5 Bedroom Homes in Highland Park, IL

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3 beds New construction With a pool

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20 Listings

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5 Bedroom Homes in Highland Park, IL

20 Listings

New27

20 listings

5 Bedroom Homes in Highland Park, IL

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20 Listings

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5 Bedroom Homes in Highland Park, IL

20 Listings

Your local brokerage

Jeffrey Jonas

Realty.com

Lic. #471.004966

Call Jeffrey

New27

Your local brokerage

Jeffrey Jonas

Realty.com

Lic. #471.004966

Call Jeffrey

Active

$2,500,000

5 bd · 7 ba · 5,072 sqft

701 Lincoln Avenue W, Highland Park, IL

Beth Wexler · @properties Christie's International Real Estate

40Active

$1,650,000

5 bd · 6 ba · 4,748 sqft

767 Whiteoaks Lane, Highland Park, IL

Janet Borden · Compass

40Active

$1,650,000

5 bd · 6 ba · 4,748 sqft

767 Whiteoaks Lane, Highland Park, IL

Janet Borden · Compass

Your local brokerage

Jeffrey Jonas

Realty.com

Lic. #471.004966

Call Jeffrey

29Active

$994,000

5 bd · 6 ba · 4,065 sqft

201 Aspen Lane, Highland Park, IL

Gloria Matlin · Compass

29Active

$994,000

5 bd · 6 ba · 4,065 sqft

201 Aspen Lane, Highland Park, IL

Gloria Matlin · Compass

35Active

$850,000

5 bd · 3 ba · 2,624 sqft

822 Timber Hill Road, Highland Park, IL

Nancy Karp · @properties Christie's International Real Estate

35Active

$850,000

5 bd · 3 ba · 2,624 sqft

822 Timber Hill Road, Highland Park, IL

Nancy Karp · @properties Christie's International Real Estate

58Active

$3,350,000

5 bd · 7 ba · 0 sqft

1008 Bob O Link Road, Highland Park, IL

Joshua Lipton · Compass

58Active

$3,350,000

5 bd · 7 ba · — sqft

1008 Bob O Link Road, Highland Park, IL

Joshua Lipton · Compass

57Active

$1,675,000

5 bd · 9 ba · 5,339 sqft

1745 Sundrop Circle, Highland Park, IL

Rita Masini · Compass

57Active

$1,675,000

5 bd · 9 ba · 5,339 sqft

1745 Sundrop Circle, Highland Park, IL

Rita Masini · Compass

36Active

$2,500,000

5 bd · 4 ba · 5,443 sqft

89 Cary Avenue, Highland Park, IL

Ted Pickus · @properties Christie's International Real Estate

36Active

$2,500,000

5 bd · 4 ba · 5,443 sqft

89 Cary Avenue, Highland Park, IL

Ted Pickus · @properties Christie's International Real Estate

27Active

$2,500,000

5 bd · 7 ba · 5,072 sqft

701 Lincoln Avenue W, Highland Park, IL

Beth Wexler · @properties Christie's International Real Estate

27Active

$2,500,000

5 bd · 7 ba · 5,072 sqft

701 Lincoln Avenue W, Highland Park, IL

Beth Wexler · @properties Christie's International Real Estate

16Active

$4,399,000

5 bd · 6 ba · — sqft

966 Wade Street, Highland Park, IL

William Goldberg · Fulton Grace Realty

36Active

$1,095,000

5 bd · 6 ba · 3,396 sqft

2925 Parkside Drive, Highland Park, IL

Beth Wexler · @properties Christie's International Real Estate

36Active

$1,095,000

5 bd · 6 ba · 3,396 sqft

2925 Parkside Drive, Highland Park, IL

Beth Wexler · @properties Christie's International Real Estate

71Active

$6,750,000

5 bd · 9 ba · 8,186 sqft

117 Belle Avenue, Highland Park, IL

Beth Wexler · @properties Christie's International Real Estate

71Active

$6,750,000

5 bd · 9 ba · 8,186 sqft

117 Belle Avenue, Highland Park, IL

Beth Wexler · @properties Christie's International Real Estate

Listing data & MLS disclosures

Midwest Real Estate Data (MRED): Based on information submitted to the MLS GRID as of 2026-09-28 21:12:04 UTC. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Highland Park housing market

August 2026

Selling at 100.0% of asking price

Sales here are closing essentially at asking. MLS · 29 sales · as of Aug 31, 2026

Homes that sold · County records, as of Aug 28, 2026

Median sale price: $645,000$60,000–$1,210,000 typical range
Price per sq. ft.: $338
Sales: 61
Paid in cash: 50.8%

Homes on the market · MLS, as of Aug 31, 2026

Median days on market: 18 days

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

Year-over-year: -20.1%

Highland Park, IL community profile

Population: 30,368
Median income: $157,988
Housing units: 12,180
People per sq. mi.: 1,959.2
Area: 15.5 sq. mi.

Source: HJN community data

Explore Highland Park homes

Your local brokerage

Jeffrey Jonas

Realty.com

Lic. #471.004966

Call Jeffrey

Listing data & MLS disclosures

Midwest Real Estate Data (MRED): Based on information submitted to the MLS GRID as of 2026-09-28 21:12:04 UTC. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Highland Park, IL community profile

Population: 30,368
Median income: $157,988
Housing units: 12,180
People per sq. mi.: 1,959.2
Area: 15.5 sq. mi.

Source: HJN community data

Highland Park housing market

August 2026

Selling at 100.0% of asking price

Sales here are closing essentially at asking. MLS · 29 sales · as of Aug 31, 2026

Homes that sold · County records, as of Aug 28, 2026

Median sale price: $645,000$60,000–$1,210,000 typical range
Price per sq. ft.: $338
Sales: 61
Paid in cash: 50.8%

Homes on the market · MLS, as of Aug 31, 2026

Median days on market: 18 days

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

Year-over-year: -20.1%

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Registered offenders on the map

Your local brokerage

Your local brokerage

Your local brokerage

Listing data & MLS disclosures

Highland Park housing market

Homes that sold · County records, as of Aug 28, 2026

Homes on the market · MLS, as of Aug 31, 2026

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

Highland Park, IL community profile

Explore Highland Park homes

Your local brokerage

Listing data & MLS disclosures

Highland Park, IL community profile

Highland Park housing market

Homes that sold · County records, as of Aug 28, 2026

Homes on the market · MLS, as of Aug 31, 2026

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