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Hillsdale Houses for Sale

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  • /28

    $580,000

    • 2 Beds
    • 2.5 Baths
    • 1,716 Sq Ft

    6601 SW Parkhill Dr, Portland, OR 97239

    Welcome home! This stunning 3-bedroom, 2.5-bathroom Portland home is full of updates, minutes to OHSU, and ready for your personal touches! Walking into the home, you'll be greeted with sleek new LVP flooring and huge windows, which look out onto the forest behind the home. The living room opens to the kitchen, which is sure to please with quartz counters, new cabinet doors, and stainless

    Agent Photo

    Nick Shivers

    Keller Williams PDX Central

    (503) 461-5315

    6601 SW Parkhill Dr, Portland, OR 97239
  • /25

    $899,000

    • 3 Beds
    • 2.5 Baths
    • 2,351 Sq Ft

    4130 SW Chesapeak Ave, Portland, OR 97239

    Located in the sought-after SW Hills neighborhood, this meticulously remodeled home seamlessly combines modern updates with timeless charm. The spacious open-concept living area is flooded with natural light, highlighted by soaring ceilings and exposed beams that add character. Enjoy effortless indoor-outdoor living with multiple decks, ideal for both entertaining and unwinding in the serene,

    Alexandra Daggett Knipe Realty ERA Powered

    4130 SW Chesapeak Ave, Portland, OR 97239
  • /48

    $2,350,000

    • 4 Beds
    • 4.5 Baths
    • 5,460 Sq Ft

    5570 SW Menefee Dr, Portland, OR 97239

    Perched on a bluff in the hills of Southwest Portland, this exceptional 1928 Tudor Revival commands sweeping views of Mt. Hood and the Willamette River. Inside, the home strikes an artful balance between modern comfort and historic authenticity. Rich red oak flooring pairs beautifully with original millwork, custom ironwork, and period brass fixtures. Graceful Tudor archways and coved ceilings

    Kristen Kohnstamm Cascade Hasson Sotheby's International Realty

    5570 SW Menefee Dr, Portland, OR 97239
  • /42

    $975,000

    • 3 Beds
    • 3 Baths
    • 3,424 Sq Ft

    1663 SW Westwood Dr, Portland, OR 97239

    Unobstructed views with main floor living. Classic 1950's design with Primary suite and second bedroom plus separate full bath on main. Enjoy your view looking south along the Willamette river with your morning coffee from private deck, and then your wine watching the sunsets. Living room, kitchen and primary suite all with straight on views. Plenty of living areas on lower level. Family room

    Richard Caplan Windermere Realty Trust

    1663 SW Westwood Dr, Portland, OR 97239
  • /29

    $639,000

    • 3 Beds
    • 1.5 Baths
    • 1,332 Sq Ft

    2832 SW Bertha Blvd, Portland, OR 97239

    This Northwest contemporary home offers a peaceful retreat while keeping you close to everything Southwest Portland has to offer. With its unique perch, the home feels like a private sanctuary surrounded by nature. Enter inside to a warm and inviting main level where the open living and dining areas flow seamlessly into a well-appointed kitchen. Sliding doors open to a spacious, refinished deck,

    Sue Sullivan Windermere Realty Trust

    2832 SW Bertha Blvd, Portland, OR 97239
  • /48

    $974,900 Open Sun 1PM - 3PM

    • 3 Beds
    • 3 Baths
    • 2,855 Sq Ft

    6008 SW 18th Dr, Portland, OR 97239

    OPEN SUNDAY 7/27 FROM 1 TO 3PM. Stunning Contemporary Model Home – Tehran Exclusive by Main Street Development. Model close-out opportunity with 2/1 interest rate buy-down! Designed by renowned Portland architect Ralph Tahran, this home offers high-end finishes, 9' ceilings, and abundant natural light with sweeping territorial views. Open floor plan features engineered hardwood floors, tiled

    Libby Benz Windermere Realty Trust

    6008 SW 18th Dr, Portland, OR 97239
  • /42

    $989,000

    • 4 Beds
    • 3 Baths
    • 3,016 Sq Ft

    2245 SW Martha St, Portland, OR 97239

    Forest-Backed Mid-Century Oasis with Saltwater Pool – 13 Mins to Downtown. Spectacular home for entertaining, awesome location in Hillsdale area backing to beautiful light filled forest, with gorgeous inground saltwater pool and deck, plus fern garden, perfect for pool parties or just fun for the family. Completely private, overlooking the beautiful forest. Light and bright Mid-century home has

    Helen Hoyt Portland Creative Realtors

    2245 SW Martha St, Portland, OR 97239
  • /47

    $1,175,000 Open Thu 3PM - 6PM

    • 5 Beds
    • 4 Baths
    • 3,888 Sq Ft

    5707 SW Menefee Dr, Portland, OR 97239

    A truly rare find, this exceptional Portland property offers not only a beautifully updated 3,888 sq ft Colonial-style main residence, but also a fully permitted, light-filled 1BD/1BA accessory dwelling unit (ADU) privately perched above the garage. With soaring ceilings, treetop views, and its own separate entrance, the ADU offers the flexibility so many buyers are seeking today—ideal for

    Lisa Field Cascade Hasson Sotheby's International Realty

    5707 SW Menefee Dr, Portland, OR 97239
  • /47

    $1,075,000

    • 5 Beds
    • 3.5 Baths
    • 3,664 Sq Ft

    230 SW Florida St, Portland, OR 97219

    This exceptional custom-built home offers 180 degree sweeping views of the city, river, and mountain ranges. Just minutes from downtown Portland, OHSU, and Multnomah Village, you’ve found the perfect blend of peaceful living and city convenience. The main level features an open floor plan with high ceilings accented by box beams and oversized windows showcasing the breathtaking views. The chef’s

    Lauren Moomaw Cascade Hasson Sotheby's International Realty

    230 SW Florida St, Portland, OR 97219
  • /40

    $839,000

    • 3 Beds
    • 3 Baths
    • 2,309 Sq Ft

    6945 SW 7th Ave, Portland, OR 97219

    This Mid Century Modern is the perfect fit for those with an eye for character, and a highly desired location. The cutest ADU, nicely furnished, is an added bonus which has the third bed/bath. It has a long rental history on Airbnb. With its own separate entrance, it is perfect for a teen, in-laws, or generational living.Natural light floods the front of the home, drawing you towards the windows.

    Kim Kress Windermere Heritage

    6945 SW 7th Ave, Portland, OR 97219
  • /48

    $995,000

    • 4 Beds
    • 2.5 Baths
    • 2,568 Sq Ft

    4416 SW Chesapeak Ave, Portland, OR 97239

    Perched high on a double lot, this artistically remodeled Mid-Century Daylight Ranch offers sweeping, unobstructed views stretching from the Coast Range to the eastern foothills. Thoughtfully designed for privacy and serenity, the home is sited and landscaped to minimize sightlines from neighboring properties—allowing you to fully enjoy the expansive view deck and peaceful surroundings. Inside,

    Steve Odermann Windermere Realty Trust

    4416 SW Chesapeak Ave, Portland, OR 97239
  • /45

    $850,000

    • 4 Beds
    • 3 Baths
    • 3,160 Sq Ft

    4323 SW Twombly Ave, Portland, OR 97239

    This is a wonderful home in an amazing close-in SW Portland location on a quarter acre lot. Welcome to this gardener's delight! This mid-century charmer has a versatile floorplan and is warm and inviting. The spacious living room with fireplace is light and bright due to the many windows. It opens to the dining area, kitchen and private back deck. The kitchen is central to everything and is open

    Sarita Dua Keller Williams Sunset Corridor

    4323 SW Twombly Ave, Portland, OR 97239
  • /38

    $689,000

    • 3 Beds
    • 2 Baths
    • 2,118 Sq Ft

    6731 SW 11th Dr, Portland, OR 97219

    Looking for a home with a bit of mid-century vibe in the sought-after neighborhood in Hillsdale? Here is it! This gem offers many functional updates for today’s everyday living inside and out. As you enter this inviting home, you will be welcomed by the view of seasonal trees off picture-perfect windows in the living room. Practical floor plan provides accommodations for all. The lower level

    Sohee Anderson Where, Inc

    6731 SW 11th Dr, Portland, OR 97219
  • /42

    $600,000

    • 3 Beds
    • 2 Baths
    • 1,369 Sq Ft

    7149 SW 3rd Ave, Portland, OR 97219

    Open House 7/19-7/20 11-1:00 Mid-Century Post-Modern Gem with Income-Producing Studio. This Northwest Mid-Century post-modern home showcases soaring ceilings, crisp architectural lines, and an effortless indoor-outdoor flow. Inside, the great room centers around a sleek VALOR gas fireplace with original mahogany mantle and shelves, floor-to-ceiling windows opening out to a private deck

    Tammy Sanderson John L. Scott

    7149 SW 3rd Ave, Portland, OR 97219
  • /41

    $540,000

    • 3 Beds
    • 1 Bath
    • 986 Sq Ft

    7323 SW 4th Ave, Portland, OR 97219

    Opportunity knocks! This sweetly renovated 3-bedroom, 1-bath ranch home in Burlingame/Hillsdale is the perfect blend of comfort and convenience. The desirable single-level layout flows efficiently with an open and airy living room, dining area, and kitchen upon entry. Bedrooms are nestled quietly through the back hall with garden views. Step out to your private backyard oasis, where an in-ground

    Heidi Hopfer Neighbors Realty

    7323 SW 4th Ave, Portland, OR 97219
  • /35

    $639,000

    • 3 Beds
    • 2.5 Baths
    • 2,103 Sq Ft

    7886 SW Capitol Hill Rd, Portland, OR 97219

    Beautiful and spacious detached condo in a prime location near Multnomah Village and Hillsdale. This home features a modern open floor plan with high ceilings, detailed millwork, custom built-ins, a cozy gas fireplace, and designer touches throughout. The kitchen is equipped with quartz countertops, a large island, stainless steel appliances, and a walk-in pantry.The generous primary suite offers

    Sarah Ruffner Where, Inc

    7886 SW Capitol Hill Rd, Portland, OR 97219
  • /37

    $675,000

    • 5 Beds
    • 3 Baths
    • 2,545 Sq Ft

    1124 SW Chestnut Dr, Portland, OR 97219

    Make memories for many years to come in this warm and welcoming tri-Level with flexible spaces with room to live and grow. The gracious step-saver floor plan has a remodeled kitchen, tons of storage, three fireplaces, and great wall space for art. Enjoy basking in warm summer evenings on the front porch watching people strolling by. A large bonus room in the lower level is perfect for media,

    Carolyn Weinstein Cascade Hasson Sotheby's International Realty

    1124 SW Chestnut Dr, Portland, OR 97219
  • /41

    $699,000

    • 3 Beds
    • 3 Baths
    • 2,045 Sq Ft

    3306 SW Fairmount Blvd, Portland, OR 97239

    IMPROVED PRICE! Set along tree-lined Fairmount Blvd, this Northwest Contemporary offers a sense of layered privacy just minutes from downtown and OHSU. Native plantings and shifting valley views surround the four-level home, where large windows, built-ins, and hardwood floors create a warm, functional interior. Multiple decks and garden pockets extend the living space outdoors, while nearby

    Craig Weintz Vetiver Street Real Estate

    3306 SW Fairmount Blvd, Portland, OR 97239
  • /43

    $799,900

    • 3 Beds
    • 2 Baths
    • 2,912 Sq Ft

    1254 SW Texas St, Portland, OR 97219

    ** BACK ON MARKET AT NO FAULT OF SELLER - BUYER GOT COLD FEET ** Swaddled into the hillside above the best Fred Meyer, you'll find this handsome home offering hallmark elements of mid-century architecture. This gorgeous ranch-style home in Portland’s sought-after Hillsdale neighborhood features clean lines, open spaces, and an effortless connection to the outdoors, while thoughtful updates offer

    Breylan Deal-Eriksen Think Real Estate

    1254 SW Texas St, Portland, OR 97219
  • /22

    $650,000

    • 4 Beds
    • 2 Baths
    • 2,692 Sq Ft

    2824 SW Illinois St, Portland, OR 97239

    Charming Historic Home with Modern Upgrades and Incredible Potential Don't miss out on this delightful and unique home, full of character and ready for someone who appreciates the beauty of older homes. Nestled in a peaceful neighborhood with quiet neighbors on all sides, this property offers a blend of timeless charm and modern convenience.Some key features & upgrades include:• Modern

    Anwar Bjyrd Barnes Portland

    2824 SW Illinois St, Portland, OR 97239
  • /38

    $799,000

    • 8 Beds
    • 4 Baths
    • 3,392 Sq Ft

    7820 SW 17th Dr, Portland, OR 97219

    Purchase to live in one unit and rent out the others or rent all units. Built in 1973, the Mossy Brae Apartments are situated between Multnomah and Burlingame neighborhoods just off of SW Barbur Boulevard in SW Portland. This is a great entry-level or owner-occupied investment with an achievable value-add opportunity. The subject property is comprised of four (4) total units, all units are

    Josh Hackenjos LUXE Forbes Global Properties

    7820 SW 17th Dr, Portland, OR 97219
  • /36

    $645,000

    • 4 Beds
    • 2.5 Baths
    • 2,195 Sq Ft

    7450 SW 17th Dr, Portland, OR 97219

    Large Price Reduction | Updated Daylight Ranch with Seasonal Mt. Hood ViewsSet on a quiet street in SW Portland, this charming daylight ranch offers timeless appeal and thoughtful updates throughout. Enjoy seasonal views of Mt. Hood from your freshly rebuilt and expansive deck (2023), perfect for relaxing or entertaining.Inside, refinished hardwood floors (2022) shine alongside fresh interior

    Mathew Purcell John L. Scott Market Center

    7450 SW 17th Dr, Portland, OR 97219
  • /17

    $625,000

    • 4 Beds
    • 2.5 Baths
    • 2,263 Sq Ft

    6312 SW 27th Ave, Portland, OR 97239

    Quiet Cul-De-Sac Mid-Century in Highly Desirable Hillsdale/Multnomah Village Area! Stylish, Clean and Roomy! Beautiful original hardwoods on main floor. 2 wood-burning fireplaces. Enclosed sunroom off kitchen. Great lower level bonus room plus laundry area, lots of built-ins, half bath and office with closet and brand-new carpet. Big 2-car garage with built-ins. Large lot with mature trees and

    Toni Mikel Bluebird Real Estate

    6312 SW 27th Ave, Portland, OR 97239
  • /26

    $950,000

    • 4 Beds
    • 3.5 Baths
    • 4,070 Sq Ft

    992 SW Westwood Dr, Portland, OR 97239

    This spacious Colonial home in the walkable Hillsdale neighborhood sits on .29 acres (2 tax lots!) in a lush parklike setting. Very well maintained over ethe years with fully renovated kitchen (2023), the main floor provides vast entertainment space + massive bonus room. All bedrooms upstairs with 3.5 bathrooms, and storage galore. Two rooms include en-suite for Primary bedroom use, with a second

    Don Courtney Realty One Group Prestige

    992 SW Westwood Dr, Portland, OR 97239
  • /48

    $975,000

    • 4 Beds
    • 4 Baths
    • 3,172 Sq Ft

    3045 SW Gaston Ave, Portland, OR 97239

    Very motivated seller just invested $20k to remedy inspection concerns.New price now below appraised value for this beautifully updated 1924 English cottage! The floor plan is versatile with several areas having many possible uses,including a 715 sq/ft,1bed,1bath suite on the lower level currently being used as an income generating ADU (approx.$2,800/mth), mother-in-law suite,or easily integrated

    Sheila McMurray eXp Realty, LLC

    3045 SW Gaston Ave, Portland, OR 97239
  • /37

    $649,000

    • 5 Beds
    • 3 Baths
    • 2,733 Sq Ft

    6611 SW Parkhill Dr, Portland, OR 97239

    They don't make them like this anymore! Solid beams of old growth timber, vaulted tongue and groove ceilings, and wood floors on both levels are the highlights of this mid century modern home. The sleek, functional design offers comfortable main floor living with a large living room, cozy sitting room, an open kitchen, a primary bedroom suite and two additional bedrooms. The lower level, with an

    Maureen Hotchkiss The Agency Portland

    6611 SW Parkhill Dr, Portland, OR 97239
  • /44

    $1,975,000

    • 6 Beds
    • 7 Baths
    • 6,870 Sq Ft

    3440 SW Doschview Ct, Portland, OR 97239

    Spectacular sunset vistas and exceptional private living await in this exclusive gated West Hills View Estates masterpiece that has been reimagined in high style and offers stunning outdoor entertaining, water garden grounds, a grand sense of scale throughout, and ADA accessible guest accommodations with 2nd kitchenette. Enter to a breathtaking mezzanine great room with 25' beamed ceilings and

    Kevin Hall Cascade Hasson Sotheby's International Realty

    3440 SW Doschview Ct, Portland, OR 97239
  • /47

    $3,995,000

    • 7 Beds
    • 6 Baths
    • 5,999 Sq Ft

    4700 SW Northwood Ave, Portland, OR 97239

    A picture-perfect Roscoe Hemenway designed home that soars above the city skyline unlike any other in Portland. Designed and sited to maximize views of Mt. Adams, Helens, Hood and the Willamette River, this view estate is close in to all that Portland has to offer. The private winding drive leads to a secluded, park-like setting punctuated by a variety of outdoor entertaining spaces, including a

    Patrick Clark Inhabit Real Estate

    4700 SW Northwood Ave, Portland, OR 97239
  • /35

    $1,194,000

    • 3 Beds
    • 3 Baths
    • 3,315 Sq Ft

    6442 SW Parkhill Dr, Portland, OR 97239

    Located in the highly sought-after SW Hills, this beautifully remodeled home offers stunning panoramic views of Mt. Hood, Mt. St. Helens, and the Willamette River from multiple rooms and the expansive back deck. Situated on a peaceful, private dead-end street, providing a perfect blend of tranquility and convenience.A major quality remodel was completed in 2022, updating the home with modern

    Lynda O'Neill John L. Scott

    6442 SW Parkhill Dr, Portland, OR 97239
  • /23

    $589,900

    • 4 Beds
    • 3 Baths
    • 2,390 Sq Ft

    6902 SW 2nd Ave, Portland, OR 97219

    Hillsdale - Original Owner - East Facing - 2 X-Large View Decks - 3 Bedroom, Den, 3 Bath, 2,390SF - Well Maintained Home with 70's Inspired Interior - Cosmetic Updates Needed - Area Homes to $1.1 mill+ / Lots of upside potential. Living Room features Large Fireplace, Floor to Ceiling Windows & Deck Access - Spacious Family Room with Covered Deck Access - Primary Suite & 2nd/3rd Bedrooms on main

    Michael Skillman John L Scott Portland SW

    6902 SW 2nd Ave, Portland, OR 97219
  • /43

    $1,549,000

    • 3 Beds
    • 3.5 Baths
    • 3,199 Sq Ft

    6254 SW Burlingame Ave Unit A, Portland, OR 97239

    NEW ON MARKET AFTER SIGNIFICANT UPGRADES. Portland's best Location and neighborhood in desirable West Hills. Enjoy panoramic views of the forest in the home and relax with nature off of the new sun deck system engineered on three levels adds over 1500 sq. ft. of outdoor living space. New deck system, presidential roofing, new luxury grade carpets, exterior and interior paint, new lighting,

    Brent Barker PC Coldwell Banker Bain

    6254 SW Burlingame Ave Unit A, Portland, OR 97239
  • /34

    $949,999

    • 4 Beds
    • 3.5 Baths
    • 3,039 Sq Ft

    5634 SW Menefee Dr, Portland, OR 97239

    Check out this Amazing move-in ready home! Coveted Terwilliger Heights! Updated home sits on 7600 square foot lot. 4 bedrooms, Den, 3.5 bath spacious well-maintained home with undeniable charm and unique character and Large bedrooms. The main floor has a spacious living room with wood burning fireplace, formal dining, and den with hardwood floors. The kitchen and bathrooms have beautiful tile

    Tim Wilson Knipe Realty ERA Powered

    5634 SW Menefee Dr, Portland, OR 97239
  • /29

    $1,069,800 New Construction

    • 4 Beds
    • 4 Baths
    • 2,985 Sq Ft

    6026 SW 18th Dr, Portland, OR 97239

    This stunning contemporary home, designed by Portland's acclaimed architect, Ralph Tahran, and built by Main Street Development, an esteemed fourth generation local builder, is one of nine unique homes in this exclusive in this development. It features 4 bedrooms (one on the main living area with a full bath adjoining), a covered deck with a sweeping territorial view, and an ADU with separate

    Robert Law John L Scott Portland SW

    6026 SW 18th Dr, Portland, OR 97239
  • /37

    $1,069,800 New Construction

    • 4 Beds
    • 4 Baths
    • 3,085 Sq Ft

    6022 SW 18th Dr, Portland, OR 97239

    This stunning contemporary home, designed by Portland's renowned architect, Ralph Tahran, and crafted by Main Street Development, an esteemed fourth generation local builder, is one of nine exclusive designs in this premier development. This proposed presale features 4 bedrooms, plus a main floor office/guest bedroom with an adjoining full bath with tub/shower, high end finishes, and 9 foot

    Robert Law John L Scott Portland SW

    6022 SW 18th Dr, Portland, OR 97239
  • /48

    $1,079,800 New Construction

    • 3 Beds
    • 3.5 Baths
    • 3,301 Sq Ft

    6020 SW 18th Dr, Portland, OR 97239

    This stunning contemporary home, designed by Portland's acclaimed architect, Ralph Tahran, and built by Main Street Development, an esteemed fourth generation local builder, is one of nine unique homes in this exclusive in this development. It features 3 bedrooms, a main floor office, an upstairs large loft/family room. The home offers high end finishes, a gourmet kitchen with premium cabinets,9

    Robert Law John L Scott Portland SW

    6020 SW 18th Dr, Portland, OR 97239
  • /28

    $1,545,000 New Construction

    • 4 Beds
    • 3.5 Baths
    • 2,832 Sq Ft

    4453 SW Melville Ave, Portland, OR 97239

    Gorgeous contemporary custom designed plan with 420 square foot deck off master bedroom and covered deck off great room. Top of the line modern finishes and appliances. Meet with the builder's designer to select yours. Very private setting at end of street in a great neighborhood with quick downtown/Council Crest/Hillsdale access. You may also customize your home by adjusting the floor plan or

    Robert Law John L Scott Portland SW

    4453 SW Melville Ave, Portland, OR 97239

Why Live in Hillsdale

Hillsdale, a family-friendly neighborhood in Southwest Portland, is known for its walkability and diverse architectural styles. Residents can easily walk to various amenities, including well-known restaurants, coffee shops, grocery stores, and schools. The neighborhood features a mix of contemporary traditional, ranch-style, and mid-century modern homes, with spacious lots and many properties offering scenic views from the hills. Hillsdale's housing options include single-family homes and some condos, with prices for single-family homes generally ranging from $600,000 to $900,000. The area is served by highly rated schools such as Rieke Elementary School, Robert Gray Middle School, and West Hills Christian School. Hillsdale offers numerous things to do, including exploring George Himes Park's 35 acres of forested land, enjoying smaller parks like DeWitt Park and Albert Kelly Park, and visiting the popular dog park at Hillsdale Park. The neighborhood boasts a variety of dining options, such as Seasons & Regions Seafood Grill, Verde Cocina, and Vertical Diner, along with a McMenamins location in the Hillsdale Shopping Center. For groceries, residents frequent the Fred Meyer on the south end of the neighborhood. Hillsdale is conveniently located four miles south of downtown Portland, accessible via Pacific Highway West or the Route 54 bus. It is also close to medical facilities, including OHSU Hospital and Portland VA Medical Center, and 15 miles from Portland International Airport. The neighborhood hosts community events like the Hillsdale Winter Light Festival and the Hillsdale Blueberry Pancake Breakfast, as well as a year-round farmers' market at Rieke Elementary.

Home Trends in Hillsdale, OR

Housing Trends

Median Sale Price
$767,500
Median Single Family Sale Price
$800,000
Median Townhouse Sale Price
$484,950
Median 2 Bedroom Sale Price
$252,500
Median 1 Bedroom Sale Price
$230,000
Average Price Per Sq Ft
$323
Number of Homes for Sale
38
Last 12 months Home Sales
120
Months of Supply
3.80
Median List Price
$799,900
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
12%
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