Sleepy Hollow Real Estate

Located in the heart of Chicago, Sleepy Hollow is a charming neighborhood in Cook County, Illinois. Known for its peaceful atmosphere and close-knit community, Sleepy Hollow offers a suburban feel while still being just a short distance from the bustling city center.

One of the standout features of Sleepy Hollow is its beautiful green spaces and parks. Residents can enjoy leisurely strolls or picnics in the neighborhood's well-maintained parks, providing a serene escape from the urban hustle and bustle. The abundance of trees and greenery adds to the overall tranquility of the area, making it an ideal place for families and nature enthusiasts alike.

In terms of housing, Sleepy Hollow boasts an array of architectural styles, ranging from cozy bungalows to modern townhouses. The real estate market in this neighborhood offers a variety of options to suit different preferences and budgets. Whether you are looking for a spacious family home or a cozy apartment, Sleepy Hollow has something to offer for everyone.

As for amenities, residents of Sleepy Hollow have easy access to a range of shopping centers, restaurants, and entertainment options. The neighborhood is also conveniently located near major transportation routes, making it easy to commute to other parts of Chicago or explore the surrounding areas.

Overall, Sleepy Hollow is a hidden gem within the vibrant city of Chicago. With its peaceful ambiance, green spaces, and convenient location, it is no wonder that this neighborhood is highly sought after by those looking for a tranquil yet accessible place to call home.

Newest Listings in Sleepy Hollow

$399,900

3 Beds ⋅ 2 Baths ⋅ 12714788 MLS ⋅ NEW Status

Welcome to this beautifully renovated 5-bedroom, 2-bathroom brick home offering about 2,000 square feet of finished living space! Every detail has been thoughtfully updated, creating a move-in-ready home that blends modern style with functional living. The bright, open interior features refinished hardwood floors, fresh paint, updated lighting, and a stunning remodeled kitchen complete with white shaker cabinetry, quartz countertops, a designer tile backsplash, stainless steel appliances, and abundant cabinet space. Both full bathrooms have been tastefully renovated with contemporary finishes and custom tile work. The fully finished basement significantly expands the living space and offers incredible flexibility with additional bedrooms, a large recreation area, and plenty of storage. Step outside to enjoy the rear deck overlooking the fenced backyard, along with a detached 2-car garage and additional parking. Major updates throughout provide peace of mind while allowing the next owner to simply move in and enjoy. Conveniently located near shopping, dining, parks, schools, public transportation, and major expressways, this beautifully remodeled home is ready for its next chapter!

4324 S Keating Avenue, Chicago

$398,000

3 Beds ⋅ 2 Baths ⋅ 12706777 MLS ⋅ PRICE CHANGE Status

This beautiful 5-bedroom raised ranch in the LeClaire Courts neighborhood offers modern style and a practical layout. The open-concept main floor features a bright living space and a spacious kitchen with stainless steel appliances, quartz countertops, and a large pantry. Refinished hardwood flooring throughout the living room and the bedrooms. Waterproof luxury vinyl plank flooring adds both style and durability to the kitchen.The finished basement provides extra living space with a large family room, two additional bedrooms, a full bathroom, and a laundry area-ideal for guests, extended family, or a home office. The backyard is perfect for relaxing, entertaining, or summer cookouts. Recent updates include electrical, plumbing(2026), a new sump pump(2026),Furnace(2025) AC(2025), Front Fence and railing (2026,)Garage roof and gutter 2026, giving added peace of mind. Conveniently located near major highways and Midway Airport, this home combines comfort, style, and an excellent location. Schedule your private showing today!

4508 S Keating Avenue, Chicago

$129,900

2 Beds ⋅ 1 Baths ⋅ 12702103 MLS ⋅ ACTIVE Status

UNIQUE OPPORTUNITY FOR INVESTOR TO TAKE THIS WELL LOCATED PROPERTY AND CONVERT IT INTO BEAUTIFUL BRAND NEW HOME. THIS HOME IS COMPLETELY GUTTED TO THE STUDS. COME IN WITH YOUR FLOOR PLANS AND TURN YOUR INVESTMENT INTO A MONEY MAKER. PROPERTY IS LISTED SIGHT UNSEEN (LSU) NO SHOWINGS ALLOWED & NO INTERIOR ACCESS.

4637 S Kilpatrick Avenue, Chicago

$259,000

4 Beds ⋅ 2 Baths ⋅ 12682357 MLS ⋅ ACTIVE Status

Prime Location. This spacious two-story single-family home offers convenience, comfort, and ample parking in the highly sought-after Archer Heights neighborhood. The home features a bright living room, dining room, and two bathrooms. Enjoy outdoor living with a front yard, rear patio, and fenced yard with iron gates for added privacy and security. Parking is a standout feature, with a 2-car garage, side drive accommodating up to 6 additional vehicles, and plenty of street parking available for guests. Conveniently located near I-55, this property provides easy access to shopping, restaurants, schools, parks, and much more. A great opportunity to own a home in a well-established and desirable neighborhood! Schedule your private showing today!

4323 S Keating Avenue, Chicago

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