Hillsdale, OR homes for sale & real estate

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4344 SW Chesapeak Ave, Portland, OR 97239
4344 SW Chesapeak Ave, Portland, OR 97239
4344 SW Chesapeak Ave, Portland, OR 97239
ABOUT THIS HOME
Hillsdale, OR Homes for Sale
Mid-century modern home in desirable Council Crest Park. Vaulted living room with a fireplace opens to a Sunroom overlooking a gorgeous valley view. Dining room with slider to a large deck, perfect for summer BBQs. Kitchen with nook, skylight, and view of the beautiful back yard. Primary bedroom with walk-in shower plus 2 more bedrooms and a bathroom on the same level. Gleaming oak hardwood floors. The lower level features a family room with fireplace which opens to a den/office space. Incredible backyard greenhouse with electric, plumbing, and skylights—could be a great she-shed. Gardener’s delight with mature landscaping and an amazing array of plants and trees. Easy access to

$639,000

3 beds2.5 baths1,878 sq ft

4344 SW Chesapeak Ave, Portland, OR 97239

6,098 sq ft lot • 2 garage spots • Car-dependent

Deanna Wilson • Windermere Realty Trust

OPEN TODAY, 11AM TO 1PM

1254 SW Texas St, Portland, OR 97219
1254 SW Texas St, Portland, OR 97219
1254 SW Texas St, Portland, OR 97219
ABOUT THIS HOME
Hillsdale, OR Homes for Sale
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 modern convenience. Step inside to a welcoming, wood-clad entry with a slate floor and double closets. Rich hardwood floors, bay windows, and a dramatic brick-surround double fireplace ground the open-concept living and dining area. The spacious, kosher-friendly kitchen offers an island, cabinet pantry storage, and new floating Marmoleum flooring. An adjace

$819,000

3 beds2 baths2,912 sq ft

1254 SW Texas St, Portland, OR 97219

7,405 sq ft lot • 2 garage spots • Very walkable

Breylan Deal-Eriksen • Think Real Estate

2824 SW Illinois St, Portland, OR 97239
2824 SW Illinois St, Portland, OR 97239
2824 SW Illinois St, Portland, OR 97239
ABOUT THIS HOME
Hillsdale, OR Homes for Sale
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 Infrastructure: A newer sewer mainline to the street and updated wiring and PEX plumbing ensure peace of mind. • Luxurious Upstairs Bath: Enjoy a custom walk-in shower with Carrara Marble tile, a stylish vanity, and built-in shelving. • Energy Efficiency: The home features a new gas furn

$685,000

4 beds2 baths2,692 sq ft

2824 SW Illinois St, Portland, OR 97239

9,147 sq ft lot • Somewhat walkable

Anwar Bjyrd • Barnes Portland

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4416 SW Chesapeak Ave, Portland, OR 97239
4416 SW Chesapeak Ave, Portland, OR 97239
4416 SW Chesapeak Ave, Portland, OR 97239
ABOUT THIS HOME
Hillsdale, OR Homes for Sale
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, the custom kitchen is a true showpiece, featuring stainless steel appliances, bespoke cabinetry, and an oversized entertainer’s island—perfect for hosting gatherings of any size. The primary suite welcomes you with early 20th-century antique Japanese doors and floor-to-ceiling windo

$995,000

4 beds2.5 baths2,568 sq ft

4416 SW Chesapeak Ave, Portland, OR 97239

0.36 acre lot • Garage • Car-dependent

Steve Odermann • Windermere Realty Trust

940 SW Caldew Dr, Portland, OR 97219
940 SW Caldew Dr, Portland, OR 97219
940 SW Caldew Dr, Portland, OR 97219
ABOUT THIS HOME
Hillsdale, OR Homes for Sale
Large, renovated fourplex located in the heart of Hillsdale, one of Portland’s most walkable and charming neighborhoods. Strong tenant demand driven by proximity to shops, cafes, parks, and grocery. Excellent access to I-5, downtown Portland, OHSU, and the westside tech corridor. In-unit Washer and Dryer Recent Capital Improvements include new roof, new electrical panels and new water heaters. Property owner is a licensed realtor in the State of Oregon

$800,000

8 beds8 baths— sq ft

940 SW Caldew Dr, Portland, OR 97219

0.24 acre lot • Very walkable

Steve Roesch • NextHome Realty Connection

Property at 7820 SW 17th Dr, Portland, OR 97219, 8 beds, 4 baths

$850,000

8 beds4 baths3,392 sq ft

7820 SW 17th Dr, Portland, OR 97219

Josh Hackenjos • LUXE Forbes Global Properties

Property at 3132 SW Altadena Ter, Portland, OR 97239, 5 beds, 3 baths

$1,195,000

5 beds3 baths4,604 sq ft

3132 SW Altadena Ter, Portland, OR 97239

Macey Laurick • Windermere Realty Trust

Property at 7450 SW 17th Dr, Portland, OR 97219, 4 beds, 2.5 baths

$665,000

4 beds2.5 baths2,195 sq ft

7450 SW 17th Dr, Portland, OR 97219

Mathew Purcell • John L. Scott Market Center

Property at 6312 SW 27th Ave, Portland, OR 97239, 4 beds, 2.5 baths

$689,900

4 beds2.5 baths2,263 sq ft

6312 SW 27th Ave, Portland, OR 97239

Toni Mikel • Bluebird Real Estate

Property at 7005 SW 14th Ave, Portland, OR 97219, 5 beds, 3 baths

$773,000

5 beds3 baths2,856 sq ft

7005 SW 14th Ave, Portland, OR 97219

Vanessa Calvert • Cascade Hasson Sotheby's International Realty

Property at 7323 SW Nevada Ter, Portland, OR 97219, 3 beds, 2.5 baths

$699,000

3 beds2.5 baths2,001 sq ft

7323 SW Nevada Ter, Portland, OR 97219

Brandon Buchanan • Real Broker

Property at 2409 SW Nebraska St #10, Portland, OR 97239, 2 beds, 2 baths

$269,000

2 beds2 baths886 sq ft

2409 SW Nebraska St #10, Portland, OR 97239

Pam Waldman • Keller Williams Realty Portland Premiere

Property at 1663 SW Westwood Dr, Portland, OR 97239, 3 beds, 3 baths

$975,000

3 beds3 baths3,424 sq ft

1663 SW Westwood Dr, Portland, OR 97239

Richard Caplan • Windermere Realty Trust

Property at 4970 SW 31st Dr, Portland, OR 97239, 2 beds, 2 baths

$693,000

2 beds2 baths1,889 sq ft

4970 SW 31st Dr, Portland, OR 97239

Kathy Kollas • Navigate The Way Home, LLC

Property at 4933 SW 18th Pl, Portland, OR 97239, 4 beds, 3 baths

$799,900

4 beds3 baths3,052 sq ft

4933 SW 18th Pl, Portland, OR 97239

Chris Suarez • Keller Williams Sunset Corridor

Property at 6020 SW 18th Dr, Portland, OR 97239, 3 beds, 3.5 baths

$1,148,900

3 beds3.5 baths3,301 sq ft

6020 SW 18th Dr, Portland, OR 97239

Robert Law • John L Scott Portland SW

Property at 6022 SW 18th Dr, Portland, OR 97239, 4 beds, 4 baths

$1,135,900

4 beds4 baths3,085 sq ft

6022 SW 18th Dr, Portland, OR 97239

Robert Law • John L Scott Portland SW

Property at 8046 SW Capitol Hill Rd, Portland, OR 97219, 3 beds, 2 baths

$549,000

3 beds2 baths2,058 sq ft

8046 SW Capitol Hill Rd, Portland, OR 97219

Kurt Davidson • Keller Williams Capital City

Property at 7922 SW Capitol Hill Rd, Portland, OR 97219, 5 beds, 2 baths

$620,000

5 beds2 baths1,908 sq ft

7922 SW Capitol Hill Rd, Portland, OR 97219

Kimberly Russell • Knipe Realty ERA Powered

Property at 2832 SW Bertha Blvd, Portland, OR 97239, 3 beds, 1.5 baths

$639,000

3 beds1.5 baths1,332 sq ft

2832 SW Bertha Blvd, Portland, OR 97239

Sue Hill-Sullivan • Windermere Realty Trust

Property at 6454 SW Parkhill Dr, Portland, OR 97239, 4 beds, 3 baths

$875,000

4 beds3 baths3,440 sq ft

6454 SW Parkhill Dr, Portland, OR 97239

Kendall Bergstrom-Delancellotti • Cascade Hasson Sotheby's International Realty

Property at 4323 SW Twombly Ave, Portland, OR 97239, 4 beds, 3 baths

$875,000

4 beds3 baths3,160 sq ft

4323 SW Twombly Ave, Portland, OR 97239

Sarita Dua • Keller Williams Sunset Corridor

Property at 992 SW Westwood Dr, Portland, OR 97239, 4 beds, 3.5 baths

$995,000

4 beds3.5 baths4,070 sq ft

992 SW Westwood Dr, Portland, OR 97239

Don Courtney • Realty One Group Prestige

Property at 6611 SW Parkhill Dr, Portland, OR 97239, 5 beds, 3 baths

$649,000

5 beds3 baths2,733 sq ft

6611 SW Parkhill Dr, Portland, OR 97239

Maureen Hotchkiss • The Agency Portland

Property at 1035 SW Bertha Blvd #4, Portland, OR 97219, 2 beds, 1 bath

$230,000

2 beds1 bath882 sq ft

1035 SW Bertha Blvd #4, Portland, OR 97219

Sharon Wenger • MORE Realty

Property at 6415 SW Terwilliger Blvd, Portland, OR 97239, 3 beds, 3 baths

$775,000

3 beds3 baths2,157 sq ft

6415 SW Terwilliger Blvd, Portland, OR 97239

Andrea Parmelee • Premiere Property Group, LLC

Property at 230 SW Florida St, Portland, OR 97219, 5 beds, 3.5 baths

$1,125,000

5 beds3.5 baths3,664 sq ft

230 SW Florida St, Portland, OR 97219

Aaron Moomaw • Cascade Hasson Sotheby's International Realty

Property at 4700 SW Northwood Ave, Portland, OR 97035, 7 beds, 5 baths

$4,250,000

7 beds5 baths5,999 sq ft

4700 SW Northwood Ave, Portland, OR 97035

Patrick Clark • Inhabit Real Estate

Property at 6442 SW Parkhill Dr, Portland, OR 97239, 3 beds, 3 baths

$1,194,000

3 beds3 baths3,315 sq ft

6442 SW Parkhill Dr, Portland, OR 97239

Lynda O'Neill • John L. Scott

Property at 6902 SW 2nd Ave, Portland, OR 97219, 4 beds, 3 baths

$599,900

4 beds3 baths2,390 sq ft

6902 SW 2nd Ave, Portland, OR 97219

Michael Skillman • John L Scott Portland SW

Property at 5634 SW Menefee Dr, Portland, OR 97239, 4 beds, 3.5 baths

$949,999

4 beds3.5 baths3,039 sq ft

5634 SW Menefee Dr, Portland, OR 97239

Tim Wilson • Knipe Realty ERA Powered

Property at 6008 SW 18th Dr, Portland, OR 97239, 3 beds, 3 baths

$998,900

3 beds3 baths2,855 sq ft

6008 SW 18th Dr, Portland, OR 97239

Robert Law • John L Scott Portland SW

Property at 4731 SW 18th Dr, Portland, OR 97239, 4 beds, 3 baths

$1,395,000

4 beds3 baths3,219 sq ft

4731 SW 18th Dr, Portland, OR 97239

Marcia Walsh • Where, Inc

Property at 6254 SW Burlingame Ave Unit A, Portland, OR 97239, 3 beds, 3.5 baths

$1,549,000

3 beds3.5 baths3,199 sq ft

6254 SW Burlingame Ave Unit A, Portland, OR 97239

Brent Barker • Coldwell Banker Bain

Property at SW Vermont St, Portland, OR 97219

$599,900

— beds— baths— sq ft

SW Vermont St, Portland, OR 97219

Darryl Bodle • Keller Williams Realty Portland Premiere

Property at 1739 SW Logan St, Portland, OR 97219

$319,900

— beds— baths— sq ft

1739 SW Logan St, Portland, OR 97219

Darryl Bodle • Keller Williams Realty Portland Premiere

Property at SW Westwood Ct, Portland, OR 97239

$250,000

— beds— baths— sq ft

SW Westwood Ct, Portland, OR 97239

Evan Nelson • eXp Realty, LLC

Property at SW Ralston Dr, Portland, OR 97239

$524,900

— beds— baths— sq ft

SW Ralston Dr, Portland, OR 97239

Jeff Roberts • John L. Scott

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Average home prices near Hillsdale, OR

Cities

Neighborhoods

Northwest Portland homes for sale
$499,000
Goose Hollow homes for sale
$325,000
Sellwood-Moreland homes for sale
$582,000
Dunthorpe homes for sale
$2,272,000
Southwest homes for sale
$650,000
Corbett homes for sale
$552,200
Multnomah Village homes for sale
$575,000
Southwest Portland homes for sale
$725,000
Eastmoreland homes for sale
$895,000
Downtown Portland homes for sale
$325,000

Hillsdale, OR real estate trends

All Home Types trends in Hillsdale, OR

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$759,900

+4.8% YoY | May 2025

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

May 2025

Growth

% YoY

Hillsdale, OR

$759,900

+4.8%

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Popular Markets in Oregon

All information provided is deemed reliable but is not guaranteed and should be independently verified. The content relating to real estate for sale on this web site comes in part from the IDX program of the RMLS of Portland Oregon. Real estate listings held by brokerage firms other than Redfin are marked with the RMLS logo and detailed information about these properties includes the names of the listing brokers. Copyright © 2025 RMLS, Portland, Oregon. Data Last Updated Sat Jun 14 2025

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