Sleepy Hollow Real Estate

Welcome to Sleepy Hollow, a serene gem nestled within the vibrant tapestry of Chicago, Illinois. This charming neighborhood in Cook County is the perfect blend of suburban tranquility and urban convenience, making it an ideal place to call home.

Sleepy Hollow is characterized by its tree-lined streets, spacious yards, and a strong sense of community. Residents enjoy a peaceful atmosphere that feels worlds away from the hustle and bustle of city life, yet all the amenities of downtown Chicago are just a short drive away. This neighborhood is perfect for families, young professionals, and retirees alike, offering a diverse mix of residents who cherish the friendly, welcoming vibe.

Nature lovers will appreciate the nearby parks and recreational spaces, ideal for leisurely strolls, picnics, or weekend sports. The local schools are highly regarded, providing quality education and fostering a close-knit community spirit. With various local shops and dining options, residents can indulge in delightful culinary experiences without venturing far from home.

Sleepy Hollow is also well-connected to public transportation, making commuting to downtown Chicago a breeze. Whether you’re looking to explore the city’s rich cultural offerings or prefer the tranquility of suburban living, Sleepy Hollow strikes the perfect balance.

In essence, Sleepy Hollow is more than just a neighborhood; it’s a lifestyle choice. With its idyllic setting, strong community ties, and convenient access to the best of Chicago, it beckons those looking for a place to thrive. Discover your dream home in Sleepy Hollow today, and experience the charm of this delightful neighborhood!

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 ⋅ ACTIVE 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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