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CHICAGO GREYSTONES

and beautiful historic Chicago homes

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

This stunning Greytone single-family home in the heart of Woodlawn offers a rare opportunity for both homeowners and investors. With incredible curb appeal, this classic design is nestled on a peaceful, tree-lined street in a prime location. Inside, the main level showcases an open floor plan with abundant natural light, hardwood floors, exposed brick, a cozy fireplace, recessed lighting, and soaring ceilings. The kitchen opens to a deck that leads to the gated rear area, providing a great space for outdoor enjoyment. Upstairs, all three bedrooms are thoughtfully situated, including a spacious primary suite featuring oversized windows, a custom fireplace, and an expansive bath with a walk-in shower. The finished basement adds even more living space with a large recreation room, an additional bedroom, a full bath, and a laundry area with exterior access. With much of the major work already done, this home is ready for your vision and finishing touches to unlock its full potential. Ideally located near the University of Chicago, the upcoming Obama Presidential Library, Jackson Park, the Museum of Science and Industry, and Lake Michigan, this property offers unmatched convenience. Easy access to Lake Shore Drive, the Metra, UC Charter Woodlawn High School, and Hyde Park shopping ensures a seamless blend of cultural, recreational, and transportation amenities. Fully gated for added privacy, the rear area appears to have space for a parking pad, though buyers should verify plans with the city. This vacant home is easy to show-don't miss out on this incredible opportunity!

$344,900 Active

6450 S Greenwood Avenue Chicago, Illinois

3 Beds 4 Baths 1,988 SqFt 0.06 Acres

Classic Chicago Greystone home on one of the Gold Coast's best blocks, just steps from the lakefront and some of the best shopping and dining. Restored to perfection, this ultra charming home offers 10' ceilings, beautiful woodwork, and fabulous attention to detail throughout. The outdoor space for this home is exceptional as well! The front living space features a double-door entry, large north-facing windows, plus a second seating area or piano room with a granite fireplace as the focal point. There is gracious formal dining with an original marble fireplace, pantry storage, plus butler's pantry access to the kitchen. The south-facing kitchen has exceptional natural light and offers an island with bar seating, white cabinetry, all stainless-steel appliances, granite countertops, plus the most charming eat-in space. A lovely rear staircase with custom runners leads to the gorgeous 2nd-level deck, complete with the best finishes and allowing for easy entertaining. The second level of the home has a large bedroom with a fireplace, a full hall bath, plus a huge family room or 3rd bedroom with a wet bar and gorgeous bay windows overlooking Elm Street. Devoted entirely to the primary suite, the third level has a large bedroom with a fireplace, an amazingly sunny "wet room" style bath, and a true dressing room with access to a Juliet balcony and a staircase down to the second-floor deck. The lower level is superbly finished with two guest bedrooms, each with a designated bath, ample storage, and a family room/office space. There is a secondary front entry to the lower level, which would allow for a great nanny or in-law quarters. A truly spectacular find in the Gold Coast, in the best location and within the Ogden School District! Easy parking within a 2-minute walk.

$2,250,000 Active

63 E Elm Street Chicago, Illinois

5 Beds 5 Baths 4,740 SqFt

Nestled in the heart of Park Manor, this exquisite four-bedroom, three-and-a-half-bathroom Georgian is a stunning blend of classic architectural charm and contemporary sophistication. From the moment you step inside, the gleaming hardwood floors and open-concept layout invite you into a space designed for effortless elegance and everyday comfort. The first floor is a masterclass in modern design, boasting a seamless flow between the living, dining, and kitchen areas. White shaker cabinetry, quartz countertops with a waterfall edge, and sleek stainless steel appliances create a chef's dream kitchen-perfect for both intimate meals and lively gatherings. Natural light pours in through large windows, highlighting the home's meticulous craftsmanship and thoughtful design. Upstairs, the primary suite is a private retreat, featuring a spa-like bathroom with a double vanity, private linen closet, and striking black-and-white fixtures that add a bold touch of elegance. Every detail has been curated to create an atmosphere of relaxation and refinement. For those who love to entertain, the sprawling lower-level family room offers a versatile space ready to accommodate any lifestyle. Whether transformed into a vibrant entertainment hub, an in-law suite, or a stylish teenager's private apartment, the possibilities are endless. Step outside, and you'll find a private backyard escape, complete with a deck and patio, ideal for hosting summer soirees or simply unwinding in your own slice of outdoor paradise. This Park Manor masterpiece is more than just a home-it's a statement of style, comfort, and functionality. Whether you're looking for a serene retreat or the ultimate entertainer's dream, this residence delivers it all.

$309,000 Active

215 E 69th Place Chicago, Illinois

4 Beds 4 Baths 1,850 SqFt

Located in highly desirable Greystone Ridge subdivision, this home is built to impress. 9' entry with chandelier light leads to an open floor plan and spacious family room showcasing a ceiling to floor stone fireplace. Perfect for entertaining, the kitchen features a large island with quartz countertop, custom cabinets, glass tile backsplash, built-in double ovens and microwave, 30'' cooktop and metal hood, and large area for table. Great space for entertaining includes butler pantry with bar and walk in pantry. Elegant formal dining room features coffered ceiling and wainscoting. Custom silhouette shade in dining room and kitchen. Just off the kitchen is an extra large laundry area with closet. Perfect for entertaining, the large covered Lanai is just off the kitchen where the view is spectacular. Office and bath are just off the main hallway. Double wide staircase leads to the second floor where large master bedroom has 2 walk in closets ( one is room size). Luxurious bath has his/her vanities, walk in shower and free standing tub. Other 3 bedrooms have generous walk in closets and ceiling fans. There are 3 full size bathrooms upstairs. All bedrooms have vaulted ceilings and plantation shutters. Full finished 9' basement has 5th bedroom. Full bath and fabulous open family room are perfect for entertaining or related living. 3 car garage with lots of storage. Excellent Orland location. Close to schools, shopping, and expressways.

$995,000 Active

11454 Boulder Drive Orland Park, Illinois

4 Beds 5 Baths 3,634 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!

$2,795,000 Active

1414 N Mohawk Street Chicago, Illinois

6 Beds 5 Baths 5,900 SqFt

Located in the heart of Chicago's Gold Coast, 45 E Division seamlessly blends the charm of historic architecture with a meticulously executed gut renovation, bringing modern luxury and top-tier design to every detail. Timeless Design Meets Modern Living. This end-unit home, perfectly positioned with tree-top views looking up Astor Street, enjoys abundant natural light from its north, west, and south exposures. Thoughtfully reimagined with a tasteful full-scale renovation, this residence boasts a custom Christopher Peacock kitchen with exquisite finishes and state-of-the-art appliances. High-end LED lighting, three elegant fireplaces, and spacious, reconfigured living areas create a perfect balance of warmth and sophistication. An Entertainer's Dream. Designed for effortless entertaining, the open-concept layout flows from the gourmet kitchen to the formal dining area, which opens onto a 30-foot deck-ideal for gatherings or quiet outdoor relaxation. A top-floor family room with a wet bar leads to a roof deck with a pergola, offering breathtaking city views and a private retreat. Private Luxury & Flexible Spaces. The primary suite is a true sanctuary, featuring a spa-like bath and a custom dressing room designed for style and function. Three additional bright and spacious bedrooms on the upper levels ensure ample room for family and guests. The lower level includes an exercise room and a guest suite with private exterior access, ideal for a live-in nanny, guests, or a home office. Sophisticated Features & Prime Location. Enhancing both convenience and luxury, a 3-stop passenger elevator provides effortless access to every level. Additional highlights include an attached garage with a lift for a second car and generous outdoor space. Ideally located just steps from the Division Street farmer's market, world-class dining, lakefront parks, and public transportation, this home also sits within the Ogden Elementary and Lincoln Park High School districts, with top private schools like Catherine Cook and Latin School of Chicago just minutes away. This exceptional, fully renovated residence is rare in one of Chicago's most desirable neighborhoods. Don't miss your chance to make it yours!

$2,399,000 Active

45 E Division Street Chicago, Illinois

4 Beds 6 Baths 4,300 SqFt

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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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