West Side Homes with Greystone Style

Welcome to the enchanting West Side of Chicago, a vibrant neighborhood that beautifully marries history with modern living. Nestled within Cook County, this area is renowned for its rich cultural tapestry and architectural charm, making it a highly sought-after destination for homebuyers looking for character and community.

One of the standout features of the West Side is its stunning Greystone homes. These iconic structures, with their distinctive limestone facades and intricate detailing, are a testament to the craftsmanship of the late 19th and early 20th centuries. The Greystone style captures the essence of Chicago's architectural heritage, offering a unique blend of elegance and warmth. Many of these homes boast spacious interiors, high ceilings, and original woodwork, providing a perfect canvas for both modern updates and classic restorations.

Living in the West Side means embracing a dynamic lifestyle. Residents enjoy easy access to a variety of parks, local eateries, and cultural landmarks, creating a vibrant community atmosphere. The West Side is also well-connected to downtown Chicago, making it ideal for commuters who want to enjoy the hustle and bustle of the city while retreating to the tranquility of their neighborhood at the end of the day.

Whether you’re drawn to the historic charm of Greystone homes or the lively spirit of the community, the West Side offers an inviting place to call home. Discover the perfect blend of history, culture, and modern convenience in this remarkable Chicago neighborhood!

Newest West Side Homes with Greystone Style

$458,900

9 Beds ⋅ 3 Baths ⋅ 12799656 MLS ⋅ NEW Status

Welcome to 4018 W Polk St! This beautifully rehabbed property offers an impressive 9 bedrooms, 3 bathrooms, and a finished basement. Recently updated throughout, this spacious home combines modern comfort with a versatile layout, offering plenty of room for everyday living, entertaining, and working from home. The finished basement provides additional space and flexibility. With its extensive renovations and generous living space, this move-in-ready property is a fantastic opportunity. Schedule your private showing today!

4018 W Polk Street, Chicago

$499,959

9 Beds ⋅ 3 Baths ⋅ 12797063 MLS ⋅ NEW Status

Investor's Dream: Fully Remodeled Multi-Family Gem This unique, high-yield investment opportunity is a true "cash cow" that checks every box for the savvy investor or the smart home buyer. Recently remodeled and move-in ready, this property features an efficient layout designed for consistent cash flow and high tenant demand. Property Highlights: * Unit 1: Spacious 5-bedroom, 2-bathroom layout located on the ground floor. * Unit 2: Well-appointed 4-bedroom, 1-bathroom residence on the second floor. * Upgrades: Recent renovations ensure low maintenance and immediate occupancy. * Prime Location: Situated in a highly desirable area with seamless access to public transportation, major commuter rail lines, and local shopping hubs. This property offers an exceptional blend of modern updates and strategic location, making it the perfect addition to any investment portfolio. Don't miss out on this rare chance to secure a turnkey asset in a thriving market-schedule your private tour today!

2124 S Trumbull Avenue, Chicago

$360,000

7 Beds ⋅ 2 Baths ⋅ 12796589 MLS ⋅ ACTIVE Status

ATTENTION INVESTORS! Beautiful Greystone building. Don't miss out on this excellent opportunity. This property is currently tenant-occupied on 2nd floor and features a first-floor unit with 3 bedrooms and a second-floor unit with 4 bedrooms, each with a full bathroom.

3903 W Monroe Street, Chicago

$537,900

6 Beds ⋅ 3 Baths ⋅ 12793905 MLS ⋅ ACTIVE Status

We have an excellent opportunity for you to own an updated 3flat Greystone featuring 6 bedrooms and 3 full bathrooms in the West Garfield Area. All units are currently vacant and have been recently painted and refreshed, providing a clean palette for investors or owner occupants. Each unit features separate utilities, washer and dryer hookups and updated finishes throughout, including flooring, cabinetry, lighting and more. The main level unit has a separate living room and dining room, 2 bedrooms and 1 full bathroom. The second floor unit has a similar layout with 3 bedrooms and 1 full bathroom. The garden unit includes 1 bedroom and 1 full bathroom. Additional property features include a gated entry, exterior rear porch, fenced backyard with 2 exterior parking spaces and basement storage space. With 3 separate units, refreshed interiors and immediate availability for a new owner, this property presents an excellent opportunity for investors seeking rental income or buyers looking to expand their real estate portfolio. Schedule your showing today!

3923 W Polk Street, Chicago

$499,900

10 Beds ⋅ 4 Baths ⋅ 12772530 MLS ⋅ ACTIVE Status

UNIQUE INVESTMENT OPPORTUNITY for both SEASONED INVESTORS and SAVVY HOMEOWNERS looking to LIVE FOR FREE while the other unit pays the mortgage. EXCEPTIONAL OVERSIZED 2-UNIT BUILDING, a rare find in today's market! Recently RENOVATED. GENEROUS Living Spaces in both units. MODERN AMENITIES. Each unit features 5 Bedrooms + 2 Full Baths + Beautiful Kitchen area. This property promises STRONG CASH FLOW! DON'T MISS OUT the opportunity!!! Schedule a showing TODAY and secure your future in Real Estate!

631 N Monticello Avenue, Chicago

$325,000

5 Beds ⋅ 2 Baths ⋅ 12776067 MLS ⋅ ACTIVE Status

**Great Investment Opportunity Just Minutes from Downtown Chicago!** Discover the potential of this spacious **Brick Greystone two-unit property**, ideal for investors and owner-occupants looking to build equity or expand their real estate portfolio! This beautiful Chicago Greystone offers generous living spaces and extra-large bedrooms on both levels. The **second-floor unit features 3 bedrooms and 1 bathroom**, while the **first-floor unit offers 2 bedrooms and 1 bathroom with a duplex layout connecting to the unfinished basement**. Bring your vision and creativity to the basement, offering exciting possibilities for future improvements and customization, subject to applicable building codes and approvals. **Both units are currently vacant**, giving the next owner the flexibility to move right in, establish rental income, or make improvements to maximize the property's potential. The spacious, open backyard offers additional possibilities for a newly constructed garage, concrete parking slab, or outdoor entertainment space. Conveniently located with access to downtown Chicago, major expressways, shopping, dining, and public transportation. Whether you're a seasoned investor looking to expand your portfolio or an owner-occupant interested in house hacking, this **Chicago Greystone** offers space, character, flexibility, and outstanding value-add potential. **Bring your ideas, explore the possibilities, and make this investment your own!**

3318 W Flournoy Street, Chicago

$350,000

5 Beds ⋅ 2 Baths ⋅ 12778343 MLS ⋅ ACTIVE Status

Greystone architecture and original details give this early 1900s two-flat a character that's distinctly Chicago. Projecting bays, tall windows, hardwood floors and original millwork bring warmth and architectural interest throughout two well laid out residences. The first-floor unit offers 2 bedrooms and 1 bath with separate living and dining rooms, an updated kitchen with granite countertops and stainless steel appliances, in-unit laundry hookup, and a primary bedroom with walk-in closet. Upstairs, the 3-bedroom, 1-bath residence features an expansive living and dining space, updated kitchen and bath, hardwood floors, and in-unit laundry hookup. A full unfinished basement offers additional storage, two points of egress, and utility. The rear of the property features generous outdoor space and parking for up to four vehicles. With two distinct residences, the property lends itself equally well to owner-occupancy or a fully income-producing investment. Located in West Garfield Park along historic Jackson Boulevard, with convenient access to CTA bus service, nearby Blue and Green Line connections, I-290, Garfield Park, and downtown Chicago.

4319 W Jackson Boulevard, Chicago

$549,900

11 Beds ⋅ 5 Baths ⋅ 12769474 MLS ⋅ ACTIVE Status

Exceptional House-Hack Opportunity in North Lawndale 3-Unit Building | 11 Bedrooms | 5 Bathrooms Discover an outstanding opportunity to own a 3-unit multifamily property at 1239 S. Avers Ave in Chicago's North Lawndale neighborhood. Featuring 11 bedrooms and 5 bathrooms, this generously sized building offers a versatile setup for both owner-occupants and investors. Perfect for a house-hacking strategy, an owner-occupant can live in one unit while renting the remaining units to generate rental income and help offset monthly housing expenses. For investors, the property offers the potential to maximize rental income while building long-term equity. Each unit provides spacious living areas, multiple bedrooms, functional floor plans, and abundant natural light, creating comfortable spaces for tenants and larger households alike. Property Highlights 3 legal residential units 11 total bedrooms 5 total bathrooms Spacious and functional floor plans Abundant natural light Strong potential for rental income Excellent opportunity for owner-occupants and house hackers Attractive long-term investment potential Convenient access to public transportation Close to schools, parks, shopping, and neighborhood amenities Easy access to major expressways and downtown Chicago Located in North Lawndale, the property is situated in an area that has experienced ongoing investment and redevelopment. Its location, size, and three-unit configuration provide flexibility for a variety of ownership and investment strategies. Whether you're looking to reduce your housing expenses through rental income, expand your real-estate portfolio, or establish a long-term income-producing asset, this property offers an opportunity worth exploring. Schedule your private showing today and discover the possibilities this versatile multifamily property has to offer.

1239 S Avers Avenue, Chicago

$649,900

6 Beds ⋅ 3 Baths ⋅ 12759675 MLS ⋅ ACTIVE Status

GORGEOUS CLASSIC CHICAGO GREYSTONE 2-FLAT - BOTH RESIDENTIAL UNITS COMPLETELY REHABBED IN 2025! Both units have been beautifully renovated, while many major systems and exterior components have also been replaced or upgraded. Major 2025-2026 improvements include a NEW ROOF, WINDOWS, FURNACES, CENTRAL A/C, WATER HEATER, ELECTRICAL, PLUMBING, SIDING/EXTERIOR, GUTTERS & DOWNSPOUTS, SUMP PUMP, SEWER LINE, and BASEMENT/FOUNDATION WATERPROOFING. New drywall was installed throughout both units. Each unit features new kitchens with cabinets, countertops and appliances, remodeled bathrooms, updated flooring, fresh paint, new lighting, fixtures, doors and trim. New refrigerators, ranges, dishwashers, washers and dryers are included, along with smart thermostats and security cameras. The property also offers a rear deck, extra-deep backyard and parking, plus an unfinished basement with front and rear access, good ceiling height and separate heating. The basement provides excellent storage and flexible-use space, with potential for a future garden unit, subject to City of Chicago zoning, building-code and permitting requirements. Ideally located in East Garfield Park, just minutes from the United Center, Green Line, I-290, Garfield Park Conservatory, parks and Downtown Chicago. A wonderful opportunity to own a classic Chicago Greystone with two beautifully rehabbed residential units, major updates already completed, a spacious lot, and an unfinished basement with future potential. A great choice for an owner-occupant or investor!

3234 W Fulton Boulevard, Chicago

$400,000

6 Beds ⋅ 3 Baths ⋅ 12757989 MLS ⋅ ACTIVE Status

ATTENTION HOME BUYERS LOOKING FOR A 2-unit Greystone in a well sought after area that's located 12 minutes from the Medical District and 10 minutes from the United Center. This property has a one-bedroom apartment in the basement for additional income. It's perfect for a family looking to have their own individual apartment or an owner looking to live in one unit and rent the other two units and live mortgage free. All units have a washer/dryer, central air, and heat. This building is a great investment for the savvy investor or owner occupant as all utilities are paid by each tenant except the water bill. Great opportunity! BEING SOLD AS-IS!!!!

1242 S Millard Avenue, Chicago

$299,000

8 Beds ⋅ 2 Baths ⋅ 12719297 MLS ⋅ ACTIVE Status

3900 W Flournoy Street, Chicago

$419,000

11 Beds ⋅ 6 Baths ⋅ 12712792 MLS ⋅ ACTIVE Status

Turn key investment opportunity in the form of a handsome Greystone with 4 rentable units. Legal 3 unit + bonus unit in basement. 10 total bedrooms and 6 total bathroom. 2 of 4 units are occupied. In unit washer / dryer, individual water heater and tenant paid utilities. Potential for owner occupy "house hack" to live in the building or use as pure investment and realize the potential $6500/mo gross rent. Large fenced backyard and parking pad.

1330 S Lawndale 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.

West Side Homes with Greystone Style

Newest West Side Homes with Greystone Style

How much is your home worth?

How much is your home worth?