187 Sterling Dr, Oregon, WI 53575
Property image
Property image
FOR SALE
0.34 ACRES

$414,900

Original price: $419,900
  • 3 Beds
  • 2 Baths
  • 1,613 sqft (on 0.34 acres)

187 Sterling Dr, Oregon, WI 53575

Get Pre-Qualified
We estimate this home will sell faster than 90% nearby.

Home Highlights

Single-Family Home
Built in 1962
0.34 acre lot
$257/sqft
3 Car Garage

Local Information

  • Map ViewExplore the area around 187 Sterling Dr.
  • Schools2 Preschool Schools3 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

What's unique:Spa-like bathroomStunning hardwood floorsBeautiful outdoor spacesNew maintenance-free deckRemodeled kitchenGenerous lot
Beautiful ranch home offering the perfect blend of comfort, convenience, and outdoor enjoyment. Stunning hardwood floors welcome you inside, while the remodeled kitchen is ready for everyday living and entertaining alike. Unwind in the spa-like bathroom, designed to feel like your own private retreat. Outside, enjoy a generous lot featuring cherry trees, apple trees, plum tree, raspberry bush, and plenty of room to garden, play, or relax. The new maintenance-free deck is perfect for summer gatherings and quiet mornings alike. A dedicated theater room, complete with all equipment included, provides the ultimate movie-night experience. The oversized 3-car garage offers ample storage and workspace. Conveniently located near shopping, restaurants, parks, and everyday amenities, this home combines thoughtful updates, beautiful outdoor spaces, and exceptional value. Roof '20/'21, Water Heater '21, Kitchen Appliances '22, Furnace & A/C '23!
Last check for updates: about 8 hours ago
Listing courtesy of Jason Fowler
Century 21 Affiliated
Jeff Kramer
Century 21 Affiliated
Source: SCWMLS, MLS#2030702
We estimate this home will sell faster than 90% nearby.

Home Details for 187 Sterling Dr

Active Status

MLS Status: Active

Interior Features

Interior Details
Basement: Full,Partially Finished,Radon Mitigation SystemNumber of Rooms: 6Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Family Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2Number of Bathrooms (main level): 1
Dimensions and Layout
Living Area: 1613 Square Feet
Appliances & Utilities
Utilities: Cable AvailableAppliances: Washer, Dryer, Water Softener IncludedDryerWasher
Heating & Cooling
Heating: Forced AirHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
No Fireplace
Levels, Entrance, & Accessibility
Stories: 1Levels: One

Exterior Features

Exterior Home Features
Patio / Porch: DeckFoundation: Poured concrete foundatn
Parking & Garage
Number of Garage Spaces: 3Number of Covered Spaces: 3No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 3Parking: Additional Parking,Attached,Tandem,Garage Door Opener
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 1232 Square Feet

Property Information

Year Built
Year Built: 1962
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Ranch
Building
Construction Materials: Aluminum Siding
Property Information
Not Included in Sale: Seller's personal propertyIncluded in Sale: Washer, Dryer, Refrigerator, Dishwasher, Range/Oven, Water Softener, Projector, Screen, Theatre Sound System, All Theatre Equipment, Smart Doorbell, All Window Coverings.Parcel Number: 050912302299

Price & Status

Price
List Price: $414,900Price Per Sqft: $257

Location

Direction & Address
City: Oregon
School Information
Elementary School: Netherwood KnollElementary School District: OregonJr High / Middle School: OregonJr High / Middle School District: OregonHigh School: OregonHigh School District: Oregon

Agent Information

Listing Agent
Listing ID: 2030702

Building

Building Area
Building Area: 1613 Square Feet

Lot Information

Lot Area: 0.34 acres

Miscellaneous

BasementMls Number: 2030702Attribution Contact: Pref: 608-438-5056Above Grade Unfinished Area: 1232

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. "
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  • 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 "
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  • Lysagrant
    "15 minute drive from Madison. No public transportation. Easy access to rate 14. Not much traffic even at rush hour."
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  • 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."
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  • 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"
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    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"
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    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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Market trends in Oregon

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$535K
$4.17KMoM
Sale-to-List Price
—
Price per sq ft
$223
$18MoM
Available listings
43
8MoM

Home Value

Trulia Estimate
$410K
Since last month
Decreased$11K (-2.5%)
Since last year
Increased$7K (+1.8%)
Since last sale
Increased$10K (+2.4%)
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 +98% in the last 10 years
MonthEstimated value
2026
September 2026$410K
August 2026$420K
July 2026$411K
June 2026$414K
May 2026$417K
April 2026$417K
March 2026$415K
February 2026$414K
January 2026$408K
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
269 Kierstead Ln, Oregon, WI
0.16
Single-Family Home
$375,000
01/14/26
3
2
2,167
865 Miller Dr, Oregon, WI
0.39
Single-Family Home
$400,000
06/18/26
3
2
1,800
192 State St, Oregon, WI
0.13
Single-Family Home
$395,000
12/01/25
3
3
1,918
700 S Perry Pkwy, Oregon, WI
0.38
Single-Family Home
$365,000
10/29/25
3
2
2,184
411 Butternut Dr, Oregon, WI
0.35
Single-Family Home
$480,000
03/04/26
3
2
2,130
182 Ames St, Oregon, WI
0.28
Single-Family Home
$430,000
12/05/25
3
2.5
1,857
127 Thomson Ln, Oregon, WI
0.45
Single-Family Home
$440,000
02/27/26
3
2
1,749
260 Ash St, Oregon, WI
0.52
Single-Family Home
$365,000
07/30/26
3
1.5
1,250
489 Cherry Wood Dr, Oregon, WI
0.30
Single-Family Home
$453,000
08/31/26
3
2.5
2,137

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
151 Sterling Dr, Oregon, WI 53575
0.03
$443,200
3
1.5
2,329
Off Market
202 Sterling Dr, Oregon, WI 53575
0.04
$401,900
3
2
1,736
Off Market
161 Kierstead Ln, Oregon, WI 53575
0.08
$479,800
4
2
2,469
Off Market
235 Sterling Dr, Oregon, WI 53575
0.07
$385,800
3
1
1,232
Off Market
552 S Main St, Oregon, WI 53575
0.10
$311,700
3
1
1,442
Off Market
148 State St, Oregon, WI 53575
0.13
$350,400
3
2
1,960
Off Market
192 State St, Oregon, WI 53575
0.13
$395,000
3
3
1,918
Recently Sold
159 State St, Oregon, WI 53575
0.16
$424,700
3
2
1,951
Off Market
260 Kierstead Ln, Oregon, WI 53575
0.13
$393,200
3
2
1,346
Off Market
270 Kierstead Ln, Oregon, WI 53575
0.15
$389,600
3
2
1,636
Off Market
269 Kierstead Ln, Oregon, WI 53575
0.16
$375,000
3
2
2,167
Recently Sold

Price and Tax history

DateEventPrice
Sep 15, 2026
Source: SCWMLS #2030702
PriceChange
$414,900
Price decreased by 1%
Aug 17, 2026
Source: SCWMLS #2030702
Listed For Sale
$419,900
Apr 22, 2025
Source: N/A
Sold
$400,000
Mar 2, 2025
Source: WIREX MLS #1992906
Contingent
$400,000
Feb 26, 2025
Source: WIREX MLS #1992906
Listed For Sale
$400,000

LGBTQ Local Legal Protections

Jason Fowler, Century 21 Affiliated

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Frequently asked questions about 187 Sterling Dr

  • What is the estimated monthly payment for 187 Sterling Dr?
    Based on a $414,900 list price with 20% down at today's rates, the estimated monthly payment for 187 Sterling Dr in Oregon, WI is approximately $2,842 (about $2,255 principal & interest, $512 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • How does the list price for 187 Sterling Dr compare to homes in Oregon?
    187 Sterling Dr in Oregon, WI is listed at $414,900, about 22% below the $535K median sale price in Oregon.
  • What do residents say about Oregon?
    Residents describe Oregon, WI as easy to park in, dog-friendly, and pedestrian-friendly. See homes for sale in Oregon, WI.
  • What are the closest schools to 187 Sterling Dr?
    The closest schools to 187 Sterling Dr in Oregon, WI are Netherwood Knoll Elementary School (Pre-K, rated 7/10), Oregon High School (rated 10/10), Oregon Middle School (rated 5/10).
  • Does 187 Sterling Dr have air conditioning?
    Yes, 187 Sterling Dr in Oregon, WI has air conditioning.
  • Does 187 Sterling Dr have laundry facilities?
    Yes, 187 Sterling Dr in Oregon, WI has in-unit laundry.
187 Sterling Dr, Oregon, WI 53575 is a 3 bedroom, 2 bathroom, 1,613 sqft single-family home built in 1962. This property is currently available for sale and was listed by SCWMLS. The MLS # for this home is MLS# 2030702.