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$899,000 Contingent

  • For Sale
  • Contingent
  • Single Family
  • 4 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 2,404 Sq. Ft.
  • 2 Car Garage
  • Updated 3 days ago
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**MULTIPLE OFFERS HAVE BEEN RECEIVED.** Best and Final Due Sunday 7/5/26 via Email by 5pm. No Escalation Clauses.*** Welcome to this meticulously maintained 4-bedroom, 2.5-bath all-brick ranch nestled in the highly sought-after The Willows neighborhood of Glenview. Offering the convenience of one-level living with a beautifully finished lower level, this exceptional home combines timeless charm with thoughtful modern updates. From the moment you arrive, you'll appreciate the outstanding curb appeal, professionally landscaped grounds, and inviting private courtyard entrance. Inside, an open and light-filled floor plan showcases gleaming floors, oversized windows, and spacious living and dining areas designed for both everyday living and effortless entertaining. The updated kitchen features white and blue cabinetry, Thermidor Professional series appliances, generous counter space, and a bright eating area that flows seamlessly into the cozy living room with a fireplace. Sliding glass doors lead to a large patio overlooking the fully fenced backyard-perfect for outdoor gatherings and relaxing evenings. The bedroom wing includes four generously sized bedrooms with organized closets. The luxurious primary suite offers a custom walk-in closet and a beautifully renovated en-suite bath complete with radiant heated floors, a glass-enclosed shower, and designer finishes. An updated hall bath also features radiant heated flooring and soak in tub. The finished lower level expands the home's living space with a large recreation room, abundant storage, and flexible space ideal for a home office, gym, or guest accommodations. Recent improvements provide true peace of mind, including newer flooring, updated electrical, Marvin windows and siding door, newer Armstrong HVAC, copper plumbing, newer roof, lighting, fresh paint, a security fence, and professional landscaping. Ideally located near parks, schools, golf courses, shopping, dining, and transportation, this move-in-ready home offers the perfect blend of comfort, style, and convenience in one of Glenview's most desirable neighborhoods. Welcome home to The Willows-where quality, location, and exceptional living come together.

Full Property Details for 4044 Chester Dr

General

  • Price: $899,000
  • Taxes: $10,987 (2024)
  • Status: Contingent
  • Type: Single Family
  • Source: MRED
  • MLS ID: 12692911
  • Updated: 7/8/2026
  • Added to Site: 12 day(s) ago

Rental Information

  • Complex Features: Park, Pool, Tennis Court(s), Curbs, Sidewalks, Street Lights, Street Paved

Interior

  • Basement: Finished, P
  • Interior Features: Wet Bar, 1st-Floor Bedroom, 1st-Floor Bath, Built-in Features, Walk-In Closet(s), Open Floorplan, Granite Counters, Separate Dining Room
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Fireplace(s): Living Room, Wood-Burning, Gas Starter
  • Appliances: Double Oven, Dishwasher, High-End Refrigerator, Disposal, Wine Refrigerator, Cooktop, Range Hood, Humidifier

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1
  • Bathroom Features: Double Sink, Soaking Tub

Bedrooms

  • Total Bedrooms: 4

Additional Information

  • Equipment: Cable TV, Carbon Monoxide Detectors, Sump Pump, Lawn Sprinkler, Backup Sump Pump, Internet-Fiber
  • Other Features: School Bus Service, Commuter Bus, Commuter Train, Interstate Access

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 2
  • Parking Features: Concrete, Garage Door Opener, Yes, Garage Owned, Attached, Garage

Location

  • Area: Glenview / Golf
  • County: Cook
  • Township: Northfield
  • Subdivision: The Willows
  • Driving Directions: WILLOW TO LANDWEHR SOUTH TO CHESTER EAST TO HOME

School Information

  • School District: 31
  • Elem School District: 31
  • Midd School District: 31
  • High School District: 225
  • Elementary School: Henry Winkelman Elementary Schoo
  • Middle School: Field School
  • High School: Glenbrook South High School
  • Private School: Glenbrook South High School

Community

  • Assoc. Fees Include: None

Heating & Cooling

  • Cooling Type: Central Air Conditioning
  • Heating Type: Natural Gas, Forced Air

Utilities

  • Sewer: Public Sewer
  • Water: Lake Michigan

Structural Information

  • Architectural Info: Ranch
  • Architectural Style: Ranch
  • Construction: Brick
  • Exterior Const.: Brick
  • Basement: Yes
  • Basement Desc.: Finished, Partial
  • Foundation: Concrete Perimeter
  • Roof: Asphalt
  • Windows: Screens, Blinds
  • Doors: ENERGY STAR Qualified Doors, Sliding Glass Door(s)
  • Square Feet: 2,404
  • Sq. Ft. Source: Assessor
  • Year Built: 1973
  • Built Before 1978: Yes
  • Remodeled/Updated: 2017

Lot Features

  • Lot Size (Acres): 0.2333
  • Lot Size Range: Less than .25 Acre
  • Lot Dimensions: 132 x 77

Financial Considerations

  • Parking Included: Yes
  • Assessment Year: 1973
  • Tax Amount: $10,987.21
  • Tax Year: 2024
  • Pays Sewer: Public Sewer

Disclosures and Reports

  • Ownership: Fee Simple
  • Property ID: 4202030050000

Listed by Compass

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Listing agents

— 4044 Chester Dr —

  • Compass

  • Compass

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Save up to an additional 20% by bundling your home and auto together!

Schools serving 4044 Chester Dr

School Districts:West Northfield School District 31, Northfield Township High School District 225
NameGradesDistance
Henry Winkelman Elementary School
1919 Landwehr Road, Glenview, IL 60026
PK-50.6 mi
Field School
2055 Landwehr Road, Northbrook, IL 60062
6-80.9 mi
Glenbrook South High School
4000 West Lake Avenue, Glenview, IL 60026
9-121 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 4044 Chester Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
7/01/2026
Listed
$899,000
93.33%
MLS
2/22/2017
Sold
$465,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 4044 Chester Dr

Year
Property Taxes
Change
Tax Assessment
Change
2023
$10,229
—
$69,000
35%
2023
$10,229
1%
$51,058
—
2022
$10,141
5%
$51,058
21%
2021
$9,633
4%
$42,315
—
2020
$9,236
-11%
$42,315
-7%
2018
$10,408
16%
$45,637
-2%
2019
$8,964
-5%
$46,500
2%
2017
$9,392
3%
$45,637
—
2016
$9,089
-3%
$45,637
6%
2015
$9,371
3%
$42,858
—
2014
$9,119
2%
$42,858
—
2013
$8,914
—
$42,858
-8%
2012
$8,921
—
$46,519
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Listed by Anne DuBray

4044 Chester Drive, Glenview, IL 60026 (MLS# 12692911) is a Single Family property with 4 bedrooms, 2 full bathrooms and 1 partial bathroom. 4044 Chester Drive is currently listed for $899,000 and was received on July 01, 2026. Want to learn more about 4044 Chester Drive? Do you have questions about finding other Single Family real estate for sale in Glenview? You can browse all Glenview real estate or contact a Coldwell Banker agent to request more information.

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