Photo: VitaleBaby at en.wikipedia · Public domain50 homes sold in Highland in the last year, at a typical $408K
About one sale in 5 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 Highland homes are listed.
Every place Highland 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 Highland.
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 72% of Highland’s sales, at a typical $444K
50 homes sold in the year to May 2026.
typical sale · 36 sold in 12 months
- Per square foot
- $246NY $316
- Days to sell
- 58
- Sold over asking
- 42%
- Listings with a price cut
- 24%
Multi-family (2–4 units): 3 sold, typical $520K
Townhouses: 9 sold, typical $321K
Condos: 2 sold, typical $326K
Too few sales in 12 months for reliable figures.
Fewer homes sell than before 2021, at 2.3 times the 2016 price
50 sales in the last year, against 94 in 2020 and a low of 48 in 2012. The typical sale went from $178K in 2016 to $408K.
Source: Redfin Data Center, MLS sales. Typical price and $/sq ft are the monthly medians, weighted by sales.
What $400K buys in Highland
Check a listing against what Highland 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 Highland are more common than before the pandemic, but 60% fewer homes come up for sale
We read every month of Highland’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, 50 sales.
If you’re buying in Highland
- Shop in May. It brings about 11 new listings a month, close to the busiest month, with fewer bidding wars (21% over asking).
- Bid near asking. Buyers paid 99.9% of the list price on average; 40% paid over.
- You’ll usually have time. Only 11% of homes go under contract within two weeks; the typical one takes 62 days.
Summer brings both the most homes and the most bidding wars
July has the most new listings (about 12 a month), and the most competition: 38% close over asking. May offers nearly as much choice with fewer homes bid up (21%). June has the least competition (17%).
Averages for each calendar month, 2015 on.
Nearly as heated as 2021, and about like New York as a whole
| Highland now | 2017–19 | 2021 peak | NY now | |
|---|---|---|---|---|
| Sold over askingShare of sales that closed above the list price | 40% | 17% | 31% | 41% |
| Gone within two weeksShare of homes under contract within 14 days | 11% | 0% | 7% | 26% |
| Listings with a price cutShare of homes for sale that cut their price | 17% | — | 11% | 20% |
| Price paid vs. askingAverage sale price ÷ list price | 99.9% | 97% | 98.7% | 101% |
| Days to sellMedian days from listing to contract | 62 | 131 | 111 | 41 |
16 homes for sale on a typical day
That’s 1.3 times the 2025 low (13), 60% fewer than in 2017–19 and well under 2015’s 68.
1 in 6 listings has cut its price
17% in the last year, against — in 2017–19 and 20% across New York.
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 Highland home costs about $2,712 a month
Price: Highland’s typical sale, last 12 months. Property tax at Highland’s 1.7% (median bill ÷ median value, Census ACS); insurance at 0.35% of price a year. Before PMI, HOA dues, upkeep and the tax deduction. Whether Highland is affordable on local pay is on Cost of living.
Six things worth knowing
New listings in July
The month with the most choice. December has the fewest, about 4.
Best time to buyProperty tax, a year
Of a home’s value: the median bill over the median home value. On a $408K home, about $7,000 a year.
Taxes vs. neighborsSchools
The schools grade for Highland, from test results, graduation and how much students grow.
Schools in HighlandTypical commute
The average one-way trip to work for people who live in Highland.
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.
Masthope, Fawn Lake Forest, Deerpark, Port Jervis, Pocono Woodland Lakes and Matamoras sell for less a square foot
The busier markets within 25 miles of Highland, 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 | |
|---|---|---|---|---|---|
| Port Jervis | 91 | $288K | $184 | 31% | 53 |
| Deerpark | 59 | $329K | $213 | 22% | 79 |
| Masthope | 58 | $405K | $184 | 9% | 43 |
| Highland | 50 | $408K | $235 | 40% | 62 |
| Pocono Woodland Lakes | 44 | $394K | $202 | 18% | 58 |
| Matamoras | 34 | $296K | $218 | 24% | 26 |
| Fawn Lake Forest | 32 | $322K | $180 | 6% | 75 |
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 Highland, free
Selling it yourself, renting out an apartment or looking for a roommate? Post it to Highland. People who follow the town see it, and so do people comparing Highland with their own town. No commission, no listing fee.
Questions about buying a home in Highland
What do homes sell for in Highland, NY?
50 homes sold in the year to May 2026 at a typical $408K, $235 a square foot.
Is Highland a buyer’s or seller’s market?
A buyer’s market: 34 homes were for sale in May 2026 and 3 sold, about 11.3 months of supply. Buyers paid 99.9% of asking on average, and 17% of listings cut their price.
When is the best time to buy in Highland?
July brings the most new listings. The sales history shows which months have fewer bidding wars.
How much are property taxes in Highland?
About 1.7% of a home’s value a year. On a $408K home that’s near $7,000.
Where can I see homes for sale in Highland?
Zillow, Redfin, Realtor.com and Homes.com all carry Highland’s MLS listings; the search links above open each one filtered to Highland.
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).