Photo: Etombari · CC BY-SA 4.032 homes sold in Highwood in the last year, at a typical $435K
About one sale in 3 is a condo. Below: what each kind of home sells for, what your budget buys, the best months to buy, how hard you’ll have to bid, and a shortcut to every site where Highwood homes are listed.
Every place Highwood homes are listed, in one stop
We don’t copy listings: the agents’ sites have the photos and the latest price changes. Set what you want once and we open each site already filtered to Highwood.
For sale
Rent
New, land & open houses
Links open the listing sites; TownRatings isn’t paid for them and doesn’t rank one above another. Rentals and government-owned homes come from sources outside the MLS.
Houses are 59% of Highwood’s sales, at a typical $444K
32 homes sold in the year to May 2026.
typical sale · 19 sold in 12 months
- Per square foot
- $269IL $180
- Days to sell
- 68
- Sold over asking
- 37%
- Listings with a price cut
- 32%
Multi-family (2–4 units): 2 sold, typical $513K
Townhouses: 6 sold, typical $742K
Condos: 5 sold, typical $495K
Too few sales in 12 months for reliable figures.
Fewer homes sell than a decade ago, at 1.3 times the 2016 price
32 sales in the last year, against 58 in 2014 and a low of 28 in 2012. The typical sale went from $346K in 2016 to $435K.
Source: Redfin Data Center, MLS sales. Typical price and $/sq ft are the monthly medians, weighted by sales.
What $450K buys in Highwood
Check a listing against what Highwood homes sold for
Against the town’s median price per square foot over the last 12 months. A rough check: condition, lot and location within town move a price more than this can see.
Bidding wars in Highwood are more common than before the pandemic, but three quarters fewer homes come up for sale
We read every month of Highwood’s home sales since 2012 so you don’t have to. Each figure covers 12 months, because a single month in a town is too few sales to mean much. Latest: the year to May 2026, 32 sales.
If you’re buying in Highwood
- Shop in May. It brings about 6 new listings a month, close to the busiest month, with fewer bidding wars (19% over asking).
- You can negotiate. 31% of listings have cut their price, against 19% before the pandemic.
- Bid near asking. Buyers paid 99.4% of the list price on average; 41% paid over.
- You’ll usually have time. Only 39% of homes go under contract within two weeks; the typical one takes 49 days.
Spring brings the homes; summer brings the bidding wars
March has the most new listings (about 7 a month), but July is the most competitive: 31% of July sales close over asking. May offers nearly as much choice with fewer homes bid up (19%). December has the least competition (6%) but only about 1 new listings.
Averages for each calendar month, 2015 on.
Hotter than in 2021, and about like Illinois as a whole
| Highwood now | 2017–19 | 2021 peak | IL now | |
|---|---|---|---|---|
| Sold over askingShare of sales that closed above the list price | 41% | 8% | 13% | 37% |
| Gone within two weeksShare of homes under contract within 14 days | 39% | 23% | 37% | 46% |
| Listings with a price cutShare of homes for sale that cut their price | 31% | 19% | 39% | 19% |
| Price paid vs. askingAverage sale price ÷ list price | 99.4% | 95.1% | 97.8% | 99.2% |
| Days to sellMedian days from listing to contract | 49 | 122 | 46 | 49 |
5 homes for sale on a typical day
That’s 74% fewer than in 2017–19 and well under 2019’s 24.
1 in 3 listings has cut its price
31% in the last year, against 19% in 2017–19 and 19% across Illinois. More sellers are pricing high and coming down.
Since 2019, houses are up 47%, condos 198%
A house typically sold for $444K in the last year (19 sales), a condo for $495K (5).
Median sale price, weighted by sales each month. Years with fewer than 4 sales of a type are left out.
Source: Redfin Data Center, city market tracker, January 2012 to May 2026 (MLS sales, not seasonally adjusted). Ratios are weighted by homes sold; price cuts by homes for sale.
Owning the typical Highwood home costs about $3,089 a month
Price: Highwood’s typical sale, last 12 months. Property tax at Highwood’s 2.3% (median bill ÷ median value, Census ACS); insurance at 0.35% of price a year. Before PMI, HOA dues, upkeep and the tax deduction. Whether Highwood is affordable on local pay is on Cost of living.
Six things worth knowing
New listings in March
The month with the most choice. December has the fewest, about 1.
Best time to buyProperty tax, a year
Of a home’s value: the median bill over the median home value. On a $435K home, about $9,830 a year.
Taxes vs. neighborsSchools
The schools grade for Highwood, from test results, graduation and how much students grow.
Schools in HighwoodTypical commute
The average one-way trip to work for people who live in Highwood.
Work & commuteCheck the flood map
Flood insurance isn’t in a standard policy, and lenders require it in FEMA flood zones. Check the address before you make an offer.
Natural hazardsLook up any property
Assessed value, lot size and every past sale of a home you’re eyeing are public, at the town or county assessor and the registry of deeds.
No busy market nearby sells for less a square foot; Lake Forest for far more
The busier markets within 25 miles of Highwood, by what sold. Prices, taxes and how far a paycheck goes next door are on Cost of living.
| Sold | Typical sale | $/sq ft | Over asking | Days to sell | |
|---|---|---|---|---|---|
| Northbrook | 487 | $697K | $295 | 45% | 48 |
| Highland Park | 429 | $796K | $299 | 47% | 44 |
| Lake Forest | 316 | $1.2M | $369 | 35% | 60 |
| Deerfield | 248 | $703K | $299 | 45% | 49 |
| Lincolnshire | 104 | $751K | $262 | 44% | 65 |
| Riverwoods | 45 | $949K | $281 | 38% | 43 |
| Highwood | 32 | $435K | $259 | 41% | 49 |
Redfin Data Center, June 2025 to May 2026. Towns with fewer than 20 sales are left out, and Redfin doesn’t report every town separately.
Post your home to Highwood, free
Selling it yourself, renting out an apartment or looking for a roommate? Post it to Highwood. People who follow the town see it, and so do people comparing Highwood with their own town. No commission, no listing fee.
Questions about buying a home in Highwood
What do homes sell for in Highwood, IL?
32 homes sold in the year to May 2026 at a typical $435K, $259 a square foot.
Is Highwood a buyer’s or seller’s market?
A balanced market: 12 homes were for sale in May 2026 and 3 sold, about 4 months of supply. Buyers paid 99.4% of asking on average, and 31% of listings cut their price.
When is the best time to buy in Highwood?
March brings the most new listings. The sales history shows which months have fewer bidding wars.
How much are property taxes in Highwood?
About 2.3% of a home’s value a year. On a $435K home that’s near $9,830.
Where can I see homes for sale in Highwood?
Zillow, Redfin, Realtor.com and Homes.com all carry Highwood’s MLS listings; the search links above open each one filtered to Highwood.
Sales, prices, days on market and listings: Redfin Data Center (MLS, monthly, not seasonally adjusted). Property tax rate: Census American Community Survey. Two-bedroom rent: HUD Fair Market Rent. Typical home value: Zillow Home Value Index. Schools grade: TownRatings (how grades work).