4416 SW CHESAPEAK AVE

Portland, 97239

  • 4 Bed

  • 2.5 Bath

  • 2568 SqFt

  • 127 DOM

  • Built: 1958

  • Status: Active

$995,000

Price cut: $5 (10-10-2025)

X

4416 SW CHESAPEAK AVE

Portland 97239

$995000

Price cut: $5 (10-10-2025)

  • 4 Bed

  • 2.5 Bath

  • 2568 SqFt

  • 127 DOM

  • Built: 1958

  • Status: Active

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Krishna Regupathy

Principal Broker

(503) 893-8874

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]

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Residence Information

  • 0

  • 1593

  • 975

  • 2568

  • RMLS

  • 1593

  • 4

  • 2

  • 1

  • 2.5

  • Metal

  • 1, Attached, Carport, Converted

  • CustomStyle,DaylightRanch

  • Carport,Driveway

  • 2

  • 1958

  • Yes

  • Brick, WoodSiding

  • Daylight,Finished

  • Daylight,Finished

  • Slab

  • DoublePaneWindows,Wo

Features and Utilities

  • Fireplace, SlidingDoors

  • ApplianceGarage, Dishwasher, Disposal, FreeStandingGasRange, FreeStandingRefrigerator, Island, Quartz, Stai

  • CeilingFan, GarageDoorOpener, HardwoodFloors, HeatedTileFloor, Laundry, MurphyBed, Quartz, VinylFloor, Washe

  • Deck, FirePit, Garden, Patio, WaterFeature

  • MainFloorBedroomBath, WalkinShower

  • CentralAir

  • Gas

  • ForcedAir

  • PublicSewer

  • Gas

  • Gas

Financial

  • 12387.67

  • 0

  • Cash,Conventional

  • 06-06-2025

  • No

  • No

Comparable Information

  • 127

  • 128

  • Cash,Conventional

  • $995,000

  • $995,000

  • Oct 10, 2025 17:31

Schools

Elementary : Rieke N/A Ratings
Middle : Robert Gray N/A Ratings
High : Ida B Wells N/A Ratings

Map

Listing courtesy of Windermere Realty Trust.

The content relating to real estate for sale on this site comes in part from the IDX program of the RMLS of Portland, Oregon. Real Estate listings held by brokerage firms other than this firm are marked with the RMLS logo, and detailed information about these properties include the name of the listing's broker. Listing content is copyright © 2019 RMLS of Portland, Oregon. All information provided is deemed reliable but is not guaranteed and should be independently verified. Krishna Realty data last checked: Oct 12, 2025 18:02 | Listing last modified Oct 10, 2025 17:31. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.

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