Buying  • Selling  • Investing  • Information

CHICAGO GREYSTONES

and beautiful historic Chicago homes

Chicago Greystones for Sale

The
Historic
Significance

Your home tells a story that will be heard for generations. Work with a real estate broker that understands the nuances and culutral significance that your property brings to the table.

list your home

Unrivaled Service

Every little detail matters. Whether you’re acquiring or selling, you’ll be meticulously guided through every step of the transaction and beyond.

learn more

UNRIVALED SERVICE

Every little detail matters. Whether you’re acquiring or selling, you’ll be meticulously guided through every step of the transaction and beyond.

learn more

Chicago Greystone Homes for Sale

currently on the market and recently sold

Enter into timeless elegance with this beautifully renovated 3-story Greystone located in the heart of Woodlawn, one of Chicago's most vibrant and rapidly developing neighborhoods. This spacious home features 4 bedrooms, plus an additional bedroom in the fully finished basement-perfect for guests, extended family or a private home office. The main level boasts an open-concept living and dining area, soaring ceilings, and refinished hardwood floors throughout. It is conveniently located near the Obama Presidential Center, University of Chicago, parks, public transit and the lakefront. Don't miss this one-of-a-kind Woodlawn gem! $549,900 Active

6442 S INGLESIDE Avenue Chicago, Illinois

4 Beds 4 Baths 2,646 SqFt

Welcome to one of Old Town's finest homes built on and oversized lot and surrounded by mature gardens of Boxwood, Limelight Hydrangea and Thorndale Ivy. Enter through its custom iron gates and be ready to fall in love. This home views like a story book with all of its special features and architectural details. Full limestone and brick construction originally built in 2012 and perfected throughout 2024. Provencal inspired complements including arched doorways, palladium windows and a mansard roof are just the beginning of this romantic tale. The main living area is met by a sprawling French country kitchen featuring reclaimed wood beamed ceilings, marble countertops, a La Cornue range, double sided sub-zero, heated floors plus. Gorgeous walk out to covered arched bricked patio leading to multiple outdoor spaces including outdoor fireplace, built in Wolf cooking station and garage roof top with pergola. Six inch plank solid oak flooring continue up the winding custom iron staircase to the second level to the primary, second and third bedrooms. Primary suite features its own private outdoor space and a simply majestic marble bath and walk in closet. 3rd level is currently configured as a wet bar leading to a fun music /entertainment space plus office and can easily be bedroom #6. This level leads out to double level trex outdoor space including an outdoor rain head shower and 4th floor viewing deck to enjoy the show stopping skyline. Lower level with tumbled stone heated floors and great theater room with top of the line surround sound/wet bar, 2 additional bedrooms, a 1500 bottle wine cellar, and (huge) sauna. The entire house is controlled by a state of art Crestron system (2024 seller investment of over 250 k) with full security cameras, electronically controlled window treatments +. All top of the line televisions and speakers will transfer with the home. Electronic car charging station in garage, snow melt sidewalks leading to the house-- true conveniences in Chicago. Interior is fully sprinklered and the exterior has a full irrigation system. There are so many surprises this special home holds, you must visit to know them all. Truly a turn key property. We promise not to disappoint and we will see you soon! $2,490,000 Active

1414 N Mohawk Street Chicago, Illinois

6 Beds 5 Baths 5,900 SqFt

This classic Chicago-style brick home blends timeless architecture with a classic Bridgeport location. Recently tuck pointed on the north and south sides of the building and featuring fully enclosed back porches, this property is zoned as a two-family residence but currently functions as a spacious single-family home-offering versatility for future use or investment. Inside, the main level boasts a spacious kitchen with an eat-in area, custom banquette seating, built-in desk, and a large walk-in pantry. A convenient mudroom off the kitchen leads to a generous deck-perfect for outdoor entertaining-alongside a private backyard with patio space and a 2-car garage. The first floor also includes a full bath, cozy den, and flexible living spaces. Upstairs, the second floor features a secondary living area, two bedrooms, and a full bath. The primary suite includes a large walk-in closet and a separate sitting area, offering a quiet retreat. The third floor adds two additional bedrooms, ideal for guests, home offices, or playrooms. Split mechanicals offer efficiency and peace of mind: two furnaces, two A/C units, dual electrical panels, and two brand-new water heaters (2024). Whether you're seeking room to grow or multi-unit potential, this home delivers unmatched space and character in a classic Chicago footprint. $550,000 Active

3432 S Union Avenue Chicago, Illinois

4 Beds 2 Baths 2,293 SqFt

Rare Opportunity in Austin - Classic Greystone at an Incredible Value! Don't miss this chance on a stunning Single-Family Greystone in the sought after Austin neighborhood - just minutes from Oak Park at half the cost! Properties like this rarely hit the market. This home has beautiful hardwood floors, 2 charming fireplaces, and a finished basement, perfect for an in-law suite or a fun entertainment space. The choice is yours! A solid property with tons of potential, ready for your creative vision. Don't miss out on this Great Investment in a Prime Location. Sold As- Is. Property needs new roof. Water damage in back porch- needs tear down or rebuild. $214,997 Active

5822 W Washington Boulevard Chicago, Illinois

4 Beds 3 Baths 2,040 SqFt

Coveted Greenview Avenue, in Chicago's Graceland West neighborhood, is by far one of the city's most sought-after locations. Renovated Greystone sitting on an over-sized 27' x 161' lot. Enjoy the best of both worlds - vintage exterior and thoughtfully renovated interior complimenting a modern lifestyle. As you slip behind the original vintage Greystone facade, you'll find large, open rooms with all of the luxurious finishes you'd expect including: 5 BRs (4 on the 2nd floor), 4.2 bathrooms (3 en-suite), extra-large chef's kitchen with a Wolf & Sub-Zero appliance package, Grohe fixtures, natural stone bathrooms, extensive millwork, hardwood floors, butler's pantry, mudroom, 2.5 car garage, wine cellar, media room and a private landscaped rear and front yards. Make the best of Summer by taking advantage of the amazing outdoor space - large deck on the garage and roof deck with beautiful views. $2,395,000 Active

4148 N Greenview Avenue Chicago, Illinois

4 Beds 6 Baths 5,250 SqFt 0.1 Acres

Own a Rare Piece of Chicago History Don't miss this incredible opportunity to restore a true architectural gem. This massive Romanesque Revival Greystone, built circa 1890 by renowned architect Charles Weary, sits on an extra-wide 35' x 125' lot in red-hot East Garfield Park. Rich in character and potential, this rarely available historic mansion offers the perfect canvas for your vision. Originally constructed as a grand single-family residence, the home retains its classification, but with generous square footage and highly desirable RM-5 zoning, it also presents a prime investment opportunity. This is a full gut-rehab project, ideal for seasoned developers or passionate preservationists. THE PROPERTY MUST BE SOLD with the adjacent XL vacant lot to the west (3334 Warren listed separately), adding another 40 feet of frontage and expanding your possibilities even further. Due to the home's current condition, room counts and dimensions are estimated. Property is being sold as-is. Opportunities like this in East Garfield Park are becoming increasingly rare-act now to secure a historic footprint in one of Chicago's fastest-rising neighborhoods. $550,000 Active

3328 W Warren Boulevard Chicago, Illinois

5 Beds 2 Baths 3,248 SqFt

view all greystones for sale

We are known by the company we keep.

As a $5 billion organization and one of the highest-performing brokerages in the nation, Berkshire Hathaway HomeServices Chicago can deliver results for you. We are world-renowned for our luxury marketing and set the standard for upper bracket representation. Our brokers take great pride in providing that same high level of personalized service to create a luxury experience for all clients, one that you will truly appreciate. We are committed to being at the forefront of the industry by doing all that we can to anticipate your real estate needs and exceed your expectations.

get started

Steven Kowalski

Real Estate Broker

 

Selling or acquiring a greystone or any other historical home requires an agent with the tools and expertise to guide you through every step of the process. Whether you’re buying or selling, trust me to deliver results for you.

contact