276 Sterling Dr, Oregon, WI 53575
Property image
Property image
OFF MARKET

276 Sterling Dr
Oregon, WI 53575

  • 3 Beds
  • 3 Baths
  • 2,322 sqft (on 0.32 acres)

$543,000

Trulia Estimate
as of Jul 24, 2026
Est. Refi. Payment $3,525/mo*
Refinance Your Home

$543,000

Trulia Estimate
as of Jul 24, 2026
Est. Refi. Payment $3,525/mo*
Refinance Your Home
3 Beds
3 Baths
2,322 sqft
(on 0.32 acres)

Local Information

  • Map ViewExplore the area around 276 Sterling Dr.
  • Schools2 Preschool Schools3 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1965
Lot Size
0.32 acres
Living Area
2,322 sqft
Price/Sqft
$234

About this House

This 3 bed, 2.5 bath house has room to spare & room to grow & with a high level of depth & interest in its design. Main level holds kitchen, living rm & large family room. Expansive windows abound to show off the large fenced backyard w/above ground pool. Upper level contains all 3 bedrooms & 2 baths. Ceiling fans in all bedrooms for great air circulation. Lower level has half bath. A short drive or bike ride to downtown Oregon, 14 min to beltline.
276 Sterling Dr, Oregon, WI 53575 is a 3 bedroom, 3 bathroom, 2,322 sqft single-family home built in 1965. It last sold for $260,000 on Aug 20, 2014. It is currently off market. The Trulia Estimate is $543,000, with a rent estimate of $2,827/month.

Home Details for 276 Sterling Dr

Interior Features

Heating & Cooling
Heating: OtherAir ConditioningCooling System: Central, OtherHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Types of Rooms: Dining Room, Family Room, Laundry Room
Appliances & Utilities
Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher

Exterior Features

Exterior Home Features
Roof: OtherExterior: Stone, Vinyl, BrickLawnPatio
Pool
Pool
Parking & Garage
Parking Spaces: 2

Property Information

Year Built
Year Built: 1965
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 0.32 acres

Price History for 276 Sterling Dr

DatePriceEventSource
08/20/2014$260,000Sold
SCWMLS #1719480
06/19/2014$269,900Listed For SaleAgent Provided
06/15/2007$280,000Sold
N/A

Market trends in Oregon

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
61
2MoM
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Property Tax and Assessment

Year2024
Tax$8,565
Assessment$556,300
Home facts updated by county records

Comparable Sales for 276 Sterling Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
269 Kierstead Ln, Oregon, WI
0.12
Single-Family Home
$375,000
01/14/26
3
2
2,167
151 Sterling Dr, Oregon, WI
0.16
Single-Family Home
$429,000
09/02/25
3
1.5
2,329
261 Sterling Dr, Oregon, WI
0.05
Single-Family Home
$437,600
07/29/25
3
2
1,624
182 Ames St, Oregon, WI
0.18
Single-Family Home
$430,000
12/05/25
3
2.5
1,857
192 State St, Oregon, WI
0.18
Single-Family Home
$395,000
12/01/25
3
3
1,918
700 S Perry Pkwy, Oregon, WI
0.27
Single-Family Home
$365,000
10/29/25
3
2
2,184
190 S Oak St, Oregon, WI
0.28
Single-Family Home
$438,500
01/30/26
4
2.5
2,184
800 Miller Dr, Oregon, WI
0.38
Single-Family Home
$465,000
05/18/26
3
2.5
1,972
865 Miller Dr, Oregon, WI
0.36
Single-Family Home
$400,000
06/18/26
3
2
1,800
127 Thomson Ln, Oregon, WI
0.33
Single-Family Home
$440,000
02/27/26
3
2
1,749

Nearby homes

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Assigned Schools

These are the assigned schools for 276 Sterling Dr.
View nearby schools on GreatSchools
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

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"
    0
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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."
    0
    Flag

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6 pet-friendly rentals in Oregon, WI

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Homes for sale near 276 Sterling Dr

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Off Market Homes Near 276 Sterling Dr

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