Homes Under $500K in Highland, NY

Save search

3 beds New construction With a pool

Hide Map

22 of 28 Listings

Map

Homes Under $500K in Highland, NY

22 of 28 Listings

28Active

28 listings

Homes Under $500K in Highland, NY

Hide Map

22 of 28 Listings

Map

Homes Under $500K in Highland, NY

22 of 28 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas

28Active

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas

$419,000

3 bd · 2 ba · 1,344 sqft

53 Devlin Road, Highland, NY

Edward Rabon · Compass Greater NY, LLC

42Active

$493,000

3 bd · 3 ba · 1,456 sqft

44 Airport Road, Highland, NY

Caroline Akt · Caroline Akt Realty LLC

42Active

$449,000

4 bd · 3 ba · 3,194 sqft

66 Highland Lake Road, Highland, NY

Michael Friedmann · eRealty Advisors, Inc

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas

36Active

$389,000

3 bd · 2 ba · 1,500 sqft

943 State Route 55, Highland, NY

Joy Romano · Joy Romano Realty

7Active

$145,600

2 bd · 1 ba · 1,440 sqft

3426 State Route 97, Highland, NY

Jamarr C. Zellner · REALHome Services & Solutions

Price Reduced13Active

$250,000

3 bd · 2 ba · 960 sqft

24 Frazier Road, Highland, NY

Sean Walker · Keller Williams Realty

27Active

$385,000

2 bd · 1 ba · 1,092 sqft

3 Rennenberg Road, Highland, NY

Donna M Geba · Century 21 Geba Realty

Price Reduced21Active

$339,000

3 bd · 2 ba · 1,252 sqft

220 Mail Road, Highland, NY

Loretta Wolff · NexLvl Real Estate Inc.

Price Reduced37Active

$180,000

1 bd · 1 ba · 777 sqft

223 Yulan-Barryville Road, Highland, NY

Barry Becker · KW Hudson Valley United

50Active

$399,900

3 bd · 2 ba · 1,430 sqft

91 Airport Road, Highland, NY

Patti Martell · Payne Team LLC

23Active

$379,000

3 bd · 2 ba · 1,384 sqft

171 Yulan Barryville Road, Highland, NY

Chris C. Somerville · Cabins & Canoes Real Estate

Price Reduced33Active

$449,999

3 bd · 2 ba · 1,560 sqft

60 Highland Lake Road, Highland, NY

Pedrina Martinez · Listing Pro Realty Services

Price Reduced45Active

$425,000

4 bd · 3 ba · 2,240 sqft

142 Split Rock Drive, Highland, NY

Alan R. Wieder · Catskills Home Services

19Active

$249,000

3 bd · 1 ba · 1,008 sqft

5 Steges Road, Highland, NY

Dali Levy · KW Hudson Valley United

Price Reduced31Active

$405,000

2 bd · 1 ba · 1,300 sqft

80 Beaver Brook Road, Highland, NY

Dawn J. Curreri · Eagle Valley Realty

37Active

$485,000

0 bd · 2 ba · 5,600 sqft

17 Collins Road, Highland, NY

Donna M Geba · Century 21 Geba Realty

Price Reduced40Active

$390,000

2 bd · 1 ba · 1,008 sqft

30 Woods Road, Highland, NY

Myra F. Rappoport · Payne Team LLC

Price Reduced20Active

$409,000

2 bd · 1 ba · 828 sqft

3 Perry Road, Highland, NY

Jonathan Sunshine · The Sunshine Group Real Estate

40Active

$499,000

3 bd · 2 ba · 1,632 sqft

16 Fairway Drive, Highland, NY

Dawn M. Payne · Payne Team LLC

Price Reduced38Active

$319,000

3 bd · 2 ba · 1,664 sqft

114 Proctor Road, Highland, NY

Dawn M. Payne · Payne Team LLC

Price Reduced31Active

$329,000

3 bd · 3 ba · 2,000 sqft

87 Airport Road, Highland, NY

Donna M Geba · Century 21 Geba Realty

Price Reduced18Active

$425,000

4 bd · 2 ba · 1,680 sqft

36 Highland Lake Road, Highland, NY

Gibson E Mc Kean · Gibson E McKean Inc

Listing data & MLS disclosures

OneKey MLS: The data relating to real estate for sale on this website comes in part from the Internet Data exchange of OneKey MLS. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed. Copyright © 2026 OneKey MLS. All Rights Reserved

Highland housing market

August 2026 · This period is still settling

Homes that sold · County records, as of Aug 25, 2026

Median sale price: $265,000$184,500–$431,250 typical range
Sales: 11
Paid in cash: 54.6%

Homes on the market · MLS, as of Aug 24, 2026

Median list price: $547,500
Homes for sale: 26

Price trend · Assessor repeat sales, as of Aug 31, 2026

Year-over-year: -28.4%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Aug 20, 2026

Median home size: 1,710 sq. ft.

Highland, NY community profile

Area: 46.6 sq. mi.

Source: HJN community data

Explore Highland homes

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas

Listing data & MLS disclosures

OneKey MLS: The data relating to real estate for sale on this website comes in part from the Internet Data exchange of OneKey MLS. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed. Copyright © 2026 OneKey MLS. All Rights Reserved

Highland, NY community profile

Area: 46.6 sq. mi.

Source: HJN community data

Highland housing market

August 2026 · This period is still settling

Homes that sold · County records, as of Aug 25, 2026

Median sale price: $265,000$184,500–$431,250 typical range
Sales: 11
Paid in cash: 54.6%

Homes on the market · MLS, as of Aug 24, 2026

Median list price: $547,500
Homes for sale: 26

Price trend · Assessor repeat sales, as of Aug 31, 2026

Year-over-year: -28.4%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Aug 20, 2026

Median home size: 1,710 sq. ft.

Registered offenders on the map

Registered offenders on the map

Registered offenders on the map

Registered offenders on the map

Your local brokerage

Your local brokerage

Your local brokerage

Listing data & MLS disclosures

Highland housing market

Homes that sold · County records, as of Aug 25, 2026

Homes on the market · MLS, as of Aug 24, 2026

Price trend · Assessor repeat sales, as of Aug 31, 2026

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Aug 20, 2026

Highland, NY community profile

Explore Highland homes

Your local brokerage

Listing data & MLS disclosures

Highland, NY community profile

Highland housing market

Homes that sold · County records, as of Aug 25, 2026

Homes on the market · MLS, as of Aug 24, 2026

Price trend · Assessor repeat sales, as of Aug 31, 2026

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Aug 20, 2026