Cook County Homes with Greystone Style

Welcome to Cook County, Illinois, a vibrant area teeming with culture, history, and diverse communities. As the second-most populous county in the United States, Cook County is home to the bustling city of Chicago, renowned for its stunning architecture, world-class museums, and an eclectic culinary scene. The county boasts a rich tapestry of neighborhoods, each offering its unique charm and character, from the historic streets of Oak Park to the scenic beauty of the Cook County Forest Preserves.

One of the standout architectural styles that grace this region is the iconic Greystone. These magnificent homes, often characterized by their sturdy limestone facades and intricate detailing, embody a timeless elegance that speaks to the rich history of the area. Greystones typically feature spacious interiors, high ceilings, and large windows that invite natural light, creating a warm and inviting atmosphere. Many of these homes have been lovingly restored, preserving their historic charm while incorporating modern amenities to suit today’s lifestyle.

Living in a Greystone home in Cook County means embracing a sense of community and connection to the area's storied past. Whether you’re strolling down tree-lined streets, enjoying local parks, or indulging in the vibrant arts scene, you’ll find that Cook County offers an unparalleled quality of life. With a variety of Greystone homes available, there’s no better time to explore the unique opportunities this stunning architectural style has to offer. Come discover your dream home in the heart of Cook County, where history and modern living harmoniously coexist!

Newest Cook County Homes with Greystone Style

$395,000

5 Beds ⋅ 2 Baths ⋅ 12804890 MLS ⋅ NEW Status

Historic Greystone Opportunity in the Heart of Bronzeville Currently used as a single family but has 3 unit status. This is a blank canvas for your ultimate dream home or investment property! Nestled in Chicago's historic and vibrant Bronzeville neighborhood, this massive, all-brick 3-story Greystone has multi unit zoning and stands ready for a stunning architectural rebirth. Representing a rare chance to blend timeless late-19th-century elegance with modern luxury, this property is being sold As-Is, offering a phenomenal opportunity for savvy investors, developers, or ambitious live-in visionaries. Stately Architecture & Historic Details: Built in 1883, this grand home features a soaring 3-story layout with beautiful architectural bones, including an iconic stone facade, historic front and rear stairwells, and exquisite original stamped wood walls and crown molding. Features a ground-level walk-out basement. Skip a massive step in the planning phase! The owner has already commissioned full architectural plans for the entire home's transformation, which are available to view and utilize for your renovation. Live or invest in a neighborhood renowned for its rich cultural history, striking architecture, and booming community development. Just minutes from the sprawling lakefront, Margaret Burroughs Beach (31st Street Beach), and the historic Burnham Park-perfect for running, cycling, or enjoying Lake Michigan. Dining & Culture: Walk to a thriving local culinary scene featuring celebrated neighborhood favorites like Pearl's Place, Peach's on 47th, and Bronzeville Winery, alongside boutique coffee shops, local art galleries, and the historic Monument to the Great Northern Migration.Elite Education & Innovation: Situated near the Illinois Institute of Technology (IIT) campus and down the street from the exciting new Bronzeville Lakefront development, promising massive future economic growth. Commuter's Dream: Commuting is effortless! Located just east of the Dan Ryan Expressway (I-94) and steps from the CTA Green and Red Line stations, as well as multiple Metra stops for a lightning-fast trip into the Loop.Opportunities to restore a majestic piece of Chicago history like this do not come along often. Bring your contractor and your vision-schedule your private tour today!

3633 S Giles Avenue, Chicago

$3,500,000

5 Beds ⋅ 5 Baths ⋅ 12806433 MLS ⋅ NEW Status

A rare and seamless blend of architectural history and sophisticated modern living. Situated on one of the neighborhood's most desirable blocks, this spectacular 5,500 square foot, 5-6 bedroom, 4.5 bathroom greystone has been meticulously renovated for a comfortable contemporary lifestyle while honoring its classic Gold Coast character. The handsome three-story stone exterior is capped by an ornate, original copper pediment and roof cresting - welcoming one to the home's many well-preserved historic details. Inside, the expansive front living room offers an inviting layout with space for multiple seating arrangements, a stately fireplace, and a bright and large view, framing mature trees and beautiful Gold Coast architecture. The dining room features the second of the home's three original fireplaces and easily accommodates large family gatherings and dinner parties. The leaded-glass pocket doors provide an elegant partition between the dining room and the home's kitchen. Bathed in morning light, the expansive chef's kitchen is a triumph of thoughtful design and high-end utility. A thick slab of deeply veined white marble tops the oversized central island, which features comfortable counter seating beneath pendant lighting. The culinary suite is anchored by a 48" Wolf range with dual ovens, a Sub-Zero refrigerator, a Bosch dishwasher, and a dedicated wine and beverage fridge. A large bay window, built-in banquette seating, and custom storage cleverly tucked under the rear staircase ensure this magnificent space is as functional as it is beautiful. Stepping out onto the rear terrace reveals a curated private escape. A custom pergola provides shade, while integrated infrared heaters extend the space's use into the cooler months. Designed for effortless entertaining, this exceptional outdoor sanctuary features dedicated areas for grilling and alfresco dining, alongside a full outdoor living room where a fire table provides an inviting focal point for evening gatherings. Back inside, the grand main staircase provides a masterclass in late 19th-century craftsmanship. Rich hardwood handrails and treads contrast with the crisp white wainscoting and expertly carved newel posts. Cleverly concealing a discreet main-floor powder room, the staircase rises past a stunning original stained-glass window to the home's upper levels. Occupying the entire front portion of the home's second level, the primary suite has a deep-set picture window with leafy street views and two closets. The ensuite primary bathroom features beautiful tilework, an oversized, spa-quality shower, separate soaking tub, and double sinks. A second ensuite bedroom with a balcony and a multi-use family room are also located on this level. The home's third floor thoughtfully accommodates three additional, generously sized bedrooms. The front bedroom with cathedral ceilings and a library wall is accessed by a pass-through 14x10ft bonus room, which can be easily tailored to your lifestyle and needs. Completing this level, the two remaining bedrooms share a classic Jack-and-Jill bathroom. The lower level is home to a large family room, a temperature-controlled glass wine room, a dedicated home gym (bedroom six) with modern bath and shower, and a rear mudroom with laundry. A two-car tandem garage completes the home. 1437 N. Dearborn is a truly exceptional and inviting home not often found in the neighborhood. This is a rare opportunity; located two blocks from Lake Michigan and Lincoln Park, in close proximity to beaches, top-rated schools, seasonal farmers' markets, world-class shopping, and fine dining.

1437 N Dearborn Street, Chicago

$469,900

9 Beds ⋅ 3 Baths ⋅ 12806374 MLS ⋅ NEW 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

$850,000

5 Beds ⋅ 4 Baths ⋅ 12805943 MLS ⋅ NEW Status

Welcome home to this beautifully renovated 5-bedroom, 3.5-bathroom Greystone. Fully rebuilt in 2016 and newly renovated in 2024, This one-of-a-kind home blends classic Chicago character with modern upgrades. The fully remodeled chef's kitchen boasts black matte stainless-steel LG appliances, a marble island with matching backsplash, extended countertops, additional cabinetry, and a spacious walk-in pantry makes it complete. It also has a large 12x20 deck, a perfect set-up for entertaining. The large living room and separate dining room makes this open concept space very enjoyable, not to mention the newly coffered ceiling den located right off the massive kitchen. It is the perfect cozy space to relax after cooking an amazing meal. The 10' ceilings, oak hardwood floors, contemporary lighting fixtures, and LED recessed lighting throughout this home gives it a luxurious feel. The massive primary suite features his-and-hers walk-in closets plus additional sleek cabinets for your shoes! It features a contemporary electric fireplace for those cozy fall/winter nights. It is the perfect space for a deep slumber and an even better space for your mornings! as you can enjoy your coffee on your own private 12x20 deck that overlooks your beautiful and tranquil backyard garden. The master bathroom have been beautifully appointed with quality finishes, a spa inspired soaking tub, separate shower, a double vanity, beautiful stylish mirrors, marble tile and heated floors. The finished walkout basement offers flexible living space with vinyl wood flooring, a full bath, a kitchenette/bar, and separate office/recreation areas plus a spacious bedroom. A perfect space for perhaps in-laws or visiting guests. All bedrooms are spacious, and there is additional storage space, throughout the home. The detached 2-car garage built in 2016, offers parking, storage, and additional flex-space potential. THIS IS A MUST SEE HOME IS PERSON TO APPRECIATE IT'S BEAUTY. Schedule your showing today.

4818 S Evans Avenue, Chicago

$4,500,000

6 Beds ⋅ 7 Baths ⋅ 12804497 MLS ⋅ NEW Status

A beautifully reimagined Gold Coast Greystone, 46 Cedar pairs an exquisite, move-in-ready three-bedroom owner's residence with a private rooftop deck and two renovated apartments currently generating $10,350 in monthly rental income. Set on a picturesque, tree-lined block just one block from Lake Michigan, this historic Chicago home brings architectural character, exceptional outdoor space, and walkable Gold Coast living together. The owner's residence spans multiple floors and has been remodeled with refined finishes throughout. Sunlight pours through south-facing bay windows, highlighting 10-foot ceilings, hardwood floors, custom moldings, built-in bookcases, and graceful arched doorways. A striking French pewter fireplace anchors the formal living room, while the gracious dining room, spacious kitchen, and inviting family room create an elegant setting for everyday living and entertaining. A convenient powder room completes the main living level. Two beautiful staircases lead to the bedroom level, where three generously sized bedrooms and an office niche provide comfortable space to unwind and work. The primary bedroom features a third fireplace and generous closet space, along with a newly remodeled bathroom with an oversized shower and sauna. On the third level, a convenient powder room and small kitchenette open to the private rooftop deck-an inviting retreat for dining, gardening, and enjoying city views. The two additional apartments have also been renovated and are currently rented, providing $10,350 per month in rental income. One apartment offers two bedrooms; the other has one bedroom. Each has a separate entrance, in-unit laundry, and its own heating and cooling systems. Outdoor living continues with a paved backyard patio and balconies off the main living levels. Two parking spaces are included. Enjoy the best of Gold Coast Chicago, with Lake Michigan, Mariano Park, celebrated restaurants, boutiques, and high-end shopping close by. A rare opportunity to own a distinctive Chicago Greystone with a substantial owner's residence, meaningful rental income, and outdoor space at every turn.

46 E Cedar Street, Chicago

$280,000

3 Beds ⋅ 3 Baths ⋅ 12803733 MLS ⋅ NEW Status

Brand new roof & freshly staged! Beautifully renovated 4-bedroom (3 +1), 2.1 baths single-family home offering a massive amount of living space across multiple levels. The bright, modern interior showcases new luxury vinyl plank floors and is anchored by a sleek kitchen featuring contemporary cabinetry, quartz countertops, and stainless steel appliances. Upstairs, you'll find three exceptionally spacious bedrooms. Downstairs, the expansive, fully finished basement provides even more room to entertain, featuring a large family room, full bath, and a fourth bedroom or private home office you can easily partition off. Throughout the home, the bathrooms have been completely updated with elegant tile and modern fixtures to create a spa-like feel. Complete with a brand-new central A/C system, a detached 2-car garage, and a prime location near shopping, parks, and tollways, this move-in-ready home truly has it all.

7000 S Eberhart Avenue, Chicago

$249,900

4 Beds ⋅ 2 Baths ⋅ 12801938 MLS ⋅ ACTIVE 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

$1,250,000

8 Beds ⋅ 3 Baths ⋅ 12796917 MLS ⋅ ACTIVE Status

A Rare Edgewater Offering! This exceptional 1905 trophy Greystone is a beautifully renovated three-unit building situated on a quiet, tree-lined street on an oversized 33' x 165' lot. Thoughtfully laid out and well maintained, this property offers an outstanding opportunity for both owner-occupants and investors. Second-Floor Unit - 3 Bedrooms / 1 Bath: Bright and inviting, this spacious unit features an extra-wide living room with beautiful views of the tree-lined street, a large separate dining room, and an eat-in kitchen with cherry cabinetry, stone countertops, and stainless-steel appliances. The kitchen opens to a sunny enclosed porch. The Lower-Level non-conforming Unit is a 2 Bedrooms / 1 Bath that boasts 8 foot ceilings with a Modern open-concept design with contemporary gray cabinetry, quartz countertops, and a peninsula island overlooking the combined living and dining area, enjoy the upgrade bath with a jetted tub and body sprays . First-Floor Unit - 3 Bedrooms / 1 Bath: An ideal owner's residence, this generous unit offers a spacious living room and separate dining room, along with an eat-in kitchen featuring cherry cabinetry, stone countertops, and stainless-steel appliances. The kitchen leads to a large, enclosed porch that connects to a stunning vaulted-ceiling four-season room. Step outside to a beautifully landscaped backyard featuring custom-paved patios and walkways, a two-car garage, and an additional carport 3rd parking space. Enjoy exceptional outdoor privacy with wood fencing along both sides of the property. Additional features include common laundry and storage in the lower level, newer and well-maintained mechanical systems, and tenants responsible for all utilities. The property also offers convenient access to transportation and neighborhood amenities, located less than one mile from the CTA Red Line and Metra, and one mile from Loyola University, Target, and lakefront. A truly special opportunity combining classic Chicago Greystone architecture, thoughtful renovations, generous outdoor space, and excellent versatility. Numerous additional improvements have been completed; Please see listing's additional information for details. (THE SOONEST CLOSING DATE AVAIBLE IS JANUARY 20,2027)

6320 N Paulina Street, Chicago

$325,000

6 Beds ⋅ 3 Baths ⋅ 12801023 MLS ⋅ ACTIVE 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

$285,000

5 Beds ⋅ 4 Baths ⋅ 12787292 MLS ⋅ ACTIVE Status

Great investment opportunity in the Greater Grand Crossing neighborhood! This Updated two-unit townhouse-style Greystone features a 3-bedroom, 2-bath unit and a 2-bedroom, 2-bath unit. Units have been updated in 2025 with new paint, vinyl floors, bathrooms, and kitchen with stainless steel appliances, center island, and white cabinetry. Lower unit has it's own back porch while the upper unit has its own private balcony. Additional highlights include a full unfinished basement for extra storage and a detached 2-car garage. Conveniently located near public transportation, shopping, dining, and major expressways. Ideal for investors or owner-occupants looking to generate rental income. Don't miss this opportunity!

101 W 72Nd Street, Chicago

$315,000

5 Beds ⋅ 2 Baths ⋅ 12801197 MLS ⋅ ACTIVE Status

Opportunity awaits with this classic Chicago greystone two-flat in the heart of the West Side. Featuring 5 total bedrooms, 2 full bathrooms, and timeless masonry construction, this property offers strong potential for investors, owner-occupants, or those looking to add value through renovation. The building includes a full unfinished basement providing ample storage and future possibilities, along with a detached 2-car garage for added convenience. Situated on a standard Chicago lot, this property combines vintage character with income-producing potential. Conveniently located near public transportation, major expressways, parks, schools, and neighborhood amenities. Whether you're expanding your investment portfolio or searching for a multi-unit property with room to grow, this classic greystone presents a unique opportunity. Property is being sold as-is. Buyers are encouraged to conduct their own due diligence regarding all property details and conditions. 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. Tankless water heater.

4333 W Van Buren Street, Chicago

$1,900,000

7 Beds ⋅ 7 Baths ⋅ 12800813 MLS ⋅ ACTIVE Status

Once in a lifetime opportunity to own in one of the best blocks in Lincoln Park right across the street from DePaul University. All 3 units on four floors were all completely gut rehabbed in 2010. Real hardwood floors throughout, very expansive floorplans with lots of natural light. Tall ceilings on every floor offering floor to ceiling windows, very large living, dining and kitchen areas. All flowing beautifully throughout. The kitchens have stone countertops, high-end appliances and walk in pantry. Large bedrooms with huge closets, Large bathrooms and in-unit laundry on all units and rear decks on every floor. The building consists of a 3 Bedroom, 3 Bathroom Duplex Down very large unit approximately 2,700 SF. The second and third floors both have 2 bedrooms with 2 full bathrooms. The second floor is very large at approximately 1,500 SF and the third floor is approximately 1,700 SF. Excellent location, beautiful rehab and historic greystone facade stonework. Units are below market rent. The second floor is currently vacant. The 1st floor duplex and third floor simplex both are leased until June 30th, 2027. There are a total of 5 PIN Numbers, as it was originally built out for condo sales. A great place for owner occupied, keep all 3 rented or sell them as High-End Condos. You can decide. Property is sold As-Is.

2131 N Sheffield Avenue, Chicago

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Cook County Homes with Greystone Style

Newest Cook County Homes with Greystone Style

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