/retail building located in Chicago's dense and affluent Lincoln Square neighborhood. The subject property is zoned B3-2 and situated in a mixed commercial and residential city setting. Featuring a vacant two-story building 18,000 SF GLA, and 8,276 SF lot. *** Property boasts 90.03' of frontage on Western Avenue with the traffic counts exceeding 34,500 VPD! The latest neighborhood investments: such as new construction, condos, rentals, restaurants, nightlife, and supermarkets have steadily brought in new homeowners and tenants to this thrilling neighborhood of Chicago. The subject property presents the unique development/re-development opportunity to acquire a stand-alone building in the Lincon Square district.

4820 N Western 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.

Lincoln Square Historical Real Estate

Our website features the best real estate search for historical properties available in Lincoln Square 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!