Show 6/11. Darling and well maintained Cherokee Charmer. You’ll love the brick paver path leading up to the stonework facade. The interior is made larger by an addition to the rear as well as "lives large" due to the super-efficient and spacious Dutch Colonial design and gambrel roof lines. Built in 1937, this home has been immaculately maintained and updated while still showcasing the quality and intentions of yesteryear. The lush and beautiful yard and grounds connect the home with the adjacent boulevard and give a feeling of living in the trees. This urban but forested oasis is a real gem.
Property Details
Price:
$749,900
MLS #:
SCW2024443
Status:
Pending
Beds:
3
Baths:
1.5
Type:
Single Family
Listed Date:
Jun 10, 2026
Finished Sq Ft:
1,986
Lot Size:
8,276 sqft / 0.19 acres (approx)
Year Built:
1937
See this Listing
Schools
School District:
Madison
Elementary School:
Thoreau
Middle School:
Cherokee
High School:
West
Interior
Appliances
Range/Oven, Refrigerator, Dishwasher, Microwave, Window A/C, Washer, Dryer
Bath Descriptions
No Master Bedroom Bath
Bedroom2Level
Upper
Bedroom3Level
Upper
Full Baths
1
Half Baths
1
Interior Features
Great Room, Walk-up Attic, Water Softener, High Speed Internet
Kitchen Level
Main
Living Room Level
Main
Exterior
Basement
Full, Partially Finished, Poured Concrete
Exterior
Wood, Brick, Stone
Exterior Features
Fenced Yard
Financial
Heat Fuel
Natural Gas
Heating Cooling
Radiant
Taxes
$12,504
Map
Community
- Address4158 Cherokee Drive Madison WI
- CityMadison
- CountyDANE
- Zip Code53711
Subdivisions in Madison
- Apple Ridge
- Appplewood Hill
- Arbor Hills
- Arbordale
- Baxter Highlands
- Blackhawk
- Bowens Addition
- Brentwood Village
- Carton Crest
- Chapel Hill
- Chapel Valley
- Charing Cross Meadows
- Clarendon Hills
- Cloverleaf Acres
- Clyde A Gallagher
- CLYDE A GALLAGHER PARK SUBD FIRST ADD, L
- Clyde A. Gallagher
- Clyde A. Gallagher\’s Sherman Ave
- Clyde A. Gallagher\’s Subdivision
- Crawford Heights Third Addition
- Crestview
- Dudgeon-Monroe
- E L Gallagher
- Eastmorland
- Eastridge Trail
- Eken Park
- Elvehjem
- Fahey Fields
- Fair Oaks
- Faircrest
- Fairview Additions
- Farwells Replat
- Fieldstone
- Findlay Park
- Fuller\’s Woods
- Glacier Crossing
- Glacier Heights
- GLEN OAK HILLS
- Glen Oaks Hills
- Glendale
- Golf Green
- Grandview Commons
- Grandview Commons North
- GRANDVIEW COMMONS NORTHEAST
- Greenbush
- Greentree
- Griffiths Beach
- Hauser Estates
- HAVEN AT VILLAGE AT AUTUMN LAKE
- HAVEN VILLAGE AT AUTUMN LAKE
- Hawk\’s Creek
- Hawks Creek
- Hawks Ridge
- Heather Glen Addition to the Crossing
- Heritage Heights
- Hickory Ridge
- HIGH POINT ESTATES
- Highland Village
- Highland Village 2nd Addn
- Highlands
- Hill Farms
- Hillington
- HILLSIDE ADDITION TO MEADOWOOD
- Hillview Heights Addition
- Honeysuckle Acres
- Ice Age Ridge
- Indian Springs
- Jannah Village
- John W Tilton
- Junction Ridge 1st Addn
- Knox Add to Summit Ridge
- Lake Edge Park
- Lansing Place
- Liberty Place
- Lincoln Hills
- LOT 3 CSM
- Manor Green Add to Meadowood
- Maple Bluff
- Marlborough Heights
- Marquette
- McKenna Park
- Meadowood
- MEEK-BROWNE
- Mendota Hills
- Mid Town Commons
- Midland Meadows
- Midpoint Meadows
- Midvale Heights
- Morningside Heights
- Nakoma
- Nakoma Park
- Nakoma/Crawford Heights
- Nesbitt Valley
- Newberry Heights
- Nob Hill Park
- North Lake Mendota
- Northland Manor
- Oakbridge
- Olbrich Park
- Old Sauk Village
- Orchard Ridge
- Painted Post Estates
- Parkwood Hill Estates
- Parkwood Hills
- Pinckney Row Plat
- Post Road Addition to Arbor
- Quaker Heights
- Quaker Heights 1st Add
- Rambling Acres
- Raywood Heights
- Reston Heights
- Richmond Hill
- Ridgewood
- Rolling Meadows
- Sandburg Heights
- Sandstone Ridge
- Sandstone Ridge Daniel Addn
- Sanford Holiday Bluff
- Sauk Creek
- Schenk Park
- Sherman Village
- Shorewood Hills
- Ski Lane Properties
- Spring Harbor
- Stone Crest Estates
- Stonecrest Estates
- Stonefield Ridge
- Stony Ridge
- Sun Gardens
- Sunridge
- Sunrise Meadows
- Sunset Hills
- Sunset Hills / Highland Park
- Sunset Village
- Swanton Acres
- Tamarack Trails
- Tenney-Lapham
- Terravessa
- The Crossing
- The Highlands
- The Meadowlands
- The Trillium
- The Turn
- The Turn at Cherokee
- Third Add to Downs of West Meadowood
- Timber Lane
- Twin Oaks
- University Heights
- University Hill Farms
- Valhalla Valley/High Point
- Valley Ridge
- Vang Homesites
- Vilas
- VILLAGE AT AUTUMN LAKE
- Village of Autumn Lake
- Washington Park
- Waubesa Beach
- West Lawn
- West Meadowood Hills
- Westchest Park, Outlot
- WestHaven Trails
- Westmorland
- Westport Meadows
- Westvale
- Wexford Village
- Wheeler Heights 2nd Add.
- Whitetail Ridge
- Wingra Park
- WOODLAND HILLS
- WOODLAWN
- Woodlawn Add
- Woodward Grove
Market Summary
Current real estate data for Single Family in Madison as of Jun 19, 2026
428
Single Family Listed
38
Avg DOM
295
Avg $ / SqFt
$578,893
Avg List Price
Property Summary
- 4158 Cherokee Drive Madison WI is a Single Family for sale in Madison, WI, 53711. It is listed for $749,900 and features 3 beds, 2 baths, and has approximately 1,986 square feet of living space, and was originally constructed in 1937. The current price per square foot is $378. The average price per square foot for Single Family listings in Madison is $295. The average listing price for Single Family in Madison is $578,893. To schedule a showing of MLS#scw2024443 at 4158 Cherokee Drive in Madison, WI, contact your Keith McNeely Real Estate agent at 608.370.4020.
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