Browse All Roscoe Village IL Historical Properties for Sale

2 Beds ⋅ 2 Baths ⋅ 12752831 MLS ⋅ NEW Status

Gorgeous and spacious 2BD/2BA loft in the heart of Roscoe Village. Freshly painted with towering 14-foot ceilings and South and West facing windows that provide maximum sunlight throughout the day. An expansive, open-concept kitchen features granite countertops, Bosch dishwasher and in-unit washer and dryer as well as a long breakfast bar island for extra counter space or entertaining. A separate dining area connects the kitchen to the massive living room, creating perfect flow for parties and family gatherings. The primary bedroom fits a king-size bed and features a walk-in closet, ensuite bathroom and extra lofted storage space above the bathroom. The generously sized second bedroom easily accommodates a queen-sized bed and features built-out closets and more lofted storage space. The Old Pencil Lofts Building is well managed with healthy reserves, a state of the art security system, package delivery room, modern gym, laundry room, party room, elegant courtyard for grilling and outdoor gatherings and a rooftop deck with one of the best views in the entire city. Very pet friendly, with no rental restrictions except for a 6 month minimum on leases. One heated & deeded garage space and an extra storage locker are included in the purchase price.

1800 W Roscoe Street Unit #521, Chicago

$950,000

4 Beds ⋅ 3 Baths ⋅ 12741684 MLS ⋅ CONTINGENT Status

Jazzy 2 flat with owner's duplex up and simplex rental on 1. Street is full of high-end homes. Outdoor space is fantastic. The garage has loft space. Smart real estate on all levels. Plenty of room to move laundry to each unit out of the basement. ADU additions are very possible at this address. SFR conversion is also a likely option.

3307 N Oakley Avenue, Chicago

$250,000

1 Beds ⋅ 1 Baths ⋅ 12742465 MLS ⋅ CONTINGENT Status

Tucked behind a secure, beautifully landscaped courtyard in the heart of Roscoe Village, this bright 1-bedroom condo offers an inviting retreat in one of Chicago's most walkable neighborhood settings. East and west exposures bring in abundant natural light, while freshly painted interiors and beautifully sanded and refinished hardwood floors create a warm, polished feel throughout. The kitchen features granite countertops, stainless steel appliances, maple cabinetry, built-in storage and a refrigerator replaced in 2023. The spacious bedroom easily accommodates a king-size bed and offers an oversized closet, while the limestone bath includes a soaking tub/shower combination and built-in medicine cabinet. In-unit laundry, with the dryer serviced and internal components replaced in 2026, and central air provide everyday conveniences that are especially hard to find at this price point. Step outside and everything Roscoe Village is loved for is close at hand. Enjoy neighborhood restaurants, coffee shops, grocery stores, boutiques and parks all within walking distance, along with convenient access to the Paulina and Addison Brown Line stations. The landscaped courtyard offers its own extension of the living space-perfect for relaxing outdoors, enjoying warmer weather or even catching the sounds of the neighborhood's annual street festival. Pet-friendly and ideally positioned near Hamlin Park and the shops and dining along Roscoe and Damen, this is an effortless way to enjoy the best of city living with a quieter residential feel. Recent building improvements include a new hot water tank in 2019, hot water boiler replacement in 2022, and parapet wall and masonry repairs completed in 2025.

3406 N Bell Avenue Unit #2, Chicago

$630,000

3 Beds ⋅ 3 Baths ⋅ 12737395 MLS ⋅ ACTIVE Status

Welcome to this stunning, sun-filled 3-bedroom, 2.1-bath duplex-up offering incredible natural light, soaring vaulted ceilings and an open, airy layout in an intimate 6-unit brick building in the heart of Lakeview. The main level features a spacious kitchen with stainless steel appliances, granite countertops, island and breakfast bar overlooking the generous living and dining space with fireplace-perfect for both everyday living and entertaining. A third bedroom and powder room complete the main level. Upstairs, the oversized primary suite features excellent closet space and a beautifully updated private bath. The second upstairs bedroom is also en suite with its own updated full bath. Both full bathrooms were renovated in 2022. Hardwood floors, skylights, custom window treatments and lighting add to the home's character, while the dedicated in-unit laundry room with utility sink provides everyday convenience. Major improvements include a new hot water heater in 2023 and building roof in 2024. Attached garage parking, a huge private storage room and access to the building's large common rooftop deck are all included. Tucked away from Lincoln Avenue with no neighbors living directly above or below, this home offers a surprisingly quiet retreat while putting the best of Lakeview right outside your door. Prime location with neighborhood coffee shops, restaurants, shopping, parks, fitness studios and the CTA right outside your door. An incredible combination of space, light, privacy, updates and location in one of Chicago's most sought-after neighborhoods!

3250 N Lincoln Avenue Unit #C, 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

$750,000

12730514 MLS ⋅ ACTIVE Status

Fantastic investment opportunity in Roscoe Village! This three-unit building offers a classic Chicago neighborhood saloon/store front which is connected to a full, unfinished basement. The 4am liquor license is not transferrable, but the alderman's office supports a 2am liquor license in this location. Please note there is no kitchen in the commercial space currently but could be added. The second story is a two-bedroom/one bath apartment which is rented for $1,275 and has a 60-day kick-out clause. There bar and apartment have shared laundry in the basement. The 2 bedroom/2 bath detached coach house is rented through 7/31/27 for $2,900. It has a wide-open main living level with space for lounging and dining plus a full bath and office nook. Upstairs boasts two bedrooms and a full bath, vaulted ceilings, skylights and good closet space and the unfinished basement offers lots of storage, laundry and the mechanicals. A sign on the side of the building brings in additional $250 per month. Please note, there is no parking on site. 24x100 lot. C1-2 zoning. Agent owned.

3243 N Western Avenue, 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

$949,000

3 Beds ⋅ 3 Baths ⋅ 12729705 MLS ⋅ CONTINGENT Status

This one-of-a-kind Roscoe Village gem offers the rare opportunity to enjoy a free- standing townhome that truly lives like a single-family home, all within the highly sought after Audubon School district and the added benefit of no monthly assessments. Beyond the home itself, the location is truly special - situated on a fun, family-friendly block where neighbors know one another and a legendary annual summer block party has been bringing the community together for more than 30 years. The classic all brick home has a charming private front staircase leading you into the stunning sun-drenched open floor plan defined by original exposed brick, soaring 10-foot ceilings, and gleaming hardwood floors. The main level is designed for effortless hosting, featuring dedicated spacious living and dining rooms, a convenient powder room, and a chef's kitchen equipped with stainless steel appliances, a five-burner stove, granite countertops, and a large breakfast bar island. Immediately off the kitchen is a massive deck perfect for al fresco dining, Summer fun and outdoor entertaining. The character continues upstairs, where you'll find an extra large family room accented by more exposed brick, skylights, and a fireplace-the perfect spot to unwind or entertain the kids. This level also hosts the primary suite, complete with a thoughtfully redesigned ensuite bathroom featuring radiant heated floors, quartz vanity, and a gleaming frameless glass shower. An extra wide staircase leads to the top floor, which houses two additional spacious bedrooms with vaulted ceilings, fantastic closet space, the 2nd well-appointed full bathroom, and private balcony. Natural light pours into every corner of the home through large windows with tree-line views, open exposures, and oversized skylights. Practicality meets comfort with dual-zone HVAC and 2nd floor laundry. Completing this truly amazing space is an unfinished basement that provides incredible storage and a second laundry area. A true masterpiece only steps to the trendy Roscoe Village Strip and easy access to Mariano's, Brown-Line L and the newly refinished Hamlin Park. Rear of the property has another stand alone home and both share a large deck ideal for entertaining! Garage is also shared with 1 space included. Incredible opportunity to get into this sought-after neighborhood and school district.

2307 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

$949,000

3 Beds ⋅ 3 Baths ⋅ 12723046 MLS ⋅ CONTINGENT Status

2307 W Melrose Street Unit #F, Chicago

$799,000

4 Beds ⋅ 2 Baths ⋅ 12720290 MLS ⋅ CONTINGENT Status

Rare opportunity in highly sought-after Roscoe Village on an oversized 32.5-foot lot, just steps from top-rated Hamilton Elementary School. Surrounded by attractive homes and located in one of Chicago's most desirable neighborhoods, this property presents an exceptional opportunity for those looking to customize an existing residence or explore redevelopment possibilities. Adjacent to the EL tracks and bordering a 50 X 124.3 lot CTA, utilization rights make your green space expansive and perfect for entertaining. Rehabbers, developers, and investors are able to transform this 4-bedroom, 2-bath single-family home, offering exceptional potential for renovation, expansion, or redevelopment. The existing home features a spacious layout with separate living and dining rooms, a rear primary suite addition with fireplace, Juliet balcony, and two (2) large walk-in closets, plus three additional bedrooms upstairs. The partially finished basement includes a rec area, workshop space, storage, and laundry/mechanical room. A rare oversized three-car detached garage adds tremendous value and flexibility. Large lot dimensions, strong location, and solid existing footprint create numerous options for the next owner. Bring your vision and unlock the full potential of this Roscoe Village property!

1819 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

$429,000

1 Beds ⋅ 2 Baths ⋅ 12700460 MLS ⋅ ACTIVE Status ⋅ Gallery Lofts BLDG.

Welcome to your dream home at Lakeview's highly coveted Lofts. This beautiful sun-drenched 1 bedroom 1 and 1/2 bath condo redefines loft living with high-end luxury and unbeatable convenience. Completely remodeled in 2020, this stunning residence is move-in ready. This home offers a 27' x 28' primary living space with an open concept kitchen, 11 foot ceilings, 18" crown molding, hardwood flooring, Sub-Zero refrigerator, built in Bosch dishwasher, under-counter microwave stove/oven, custom Omega cabinetry, marble countertops, walk in shower, with rainfall head. This pet friendly home is one block from the brown line and walking distance from Whole foods, Starbucks, Target, the UPS store and the public library. Don't miss out on this great opportunity.

3323 N Paulina Street Unit #3F, Chicago

$550,000

4 Beds ⋅ 2 Baths ⋅ 12667107 MLS ⋅ ACTIVE Status

Rare redevelopment or investment opportunity in the heart of Lakeview. Solid brick 2-flat featuring two 2-bedroom, 1-bath apartments with long-term tenants currently on month-to-month leases. Rents are below market, offering immediate upside potential for investors or future redevelopment. Property is zoned B1-3 and is being offered exclusively as part of a package sale with the adjacent property at 3248 N. Lincoln Ave. Prime location near transportation, shopping, dining, and neighborhood amenities. Excellent opportunity to assemble a larger development site in a highly desirable Lakeview location. Sold as-is. Unfinished basement.

1630 W Melrose Street, Chicago

$650,000

12666947 MLS ⋅ ACTIVE Status

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.

3248 N Lincoln Avenue, 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

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