Quick Waukegan IL MLS Search

Browse All Waukegan IL Between $400K - $500K Properties for Sale

$425,000
4 Beds 3 Baths 12709085 MLS CLOSED Status
Timeless elegance meets everyday comfort in this all-brick Colonial, where historic character and classic craftsmanship shine throughout more than 3,300 square feet of living space. Nestled on a picturesque, tree-lined dead-end street, this one-of-a-kind home offers the perfect blend of charm, space, and location just minutes from downtown Waukegan, the Genesee Theatre, Waukegan Harbor, schools, shopping, and dining. From the moment you step through the arched doorway, you'll be captivated by the home's timeless craftsmanship, showcased by original woodwork, crown molding, and a grand staircase that sets the tone for the home's classic appeal. To one side, the spacious living room features built-in bookshelves and a remarkable fireplace with a sculptural plaster hood and rustic stone surround, creating a stunning architectural centerpiece. On the other, the inviting family room with classic French doors provides the perfect space for both relaxed everyday living and effortless entertaining. The bright white kitchen is designed for gathering, featuring granite countertops, abundant cabinetry, counter seating, and a sunny breakfast nook. The adjacent formal dining room, complete with a charming brick gas fireplace, opens to a relaxing three-season screened porch overlooking the mature, tree-filled backyard is an ideal setting for morning coffee or summer evenings. A full bath and convenient back staircase leading to the second-floor laundry, complete with NEW washer and dryer (2021), add everyday functionality. Upstairs, the spacious primary suite offers two walk-in closets and a private bath with dual vanities and a walk-in shower. Three additional generously sized bedrooms, a full hall bath, and a dedicated desk area perfect for a home office complete the second level. An interior staircase leads to the expansive third-floor attic featuring a cedar closet is ready to be finished into additional living space or used for exceptional storage.The full, unfinished basement includes a recreation area, workshop, abundant storage, and a NEW sump pump with battery backup (2025). A two-car attached garage provides added convenience. Major improvements include a NEW water line from the street to the home (2012) and NEW sewer line from the street to the home (2009), offering peace of mind for years to come. Hardwood floors throughout and underneath carpet. Well maintained and filled with timeless character, this exceptional Colonial is a rare opportunity to own a true piece of Waukegan history.

227 Douglas Avenue, Waukegan

$430,000
4 Beds 2 Baths 12651642 MLS CLOSED Status
Renovated and expanded vintage home on tree-lined Sheridan Road in Waukegan's Near North Historic District. The first floor has been expanded and reconfigured, designed by Diana Melichar Architects of Lake Forest. The renovation included the addition of an airy sunroom at the rear of the house featuring Hardy Board exterior siding, stained cement floor, beamed ceiling, gas fireplace and oversized windows and sliding glass door for maximum views of the expansive back yard ... which leads to the bluff overlooking Lake Michigan in the distance. There is also a walking path behind the garage which leads down the bluff towards the lake. An ideal floor plan on the main level features a separate dining room, spacious kitchen and living room, updated powder room, office area, and the sunroom. The remodeled kitchen is filled with natural sunlight through an oversized window, high end appliances, hardwood flooring, ample counter space and storage with built-in pantry in the cabinetry. Windows throughout have been replaced with high quality Marvin windows, stained and etched glass accents in the living room and dining room; glass blocks added in the basement to bring in daylight. A new solid wood front door opens to large foyer with brilliant crystal chandeliers and dramatic wooden staircase. Central A/C; tankless water heater; furnace replaced 2023. This elegant home features high ceilings throughout the first floor, the creation of a first floor laundry room, original hardwood floors refinished on first level, updated bathrooms and scenic views from north and east side of home. There is a seamless blend of Craftsman oak millwork with 19th Century millwork with bullseye casings. The expansive grounds are beautifully landscaped front, sides and rear. The 2-car garage features a unique bonus room with fireplace. There is ample room for parking several cars in long driveway and apron turnaround. The outdoor patio off the sunroom addition provides opportunity for serenity, privacy and recreation in the deep back yard with mature trees.

1021 N Sheridan Road, Waukegan

$440,000
4 Beds 3 Baths 12620863 MLS CLOSED Status
Nestled on a quiet cul-de-sac and set on a beautifully mature .35-acre homesite, this distinctive cedar tri-level with an 18X50 sub-basement offers a rare blend of 4 levels of living space. With 4 bedrooms, 3 full bathrooms, a 2-car garage, and an extended driveway that accommodates up to 6 additional vehicles, this home combines thoughtful functionality with a standout presence. Surrounded by mature trees, abundant natural light, and a layout designed to adapt to your lifestyle, you'll immediately feel the balance of comfort, space, and privacy that makes this home truly special. Step inside and experience a multi-level lifestyle designed for both connection and comfort. Vaulted ceilings elevate the main living spaces, while the open sightlines between three levels create a seamless flow and an airy, expansive feel. Sunlight pours in from an abundance of windows positioned across all levels, filling the home with warmth and energy throughout the day. The updated kitchen is both stylish and functional, featuring custom cabinetry, stainless steel appliances, and a dedicated eating area with direct access to an outdoor deck-perfect for morning coffee or casual dining. Just beyond, the formal dining room sets the stage for intimate dinners or lively gatherings with friends and family. A private living room, tucked behind elegant French doors, offers a quiet retreat-ideal for reading, relaxing, or simply unwinding. The lower-level serves as the heart of the home, featuring an impressive 24x34 walk-out family room anchored by a floor-to-ceiling brick fireplace that creates a striking focal point. This level also offers a versatile fourth bedroom, an ideal in-law arrangement, a home office, or a creative space, along with a full bathroom and convenient access to the laundry. From the family room, step out to the extended brick paver patio, where a private alcove setting invites peaceful evenings overlooking the expansive backyard and the quiet surroundings. Upstairs, the primary suite is a true retreat, featuring vaulted ceilings, a generous 5x11 walk-in closet, and its own private 5x13 deck-an ideal setting to end the day under the stars. Two additional spacious bedrooms and a full bathroom complete the upper level. An additional sub-basement expands the possibilities even further, offering an expansive 18x50 unfinished space-perfect for storage, a workshop, or future build-out to suit your needs. Great dining in closing proximity and Warren Schools! No HOA!

4759 Crest Court, Waukegan

$395,000
5 Beds 4 Baths 12513496 MLS CLOSED Status
CHERISHED BRICK RANCH IN DOUGLAS NURSERY- This newly updated 5 bedroom, 3.1 Bath home is truly one of a kind. It is trimmed with thoughtful little details everywhere you turn. Solid wood finishes with built-in cabinetry and generous closet space throughout. Desirable layout, gorgeous four-season room. HUGE fully, fenced-in back yard. Concrete outdoor patio. 2 fireplaces. Full wet-bar in Basement. 2-car attached garage with epoxied floor and brand-new service doors. Brand-new, separate oversized 24x24 back garage off alley was a passionately built addition in 2013 from the hefty concrete foundation up. It has a gated entrance and long, spacious driveway for your RV, work trailer, guest parking, etc. The living design offers so many options. Bring your business, growing family, make multi-generational living possible, etc. MOST RECENT IMPROVEMENTS: JULY-OCT 2025 Complete professional landscaping including re-routing of ground drainage. // All gutters cleaned out and properly routed. // Home completely & freshly painted from head to toe with high-quality Sherwin Williams paint. // New High-End Sinks and Faucets in both Powder Room & Kitchen. // Newly sanded, painted and updated kitchen cabinets finished with quality brass hardware. // Brand New, High-Quality, Chair-Height Toilet, Vanity, Sink Base and light fixture in powder room. // All hardwood floors fully sanded down, refinished and freshly stained. // Brand New carpet and light fixture in 4-Season Room as well as Fully and beautifully Recarpeted Basement Floors. // Back Asphalt Driveway Freshly Sealcoated. // New window in basement. // New Fire safe Doors in Attached Garage. // NEW IN 2023-2024: 35-year shingle roof. // NEW from Abt Appliances: Washer & Dryer, Dishwasher and Refrigerator // 2022: AC/Furnace, Sump Pump, Hydro-Jetted Sewer Line. 2018: Added Egress in Basement and Bathroom. ** Listing agent is related to the seller.

615 Tiffany Drive, Waukegan

$397,500
4 Beds 2 Baths 12465125 MLS CLOSED Status
Live on tree-lined Sheridan Road in Waukegan's Near North Historic District in a fantastic classic American Foursquare home! 4 bedrooms, 1.1 bathrooms. Enter through the gracious window-lined vestibule ( 9'2" x 8'3" ) lit by a beautiful chandelier through a glass-paned door to the spacious Living Room with a gas fireplace. Double French glass-paned doors open into the coffered-ceiling Dining Room with its dazzling original chandelier surrounded by a ceiling medallion, paneled walls with vintage plate rails and original wall sconces. The Living Room has yet another glass-paned door that leads to the tranquil cozy Den with a wood-burning fireplace, the Powder Room and the central staircase. The swinging door from the Dining Room leads to the updated all SS kitchen and special Breakfast Room surrounded with three walls of windows overlooking the patio and mature trees in the backyard. Natural light from the large window on the staircase landing floods the staircase to the 2nd floor: four bedrooms, each with its own walk-in closet, and the recently refreshed bathroom. The huge Primary Bedroom faces East and South with a large walk-in closet sporting its own window. Second bedroom / sitting room has original casement windows on three sides. The Third and Fourth bedrooms have windows on two sides. Attic is reached by an interior staircase. Create your own get-away in the basement: Knotty Pine panels line the Family Room which has a gas fireplace, built-in book shelves and windows. A large Recreation Room to design to your own desires with windows. Large bright Laundry Room and a flexible Bonus Room located near plumbing. There is one set of built-in cabinets and drawers on the main level and another set on the 2nd floor. Historical Features: Original doors, four interior doors with glass panes, Oak hardwood floors through 99 per cent of the above ground home, original millwork throughout, glass door knobs, 12" sculptured baseboards, coffered ceiling in Dining Room and original light fixture and wall sconces, many windows with original leaded glass, three fireplaces ( 1 wood-burning and 2 gas ), casement windows, historic Purington Paver patio and bluestone pathway leads to the fenced-in backyard with mature trees. Space Pac was installed before 2007 and has not been operational since 2013. Detached brick 2 car garage. City of Waukegan Inspection is completed. Home to be sold "AS IS".

1028 N Sheridan Road, Waukegan

$388,000
3 Beds 3 Baths 12446859 MLS CLOSED Status
Welcome to Your Backyard Paradise in Woodland School District Tucked in a quiet corner of the desirable Woodland School District, this 3 bed, 2.1 bath home isn't just move-in ready-it's move-in and start-living ready. Step inside to find gleaming hardwood floors, soaring ceilings, and an abundance of natural light pouring through oversized windows. The family room flows seamlessly into the island kitchen, where 42" cabinets, granite counters, and stainless steel appliances make both weekday dinners and weekend entertaining a joy. The wall of windows frames postcard-worthy views of the pond and woodlands, leading you out to a spacious patio-perfect for morning coffee, evening cocktails, and everything in between. Upstairs, the primary suite feels like a private retreat, complete with an updated bath (yes, it has heated floors!). Two additional bedrooms and another updated bath mean there's space for everyone. The partially finished lower level features a built-in electric fireplace, a whimsical kids' firehouse play area, and two massive storage rooms you'll be grateful for. The backyard is a showstopper-fully fenced, with blackberry and raspberry bushes ready for summer snacking. The pond is stocked with bass (bring your fishing pole!) and even allows paddle boating. HVAC is just one year old, so the big-ticket items are already taken care of. Roof is 10 Years Old. Bonus things the sellers love: Paddle boating on the pond at sunset Grabbing fresh berries right from the backyard Watching the seasons change over the water and woodlands That basement storage-truly a game-changer If you've been looking for a home that blends comfort, charm, and a touch of adventure, you've found it.

1039 S Pleasant Hill Gate, Waukegan

Start Your Search



The data relating to real estate for sale on this website comes in part from the Broker Reciprocity program of Midwest Real Estate Data LLC. Real Estate listings held by brokerage firms other than our company are marked with the MRED Broker Reciprocity logo or the Broker Reciprocity thumbnail logo (the MRED logo) and detailed information about them includes the names of the listing brokers. Some properties which appear for sale on this website may subsequently have sold and may no longer be available. The accuracy of all information, regardless of source, including but not limited to square footages and lot sizes, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Copyright 2026 MRED LLC. All rights reserved.

Based on information submitted to the MLS Grid as of . All data is obtained from various sources and has not been, and will not be, verified by broker or MLS Grid. MRED supplied Open House information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the DMCA) provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to DMCAnotice@theMLSGRID.com.

The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner’s behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.

Some listings have been excluded from this website.

Between $400K - $500K Waukegan Real Estate

Our website features the best real estate search for between $400k - $500k properties available in Waukegan and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire. 

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood! 

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Contact us today to find out how we can be of assistance to you!