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Bridlemile Homes for Sale

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  • /33

    $1,070,000

    • 4 Beds
    • 3 Baths
    • 2,676 Sq Ft

    5745 SW Gaines Ct, Portland, OR 97221

    A soulful NW Contemporary reimagined with intention and elevated in all the best ways. Rooted in warmth yet elevated in style, this home stands apart as one of Wilcox West’s rare gems. Clean architectural lines, oversized windows, and sun-filled spaces set the tone from the moment you arrive. The welcoming porch entry leads into a chic landing highlighted by a custom light fixture and modern

    Marie Boatsman Berkshire Hathaway HomeServices NW Real Estate

    5745 SW Gaines Ct, Portland, OR 97221
  • /36

    $850,000

    • 3 Beds
    • 2.5 Baths
    • 1,802 Sq Ft

    5138 SW Santa Monica Ct, Portland, OR 97221

    The One You’ve Been Waiting For—A Beautifully Remodeled Retreat in SW Portland! Tucked on a quiet cul-de-sac, this single-level stunner blends timeless charm with modern ease. From the moment you enter through the grand wrought iron double doors, you feel it—this home is something special. The light-filled living spaces flow effortlessly, from living room, dining room, to family room with

    Cinnamin Webb Redfin

    5138 SW Santa Monica Ct, Portland, OR 97221
  • /46

    $799,000

    • 5 Beds
    • 3 Baths
    • 3,379 Sq Ft

    4740 SW Lowell Ct, Portland, OR 97221

    Welcome to this beautifully cared for Bridlemile home, tucked beneath a tranquil forest canopy on a quiet cul-de-sac. Blending timeless character with smart updates, this home offers the perfect balance of comfort, space, and natural beauty in one of Portland’s most coveted neighborhoods. Step inside to an airy, open main level where the living room, dining room, and family room all look out over

    Darcie Alexander Think Real Estate

    4740 SW Lowell Ct, Portland, OR 97221
  • /41

    $1,075,000

    • 3 Beds
    • 2.5 Baths
    • 3,920 Sq Ft

    4043 SW Westdale Dr, Portland, OR 97221

    Modern Treehouse in highly sought after Montmore neighborhood!Tucked away on the sunny side of the West Hills, this one-of-a-kind custom home in the coveted Montmore neighborhood offers a rare blend of serenity, style, and community. Surrounded by mature trees and flooded with natural light, the home feels like a tranquil retreat—with all the modern comforts beautifully updated for everyday

    Chaley Mcvay Redfin

    4043 SW Westdale Dr, Portland, OR 97221
  • /44

    $995,000

    • 4 Beds
    • 3 Baths
    • 3,328 Sq Ft

    4200 SW 53rd Ave, Portland, OR 97221

    Magical Mid-Century Remod in Close-In SW Portland! You will LOVE this Location, Near Everything Raleigh Hills|Hillsdale|Vermont Hills|Multnomah Village! Gorgeous Vaulted Living Room with Peaceful, Private Views to Trees. Spectacular Entertaining In + Out, Door from Kitchen leads to BBQ Space on Large Partial Covered Deck. Enjoy Expansive Lower Patio with Views of Trees + Yard. Cozy Fireplace

    Jen Wiley Cascade Hasson Sotheby's International Realty

    4200 SW 53rd Ave, Portland, OR 97221
  • /48

    $1,275,000

    • 6 Beds
    • 5 Baths
    • 6,021 Sq Ft

    4040 SW 53rd Place, Portland, OR 97221

    Open Saturday 10/25/2025 from 1:00pm to 3:00pm Grand residence in Wilcox Estates designed by renowned architect Kirtland Cutter.He worked with the Wilcox Family in the early 1900's to build their summer Wilcox Manor home & additional homes and structures That included this grand architectual gem . Cutter designed many well known homes, lodges and clubs includng the Autzen Mansion In NE PDX.This

    Robert Atkinson Where, Inc

    4040 SW 53rd Place, Portland, OR 97221
  • /48

    $1,199,800

    • 5 Beds
    • 3.5 Baths
    • 3,366 Sq Ft

    3644 SW 48th Place, Portland, OR 97221

    Totally turn key Mid Century Daylight ranch in arguably the best west side neighborhood Wilcox Estates! One of the only walkable neighborhoods in the Southwest Hills of Portland includes a neighborhood pool and tennis courts. This one truly has it all: Huge great room floor plan with open layout is an entertainers dream! Gourmet chefs kitchen has a large island with seating for four. Adjacent

    Brian Getman Where, Inc

    3644 SW 48th Place, Portland, OR 97221
  • /43

    $1,379,000

    • 5 Beds
    • 4.5 Baths
    • 4,809 Sq Ft

    3620 SW 60th Place, Portland, OR 97221

    2019 total remodel of this traditional Colonial home in Bridlemile/ Raleigh Hills. Perfect for growing families with 4 bedrooms on the same level. This house is located only minutes to everything that makes living in the Southwest Hills so incredible. Just 10 minutes into downtown via multiple routes, 5 minutes to Jesuit HS, Oregon Episcopal School, Catlin Gable School, & Portland Golf Club. 15

    Brian Getman Where, Inc

    3620 SW 60th Place, Portland, OR 97221
  • /47

    $545,000 Open Tue 12PM - 2PM

    • 2 Beds
    • 1 Bath
    • 1,604 Sq Ft

    6200 SW Seymour St, Portland, OR 97221

    Mid century ranch packed with period details on more than a half acre in a cushy section of Southwest. Living space all on one seamless level. Retro-chic living room with original brick wood burning fireplace and killer floor-to-ceiling windows. Hardwood floors throughout. Sophisticated formal dining room has a sweet built-in that adds charm to any cozy dinner party. Darling kitchen with cheery

    Beth Benner Real Broker

    6200 SW Seymour St, Portland, OR 97221
  • /22

    $775,000

    • 5 Beds
    • 3 Baths
    • 3,575 Sq Ft

    4225 SW 51st Place, Portland, OR 97221

    Charming Day Ranch that is well cared for in the desirable Bridlemile Neighborhood of the Southwest Hills. Situated on a large private and manicured lot in a quiet cul-de-sac with close proximity to Hamilton Park. This expansive home offers a wide variety of living options with a primary bedroom on the main level as well as the potential for multi-generational living with a spacious walk out

    Paul Johnson MORE Realty

    4225 SW 51st Place, Portland, OR 97221
  • /42

    $1,650,000

    • 4 Beds
    • 3.5 Baths
    • 4,437 Sq Ft

    3718 SW Hillside Dr, Portland, OR 97221

    Tucked into the SW Hills, this modern home was designed to embrace light, space, and sweeping south-facing views. Built in 2019, its clean, contemporary architecture spans 4,437 sq ft with an effortless sense of balance and flow. Expansive windows flood the open main level with natural light, connecting a statement kitchen featuring a 6-burner Fulgor Milano cooktop and range, Viking appliances,

    Suzann Baricevic-Murphy Where, Inc.

    3718 SW Hillside Dr, Portland, OR 97221
  • /48

    $1,850,000

    • 4 Beds
    • 4.5 Baths
    • 7,008 Sq Ft

    3450 SW 44th Ave, Portland, OR 97221

    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

    Erin Livengood Where Real Estate Collaborative

    3450 SW 44th Ave, Portland, OR 97221
  • /48

    $795,000

    • 2 Beds
    • 2.5 Baths
    • 2,248 Sq Ft

    3040 SW 36th Ave, Portland, OR 97221

    Open Sunday 10/26/2025 from 1:00pm to 3:30pm. A special charming and updated cottage style traditional with coastal flair nestled in Portland's West Hills with expansive territorial and valley views. All on a neat corner lot.Great floor plan with open flow and rich dark wood floors, designer touches and lovely built in features. Cook's kitchen with granite counters,stainless appliances including

    Robert Atkinson Where, Inc

    3040 SW 36th Ave, Portland, OR 97221
  • /12

    $319,000

    • Land
    • 0.42 Acre
    • $759,524 per Acre

    6336 SW Seymour St Unit B, Portland, OR 97221

    Spacious and private .42 acre lot, ideal for your dream home or development opportunity for up to 5 cottages! Tree lined flag lot offers extra privacy, with endless possibility to build what your heart desires. Add a swimming pool, garden, or sport court! Lot is level, with utilities already connected. Nestled in a quiet neighborhood near Scholls Ferry Rd., home is convenient to New Seasons, Fred

    Joe Liu Keller Williams PDX Central

    6336 SW Seymour St Unit B, Portland, OR 97221
  • /48

    $699,900

    • 4 Beds
    • 3 Baths
    • 2,199 Sq Ft

    4819 SW Hamilton St, Portland, OR 97221

    New fence and a 50,000 price reduction!!!! Open House Sunday 2-4pm! Total remodel of this mid-century home in the heart of the desirable Bridlemile neighborhood. Tucked into a large lot with a pass-through driveway, this home blends timeless mid-century design with thoughtful, modern updates. Inside features a magazine-worthy kitchen with custom cabinetry, quartz counters, spacious island and

    Angela Stevens Keller Williams Realty Professionals

    4819 SW Hamilton St, Portland, OR 97221
  • /47

    $899,000 Open Sat 1PM - 3PM

    • 4 Beds
    • 3.5 Baths
    • 3,279 Sq Ft

    5701 SW Hamilton St, Portland, OR 97221

    OPEN HOUSE'S SATURDAY 11/1 1-3PM + SUNDAY 11/2 12-2PM Main-level living with flexible live + work layout on nearly half an acre. This beautifully updated 1962 Daylight Ranch offers timeless design, abundant natural light, and a private creek-side setting. Multiple skylights and French doors fill the home with natural light and seamless indoor–outdoor connection. The main level features a spacious

    Shannon Baird Windermere Realty Trust

    5701 SW Hamilton St, Portland, OR 97221
  • /46

    $925,000 Open Tue 11:30AM - 2PM

    • 3 Beds
    • 3.5 Baths
    • 2,971 Sq Ft

    4041 SW 55th Dr, Portland, OR 97221

    Open House: Tuesday 28th - 11:30 to 2:00 You’ll love living in this sought-after neighborhood of SW Portland, just minutes from Hwy 26 and all the best amenities in and around the greater Portland Metro. 4041 is stunning and boasts an excellent layout that accommodates large gatherings both inside and out, featuring two outstanding patios. You’ll feel right at HOME when you walk in this

    Sarah Malarkey Opt

    4041 SW 55th Dr, Portland, OR 97221
  • /35

    $375,000

    • 2 Beds
    • 1.5 Baths
    • 1,640 Sq Ft

    4819 SW Beaverton Hillsdale Hwy, Portland, OR 97221

    This townhome blends natural beauty, smart layout, and unbeatable convenience—all just minutes from the city. Out back, a private deck overlooks a year-round creek lined with trees that transform with the seasons. The setting is peaceful and full of life: songbirds throughout the day, owls calling at night, and the occasional deer passing through. Inside, the main level features wood floors,

    Selina Herrera MORE Realty

    4819 SW Beaverton Hillsdale Hwy, Portland, OR 97221
  • /11

    $574,000

    • Land
    • 0.39 Acre
    • $1,471,795 per Acre

    4142 SW Hamilton St, Portland, OR 97221

    Just a 2-minute walk to Hamilton Park and Bridlemile Elementary, this rare property in a beloved SW Portland neighborhood is ready for your vision. The existing home is livable and financeable with conventional lending—offering a unique path to secure buildable land without the typical cash-only hurdle. This lot .39 acre lot offers the chance to build your dream home on a quiet dead-end street,

    Kathleen O'Donnell ODonnell Group Realty

    4142 SW Hamilton St, Portland, OR 97221
  • /48

    $3,000,000

    • 7 Beds
    • 7 Baths
    • 10,963 Sq Ft

    4414 SW Semler Way, Portland, OR 97221

    Mid-century modern masterpiece by renowned architect Walter Gordon, celebrated for seamlessly blending indoor and outdoor spaces. This architectural gem features floor-to-ceiling glass walls, skylights, expansive rooms, travertine floors, accent walls, a sunken living room, built-in bookcases, and soaring ceilings. The primary ensuite will absolutely wow you with glass wall, fireplace,

    Dill Ward eXp Realty, LLC

    4414 SW Semler Way, Portland, OR 97221
  • /6

    $324,900

    • Land
    • 0.3 Acre
    • $1,083,000 per Acre

    4255 SW Beaverton Hillsdale Hwy, Portland, OR 97221

    Southwest Portland development opportunity! +/-13,211 square feet of RM2 land. Outstanding location near downtown, Hillsdale, Multnomah, shops, employers and transit! Possible to build up to 14 units, Buyer to do it's own due diligence. Developers package available upon request.

    Devin Bourne Bespoke Realty

    4255 SW Beaverton Hillsdale Hwy, Portland, OR 97221
  • /20

    $499,500 Pre-Foreclosure

    • 3 Beds
    • 2 Baths
    • 1,148 Sq Ft

    4623 SW 55th Place, Portland, OR 97221

    Find your perfect balance of nature, neighborhood, and next chapter in this light-filled Bridlemile retreat. Thoughtfully maintained this home makes every day feel easy and connected.Sunlight pours through large windows and skylights, creating a warm, open feel that’s ideal for cozy nights in or relaxed weekend entertaining. Step outside to unwind on the front or back deck, surrounded by a lovely

    Jennifer Singer Keller Williams Sunset Corridor

    4623 SW 55th Place, Portland, OR 97221
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