Browse All Roscoe Village IL Above $1M Properties for Sale

5 Beds ⋅ 4 Baths ⋅ 12711940 MLS ⋅ NEW Status

This is a rare opportunity to own a legal 3-unit building in the heart of Roscoe Village. Featuring a stately facade and impressive curb appeal, the property sits on a beautiful, tree-lined block in one of Chicago's most desirable neighborhoods-offering the perfect blend of stability and upside for investors or owner-occupants alike. Each unit offers a well-designed layout with in-unit washer and dryer, individual heating and cooling expenses, separate hot water tanks, and private outdoor space-highly desirable features that attract and retain quality tenants. The building is consistently easy to rent, with thoughtfully structured leases that include detailed riders and built-in rent increases. As leases turn over, there is additional opportunity to further enhance income, as they are currently rented below market value. Rents listed are estimated market values. Current rents are $2695 for unit 1, $2375 for unit 2 including parking, and $2790 for unit 3, plus $165/month for the additional parking spot. The property also includes a backyard and a 2-car garage. For those seeking an owner-occupied option, the unique two-level top-floor unit presents an exceptional opportunity to live comfortably while generating income below.

1742 W School Street, Chicago

$1,749,900

4 Beds ⋅ 5 Baths ⋅ 12694737 MLS ⋅ ACTIVE Status

A rare opportunity to own an essentially new-construction single-family home within the timeless framework of a classic Chicago masonry residence, perfectly positioned on one of Roscoe Village's most desirable blocks in the Audubon School District. This move-in-ready luxury gut renovation offers five bedrooms, multiple outdoor spaces, a three-car heated garage, and the rare combination of classic architectural character with the comfort, efficiency, and polish today's buyers expect from new construction. The design language throughout the home is elevated yet welcoming, balancing clean modern lines with warm natural textures and carefully selected architectural details. Rich wood cabinetry, refined lighting, crisp white millwork, and beautifully layered finishes create a sense of cohesion from room to room. Even the smaller spaces have been treated with intention, including the jewel-box powder room, where designer wallpaper, paneled wainscoting, a floating wood vanity, brass fixtures, and curated accents bring personality, charm, and sophistication. Every element has been chosen to feel fresh, functional, and enduring - a home that is not only visually striking, but thoughtfully designed for the way people truly live. At the heart of the home, a stunning chef's kitchen makes an immediate impression with custom Allure cabinetry, premium Thermador appliances, dramatic quartz surfaces, and an oversized waterfall island with microwave drawer. Designed to be as functional as it is beautiful, the kitchen offers generous prep space, abundant storage, elegant brass hardware, and seamless connection to the open-concept living and dining areas. The second level features three spacious bedrooms, including a beautifully appointed en-suite bedroom ideal as a secondary primary suite, guest suite, or flexible bedroom suite, along with a convenient second-floor laundry room. Occupying the entire third level, the private primary retreat features multiple professionally organized closets, a secluded rooftop terrace, and a spa-inspired bath with radiant heated floors, dual vanities, illuminated mirrors, and a luxurious wet room. The finished lower level adds exceptional versatility with a spacious family room, fifth bedroom, full bath, second laundry area, and private sauna for an elevated at-home wellness experience. Additional highlights include a complete gut renovation, new electric, plumbing, roof, windows, insulation, dual-zoned HVAC, radiant heated bathroom floors, professionally organized closets throughout all five bedrooms, two laundry areas, designer finishes, and exceptional storage. Outdoor living is equally impressive with multiple decks, landscaped front and rear yards, custom paver patios and walkways, a cedar-and-iron fenced yard, and an expansive rooftop deck with pergola above the three-car masonry heated-garage. Moments from neighborhood restaurants, boutiques, parks, grocery stores, and highly regarded schools including Audubon Elementary, Lane Tech, and DePaul College Prep, this turnkey residence delivers space, style, location, and peace of mind in one extraordinary Roscoe Village home.

3414 N Hamilton Avenue, Chicago

$1,390,000

4 Beds ⋅ 4 Baths ⋅ 12707196 MLS ⋅ CONTINGENT Status ⋅ Addison Court BLDG.

Exceptional 4-bedroom, 3.1-bath duplex in a boutique all-brick building in the heart of Roscoe Village, offering the comfort and scale of a single-family home with elevated newly-constructed design. The expansive main level features a chef's kitchen with a 10-foot quartz island, integrated Thermador appliances, custom cabinetry, white oak hardwood floors, coffered ceilings, designer lighting, a gas fireplace, and a sophisticated dry bar. The spacious family room opens to a stunning 300 SQUARE FOOT covered terrace complete with a masonry fireplace, for seamless indoor-outdoor living year-round. Radiant heated floors throughout the bedroom level complete with three ensuite bedrooms and a luxurious primary suite with dual walk-in closets and a spa-inspired bath featuring a steam shower, freestanding soaking tub, and designer finishes. Additional outdoor spaces include a private patio and rooftop deck, plus attached garage parking. Located in the highly sought-after Audubon School District and just steps from the Brown Line, parks, shopping, and dining, this turnkey residence delivers luxury living in one of Roscoe Village's most coveted locations. Don't miss your opportunity to see this masterpiece!

2254 W Roscoe Street Unit #1, Chicago

$2,675,000

6 Beds ⋅ 6 Baths ⋅ 12688427 MLS ⋅ PENDING Status

Spectacular new construction single-family home on an EXTRA WIDE (27 1/2 - foot) LOT by acclaimed developer, Thady Construction. Tucked along a quiet stretch of Newport that gently dead-ends into Ravenswood Avenue, the setting offers a rare sense of privacy and calm just steps from Roscoe Village. A tastefully designed exterior combining masonry and Hardie Board creates both an impressive and welcoming presence on this tree-lined street. A formal foyer welcomes guests into a thoughtfully designed main level featuring an elegant living room with fireplace alongside a sophisticated dining room, both enhanced by distinctive archways that subtly define each space. Entertaining is made easy with the inclusion of both butler and walk-in pantries connecting the dining room to the kitchen. Thanks to the extra width, the kitchen is truly exceptional and includes a genuine eat-in area. Kitchen features include extensive custom cabinetry, SubZero, Wolf, and Bosch appliances, natural stone counters and backsplash, and under-cabinet lighting. The great room is an expansive 20 x 18 and showcases ceiling beams, a gas fireplace with stone surround, custom cabinetry, and a smartly positioned powder room completing the main level. At the rear of the home is a stunning grade-level mudroom atrium with 15-foot ceilings, stone flooring, and custom cabinetry for day-to-day storage. Ascend to the bedroom level where you'll find four bedrooms, three full bathrooms, and an oversized laundry center. The primary suite features a bedroom with 12-foot vaulted ceilings and a sprawling 26-foot-long walk-in closet and dressing area. The primary bath also boasts vaulted ceilings, radiant heated floors, double vanities, a soaking tub, and a steam shower with rain and hand-held shower fixtures. The radiant-heated lower level is remarkable for its sheer scale, beginning with a 24 x 20 recreation room complete with wet bar and beverage center. Also on this floor are two additional large bedrooms, a full bath with en-suite access, second laundry area, powder room, and an enormous storage room. The garage features a rooftop deck finished with 24" x 24" porcelain tiles, along with a second overhead door that opens directly to the backyard - ideal for outdoor entertaining, moving large items in and out of the home, or providing a caterer staging space for larger gatherings. Additional notable features include snow-melt front steps and rear walkway. Conveniently located just a short walk to Roscoe Village, Hamlin Park, Fellger Park, and the Brown Line. Delivery Summer 2026.

1841 W Newport Avenue, Chicago

$1,650,000

4 Beds ⋅ 4 Baths ⋅ 12687683 MLS ⋅ PENDING Status

Tucked onto one of Roscoe Village's most welcoming tree-lined streets, this beautifully updated single-family home delivers four bedrooms, three full and one half bath, and approximately 3,250 square feet across three thoughtfully designed levels. Oversized east-facing windows fill the open main level with natural morning light. At its center is a refreshed kitchen built for both everyday cooking and easy entertaining, featuring quartz countertops, a chef-quality range and hood, and a 36-inch refrigerator-freezer. The kitchen flows into a comfortable family room, while a separate living room with fireplace and a dedicated dining area complete the level, along with a convenient powder room. Professionally refinished hardwood floors run throughout the main living spaces, and brand-new neutral carpet and padding add warmth and comfort underfoot. Upstairs, the primary suite features a vaulted ceiling, a spa-inspired bath with a soaking tub and separate glass shower & bench, and a walk-in closet. Two additional bedrooms and a fully remodeled bath complete the upper level. The lower level expands the living space with an oversized recreation room anchored by a fireplace, ready to serve as a media room, home gym, home office, or play space, plus a fourth bedroom, a full bath, and a dedicated laundry room. Outdoor living is just as considered. Custom front-and-back landscaping frames a refinished front porch with beautiful curb appeal, a composite rear deck with pergola and string lights with hydrangeas in bloom, and a bluestone patio designed for warm-weather gatherings. A two-car garage off the alley completes the property. Ideally located near the Paulina Brown Line station, the shops and restaurants of Roscoe Village, neighborhood parks, and everyday conveniences, this home delivers turnkey city living with genuine neighborhood character.

1815 W School Street, Chicago

$1,400,000

3 Beds ⋅ 3 Baths ⋅ 12686992 MLS ⋅ CONTINGENT Status

You don't want to miss this lovely home located in the core of Roscoe Village! Lots of charm, from the grand front porch with swing to the bright interior with floor to ceiling windows and natural light-this is a special place! Many renovations from 2023 include a Chef's kitchen w ss appliance, quartz countertops, pantry, wine chiller and tons of storage. The open floor plan includes custom-milled columns, hardwoods throughout, a formal living space in front next to a formal dining room with a lovely designer wall covering & lighted tray ceiling. A relaxing family room with marble surround fireplace leads to a new large deck, lovely yard, and rooftop (additional) deck above the garage! An entertainer's dream! A half bath is also tucked neatly next to the kitchen. The Master Suite is huge and includes a vaulted ceiling, floor to ceiling windows, and another working gas fireplace, large Walk-in closet and remodeled bath. Two additional bedrooms and an additional fully renovated bath are also located on the2'nd level, one of which has a vaulted 2'nd level- perfect for a teen! All bedrooms have new hardwoods installed in 2023. The lower level is finished and affords space for a +1 bedroom, office, work out area, and a separate enclosed laundry room. Two car garage on site. This home's location is Bullseye to all the shops, restaurants & boutiques being just 2 blocks from Roscoe & Damen on a lovely one-way side street. All offers will be evaluated on Sunday and responded to on Monday, June 29th. Preferred closing date is September 4th, 2026. Sellers are offering a $500. credit toward a home warranty by Assurant Home Warranty.

1933 W School Street, Chicago

$2,850,000

12684987 MLS ⋅ ACTIVE Status

Fully renovated 6-unit mixed-use building located in the highly desirable Roscoe Village neighborhood. The property underwent a complete gut renovation and reconfiguration in 2020, creating modern layouts with king-sized bedrooms, added closet space, and sleek contemporary finishes throughout. Designed for low maintenance and strong tenant appeal, the building offers a stable monthly rent roll exceeding $18,000. The property also includes a long-term commercial tenant with a national presence, providing additional income stability. A turnkey investment opportunity in a high-demand North Side location with strong income and minimal capital needs.

2120 W Belmont Avenue, Chicago

$1,100,000

7 Beds ⋅ 5 Baths ⋅ 12672659 MLS ⋅ PENDING Status

Classic Roscoe Village legal two-flat with additional third-floor in-law/flex space, offering exceptional versatility for investors, owner-occupants, or those considering a single-family conversion. The owner's duplex-down residence features 4 bedrooms and 3 bathrooms and offers an open-concept kitchen and family room, a separate formal dining room, and multiple living and entertaining spaces highlighted by a cozy fireplace. The spacious kitchen includes abundant cabinetry, granite countertops, a center island, walk-in pantry, and additional space ideal for casual dining, a playroom, or den. Generously sized bedrooms provide ample closet space, complemented by additional storage throughout the home, and a full-size in-unit washer and dryer. . The bright and well-maintained second-floor unit offers 2 bedrooms and 1 bathroom, an additional bonus room, and is currently leased, providing immediate rental income. The unit features an updated kitchen with quartz countertops and an island, as well as an updated bath and a full-size in-unit washer and dryer . Water and garbage included in the monthly rent. In addition to the legal two-flat configuration, the property includes a finished third-floor non-conforming in-law/flex space with three rooms, separate front and rear access, and a refrigerator only (no other kitchen appliances). The space offers flexibility for extended living, workspace, guest accommodations, or future rental potential. Buyers should conduct their own due diligence regarding permitted uses. Additional features include a rear deck, large private backyard, and a two-car detached garage. Located on a quiet, tree-lined street within the highly regarded Audubon School attendance area, this property is an easy walk to the 77 bus and Brown Line stations at Paulina, Addison, and Southport. Enjoy convenient access to Roscoe Village dining, coffee shops, boutiques, neighborhood events, the Southport Corridor, Wrigleyville, and North Center amenities. Rare opportunity to own a legal two-flat with additional finished in-law/flex space in one of Chicago's most desirable neighborhoods.

2245 W Melrose Street, Chicago

$1,000,000

6 Beds ⋅ 3 Baths ⋅ 12663814 MLS ⋅ CONTINGENT Status

Classic 1922 brick 3-flat in the heart of Roscoe Village. Property features three well-maintained units. 1st and 2nd-floor units are with 2 bedrooms plus an additional office/den space. 3rd-floor unit is with 2 bedrooms. All units feature original hardwood floors in living areas and bedrooms. Significant mechanical updates include a new 2025 furnace for the 1st-floor unit, three newer hot water heaters, and window replacements throughout the building all within the last 10 years. Units are separately metered for utilities. Features forced-air heat throughout, window A/C (1st/2nd floor), and central A/C (3rd floor). Basement includes individual water heaters and shared laundry. Prime location steps to Hamlin Park, local retail & dining along Roscoe, and the Paulina Brown Line 'El' station. Property will be entirely vacant at time of closing. Ideal for owner-occupants, developers or investors alike.

3438 N Seeley Avenue, Chicago

$1,099,000

12596504 MLS ⋅ CONTINGENT Status

Income producing 4-Units Mixed-Use property including a coach house in the back. Rosco Village, North Center, and Lakeview neighborhoods. Street level office/retail space, with 2nd and 3rd levels each unit 3-bedrooms, 2-baths and rear coach house. 2018 updates, a great location with everything out the door, multiple bus liens, shops, bakeries, restaurants, easy public transit, street parking, festivals, Walking distance to Fellger Park, Hamlin Park, fieldhouse, pool, and sports facilities, Belmont and Damen's restaurants, shops, vibrant entertainment and minutes from Lincoln Ave., Whole Foods, Jewel, Mariano's, and Costco. Audubon Elementary District. Easy access to major roads, I-90/I-94, and minutes to Downton Chicgao.

2310 W Belmont Avenue, Chicago

$1,749,000

12522923 MLS ⋅ ACTIVE Status

WOW!....ROSCOE VILLAGE (4) STAR LOCATION ON THE ROSCOE STREET STRIP! A RENOVATED (6) UNIT VINTAGE BRICK CONSTRUCTED (3) STORY MIXED-USE BUILDING WITH (1) COMMERCIAL RETAIL STOREFRONT WITH (5) RESIDENTIAL RENTAL UNITS. (5-6) PARKING SPACES & A SIDE YARD! ALL RENTALS ARE (2BR-1BATH) UNITS WITH SEPARATE HEAT & HOT/W TANKS. IN ADDITION TO A FULLY OCCUPIED BLDG. THERE IS ADDITIONAL INCOME FROM THE WEST EXPOSURE BILLBOARD/SIGNAGE. SOON A PROPOSED & PENDING CELL TOWER LEASE ADDING $2,000 PER MONTH! A FULL UNFINISHED BASEMENT HAS POTENTIAL FOR OTHER USES. ALL THIS ON A SITE OF (37.5) FOOT WIDE LOT THAT COULD BE USED FOR ADDITIONAL PARKING AND/OR A SIDE YARD WITH COMMERCIAL POTENTIAL CAFE/DINING! COIN LAUNDRY IN BASEMENT ADDS ADDITIONAL INCOME. (GRM) IS EST. PROFORMA AT FULL MARKET RENTS DUE TO LONG TERM TENANTS & FAMILY.

1953 W Roscoe Street, Chicago

$1,750,000

5 Beds ⋅ 5 Baths ⋅ 12462111 MLS ⋅ PENDING Status

2237 W Roscoe Street Unit #2W, Chicago

$1,675,000

4 Beds ⋅ 6 Baths ⋅ 12269352 MLS ⋅ CONTINGENT Status

This preconstruction single-family home offers a luxurious living experience in the sought-after Roscoe Village neighborhood of Chicago. With 6 bedrooms and 4.2 baths, this stunning property spans over 4,200 square feet across three levels, showcasing exceptional architecture and craftsmanship. Upon entering, you'll be greeted by a beautiful foyer leading to a formal living and dining room, creating an ideal space for entertaining. The kitchen is a chef's dream, featuring custom cabinetry. The finished basement includes a family room, a half bath, and two additional bedrooms, one with an ensuite full bathroom. Upstairs, you'll find four bedrooms filled with natural light and exquisite finishes. The primary suite is a highlight, offering a spa-like bathroom and expansive custom walk-in closets. The home is complete with a 2-car garage, with a private rooftop deck, and professional landscaping, making it the epitome of luxury living.

1743 W Newport Avenue, Chicago

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