665 Windward Way, Oregon, WI 53575
Property image
Property image
OFF MARKET

665 Windward Way
Oregon, WI 53575

  • 3 Beds
  • 2 Baths
  • 1,804 sqft

$386,300

Trulia Estimate
as of Aug 13, 2026
Est. Refi. Payment $2,521/mo*
Refinance Your Home

$386,300

Trulia Estimate
as of Aug 13, 2026
Est. Refi. Payment $2,521/mo*
Refinance Your Home
3 Beds
2 Baths
1,804 sqft

Home Value

Trulia Estimate
$386K
Since last month
Decreased$11K (-2.9%)
Since last year
Increased$2K (+0.4%)
Since last sale
Increased$196K (+103.3%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +86% in the last 10 years
MonthEstimated value
2026
August 2026$386K
July 2026$389K
June 2026$398K
May 2026$400K
April 2026$400K
March 2026$392K
February 2026$381K
January 2026$371K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
565 Oakwood Dr, Oregon, WI
0.24
Single-Family Home
$512,500
05/06/26
3
2
1,800
1129 Lincoln Rd, Oregon, WI
0.12
Single-Family Home
$466,000
04/30/26
4
3
2,381
290 Ash St, Oregon, WI
0.50
Single-Family Home
$385,000
09/08/25
3
2
1,820
411 Butternut Dr, Oregon, WI
0.38
Single-Family Home
$480,000
03/04/26
3
2
2,130
564 S Burr Oak Ave, Oregon, WI
0.18
Single-Family Home
$490,000
02/23/26
4
3
2,400
865 Miller Dr, Oregon, WI
0.43
Single-Family Home
$400,000
06/18/26
3
2
1,800
168 Hickory Ct, Oregon, WI
0.46
Single-Family Home
$420,000
12/08/25
3
2
2,300
434 S Burr Oak Ave, Oregon, WI
0.29
Single-Family Home
$499,900
06/10/26
4
3
2,438
151 Sterling Dr, Oregon, WI
0.46
Single-Family Home
$429,000
09/02/25
3
1.5
2,329
195 Ash St, Oregon, WI
0.67
Single-Family Home
$315,000
01/26/26
3
2
1,536

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
753 Leeward Ln, Oregon, WI 53575
0.06
$508,600
4
3.5
2,348
Off Market
1144 S Perry Pkwy, Oregon, WI 53575
0.03
$437,100
4
3
1,743
Off Market
742 Leeward Ln, Oregon, WI 53575
0.10
$449,900
3
2.5
1,420
Off Market
1129 Lincoln Rd, Oregon, WI 53575
0.12
$466,000
4
3
2,381
Recently Sold
625 Stonebriar Ln, Oregon, WI 53575
0.11
$446,900
3
2.5
1,588
Off Market
624-628 S Burr Oak Ave, Oregon, WI 53575
0.15
$606,900
6
3
3,584
Off Market
648-652 S Burr Oak Ave, Oregon, WI 53575
0.16
$571,600
6
4
3,040
Off Market
1133-1135 Union Rd, Oregon, WI 53575
0.18
$577,400
6
4
3,400
Off Market
1137-1139 Union Rd, Oregon, WI 53575
0.18
$558,900
6
4
2,864
Off Market
1141-1143 Union Rd, Oregon, WI 53575
0.18
$596,900
6
4
2,976
Off Market
1014 S Perry Pkwy, Oregon, WI 53575
0.18
$349,000
3
2.5
1,842
Recently Sold
1121-1123 Union Rd, Oregon, WI 53575
0.20
$525,000
6
3
2,808
Recently Sold

Local Information

  • Map ViewExplore the area around 665 Windward Way.
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2000
Living Area
1,804 sqft
Price/Sqft
$214
Parking
Garage

About this House

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!
665 Windward Way, Oregon, WI 53575 is a 3 bedroom, 2 bathroom, 1,804 sqft single-family home built in 2000. It last sold for $190,000 on Aug 1, 2014. It is currently off market. The Trulia Estimate is $386,300, with a rent estimate of $2,690/month.

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 and Tax history

DateEventPrice
Aug 1, 2014
Source: N/A
Sold
$190,000
Jun 21, 2014
Source: Agent Provided
Pending
$209,900
Jun 14, 2014
Source: Agent Provided
PriceChange
$209,900
Price decreased by 9%
Jun 6, 2014
Source: Agent Provided
Listed For Sale
$229,900

Market trends in Oregon

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$539K
Sale-to-List Price
—
Price per sq ft
—
Available listings
51
10MoM
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Around this home

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

Sourced by Trulia users. 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. "
    0
    Flag
  • 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 "
    0
    Flag
  • Lysagrant
    "15 minute drive from Madison. No public transportation. Easy access to rate 14. Not much traffic even at rush hour."
    0
    Flag
  • 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."
    0
    Flag
  • 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!"
    2
    Flag
  • Ken D.
    "Great schools, convenient to madison, stoughton and Fitchburg. Housing market is booming, low crime"
    0
    Flag
  • 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!"
    1
    Flag
  • miltydog
    "Wonderful schools and a strong sense of community"
    0
    Flag
  • Donna R. B.
    "Very private rural subdivision....may be a longer drive to madison but for the beautiful lot and privacy a huge bonus"
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  • 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!"
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  • 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

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Explore by feature - Pet Friendly

9 pet-friendly rentals in Oregon, WI

Explore by feature - Garage

6 rentals with a garage in Oregon, WI

Explore by feature - Air Conditioning

7 rentals with air conditioning in Oregon, WI

Explore by feature - Washer/dryer

6 rentals with a washer/dryer in Oregon, WI

Homes for sale near 665 Windward Way

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Off Market Homes Near 665 Windward Way

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Frequently asked questions about 665 Windward Way

  • What is 665 Windward Way estimated to be worth?
    Trulia's estimated value for 665 Windward Way in Oregon, WI is $386,300.
  • What is the price history for 665 Windward Way?
    665 Windward Way in Oregon, WI last sold for $190,000 in August 2014.
  • Is Oregon a buyer's or seller's market?
    Oregon is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Oregon?
    The median sale price in Oregon is $539K.
  • Does 665 Windward Way have air conditioning?
    Yes, 665 Windward Way in Oregon, WI has air conditioning.
  • Does 665 Windward Way have laundry facilities?
    Yes, 665 Windward Way in Oregon, WI has in-unit laundry.