Top 10 Most Expensive Streets in Jefferson Park, Chicago, IL

Lincoln Avenue is the 1st most expensive street in Chicago. It has condos, townhouses, multi-units, and land built from 1911 to 2025, ranging in price from $270,000 to $1,650,000. It is home to the Lincoln Crossing, Plaza Vista, The Pointe, Lincoln Park Terrace, 5300 N. Lincoln, Delta On Lincoln, Ivy Lane, 2626 N. Lincoln, The Chelsea, 5067 N Lincoln, 4050 N. Lincoln, Palace Lofts, 5003 N. Lincoln, 4114 N. Lincoln, 3151 N. Lincoln, Walpole Point, 2936 N. Lincoln, 4152 N. Lincoln, Lincoln Square Ravenswood, Vinery Lofts, Emerald City, Lincoln Point, 2843 N. Lincoln, Lincoln Theater Lofts, The Chaville, 4949 N. Lincoln, 4118 N. Lincoln, 3118 N. Lincoln, Seminary Court, 5061 N. Lincoln Avenue North, 2474 N. Lincoln, 2461 N. Lincoln, 3530 N. Lincoln, 3808 N. Lincoln, The Lincoln, Atrium at Lincoln, 3057 N. Lincoln, 3325 N. Lincoln, 2039 N. Lincoln, 2140 N. Lincoln, Bowmanville, and 2800 N. Lincoln Avenue subdivisions.

Oak Street is the 2nd most expensive street in Chicago. It has condos and townhouses built from 1995 to 2015, ranging in price from $435,000 to $3,200,000. It is home to the 30 W. Oak, Oak Club Condos, and Oak Street Terrace subdivisions.

Huron Street is the 3rd most expensive street in Chicago. It has condos, single-family homes, townhouses, land, and multi-units built from 1891 to 2026, ranging in price from $16,000 to $4,500,000. It is home to the 451 Huron Condos, The Pinnacle, Huron Pointe, Huron Street Lofts, Chicago Place, 30 East Huron, Hermitage, 30 E. Huron, Tuxedo Park, 1322 W. Huron, 33 W. Huron, Montreux Condos, River North Commons, 950 W. Huron, Noble Square, 1508 W. Huron, 400 W. Huron, 2330 W. Huron, 945 W. Huron, 56 W. Huron, 351 W. Huron, 2258 W. Huron, River West Courts, and 1748 W. Huron subdivisions.

Monroe Street is the 4th most expensive street in Chicago. It has condos, townhouses, land, single-family homes, and multi-units built from 1912 to 2021, ranging in price from $12,000 to $3,200,000. It is home to the The Flats on Monroe, 1228 W. Monroe, 955 W. Monroe, Park 1500 Lofts, 950 West Monroe, Monroe Manor, The Metro, 1526 W. Monroe, Park Monroe, 2212 W. Monroe, Metropolis Condominiums, Carmichael Place, The Legacy at Millennium Park, 1148 W. Monroe, 1234 W. Monroe, Block Y, 2136 W. Monroe St., Mentor Building, 1000 W. Monroe, Chelsea Townhomes, 1244 W. Monroe, Westhaven Park, 1400 W. Monroe, and Metropolitan Place subdivisions.

Fairbanks Court is the 5th most expensive street in Chicago. It has condos and land built from 2003 to 2008, ranging in price from $30,000 to $1,250,000. It is home to the 600 North Fairbanks subdivision.

Prairie Avenue is the 6th most expensive street in Chicago. It has condos, townhouses, single-family homes, land, and multi-units built from 1923 to 2025, ranging in price from $20,000 to $1,530,000. It is home to the One Museum Park West, Prairie House, Museum Park Towers, Prairie Pointe, Museum Park Tower IV, 4543 S. Prairie, One Museum Park, 4829 S. Prairie, 4854 S. Prairie, 4858 S. Prairie, 1717 S. Prairie, Prairie Place, Prairie District Homes, 1600 Museum Park, 4109 S. Prairie, Prairie Court, Prairie District Tower, Park Manor, Museum Park Place, 3541 S. Prairie, 4817 S. Prairie, and Rosemoor subdivisions.

Peoria Street is the 7th most expensive street in Chicago. It has condos, single-family homes, townhouses, multi-units, and land built from 1888 to 2020, ranging in price from $18,000 to $1,640,000. It is home to the Marquette Row, Westgate Center, Peoria Row Of River West, Peoria Street Lofts, Illume, Hale Lofts, and Sheldon Heights subdivisions.

Greenleaf Avenue is the 8th most expensive street in Chicago. It has condos, single-family homes, townhouses, co-ops, and multi-units ranging in price from $126,000 to $1,189,000. It is home to the 1334 W. Greenleaf, The Blond Condominiums, Grove at Greenleaf, 1510 W. Greenleaf, 1615 S. Greenleaf, 1354 W. Greenleaf, 1227 W. Greenleaf, 1340 W. Greenleaf, Bella Vita Condominiums, and Manresa Terrace subdivisions.

Indiana Avenue is the 9th most expensive street in Chicago. It has condos, townhouses, single-family homes, multi-units, and land built from 1903 to 2026, ranging in price from $36,000 to $1,285,000. It is home to the Lakeside Tower, Lakeside Lofts, Kensington Park, Stratford At South Commons, Prairie District Lofts, Michigan Place, Engravers Lofts, Lakeside on the Park, Bicycle Station Lofts, Kensington Park II, Penthouse Lofts, Bank Note Place, 4345 S. Indiana, 1616 S. Indiana, 4918 S. Indiana, East Side Lofts, Prairie Avenue Lofts, and 4357 S. Indiana subdivisions.

Bosworth Avenue is the 10th most expensive street in Chicago. It has condos, townhouses, single-family homes, multi-units, and land built from 1890 to 2025, ranging in price from $135,000 to $3,850,000. It is home to the Bosworth Place, 1307 N. Bosworth, Altgeld Commons, 3701 N. Bosworth, 1501 W. Bosworth, 1315 N. Bosworth, Southport Corridor, 3607 N. Bosworth, 2650 N. Bosworth Avenue, 1232 N. Bosworth, 1228 N. Bosworth, and 1238 N. Bosworth subdivisions.