$1,699,900

beds

baths

half bath

4,200

square ft

1442 W Cuyler Avenue

Chicago, Illinois 60613

Closed / MLS #12357514 / Single Family / Lakeview

Listing information updated 7/13/2025 at 6:03am

Welcome to this beautifully maintained and timeless Graceland West Greystone. This single-family home is perfectly situated on a picturesque, tree-lined street within the highly sought-after Blaine School district. With five spacious bedrooms and four and a half bathrooms, 1442 W Cuyler masterfully blends classic architectural charm with sophisticated modern updates-creating a warm, elegant, and functional space ideal for both everyday living and entertaining. Step inside to soaring ceilings and meticulously preserved original millwork. The sun-drenched formal living and dining rooms offer a welcoming atmosphere for gatherings of all sizes, while the heart of the home-an updated chef's kitchen-boasts custom cabinetry, premium appliances, and an oversized island perfect for casual meals or culinary masterpieces. The thoughtfully designed layout continues into a generous family room that opens to a large back deck and leads to a brick two-car garage. Tucked above the garage is an urban rooftop retreat like no other-complete with a pergola, lounging space, and even a slide, adding a touch of joy. Upstairs, the expansive primary suite is a true sanctuary, featuring a walk-in closet and a spa-caliber bath with a soaking tub, dual vanities, and a glass-enclosed shower. Two spacious bedrooms, each with en suite baths, complete the second level. The fully finished lower level offers exceptional versatility with a spacious rec room, an additional bedroom, a full bath, a dedicated office, and a beautifully designed wine room-perfect for storing your favorite vintages at the ideal temperature. Conveniently located just steps from the Southport Corridor's charming boutiques, top-rated restaurants, parks, and Brown Line, this home offers the perfect balance of luxury, location, and urban lifestyle. Don't miss this rare opportunity to own a truly special home in one of Chicago's premiere neighborhoods.

Full Features

Architecture Style:

Greystone

Exterior Type:

Brick

Basement:

Finished,Full,Daylight

Beds Above Grade:

Cooling System:

Central Air

Heating System:

Natural Gas, Forced Air

Appliances:

Microwave, Dishwasher, Refrigerator, High End Refrigerator, Freezer, Washer, Dryer, Stainless Steel Appliance(s), Wine Refrigerator

Main Level Primary Bedroom:

Fireplace:

Yes

Pool:

Age:

100+ Years

Parking Type:

Garage - Garage Door Opener,On Site,Garage Owned,Detached,Garage

Parking Spaces:

Garage:

Detached

Room Count:

Water Front:

Square Feet:

4,200

Lot Size:

Standard Chicago Lot

Acreage:

0.0717

Internal Features:

Wet Bar

External Features:

Outdoor Grill, Patio/Porch

Room Information

Living Room:

17x15 - Main

Dining Room:

15x13 - Main

Kitchen:

16x14 - Main

Family Room:

29x19 - Lower

Primary Bedroom:

17x15 - Second Level

2nd Bedroom:

15x13 - Second

3rd Bedroom:

13x11 - Second

4th Bedroom:

12x10 - Lower

Great Room:

19x16 - Main Level

Bedroom 5:

10x9 - Lower Level

Deck:

21x19 - Second Level

Laundry:

11x6 - Lower Level

Taxes & Assessments

Tax Amount:

$19,367

Tax Year:

2023

Location

Zip Code:

60613

City:

Chicago

County:

Cook

Schools

School District(s):

299

Elementary School:

Blaine Elementary School

Middle School:

Blaine Elementary School

High School:

Lake View High School

Architecture Style:

Greystone

Exterior Type:

Brick

Basement:

Finished,Full,Daylight

Beds Above Grade:

Cooling System:

Central Air

Heating System:

Natural Gas, Forced Air

Appliances:

Microwave, Dishwasher, Refrigerator, High End Refrigerator, Freezer, Washer, Dryer, Stainless Steel Appliance(s), Wine Refrigerator

Main Level Primary Bedroom:

Fireplace:

Yes

Pool:

Age:

100+ Years

Parking Type:

Garage - Garage Door Opener,On Site,Garage Owned,Detached,Garage

Parking Spaces:

Garage:

Detached

Room Count:

Water Front:

Square Feet:

4,200

Lot Size:

Standard Chicago Lot

Acreage:

0.0717

Internal Features:

Wet Bar

External Features:

Outdoor Grill, Patio/Porch

Living Room:

17x15 - Main

Dining Room:

15x13 - Main

Kitchen:

16x14 - Main

Family Room:

29x19 - Lower

Primary Bedroom:

17x15 - Second Level

2nd Bedroom:

15x13 - Second

3rd Bedroom:

13x11 - Second

4th Bedroom:

12x10 - Lower

Great Room:

19x16 - Main Level

Bedroom 5:

10x9 - Lower Level

Deck:

21x19 - Second Level

Laundry:

11x6 - Lower Level

Tax Amount:

$19,367

Tax Year:

2023

Zip Code:

60613

City:

Chicago

County:

Cook

School District(s):

299

Elementary School:

Blaine Elementary School

Middle School:

Blaine Elementary School

High School:

Lake View High School

Listing Office: Eras Brokerage and Realty LLC

Listing Office Phone: 847.323.2372

Disclaimer: The data relating to real estate for sale on this website comes courtesy of Midwest Real Estate Data, LLC as distributed by MLS GRID. Real estate listings held by brokerage firms other than @properties are marked with the Broker Reciprocity thumbnail logo and detailed information about them includes the name of the listing brokers. Properties displayed may be listed or sold by various participants in the MLS. Based on information submitted to the MLS GRID as of 7/13/2025 at 6:03am. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Some listings have been excluded from this website.