Sleepy Hollow Homes for Sale

Sleepy Hollow: A Tranquil Retreat in Chicago's Cook County

Nestled in the heart of Cook County, Illinois, Sleepy Hollow is a charming neighborhood that offers a peaceful and serene living experience in the bustling city of Chicago. With its tree-lined streets and well-maintained homes, Sleepy Hollow provides a welcome escape from the fast-paced urban lifestyle.

True to its name, this neighborhood exudes a sense of tranquility that is hard to find in the city. Residents enjoy the quiet ambiance and the close-knit community spirit that Sleepy Hollow offers. The area is known for its beautiful parks and green spaces, making it an ideal choice for nature lovers and those seeking outdoor recreational activities.

For those looking to call Sleepy Hollow home, there is a range of homes for sale to suit different preferences and budgets. From cozy bungalows to spacious family homes, Sleepy Hollow has a variety of options to choose from. The real estate market in this neighborhood is highly sought after, with properties often selling quickly.

Living in Sleepy Hollow means having easy access to all the amenities and conveniences of Chicago. The neighborhood is well-connected to major highways and public transportation, allowing residents to commute to downtown Chicago or other parts of the city with ease.

If you're looking for a peaceful retreat within the vibrant city of Chicago, Sleepy Hollow is the perfect neighborhood for you. With its serene atmosphere, beautiful homes, and convenient location, this hidden gem offers a unique living experience that is hard to find elsewhere.

Newest Sleepy Hollow Homes for Sale

$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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