Vintage homes for sale & real estate in Sylvan-Highlands, OR

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1325 SW Upland Dr, Portland, OR 97221
1325 SW Upland Dr, Portland, OR 97221
1325 SW Upland Dr, Portland, OR 97221
ABOUT THIS HOME
Vintage Home for sale in Sylvan-Highlands, OR:
One-of-a-Kind Home in Sought-After SW Hills Neighborhood!Tucked into a rare, quiet setting that offers both peace & proximity, this exceptional SW Hills home is truly one of a kind. Featured in Oregon Home and Inspired House magazines, it blends thoughtful design with versatile living space to suit a variety of lifestyles. A connected 650-square-foot guest quarters, with its own outside access, adds unmatched flexibility. With its own kitchen, bedroom, full bath, laundry, private entrance & deck access, this space is ideal as a separate mother-in-law suite, guest retreat, prep kitchen, or even private quarters for a caretaker or college student. The main home showcases a spaciou

$1,197,000

5 beds3.5 baths3,818 sq ft

1325 SW Upland Dr, Portland, OR 97221

0.45 acre lot • 2 garage spots • Car-dependent

Darcie VanderZanden • Keller Williams Sunset Corridor

3D WALKTHROUGH

1934 SW Highland Rd, Portland, OR 97221
1934 SW Highland Rd, Portland, OR 97221
1934 SW Highland Rd, Portland, OR 97221
ABOUT THIS HOME
Vintage Home for sale in Sylvan-Highlands, OR:
Experience refined luxury in the coveted Highlands neighborhood of unincorporated Multnomah County. Set on 1.26 acres near Forest Park trails, the Oregon Zoo, and The Racquet Club, this 1930 architectural gem blends timeless elegance with modern updates. Featuring formal living and dining rooms, 7 fireplaces, and a 700+ bottle wine cellar, it's ideal for both entertaining and everyday living. The beautifully landscaped outdoor space includes a covered portico, irrigated gardens, and manicured grounds—perfect for relaxing or hosting. Enjoy an oversized 3-car garage and extra cobblestone parking. Just minutes from downtown and top-rated schools, plus the tax savings of unincorporated Mu

$2,250,000

5 beds6.5 baths6,401 sq ft

1934 SW Highland Rd, Portland, OR 97221

1.26 acre lot • 3 garage spots • Car-dependent

Stacy Niedermeyer • Where, Inc

OPEN SAT, 12PM TO 1:30PM

1665 SW Highland Pkwy, Portland, OR 97221
1665 SW Highland Pkwy, Portland, OR 97221
1665 SW Highland Pkwy, Portland, OR 97221
ABOUT THIS HOME
Vintage Home for sale in Sylvan-Highlands, OR:
UNINCORPORATED MULTNOMAH TAX SAVINGS! Best Priced House per square foot!Nestled in the Sylvan Highlands neighborhood, this elegant and private Cape Cod home blends timeless charm with modern amenities. Featuring new windows, doors, insulation, and sheetrock, the home offers comfort and efficiency throughout. The gourmet kitchen is a true centerpiece, boasting soaring A-frame ceilings, soapstone countertops, custom cabinetry, a white oak island, red oak hardwood floors, and high-end stainless steel appliances, including a large farmhouse sink. The adjoining dining & formal living room retains its character with an original plaster ceiling and rounded corners. The main level includes a

$899,999

5 beds3.5 baths3,495 sq ft

1665 SW Highland Pkwy, Portland, OR 97221

0.25 acre lot • 2 garage spots • Car-dependent

Stacy Niedermeyer • Where, Inc

1535 SW 57th Ave, Portland, OR 97221
1535 SW 57th Ave, Portland, OR 97221
1535 SW 57th Ave, Portland, OR 97221
ABOUT THIS HOME
Vintage Home for sale in Sylvan-Highlands, OR:
HOUSE HAS ZERO VALUE. Do not try to walk on the property unless an appointment has been made. This fixer that is zoned RM1 (Residential Multi-Dwelling1) is situated on a half-acre corner lot in the popular Sylvan-Highland neighborhood. Located within a high-rated school district and close to St Vincent Hospital, Washington Park, etc. , there are plenty of development/investor opportunities for this preferred area. You'll love the easy access to Hwy 26 towards the high-tech corridor or take Skyline to the shops & restaurants on NW 23rd Ave. Rear section of property is RM1(p) - "Environmental Protection". Front section of property is RM1(s) "Scenic Resource".

$519,000

3 beds1 bath2,296 sq ft

1535 SW 57th Ave, Portland, OR 97221

0.5 acre lot • 2 garage spots • Car-dependent

Declan O'Connor • Cascade Hasson Sotheby's International Realty

VIDEO TOUR

906 SW Skyline Blvd, Portland, OR 97221
906 SW Skyline Blvd, Portland, OR 97221
906 SW Skyline Blvd, Portland, OR 97221
ABOUT THIS HOME
Vintage Home for sale in Sylvan-Highlands, OR:
Embrace the opportunity to create your dream home in the coveted Sylvan-Highlands neighborhood. This buildable lot is situated in a peaceful, wooded setting within a Single Family Residential Zone, allowing for the construction of a main home plus an ADU. Spanning approximately 19,166 square feet, the lot features a steeper slope and natural woodland, offering a serene and private environment. The Skyline area, located within the West Hills of Portland, offers a tranquil, low-density residential community characterized by lush greenery, quiet streets, and stunning views of the city and mountains. Residents enjoy easy access to outdoor recreation and scenic trails, making it ideal for outdoo

$175,000

— beds— baths— sq ft

906 SW Skyline Blvd, Portland, OR 97221

0.44 acre lot • Car-dependent

Ryann Reinhofer • Thoroughbred Real Estate Group Inc

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Vintage Homes for Sale in Sylvan-Highlands

There are currently 5 vintage homes for sale in Sylvan-Highlands at a median listing price of $800K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Sylvan-Highlands stay on the market for 67 days and receive 3 offers. Popular neighborhoods include Pearl District, Northwest Portland, North Portland, Corbett, and Southwest Portland. This map is refreshed with the newest listings in Sylvan-Highlands every 15 minutes.

In the past month, 4 homes have been sold in Sylvan-Highlands. In addition to houses in Sylvan-Highlands, there were also 5 condos, 1 townhouse, and 1 multi-family unit for sale in Sylvan-Highlands last month. Sylvan-Highlands is a not walkable neighborhood in Multnomah County with a Walk Score of 19. Sylvan-Highlands is home to approximately 1,290 people and 1,522 jobs. Find your dream home in Sylvan-Highlands using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Sylvan-Highlands are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Sylvan-Highlands. If you're looking to sell your home in the Sylvan-Highlands area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Sylvan-Highlands with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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All information provided is deemed reliable but is not guaranteed and should be independently verified. 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 brokerage firms other than Redfin are marked with the RMLS logo and detailed information about these properties includes the names of the listing brokers. Copyright © 2025 RMLS, Portland, Oregon. Data Last Updated Fri Jul 25 2025

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