Browse All Roscoe Village IL Historical 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

$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

$289,000

1 Beds ⋅ 1 Baths ⋅ 12681043 MLS ⋅ CONTINGENT Status

A true jewel box, this charming 1926 condo is perfectly situated in the heart of Roscoe Village. Beautifully updated while preserving its vintage character, this special home offers timeless style, abundant natural light, and an exceptional floor plan designed for comfortable everyday living. From the moment you step through the front door, you'll be impressed by its impeccable condition and thoughtful updates. The sun-drenched living room, highlighted by a graceful coved ceiling, is framed by two walls of windows with custom window treatments, filling the space with natural light and creating a warm, inviting atmosphere. The separate dining room, featuring attractive tile flooring, is enhanced by gorgeous built-ins and French doors that add both architectural charm and functionality-perfect for intimate dinners or entertaining friends. The updated kitchen is beautifully appointed with newer appliances, 42-inch white cabinetry, granite countertops, tile flooring, and excellent storage. The beautifully renovated bathroom showcases an attractive vanity, designer lighting, stylish tilework, and an elegant tub/shower combination. The spacious bedroom offers generous closet space and serves as a peaceful retreat at the end of the day. Additional improvements include updated lighting with dimmer switches throughout, fresh paint, gleaming hardwood floors, and newer mechanicals, including the furnace, central air conditioning, and water heater. Convenient rear stairs lead to the basement, which provides free laundry and additional storage, in-unit laundry is permitted to be installed. Just moments from the Brown Line, neighborhood boutiques, restaurants, coffee shops, and all the charm that makes Roscoe Village one of Chicago's most beloved neighborhoods, this sweet and sophisticated condo is the perfect place to call home.

1956 W Melrose Street Unit #202, 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

$849,900

5 Beds ⋅ 2 Baths ⋅ 12680410 MLS ⋅ PENDING Status

Rare opportunity to own a 2-flat in the heart of Roscoe Village. The property presents an excellent opportunity for conversion to a single-family home, redevelopment, or continued use as a multi-unit property, all in a highly desirable location. The first floor features a 2 bed/1 bath unit, while the second floor offers a 2 bed/1 bath unit plus an additional finished bedroom in the partially finished walk-up attic. The attic features 7-foot ceilings with ample unfinished storage space and potential for a future duplex-up expansion. New roof in 2021. A 25 x125 Lot, a spacious yard, with an oversized 20' x 21' two-car garage. Above the garage is a matching 20' x 21' loft area with 7-foot ceilings, offering abundant storage or the perfect work space. Audubon Elementary and Lake View High School. You'll be in the sought-after Roscoe Village, just steps away from charming boutiques, coffee shops, restaurants, and neighborhood gathering spots. Experience the area's unique "small-town feel in the city" and all the conveniences of this vibrant North Side neighborhood.

3450 N Claremont 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

$840,000

4 Beds ⋅ 2 Baths ⋅ 12656155 MLS ⋅ ACTIVE Status

Beautifully updated 4 bed, 2 bath single-family home in Roscoe Village on an oversized 32.5 foot lot, just steps away from the magnet Hamilton Elementary School. Step into a welcoming separated living room and formal dining room that overlooks expansive green space. The oversized main-floor primary suite, added to the rear of the original frame home, features a wood-burning fireplace, a Juliet balcony, and two (2) large walk-in closets. It sits adjacent to an updated main-floor bathroom boasting a Jacuzzi tub and a separate tiled walk-in shower with new shower glass. Upstairs you'll benefit from three (3) bedrooms with a full claw-foot tub bathroom. The partially finished basement offers a spacious recreation room with a fireplace, a dedicated laundry and mechanical room, a workshop area, and an elevated crawl space perfect for extra storage. Off of the rear porch on the main floor is a finished foyer that welcomes you inside your home, while the rare, oversized detached three-car garage provides exceptional off-street parking. Priced to sell, come see this charming, move-in-ready home ready for your final touches!

1819 W Cornelia 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

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