399 Jackson Ave, Glencoe, IL 60022
Property image
Property image
OFF MARKET

399 Jackson Ave
Glencoe, IL 60022

  • 4 Beds
  • 2.5 Baths
  • 2,088 sqft

$1,002,200

Trulia Estimate
as of Aug 18, 2026
Est. Refi. Payment $6,863/mo*
Refinance Your Home

$1,002,200

Trulia Estimate
as of Aug 18, 2026
Est. Refi. Payment $6,863/mo*
Refinance Your Home
4 Beds
2.5 Baths
2,088 sqft

Home Value

Trulia Estimate
$1M
Since last month
Increased$18K (+1.8%)
Since last year
Increased$127K (+14.2%)
Since last sale
Increased$415K (+68.7%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +64% in the last 10 years
MonthEstimated value
2026
August 2026$1.02M
July 2026$1M
June 2026$1.02M
May 2026$1.01M
April 2026$995K
March 2026$982K
February 2026$930K
January 2026$910K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
503 Oakdale Ave, Glencoe, IL
0.20
Single-Family Home
$1,200,000
10/10/25
4
3
2,289
454 Drexel Ave, Glencoe, IL
0.24
Single-Family Home
$1,110,000
09/15/25
4
2.5
2,366
499 Oakdale Ave, Glencoe, IL
0.20
Single-Family Home
$840,000
05/27/26
3
2
2,108
491 Drexel Ave, Glencoe, IL
0.22
Single-Family Home
$1,325,000
07/31/26
4
2.5
2,219
451 Jackson Ave, Glencoe, IL
0.12
Single-Family Home
$1,421,000
07/15/26
4
5
2,440
285 Vernon Ave, Glencoe, IL
0.19
Single-Family Home
$1,400,000
02/20/26
4
3.5
2,732
154 Glenwood Ave, Winnetka, IL
0.31
Single-Family Home
$1,230,154
08/11/26
3
2
2,333
1409 Asbury Ave, Winnetka, IL
0.40
Single-Family Home
$1,040,000
12/05/25
4
2.5
3,434
274 Mary St, Winnetka, IL
0.26
Single-Family Home
$1,550,000
06/09/26
3
4
2,309
426 Madison Ave, Glencoe, IL
0.20
Single-Family Home
$1,690,000
08/20/25
5
3.5
2,982

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
392 Jackson Ave, Glencoe, IL 60022
0.05
$1,999,800
5
4.5
3,433
Off Market
399 Woodlawn Ave, Glencoe, IL 60022
0.08
$2,428,400
5
4.5
4,152
Off Market
265 Randolph St, Glencoe, IL 60022
0.07
$1,430,000
5
3
-
Recently Sold
437 Woodlawn Ave, Glencoe, IL 60022
0.09
$1,403,800
5
3.5
3,437
Off Market
446 Jackson Ave, Glencoe, IL 60022
0.11
$1,869,600
5
4.5
3,695
Off Market
195 Lake St, Glencoe, IL 60022
0.15
$2,411,400
5
4.5
3,546
Off Market
443 Jackson Ave, Glencoe, IL 60022
0.10
$3,138,800
6
6.5
4,932
Off Market
235 Linden Ave, Glencoe, IL 60022
0.15
$755,500
3
1.5
1,540
Off Market
465 Woodlawn Ave, Glencoe, IL 60022
0.13
$1,971,800
5
4.5
-
Off Market
457 Jackson Ave, Glencoe, IL 60022
0.13
$2,262,300
4
4
3,000
Off Market
430 Oakdale Ave, Glencoe, IL 60022
0.18
$1,646,200
4
2.5
3,365
Off Market
464 Jackson Ave, Glencoe, IL 60022
0.15
$1,973,100
5
5.5
4,614
Off Market

Local Information

  • Map ViewExplore the area around 399 Jackson Ave.
  • Schools1 Preschool School3 Elementary Schools2 Middle Schools2 High Schools
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1928
Living Area
2,088 sqft
Price/Sqft
$480
Parking
Garage

About this House

This charming brick home located on the President streets of Glencoe combines indoor and outdoor living to perfection. The front door entryway flows into a welcoming family room with hardwood flooring and recessed lighting. Arched doorways surround a spacious living room, complete with vintage crown molding, custom built-ins and a showcase wood-burning fireplace. Stainless steel appliances, granite countertops and ample cabinetry produce a stunning gourmet kitchen with direct access to the private deck overlooking the professionally landscaped backyard. Three bedrooms on the second level includes a traditional master-suite with an attached sun-drenched deck. Finished basement with additional bedroom and laundry room. Adjacent to South School and Watts Park. Minutes from great restaurants and shopping in Downtown Glencoe. Just blocks from Hubbard Woods train station. A remarkable home in a wonderful location!
399 Jackson Ave, Glencoe, IL 60022 is a 4 bedroom, 3 bathroom, 2,088 sqft single-family home built in 1928. It last sold for $605,000 on Oct 8, 2020. It is currently off market. The Trulia Estimate is $1,002,200, with a rent estimate of $4,066/month.

Home Details for 399 Jackson Ave

Interior Features

Heating & Cooling
Heating: Baseboard, GasAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Interior Details
Number of Rooms: 8Types of Rooms: Walk In Closet, Dining Room
Appliances & Utilities
DishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Levels, Entrance, & Accessibility
Floors: Carpet, Hardwood

Exterior Features

Exterior Home Features
Roof: Asphalt, OtherDeckExterior: Brick
Parking & Garage
GarageParking Space: 1Parking: Garage Detached

Property Information

Year Built
Year Built: 1928
Property Type / Style
Property Type: Single Family HomeArchitecture: Tudor

Community

Units in Building: 1

Lot Information

Lot Area: 9104 sqft

Building

Fitness & Sports
Tennis Court

Price and Tax history

DateEventPrice
Oct 8, 2020
Source: N/A
Sold
$605,000
Jul 8, 2020
Source: MRED as distributed by MLS GRID #10730985
Sold
$605,000
Jul 8, 2020
Source: Agent Provided
PendingToActive
$600,000
Jun 2, 2020
Source: Agent Provided
Pending
$600,000
Jun 1, 2020
Source: Agent Provided
Listed For Sale
$600,000

Market trends in Glencoe

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
40
1MoM
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Around this home

View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Glencoe

At least 51 Trulia users voted on each feature.

  • 98 % Say it's dog friendly

  • 91 % Say people would walk alone at night

  • 89 % Say there are sidewalks

  • 86 % Say yards are well-kept

  • 85 % Say kids play outside

  • 84 % Say there's holiday spirit

  • 82 % Say parking is easy

  • 82 % Say there's wildlife

  • 80 % Say it's walkable to restaurants

  • 76 % Say it's quiet

  • 76 % Say car is needed

  • 70 % Say streets are well-lit

  • 69 % Say they plan to stay for at least 5 years

  • 67 % Say neighbors are friendly

  • 65 % Say it's walkable to grocery stores

  • 60 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Leo.garcia.5251
    "The community puts together fantastic events for families during holidays and have their independent special events which cater to everyone’s wants and needs I’ve never felt more at home in this community. "
    1
    Flag
  • Cristinaisabelle
    "I live in this neighborhood. Some of the best year-round programs for kids as well as great schools. Also a family friendly town with many events to bring people together. "
    0
    Flag
  • Shert929
    "The schools here are great. Tariff Center offers something for everyone. There’s a few great grocery stores and you’re close to the beach. Most of all it’s a quiet and safe area to live in. And as a bonus, Glencoe is close to Ravinia to see concerts and near to Highland Park. "
    0
    Flag
  • mcsampson
    "Great schools, parks and kids activities. The park district offers day care, after school activities and various camps. Glencoe also has a beach! "
    0
    Flag
  • Shert929
    "Most places here are dog friendly accept for the condos. Plenty of places to walk a dog. Great community for pets and people. "
    0
    Flag
  • Ji
    "Lovely street, a lot of greenery, friendly neighbors. Walking distance to lake,town and train. Schools are terrific and beautiful parks for families and young children."
    0
    Flag
  • gladnowtravel
    "It is a small, tight-knit community with phenomal schools, negligent crime, a remarkably attentive police force, nearby train service, a large forest preserve, two golf courses and a nationally reknown botanical garden, all within blocks of expressway access to downtown Chicago or other suburbs."
    0
    Flag
  • Deborah B.
    "This is a lovely Community with old fashioned values. Jens Jensen Landscaping delight local parks. "
    1
    Flag

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Apartments for Rent

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Explore by feature - Air Conditioning

6 rentals with air conditioning in Glencoe, IL

Explore by feature - Washer/dryer

7 rentals with a washer/dryer in Glencoe, IL

Homes for sale near 399 Jackson Ave

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Off Market Homes Near 399 Jackson Ave

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Frequently asked questions about 399 Jackson Ave

  • What is 399 Jackson Ave estimated to be worth?
    Trulia's estimated value for 399 Jackson Ave in Glencoe, IL is $1,002,200.
  • What is the price history for 399 Jackson Ave?
    399 Jackson Ave in Glencoe, IL last sold for $605,000 in October 2020.
  • Is Glencoe a buyer's or seller's market?
    Glencoe is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Glencoe?
    Residents describe Glencoe, IL as dog-friendly, pedestrian-friendly, and well-kept. See recently sold homes in Glencoe, IL.
  • Does 399 Jackson Ave have air conditioning?
    Yes, 399 Jackson Ave in Glencoe, IL has air conditioning.
  • Does 399 Jackson Ave have laundry facilities?
    Yes, 399 Jackson Ave in Glencoe, IL has in-unit laundry.