Heritage Listings

$3,950,000 (USD)
Active

Forest Hills Area Residential

Active

1561 Chandler Rd Lake Oswego, OR 97034

4 Bed
6 Baths
7154 sqft
MLS# 372387578
This Lake Oswego estate represents a level of quality, craftsmanship, and long-term stewardship that is hard to find. Privately situated on over half an acre near the Lake Oswego Country Club, the property combines substantial living spaces with thoughtfully designed grounds. Built and maintained to exacting standards, the home is distinguished not only by its finishes, but by the extensive investment made in the systems, infrastructure, and amenities incorporated into its construction. Thoughtfully designed for both daily living and entertaining, the home offers a main-level bedroom/ensuite, dedicated office, formal and informal living spaces, and five fireplaces integrated throughout the home. Upstairs, each bedroom features an ensuite bathroom, including a spacious primary suite with a covered balcony. A large bonus room finished with a kitchenette further enhances the home's functionality. The outdoor experience is equally compelling. The substantial, private grounds unfold through a series of inviting outdoor spaces connected by meandering pathways. Two outdoor kitchens, a saltwater spa, built-in fire pit, outdoor fireplace, and multiple gathering areas provide countless opportunities to host, relax, and enjoy the setting. Residents also enjoy access to the Forest Hills lake easement, providing access to Oswego Lake and the lifestyle that surrounds it. Years of thoughtful investment, meticulous maintenance, and a commitment to quality have created an offering that stands apart in today's market.
Listing Courtesy of RMLS / Listed By: Judy P. Adler, Windermere Heritage
$2,400,000 (USD)
Active

Willamette River Area Residential

Active

3838 SE Hillside Dr Milwaukie, OR 97267

5 Bed
6 Baths
9925 sqft
MLS# 552273879
Virtual Tour
Exceptional Modern Contemporary home set on a 1.25 private, gated acre along one of the Willamette River's most coveted stretches, this extraordinary custom estate delivers the Pacific Northwest lifestyle at its finest. One hundred sixty feet of prime river frontage with your own private boat dock. Putting you on the water instantly while providing easy access to the downtown Portland Waterfront with a short boat cruise up the river. Nearly 10,000 square feet of refined living unfolds across three levels. Exceptional craftsmanship features exquisite marble, granite finishes, beautiful woods and five fireplaces. Spectacular river and woodland views from every room create an atmosphere that is refined without ever feeling formal. The chef's kitchen is built to impress. The kitchen island provides multiple different cooking surfaces for every style of cooking, a truly modern and versatile appliance. Featuring high-end stainless-steel appliances and an abundance of built-in cabinetry making this kitchen a dream for family and entertaining. The main-level primary suite offers a serene retreat with immediate access to the outdoors on your own private balcony. Entertaining comes naturally here. A great room anchored by a full bar flows to a sweeping patio and stone terraces that overlook the water. Seamless indoor-outdoor living at its best. Private guest quarters with it’s own entrance adds exceptional flexibility, whether for multigenerational living, a long-term guest, or a live-in caretaker. Gated, private, and truly one of a kind.Conveniently located across from the Cedaroak Boat Ramp @ 4600 Elmran Dr. West Linn, OR.97068. SUNSET VIEWS!
Listing Courtesy of RMLS / Listed By: Jennifer King, Windermere Heritage
$1,498,000 (USD)
Active

Woodland Area Residential

Active

2838 Lewis River Rd Woodland, WA 98674

5 Bed
4 Baths
3132 sqft
MLS# 332845867
Virtual Tour
NEW PRICE!! Rare opportunity! One-owner property built and maintained by the original builder.2 homes and 2 ADUs, all set on 5.39 private acres in Woodland, Washington. The 3,132 sq ft main home offers 5 bedrooms, 3.5 baths, and a fully finished daylight basement ADU.The property has been extensively maintained, reflecting true pride of ownership, including a new roof on the main home (2024), new furnace and A/C (2025), full exterior paint on all structures (2025), and full interior paint on the main home (2026).In addition to the main residence, the property includes a separate 972 sq ft manufactured home with 2 bedrooms and 2 bathrooms, along with a detached garage and shop with a studio ADU. In total, four independent living spaces across two tax parcels—providing flexibility for multigenerational living, guest use, or income potential.The acreage offers a private, park-like setting with a year-round creek, a private pond rich with wildlife, established walking trails, mature landscaping, vintage roses, producing grapevines, and healthy raspberry bushes. With this level of natural amenity, care, and proximity to the city, opportunities like this are increasingly rare—and practically irreplaceable.The Lewis River area offers easy access to boating, camping, and hiking—an outdoor lover’s dream. The property is just 2 miles from Lewis River Golf Course, 7 miles from Lake Merwin, and 4.5 miles to Horseshoe Lake. Costco is approximately 12 miles away, ilani Casino 8.9 miles, and Vancouver just a short 25-minute drive.Potential for retreat or small-scale event or wedding use (buyer to verify).A versatile property that functions well as a primary residence, with added flexibility for those who want it. Reach out to schedule a private tour!Broker is related to seller.
Listing Courtesy of RMLS / Listed By: Michael Wright, Windermere Heritage
$1,468,800 (USD)
Pending

Portland Area Residential

Pending

2505 SW Hillcrest Dr Portland, OR 97201

3 Bed
4 Baths
4202 sqft
MLS# 780361866
In true Colonial Revival form, Hillcrest Dr stands proud in its timeless symmetry, centered six-pane front door, and rows of oversized windows accented by shutters designed to truly function. This little slice of heaven was designed by one of Portland's best known residential architects -Roscoe Hemenway. Tucked just below the winding street, the ‘secret garden home offers unparalleled privacy. The floorplan flows from one spacious entertaining area to another, yet the home still feels intimate. This is a home built for gathering. The stunning amount of natural light creates an airy energy, a must with Portland's tendency towards gloomy. While remaining true to the home’s original character, some of the significant improvements include updated electrical & plumbing, fully insulated, earthquake retrofitted, addition of an upper-level laundry, and beautifully redesigned bathrooms, each featuring heated floors. The main level is a natural stage for entertaining. A kitchen for people who love to cook includes a built-in eating nook that will be an instant favorite. The living and dining rooms are really quite beautiful. Sooo many floor to ceiling windows, each room with a fireplace. This space transitions seamlessly onto a covered patio —one of three outdoor living areas —and a lushly landscaped yard. The upper level has 3 ensuites, with the most breathtaking primary bedroom. This beauty features a wall of custom built-ins, a fireplace, walk-in closet (with a window!), and a spa-like bath, all opening onto a balcony with city views. Movie nights, games, kids and friends taking over the house -the lower level family room becomes the perfect hangout. A rare garage with an elevator for bringing down packages & groceries, plus additional parking for at least 5 cars along the property! And finally, a detached apartment —a hideaway for guests, a quiet workspace, or the ideal studio for passive income. A treasured home for family, friends, and gathering.
Listing Courtesy of RMLS / Listed By: Sonya Sperring, Windermere Heritage
$1,400,000 (USD)
Pending

Westridge Area Residential

Pending

2525 Bree Ct Lake Oswego, OR 97034

4 Bed
3 Baths
3707 sqft
MLS# 634563340
Virtual Tour
Tucked into a quiet Westridge cul-de-sac, this home strikes a balance that's hard to find with generous living spaces, rich design, and a floor plan that lives well. Hardwood floors, soaring ceilings, and abundant natural light create a sense of warmth, while the home's thoughtful layout offers both openness and separation where it matters most. Designed for both everyday living and entertaining, the heart of the home is a spacious great room that seamlessly connects to the breakfast nook and impressive kitchen. Maple cabinetry extends nearly to the ceiling, complemented by under and over-cabinet accent lighting, stainless steel appliances, double ovens, abundant storage, and an oversized island. A separate bonus room on the main level offers great flexibility. Upstairs, a generous primary suite offers an adjoining flex space ideal for a home office, nursery, or fitness room. The vaulted walk-in closet features custom organization and cedar-lined accents. Outdoor living is equally inviting, with a large paver patio, partial cover for year-round enjoyment, and a built-in firepit that creates another gathering space. Mature landscaping and the home's thoughtful positioning on the lot provide a remarkable sense of privacy. An exceptional opportunity to enjoy spacious living, privacy, and one of Lake Oswego's most sought-after neighborhood settings.
Listing Courtesy of RMLS / Listed By: Judy P. Adler, Windermere Heritage