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 legal non conforming apartment/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.
Contingent
Price cut: $35K (10/8)
$640,000
27 Pleasant Ave, Highwood, IL 60040
4beds
--sqft
Multi Family
Built in 1953
-- sqft lot
$631,300 Zestimate®
$--/sqft
$-- HOA
What's special
Lannon stone ranchFull hall bathAttached two-car garageAdditional detached two-car garageDesirable oversize corner lotTwo bedroomsHardwood floors throughout
- 7 days
- 266
- 17
Zillow last checked:
Listing updated:
Listed by:
Carol DeGrazia Santi, ABR,CRS (847)668-8449,
Coldwell Banker Realty,
Brendan Santi,
Coldwell Banker Realty
Source: MRED as distributed by MLS GRID,MLS#: 12780913
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 2
- Full bathrooms: 2
Heating
- Natural Gas, Forced Air
Features
- Basement: Unfinished,Full
Property
Parking
- Total spaces: 4
- Parking features: Garage Door Opener, Garage, Yes, Garage Owned, Attached, Detached
- Attached garage spaces: 4
- Has uncovered spaces: Yes
Lot
- Dimensions: 115x38x53x68x42x135
Details
- Parcel number: 16154280070000
- Special conditions: None
Construction
Type & style
- Home type: MultiFamily
- Architectural style: Ranch
- Property subtype: Multi Family
Materials
- Stone
Condition
- New construction: No
- Year built: 1953
Utilities & green energy
- Sewer: Public Sewer
- Water: Lake Michigan
Community & HOA
Community
- Features: Park, Curbs, Street Paved
Location
- Region: Highwood
Financial & listing details
- Tax assessed value: $365,038
- Annual tax amount: $9,102
- Date on market: 10/8/2026
- Ownership: Fee Simple
Estimated market value
$631,300
$600,000 - $663,000
$3,215/mo
Price history
| Date | Event | Price |
|---|---|---|
| 10/12/2026 | Contingent | $640,000 |
Source: | ||
| 10/8/2026 | Price change | $640,000-5.2% |
Source: | ||
| 9/28/2026 | Price change | $675,000-3.4% |
Source: | ||
| 9/3/2026 | Listed for sale | $699,000 |
Source: | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $8,598 +8.3% | $129,052 +6.1% |
| 2023 | $7,938 -22% | $121,667 +10.9% |
| 2022 | $10,178 +22.4% | $109,669 -14.2% |
| 2021 | $8,313 +2.3% | $127,876 +3.5% |
| 2020 | $8,123 +4% | $123,611 +0.5% |
| 2019 | $7,814 +4.2% | $123,033 +11.2% |
| 2018 | $7,499 | $110,625 -10.3% |
| 2017 | $7,499 +16.2% | $123,332 +5% |
| 2016 | $6,452 -1.8% | $117,415 +7.6% |
| 2015 | $6,568 +2.8% | $109,091 +3.6% |
| 2014 | $6,387 +5.2% | $105,307 -0.6% |
| 2012 | $6,071 +5.7% | $105,921 -15.4% |
| 2011 | $5,745 +12.9% | $125,182 -14.5% |
| 2010 | $5,088 +7.5% | $146,423 -5.6% |
| 2009 | $4,732 -42.4% | $155,175 -1% |
| 2008 | $8,221 +78.6% | $156,742 +4.8% |
| 2006 | $4,603 -3.3% | $149,634 |
| 2005 | $4,761 -4.5% | -- |
| 2004 | $4,984 -6% | -- |
| 2003 | $5,304 -3.7% | -- |
| 2002 | $5,507 +0.8% | -- |
| 2001 | $5,464 +7.5% | $90,191 +12.5% |
| 2000 | $5,081 | $80,203 |
Find assessor info on the county website
Monthly payment
Est. payment
Payment breakdown
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Neighborhood: 60040
Nearby schools
Schools provided by the listing agent
- Elementary: Oak Terrace Elementary School
- Middle: Northwood Junior High School
- High: Highland Park High School
- District: 112
Source: MRED as distributed by MLS GRID. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.



