16

4-Bedroom Homes for Sale in Southwest Hills

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  • /48

    $1,800,000

    • 4 Beds
    • 3.5 Baths
    • 4,079 Sq Ft

    4183 SW Greenleaf Dr, Portland, OR 97221

    This is the one you’ve been waiting for—an architectural stunner in Portland’s coveted Southwest Hills neighborhood, where design, technology, and serenity meet. Perched along SW Greenleaf Drive, this showpiece home combines striking lines, panoramic views, and modern updates throughout—a rare blend of iconic mid-century design and forward-thinking smart home living.From the moment you arrive,

    Agent Photo

    Peter Cutile

    Modern Realty

    (503) 714-9117

    4183 SW Greenleaf Dr, Portland, OR 97221
  • /33

    $1,600,000

    • 4 Beds
    • 5 Baths
    • 4,550 Sq Ft

    5046 SW Hilltop Ln, Portland, OR 97221

    Enchanting 1942 home sits on a private, beautiful acre on one of Portland's most sought after streets. Brimming with timeless charm, the home offers four bedrooms, a sunroom, and two separate office spaces—ideal for modern living. 2 car attached garage plus additional 2 car detached garage great for additional storage or hobby space. Thoughtful architectural details and a warm, inviting layout

    Marcia Walsh Where, Inc

    5046 SW Hilltop Ln, Portland, OR 97221
  • /47

    $2,595,000

    • 4 Beds
    • 3.5 Baths
    • 9,741 Sq Ft

    1825 SW Vista Ave, Portland, OR 97201

    Welcome home to this Georgian colonial luxury residence. Situated perfectly at the entrance to the Portland heights popular neighborhood grid district. Positioned on an elevated lot to capture the daily city scapes, Mt. St Helens and the river. Interior spaces will never disappoint with the darker wood floors and paneling set against white walls with exquisite period craftmanship. Carefully

    Libby Benz Windermere Realty Trust

    1825 SW Vista Ave, Portland, OR 97201
  • /33

    $1,650,000

    • 4 Beds
    • 3.5 Baths
    • 4,114 Sq Ft

    3425 SW 57th Ave, Portland, OR 97221

    Experience elevated living in this stunning custom luxury home, perfectly positioned against a peaceful greenbelt for ultimate privacy. Soaring 12ft ceilings & rich wood floors span the main level, creating an impressive, inviting atmosphere. The living room features a cozy gas fireplace & expansive picture windows that bring the outdoors in. The gourmet kitchen is a chef’s dream, boasting a

    Ariel Sasser Property Group NW

    3425 SW 57th Ave, Portland, OR 97221
  • /40

    $1,795,000

    • 4 Beds
    • 3.5 Baths
    • 3,372 Sq Ft

    5210 SW Hewett Blvd, Portland, OR 97221

    Modern Retreat in the Woods reimagined by Linden Brown Architecture invites you into this SW facing light-filled, private sanctuary. Tucked into the trees yet just minutes from the heart of the city, this home offers the perfect balance of privacy, style, and convenience. Clean architectural lines, rich natural light, beautiful custom oak built-ins, reclaimed brick accent walls all help to define

    Courtney Davies Where, Inc

    5210 SW Hewett Blvd, Portland, OR 97221
  • /45

    $1,600,000

    • 4 Beds
    • 3.5 Baths
    • 4,260 Sq Ft

    2505 SW Hillcrest Dr, Portland, OR 97201

    Just minutes to the city, and in one of the top rated locations in Portland for public school, Hillcrest Drive allows privacy and a contemporary ADU space for a nanny or guests! Grand rooms, French doors, 3 fireplaces, classic hardwood floors, flat yard space - welcome home.

    Krystin Bassist Windermere Realty Trust

    2505 SW Hillcrest Dr, Portland, OR 97201
  • /44

    $2,250,000

    • 4 Beds
    • 4.5 Baths
    • 5,650 Sq Ft

    4616 SW Humphrey Ct, Portland, OR 97221

    Step into timeless elegance with this stunning Robert A.M. Stern-inspired shingle-style home, exuding the quintessential charm of the Hamptons. Nestled on a generous .4-acre corner lot, this 1998 masterpiece boasts a red shingle exterior accented by white columned converted porches, stucco facades, and copper-topped chimneys. Inside, soaring ceilings greet you in the grand entryway, where a

    Kristina Opsahl Where, Inc

    4616 SW Humphrey Ct, Portland, OR 97221
  • /47

    $1,395,000

    • 4 Beds
    • 3 Baths
    • 3,827 Sq Ft

    1805 SW Elizabeth St, Portland, OR 97201

    Elegant Colonial nestled in the heart of Portland Heights! This thoughtfully designed home offers a flowing floor plan with gleaming hardwoods on both the main and upper levels, four inviting fireplaces, and delightful custom touches throughout. Sunlight pours in through expansive windows, framing lovely views and meticulously maintained landscaping. The chef’s kitchen features marble

    Steve Rosling Cascade Hasson Sotheby's International Realty

    1805 SW Elizabeth St, Portland, OR 97201
  • /41

    $865,000

    • 4 Beds
    • 4.5 Baths
    • 2,425 Sq Ft

    1625 SW Montgomery St Unit C, Portland, OR 97201

    Modern design meets elevated city living in this architecturally distinct end-unit townhome, thoughtfully crafted to take full advantage of panoramic views of the Portland skyline and nearby mountains. Abundant natural light pours through oversized windows, highlighting the home’s refined finishes and attention to detail.The open-concept main level features warm hardwood flooring and a designer

    Cody Gibson Keller Williams PDX Central

    1625 SW Montgomery St Unit C, Portland, OR 97201
  • /45

    $990,000

    • 4 Beds
    • 4 Baths
    • 3,752 Sq Ft

    5007 SW Humphrey Park Rd, Portland, OR 97221

    Tucked into the peaceful, tree-lined hills of Southwest Portland, The Hobby Haus blends vintage 1970s character with modern flexibility. Surrounded by trees and lush landscaping, this private woodland retreat offers the perfect place to live, work, and play. With 6 spacious bedrooms, there’s room to spread out—for remote work, guests, creative pursuits, or multi-generational living. Host

    Amy McMahon Windermere Realty Trust

    5007 SW Humphrey Park Rd, Portland, OR 97221
  • /47

    $3,995,000

    • 4 Beds
    • 6.5 Baths
    • 7,890 Sq Ft

    1551 SW Upper Hall St, Portland, OR 97201

    Perched high above the city in Portland’s prestigious West Hills, this striking modern masterpiece captures breathtaking 180-degree views that stretch from the snow-capped peak of Mt. Hood to the shimmering towers of downtown. A private gated drive leads to this architecturally bold glass-and-steel residence, where sleek lines and organic materials create an appealing blend of drama and warmth.

    Terry Sprague LUXE Forbes Global Properties

    1551 SW Upper Hall St, Portland, OR 97201
  • /48

    $1,099,999

    • 4 Beds
    • 2 Baths
    • 2,330 Sq Ft

    2440 SW Hoffman Ave, Portland, OR 97201

    ASSUMABLE MORTGAGE AT 2.25%! Please inquire for more information.Perched above the city with one of Portland’s most iconic views, this stunningly remodeled home offers luxury, privacy, and unbeatable convenience. Tucked off Broadway on secluded Hoffman Avenue, it feels like a private retreat while being moments from downtown and Portland’s best amenities. Nearly every room showcases panoramic

    Marcus Brown Realty One Group Prestige

    2440 SW Hoffman Ave, Portland, OR 97201
  • /48

    $1,225,000

    • 4 Beds
    • 3 Baths
    • 3,263 Sq Ft

    2645 SW Upper Drive Place, Portland, OR 97201

    PREPARE TO BE CAPTIVATED! Don’t let the humble facade of this charming Portland Heights Cape Cod deceive you. Its traditional formal entertaining spaces - defined by updated wood sash windows, hardwood floors, crown molding and a wood-burning fireplace - flow seamlessly into a 2020 kitchen addition fit for the finest of chefs! Unparalleled culinary luxury and convenience define the heart of

    Ginger Burke Cascade Hasson Sotheby's International Realty

    2645 SW Upper Drive Place, Portland, OR 97201
  • /24

    $699,000

    • 4 Beds
    • 2.5 Baths
    • 2,405 Sq Ft

    1369 SW Broadway Dr, Portland, OR 97201

    Welcome to this stunning 3-level home perched above it all with breathtaking views of the surrounding hills. Built in 1994, this one-of-a-kind 4-bedroom, 2.5-bath home combines privacy, comfort, and modern convenience—including smart home features and a level 2 EV charger in the attached 2-car garage.The expansive top-floor owner’s suite offers a private sanctuary with panoramic views, two

    Kimberly Minasian Neighbors Realty

    1369 SW Broadway Dr, Portland, OR 97201
  • /48

    $940,000

    • 4 Beds
    • 5 Baths
    • 4,970 Sq Ft

    1767 SW Prospect Dr, Portland, OR 97201

    Price reduced on this beautifully preserved 1906 home. Perched up in the desirable Portland Heights neighborhood combines historic charm with modern convenience. FRESHLY REFINISHED HARDWOODS! As you step inside, you'll be greeted by high ceilings and an inviting traditional floor plan, perfect for both entertaining and everyday living. The home features classic period moldings and paneling,

    Quinn Irvine MORE Realty

    1767 SW Prospect Dr, Portland, OR 97201
  • /44

    $898,000

    • 4 Beds
    • 3 Baths
    • 3,402 Sq Ft

    2705 SW English Ln, Portland, OR 97201

    ***NEW PRICE!!!***Private Daylight Ranch in Portland Heights just 1 block from Portland Heights Park, close to Washington Park and Council Crest Trail. Located at the end of cul-de-sac is this 4 bedroom, 3 bath, just over 3400 square foot home. Close enough to be a short drive to downtown but far enough away to feel like you're in a neighborhood-this floor plan offers flexibility and separation

    Justin Harnish Harnish Company Realtors

    2705 SW English Ln, Portland, OR 97201

Home Trends in Southwest Hills, OR

Housing Trends

Median Sale Price
$387,500
Median Single Family Sale Price
$574,995
Median Townhouse Sale Price
$429,774
Median 2 Bedroom Sale Price
$150,000
Median 1 Bedroom Sale Price
$217,000
Average Price Per Sq Ft
$318
Number of Homes for Sale
12
Last 12 months Home Sales
97
Months of Supply
1.50
Median List Price
$528,482
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
-72%
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