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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.
| DAYS ON MARKET | 5 | LAST UPDATED | 5/6/2025 |
|---|---|---|---|
| YEAR BUILT | 1896 | COMMUNITY | CHI - Lake View |
| GARAGE SPACES | 2.0 | COUNTY | Cook |
| STATUS | Active | PROPERTY TYPE(S) | Single Family |
| School District | Lake View High School |
|---|---|
| Elementary School | Blaine Elementary School |
| Jr. High School | Blaine Elementary School |
| High School | Lake View High School |
| ADDITIONAL DETAILS | |
| AIR | Central Air |
|---|---|
| AIR CONDITIONING | Yes |
| APPLIANCES | Dishwasher, Dryer, Freezer, Microwave, Range, Refrigerator, Stainless Steel Appliance(s), Washer, Wine Refrigerator |
| AREA | CHI - Lake View |
| BASEMENT | Daylight, Finished, Full, Yes |
| CONSTRUCTION | Brick |
| EXTERIOR | Barbecue, Outdoor Grill |
| FIREPLACE | Yes |
| GARAGE | Yes |
| HEAT | Forced Air, Natural Gas |
| INTERIOR | Wet Bar |
| LOT | 3123 sq ft |
| LOT DIMENSIONS | 25X125 |
| PARKING | Garage Door Opener, On Site, Detached, Garage |
| SEWER | Public Sewer |
| STYLE | Greystone |
| TAXES | 19367 |
| WATER | Public |
MORTGAGE CALCULATOR
TOTAL MONTHLY PAYMENT
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Listed with Eras Brokerage and Realty LLC
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Copyright 2025 MRED. All rights reserved.
The broker providing these data believes them to be correct, but advises interested parties to confirm them before relying on them in a purchase decision.
Copyright 2025 MRED. All rights reserved.
This IDX solution is (c) Diverse Solutions 2025.
