4416 SW CHESAPEAK AVE

Portland, 97239

  • 3 Bed

  • 2.5 Bath

  • 2651 SqFt

  • 1 DOM

  • Built: 1958

  • Status: Active

$959,000

X

4416 SW CHESAPEAK AVE

Portland 97239

$959000

  • 3 Bed

  • 2.5 Bath

  • 2651 SqFt

  • 1 DOM

  • Built: 1958

  • Status: Active

Love this home?

Request Tour, Ask a Question or Start an Offer

Krishna Regupathy

Principal Broker

(503) 893-8874

Perched atop a rare double lot, this artfully reimagined Mid-Century daylight ranch commands sweeping, unobstructed vistas spanning from the Coast Range to the eastern foothills. Thoughtfully sited & masterfully landscaped to preserve both privacy & tranquility, the property is designed to minimize neighboring sight lines—creating a serene sanctuary where the expansive view deck & natural surroundings can be enjoyed in complete seclusion. Inside, the bespoke kitchen serves as the heart of the home—a true statement in both form and function—appointed with stainless steel appliances, custom cabinetry & an oversized entertainer’s island designed to host gatherings both intimate & grand. The primary suite is a retreat unto itself, introduced through early 20th-century antique Japanese doors & enveloped by floor-to-ceiling glass that frames the ever-changing panorama beyond. With direct access to the deck, the suite seamlessly blends indoor & outdoor living. The spa-inspired bath offers a glass-enclosed rainfall shower & a soaking tub set behind antique Geisha doors—an evocative, tranquil setting for relaxation. Outdoors, a sculpted landscape unfolds with intention. A fire pit beneath the open sky invites evenings of quiet reflection, while curated plantings—including espaliered grapes, fig, crab apple, along with blueberries, blackberries, raspberries & plums—create a living garden that is as functional as it is beautiful. A substantial, level unimproved area on the eastern portion of the lot presents a rare opportunity for future expansion or a bespoke addition. All of this, just moments from downtown Portland, NW 23rd, Nike World Headquarters & OHSU. A truly singular offering—where timeless mid-century design, artisan craftsmanship & modern livability converge in an extraordinary setting. [Home Energy Score = 7. HES Report at https://rpt.greenbuildingregistry.com/hes/OR10060376]

Download our Mobile app

Residence Information

  • 0

  • 1535

  • 1116

  • 2651

  • Floor Plan

  • 1535

  • 1/Gas

  • 3

  • 2

  • 1

  • 2.5

  • Metal

  • 1, Attached, Carport, Converted

  • CustomStyle,DaylightRanch

  • Carport,Driveway

  • 2

  • 1958

  • Yes

  • Brick, WoodSiding

  • Daylight,ExteriorEntry,Finished

  • Daylight,ExteriorEnt

  • Slab

  • DoublePaneWindows,Wo

Features and Utilities

  • Fireplace

  • Dishwasher, Disposal, FreeStandingRange, FreeStandingRefrigerator, Island, Microwave, Quartz, StainlessStee

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

  • Deck, FirePit, Garden, Patio, WaterFeature, Yard

  • MainFloorBedroomBath, NaturalLighting, WalkinShower

  • CentralAir

  • Gas

  • ForcedAir

  • PublicSewer

  • Gas

  • Gas

Financial

  • 12849.68

  • 0

  • Cash,Conventional

  • 03-27-2026

  • No

  • No

Comparable Information

  • 1

  • 1

  • Cash,Conventional

  • $959,000

  • $959,000

  • Mar 27, 2026 15:15

Schools

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

Map

Listing courtesy of LUXE Forbes Global Properties.

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: Mar 28, 2026 02:14 | Listing last modified Mar 27, 2026 15:15. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.

Similar Properties

Download our Mobile app

Open Sat, Mar 28th, 10AM to 12PM

$2,299,900

  • 3 Bed

  • 3 Bath

  • 2584 SqFt

  • 1 DOM

  • 1209 SW HESSLER DR, Portland, 97239
Open Fri, Mar 27th, 6PM to 8PM

$1,190,000

  • 4 Bed

  • 3 Bath

  • 3540 SqFt

  • 3 DOM

  • 1663 SW WESTWOOD DR, Portland, 97239

$825,000

  • 4 Bed

  • 3 Bath

  • 2213 SqFt

  • 3 DOM

  • 3125 SW DOSCHDALE DR, Portland, 97239

$1,025,000

  • 3 Bed

  • 3.5 Bath

  • 2816 SqFt

  • 9 DOM

  • 6515 S CORBETT AVE, Portland, 97239

Login to continue

Email field required!
Password field required!
Show password

Forgot your password?

Reset your password?

You will receive a link to the entered email address to create a new password

Error message here!

Back to login

Sign up with Email