View All Lincoln Square Chicago IL Homes with Rooftop Deck Listings

$1,241,000
6 Beds 3 Baths 12686346 MLS CLOSED Status
Exceptional opportunity to own one of Lincoln Square's most charming and architecturally significant greystones on one of the neighborhood's most picturesque, tree lined blocks. Beautifully maintained and thoughtfully updated over the years, this timeless two flat with an additional garden apartment showcases true pride of ownership while offering remarkable flexibility for investors, owner occupants, or those seeking the perfect house hacking opportunity in one of Chicago's most coveted neighborhoods. The first floor residence offers two spacious bedrooms and a beautifully renovated bathroom, complemented by an expansive floor plan featuring a gracious living room, sun filled den, formal dining room, and an updated eat in kitchen. Rich original oak hardwood floors, intricate millwork, and a stunning built in hutch have been meticulously preserved, highlighting the home's historic character. The renovated kitchen opens to a private rear porch, an ideal setting for morning coffee, al fresco dining, or entertaining guests. Generous storage can be found throughout the home. The second floor residence features three bedrooms, one updated bathroom, and a dedicated office just off the kitchen, perfect for today's work from home lifestyle. The spacious living room is flooded with beautiful southern sunlight, while the oversized formal dining room provides an inviting space for family gatherings and entertaining. The bright and welcoming garden apartment offers a well designed one bedroom, one bathroom layout with abundant natural light, creating an attractive option for additional rental income, extended family, or guest accommodations. The building has been exceptionally cared for, reflecting decades of thoughtful stewardship and meticulous maintenance. Additional storage and a shared laundry area are conveniently located in the basement. Outside, the professionally designed Zen inspired rear garden creates a peaceful urban retreat. The full masonry three car garage is crowned by an impressive finished rooftop deck, an extraordinary outdoor living space rarely found in the city. The location is simply unmatched. Just one block from the vibrant heart of Lincoln Square, you'll enjoy effortless access to beloved neighborhood restaurants, cozy cafes, boutique shopping, neighborhood taverns, parks, the CTA Brown Line, the Lincoln Square Farmers Market, the Chicago Riverwalk trail system and the year round concerts, festivals, and community events that make this one of Chicago's most treasured neighborhoods. Whether you're looking for a trophy investment, a multi generational home, or an owner occupied property with substantial income potential, this exceptional greystone offers timeless architecture, impeccable condition, enduring value, and outstanding future upside in one of Chicago's strongest and most sought after residential markets.

2230 W Leland Avenue, Chicago

$1,050,000
12675568 MLS CONTINGENT Status
*** Multiple Offers Received - Best and Finals Due Monday at 12pm *** Exceptional mixed-use 4 unit investment opportunity in the heart of Lincoln Square! Situated on one of Chicago's most desirable commercial corridors, this fully occupied corner property features two oversized 3-bedroom apartments and two highly visible retail storefronts, creating a rare blend of stable income, future upside, and prime location. The retail component includes a prominent Lincoln Avenue storefront with a full basement and a long-term lease of $2550 escalating each year by $50 extending through 2028, along with a Western Avenue storefront occupied by a long-term tenant who is prepared to execute a new three-year lease. Above the retail spaces are two spacious residential units: a 3-bedroom, 1.5-bath apartment on the second floor renting for $2600 with a lease through 06/2027 and a 3-bedroom, 1-bath apartment on the third floor renting for $2400 with a lease until 07/2026. Both apartments feature central air conditioning, in-unit laundry, hardwood floors, and beautiful original woodwork that reflects the character and charm Lincoln Square is known for. The property also offers the potential to create a rooftop deck above the Western Avenue retail space. Currently zoned B3-3, the property's lot and exceptional location may present future redevelopment potential, including a larger mixed-use or transit-oriented development (buyer to verify). The building is well-maintained, fully occupied, and generates immediate income, while the upcoming vacancy of the third-floor apartment in July 2026 provides a unique opportunity for an owner-occupant, value-add investor, or buyer looking to renovate and bring rents closer to market levels. Located within the highly sought-after Waters Elementary School attendance boundary, this property offers an added layer of appeal for future owner-occupants and tenants alike. Residents and tenants enjoy immediate access to some of Chicago's most beloved restaurants, cafes, shops, and neighborhood destinations. Gene's Sausage Shop & Delicatessen, Garcia's, Barba Yianni, Willow Cafe, Potbelly, Lincoln Square Athletic Club, and OrangeTheory are all just steps away. Commuters will appreciate easy access to the Western Brown Line station, multiple CTA bus routes, and the convenience of living in one of Chicago's most walkable and sought-after neighborhoods. Whether you're seeking a strong long-term investment, an owner-occupied opportunity, or a strategic redevelopment play, 4754 N. Lincoln Avenue offers an outstanding combination of location, income, future potential, and an unbeatable Lincoln Square location. Listing agent is related to the owner and has financial interest in the property.

4754 N Lincoln Avenue, Chicago

$415,000
2 Beds 2 Baths 12366943 MLS CLOSED Status
You'll love the natural light and expansive feel of this top-floor, corner 2-bedroom, 2-bath condo in a boutique elevator building in the heart of Lincoln Square! With 11' ceilings, refinished hardwood floors throughout, and a split-bedroom layout, this home offers the perfect balance of style, space, and functionality. The open-concept living and dining area flows seamlessly into a modern kitchen with 42" cabinets, granite countertops, and stainless steel appliances-ideal for entertaining or everyday living. The spacious primary suite includes a large en suite bath and ample space for a sitting area or home office. The second bedroom is generously sized with great closet space and easy access to the second full bath. A private laundry/storage room with side-by-side washer and dryer is located just across the hall from the unit. Enjoy warm-weather days on the common rooftop deck with stunning skyline views, or relax in the shared courtyard with a grill area. Garage parking is included in the price. Recent building updates include a new roof installed in 2023 and masonry work completed on the north and west-facing exterior in 2024, with roof maintenance also performed in fall 2024-offering peace of mind for years to come. Live just steps from all the best of Lincoln Square-shops, restaurants, bars, parks, and public transportation are right outside your door. Move right in and enjoy vibrant city living with every convenience!

4751 N Artesian Avenue Unit #401, Chicago

$850,000
3 Beds 2 Baths 12374068 MLS CLOSED Status
Welcome to Lincoln Square and this lovely boutique condo building! Step off the elevator to the foyer of the penthouse and enter the spacious, airy home you've been looking for. The open concept living area is anchored by a fireplace and flanked by custom built-ins. There is plenty of space for gatherings and a true dining area, with ample space for a large table. Sliding glass doors lead seamlessly to a terrace with tree top views, and plenty of room for grilling or relaxing in the sunshine. The kitchen is perfect for any serious cook or host, with plenty of cabinet and counter space, quartz countertops and premium appliances: Fisher Paykel and Bosch. The primary suite is spacious and features two walk-in closets plus a dedicated closet for linens. The classicly designed marble primary bath has a double vanity and a steam shower. Two more graciously sized guest bedrooms and a full bath complete the interior living space. Take the elevator or the stairs to the massive rooftop deck where you can have a drink at the bar and enjoy the sunset views to the west or City views to the south. This outdoor space is truly exceptional and has it all: a gas fireplace, bar with beverage fridge, storage and seating, retractable awnings, built in storage and an irrigation system. This home is a must see and exudes quality, from the crown molding and hardwood floors throughout to the custom build out of every closet. A space in the attached, heated garage is included. All of this in desirable Lincoln Square, a short walk to the Brown line, Giddings Plaza and Lincoln Avenue's shopping, dining and entertainment options. This one is not to be missed.

4912 N Lincoln Avenue Unit #501, Chicago

$2,300,000
4 Beds 5 Baths 12121047 MLS CLOSED Status
Welcome to this elegantly stunning, new construction, developer's home, featuring over 5,000 square feet of living space in the heart of Lincoln Square, where no detail was spared! This oversized lot translates into an intelligently designed floor plan. Step inside an inviting foyer with large-format marble floors and a wall-to-wall guest closet. Marvel at the 10-foot coffered ceilings, 8-foot solid wood doors, white oak hardwood floors and large Marvin windows, welcoming that natural, crisp sunlight into your home. French doors open to the Juliet balcony off the spacious living room with a marble, wood-burning fireplace. It seamlessly flows into a formal dining room that can easily seat ten, for those fun, all-night-long, dinner parties! Proceed into the kitchen and family room and be amazed by the sheer size of this very open space. The kitchen boasts 48" custom cabinetry, chased with undermount lighting, a 48" Sub-Zero refrigerator, a Dacor Pro-Grade oven, tiled with a marble and glass mosaic backsplash, Calacatta quartz c-tops and a 10-foot island dressed with quartzite iceberg c-tops. The island comfortably seats four and there is more available seating at the formal breakfast area that towers with its high vaulted ceilings and bay windows. Enjoy your loved ones in the adjoining family room with a marble, wood-burning fireplace and large wet bar with a wine cooler to enjoy your favorite spirits! Then, be impressed with an unparalleled powder room, beautified with custom marbled floors, a Habersham Provence vanity topped with an iceberg quartzite c-top, a timeless Kallista commode and stunning THG Paris Swarovski fixtures; this space is ultimately adorned with a transformative Schonbek light fixture. Head upstairs to the second floor, where there are four bedrooms, three baths and a laundry closet all on one level. Be amazed by the huge primary suite with double walk-in closets, sitting area with bay windows and vaulted ceilings, a marvelous spa-like bath with oversized marble shower, heated marble floors, elegant floor-to-ceiling custom wall tiles set against a Kohler soaking tub, Furniture Guild vanities adorned with crystal handled fixtures and finished with marble c-tops. Three additional generous-sized bedrooms, one en-suite with walk-in closet, bathroom accessorized with Porcelanosa vanity and expertly curated tiles, Kohler fixtures and plumbing console. Two additional bedrooms have ample closet spaces and share a bathroom with elevated design that features Porcelanosa wall and floor tiles, including a gold-designed tiled runway, double vanity with quartzite c-tops, lavish Dornbracht fixtures, as well as a Kohler plumbing console. Continue to the lower level where there is a large, enclosed mudroom with custom cabinetry and additional closet and storage spaces. Enter the huge rec room with a wet bar, electric fireplace with Porcelanosa airslate natural stone and a wonderful office space. The lower level also features a secondary kitchen with custom cabinetry, quartz c-tops and a stainless steel Kitchen Aid appliance package. Also included is a full bath featuring a designer-tiled shower, Madeli vanity with quartz c-top and Grohe fixtures. Additionally, the large, main laundry room includes a stainless steel sink, LG washer and dryer with an additional "small-load" pedestal washer below. This lower level is complete with a substantial, finished multi-purpose storage room. Additional features include a: 3-car, detached garage with rooftop deck, outdoor stone wood-burning fireplace, in/outdoor sound system, Hunter Douglas window treatments, ProCom Security System, heated floors throughout, with ice-melt outdoor pathways! Short distance to Lycee French School, Old Town School of Folk Music, train station, many parks, shops and restaurants that define Lincoln Square. This home is a true gem. A 10!

2236 W Ainslie Avenue, Chicago

$1,830,000
4 Beds 5 Baths 12014782 MLS CLOSED Status
Nestled on a 30-foot lot, this stunning residence offers a total of 6 bedrooms, with 4 upstairs and 2 downstairs, providing ample space for living and entertaining. Completed in 2020, this newer construction home has been meticulously crafted with custom details and high-end upgrades throughout. The main level impresses with 10-foot ceilings and a thoughtful layout that seamlessly integrates two fireplaces for entertainment-one in the front half and another in the rear, creating a warm and inviting atmosphere. The rear fireplace extends into the family room, effortlessly connecting indoor and outdoor living spaces, where a stone patio awaits, offering a serene and private retreat. A charming rooftop deck sits atop the garage, offering a picturesque setting for hosting gatherings or enjoying peaceful moments. The gourmet kitchen is a chef's dream, equipped with top-of-the-line Gaggenau appliances, luxurious quartzite countertops, a spacious breakfast area, and a convenient butler's pantry. The primary bedroom exudes comfort and sophistication, flooded with natural light and featuring a lavish primary bath with heated floors, a double vanity, a separate water closet, and a rejuvenating steam shower. Downstairs, the finished lower level boasts radiant heated floors, a spacious family room with a wet bar, a guest bedroom, and a well-appointed home gym, providing ample space for relaxation and recreation.Experience the epitome of luxury living in this meticulously designed home, where every detail has been carefully curated to offer the utmost in comfort and style.

4834 N Leavitt Street, Chicago

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Lincoln Square, Chicago IL · Curated MLS Search

Homes with Rooftop Deck in Lincoln Square, Chicago IL

An editorially curated view of every active homes with rooftop deck listing in Lincoln Square, Chicago IL. Updated in real time from the local MLS, presented without the noise.

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