luxury properties for sale Chicago, United States

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.

Excellent opportunity in West Rogers Park. Classic 3-bedroom, 1.5-bath colonial home situated on a corner lot. Lovingly cared for over the years, this home offers warmth and character. The first floor features a living room with woodburning fireplace and hardwood floors. The adjacent, paneled den makes a great home office. The separate, spacious dining room is perfect for hosting gatherings. The eat-in kitchen overlooks the large fenced yard with 2-car garage. Upstairs, there are three large bedrooms and one full bath. Generous closets and hardwood floors throughout the 2nd floor. The basement has a rec room with fireplace, and a spacious utility/laundry room that is plumbed for a bath. This is a rare opportunity to update or expand this well-loved home which is being sold as is.

Perfect updated 2 flat on a tree lined street in the heart of Andersonville! Top floor unit was completely reconfigured and renovated by the current owner to include a massive sun filled great room, 2 beds, and 2 baths. Stunning custom kitchen with stainless appliances, great storage, and additional dry bar! Top floor has newer HVAC, In Unit Laundry and hardwood flooring throughout! Primary suite with dressing area and ensuite bath featuring oversized vanity, and huge walk in shower with glass surround! First floor 2 bed plus den, 1.1 bath unit with generous public rooms, kitchen with great storage and stainless appliances, opens to eating area/ sitting room. First floor unit also has central HVAC, and private laundry in the basement. Enclosed rear stairs to great landscaped yard! 1.5 car garage with plenty of space for a 2 car garage if needed. Extensively updated and well maintained by the current owner, the building provides a unique and flexible asset with room for considerable upside with full basement! Seconds to the best of Clark Street restaurants , and transportation including Metra! Must See!

Excellent investment opportunity in the heart of Tri-Taylor. This updated legal three-flat is ideally located near the Illinois Medical District, UIC, the Blue Line, I-290, Little Italy, Cinespace Studios and numerous neighborhood developments. The building offers three spacious residences: a 3-bedroom garden unit, a 2-bedroom first-floor unit and a 4-bedroom second-floor unit. Each residence features central HVAC, private laundry, stainless steel appliances, a dishwasher and garbage disposal. All units are currently rented below market, offering meaningful upside. Significant recent improvements include all-new electrical wiring throughout the building, new water heaters in Units B and 1, and a new A/C system serving Unit 2. Additional updates include new flooring and a new dishwasher in Unit 2, fresh paint throughout all three residences, and extensive improvements to the rear exterior wall, including new siding, structural support, plywood, moisture barrier and insulation. The property also features a two-car garage with additional storage, fenced front and rear yards, a shared patio and a new walkway connecting the alley entrance to the rear outdoor space. With substantial recent capital improvements, under-market rents and strong demand driven by nearby universities, hospitals, transportation and employment centers, this is an attractive opportunity for an investor or owner-occupant.

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.

Excellent investment opportunity in a desirable Northwest Chicago neighborhood. This fully leased, well-maintained building generates $3,500 per month in gross rental income ($42,000 annually), with an estimated net operating income of $26,613.52 and a current cap rate of approximately 5.91%. With only a modest 10% increase in rents, the cap rate would exceed 6.5%, presenting strong upside potential. Additional income is generated from the basement coin laundry (one washer and one dryer), producing approximately $400-$500 annually. Recent improvements include a new roof (2019), new front porch (2019), garden unit remodeled (2018), and Unit 1 remodeled (2020). The property features hardwood floors in the first and second floor units, separate furnaces, and separate electric meters. Units #1 and #2 have tenants paying all utilities, while utilities are included in the rent for the garden unit. The building is fully rented with well-screened, reliable tenants, and units are clean and well-maintained. Additional highlights include easy street parking, outdoor storage sheds, a large fenced yard with a concrete patio, and coin laundry in the basement for supplemental income. Seller makes no representation regarding the legality of the third (garden) unit.

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.