244 Jefferson St, Oregon, WI 53575
Property image
Property image
OFF MARKET

$322,500

Trulia Estimate
as of Sep 21, 2026
  • 4 Beds
  • 2 Baths
  • 2,000 sqft

244 Jefferson St, Oregon, WI 53575

Home Highlights

Single-Family Home
2,000 sqft
$161/sqft

Local Information

  • Map ViewExplore the area around 244 Jefferson St.
  • Schools2 Preschool Schools3 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Beautifully renovated historical home located two blocks from downtown Oregon. Potentially five bedrooms. Large playground in backyard. Asphalt parking. Newer electrical plumbing and kitchen. Two large porches and a mudroom. Lots of spaces that can be used as needed. Carpeted upstairs beautiful hardwood floors downstairs. Must see!

Owner will mow the grass and take care of gardens. Renter will pay for utilities (electricity, gas, water, sewage, etc). Renter will snow plow or shovel snow in property and sidewalks. Renter is responsible for obtaining access to the internet. No in-door animals. There is no smoking in the property.

We require a one month deposit equal to one month rent at $2,900 and first month rent prior to move in. The lease is a one year lease. Additional year is negotiable but not mandatory. Rent must be paid no later than five days prior to the next month of rent. Renter will pay 2% late fee for every week delinquent.

Prior to move in, renter and owners will take pictures of the interior and exterior of the house to agree to the current state of the property. Renter will ensure that the current state of the house will be maintained throughout the term of the lease. Inability to maintain the condition of the property will result on forfeit of deposit.

Renter is responsible for routine maintenance of the property. Renter will obtain and maintain renter's insurance during the term of the lease.
244 Jefferson St, Oregon, WI 53575 is a 4 bedroom, 2 bathroom, 2,000 sqft single-family home. It last sold for $57,500 on Aug 10, 2010 (1,883% above the $2,900 asking price). More recently, it was listed as a rental in August 2025 with an asking price of $2,900 per month. That rental listing was removed on September 30, 2025. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $322,500, with a rent estimate of $2,672/month.

Home Details for 244 Jefferson St

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: Central AirHeating Fuel: Forced Air
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Levels, Entrance, & Accessibility
Floors: Carpet, Hardwood

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 1 Year

Exterior Features

Parking & Garage
Parking: Off Street Parking, On Site

Community

Other
Playground

Additional Information

Playground

Comparable Sales for 244 Jefferson St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
285 Walnut St, Oregon, WI
0.05
Single-Family Home
$440,000
09/01/26
4
1.5
1,625 sqft
235 Bethel Ct, Oregon, WI
0.12
Single-Family Home
$280,000
06/16/26
3
2
1,590 sqft
195 Ash St, Oregon, WI
0.29
Single-Family Home
$315,000
01/26/26
3
2
1,536 sqft
163 Walnut St #3, Oregon, WI
0.26
Single-Family Home
$242,900
06/03/26
3
1.5
1,090 sqft
135 Johnson St, Oregon, WI
0.29
Single-Family Home
$373,000
08/17/26
3
2
1,514 sqft
277 N Main St, Oregon, WI
0.25
Single-Family Home
$329,300
04/30/26
3
2
1,555 sqft
168 Hickory Ct, Oregon, WI
0.36
Single-Family Home
$420,000
12/08/25
3
2
2,300 sqft
411 Butternut Dr, Oregon, WI
0.38
Single-Family Home
$480,000
03/04/26
3
2
2,130 sqft
609 N Woods Edge Dr, Oregon, WI
0.37
Single-Family Home
$500,000
06/11/26
3
2
2,230 sqft
260 Ash St, Oregon, WI
0.31
Single-Family Home
$365,000
07/30/26
3
1.5
1,250 sqft

Nearby homes

Get a sense of prices in the area by checking nearby homes.
Skip to last item
Skip to first item

Rental Market Trends in Oregon

Last updated Sep 2026
Trulia Rent Estimate$2,672/mo
Average rent
$1.53K
$5MoM
Available listings
11
View rental market trends in Oregon, WI

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"
    0
    Flag
  • 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!"
    0
    Flag
  • 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

LGBTQ Local Legal Protections

Price and Tax history

DateEventPrice
Sep 30, 2025
Source: Zillow Rentals
ListingRemoved
$2,900
Aug 13, 2025
Source: Zillow Rentals
Listed For Rent
$2,900
Aug 10, 2010
Source: N/A
Sold
$57,500
Jun 18, 2010
Source: Agent Provided
Listed For Sale
$57,500
Oct 6, 2005
Source: N/A
Sold
$125,000

Frequently asked questions about 244 Jefferson St

  • What is 244 Jefferson St estimated to be worth?
    Trulia's estimated value for 244 Jefferson St in Oregon, WI is $322,500.
  • What is the price history for 244 Jefferson St?
    244 Jefferson St in Oregon, WI last sold for $57,500 in August 2010.
  • Is Oregon a buyer's or seller's market?
    Oregon is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Oregon?
    The median sale price in Oregon is $535K. That is down $4.17K from the prior month.
  • Does 244 Jefferson St have air conditioning?
    Yes, 244 Jefferson St in Oregon, WI has air conditioning.
  • Does 244 Jefferson St have laundry facilities?
    Yes, 244 Jefferson St in Oregon, WI has in-unit laundry.

Homes for rent near 244 Jefferson St

Skip to last item
Skip to first item

Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.
Skip to last item
  • Results are loading
Skip to first item