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3242 N Leavitt Street, Chicago
$1,315,000
5 Beds ⋅ 4 Baths ⋅ 12753253 MLS ⋅ CLOSED 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

3248 N Oakley Avenue, Chicago
$1,300,000
8 Beds ⋅ 3 Baths ⋅ 12737803 MLS ⋅ CLOSED 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

3501 N Damen Avenue, Chicago
$1,350,000
12723814 MLS ⋅ CLOSED 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

1746 W Henderson Street Unit #1, Chicago
$585,000
2 Beds ⋅ 2 Baths ⋅ 12740822 MLS ⋅ CLOSED Status
You won't find a more perfect 2 bed + den condo in arguably the best West Lakeview location! When you walk in, you will immediately notice the newly refinished hardwood floors, fresh paint throughout, and beautifully updated kitchen. The layout won't disappoint either! In addition to your spacious living room, primary suite, and guest bedroom, you will have no trouble working from home in your dedicated office/den, just inside your large private patio. The all-brick building, and well-appointed unit sells themselves, but it gets even better! This very private stretch of Henderson features a one-of-a-kind boulevard with space to walk dogs, play with kids, or have fun with your neighbors. You are also just steps away from some of the best restaurants, shopping, and entertainment that the city has to offer! Come see this home today...it won't last long!

1746 W Henderson Street Unit #1, Chicago

3250 N Damen Avenue Unit #2, Chicago
$575,000
2 Beds ⋅ 2 Baths ⋅ 12710120 MLS ⋅ CLOSED Status
Welcome home to this impeccably maintained and thoughtfully updated 2bed/2bath in the heart of Roscoe Village, where timeless finishes and quality improvements shine throughout. The stunning kitchen has been tastefully refreshed with professionally painted white cabinetry, a designer neutral tile backsplash extending to the ceiling, granite countertops, stainless steel appliances, a breakfast bar, and beautifully refinished hardwood floors, creating a bright and inviting space that's perfect for everyday living and entertaining. The spacious living room is anchored by a cozy fireplace that has been converted to gas for added convenience and ambiance. An Andersen patio door installed in 2023 fills the home with natural light and provides seamless access to the private outdoor deck. Additional recent updates include an LG full-size washer and dryer (2024). Every improvement reflects the seller's pride of ownership, making this home truly move-in ready. The spacious primary suite features a walk-in closet, a private bath with a Jacuzzi tub. Additional highlights include central heat and air, extra storage in the basement, and a spectacular shared rooftop deck with breathtaking skyline views-perfect for entertaining or relaxing with family and friends. Located in the highly sought-after Audubon School District, you'll enjoy easy access to neighborhood parks including Hamlin Park, boutiques, restaurants, coffee shops, fitness centers, grocery stores, the Brown Line, multiple bus routes, and Wrigley Field. Garage parking is included in the price. This exceptional home offers the perfect combination of style, comfort, thoughtful updates, and an unbeatable location. Monthly assessments: $162.00, 2024 Real Estate Taxes: 8,438.10

3250 N Damen Avenue Unit #2, Chicago

1742 W School Street, Chicago
$1,124,375
5 Beds ⋅ 4 Baths ⋅ 12711940 MLS ⋅ CLOSED 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

1908 W Belmont Avenue Unit #3, Chicago
$840,000
3 Beds ⋅ 2 Baths ⋅ 12753609 MLS ⋅ CLOSED Status
Presenting a beautifully appointed three-bedroom, two-bath residence in the heart of Roscoe Village, offering sophisticated interiors, exceptional natural light, and an extraordinary 1,600 square-foot private rooftop retreat. Set within a newer-construction boutique building, this turnkey home includes garage parking, additional storage, and two impressive private outdoor spaces. Designed for both effortless everyday living and entertaining, the expansive open-concept living and dining areas are framed by floor-to-ceiling windows and unobstructed southern exposure. Rich walnut hardwood floors and refined millwork add warmth throughout, while a gas fireplace creates an inviting focal point. The sleek white kitchen is thoughtfully designed with stainless steel appliances, quartz countertops, abundant cabinetry, and an oversized peninsula with generous seating. The serene primary suite easily accommodates a king-size bed and substantial furnishings and features a walk-in closet, cove lighting, and direct access to a private rear deck. The spa-inspired primary bath is finished with a dual vanity, radiant heated floors, an oversized walk-in shower, and separate soaking tub. Two additional generously proportioned bedrooms offer excellent closet space and oversized windows, providing flexibility for family, guests, or a dedicated home office. A new washer and dryer and integrated sound system further enhance the residence. The home's true showpiece is its spectacular 1,600-square-foot private rooftop oasis. This remarkable outdoor space features a custom cedar pergola, fully equipped outdoor kitchen with grill and refrigerator, custom swing, dedicated lounge areas, and fire pit-all set against panoramic views. Designed as an extension of the home, it provides an exceptional setting for intimate evenings, large-scale entertaining, and everything in between. Ideally positioned in one of Chicago's most sought-after neighborhood settings, this exceptional residence places the best of Roscoe Village just outside your door, with acclaimed dining, neighborhood boutiques, nightlife, and convenient public transportation all within easy reach.

1908 W Belmont Avenue Unit #3, Chicago

1955 W Melrose Street Unit #1, Chicago
$725,000
4 Beds ⋅ 3 Baths ⋅ 12743809 MLS ⋅ CLOSED Status ⋅ Roscoe Village BLDG.
Live among the tree-lined streets of Roscoe Village in this rare 4BR/3BA duplex-down made for true Chicago living. At home, hardwood floors run throughout the main level, which brings together an updated kitchen (2023) with quartz countertops and stainless steel appliances, along with a primary suite featuring a walk-in closet and heated en-suite floors. With two spacious living areas, each with its own fireplace, the home offers a comfortable sense of space and flexibility. Step outside to enjoy two private outdoor spaces, including an enclosed front patio and covered rear patio. Perfect for slow mornings, sunny afternoons, or simply unwinding at the end of the day. Recent building improvements include a new roof (2021) and tuckpointing and resealing (2022). Add in the private entrance, dedicated parking, and extra storage to complete the home, with the the charm of Roscoe Village just outside your door.

1955 W Melrose Street Unit #1, Chicago

2224 W Roscoe Street Unit #A, Chicago
$1,200,000
4 Beds ⋅ 5 Baths ⋅ 12743697 MLS ⋅ CLOSED Status ⋅ Roscoe Village BLDG.
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

2307 W Melrose Street Unit #F, Chicago
$920,000
3 Beds ⋅ 3 Baths ⋅ 12723046 MLS ⋅ CLOSED 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. One garage space is included in the price.

2307 W Melrose Street Unit #F, Chicago

2242 W Belmont Avenue Unit #4E, Chicago
$585,000
3 Beds ⋅ 2 Baths ⋅ 12720538 MLS ⋅ CLOSED Status
Come see this elegant & sun-filled home nestled in West Lake View & in the Audubon School District! This well-maintained & updated 3-bedroom, 2-bathroom penthouse condo offers everything discerning homeowners want. The handsome brick facade combined with the impressive interior, beautiful details throughout & open concept floor plan all make this home a must-see! A chef's kitchen with 42"+ cabinets, granite counters, stainless steel appliances & a large island set the tone for this spacious condo. The kitchen, family room & dining area flow seamlessly together & provide a great space for every-day living & entertaining. Natural light comes streaming in from floor-to-ceiling windows. The en-suite, spa-like primary bathroom includes dual vanities, heated flooring, a huge jacuzzi tub & a separate shower stall complete with a steam shower. Both the 2nd & 3rd bedrooms are large enough to fit a king or a queen bed, offer ample closet space & have room for additional furniture. A huge private deck with provides plenty of room for relaxing, entertaining, grilling, etc. Other highlights include hardwood floors throughout, 1 assigned garage parking space w/a 120V EV quick-charger & a bunch of extra storage, a new high-end Bosch dishwasher, a new water tank, newer HVAC & A/C, LG washer/dryer stackable (2021), fresh paint & a wood-burning fireplace. Enjoy abundant free street parking around the building. Convenience abounds in this prime location! It's centrally located & walkable to everything that Roscoe Village & W Lake View have to offer. A 4-minute walk to the Western & Belmont Bus Stop gets you were you need to go & a 9-minute walk to Hamlin Park allows you to enjoy facilities that include a fitness center, 2 gymnasiums, a swimming pool, a kitchen, clubrooms, an assembly hall w/a stage, several baseball fields, a combination football-soccer field, a basketball court, 2 tennis courts, a playground & a fenced-in dog-park. 2018 HVAC & A/C; 2022 H2O; Washer/Dryer from 2021; 2025 Dishwasher; 2004 Frig., Oven & Microwave; Spot tuck-pointing & block sealing in 2025; Roof was re-sealed in 2023

2242 W Belmont Avenue Unit #4E, Chicago

1819 W Cornelia Avenue, Chicago
$825,000
4 Beds ⋅ 2 Baths ⋅ 12720290 MLS ⋅ CLOSED 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

3406 N Bell Avenue Unit #2, Chicago
$267,000
1 Beds ⋅ 1 Baths ⋅ 12742465 MLS ⋅ CLOSED 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

2040 W Belmont Avenue Unit #308, Chicago
$603,000
2 Beds ⋅ 2 Baths ⋅ 12731720 MLS ⋅ CLOSED Status
Roscoe Village luxury living at its finest. This exceptionally bright and airy end-unit residence is tucked into the rear of an intimate boutique elevator building, offering an extra-wide floor plan, beautiful natural light, and peaceful views. Designed for both refined everyday living and effortless entertaining, the spacious open-concept, split-bedroom layout features gorgeous hardwood floors, a handsome gas fireplace, and a private walk-out balcony. The thoughtfully appointed kitchen showcases custom cabinetry, granite countertops, a double pantry, and generous space for a full-size dining table-perfect for hosting family and friends. The expansive primary suite is a true retreat, featuring a beautifully upgraded bath finished in marble with a separate shower and soaking tub. A generously proportioned bedroom and oversized walk-in closet with custom shelving complete this luxurious private haven. Additional highlights include in-unit laundry, abundant storage throughout, and tandem two-car attached, heated garage parking included in the price-a rare and highly desirable amenity in Roscoe Village. Located within the highly sought-after Audubon School boundary and Chicago's top-rated school district, this home places you at the center of everything that makes Roscoe Village so special. Enjoy acclaimed restaurants, neighborhood shops, cafes, and everyday conveniences just blocks away. Fellger Park, the dog park, and Hamlin Park-with its pool, playground, and sports fields-are just steps from your door, while Wrigley Field is approximately a 10-minute stroll away. Downtown Chicago is an easy "L" ride away. Welcome home to Roscoe Village.

2040 W Belmont Avenue Unit #308, Chicago

3414 N Hamilton Avenue, Chicago
$1,753,000
4 Beds ⋅ 5 Baths ⋅ 12694737 MLS ⋅ CLOSED 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

1751 W Roscoe Street Unit #1S, Chicago
$875,000
3 Beds ⋅ 3 Baths ⋅ 12686611 MLS ⋅ CLOSED Status
The gourmet chef's kitchen features custom soft-close cabinetry, quartz countertops, and top-of-the-line Thermador appliances including a 6-burner range, vented hood, beverage fridge, and built-in coffee/cappuccino/espresso machine. The kitchen flows seamlessly into a spacious family room with fireplace and built-in shelving, as well as a dedicated dining area with ample space for hosting family and friends. The main living space opens to a large private deck ideal for grilling and relaxing, along with access to a garage rooftop deck perfect for entertaining. The English lower level has above ground windows, heated floors throughout and includes a luxurious primary suite with a spa-inspired bath featuring rainfall, body spray, and steam shower, double vanity, plus two additional bedrooms. Additional highlights include hardwood floors, recessed lighting, Elan home automation system, premium surround sound with ceiling-mounted speakers, and full-size side-by-side laundry. Complete with one garage parking space, very low HOA fees, and an unbeatable location close to public transportation, restaurants, shopping, and all that Roscoe Village has to offer. Come see this amazing, turn key home today! Showings start June 13 @ 11 am.

1751 W Roscoe Street Unit #1S, Chicago

1815 W School Street, Chicago
$1,650,000
4 Beds ⋅ 4 Baths ⋅ 12687683 MLS ⋅ CLOSED 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

3216 N Ravenswood Avenue Unit #1N, Chicago
$890,000
3 Beds ⋅ 3 Baths ⋅ 12715515 MLS ⋅ CLOSED Status
**HB Offer Deadline 5pm Mon Aug 3** | Picture your Saturdays here. Morning light pours through tall arched windows and across dark hardwood, and the day begins the way the good ones do: coffee at the long quartz peninsula, a fire in the living room hearth, something good on the stove in the elegantly styled kitchen. Under its vaulted arch, the kitchen opens to a dedicated dining area and the living room, inviting company. By noon the carved front door opens to Roscoe Village. It's a short walk to the park, Whole Foods, cafes. And when winter comes, the attached heated garage means no scraping ice off the windshield. Back inside, the home unfolds across two levels: two bedrooms up and one down, a generous recreation room, full laundry, and flexible spaces where a Murphy bed shifts from guest room to office to third bedroom. As the day winds down, you retreat to the primary suite - a tray ceiling, a wall of closets, and a marble bath that earns the word renovated: a soaking tub, a double vanity, a glass steam shower. Just off the bedroom, a private balcony holds the first quiet hour and the last. All of it in an intimate building of just six homes with brick, limestone, and arched windows. Some places you visit. This one you settle into. Step into the chapter you've been waiting to write.

3216 N Ravenswood Avenue Unit #1N, Chicago

2104 W Belmont Avenue Unit #2E, Chicago
$775,000
3 Beds ⋅ 2 Baths ⋅ 12709492 MLS ⋅ CLOSED Status
** Highest & best offers requested by 5pm Monday 7/27, also see broker notes ** Spacious, sun-drenched 3-bedroom, 2-bath condo in a newer elevator building. South-facing with 10-foot ceilings and solid oak floors throughout, the residence opens to a wide front balcony and includes a custom mudroom for organized entry. The highlight is a private rooftop oasis - over 800 sq. ft. designed for entertaining, complete with a newer extended metal & wood pergola that is fully covered, turf garden/play area and a turf "living room." The elegant kitchen features modern white shaker cabinetry, quartz countertops, a large gray island, and Bosch stainless-steel appliances with range hood. Living room, dining area and kitchen flow through to large front, south facing balcony. The generous primary suite offers heated floors, steam shower, and deep custom closets. Smart-home touches include Nest thermostat and LED lighting. Sellers recently painted the entire condo in 2025, new a/c unit in 2024 and newer built wood/metal pergola with electric outlets, built in TV carve-out, and hung lighting fixtures in 2023 on back deck. This boutique, pet-friendly building welcomes visitors in a handsome lobby and includes an extra-deep assigned garage parking space. Ideal for anyone who loves indoor comfort with exceptional outdoor entertaining space. Assessments include elevator maintenance, common area cleaning, garbage and recycling removal. Top ranked Audubon school district. You are steps away from the CTA Brown Line, Mariano's, Hamlin and Fellger parks, and the neighborhood's signature mix of local cafes, restaurants, and laidback taverns.

2104 W Belmont Avenue Unit #2E, Chicago

2254 W Roscoe Street Unit #1, Chicago
$1,390,000
4 Beds ⋅ 4 Baths ⋅ 12707196 MLS ⋅ CLOSED 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

3450 N Claremont Avenue, Chicago
$950,000
5 Beds ⋅ 2 Baths ⋅ 12680410 MLS ⋅ CLOSED 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

1933 W School Street, Chicago
$1,525,000
3 Beds ⋅ 3 Baths ⋅ 12686992 MLS ⋅ CLOSED 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

1740 W Belmont Avenue Unit #1R, Chicago
$650,000
2 Beds ⋅ 2 Baths ⋅ 12680005 MLS ⋅ CLOSED Status
Incredibly cool Lakeview 2-bedroom loft condo, in an intimate elevator building, with 10' ceilings and a massive private deck covering the entire 3-car garage rooftop. This exceptionally open, airy, and quiet, nearly 1,400 sq ft home is wonderfully private, situated one level up & off the main street facing the rear. Featuring classic exposed brick walls & ducts, excellent storage, central HVAC, in-unit laundry, hardwood floors, giant windows, and a cozy wood-burning fireplace. The open kitchen has premium stainless-steel appliances, granite countertops, and a seamless breakfast bar setup perfect for entertaining. Spacious fully enclosed bedrooms, including a large primary suite complete with walk-in closet, an ensuite bathroom with double-sink vanity, separate shower, and a relaxing whirlpool tub. Boutique building amenities include two common rooftop decks with skyline views, an exercise room, a game-room with ping-pong table, and an extra storage closet for each unit. One prime attached garage space is included in the price. Unbeatable location-walk effortlessly to all the shopping, dining, and entertainment in Roscoe Village, Southport Corridor and Lincoln Ave.

1740 W Belmont Avenue Unit #1R, Chicago

1956 W Melrose Street Unit #202, Chicago
$330,000
1 Beds ⋅ 1 Baths ⋅ 12681043 MLS ⋅ CLOSED 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

1841 W Newport Avenue, Chicago
$2,675,000
6 Beds ⋅ 6 Baths ⋅ 12688427 MLS ⋅ CLOSED 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

3438 N Seeley Avenue, Chicago
$985,000
6 Beds ⋅ 3 Baths ⋅ 12663814 MLS ⋅ CLOSED 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

2245 W Melrose Street, Chicago
$1,176,000
7 Beds ⋅ 5 Baths ⋅ 12672659 MLS ⋅ CLOSED 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

2136 W Belmont Avenue Unit #PH, Chicago
$815,000
3 Beds ⋅ 2 Baths ⋅ 12679699 MLS ⋅ CLOSED Status
Experience elevated city living in this stunning 3-bedroom, 2-bath penthouse, located in the highly sought-after Audubon School District and offering approximately 1,830 square feet of beautifully curated interior space in the heart of Roscoe Village. Designed with both style and functionality in mind, this exceptional home features soaring 10.5-foot ceilings, rich hardwood flooring throughout, crown molding, and an airy open-concept layout flooded with natural light thanks to the building's penthouse positioning above neighboring rooftops. The expansive living area centers around a sleek built-in gas fireplace and flows seamlessly into a designer kitchen crafted for entertaining. Highlights include custom white shaker cabinetry, Restoration Hardware lighting and finishes, Calacatta quartz countertops, marble tile backsplash, Kohler undermount sink, oversized 8-foot island, Bosch oven and dishwasher, and a counter-depth Liebherr refrigerator. A balcony directly off the kitchen includes a gas hookup, making outdoor grilling effortless year-round. One of the home's standout features is the incredible private rooftop deck with composite decking, newly added fencing, skyline views, and endless potential for additional build-out. A stylish dry bar at the top landing makes hosting easy, while the added storm door with screen allows for exceptional airflow between indoor and outdoor spaces. The serene primary suite offers a peaceful retreat with a spacious walk-in closet featuring custom shelving and a spa-inspired bath complete with radiant heated floors, dover white shaker custom cabinetry, Calacatta quartz counters, Carrara marble shower surrounds, and Kohler plumbing fixtures. Two generously sized secondary bedrooms both include custom closet systems, including one walk-in closet and another with elegant French-door access. Additional upgrades include extra bathroom cabinetry, attached extra-deep garage parking with storage, and exceptional sunlight throughout every room. Perfectly situated in Roscoe Village, this home places you moments from some of Chicago's most beloved neighborhood destinations. Enjoy easy access to Roscoe Street's boutique shopping, coffee shops, restaurants, and nightlife favorites including Le Sud, Turquoise Cafe, Volo Wine Bar, and The Region. Outdoor lovers will appreciate proximity to Fellger Park, Hamlin Park, and nearby riverwalk paths. Commuting is effortless with close access to the CTA Brown Line at Paulina and Addison, multiple bus routes along Belmont and Damen, and quick connections to the Kennedy Expressway. This penthouse offers the perfect combination of luxury, location, and lifestyle.

2136 W Belmont Avenue Unit #PH, Chicago

2222 W Belmont Avenue Unit #404, Chicago
$778,000
3 Beds ⋅ 2 Baths ⋅ 12685777 MLS ⋅ CLOSED Status
Experience elegant living in this stunning north facing 3 bedroom, 2 bathroom condo in an elevator building located in highly sought after Roscoe Village. This desirable split bedroom floor plan offers both privacy and functionality, featuring custom millwork, crown molding, hardwood floors throughout, and two private outdoor spaces. The spacious open concept living and dining area is filled with natural light from a wall of windows and features a gas fireplace with a soapstone surround, along with direct access to a private balcony. The chef's kitchen is outfitted with top of the line Viking, Sub-Zero, and Bosch appliances, new quartz countertops (2024), a large island, and abundant cabinetry. The expansive primary suite includes dual walk-in closets and a luxurious en suite bathroom complete with double vanities, a walk-in shower, and a whirlpool tub. Two spacious secondary bedrooms offer custom closets and excellent versatility, while the third bedroom is enhanced by thoughtfully designed built-ins and shelving. A full second bathroom with tub/shower combo completes the home. Outdoor living is elevated with a private portion of the rooftop deck featuring new composite decking with views of the city, ideal for relaxing or entertaining. Additional highlights include a dedicated laundry room, heated garage parking, and storage locker included in the price. Perfectly situated near Hamlin Park and the vibrant Roscoe Village corridor, with boutique shopping, acclaimed dining, cafes, neighborhood nightlife, everyday conveniences, public transportation, and located in the sought-after Audubon School district, this home delivers an exceptional blend of luxury and true neighborhood living.

2222 W Belmont Avenue Unit #404, Chicago



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