West Side Homes with Greystone Style

Welcome to the vibrant West Side of Chicago, a neighborhood that beautifully blends rich history with modern urban living. Nestled within Cook County, this area is renowned for its diverse culture, dynamic community, and stunning architecture, making it an ideal place for families and professionals alike.

One of the most charming aspects of the West Side is its iconic greystone homes. These elegant structures, characterized by their distinctive limestone facades, are a hallmark of Chicago's architectural heritage. Built primarily in the late 19th and early 20th centuries, greystones exude a timeless appeal that captivates residents and visitors alike. With their intricate detailing, spacious layouts, and inviting front porches, these homes offer a unique blend of classic charm and modern amenities.

Living in the West Side means being part of a thriving community. You'll find an array of local shops, cafes, and restaurants that reflect the neighborhood's rich cultural tapestry. Parks and green spaces provide ample opportunities for outdoor recreation, while nearby public transportation makes commuting to downtown Chicago a breeze.

Whether you’re drawn to the historic allure of greystone homes or the vibrant community atmosphere, the West Side of Chicago offers a unique lifestyle that celebrates both the past and the present. It’s a neighborhood where you can truly feel at home, surrounded by friendly neighbors and a sense of belonging. Explore the West Side today and discover the charm that awaits you in this remarkable part of the Windy City!

Newest West Side Homes with Greystone Style

$249,900

4 Beds ⋅ 2 Baths ⋅ 12801938 MLS ⋅ NEW Status

**VACANT CHICAGO GREYSTONE | POTENTIAL THREE-UNIT CONVERSION | VALUE-ADD OPPORTUNITY NEAR MAJOR WEST SIDE REDEVELOPMENT | ESTIMATED RENOVATED 3-UNIT ARV $590K-$699K.** Delivered completely vacant, this 1903 limestone-front Classical Revival greystone in East Garfield Park, on a 25x125 RM-5 lot, is a true value-add canvas: two existing units (each 2 bed/1 bath; 9 rooms, 4 beds total), a full unfinished basement, original stone facade, and 2 exterior parking spaces. **The property requires a complete gut renovation, including extensive interior demolition and rehabilitation, and is best suited for experienced investors and contractors prepared to undertake a major restoration project.** The building is being sold as-is, and the property cleanout has been completed. Interior photos are available for buyers to review the property's current condition. **THE THIRD-UNIT PLAY:** Chicago's Additional Dwelling Unit ordinance, citywide since April 1, 2026, allows one conversion unit in eligible 1-4 unit buildings at least 20 years old in RM districts, with no added parking required and an exemption from minimum lot area per unit. Owner-occupancy and block-face limits may apply in the City's West ADU zone, and Department of Housing pre-certification, permits, and building-code compliance (including basement ceiling height and egress) are required. A third unit is not currently permitted or guaranteed; buyers should verify eligibility with the City and their architect. **WHY THE UPSIDE MATTERS:** Within one mile in the last six months, fully renovated vintage 3-flats closed at $589,000-$635,000 (3169 W Monroe, $635K), a fully remodeled 3-flat closed at $699,000, and renovated 2-flats with finished lower-level duplexes closed at $590,000-$610,000. Based on those closed sales, we estimate a fully renovated legal 3-unit after-repair value of approximately $590,000-$699,000, or roughly $500,000-$610,000 as a renovated 2-flat with a finished lower level. These are estimates only, not an appraisal or guarantee, and depend on renovation scope, condition, permits, and City approvals. **LOCATION:** East Garfield Park, steps from the Kedzie-Homan Blue Line and the I-290 Eisenhower, about 1.3 miles to the Illinois Medical District, and roughly 1.9 miles from the United Center on the Near West Side, where the $7 billion, 55-acre 1901 Project broke ground in June 2026 and received a full building permit for its 6,000-capacity Music Hall in November 2026 (Phase 1 targeted for 2028). Close to Garfield Park and the Conservatory, with fast access to downtown. **STRATEGIES:** Full renovation and resale, a long-term hold with potential three-unit income, or owner-occupancy with rental income, subject to financing and legal-use requirements. Cash or renovation financing recommended. Vacant and easy to show: schedule a private showing through ShowingTime. The property has been fully cleaned out, and interior photos are now available to showcase its existing condition and renovation potential.

3332 W Congress Parkway, Chicago

$325,000

6 Beds ⋅ 3 Baths ⋅ 12801023 MLS ⋅ NEW Status

Classic Chicago brick two-flat in West Garfield Park. This is a solid addition to any investment portfolio or perfect for an owner-occupant looking to build rental income. This well-maintained property features two spacious units, each with separate utilities. ***The first floor has two bedrooms, one bathroom, a kitchen, a formal dining room, a living room, and an outdoor space. The first-floor duplex leads to the lower level, which has one extra bedroom, one bathroom, a LARGE family room, and an eating/cooking area, with full access to the laundry room. ***The 2nd floor has 3 bedrooms, 1 bathroom, a kitchen, a formal dining room, a LARGE living room, and an outdoor space. ***Recent updates include granite countertops, ceramic backsplashes, refinished 2nd-floor hardwood floors, new laminate floors on the 1st floor, and fresh paint throughout. Perfect for FHA financing. 12 FT CEILINGS. A newer rubber roof was installed around 2008; the rear porch & decks were torn down and rebuilt around 2008. Newer double-pane thermal windows. Both units have central heat and air conditioning. FHA FINANCING

4352 W Monroe Street, Chicago

$315,000

5 Beds ⋅ 2 Baths ⋅ 12801197 MLS ⋅ NEW Status

Survey has been ordered on this property and is in possession of the seller. Please note, the survey revealed that the parcel to the east of the seller's property is not owned by the seller. Per the records that we have obtained, it appears that the City of Chicago owns that property. Tax bills have not been paid on the parcel. The seller's garage does encroach on the parcel to the east. The seller will take no action on this and the title company will not insure over this encroachment.

4333 W Van Buren Street, Chicago

$229,999

8 Beds ⋅ 5 Baths ⋅ 12795337 MLS ⋅ NEW Status

Attention Investors, Rehabbers, and Developers! Excellent opportunity to transform this two-unit property located in Chicago's North Lawndale neighborhood. The building has already been gutted and is ready for renovation, offering a blank canvas for your next investment project. Restore this building into a desirable two-unit rental property or explore other redevelopment possibilities, subject to applicable zoning and city approvals. Conveniently located near public transportation, neighborhood parks, shopping, and major expressways. Bring your contractor, creativity, and vision to unlock the potential of this value-add investment opportunity. Property requires renovation and is being offered in its current condition.

3130 W 16Th Street, Chicago

$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 ⋅ ACTIVE 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

$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

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West Side Homes with Greystone Style

Newest West Side Homes with Greystone Style

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