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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.

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

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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

Exceptional, down-to-the-studs 2025 renovation of a classic Lakeview Greystone-moments to Hamilton Elementary, Southport Corridor dining and boutiques, Wrigley Field, neighborhood parks, and transit. Timeless Chicago architecture reimagined for turnkey living and comprehensively updated with all-new systems-including roof, siding, mechanicals-and a luxury appliance package (manufacturer warranties). The chef's kitchen features artisan-crafted cabinetry, Sub-Zero refrigerator and freezer, Wolf 36" gas range, built-in microwave drawer, and Bosch 800 Series dishwasher. The spa-level primary bath showcases Kohler fixtures, Toto toilets, and a sculptural Bordeaux soaking tub; all bedrooms include fully built-out custom closets. Design highlights include soaring 10'+ ceilings on the main and upper levels, white-oak flooring, a European black-metal entry door, and curated finishes. The finished lower level (9'+ ceilings) adds a custom wet bar with designer backsplash and a Danby wine cooler. Smart comforts include dual-zone high-efficiency HVAC, tankless water heater, Nest thermostats, CAT-5 wiring, whole-home audio, and pre-wired security. Outdoors, a low-maintenance backyard with premium turf and concrete walkways leads to a detached two-car garage with potential for a rooftop deck (contractor available separately). A luxury home built for comfort, longevity, and style-schedule your private tour today. $1,749,000 Active

1519 W Addison Street Chicago, Illinois

3 Beds 4 Baths 2,805 SqFt 0.07 Acres

Experience elevated urban living in this remarkable newly renovated and expanded 6-bedroom/6.5-bath luxury residence, offering 5,400+ SF of refined, professionally designed interior and ~2,000 SF of exceptional outdoor living across 4 private areas. Situated on a 30' wide lot along picturesque Magnolia Ave, this stunning greystone showcases superb craftsmanship and exudes luxury at every turn. Striking facade w/broad limestone steps leads into a beautiful marble foyer w/antique mirror, accent panel wall & elegant bronze chandelier. Formal living room sets warm inviting tone w/limestone fireplace framed by built-in floating shelves and flooded w/sunlight through oversized French windows. The heart of home is gourmet kitchen designed w/custom shaker-style cabinetry & paired w/massive Calacatta quartz island, gleaming brass pendants, and top-of-the-line Thermador appliances. Perfectly suited for both intimate gatherings and grand-scale entertaining, the open layout flows effortlessly from expansive kitchen and dining into spacious family room adorned w/arched custom built-ins & another fireplace connecting to outdoors for alfresco dining on heated raised patio or garage roof deck for unforgettable gatherings. Second level offers 4 beds/ 3 baths, including serene primary suite w/balcony, dual walk-in closets, Kohler spa-like bath w/custom vanity, steam shower/rain shower, floating soaking tub, and porcelain checkerboard floors. Laundry room completes this level for convenience. PH level unveils versatile lounge room w/sleek wet bar, wine cellar, and spa-like bath. It opens to a spectacular 800 SF terrace w/sweeping city views. The lower level expands w/2 more bedrooms, 2 full baths, another laundry, rec room w/media built-ins, wet bar w/beverage fridge, and heated LVT floors -perfect for guests or in-law/au pair living. Additional highlights include white oak flooring across three levels, radiant heated baths, full smart-home integration (Nest, AV wiring, intercom, security system w/cameras), snow-melt on front steps, and a newly built 3-car garage w/dual EV chargers. Situated in coveted Blaine School District, steps from Southport Corridor dining, boutiques, cafes & iconic Wrigley Field. It's a rare offering that embodies city living at its finest, blending timeless elegance w/modern comfort. $3,275,000 Active

3719 N Magnolia Avenue Chicago, Illinois

6 Beds 7 Baths 5,419 SqFt

Welcome to Maywood !!! A Savvy investors Gem. This home is priced to sell fast! Seller is looking for cash and quick renovation loans to take this off his hands. Needs a full remodel, but can easily create a back end of huge upside potential. Gutted and framing is almost complete! The developer that gets this property will easily renovate this into a masterpiece and deliver a spacious completely renovated GEM. Maywood is experiencing tons of renovations and this is right for the taking. Don't let this one slip away!!!! $210,000 Active

815 S 6th Avenue Maywood, Illinois

4 Beds 3 Baths 2,400 SqFt

Step inside this timeless greystone and discover a thoughtfully updated home that perfectly balances classic charm with modern comfort. Behind its elegant facade lies an ideal floorplan, designed for both everyday living and effortless entertaining. The main level welcomes you with a spacious front living and dining room, featuring a cozy gas fireplace and stylish finishes throughout. The updated kitchen showcases white shaker cabinetry, updated stainless steel appliances, a timeless subway tile backsplash, and an oversized walk-in pantry. A charming breakfast nook sits just off the kitchen, leading into a sunny mudroom that opens to a west-facing back deck-perfect for grilling and dining al fresco. Upstairs, you'll find three generous bedrooms, including a luxurious primary suite with an expansive walk-in closet and a spa-inspired bath. Indulge in the free-standing soaking tub, oversized walk-in steam shower with multiple heads (rain, wand, body sprays), and dual vanities. An adjoining room makes a great office, nursery, or dressing room. Two additional bedrooms share a spacious Jack-and-Jill bath with double sinks. A side-by-side laundry setup on this level adds everyday convenience. The beautifully renovated lower level offers a large family/recreation room that flows seamlessly into a flexible play space-ideal as a guest suite-complete with its own stunning ensuite spa bath. Out back, enjoy a private, low-maintenance turf yard that offers year-round greenery and a great space for play or relaxation. Located within the coveted Coonley School District, and just steps from the vibrant dining, shopping, and parks of Lincoln Square and North Center, this is an exceptional opportunity to own a move-in ready single-family home in one of Chicago's most desirable neighborhoods. $1,200,000 Active Under Contract

4344 N Damen Avenue Chicago, Illinois

4 Beds 4 Baths 3,623 SqFt 0.074 Acres

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! $539,900 Active

6442 S INGLESIDE Avenue Chicago, Illinois

4 Beds 4 Baths 2,646 SqFt

Perfectly situated in a discreet upscale enclave east of Sheridan road. Beautifully tucked away is where you'll find this gorgeous estate on a professionally landscaped .659 acre. With exceptional quality, elegance and design throughout there are many updates that have been done over the last 3 years. Upon entering the foyer you'll see 12-14 ceilings and gorgeous marble floors. New Kitchen with state of the art appliances, an expansive island, a true Chef's dream with butler's pantry, Stainless steel Subzero appliances, Cristallo Quartzite counters, double sinks, an espresso bar, fireplace and lots of space for eat in kitchen. Brand new theater that rivals any that you've ever been to, gym, game room, a wine room that holds roughly 1000 bottles, completely renovated 3.5 car garage with custom dog grooming station, as well as a one year new outdoor kitchen made for entertaining with state of the art grill and pizza oven with custom limestone fireplace. The lower level has been designed to accommodate one's treasured art collection with special lighting to showcase your personal collection, plus 5th bedroom and bath. Master suite is enormous for his and hers spaces, fireplace & sitting area, a massive closet and dressing area with island, double sinks, steam shower, Jet tub and heated floors: a perfect oasis. All bedrooms are ensuite and quite large with generous closet space. Gorgeous outdoor areas can be found around the entire exterior of home on first and second floors, including a 2nd floor deck overlooking the beautifully landscaped yard offering spectacular views, with fireplace and plenty of room for couches and seating to enjoy those warmer summer evenings. Additional features include an elevator, heated flooring throughout, Control 4 security system, 8 fireplaces in total, a stunning warm and inviting library with sliding ladder, perfect to cozy up in and read that book you've had on your list. The magnificent staircase with custom iron railing leading up to 2nd floor with skylight above showcases the sophistication throughout that can be found within this very special home. This stunning property is not only high tech in many ways, it also caters to family living with so many new design features that allow for children and adults to have fun without ever leaving. A true statement property. $4,250,000 Active

977 Sheridan Road Winnetka, Illinois

4 Beds 7 Baths 8,294 SqFt 0.659 Acres

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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.

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