Date
Details
Price
Change
Source
10/08/2026
Listed
$640,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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Property Description
Welcome to Highwood on the North Shore! Quality Built, One Owner, Lannon Stone ranch offers flexible living space, hardwood floors throughout, and two fireplaces that add warmth and character. The spacious, and light filled living room overlooks a beautiful park, while the separate dining room with rich slate flooring opens to the patio and connects to the kitchen. The house has generous closet space throughout with an attic running the length of the house for additional storage. The home features two bedrooms, a full hall bath, and a versatile paneled den that can alternatively serve as a home office, family room, or additional bedroom. A private three-room in-law suite provides excellent flexibility for extended family, guests, or integration into the main living space. Outside, enjoy a large, private fenced backyard ideal for entertaining, gardening, or relaxing. The attached two-car garage plus an additional detached two-car garage provide abundant parking and storage. Situated on a desirable oversize corner lot this home is just minutes from downtown Highwood, Metra service, popular restaurants, and Lake Michigan. Being sold "AS-IS" as part of an Estate. UNIQUE OPPORTUNITY to either update both units and rent out. Live on one side and rent the other. Or, personalize it making this home your own in the most sought after area of Highwood.
Full Property Details
Full Property Details for 27 Pleasant Ave
General
- Price: $640,000
- Taxes: $9,102 (2025)
- Status: Active
- Type: Multi-Family
- Source: MRED
- MLS ID: 12780913
- Updated: 10/8/2026
- Added to Site: 2 day(s) ago
Rental Information
- Complex Features: Park, Curbs, Street Paved
Interior
- Basement: Unfinished
Rooms
Bathrooms
- Total Bathrooms: 2
- Upper - Full Baths: 2
Bedrooms
- Total Bedrooms: 4
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 4
- Total Spaces: 4
- Parking Features: Garage Door Opener, Garage, Yes, Garage Owned, Attached, Detached
Location
- Area: Highwood
- County: Lake
- Township: Moraine
- Driving Directions: Prairie Ave W of Green Bay to Pleasant S to House. Corner of Michigan and Pleasant.
School Information
- School District: 112
- Elem School District: 112
- Midd School District: 112
- High School District: 113
- Elementary School: Oak Terrace Elementary School
- Middle School: Northwood Junior High School
- High School: Highland Park High School
- Private School: Highland Park High School
Heating & Cooling
- Heating Type: Natural Gas, Forced Air
Utilities
- Sewer: Public Sewer
- Water: Lake Michigan
Structural Information
- Architectural Info: Ranch
- Architectural Style: Ranch
- Construction: Stone
- Exterior Const.: Stone
- Basement: Yes
- Basement Desc.: Unfinished, Full
- Year Built: 1953
- Built Before 1978: Yes
Unit Information
- Units in Building: 2
Lot Features
- Lot Size Range: .25 to .49 Acre
- Lot Dimensions: 115 x 38 x 53 x 68 x 42 x 135
Financial Considerations
- Assessment Year: 1953
- Tax Amount: $9,102
- Tax Year: 2025
- Pays Sewer: Public Sewer
Disclosures and Reports
- Ownership: Fee Simple
- Property ID: 16154280070000
Buyer's Brokerage Compensation: 2.5%
Not binding unless confirmed by separate agreement among applicable parties.
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Meet the listing agents
Meet the listing agents
— 27 Pleasant Ave —
(847) 668-8449 mobile
(847) 433-5400 direct
(847) 208-4509 mobile
NMLS#: 1598647
Get Pre-Approved Today
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Schools
Schools serving 27 Pleasant Ave
School Districts:North Shore School District 112, Township High School District 113
| Name | Grades | Distance |
|---|---|---|
Wayne Thomas Elementary School 2939 Summit Avenue, Highland Park, IL 60035 | K-5 | 0.8 mi |
Northwood Jr High School 945 North Avenue, Highland Park, IL 60035 | 6-8 | 0.7 mi |
Highland Park High School 433 Vine Avenue, Highland Park, IL 60035 | 9-12 | 0.6 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 27 Pleasant Ave
Tax History
Tax History for 27 Pleasant Ave
Year
Property Taxes
Change
Tax Assessment
Change
2024
$8,598
8%
$129,052
6%
2024
$7,927
-22%
$121,667
11%
2023
$10,167
22%
$109,669
-14%
2022
$8,305
2%
$127,876
3%
2021
$8,112
4%
$123,611
—
2020
$7,802
—
$123,611
—
2019
$7,814
-8%
$123,033
-1%
2018
$8,528
14%
$124,047
1%
2017
$7,499
-8%
$123,332
5%
2016
$8,144
26%
$117,415
8%
2015
$6,464
-2%
$109,091
—
2014
$6,579
3%
$109,091
4%
2013
$6,398
5%
$105,307
-3%
2012
$6,083
—
$108,039
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 27 Pleasant Ave
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- Single Family
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- Active
- Updated 1 day ago
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- 8Total Baths
- 6,052Sq. Ft.
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- Multi-Family
- Closed
- 5Total Beds
Listed by Carol DeGrazia Santi and Brendan Santi
27 Pleasant Avenue, Highwood, IL 60040 (MLS# 12780913) is a Multi-Family property with 2 units containing 4 bedrooms and 0 full bathrooms. 27 Pleasant Avenue is currently listed for $640,000 and was received on October 08, 2026. This property is listed by Carol DeGrazia Santi from our Lake Forest Office.Want to learn more about 27 Pleasant Avenue? Do you have questions about finding other Multi-Family real estate for sale in Highwood? You can browse all Highwood real estate or contact a Coldwell Banker agent to request more information.