Vintage homes for sale & real estate in Overlook, OR

Vintage Home for sale in Overlook, OR:

This beautifully updated 1915 Piedmont bungalow has charm to spare, with four spacious bedrooms and two full baths spread across three light-filled levels. Plus, a versatile bonus room for a gym or creative space and a relaxing sauna! High ceilings, hardwood floors, and original details set the tone, from the built-in dining buffet to the ornamental living room fireplace. The updated kitchen shines with new stainless appliances and generous counter space. Outside, a beautifully landscaped, fenced backyard offers a patio and raised garden beds for your green thumb. Major upgrades include mini split heating and cooling, a backup gas furnace, and electrical service with a 200 amp panel plus 10

Vintage Home for sale in Overlook, OR:

Opportunity knocks with this three-story Craftsman ready for its next chapter! This 3-bedroom, 1.5-bath home is a true fixer with the character, footprint, and potential to be brought back to life. The unfinished basement provides additional space and possibilities, while the massive 4-car garage is a standout feature—ideal for vehicles, a workshop, storage, or hobby space. For investors and developers, the property’s zoning may offer additional development potential; buyer to perform their own due diligence and verify all allowable uses with the appropriate governing agencies. Whether you’re looking for a substantial renovation project, investment opportunity, or a proper

Vintage Home for sale in Overlook, OR:

Classic Tudor charm meets a fresh 2026 update on the quieter stretch of N Mississippi Avenue, just one block from Peninsula Park and its beautiful rose gardens! Inside, original character still takes center stage, with refinished hardwood floors, rich wood trim, period built-ins, and a classic wood-burning fireplace. The inviting living room flows into the formal dining room and refreshed kitchen, where new cabinetry, countertops, flooring, and sink pair with a vaulted ceiling and skylight for an unexpected sense of light and space. The main level offers two comfortable bedrooms overlooking the backyard and a full bathroom. Upstairs, the expansive primary suite creates a private retreat wit

Vintage Home for sale in Overlook, OR:

Welcome to 545 N Baldwin St, the jewel of the Lovewood Addition in Piedmont. Built in 1938, this home has fresh exterior paint that makes it sparkle as soon as you pull in the driveway. Up the brick-trimmed front steps, you're drawn in through the entry and greeted immediately by the gas fireplace, the focal point of the light-filled living room. Through the dining space and updated kitchen, you'll find two main floor bedrooms and a full bathroom. The basement is fully finished with fresh paint and carpet, a second full bathroom, third bedroom and large flex space for working days, cozy nights and everything in between. And, with an additional entrance in back, the basement may have rental

Vintage Home for sale in Overlook, OR:

Set up high above the street, this Vintage Piedmont Cottage is ready for its next chapter. Estate owned with all the 1941 charm intact. Original beaded wood siding and scalloped trim. Wood floors, arched doorways and tray ceilings. Spacious rooms and a terrific floor plan. Definitely needs some love but there is so much potential here. 2 main floor bedrooms plus potential bonus space/bedrooms up and down (currently non-conforming). Quiet corner lot, big yard, new fence. Tuck under garage. This property has been fully inspected and reports are available. Priced for an as-is sale. [Home Energy Score = 2. HES Report at https://rpt. greenbuildingregistry.com/hes/OR10250839]

Vintage Home for sale in Overlook, OR:

Fixer alert! This one has some serious potential with the demo done and ready to put back together. Upside in adding a bathroom and bedrooms in basement. Seller can Carry the note while you fix up! Lot also has approved plans for a 21 unit apartment for the infill developer. Huge shop with alley access, this one is a must see,