665 Windward Way, Oregon, WI 53575
OFF MARKET

665 Windward Way
Oregon, WI 53575

  • 3 Beds
  • 2 Baths
  • 1,804 sqft

$402,100

Trulia Estimate
as of May 15, 2026
Est. Refi. Payment $2,581/mo*

$402,100

Trulia Estimate
as of May 15, 2026
Est. Refi. Payment $2,581/mo*
3 Beds
2 Baths
1,804 sqft

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Let the kids walk to school! Spacious 3 bedroom, 2 bath ranch style open floor plan ready for you to call home. Nice open floor plan featuring vaulted ceilings, fresh carpet, master bedroom with private bath. Patio doors that lead to the spacious deck and backyard. Awesome finished lower level with built in bar & additional storage. Wonderful location across from the park and a quick walk to the school. Quick closing possible, seller is ready to move!
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 665 Windward Way

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1
Interior Details
Types of Rooms: Dining Room, Family Room
Appliances & Utilities
DishwasherDisposalDryerMicrowaveRefrigeratorWasher

Exterior Features

Exterior Home Features
Roof: OtherExterior: Vinyl
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 2000
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Community

Units in Building: 1

Lot Information

Lot Area: 9583 sqft

Price History for 665 Windward Way

DatePriceEventSource
08/01/2014$190,000Sold
N/A
06/21/2014$209,900PendingAgent Provided
06/14/2014$209,900PriceChange
Agent Provided
06/06/2014$229,900Listed For SaleAgent Provided
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Property Tax and Assessment

Year2024
Tax$4,603
Assessment$309,400
Home facts updated by county records

Comparable Sales for 665 Windward Way

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.10
Single-Family Home
$440,000
07/10/25
3
2.5
1,420
0.24
Single-Family Home
$512,500
04/30/26
3
2
1,800
0.12
Single-Family Home
$466,000
04/29/26
4
3
2,381
0.38
Single-Family Home
$480,000
02/27/26
3
2
2,130
0.18
Single-Family Home
$490,000
02/23/26
4
3
2,400
0.46
Single-Family Home
$420,000
12/02/25
3
2
2,300
0.60
Single-Family Home
$415,000
06/20/25
3
2
1,951
0.56
Single-Family Home
$420,000
07/24/25
4
2
1,682
0.46
Single-Family Home
$429,000
08/28/25
3
1.5
2,329
0.67
Single-Family Home
$315,000
01/23/26
3
2
1,536

Assigned Schools

These are the assigned schools for 665 Windward Way.
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Oregon

At least 64 Trulia users voted on each feature.
  • 94 % Say parking is easy

  • 94 % Say it's dog friendly

  • 92 % Say there are sidewalks

  • 87 % Say kids play outside

  • 86 % Say people would walk alone at night

  • 85 % Say yards are well-kept

  • 84 % Say car is needed

  • 80 % Say streets are well-lit

  • 80 % Say there's holiday spirit

  • 77 % Say it's quiet

  • 68 % Say it's walkable to restaurants

  • 68 % Say they plan to stay for at least 5 years

  • 68 % Say neighbors are friendly

  • 58 % Say there's wildlife

  • 48 % Say it's walkable to grocery stores

  • 43 % Say there are community events

Learn more about our methodology.
  • Tanya Hoppe
    "Friendly and family orientated little Town with great school district. Our neighbors are great and watch out for each other. "
  • Khockett58
    "Village Oregon Great place to live. Great schools & sport Great food places to eat. Doctor clinics Gad stations Banks. Small town but close to drive in to Madison or Stoughton And other cities "
  • Lysagrant
    "15 minute drive from Madison. No public transportation. Easy access to rate 14. Not much traffic even at rush hour."
  • Tjrbackstroker
    "A quick drive up to Madison. The area is very drivable with not too much traffic. It is very easy to get on the highway."
  • Kelly J. P.
    "Love it here! Best move to call this home for our family to grow. Super nice community. We love our neighbors and enjoy to small town feel that Oregon has to offer & also super close to Madison for fun nights out!"
  • Ken D.
    "Great schools, convenient to madison, stoughton and Fitchburg. Housing market is booming, low crime"
  • Rachel
    "To always keep an eye on your kids no matter how safe a neighborhood is deemed to be. Oregon is a great place to live!"
  • miltydog
    "Wonderful schools and a strong sense of community"
  • Donna R. B.
    "Very private rural subdivision....may be a longer drive to madison but for the beautiful lot and privacy a huge bonus"
  • Stevie K.
    "If you like your privacy, multi level living, looking out the back you feel as if you are in the woods! Lots of updates and well cared for. Great neighbors, I used to be one but moved out West, so I have personally been inside and it's great! It is located on a private circle with little traffic! It's definitely a must see!"
  • Stefan
    "This area of Oregon is excellent. The schools are the best. The neighborhoods around Lincoln Road, County A and Hillcrest are nice, but, drivers have no regard for safety at all. Stay off these roads if you bike or run. Farm families are very nice, too. You will love bringing up children in this area. Oregon is the best community in the Madison area for kids and your families to live."

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Apartments for Rent

Homes for sale near 665 Windward Way

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Homes for rent near 665 Windward Way

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Off Market Homes Near 665 Windward Way

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Explore by feature

665 Windward Way, Oregon, WI 53575 is a 3 bedroom, 2 bathroom, 1,804 sqft single-family home built in 2000. This property is not currently available for sale. 665 Windward Way was last sold on Aug 1, 2014 for $190,000. The current Trulia Estimate for 665 Windward Way is $402,100.