Northwest Side Homes with Greystone Style

Welcome to the Northwest Side of Chicago, a vibrant neighborhood that beautifully marries urban convenience with suburban charm. Nestled within Cook County, this area is known for its rich history, diverse culture, and welcoming community spirit. The Northwest Side boasts a variety of parks, local eateries, and independent shops, making it an ideal place for families, young professionals, and retirees alike.

One of the standout features of this neighborhood is its stunning Greystone-style homes. These architectural gems, characterized by their distinctive limestone facades, large bay windows, and intricate details, tell the story of Chicago’s architectural evolution. Built primarily in the late 19th and early 20th centuries, many of these homes have been lovingly restored, offering a perfect blend of classic charm and modern amenities. Living in a Greystone not only provides a unique aesthetic but also a sense of history that connects you to the heart of Chicago.

Residents of the Northwest Side enjoy easy access to public transportation, making commuting to downtown Chicago a breeze. With a strong sense of community, numerous local events, and a variety of recreational activities, there’s always something to do. Whether you’re strolling through the picturesque streets, enjoying a meal at a local café, or participating in neighborhood festivals, the Northwest Side offers a lifestyle that is both enriching and fulfilling.

Explore the Northwest Side today, and discover the perfect Greystone home that will not only meet your needs but also enrich your life in this dynamic Chicago community.

Newest Northwest Side Homes with Greystone Style

$1,199,000

5 Beds ⋅ 3 Baths ⋅ 12773705 MLS ⋅ ACTIVE Status

Stunning Chicago jumbo 2 flat greystone just steps from Humboldt Park! Set on an oversized lot, this impressive greystone is exceptionally wide itself, taking advantage of the additional lot width and creating unusually spacious, open residences throughout. This truly special property offers an exceptional combination of classic character, generous living space, and thoughtful amenities. The spacious former owner's unit features beautiful hardwood floors throughout, an extra-wide open floor plan, an oversized bathroom, and the convenience of in-unit laundry. With its impressive greystone facade, oversized lot, exceptionally wide and spacious apartments, and prime location, this property offers a rare combination of character, scale, and location. The width of the units creates for expansive living and dining spaces with an open, feel that sets these apartments apart. An outstanding opportunity for an owner-occupant or investor seeking a distinctive multi-unit property in one of Chicago's most vibrant neighborhoods. Also ideal for someone looking to convert into a spectacular single family residence. Outside, a beautifully manicured lawn adds rare green space and wonderful curb appeal. The property also offers a common laundry room in the basement, three dedicated tenant storage areas, and a three-car garage. A truly special property that must be seen to fully appreciate its exceptional size, and character. Rent increases have been provided to tenants, with new rents scheduled to be in effect January 2027. New monthly rents: Unit 1 - $2,600; Unit 2 - $2,700; Garden Unit - $1,800, for total scheduled rental income of $7,100/month or $85,200 annually. Each apartment gets one designated garage spot included. Property also generates approximately $1,600/year in coin laundry income, bringing total projected annual income to approximately $86,800. **Second-floor dining room light fixture and bedroom fixture is owned by the tenant and is excluded from the sale. Seller and listing broker make no representation as to the legality of the basement apartment.

3244 W Potomac Avenue, Chicago

$1,200,000

5 Beds ⋅ 3 Baths ⋅ 12748261 MLS ⋅ ACTIVE Status

Located in the heart of Logan Square, this classic brick two-flat underwent a full gut renovation in 2020, thoughtfully preserving its original architectural details while introducing updated finishes, modern systems and functional living spaces. The result maintains the vintage charm of a traditional Chicago two-flat while offering the comfort and convenience of a fully renovated home. The first-floor duplex-down offers 3 bedrooms and 2 full baths across two levels. The main level features a living room with the original fireplace and mantel, a dedicated dining room, two bedrooms, a full bath and a fully appointed kitchen. The lower level expands the living space with a spacious family room, perfect as a media room, home office or additional flex space, along with a third bedroom and second full bath. The second-floor unit offers 3 bedrooms and 1 full bath with a comfortable, functional layout and its own original fireplace mantel, preserving another piece of the home's vintage character. Both units feature enclosed porches, central heat and air conditioning, and updated interiors that complement the building's original details. A shared laundry area is conveniently located on the lower level, and the property also includes a shared backyard and detached 2-car garage. Ideally situated near Logan Square's restaurants, cafes, shopping, entertainment, parks and neighborhood amenities, this turnkey two-flat offers versatility for an owner-occupant, investor or multigenerational living. Located within the Northwest Side Housing Preservation Area, with two updated units, flexible living spaces and a prime neighborhood location, this is a unique opportunity to own a classic Chicago two-flat that has already undergone a comprehensive renovation. Photos from 2020 renovation, new photos coming soon!

2428 N Rockwell Street, Chicago

$2,199,800

4 Beds ⋅ 5 Baths ⋅ 12718791 MLS ⋅ ACTIVE Status

Incredible 4 bedroom, 4.5 bathroom approximately 5,000-square-foot Wicker Park single family home including an oversized and high speed commercial elevator accessing all 5 floors! Multiple outdoor spaces including an outdoor rooftop hot tub and additional lap pool above garage deck! Custom all-brick and stone exterior construction, top-floor sunroom/ entertainment space includes, wet bar, double roofdecks with incredible city and sunset views. Newly updated kitchen includes Sub-Zero and Wolf appliances plus built-in Miele espresso machine. Full-floor primary suite includes, massive walk-in closet, gas fireplace, large separate steam shower and soaking tub. Lower level includes radiant floor heating, second family room, gym and wine room. The heated garage features 14' ceilings, lift-ready capacity & a 240V/60A Tesla charger. Freshly repainted in 2026. Steps to the 606 Trail, Milwaukee Ave boutiques & Division St dining - a turnkey retreat in Chicago's most vibrant corridor.

1220 N Damen Avenue, Chicago

$629,000

11 Beds ⋅ 3 Baths ⋅ 12661028 MLS ⋅ ACTIVE Status

Fully renovated Greystone two-flat investment property situated on a 6,969 SF lot. The building features two spacious units plus a non-conforming garden apartment, offering strong rental income potential. Unit 1 consists of 4 bedrooms and 1 bath (approx. 1,300 SF), Unit 2 offers 5 bedrooms and 1 bath (approx. 1,350 SF), and the garden unit includes 2 bedrooms and 1 bath. Both main units feature large living and dining areas, hardwood floors, updated kitchens with granite countertops, center islands, dark wood cabinetry, and stainless-steel appliances. Significant improvements include updated plumbing, 200-amp electrical service, newer furnace, central air conditioning, hot water tank, roof, and lighting. Additional features include a spacious rear yard and onsite parking. Current monthly income totals $7,200 plus $300/month from parking. Turn-key investment opportunity with stable cash flow in a classic Chicago Greystone building.

35 N Mayfield Avenue, Chicago

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Northwest Side Homes with Greystone Style

Newest Northwest Side Homes with Greystone Style

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