luxury properties for sale Cook County, United States

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)

Beautifully renovated, legal 3-unit building on a quiet, tree-lined block in a fantastic Logan Square/Avondale location! Each spacious 5-room, 2-bedroom, 1-bath residence features a thoughtfully designed floor plan with gorgeous finishes, hardwood floors, high ceilings, and abundant natural light. Stunning new kitchens offer 42" wood cabinetry, Spanish quartz countertops, generous prep space, and fabulous storage. All units feature beautifully updated baths, in-unit washers and dryers, and new HVAC systems. Additional improvements include new front and rear porches and new siding. Wonderful outdoor space with a shared yard and 2-car garage. Unbeatable location just steps to Logan Boulevard, the Riverwalk, movie theater, grocery stores, Target, XSport, fantastic restaurants, shopping, and so much more! An exceptional turnkey investment opportunity in a highly desirable neighborhood!

Incredible opportunity in Avondale! This extra-wide brick two-flat sits on an expansive 50' x 125' double lot, offering exceptional space both inside and out. Each generously sized unit features three bedrooms, one full bathroom, a spacious living room, a separate formal dining room, and an eat-in kitchen. With windows on multiple sides, both units are filled with natural light, creating bright and airy living spaces throughout. The partially finished basement offers additional living space, including a bedroom and full bathroom, along with abundant storage. Outside, the oversized lot provides a spacious backyard and side yard which is a rare find in the city! A two-car detached garage completes the property. While the interiors are ready for updating, notable improvements include updated electrical plus a high-efficiency boiler installed in 2017. Whether you are an investor or an owner-occupant looking to make a property your own, this is an opportunity with tremendous potential. Ideally situated in Avondale, with convenient access to the Blue Line, expressway and all the shopping, dining, and neighborhood amenities of nearby Irving Park and Logan Square.

Excellent opportunity to own a classic Chicago brick three-flat with an additional coach house in the rear with a full basement! All units have 2 bedrooms. The apartments were updated and feature comfortable well-maintained living spaces with the convenience of in-unit washer and dryers. Located on a desirable block with easy access to public transportation, as well as Rate Field (formerly U.S. Cellular Field). The rear coach house offers additional space and includes a full basement. A great opportunity for an owner-occupant or investor looking for a solid multi-unit property in a convenient Chicago location.

Rarely available two-unit corner property with an additional in-law suite, situated on an oversized lot with a large yard in sought-after North Portage Park. Both apartments offer a sunny, functional layout with 2 bedrooms and 1 bath, while Unit 1 provides the opportunity to easily add a third bedroom, creating additional value and flexibility. In-law suite is an oversized 1 bedroom 1 bath. Property features back decks, generous outdoor space, and a large yard-ideal for outdoor entertaining, gardening, or future possibilities. Major improvements include a full tear-off roof replacement in 2024, a complete rehab of Unit 2 in 2024, and an in-law suite added in 2024. Conveniently located within walking distance of Six Corners and Portage Park, with an abundance of grocery stores, shopping, restaurants, and everyday amenities nearby. A compelling opportunity for investors, owner-occupants, or those looking for a property with multiple income-producing spaces and future upside. Units are currently under market rent.

ATTACHED SINGLE-FAMILY HOME WITH PRIVATE YARD & GARAGE ROOFTOP DECK! Introducing RiverWard: Phase 3 - a collection of 9 new construction, attached single-family homes tucked along the north branch of the Chicago River. Perfectly situated along a tree-lined, cul-de-sac along the expanded RiverWalk, this idyllic location is second to none, yet offers easy access to Southport, Roscoe Village, and the expressway. Residence 2827 N Oakley (36-F) will deliver over 3698 SF of indoor and outdoor living space PLUS 1060 SF basement and wide, detached 2-car garage. Imagine living in a home that is wider than a single-family in the area, and with more storage space too. Designed by acclaimed-developer ZSD in conjunction with Sullivan, Goulette & Wilson, the EXTRA-WIDE (19 FEET!) home boasts sophisticated and functional design for today's homebuyer. Spanning three levels of living with gracious 10-ft ceilings, this 4-suite residence also includes a family room, upstairs game room, office, fenced-in private yard, and finished garage rooftop deck. At the heart of this home is a spacious, contemporary kitchen, with immense cabinet count and integrated appliances from Sub-Zero, Wolf, and Bosch, designed to cater to both the casual cook and the culinary enthusiast. The massive quartz waterfall peninsula and full-height cabinetry throughout provides the desired function and storage expected from a single-family home. This home includes an open-concept living and dining room and a private, fenced-in 360 SF private yard complete with gas, water, and electric. A separate Powder Room and oversize Family Room complete the large main level, leading to the private backyard. The impressive, extra-wide Primary Suite is designed as a personal retreat with large bedroom, MASSIVE dressing room, and "wet room" bathroom with European glass shower, standalone tub, and double vanity with quartz countertop. The second 255 SF family/game room and private office are located on the third level. The wide, detached 2 car garage with 300 SF finish paver rooftop rounds out the lifestyle perfectly. RiverWard: Phase 3 delivers adds more in-demand row homes and attached single-family homes with unparalleled access to the expanded Chicago RiverWalk. Early buyers will have the opportunity to personalize the home and select finishes. Construction pricing available from 1.7M to 1.85M. Contact Corwin Partners for a private in-person or virtual appointment at Sales Gallery at 2977 N Clybourn.

Turnkey 3-Flat in Woodlawn - Minutes from the Obama Presidential Center! This beautifully designed three-flat features three identical 3BR/2BA units with open-concept layouts, floor-to-ceiling windows, and hardwood floors throughout. Chef-style kitchens boast quartz countertops, soft-close cabinetry, and stainless steel appliances. Each unit offers a spa-inspired primary suite, in-unit laundry, tankless water heater, private deck/patio, and shared fenced yard with 3 exterior parking spaces. Perfect for investors, house hackers, or short-term rental operators looking to capitalize on Woodlawn's rising demand. Unbeatable Location: Minutes to the University of Chicago, UChicago Medicine, and the highly anticipated Obama Presidential Center. Plus Hyde Park shopping, dining, Whole Foods, Target, and easy access to the Metra, Green Line, and 63rd/Cottage Grove bus stop. Two units are rented; one is ready for your vision. Schedule your showing today!

Rare mixed-use investment opportunity in the heart of Lakeview. Solid brick building featuring a ground-floor restaurant space with a lease in place through October 2027, providing stable income. The second-floor apartment offers 2 bedrooms, 1 bath, an updated kitchen and bath, spacious living room, and separate dining room. Zoned B1-3, offering long-term redevelopment and value-add potential. Residential tenant is month-to-month. Property is being sold in as-is condition and must be purchased together with 1630 W. Melrose. Excellent opportunity for investors, developers, or owner-users seeking a prime Lincoln Avenue location. Unfinished basement.

33 E Division was originally constructed in 1881. This historic Potter Palmer Greystone sits on a rare 23.5-foot-wide lot - one of the few wider residences built in the Gold Coast during that era. This historic property encompasses over 7,000 square feet across six levels and is currently configured as four income-producing apartments, with a rare four-car tandem garage created from the former fifth apartment and the original one-car garage. Whether maintained as an investment property, transformed into a boutique luxury residence, or restored into a magnificent single-family mansion, the opportunities here are truly endless. Each apartment throughout the building includes soaring 10+ foot ceilings, original millwork, stained glass, hardwood floors, carved oak mantels, and marble fireplaces. Lovingly maintained by the same owner for nearly 50 years, the property has many updates, including windows, electrical, plumbing, HVAC systems, and roof #1: A ground-level studio with a fireplace, generating $2,000 per month. Lease expires 4/30/27 #2: A generously sized bi-level 2-bedroom, 2-bath residence featuring four fireplaces, a formal dining room, a jacuzzi tub, a steam shower, a private deck (20.5 x 8.0), and rare 4-car parking, generating $5,500 per month. Lease expires 4/30/27. #3: A 1-bedroom apartment and fireplace generating $2,500 per month. Lease expires 10/31/26. #4: A large bi-level 3-bedroom residence featuring three fireplaces, a balcony, a jacuzzi tub, a steam shower, and an expansive private rooftop deck (39.9 x 15.10), generating $6,200 per month. Lease expires 7/31/26 Located in the heart of Chicago's prestigious Gold Coast, just steps from the lakefront, Oak Street Beach, the Magnificent Mile with shopping & fine dining, plus designer boutiques on Oak Street. Just moments from Oak Street Beach and Lake Michigan, Michelin-rated dining, world-class shopping, celebrated entertainment, and renowned cultural attractions, this address delivers the very best of Gold Coast living.

Profitable. Turnkey. Sold As-Is.This charming 2019-rehabbed 2-flat offers a fully updated and income-generating opportunity in a well-connected location. Both units are currently rented on month-to-month leases, making this a perfect option for investors seeking flexibility and immediate cash flow. Each unit features cozy bedrooms and bathrooms, beautiful hardwood floors, and a turnkey, move-in ready condition. Recent updates include: Stainless steel appliances Individual forced air furnaces Separate hot water tanks Updated electrical and plumbing Newer windows, roof, and rear porch Located near public transportation and shopping, this building offers convenience and long-term value. Please note: Photos reflect the second-floor unit before and during current tenant occupancy.

Charming Vintage 3-Flat in Rogers Park - Directly Across from Philip Rogers Park Welcome to this timeless gem located in the heart of Rogers Park, one of Chicago's most vibrant and diverse neighborhoods. This vintage 3-flat, situated directly across from the lush and inviting Phillip Rogers Park, offers a perfect combination of classic charm and unbeatable location. Unit 1 (First Floor) is a spacious 2-bedroom + den, 1-bathroom unit featuring flexible living space perfect for a home office, library, or guest room. Units 2 & 3 are both large 2-bedroom, 1-bathroom layouts, offering generous living areas and ample natural light. Shared coin-operated laundry is in the basement. Rents are all below market offering an exceptional opportunity for investors looking for a high-potential rental property or owner-occupants seeking additional rental income.