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 windows framing the panoramic valley views, along with direct access to the deck. The luxurious en-suite bath includes a glass-enclosed shower with rainfall head and a soaking tub set behind antique Geisha doors—ideal for unwinding while taking in the tranquil scenery. The outdoor fire pit offers a cozy spot to relax with a drink after the sun sets, and the expansive lot includes a large, flat, unimproved area on the eastern side, providing exciting opportunities for future expansion or personalization. Espalier fruits include grapes, fig tree, & crab apple additional plantings include blueberries, blackberries, raspberries and plums! All this, conveniently located for an easy commute to downtown Portland, NW 23rd, Nike WHQ, and OHSU. This one-of-a-kind retreat blends timeless design, artisan details, and modern comfort in a truly exceptional setting. [Home Energy Score = 7. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10060376]
Active
$995,000
4416 SW Chesapeak Ave, Portland, OR 97239
4beds
2,568sqft
Est.:
Residential, Single Family Residence
Built in 1958
0.36 Acres Lot
$-- Zestimate®
$387/sqft
$-- HOA
What's special
Panoramic valley viewsSweeping unobstructed viewsDouble lotOutdoor fire pitExpansive view deckBespoke cabinetryGlass-enclosed shower
- 66 days
- on Zillow |
- 2,734 |
- 272 |
Zillow last checked: 7 hours ago
Listing updated: August 10, 2025 at 07:51pm
Listed by:
Steve Odermann sodermann@windermere.com,
Windermere Realty Trust,
Chris Barman 503-686-1952,
Windermere Realty Trust
Source: RMLS (OR),MLS#: 463560845

Travel times
Tour with a buyer's agent
Tour with a buyer's agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 3
- Full bathrooms: 2
- Partial bathrooms: 1
- Main level bathrooms: 2
Rooms
- Room types: Bedroom 4, Bedroom 2, Bedroom 3, Dining Room, Family Room, Kitchen, Living Room, Primary Bedroom
Primary bedroom
- Features: Ceiling Fan, Hardwood Floors, Sliding Doors, Closet, Ensuite, Soaking Tub, Walkin Closet, Walkin Shower
- Level: Main
- Area: 204
- Dimensions: 17 x 12
Bedroom 2
- Features: Closet, Vinyl Floor
- Level: Lower
- Area: 168
- Dimensions: 14 x 12
Bedroom 3
- Features: Beamed Ceilings, Builtin Features
- Level: Lower
- Area: 121
- Dimensions: 11 x 11
Bedroom 4
- Features: Beamed Ceilings
- Level: Lower
Dining room
- Features: Hardwood Floors
- Level: Main
- Area: 143
- Dimensions: 13 x 11
Family room
- Features: Builtin Features, Fireplace, Hardwood Floors, Sliding Doors
- Level: Main
- Area: 130
- Dimensions: 13 x 10
Kitchen
- Features: Appliance Garage, Dishwasher, Gas Appliances, Island, Pantry, Free Standing Range, Free Standing Refrigerator
- Level: Main
- Area: 195
- Width: 13
Living room
- Features: Fireplace, Sliding Doors, Wood Floors
- Level: Main
- Area: 240
- Dimensions: 20 x 12
Heating
- Forced Air, Fireplace(s)
Cooling
- Central Air
Appliances
- Included: Appliance Garage, Dishwasher, Disposal, Free-Standing Gas Range, Free-Standing Refrigerator, Stainless Steel Appliance(s), Washer/Dryer, Gas Appliances, Free-Standing Range, Gas Water Heater
- Laundry: Laundry Room
Features
- Ceiling Fan(s), Quartz, Beamed Ceilings, Closet, Built-in Features, Kitchen Island, Pantry, Soaking Tub, Walk-In Closet(s), Walkin Shower
- Flooring: Hardwood, Heated Tile, Vinyl, Wood
- Doors: Sliding Doors
- Windows: Double Pane Windows, Wood Frames
- Basement: Daylight,Finished
- Fireplace features: Gas, Wood Burning
Interior area
- Total structure area: 2,568
- Total interior livable area: 2,568 sqft
Video & virtual tour
Property
Parking
- Total spaces: 1
- Parking features: Carport, Driveway, Garage Door Opener, Attached, Converted Garage
- Attached garage spaces: 1
- Has carport: Yes
- Has uncovered spaces: Yes
Accessibility
- Accessibility features: Main Floor Bedroom Bath, Walkin Shower, Accessibility
Features
- Stories: 2
- Patio & porch: Deck, Patio
- Exterior features: Fire Pit, Garden, Water Feature
- Has view: Yes
- View description: Mountain(s), Territorial, Valley
Lot
- Size: 0.36 Acres
- Features: Private, Sloped, Terraced, SqFt 15000 to 19999
Details
- Parcel number: R141868
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Custom Style,Daylight Ranch
- Property subtype: Residential, Single Family Residence
Materials
- Brick, Wood Siding
- Foundation: Slab
- Roof: Metal
Condition
- Updated/Remodeled
- New construction: No
- Year built: 1958
Utilities & green energy
- Gas: Gas
- Sewer: Public Sewer
- Water: Public
Community & HOA
Community
- Security: Security Lights
HOA
- Has HOA: No
Location
- Region: Portland
Financial & listing details
- Price per square foot: $387/sqft
- Tax assessed value: $881,790
- Annual tax amount: $12,387
- Date on market: 6/6/2025
- Listing terms: Cash,Conventional
- Road surface type: Paved
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