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Uptown Real Estate

Uptown has a glamorous past as the stomping grounds of Charlie Chaplin, Gloria Swanson and Al Capone. Today it shines as a place to call home for Chicagoans seeking incredible access to the lakefront, public transportation and a vibrant entertainment scene.
Uptown’s early glamour is still reflected in its historic buildings. The neighborhood’s commercial and cultural center is Broadway, with historic Uptown Square at its center.
The area experienced a housing construction boom following the World’s Columbian Exposition. Several of the neighborhood’s luxurious entertainment venues were built in the 1920s reflecting the ornate artistry of the Exposition pavilions.
Uptown continues to be one of the city’s most popular destinations for music lovers, with rock concerts at Aragon Ballroom and Riviera Theatre and jazz at the legendary Green Mill. The jazz venue was a favorite of notorious gangster Capone, who used its underground tunnels to bootleg whiskey and make a hasty retreat from police.
In addition to entertainment, the neighborhood has a number of independent bookstores, art galleries, cafes, and restaurants. The community works to balance new development with a commitment to preserve its past.
Homebuyers have their choice of many housing styles, from lakefront high-rises and vintage walk-ups to new-construction condos and townhomes. A number of beautiful old mansions also line several streets just west of Margate Park.

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Browse All Uptown IL Properties for Sale

$574,900
3 Beds 2 Baths MRD11745274 MLS CONTINGENT Status
30% sold! Latest rendition of today's modern by Vari Architects. 4900 N Kenmore is a NEW CONSTRUCTION building in the emerging East Andersonville environs, only 1 block to the El station and just blocks to the lakefront. This is a high second floor unit: three bedroom & two bathroom plus rooftop den with front 17'x7' terrace plus additional garage top deck. The building has a total of seven units positioned on a 50'x150' corner lot allowing for wide and long unit footprints. Several floorplans including: Two-3bed/2bath units on middle floor, each with front balcony and garage deck, two-3bed/2bath units on top floor with front balcony, rooftop den, and private rooftop terraces, three-3bed/2 1/2 bath duplex units with balcony and garage deck, one floorplan with fourth bedroom/den/office. This is a full-masonry building with significant window openings, an all brick exterior, modern design, and fine attention to every detail. Oversized European multi-position windows allow for maximum light and air from all exposures. Superior European-inspired finishes throughout. Details include wide 5" plank engineered hardwood floors, recessed LED lighting, 7' solid-core doors, and 9'+ ceiling height. Custom European-style flat panel cabinetry, oversized island, quartz countertops, Bosch appliance package, under-cabinet lighting, and a dry beverage bar are just a few of the luxury finishes in the kitchen. Bathrooms have quartz countertops, porcelain tile, and polished chrome fixtures. The master bath also has a NuHeat heated floor system with a programmable thermostat. Private decks have composite decking, lighting, power, and gas connections. The property is entirely fenced and has concrete sidewalks and rear driveway. Garage parking is included with every unit. A one year builder warranty included. List of recently completed projects by architect/builder Vari Architects is available. Interior photos are from the very similar recently completed 4937 N Winthrop. There is a limited window of opportunity to be able to select some interior finishes in order to personalize your new home. Delivery May, 2023.

4900 N Kenmore Avenue Unit #2S, Chicago

$699,900
3 Beds 3 Baths MRD11745271 MLS CONTINGENT Status
30% sold! Latest rendition of today's modern by Vari Architects. 4900 N Kenmore is a NEW CONSTRUCTION building in the emerging East Andersonville environs, only 1 block to the El station and just blocks to the lakefront. This is a duplex unit: three bedrooms & two and a half bathrooms, living/dining, separate family room, with two 15'x6' terraces plus private 144sqft garage deck. The building has a total of seven units positioned on a 50'x150' corner lot allowing for wide and long unit footprints. Several floorplans including: Two-3bed/2bath units on middle floor, each with front balcony and garage deck, two-3bed/2bath units on top floor with front balcony, rooftop den, and 500sqft private rooftop terraces, three-3bed/2 1/2 bath duplex units with balcony and garage deck, one floorplan with fourth bedroom/den/office. This is a full-masonry building with significant window openings, an all brick exterior, modern design, and fine attention to every detail. Oversized European multi-position windows allow for maximum light and air from all exposures. Superior European-inspired finishes throughout. Details include wide 5" plank engineered hardwood floors, recessed LED lighting, 7' solid-core doors, and 9'+ ceiling height. Custom European-style flat panel cabinetry, oversized island, quartz countertops, Bosch appliance package, under-cabinet lighting, and a dry beverage bar are just a few of the luxury finishes in the kitchen. Bathrooms have quartz countertops, porcelain tile, and polished chrome fixtures. The master bath also has a NuHeat heated floor system with a programmable thermostat. Private decks have composite decking, lighting, power, and gas connections. The property is entirely fenced and has concrete sidewalks and rear driveway. Garage parking is included with every unit. A one year builder warranty included. List of recently completed projects by architect/builder Vari Architects is available. Interior photos are from the very similar recently completed 4937 N Winthrop. There is a limited window of opportunity to be able to select some interior finishes in order to personalize your new home. Delivery expected May, 2023.

4900 N Kenmore Avenue Unit #1W, Chicago

$674,900
3 Beds 2 Baths MRD11743289 MLS ACTIVE Status
30% sold! Latest rendition of today's modern by Vari Architects. 4900 N Kenmore is a NEW CONSTRUCTION building in the emerging East Andersonville environs, only 1 block to the El station and just blocks to the lakefront. This is a TOP FLOOR unit: three bedroom & two bathroom plus rooftop den with front 17'x7' terrace plus private 500sqft rooftop deck with skyline views. The building has a total of seven units positioned on a 50'x150' corner lot allowing for wide and long unit footprints. Several floorplans including: Two-3bed/2bath units on middle floor, each with front balcony and garage deck, two-3bed/2bath units on top floor with front balcony, rooftop den, and private rooftop terraces, three-3bed/2 1/2 bath duplex units with balcony and garage deck, one floorplan with fourth bedroom/den/office. This is a full-masonry building with significant window openings, an all brick exterior, modern design, and fine attention to every detail. Oversized European multi-position windows allow for maximum light and air from all exposures. Superior European-inspired finishes throughout. Details include wide 5" plank engineered hardwood floors, recessed LED lighting, 7' solid-core doors, and 9'+ ceiling height. Custom European-style flat panel cabinetry, oversized island, quartz countertops, Bosch appliance package, under-cabinet lighting, and a dry beverage bar are just a few of the luxury finishes in the kitchen. Bathrooms have quartz countertops, porcelain tile, and polished chrome fixtures. The master bath also has a NuHeat heated floor system with a programmable thermostat. Private decks have composite decking, lighting, power, and gas connections. The property is entirely fenced and has concrete sidewalks and rear driveway. Garage parking is included with every unit. A one year builder warranty included. List of recently completed projects by architect/builder Vari Architects is available. Interior photos are from the very similar recently completed 4937 N Winthrop. There is a limited window of opportunity to be able to select some interior finishes in order to personalize your new home. Delivery expected May, 2023.

4900 N Kenmore Avenue Unit #3N, Chicago

$419,900
3 Beds 3 Baths MRD11730923 MLS ACTIVE Status
Amazing location with 2 parking spots! Tri-level townhome with 3 bedrooms/2.5 bathrooms that lives like a single-family home in an 8-unit building. Wonderful location in Uptown on a beautiful, one-way residential street. Private entrance leads to entryway that opens up to the first level with living room, dining area, powder room, deck with Pella sliding door and kitchen with granite countertops, stainless steel appliances (new LG gas stove, dishwasher and microwave), pantry with custom storage and eat-in area. Upstairs second level has 2 bedrooms and 2 full bathrooms; primary bedroom an en suite with walk-in closet. Lower level has family room with wood-burning fireplace and 3rd bedroom with another large closet. Price includes TWO PARKING SPACES; one garage space has dedicated EV charger hookup wired to the home's electric meter and one tandem exterior driveway space. In-unit LG laundry, lots of storage and Nest thermostat/CO detectors throughout. Central lakefront location, close to all that Uptown has to offer, plus a short distance to Lakeview, Andersonville, Lincoln Square and easy Lake Shore Drive access to downtown. Short walk to the red-line CTA and buses. Strong reserves, current HOA budget, roof recently inspected/maintained, pet-friendly building in a well maintained, all owner-occupied building. This home has longtime, lucrative experience renting a bedroom for extra income!

860 W Lakeside Place Unit #C, Chicago

$399,000
3 Beds 2 Baths MRD11737697 MLS CONTINGENT Status
Experience vintage elegance in this lakefront residence, this amazing condo exudes timeless charm. The intricate greystone facade is thoughtfully set back from the street, creating a serene and tranquil living experience within this home. South exposure, second floor, is bright, spacious, and fully renovated, meticulously designed with no detail overlooked. This highly sought-after six-room layout boasts soaring ceilings, oversized windows, and distinct living and dining areas with flexible interchangeable spaces. Two generously sized bedrooms and a versatile den/third bedroom, or office space. Flexible living and dining room that seamlessly flows into an entertainer's dream kitchen. This culinary space features abundant cabinetry, ample preparation surfaces, and a delightful eat-in island, all in the warm southern exposure. The modern kitchen extends to a spacious private deck, perfect for alfresco dining and outdoor living. The residence's standout features include fully refinished wood work in the rich hardwood floors, deep coffered moldings, an elegant centerpiece fireplace, picture rail moldings, a vintage clawfoot tub, and intricate plaster detailing. In-unit laundry adds the modern convenience. The solid association is all owner-occupants. The impeccably maintained common areas offer additional spaces for relaxation and entertainment. With heat included in assessments, new boiler, ample storage, and a dedicated parking space included in the price. Located just steps from the park, lake, bike and running paths, and Montrose Beach, this charming home is perfectly positioned in the heart of East Uptown. Enjoy proximity to an array of restaurants, pubs, the iconic Green Mill, shops, and grocery stores, while benefiting from easy access to the Red Line, public transportation, and Lake Shore Drive. Minutes to Andersonville, Lakeview and Ravenswood. A truly exceptional offering that will captivate discerning buyers seeking the perfect fusion of historic allure and modern refinement.

823 W Lakeside Place Unit #2W, Chicago

$475,000
3 Beds 2 Baths MRD11732904 MLS CONTINGENT Status
This stunning Uptown penthouse is the perfect combination of convenience and luxury. Upon entering you'll be greeted by a bright and spacious living/dining room that boasts soaring vaulted ceilings, a cozy gas fireplace with a granite surround, and warm sunny skylights. Throughout the home are elegant dark stained hardwood flooring, crown molding, and solid core doors. The fixtures and finishes are well crafted with impeccable detail. The kitchen is a chef's paradise, featuring stainless steel appliances that are only two years old, stunning granite countertops, 42" cherry cabinets, under cabinet lighting, and a gorgeous stone backsplash. You'll love waking up to the master suite's spacious walk-in closet, marble master bath with dual vanities, luxurious steam/rain shower, and relaxing Jacuzzi tub. The additional bedrooms are equally impressive, with French doors and wainscotting that add an extra touch of charm and character. Step outside onto the large deck and take in the breathtaking views of the city skyline and the neighborhood. This unit also comes with all the amenities you need, including a washer and dryer in like-new condition, secured garage parking, sizable private storage in the basement, and brand new HVAC and water heater. And the location can't be beat - only two blocks away from the LakeFront, Montrose Beach, Dog Beach, and multiple parks. You'll be just a short 10-minute walk away from Target, Marianos, Aldi, and some of the best nightlife in the city at The Riviera, Aragon Ballroom, and The Green Mill. And with easy access to the Argyle Red Line station and the soon-to-be-finished Lawrence Red Line station, you'll have no trouble getting around. This unit is a commuter's dream and perfect for families looking to make the most of everything the city has to offer.

4857 N Winthrop Avenue Unit #3N, Chicago

$664,900
3 Beds 3 Baths MRD11719888 MLS ACTIVE Status
30% sold! Latest rendition of today's modern by Vari Architects. 4900 N Kenmore is a NEW CONSTRUCTION building in the emerging East Andersonville environs, only 1 block to the El station and just blocks to the lakefront. This is a duplex unit: three bedrooms & two and a half bathrooms with front 17'x7' terrace plus private 144sqft garage deck. The building has a total of seven units positioned on a 50'x150' corner lot allowing for wide and long unit footprints. Several floorplans including: Two-3bed/2bath units on middle floor, each with front balcony and garage deck, two-3bed/2bath units on top floor with front balcony, rooftop den, and 500sqft private rooftop terraces, three-3bed/2 1/2 bath duplex units with balcony and garage deck, one floorplan with fourth bedroom/den/office. This is a full-masonry building with significant window openings, an all brick exterior, modern design, and fine attention to every detail. Oversized European multi-position windows allow for maximum light and air from all exposures. Superior European-inspired finishes throughout. Details include wide 5" plank engineered hardwood floors, recessed LED lighting, 7' solid-core doors, and 9'+ ceiling height. Custom European-style flat panel cabinetry, oversized island, quartz countertops, Bosch appliance package, under-cabinet lighting, and a dry beverage bar are just a few of the luxury finishes in the kitchen. Bathrooms have quartz countertops, porcelain tile, and polished chrome fixtures. The master bath also has a NuHeat heated floor system with a programmable thermostat. Private decks have composite decking, lighting, power, and gas connections. The property is entirely fenced and has concrete sidewalks and rear driveway. Garage parking is included with every unit. A one year builder warranty included. List of recently completed projects by architect/builder Vari Architects is available. Interior photos are from the very similar recently completed 4937 N Winthrop. There is a limited window of opportunity to be able to select some interior finishes in order to personalize your new home. Delivery expected May, 2023.

4900 N Kenmore Avenue Unit #1N, Chicago

$699,900
4 Beds 3 Baths MRD11719879 MLS ACTIVE Status
30% sold! Latest rendition of today's modern by Vari Architects. 4900 N Kenmore is a NEW CONSTRUCTION building in the emerging East Andersonville environs, only 1 block to the El station and just blocks to the lakefront. This is a duplex unit: four bedrooms & two and a half bathrooms with front 17'x7' terrace plus private 144sqft garage deck. The building has a total of seven units positioned on a 50'x150' corner lot allowing for wide and long unit footprints. Several floorplans including: Two-3bed/2bath units on middle floor, each with front balcony and garage deck, two-3bed/2bath units on top floor with front balcony, rooftop den, and 500sqft private rooftop terraces, three-3bed/2 1/2 bath duplex units with balcony and garage deck, one floorplan with fourth bedroom/den/office. This is a full-masonry building with significant window openings, an all brick exterior, modern design, and fine attention to every detail. Oversized European multi-position windows allow for maximum light and air from all exposures. Superior European-inspired finishes throughout. Details include wide 5" plank engineered hardwood floors, recessed LED lighting, 7' solid-core doors, and 9'+ ceiling height. Custom European-style flat panel cabinetry, oversized island, quartz countertops, Bosch appliance package, under-cabinet lighting, and a dry beverage bar are just a few of the luxury finishes in the kitchen. Bathrooms have quartz countertops, porcelain tile, and polished chrome fixtures. The master bath also has a NuHeat heated floor system with a programmable thermostat. Private decks have composite decking, lighting, power, and gas connections. The property is entirely fenced and has concrete sidewalks and rear driveway. Garage parking is included with every unit. A one year builder warranty included. List of recently completed projects by architect/builder Vari Architects is available. Interior photos are from the very similar recently completed 4937 N Winthrop. There is a limited window of opportunity to be able to select some interior finishes in order to personalize your new home. Delivery expected May, 2023.

4900 N Kenmore Avenue Unit #1S, Chicago

$564,900
3 Beds 2 Baths MRD11719877 MLS ACTIVE Status
30% sold! Latest rendition of today's modern by Vari Architects. 4900 N Kenmore is a NEW CONSTRUCTION building in the emerging East Andersonville environs, only 1 block to the El station and just blocks to the lakefront. This is a high second floor unit: three bedroom & two bathroom plus rooftop den with front 17'x7' terrace plus additional garage top deck. The building has a total of seven units positioned on a 50'x150' corner lot allowing for wide and long unit footprints. Several floorplans including: Two-3bed/2bath units on middle floor, each with front balcony and garage deck, two-3bed/2bath units on top floor with front balcony, rooftop den, and private rooftop terraces, three-3bed/2 1/2 bath duplex units with balcony and garage deck, one floorplan with fourth bedroom/den/office. This is a full-masonry building with significant window openings, an all brick exterior, modern design, and fine attention to every detail. Oversized European multi-position windows allow for maximum light and air from all exposures. Superior European-inspired finishes throughout. Details include wide 5" plank engineered hardwood floors, recessed LED lighting, 7' solid-core doors, and 9'+ ceiling height. Custom European-style flat panel cabinetry, oversized island, quartz countertops, Bosch appliance package, under-cabinet lighting, and a dry beverage bar are just a few of the luxury finishes in the kitchen. Bathrooms have quartz countertops, porcelain tile, and polished chrome fixtures. The master bath also has a NuHeat heated floor system with a programmable thermostat. Private decks have composite decking, lighting, power, and gas connections. The property is entirely fenced and has concrete sidewalks and rear driveway. Garage parking is included with every unit. A one year builder warranty included. List of recently completed projects by architect/builder Vari Architects is available. Interior photos are from the very similar recently completed 4937 N Winthrop. There is a limited window of opportunity to be able to select some interior finishes in order to personalize your new home. Delivery May, 2023.

4900 N Kenmore Avenue Unit #2N, Chicago



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