You have some beautiful details in the brick which would be lost if you painted it.

I would start with landscaping. I think you'll see a huge difference just doing that.

I like the updated railing in the inspirational photo, but I would never paint your beautiful brickwork, for aesthetics, for home value, and for practical ease of maintenance. It looks like your steps and walkways are made up of several different materials (though it is difficult to be sure), and I would want a plan that finds a material that works well with your home’s brick and use it for all hardscape. I like the generous size of your walkways and main steps.

You definitely need a good plan for landscaping since what is currently there does nothing to improve the home’s look. Is there room in the budget to hire a landscape designer? This is a large space, and it sounds like you have a number of changes that you want to make. Hiring someone to create a plan that can either be done in stages by you or hired out to contractors will give you a plan that meets your needs and budget while working with your home’s delightful character. Rather than horizontal fencing which to my mind isn’t in keeping with the home’s architecture, consider alternatives such as a metal fence like the one in your inspiration photo with a hedge planted on the yard side or both sides. Because the street is at a lower level, placing the hedge and fence at the top of the small slope will give you a head start on privacy.

Think about your goals for the space beyond privacy from the street and additional storage space. How do you want to use the area once enclosed? Shady patio? Kids’play area? Veggie garden? Flower garden? Low maintenance? Putting green? Volleyball or badminton court? Hot tub? Etc.

What are some potential issues that may need to be solved? Is the street busy enough for sound to be an issue in the front yard? Are you looking for shade? Do you want privacy from the neighbors as well as from the street? Do you need additional lighting or irrigation or other utilities? Are there drainage or other water related issues? Where will you want paths and other types of access? Etc.

Once you have thought through answers to these questions and others that you may find in landscape planning books (check at your local library), then you can begin a plan that will over time give you a yard that meets your family’s needs as well as suiting both your wish for an updated aesthetic and your home’s architecture.

DO NOT PAINT. You have a lovely home filled with character. As others have said, try landscaping first.

Lovely home. Remove that shrub - yew? - from in front of the picture window. Are the steps painted black? To me that is grabbing the attention away from a beautiful home.

I'm all for painting brick .... when the brick itself is UGLY. That's not the case here!

Instead of looking at examples of painted brick that are nice, look at unpainted ones until you find a trim scheme that speaks to you.

I could see updating, but not "modernizing" per se. I would embrace the house style as it is and try to make it the best it can be rather that trying to transform it into another period.

The big wooly brush hedge needs to go away and new plantings need to be installed. It needs a landscape PLAN with some trees. The yard looks vacant -- not protective and sheltering -- at the moment. There ought to be a surround of groundcover at the front slope instead of grass.

Limewash or German Mortar Smear the brick and get a landscaping plan that includes a TREE!

Please don't paint your perfect brick! Landscaping (a tree as Beverly said) and if you can afford them, new walkways will work wonders.

I like your place as is! As Patricia noted, it's in serious need of some landscaping. I'd put my money into hiring a landscape designer who could really make that front yard sing. I like the idea, too, of creating flower beds on either side of the front walkway to break up the grass expanse and add color.

Another voice here for the "Don't paint - rather, landscape" chorus. Get a landscape pro to draw you up a plan. It costs less than you think and will make your home look like a million bucks. You can do all the planting yourself to save money.

Ohhhh, I do love Beverly's inspirational photos.... hate to say it as I would not normally be in favor of this!

OK everybody, but the OP doesn't have to paint the brick. Could be stained, limewashed or German Mortar Smear. All depends on the location of the OP. Staining & Limewash is better in climates that experience below 0 temps.

Joanna Gaines didn't invent painting brick. Limewash has been used on homes in the US since the Pilgrims landed.

https://eieihome.com/articles/intro-limewashed-brick/

https://www.blesserhouse.com/limewashed-brick-exterior-makeover-reveal/

Really do love the lime washed you posted Beverly.

That with some new landscaping.. some cosmetic finishes such as a new light next to the door...........

If you decide to paint it, I think you'll have to add some Tudor trim to keep it from looking flat and boring.

Tudor Cottage Renovations and Alterations, South Orange, New Jersey · More Info

Private Residence - English / Tudor · More Info

Looks like a doll house, so very cute! Please don't paint that brick!

Why on earth paint over well built brickwork? Expensive to do and needing to be maintained forever. Just get the garden sorted out as the priority. At present you have a pretty house marooned in an empty space. It would look beautiful with a lush garden around it.

If you want to pursue the "Tudor" theme, they would not have wasted their time and resources lime washing brick. Limewash is an ancient technique but was for preserving wattle and daub walls or for cleanliness inside buildings. And for heavens sake don't to be tempted to stick on false 'beams'.