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5050 SW Hilltop Ln, Portland, OR 97221

$2,495,000

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Property Description

Driving along one of the Southwest Hills most coveted lanes, a story begins to unfold. It starts with the drive itself, past a collection of architecturally significant homes, before opening to a sun drenched 1.59 acre clearing where this charming residence sits with quiet confidence. It's easy to understand the draw: privacy, character, and a setting that feels tucked away from the world. And then there are the gardens. Love at first sight. Originally designed by Wade Pipes, the home captures his English Country style in a way that feels effortless rather than formal. It's less about making a statement and more about how the home makes you feel. The current owners enlisted Jeff Miller, one of Portland's most respected architects for historic and legacy homes, to thoughtfully expand and modernize the property. His addition feels like it has always been here, preserving the original charm and character while making the home work beautifully for the way we live today. Brought to life by Olson & Jones, known for their craftsmanship, the quality and attention to detail are evident throughout. A comprehensive renovation ties it together, creating a home that feels both timeless and current across 5,398 square feet. What truly makes this property special, beyond its undeniable charm, is the relationship between the house and the gardens. The landscape, originally designed by Craig Keist, isn't a backdrop, it's part of daily life here. Stone paths, layered gardens, and sweeping lawns wrap around the home, creating spaces to wander, gather, and enjoy. Windows frame greenery in every direction, and rooms open naturally to the outdoors. A striking oversized chess set anchors the front garden, while beyond, an open field offers room for a sport court, tennis, pickleball, or whatever comes next. Close in, but completely in its own lane, minutes from downtown, shops, freeways, and the airport, connected when you want to be and private when you don't. The next chapter is waiting.

5050 SW Hilltop Ln | MLS# 775449704

This single family home located at 5050 SW Hilltop Ln, Portland, OR 97221 is currently listed for sale with an asking price of $2,495,000. This property was built in 1940 and has 4 bedrooms and 3 full and 1 partial baths with 5398 sq. ft. Search Portland real estate on www.williamraven.realtor today.

Property Features

Property Type: Residential - Single Family
Basement: Crawl Space, Finished
Basement: Yes
Cooling: Central Air
Fireplaces: 3
Fuel Type: Electricity, Gas
Garage: 2 car attached
Heating: Forced Air, Mini Split
Home Style: Cottage, English
Lot Size: 1.59 Acres
Roof Type: Shake
Stories: 3.0
Taxes: $22,833
Year Built: 1940
Square Feet: 5,398

Feature Descriptions

Bathroom: 1.0 (Lower), 1.1 (Main), 1.0 (Upper)
Days on Site: 2
Exterior: Wood Siding
Exterior: Built-in Hot Tub, Garden, Patio, Raised Beds, Yard
Fireplace: Gas, Wood Burning
Hot Tub: Yes
Hot Water: Electricity, Tank
Interior: Hardwood Floors, Laundry, Marble, Tile Floor, Vaulted Ceiling(s)
Kitchen: Built-in Range, Dishwasher, Island, Marble, Pantry, Range Hood, SolidSurfaceCountertop, Stainless Steel Appliance(s), Wine Cooler
Lot: Level, Private, Secluded
Lot Dimensions: 69,300 Sq Ft Lot
Parking Notes: Attached, Driveway
Sewer: Public Sewer
Square Footage: 1894 (Lower), 2367 (Main), 917 (Upper)
Water: Public Water

Local Schools

High School: Lincoln
Middle School: West Sylvan
Elementary School: Bridlemile

Listed By / Shown By

Listed By

Agency Name: Where, Inc.
Agency Phone: 503-222-4373

Shown By

Agent Name: William Raven Broker
Agent Phone: (541) 280-9701
Agency Title: Bend Premier Real Estate

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Estimated Payment

$ 15,246.54 per month $12,616.08 Principal & Interest $1,902.75 Property Tax $727.71 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 06/01/2026. The listing information on this page last changed on 06/01/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Mon 06/01/2026 12:45:51 AM EST) or RMLS (last updated Sun 05/31/2026 1:50:20 AM EST) or COAR/MLSCO (last updated Mon 06/01/2026 12:41:17 AM EST). Real estate listings held by brokerage firms other than Bend Premier Real Estate may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

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 other brokerage firms are marked with the RMLS logo, and detailed information about these properties includes the names of the listing brokers. Listing content is copyright © 2026 RMLS, Portland, Oregon. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.

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