995 Oak Street — Winnetka, IL 60093
Active Under Contract
Winnetka, IL 60093

995 Oak Street

$1,699,000
4 beds · 5 baths · 3,639 sqft
Listed at $1,699,000 14 days on market $32,794/yr taxes
01About this home

Easy, in-town living in this wonderful home! This spacious home is conveniently located in the ideal 'walk to everything' location in the heart of Winnetka - close to absolutely everything. Built in 1995 with all the amenities one needs: classic center entry layout, large welcoming foyer, bright interior with an abundance of natural light, large scaled rooms, eat-in kitchen adjacent to family room which has sliding doors out to the southern patio and fully fenced yard. Primary suite with ensuite bath (with soaking tub, double vanities & separate shower), walk-in closet & skylight. Three additional bedrooms and 2 full baths round out the 2nd floor. Finished lower level with heated floors and a rec room and play area plus full bath. Plenty of storage throughout the home including the large storage room in the basement. All in move-in condition! Special amenities include first floor laundry/mudroom, 2 car attached / heated garage. This well designed and light-filled house is located on a large corner lot (50 x 187) and is bathed in sunlight all day long. A short walk to the center of downtown Winnetka for shopping, restaurants, parks and train and a short walk to K-8 schools, golf, tennis, paddle facilities and ice arena. All the space you need in all the right places!

02Inside the home
03By the numbers
$1,699,000
List price
3,639
Square feet
4
Bedrooms
4 full / 1 half
Bathrooms
1994
Year built
0.21 ac
Lot size
2
Garage spaces
$32,794
Annual taxes
Detached Single
Style
14
Days on market
04Features
Heating
Natural GasForced AirRadiantRadiant Floor
Cooling
Central Air
Appliances
RangeDishwasherRefrigeratorWasherDryerDisposalCooktop
Parking
ConcreteGarageGarage OwnedAttached
Construction
BrickFrame
Equipment
Sump PumpWater Heater-Gas
Sewer
Public Sewer
05Neighborhood
This home EElementary schoolMMiddle school
E Elementary school
Crow Island Elementary School
Winnetka, IL
📍0.4 mi🚗1 min🚶10 min
M Middle school
Carleton W Washburne School
Winnetka, IL
📍0.4 mi🚗1 min🚶11 min
H High school
New Trier Twp H.S. Northfield/Wi
Winnetka, IL
  • Little Lan's 0.3 mi
  • Trifecta Grill 0.3 mi
  • Fred's Garage 0.4 mi
  • Green Bay Cafe 0.4 mi
  • McDonald's 0.7 mi
  • Spirit Elephant 0.8 mi
  • Lakeside Foods 0.4 mi
  • The Grand Food Center 0.4 mi
  • BP Shop 0.8 mi
  • 7-Eleven 1.2 mi
  • Dwyer Park 0.3 mi
  • West Elm Street Park 0.3 mi
  • Station Park 0.4 mi
  • Library Park 0.5 mi
  • Arborvitae Park 0.5 mi
  • Duke Childs Field 0.6 mi
  • Peet's Coffee 0.3 mi
  • Starbucks 0.3 mi
  • Hometown Coffee & Juice 0.5 mi
  • Dunkin' 1.1 mi
  • Tala Coffee Roasters 1.2 mi
  • Starbucks 1.5 mi
POI data via Mapbox · OpenStreetMap contributors
06History

Every event we have for this address, straight from the MLS.

Apr 13, 2026
Listed for saleThis listing
Compass
$1,699,000
Sourced from MRED. Older events appear here as our history backfill completes.
07Ask Dwello

Real answers about this home — pricing, schools, what to ask, anything.

08See it for yourself

Stand in the kitchen.
See the light at 4pm.

Photos can only do so much. Pick a time — we'll meet you at the door.

Connect with Ewelina, Sonia, or Anna — real people on our team, no call centers.
09Similar homes
Listed by Compass · Joanne Hudson · 847-971-5024
MLS data provided through MLS GRID · MRED MLS · MLS# MRD12613148
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