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

4 Beds ⋅ 3 Baths ⋅ 12748181 MLS ⋅ NEW Status

A statement of contemporary luxury and unsurpassed innovation! Your ELEVATOR opens directly into this 4,330 square foot PENTHOUSE home which is almost 50' wide and boasts 4 bedrooms + family room/2.1 baths which are uniquely centered around a gorgeous light atrium. The PRIVATE ROOF DECK offers 360-degree views, includes a service area with sink and beverage fridge, a built-in grilling station, built-in TV and low maintenance green space which includes trees and an irrigated native garden. The sprawling great room accommodates an oversized living room set and also has a dedicated dining space adjacent to the modern kitchen. The kitchen offers Ernestomeda cabinets, Liebherr & Miele appliances, a large island, appliance garage and an insane WALK-IN PANTRY with a dual zone wine refrigerator with ice maker. Near the kitchen you will also find a wet bar with Euro cave free-standing wine refrigerators & barware storage. The south facing family room has an Eco smart bioethanol fireplace and built-in cabinets, shelves and TV. A king-size primary suite has ELECTRONIC SHADES/DRAPES, a lux walk-in closet by Poliform, a spacious bathroom with Toto plumbing fixtures, Italian porcelain tile, a walk-in shower and private soaking tub for two. Bedrooms 2 and 3 (currently used as a guest room and an office) both easily accommodate queen size beds. The 4th bedroom is currently used as a creative space and open to the kitchen and wet bar but could easily be enclosed. The dreamy LAUNDRY ROOM offers excellent storage and workspace. Abundant light is provided by 2 skylights and floor to ceiling windows. High ceilings (10-11 ft) throughout, CONCRETE FLOOR WITH RADIANT HEAT & 5 ZONES, over $30k in upgraded light fixtures, SAVANT MULTI-ZONE A/V which includes 3 zones of video, 5 zones of audio & MOTORIZED WINDOW TREATMENTS. ASSESSMENTS INCLUDE HEAT & HOT WATER/association has healthy reserves. A+ Roscoe Village location near night life and shopping and in the Audubon School District. 2 car garage parking included. 2025 Taxes:$44,334.75.

2041 W Roscoe Street Unit #PH, Chicago

$1,350,000

5 Beds ⋅ 4 Baths ⋅ 12753253 MLS ⋅ NEW Status

Set on a picturesque, tree-lined street in the sought-after Audubon School District, this beautifully appointed five-bedroom, 3.1-bath Roscoe Village residence delivers exceptional space, timeless character, and an effortless indoor-outdoor lifestyle. An elegant living room with a tray ceiling flows into the formal dining room, while rich hardwood floors, crown molding, custom millwork, and a striking iron-and-wood staircase add architectural distinction throughout. At the rear of the home, the expansive eat-in kitchen has been elevated with Taj Mahal quartzite countertops and backsplash, refinished maple cabinetry, updated hardware, stainless steel appliances, and a double-oven range. The kitchen opens seamlessly to an inviting family room anchored by a beautifully retiled fireplace, creating a sophisticated yet comfortable setting for everyday living and entertaining. French doors extend the space onto a large, sun-filled deck ideal for al fresco dining and relaxed summer gatherings. Three bedrooms occupy the upper level, including a serene primary retreat with soaring vaulted ceilings, skylights, a sleek linear gas fireplace, and a private balcony overlooking the backyard. The fully renovated primary bath offers a spa-like escape with a marble shower, soaking tub, heated porcelain tile floors, dual vanities, and refined lighting. Custom closet organizers, room-darkening shades, and refreshed flooring further enhance the home's comfort and functionality. The finished lower level provides exceptional flexibility with a spacious recreation room, two additional bedrooms, a full bath, and a convenient mudroom. Meticulously maintained and thoughtfully improved, the home also features updated patio doors, newer laundry appliances and water heater, an electric sump pump, recent masonry and tuckpointing, and updated HVAC systems. Complete with three fireplaces, multiple outdoor spaces, and a 2.5-car garage, this sophisticated residence offers gracious city living moments from the acclaimed dining, boutiques, and cafes along Roscoe Street, St. Benedict, the Paulina Brown Line, and near Hamlin Park.

3242 N Leavitt Street, Chicago

$1,150,000

4 Beds ⋅ 5 Baths ⋅ 12743697 MLS ⋅ CONTINGENT Status

Refined, expansive, and exceptionally appointed, this four level Roscoe Village residence delivers a sophisticated urban lifestyle with the scale and comfort of a single family home. Offering approximately 3,400 square feet, 4 bedrooms, and 4.5 baths, the home is designed with elevated finishes, generous proportions, and multiple spaces for both elegant entertaining and effortless everyday living. The chef's kitchen serves as a striking centerpiece with a substantial island, Viking and Fisher & Paykel appliances, limestone backsplash, and abundant prep and storage space. The primary suite feels like a private sanctuary, complete with a fireplace, secluded terrace, and spa inspired bath with separate soaking tub and shower. Two additional bedrooms each offer private ensuite baths, while the lower level provides a beautifully flexible extension of the home with a fourth bedroom, full bath, dry bar, and wine refrigerator. Crowning the residence is an extraordinary approximately 700 square foot private rooftop deck, creating an impressive setting for alfresco dining, summer gatherings, and evenings overlooking the neighborhood. Additional features include a multi zone sound system, dual HVAC, an oversized laundry room with exceptional storage, and garage parking. Ideally positioned within the Audubon Elementary School district and moments from acclaimed Roscoe Village dining, cafes, boutiques, parks, and convenient Brown Line access, this is a distinctive opportunity to enjoy luxury, privacy, and remarkable space in one of Chicago's most coveted neighborhood settings.

2224 W Roscoe Street Unit #A, Chicago

$1,275,000

8 Beds ⋅ 3 Baths ⋅ 12737803 MLS ⋅ CONTINGENT Status

Set on one of Roscoe Village's beautiful tree-lined streets, this extraordinary and rarely available greystone is anything but typical. With a distinctive layout, oversized lot, detached greystone garage, finished studio space, and an abundance of original architectural character, this property offers a level of flexibility that is incredibly hard to find. Located in the highly sought-after Audubon School District, it is an exceptional opportunity for a single family home, owner-occupant investor, or multi-generational household. Owned and lovingly maintained by the same owner for more than 20 years, the main residence encompasses the first and second floors. Each floor features 3 bedrooms, 1 bathroom, a formal living room, formal dining room, and a beautiful custom wood-burning fireplace. Original details throughout the home include rich oak millwork, hardwood flooring, stained-glass accents, oversized windows, and spacious rooms that showcase the scale and craftsmanship of a bygone era. The kitchen was thoughtfully renovated in 2016 and features custom cabinetry, stone countertops, stainless steel appliances, and a large center island that creates an inviting gathering space. The bathroom was updated in 2021, providing a fresh complement to the home's classic architectural details. The garden apartment adds another layer of flexibility and potential. Currently configured as a 2-bedroom, 1-bath residence, it includes a full kitchen, comfortable living space, and excellent storage. The apartment was previously used as a 3-bedroom layout, offering additional possibilities for future use. One of the property's most unusual features is the detached greystone garage. Above the garage, a finished loft currently serves as a fitness studio and is already plumbed for a bathroom. Whether envisioned as a private office, art or creative studio, gym, workshop, guest space, or future finished living area, this bonus space provides tremendous potential. The property also includes a separate carport and an oversized yard with plenty of room for outdoor entertaining, gardening, recreation, or simply enjoying the space. The home's substantial construction is further highlighted by approximately 12-inch-thick limestone walls, reflecting the quality, permanence, and craftsmanship characteristic of Chicago's historic architecture. And the location is hard to beat! Just two blocks south of the popular Roscoe Street corridor, you'll be close to neighborhood restaurants, cafes, parks, boutique shopping, and everyday conveniences, while still enjoying the peaceful residential atmosphere of this sought-after pocket of Roscoe Village. Properties with this combination of architectural character, scale, outdoor space, additional living space, and flexibility rarely come to market. A truly special opportunity to own a distinctive piece of Roscoe Village with the potential to adapt to a variety of lifestyles and investment strategies.

3248 N Oakley Avenue, Chicago

$1,700,000

4 Beds ⋅ 4 Baths ⋅ 12731614 MLS ⋅ ACTIVE Status

An exceptional residence in the award winning and highly sought after Audubon school district in the heart of Roscoe Village. This home blends sophisticated design with timeless architecture and effortless everyday living. Tons of natural light, an extraordinary blend of luxury finishes, thoughtful functionality and beautifully designed indoor and outdoor living spaces complete the home. Other features include rich hardwood flooring, abundant storage and designer lighting to create a warm yet elevated atmosphere. Designed for both entertaining and intimate gatherings, the expansive main level connects the living and dining rooms to a wonderful chef's kitchen with premium appliances, an oversized island, separate beverage fridge and abundant cabinetry. The family room with custom stone leads seamlessly to a large, maintenance-free rear deck oasis offering the perfect setting for outdoor dining, lounging or enjoying warm summer and fall evenings. The thoughtfully designed floor plan offers four spacious bedrooms all on the upper level and three and a half beautifully appointed bathrooms. The primary bedroom features a luxury new bathroom with separate tub and shower, massive primary walk-in closet, elegant hardware, laundry and bay window with reading nook. The spacious attic level features an additional family room and home office with a full bathroom ideal for a guest or in-law suite, fitness studio, or recreation space. The versatile basement level features an additional full-size laundry, abundant additional storage, a mudroom and space for a workshop. The home's location is perfectly situated steps from multiple highly regarded Roscoe Village restaurants, boutique shops and cafes, the 312 RiverRun biking and walking trail, Depaul College Prep, Lane Tech and Hamlin Park with its pool, tennis courts, athletic fields, and community center. It is walking distance to the Brown line, Southport Corridor, Wrigley Field and Revere Park with additional athletic fields, tennis courts, pickle ball, running paths and soccer fields.

2215 W Roscoe Street, Chicago

$1,350,000

12723814 MLS ⋅ PENDING Status

A distinctive 1890s corner property offering historic character, versatile residential layouts, and an attractive multi-unit investment opportunity. Originally built as a neighborhood tavern, the building has since been converted to five apartments, along with a sixth non-conforming unit. The residences vary in layout and finish, showcasing hardwood flooring, tall ceilings, oversized windows, classic bay spaces, paneled doors, decorative trim, and abundant natural light. Several units feature spacious living and dining areas, eat-in kitchens, generous storage, ceiling fans, and in-unit laundry, while the upper-level residence offers charming sloped ceilings and skylights. Kitchens and baths reflect a mix of classic and updated finishes throughout. The prominent turret and multiple bay windows create memorable curb appeal. Additional features include separate heating systems, tenant-paid utilities, and a detached lofted two-car garage. Set in the heart of Roscoe Village, the property is surrounded by neighborhood restaurants, cafes, independent shops, and entertainment along Roscoe Street and Lincoln Avenue. Fellger Park and amenity-rich Hamlin Park are nearby, with convenient access to the Addison and Paulina Brown Line stations, the Damen and Addison bus routes, Wrigleyville attractions, and the Belmont Theater District. Seller and broker make no representation regarding the legality or permissible use of the sixth unit.

3501 N Damen Avenue, Chicago

$1,999,999

8 Beds ⋅ 5 Baths ⋅ 12718116 MLS ⋅ PRICE CHANGE Status

Huge price improvement on this beauty! Imposing, all brick, newer construction 3+ unit building in Roscoe Village in one of the best locations in the city and within walking distance to the train station. The first 3 floors are identical layout 2 bdrms 1 bath with large rooms and tandem rear enclosed sun rooms. The top floor (attic) and the basements are set up as 1 bdrm 1 bath, each unit has a kitchenette or kitchen. FIVE total floors of living space that can be used for a large/extended multi-generation family, can be rented individually, or used as short term stay. The building could also be de-converted and made into a single family house. All of these possibilities could fit multiple plans currently or for near future, unlike with a SF house. Rarely-found feature: the 2nd floor of the garage has a heated pool for year-round enjoyment!!

1942 W Melrose Street, Chicago

$6,500,000

5 Beds ⋅ 6 Baths ⋅ 12719016 MLS ⋅ ACTIVE Status

Situated in the absolute heart of Roscoe Village, this distinguished corner church has been spectacularly converted into a sprawling single-family estate. The handsome red-brick building spans over two city lots and offers approximately 10,000 square feet of magnificent living space. Despite its grand scale, the home is designed to feel remarkably private and surprisingly intimate. The property features 5 bedrooms, 4 full baths, 2 half baths, and 2 kitchens. The definitive highlight is the former nave, transformed into one of the most spectacular living rooms in Chicago, complete with 25-foot vaulted ceilings and original beams and woodwork. Natural light fills the room, filtered by the breathtaking restored stained glass windows. New herringbone quarter sawn oak floors are stunning throughout. The striking bell tower is accessible via an interior staircase that provides sweeping neighborhood views. The main level kitchen features a mix of new and retrofitted antique cabinetry, chef's appliances, and abundant storage. The dining room opens to a private rooftop terrace tucked nicely behind the crenellated parapet wall. Three guest bedrooms are located in their own wing; one en-suite and the other two sharing a bathroom. One of the bedrooms, currently configured as an office, features a breathtaking fireplace. Rooms are spacious and private, offering fantastic natural light. The primary suite is sprawling with vaulted ceilings, multiple sitting areas, 2 large walk-in closets, a laundry setup, and a large bathroom with a separate tub and shower. It's truly a home within a home. The lower level offers a massive family room with a wet bar, catering kitchen, and mud room leading to the attached two-car garage. There is also a large gallery leading to the guest suite, which has an en-suite bathroom and separate entrance, making it the perfect private retreat. Several efficient mechanical systems keep the house comfortable year round including sub-slab radiant heat and beautiful historical radiators. The well-planned systems create a living environment that is both comfortable and efficient. The location is perfect, just steps to Roscoe Village dining and shopping along Damen, Lincoln, and Roscoe. Located in the Audubon school district and just steps to the Paulina Brown Line station.

1901 W Cornelia Avenue, Chicago

$1,250,000

5 Beds ⋅ 4 Baths ⋅ 12711940 MLS ⋅ CONTINGENT 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

$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

$1,099,000

12596504 MLS ⋅ ACTIVE Status

Buyer's finance fell through. 4 Mixed-Use Units 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. 2014 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 Downtown Chicago. Real estate taxes are under contest with county and expected to be at $20,000 level. Property was leased out to 1-single tenant till May 31, 2026, with monthly lease amount of $9,000. Value of lease should be around $11,000 per month for all building.

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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