Luxury homes for sale & real estate in Southwest Hills, OR

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ABOUT THIS HOME
Luxury Home for sale in Southwest Hills, OR:
Set on nearly an acre of private, south-facing land, this beautifully updated mid-century home offers exceptional design, functionality, and breathtaking valley vistas. The thoughtfully designed floor plan provides mostly main-floor living, including generous living and dining areas, a spectacularly remodeled kitchen/family room, and three luxurious ensuite bedrooms. Perfectly suited for entertaining, the home seamlessly separates social and private spaces. On the lower level, discover a spacious great room, a fourth bedroom (no closet), a full bath, and a fun indoor pool with a sauna — ideal for year-round enjoyment. Outdoor living is just as impressive, with a large deck for gatheri

$1,850,000

4 beds5 baths7,008 sq ft

3450 SW 44th Ave, Portland, OR 97221

Spacious great room • Sprawling backyard • 0.88 acre lot

Erin Livengood • Windermere Realty Trust

ABOUT THIS HOME
Luxury Home for sale in Southwest Hills, OR:
Nestled in Portland’s prestigious West Hills, this extraordinary estate offers sweeping views of the city skyline, Willamette River, and Cascade Mountains. Set on 1.17 acres of gated, park-like grounds, the property blends historic elegance with modern luxury. Originally built in 1887 by JJ McCaffrey and thoughtfully updated in 1928 by renowned architects Jacobberger and Smith, the residence showcases timeless craftsmanship and architectural distinction. The home has been exceptionally maintained over decades of ownership. Inside, experience approximately 10,000sf of living space that unfolds across four levels, featuring elaborate moldings, stained glass windows, rich wood

$4,995,000

6 beds7 baths9,829 sq ft

1816 SW Hawthorne Ter, Portland, OR 97201

Historic elegance • Modern luxury • 1.17 acre lot

Patrick Clark • Christie's International Real Estate Evergreen

ABOUT THIS HOME
Luxury Home for sale in Southwest Hills, OR:
This elegant Brentwood Drive home (original owner) blends classic charm with modern comfort in one of the city’s most desirable neighborhoods. Extremely well taken care of. Recent updates, including a new roof, fresh exterior paint, all new windows on the south side, make it move-in ready. The . 43-acre lot offers exceptional privacy, including a 20x40-foot swimming pool, a pool house, and plenty of space for entertaining or relaxing. Inside the home, you’ll find three fireplaces, a walnut-paneled den perfect for a home office, and a workout room with nearby storage. A security system for peace of mind, a generator, and a spacious outbuilding addition for convenience.

$1,795,000

3 beds3 baths3,856 sq ft

3484 SW Brentwood Dr, Portland, OR 97201

Workout room • Pool house • Walnut-paneled den

JoAnn Dennis • Berkshire Hathaway HomeServices NW Real Estate

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ABOUT THIS HOME
Luxury Home for sale in Southwest Hills, OR:
Portland Heights Classic with Modern Elegance. Gracefully set above the street on a desirable corner lot in the heart of Portland Heights. This timeless residence exudes sophistication, architectural charm, and thoughtful craftsmanship at every turn. Expansive, light-filled interiors flow seamlessly between formal and casual living spaces, enhanced by elegant French doors, custom millwork, and warm natural light. The gourmet kitchen is a chef’s delight, showcasing custom cabinetry, a serviced Viking range with all new parts, and a newly installed dishwasher — all complemented by refined finishes that make cooking and entertaining effortless. The inviting living room centers arou

$1,375,000

4 beds4 baths4,269 sq ft

2547 SW Hillcrest Dr, Portland, OR 97201

Cutting garden • Landscaped grounds • Private balcony

Gabriela Mann • Keller Williams Realty Professionals

ABOUT THIS HOME
Luxury Home for sale in Southwest Hills, OR:
Step into the rich history and luxury of the Joseph Gaston House, an architectural masterpiece built in 1911 by William C. Knighton in Portland's West Hills. This captivating estate offers a timeless allure with its elegant living spaces, and impeccable craftsmanship. Perched on 3/4 of an acre in The Grid, it commands panoramic views of the city skyline and mountains, creating an idyllic backdrop for everyday living. Features include intricate moldings, high ceilings, stunning primary bedroom with walk-in closet and spacious bathroom with steam shower, and remarkable 5,000-bottle cellar. Outside, a beautiful patio overlooks downtown Portland, providing a serene retreat to unwind and take in

$2,999,000

5 beds7 baths8,752 sq ft

1960 SW 16th Ave, Portland, OR 97201

Walk-in closet • 5 • Intricate moldings

Marcia Walsh • Where, Inc

Property at 4141 SW Washouga Ave, Portland, OR 97239, 2 beds, 2 baths

$1,050,000

2 beds2 baths2,336 sq ft

4141 SW Washouga Ave, Portland, OR 97239

Kenneth Avery • eXp Realty, LLC

Property at 3333 SW Heather Ln, Portland, OR 97201, 3 beds, 4 baths

$1,050,000

3 beds4 baths4,018 sq ft

3333 SW Heather Ln, Portland, OR 97201

Sharon Fleming • Coldwell Banker Bain

Property at 1757 SW Prospect Dr, Portland, OR 97201, 4 beds, 5 baths

$875,000

4 beds5 baths3,952 sq ft

1757 SW Prospect Dr, Portland, OR 97201

Tim Kaelin • Coldwell Banker Professional

Property at 2412 SW 15th Ave, Portland, OR 97201, 5 beds, 4 baths

$1,778,500

5 beds4 baths4,501 sq ft

2412 SW 15th Ave, Portland, OR 97201

Macey Laurick • Windermere Realty Trust

Property at 6145 SW Sweetbriar Ct, Portland, OR 97221, 4 beds, 5 baths

$1,050,000

4 beds5 baths4,018 sq ft

6145 SW Sweetbriar Ct, Portland, OR 97221

Jennifer Turner • Lovejoy Real Estate

Property at 3840 SW Martins Ln, Portland, OR 97239, 4 beds, 4 baths

$1,500,000

4 beds4 baths3,405 sq ft

3840 SW Martins Ln, Portland, OR 97239

Marisa Swenson • Modern Homes Collective

Property at 1450 SW Davenport St, Portland, OR 97201, 3 beds, 3 baths

$949,900

3 beds3 baths3,409 sq ft

1450 SW Davenport St, Portland, OR 97201

Chris Suarez • Keller Williams Sunset Corridor

Property at 2608 SW Fairmount Blvd, Portland, OR 97239, 4 beds, 3 baths

$1,185,000

4 beds3 baths2,990 sq ft

2608 SW Fairmount Blvd, Portland, OR 97239

Megan Jumago-Simpson • Keller Williams Realty Professionals

Property at 2850 SW Fairmount Blvd, Portland, OR 97239, 4 beds, 3 baths

$1,198,500

4 beds3 baths3,602 sq ft

2850 SW Fairmount Blvd, Portland, OR 97239

Jenny Bright • Urban Pacific Real Estate

Property at 3718 SW Hillside Dr, Portland, OR 97221, 4 beds, 4 baths

$1,650,000

4 beds4 baths4,437 sq ft

3718 SW Hillside Dr, Portland, OR 97221

Suzann Baricevic Murphy • Where, Inc.

Property at 3620 SW Dosch Rd, Portland, OR 97239, 5 beds, 6 baths

$2,790,000

5 beds6 baths5,848 sq ft

3620 SW Dosch Rd, Portland, OR 97239

Mimi McCaslin • LUXE Forbes Global Properties

Property at 1980 SW Terrace Dr, Portland, OR 97201, 3 beds, 3 baths

$1,395,000

3 beds3 baths4,208 sq ft

1980 SW Terrace Dr, Portland, OR 97201

Corey Rudolph • Cascade Hasson Sotheby's International Realty

Property at 2635 SW Sherwood Pl, Portland, OR 97201, 3 beds, 2 baths

$875,000

3 beds2 baths2,358 sq ft

2635 SW Sherwood Pl, Portland, OR 97201

Janis Panfilio • Windermere Heritage

Property at 3250 SW Donner Way Ct, Portland, OR 97239, 5 beds, 4 baths

$1,150,000

5 beds4 baths3,316 sq ft

3250 SW Donner Way Ct, Portland, OR 97239

Christy MacColl • Windermere Realty Trust

Property at 5046 SW Hilltop Ln, Portland, OR 97221, 4 beds, 5 baths

$1,550,000

4 beds5 baths4,550 sq ft

5046 SW Hilltop Ln, Portland, OR 97221

Marcia Walsh • Where, Inc

Property at 2233 SW 18th Ave, Portland, OR 97201, 6 beds, 5 baths

$1,825,000

6 beds5 baths5,675 sq ft

2233 SW 18th Ave, Portland, OR 97201

John Nieland • Cascade Hasson Sotheby's International Realty

Property at 1948 SW Terrace Dr, Portland, OR 97201, 6 beds, 6 baths

$4,350,000

6 beds6 baths6,858 sq ft

1948 SW Terrace Dr, Portland, OR 97201

Suzann Baricevic Murphy • Where, Inc.

Property at 1558 SW Upper Hall St, Portland, OR 97201, 3 beds, 3 baths

$1,350,000

3 beds3 baths3,216 sq ft

1558 SW Upper Hall St, Portland, OR 97201

Krystin Bassist • Windermere Realty Trust

Property at 1551 SW Upper Hall St, Portland, OR 97201, 4 beds, 7 baths

$3,795,000

4 beds7 baths7,890 sq ft

1551 SW Upper Hall St, Portland, OR 97201

Terry Sprague • LUXE Forbes Global Properties

Property at 2844 SW Hillsboro St, Portland, OR 97239, 4 beds, 5 baths

$1,695,000

4 beds5 baths4,820 sq ft

2844 SW Hillsboro St, Portland, OR 97239

Scott Wilson • RE/MAX Equity Group

Property at 1205 SW Myrtle Dr, Portland, OR 97201, 3 beds, 5 baths

$2,750,000

3 beds5 baths4,880 sq ft

1205 SW Myrtle Dr, Portland, OR 97201

Marcia Walsh • Where, Inc

Property at 4311 SW Greenleaf Dr, Portland, OR 97221, 8 beds, 15 baths

$25,000,000

8 beds15 baths25,568 sq ft

4311 SW Greenleaf Dr, Portland, OR 97221

Terry Sprague • LUXE Forbes Global Properties

Property at 1442 SW Vista Ave, Portland, OR 97201, 5 beds, 5 baths

$2,075,000

5 beds5 baths4,197 sq ft

1442 SW Vista Ave, Portland, OR 97201

Aaron Moomaw • Cascade Hasson Sotheby's International Realty

Property at 2505 SW Hillcrest Dr, Portland, OR 97201, 4 beds, 4 baths

$1,495,000

4 beds4 baths4,260 sq ft

2505 SW Hillcrest Dr, Portland, OR 97201

Krystin Bassist • Windermere Realty Trust

Property at 4260 SW Mcdonnell Ter, Portland, OR 97239, 5 beds, 3 baths

$1,289,000

5 beds3 baths3,701 sq ft

4260 SW Mcdonnell Ter, Portland, OR 97239

Charles Carscallen • MORE Realty

Property at 5112 SW Hewett Blvd, Portland, OR 97221, 5 beds, 4 baths

$1,275,000

5 beds4 baths5,172 sq ft

5112 SW Hewett Blvd, Portland, OR 97221

Michael Green • Coldwell Banker Bain

Property at 4300 SW Hewett Blvd, Portland, OR 97221, 3 beds, 3 baths

$898,800

3 beds3 baths2,630 sq ft

4300 SW Hewett Blvd, Portland, OR 97221

William Gilliland • Windermere Realty Trust

Property at 1965 SW Montgomery Pl, Portland, OR 97201, 5 beds, 6 baths

$1,795,000

5 beds6 baths8,168 sq ft

1965 SW Montgomery Pl, Portland, OR 97201

Macey Laurick • Windermere Realty Trust

Property at 2732 SW Scholls Ferry Rd, Portland, OR 97221, 6 beds, 10 baths

$4,890,000

6 beds10 baths9,814 sq ft

2732 SW Scholls Ferry Rd, Portland, OR 97221

Terry Sprague • LUXE Forbes Global Properties

Property at 5210 SW Hewett Blvd, Portland, OR 97221, 4 beds, 4 baths

$1,745,000

4 beds4 baths3,372 sq ft

5210 SW Hewett Blvd, Portland, OR 97221

Courtney Davies • Where, Inc

Property at 2725 SW Sherwood Dr, Portland, OR 97201, 4 beds, 3 baths

$1,845,000

4 beds3 baths3,978 sq ft

2725 SW Sherwood Dr, Portland, OR 97201

Eric Hagstette • Inhabit Real Estate

Property at 1136 SW Davenport St, Portland, OR 97201, 5 beds, 5 baths

$2,150,000

5 beds5 baths5,518 sq ft

1136 SW Davenport St, Portland, OR 97201

Steve Odermann • Windermere Realty Trust

Property at 3800 SW Humphrey Blvd, Portland, OR 97035, 3 beds, 4 baths

$949,000

3 beds4 baths2,712 sq ft

3800 SW Humphrey Blvd, Portland, OR 97035

William Johnson • William E Johnson

Property at 1040 SW Myrtle Dr, Portland, OR 97201, 3 beds, 4 baths

$1,599,000

3 beds4 baths4,941 sq ft

1040 SW Myrtle Dr, Portland, OR 97201

Linda Heinrichs • Keller Williams Realty Portland Premiere

Property at 4616 SW Humphrey Ct, Portland, OR 97221, 4 beds, 5 baths

$2,250,000

4 beds5 baths5,650 sq ft

4616 SW Humphrey Ct, Portland, OR 97221

Kristina Opsahl • Where, Inc

Property at 3534 SW Gale Ave, Portland, OR 97239, 4 beds, 4 baths

$1,675,000

4 beds4 baths5,121 sq ft

3534 SW Gale Ave, Portland, OR 97239

Lisa Owens • Corcoran Prime

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Luxury Homes for Sale in Southwest Hills

There are currently 43 luxury homes for sale in Southwest Hills at a median listing price of $1.05M. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Southwest Hills stay on the market for 132 days and receive 1 offers. Popular neighborhoods include Northeast Portland, Northwest Portland, Sellwood-Moreland, North Portland, and Southwest Portland. This map is refreshed with the newest listings in Southwest Hills every 15 minutes.

In the past month, 7 homes have been sold in Southwest Hills. In addition to houses in Southwest Hills, there were also 18 condos, 1 townhouse, and 3 multi-family units for sale in Southwest Hills last month. Southwest Hills is a minimally walkable neighborhood in Multnomah County with a Walk Score of 32. Southwest Hills is home to approximately 7,539 people and 4,139 jobs. Find your dream home in Southwest Hills using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Southwest Hills are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Southwest Hills. If you're looking to sell your home in the Southwest Hills area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Southwest Hills with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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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 Wed Dec 03 2025

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