Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$449,900 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 3 Full Baths
  • 1,612 Sq. Ft.
  • 2 Car Garage
  • Updated 4 days ago
See This Home
Save This Home
See This Home
Save This Home
Comfortable bi-level home in the sought-after Castle Crest neighborhood! This spacious 3 bedrooms upstairs with 2 full baths. The main level features a large living room filled with natural light, plus an eat-in kitchen with patio door leading to a newer deck. Enjoy a generous backyard complete with a fire pit, perfect for summer nights. Additional highlights include newer Andersen windows, newer roof and siding, stainless steel appliances, beautiful granite countertops, and a cozy gas fireplace with an additional half bath in the lower level, ideal for movie nights or game days. Walk to Waunakee schools and a quick drive to restaurants, nightlife, and parks. A wonderful opportunity in a prime location you won't want to miss!

Full Property Details for 105 Winston Way

General

  • Price: $449,900
  • Taxes: $5,652 (2024)
  • Status: Active
  • Type: Single Family
  • Source: MetroMLS_Milwaukee_Wirex
  • MLS ID: 1947208
  • Updated: 1/13/2026
  • Added to Site: 4 day(s) ago

Interior

  • Interior Features: Cable TV Available, Gas Fireplace, Simulated Wood Floors
  • Appliances: Dryer, Microwave, Other, Oven, Range, Refrigerator, Washer, Water Softener Owned

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 3
  • Bathroom: At least one Bathtub, Off Master Bedroom

Bedrooms

  • Total Bedrooms: 3
  • Bedroom 2: 12 x 10, Main Level
  • Bedroom 3: 10 x 10, Main Level

Other Rooms

  • Living Room: 18 x 13, Main Level
  • Kitchen: 18 x 11, Main Level
  • Laundry: Lower Level

Exterior

  • Exterior Features: Deck

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Garage Description: Electric Door Opener

Location

  • County: Dane
  • Subdivision: Castle Crest
  • Driving Directions: Head north Co Hwy Q/Co Rd Q toward Water Wheel Dr, Turn right onto Peaceful Valley Parkway, Turn left onto Simon Crestway, Turn right onto Winston Way

School Information

  • School District: Waunakee Community
  • Middle School: Waunakee
  • High School: Waunakee

Heating & Cooling

  • Heating/Cooling: Natural Gas, Central Air Conditioning, Forced Air

Utilities

  • Water/Sewer: Municipal Sewer, Municipal Water

Structural Information

  • Architectural Style: 1.5 Story, Bi-Level, Exposed Basement, Multi-Level, Tri-Level, Other
  • Description/Design: Subdivision
  • Exterior Const.: Brick, Wood
  • Basement Desc.: Poured Concrete, Shower
  • Square Feet: 1,612
  • Year Built: 1979

Lot Features

  • Lot Size (Acres): 0.25
  • Zoning: Residential

Financial Considerations

  • Tax Amount: $5,652
  • Tax Year: 2024

Listed by Keller Williams Realty-Milwaukee Southwest

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Listing agent

— 105 Winston Way —

  • Keller Williams Realty-Milwaukee Southwest

262-599-8980

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Get a Great Insurance Rate

Find the right home insurance for your new home!

with our affiliated in-house agency

Request a Quote

Save up to an additional 20% by bundling your home and auto together!

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Find the right home insurance for your new home!

with our affiliated in-house agency

Request a Quote

Save up to an additional 20% by bundling your home and auto together!

Schools serving 105 Winston Way

School District:Waunakee Community School District
NameGradesDistance
Waunakee Heritage Elementary School
501 South Street, Waunakee, WI 53597
K-40.6 mi
Waunakee Intermediate School
6273 Woodland Drive, Waunakee, WI 53597
5-61 mi
Waunakee Middle School
1001 South Street, Waunakee, WI 53597
7-80.2 mi
Waunakee High School
301 Community Drive, Waunakee, WI 53597
9-120.2 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 105 Winston Way Get Price Alerts and Save Property

Date
Details
Price
Change
Source
1/13/2026
Listed
$449,900
12.76%
MLS
8/13/2022
Sold
$399,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 105 Winston Way

Year
Property Taxes
Change
Tax Assessment
Change
2024
$5,653
4%
$352,000
—
2022
$5,447
2%
$352,000
27%
2022
$5,317
1%
$276,500
—
2021
$5,277
3%
$276,500
—
2020
$5,143
1%
$276,500
—
2019
$5,114
9%
$276,500
23%
2018
$4,680
—
$224,000
—
2017
$4,665
4%
$224,000
2%
2016
$4,487
6%
$219,000
4%
2015
$4,239
9%
$210,500
6%
2014
$3,878
-3%
$198,000
—
2013
$3,980
—
$198,000
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 105 Winston Way

$
Down Payment
%
$
%

$
$

*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Keller Williams Realty-Milwaukee Southwest

105 Winston Way, Waunakee, WI 53597 (MLS# 1947208) is a Single Family property with 3 bedrooms and 3 full bathrooms. 105 Winston Way is currently listed for $449,900 and was received on January 13, 2026. Want to learn more about 105 Winston Way? Do you have questions about finding other Single Family real estate for sale in Waunakee? You can browse all Waunakee real estate or contact a Coldwell Banker agent to request more information.

Tour this property