
4444 N Winchester Ave, Chicago, IL 60640
What This House Offers
Move right into the spectacular extra-wide single family home on an oversized lot in an ideal Ravenswood location. Built in 2000, this all-brick home offers a... terrific layout, generous room sizes, and rare space both inside and out. The main level features a large newer kitchen that opens to the family room and deck overlooking the deep backyard. The kitchen offers custom cabinetry, Viking and Bosch appliances, a deep sink, excellent storage, and a long breakfast bar perfect for everyday living and entertaining. The spacious family room includes room for casual living and dining, plus a nearby small office area that can be closed off or used for additional pantry or coat storage. The front living and dining room offers a fireplace, tray ceilings, and space for a large dining setup or grand piano. A center staircase, crown molding, hardwood floors, and powder room complete the main floor. Upstairs, the oversized primary suite features a tray ceiling, two walk-in closets, and a beautifully redone bath with floating vanity, walk-in shower, Victoria & Albert soaking tub, stone finishes, and skylight. Two additional bedrooms share a newer hall bath, including a large front bedroom with vaulted ceiling and plantation shutters. The second-floor laundry room includes a utility sink and newer front-loading washer and dryer. The lower level offers a huge recreation room with fireplace, plus two additional bedrooms and a full bath, ideal for guests, nanny, office, workout space, or extended living. Extra-deep lot with large backyard, sport court, two-car garage with great storage, and two separate furnace and air conditioning systems. Walk to the Brown Line, Metra, restaurants, shops, Lycee Francais, Welles Park, Lincoln Square, and more. Select furniture pieces may remain for added convenience, including the baby grand piano in the living room, a beautiful addition even if you do not play. This is a rare opportunity to rent a spacious, move-in ready single-family home in a prime Ravenswood location, don't miss it!
Unit
- $8,500
Total Monthly Price - 5 Beds
- 4 Baths
- 3900 sq. ft.
- Available Now
Home Features
- Air Conditioning
- Basement
- Deck
- Dining Room
- Dishwasher
- Disposal
- Family Room
- Fireplace
- Furnished
- Hardwood Floors
- Heating
- Kitchen
- Microwave
- Range
- Recreation Room
- Refrigerator
- Stainless Steel Appliances
- Walk-In Closets
- Washer/Dryer
- Washer/Dryer Hookup
Community Features
- Garages
4444 N Winchester Ave is a single-family home for rent in Chicago, IL
Fees and Policies
The fees below are based on community-supplied data and may exclude additional fees and utilities.
- Garage
Property Fee Disclaimer Based on community-supplied data and independent market research. Subject to change without notice. May exclude fees for mandatory or optional services and usage-based utilities.
Explore Commute Options
- Drive Time--
- Walk Time--
- Bike Ride Time--
- Public Transit--
About the Listing Agent

Greg Desmond is a seasoned real estate broker and perennial Top Producer in the Chicago Association of Realtors. But what more makes him stand out from the crowd is the attentive service he provides. Since 2006, Greg’s service was rated perfect by his clients each year through independently conducted surveys as part of his Quality Service Certified (QSC) membership. In 2007, and again in 2010, he was named a member of QSC’s Hall of Fame as one of the “Best in the Business”, one of only 250 agents among the over 50,000QSC agents eligible nationwide. This award recognizes not only volume, but more importantly independently rated customer satisfaction. “Providing the utmost in service” is more than a tagline with Greg, it is a way of doing business every day. Greg launched his real estate career in 1999. He knew that providing personalized & attentive service makes a client's life easier and more productive, thus winning their continued loyalty. His dedication and high degree of client service led to a fast start in real estate. Since the beginning, he has created a very loyal client base though aggressive and creative marketing and a personalized, hands-on approach to getting the job done. A native of Detroit, Greg has resided on Chicago's north side for over twenty years. Greg has a business degree in marketing from the University of Notre Dame, and enjoys water skiing, pottery, and Chicago's diverse cultural scene, and supports many charitable endeavors. He prides himself on getting the best results for every client while making the transaction a personable and enjoyable experience. Experienced in sales of properties ranging from the South Loop to Edgewater, his business concentrates in Lakeview, Lincoln Park, Andersonville, Bucktown, Gold Coast and surrounding areas. Regardless of which neighborhood you prefer, you will be glad to have him with you every step of the way, providing sound counsel well beyond a successful closing.
Area Scores
Walkability
Exceptionally walkable100 / 100
Transit
Strong public transit80 / 100
Driveability
Fairly drivable40 / 100
Bikeability
Very bikeable80 / 100
Travel and Transit








Local Education
Colleges and Universities
School
Commute Time (Distance)
Truman College
Drive: 3 min (1.3 mi)
DeVry University-Illinois
Drive: 5 min (2.4 mi)
North Park University
Drive: 5 min (2.5 mi)
Northeastern Ill. Univ.
Drive: 8 min (3.6 mi)
Discover Ravenswood, Chicago, IL
Shopping Centers
Shoppers will appreciate 4444 N Winchester Ave proximity to Ravenswood Plaza and The Square. Ravenswood Plaza is 0.3 miles away, and The Square is within a 17 minute walk.
Commuting
With a TransitScore of 80, 4444 N Winchester Ave has strong public transit, including 10 transit stops within 4.2 miles. Transit options include Montrose Station (Brown Line) and Damen Station (Brown Line).
Parks and Recreation
Recreational activities near 4444 N Winchester Ave are plentiful. Discover 5 parks within 3.8 miles, including Chase Park, Winnemac Park, and Wrightwood Park.
Airports
Living in Ravenswood provides easy access to Chicago O'Hare International, located just 22 minutes from 4444 N Winchester Ave. Another nearby airport is Chicago Midway International, located 16.6 miles away.
Nearby Properties You Might Like
Within 50 Miles of 4444 N Winchester Ave
Find More Rentals in Chicago
- Houses with Pets Allowed in Chicago
- Affordable Houses for Rent in Chicago
- Fully Furnished Homes for Rent in Chicago
- Modern Homes for Rent in Chicago
- Houses for Rent with a Yard in Chicago
- Homes for Rent with a Garage in Chicago
- Houses for Rent with Fireplace in Chicago
- Houses for Rent with a Patio in Chicago
- Houses for Rent with Washer and Dryer in Chicago
- Houses for Rent with Utilities Paid in Chicago










