Take a step back in time at this turn of the century farm complete with original homestead, barn with a studio apartment for guests above and car parking on each side, multiple outbuildings and an 18 acre orchard. Beautifully landscaped with garden space, underground sprinklers and a greenhouse with power and heat. The little ones will love the miniature log cabin. This special property has been in the same family for many years. This is your chance to make it your own.
Listing Courtesy of Northwest MLS / Windermere Real Estate Walla Walla / Debbie Clark
$750,000 (USD)
Oregon Area Residential
Active
52357 Pleasant View Road Milton-Freewater, OR 97862
3 Bed
3 Baths
2704 sqft
MLS# 2382099
This beautiful property in the heart of Milton-Freewater's wine country is for sale for the first time in generations. With some updates, the home would be a perfect place to put down roots. Or pull out the orchard, plant some vines, and turn the home into a tasting room. Plenty of room to expand. Incredible views of the Blue Mountains. Easy drive to Walla Walla or Pendleton.
Listing Courtesy of Northwest MLS / Windermere Real Estate Walla Walla / Debbie Clark
$600,000 (USD)
Oregon Area Residential
Active
85327 Highway 339 Milton-Freewater, OR 97862
3 Bed
3 Baths
2704 sqft
MLS# 2435516
This updated, spacious, accessible home sits on over 3.5 beautiful acres with water rights and incredible mountain views. The 3 bedroom, 2.5 bath home was designed for easy living with wide doorways, a roll-in shower, open spaces and a ramp for ease of entry. Off the family room you'll find a large work-out room with a swim spa, tons of natural light and an air handler to eliminate the extra moisture. The pasture is fenced, crossed-fenced and has an area prepped and wired for power for your barn or shop. There is much more to this wonderful property situated just below the stateline-an easy drive to Walla Walla, Tri-Cities, Pendleton and Milton-Freewater.
Listing Courtesy of Northwest MLS / Windermere Real Estate Walla Walla / Debbie Clark
$500,000 (USD)
Oregon Area Multifamily
Active
327 Powell Road Milton-Freewater, OR 97862
Bed
0 Baths
sqft
MLS# 2447933
First time on the market! Discover this hidden 1.4-acre gem featuring four charming 1920s cabins surrounded by lush greenery with access from Powell and Lamb St. Bring your vision—there’s a huge shop, extra storage, shed, RV parking, and two trailer sites with full hookups. Endless possibilities await! Expand with more cabins, RV spots, or trailer pads for serious income potential, create a monthly rental community, launch VRBO getaways, or design your own private compound retreat. A fun, flexible property bursting with opportunity and charm!
Listing Courtesy of Northwest MLS / Windermere Real Estate Walla Walla / Debbie Clark
$500,000 (USD)
Oregon Area Land
Active
84658 Highway 11 Milton-Freewater, OR 97862
Bed
0 Baths
sqft
MLS# 2398410
Over 18 acres of rich farmland, with an irrigation well, buried mainline, and water rights in the heart of the Walla Walla Valley AVA, partially in The Rocks AVA. Possible location for a winery/tasting room. Great highway frontage between Walla Walla and Milton-Freewater. It has two curb cuts on Highway 11 and Appleton Rd footage. This is zoned EFU and is not a buildable lot.
Listing Courtesy of Northwest MLS / Windermere Real Estate Walla Walla / Debbie Clark
$475,000 (USD)
Oregon Area Residential
Pending
113 NE 7th Avenue Milton-Freewater, OR 97862
5 Bed
2 Baths
4147 sqft
MLS# 2377714
A Rare Gem – First Time on the Market in Over 30 Years! Step back in time with this one-of-a-kind, turn-of-the-century 5-bedroom, 2-bathroom home nestled on a beautifully landscaped 1/3-acre lot. Overflowing with character, this timeless residence features original hardwood floors, a sun-drenched dining room, a grand fireplace, and vintage charm at every turn. Enjoy your mornings with coffee on the inviting wraparound porch and unwind in the evenings on the private back deck. This lovingly maintained home offers the perfect blend of historic elegance and everyday comfort—a true treasure waiting for its next chapter.
Listing Courtesy of Northwest MLS / Windermere Real Estate Walla Walla / Debbie Clark
$450,000 (USD)
Oregon Area Residential
Active
826 Jacquelyn Street Milton-Freewater, OR 97862
4 Bed
2 Baths
2904 sqft
MLS# 2415191
This is a well-maintained home in a wonderful location, ready for its next owner. It sits at the very top of the hill, looking down on the city with beautiful views of the mountains beyond. It backs up to the wheat fields, which makes for a very private, fenced back yard, with mature landscaping. Inside, you'll find a large kitchen open to a sitting room or breakfast area, dining room, large living room, 2 bedrooms, a bath, and an office. Downstairs, there are 2 more bedrooms, a second bath, and access to the oversized 3-car garage. This special property has been in the same hands for many years and is now ready for its next owner as this seller prepares to downsize.
Listing Courtesy of Northwest MLS / Windermere Real Estate Walla Walla / Debbie Clark
$449,995 (USD)
Oregon Area Residential
Active
2 Lewis Circle Milton-Freewater, OR 97862
3 Bed
3 Baths
1879 sqft
MLS# 2420132
Due to clerical error home showed as pending. Not true. Waiting for new owner. This is your opportunity to own a unique home in the new development overlooking Milton-Freewater from the South hill. With beautiful, high-end finishes, views of the Walla Walla Valley & the Blue Mountains & huge windows that invite the natural light in, this Blue Plank custom build is one of a kind. The light quartz countertops make this open kitchen a joy to cook or entertain in. The large primary suite includes a walk-in closet & a beautiful tile shower. The large lot allows room for gardening, entertaining and play space. Enjoy the day from the shade of the large covered patio. This friendly, modern neighborhood is an easy drive to Walla Walla or Pendleton.
Listing Courtesy of Northwest MLS / Windermere Real Estate Walla Walla / Debbie Clark
$400,000 (USD)
Walla Walla Area Condominium
Active
1204 Lancer Drive Walla Walla, WA 99362
2 Bed
4 Baths
2300 sqft
MLS# 2409328
Spacious condo with beautiful views of the Walla Walla Country Club golf course and driving range. The kitchen, dining, and living rooms have a nice flow for daily living or entertaining. The dining room sliding door opens to a large deck. Upstairs, you’ll find 2 bedrooms, 2 full baths, and a laundry room. The walk-out basement has a family room with a wood stove and a second laundry room. This space could easily be converted to a 3rd bedroom or an office. Don’t miss the second garage in the lower level for your golf cart. The roof was replaced about 2 years ago, and the HVAC system is also newer.
Listing Courtesy of Northwest MLS / Windermere Real Estate Walla Walla / Debbie Clark
$360,000 (USD)
Oregon Area Residential
Active
1003 College Street Milton-Freewater, OR 97862
3 Bed
2 Baths
2546 sqft
MLS# 2429356
This beautiful home sits on the south hill, overlooking the city with views of the Blue Mountains. On the main level you'll find gleaming original wood floors, an updated kitchen with ss appliances, 2 bedrooms and a full bath. Upstairs is another bedroom and a large office or bonus room that is currently used as a fourth bedroom. The walk-out basement has the laundry room, a bath, a large family room with access to the patio and spacious backyard as well as a huge storage room. All this with easy access to shoppinng, schools and parks.
Listing Courtesy of Northwest MLS / Windermere Real Estate Walla Walla / Debbie Clark
$340,000 (USD)
Oregon Area Residential
Active
1009 College Street Milton-Freewater, OR 97863
3 Bed
2 Baths
1700 sqft
MLS# 2429474
This great home on the south hill is perfect for multi-generational living or anyone needing extra space. The main level contains two bedrooms, a full bath and laundry as well as living room with wood- burning fireplace , kitchen and access to to large deck which overlooks the lot and the city to the mountains. In the basement you'll find two additional bedrooms, another full bath a large family room with a fireplace and access to the covered patio and backyard. With over 1/3 acre, the lot is large enough for gardening, entertaining and play.
Listing Courtesy of Northwest MLS / Windermere Real Estate Walla Walla / Debbie Clark
$299,000 (USD)
Oregon Area Residential
Pending
183 S Andrea Street Milton-Freewater, OR 97862
3 Bed
2 Baths
1476 sqft
MLS# 2439183
This cozy home in a quiet neighborhood backs up to the bluff, creating a wonderfully private backyard space perfect for entertaining, gardening or play space. With one bedroom and a full bath on the main and 2 additional bedrooms and a second bath upstairs, it is the perfect size for first time buyers or anyone looking for manageable space. Don't miss the office or bonus room off the garage. Easy access to Walla Walla or Pendleton. Move in ready with all appliances included.
Listing Courtesy of Northwest MLS / Windermere Real Estate Walla Walla / Debbie Clark
$285,000 (USD)
Oregon Area Residential
Pending
127 Catherine Street Milton-Freewater, OR 97862
2 Bed
2 Baths
1472 sqft
MLS# 2420052
This lot includes 2 homes with separate addresses. Each has one bedroom and one bath. The front has a bonus room that would make a great office, nursery, or den. It also includes a small unfinished basement for storage. The back home has a cozy, open floor plan, a private back yard and covered patios, front and back. The shared garage has space for a single vehicle access from each end. This is ideal for multi-generational living or live in one and rent the other for help with the mortgage.
Listing Courtesy of Northwest MLS / Windermere Real Estate Walla Walla / Debbie Clark
$270,000 (USD)
Oregon Area Residential
Active
644 S Main Street Milton-Freewater, OR 97862
4 Bed
1 Baths
2206 sqft
MLS# 2231215
There is so much potential in this classic home in the heart of Milton-Freewater. Bring your ideas for maintaining the old world charm while adding modern updates. Near the library, shopping, schools, and parks. Just down the road from the public pool and the new bakeries. It’s an easy drive to Walla Walla or Pendleton.
Listing Courtesy of Northwest MLS / Windermere Real Estate Walla Walla / Debbie Clark
$250,000 (USD)
Oregon Area Land
Active
0 Trumbull Milton-Freewater, OR 97862
Bed
0 Baths
sqft
MLS# 2392260
This is a true unicorn. A buildable lot on an acre of land with beautiful mountain views in the middle of farmland, vineyards and orchards. While most of the property is under lease to an orchardist, there is space to build a home and use the shop. There is a private well and septic on the property and it is ready for your build. If you've ever wanted to live in the country without having land to maintain, this is for you. This is not a property you can drive by. Call your favorite realtor today.
Listing Courtesy of Northwest MLS / Windermere Real Estate Walla Walla / Debbie Clark
$150,000 (USD)
Oregon Area Residential
Pending
77523 Cold Springs Loop Weston, OR 97886
1 Bed
1 Baths
456 sqft
MLS# 2409080
Escape from the heat in this beautiful spot on the mountain. Enjoy the peace and quiet of nature with visits from the local wildlife. The cold months are just as beautiful and fun in this easy-to-reach spot. Imagine spending your holiday weeks on snowmobiles and skis. Cozy up to the wood stove after a long day in the snow. Barely 20 minutes from Milton-Freewater, 30-45 minutes from Walla Walla or Pendleton makes for an easy drive to spend time away from town.
Listing Courtesy of Northwest MLS / Windermere Real Estate Walla Walla / Debbie Clark