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$1,190,000
3 Beds 2 Baths 532087603 MLS
Beautiful custom chalet surrounded by acres of lush, living forest in the heart of Sherwood wine country.Filled with warmth, character, and one-of-a-kind details. Soaring ceilings, generous living spaces, custom tile fireplaces, hand-painted ceramic sinks, and designer wallpaper accents reflect the thought and craftsmanship found throughout the home.Three levels of living space include two primary suites, one with its own private entrance—ideal for multi-generational living or guests. An indoor jetted pool offers year-round enjoyment, while the open floor plan balances expansive gathering spaces with quieter, more intimate rooms.Mature trees, ferns, and abundant greenery surround the home, giving the property a remarkable sense of life and a feeling of being nested within the forest. Large windows draw that landscape indoors, keeping the changing light, trees, and natural surroundings present throughout the home.Lovingly cared for by its original owner and topped with a new roof, the home sits among the rolling hills and vineyards of Oregon wine country—a distinctive Craftsman where thoughtful architecture and the lush Willamette Valley landscape feel naturally intertwined. Top of driveway with water and electricity for shed or carport. No sign on road. GPS leads to right of driveway access.

22560 SW CHAPMAN RD, Sherwood

$950,000
4 Beds 3 Baths 326528491 MLS
Your Private Retreat - Without Sacrificing a Thing. Tucked away on a serene stretch of SW Rein Road, this 4-bedroom Sherwood gem delivers the rare combination every buyer is searching for: sweeping open-concept living, genuine privacy, and the kind of bones that invite you to make it entirely your own.Step inside and feel the space open up before you. The expansive, light-filled floor plan flows effortlessly from living to dining to kitchen — ideal for everyday family life and equally made for entertaining. Whether you're hosting a holiday gathering or a casual weekend get-together, there's room for everyone and every occasion.Four bedrooms provide the flexibility modern families demand, while generous family and flex spaces give you options most homes simply can't offer — a home office, a playroom, a media room, a gym. This is a property that grows with you.And the canvas? It's ready. With meaningful room to upgrade, customize, and personalize throughout, you can move in on your own terms and build value your way — at your own pace, to your own taste.Step outside and breathe. Surrounded by natural beauty and shielded from the noise of the world, the privacy here is palpable. Yet you're just minutes from Sherwood's charming downtown, top-rated schools, shopping, dining, and easy freeway access — close enough to everything, far enough from everyone.Peace, potential, and plenty of space. This is the one.

25800 SW REIN RD, Sherwood

$1,200,000
3 Beds 2 Baths 725504472 MLS
A rare opportunity to own a distinctive contemporary home designed by renowned Oregon architect William Fletcher, an influential figure in NW Modernism. Set on 7 private acres just minutes from downtown Sherwood, this special property was thoughtfully designed to connect architecture with its natural surroundings. Vaulted ceilings, an open floor plan and expansive windows fill the home with natural light while framing peaceful views of the pond, sunny pasture and surrounding landscape. Renovated with new cabinetry, quartz countertops, flooring, carpet and lighting, the home feels fresh and current while preserving the architectural character that makes it truly one of a kind. Flexible living spaces include a sunroom, bonus room and loft/studio. Outside, the lifestyle is just as special. Fruit trees, a bass-stocked pond, open pasture, a small barn + shop & 4 car garage. Irrigation water rights add to the property's versatility, with potential for gardens, hobby farming or vineyard. Private and peaceful, yet only 5–10 minutes from downtown Sherwood, shopping and dining, this is more than a home on acreage. It is an opportunity to live surrounded by nature in a piece of Oregon architectural history.

23340 SW KRUGER RD, Sherwood

$1,350,000
4 Beds 3 Baths 448573366 MLS
Rare Sherwood acreage, minutes from downtown yet worlds away. This 3,606 square foot home sits on 10 serene acres with 350 feet of frontage along Mill Creek, offering privacy, usable land, and true multigenerational flexibility. A freshly rejuvenated driveway winds through the trees to a beautifully rebuilt Trex entry. Inside, the main level lives large with granite counters, a marble backsplash, Miele coffee system, and Jenn-Air induction cooktop in the kitchen, plus a living room warmed by a brick-surround fireplace beneath skylights and picture windows. The primary suite is right on the main level, freshened with new carpet, paint, skylight, and a tile shower. Refreshed hardwood flooring runs throughout the main living areas. Upstairs, two bedrooms with walk-in closets share a large flex space and a stylish hall bath. Downstairs, a fully reimagined lower level adds a 4th bedroom, full bath, family room, bonus area, climate-controlled wine room, wet bar, wood stove, and walk-out slider, ideal for extended family, guests, or a multigenerational living space. Thoughtful, curated updates run throughout with the same care and meaningful investment extending well beyond the walls. Outside, the property earns its "endless possibility" reputation: pastureland once home to 16 sheep, a 2,000 SF shop area dug out with wiring and utility trench already in place, lawn, raised garden beds, and private trails crossing the creek on newly built bridges. A deep garage, RV parking, and abundant storage rounds out the setup. The expansive composite deck and hot tub make for quiet mornings and starlit evenings, with the creek, wind, and birdsong as the only soundtrack. All this within three miles to downtown Sherwood and Wilsonville, top-rated schools, and wine country. Ten acres. Room to breathe, room to build, room for everyone.

14821 SW BELL RD, Sherwood

$4,875,000
5 Beds 4 Baths 454208580 MLS
Five Peaks Farm — an exquisitely crafted custom Georgian estate sited on 31.79 pristine acres with sweeping 280° vistas of five mountain peaks and glittering city lights. The 8,028sqft residence greets you with a gracious foyer and offers timeless elegance throughout: a main level primary en suite, an impressive office, grand living room, formal dining and kitchen with butler’s station — all opening via walls of windows to multiple patios that capture the territorial panoramas. Interior appointments include rich hardwood floors, vaulted ceilings, wainscoting, six fireplaces, a library/study with a southern style balcony, dedicated theatre, exercise suite with steam and sauna, and high tech security systems. Dual staircases rise to the upstairs wings at either end of the home, while a separate staircase descends to the lower level entertainment spaces featuring a theatre, game room, kitchenette, gym, workshop and abundant storage. Exquisite brickwork and master craftsmanship complete the residence. Outdoors is resort caliber living and entertaining: expansive terraces, a pool with pool house and Island Spa hot tub, in ground trampoline, sand volleyball and tennis courts, plus monkey bars and swing play features—perfect for events, family gatherings and friend filled weekends across the vast, maturely landscaped grounds. Equestrian facilities are exceptional: an oversized Kentucky style barn with grain and tack rooms, storage and four stalls with covered runs, multiple large fenced and cross fenced turnouts, and direct access to on site riding trails. Practical amenities include an oversized detached garage with pull through doors, extensive operational space and the property’s current farm deferral status. Tucked privately off the road yet conveniently located in the top rated Sherwood school district with easy access to Sherwood, Wilsonville, Newberg and the I 5/I 205 corridors, Five Peaks Farm blends privacy, panoramic beauty, top tier infrastructure and lifestyle.

14161 SW TOOZE RD, Sherwood

$1,995,000
5 Beds 3 Baths 438858500 MLS
Back on the market through no fault of the home! A clean inspection report is available upon request. Sitting on nearly two private acres with direct access to surrounding forested trails, this exceptional estate offers a rare blend of scale, privacy, and elevated Northwest living. A circular drive creates a grand arrival, leading into soaring 14-foot ceilings, walls of windows, and a dramatic floor-to-ceiling stone fireplace that anchor the main living spaces with both warmth and presence. The chef’s kitchen is fully equipped with Sub-Zero and Wolf appliances, double ovens, prep sink, walk-in pantry, and an oversized eat bar, designed for both everyday living and effortless entertaining. A main-level bedroom with en suite provides flexibility, while the upper-level primary suite is a true showpiece, featuring a private balcony, double-sided fireplace, and a striking, spa-level bath with a jetted soaking tub designed for two and a triple-head shower, along with an expansive walk-in closet. The lower level offers additional living space with a separate entrance, generous storage, and ideal potential for a wine cellar or expanded suite with room to convert the existing half bath to a full. Outdoor living is exceptional, featuring a massive patio with a dramatic stone fireplace, built-in kitchen, dedicated garden with raised beds, beautifully landscaped yard, and storage shed. A full-house Generac generator, smart home features, central vac, custom built-ins, and a striking entry with water feature complete this one-of-a-kind offering.

18421 SW SALMONBERRY DR, Sherwood

$1,800,000
4 Beds 3 Baths 517969183 MLS
Exceptional ~36.5 acre equestrian property in a prime location, currently operating as a horse boarding facility with extensive equestrian amenities already in place. The impressive barn features a new roof and 8 total stalls, including 6 walk-out paddock stalls and 2 indoor stalls convertible to a foaling stall. Additional amenities include a horse wash station, tack-up area, and a tack room featuring a half bath and convenient sink and refrigerator area.Train year-round in the oversized 72’ x 198’ indoor dressage arena, complemented by a new 20-meter round pen. The property also includes a hay & shavings barn, additional 2 stall barn, large workshop, storage shed, and a 3-car carport. Fenced and cross-fenced with areas of newer fencing, plus ample turnarounds for trailers, this setup is ideal for boarding, training, or private use.The land itself is equally special, spanning approximately 36.48 acres and offering a pond, creek, and expansive open acreage with flexibility for future agricultural use, pasture, or personal farming, creating a peaceful and functional farm setting. The property consists of two tax lots and is conveniently located with an easy drive to Sherwood, Wilsonville, or Newberg, along with great nearby school options.The 3,324 sqft 4-bedroom, 3-bath home features a full basement providing additional living space, extra bedrooms, a sauna, and flexible use options. The finished basement is mid-remodel, with new lighting already installed and ready for your finishing touches. New heat pump installed in 2023. Upstairs, enjoy newer stainless steel appliances, granite countertops, laminate flooring, and a converted garage for extra living space.A rare opportunity to own a well-appointed equestrian property in a highly desirable location. More photos, property video, and 3D Tour available; visit the Virtual Tours.

29971 SW LADD HILL RD, Sherwood

$675,000
24290707 MLS
Prime Farmland with Established Hazelnut Orchard – 19.97 Acres Total. Opportunity awaits with this income-producing farm featuring two parcels. These properties are near the urban growth boundary making them an excellent choice for both immediate income and long-term growth possibilities. Property Highlights: Parcel 1 is 7 acres of fertile farmland with mature hazelnut trees. Parcel 2 is: 12.97 acres, also planted with established hazelnut trees. Current development opportunities could be Agricultural building, Equestrian Facilities, arena, stabling or training equines including but not limited to providing riding lessons, training clinics and schooling shows. Buyer to perform due diligence on zoning and the possibility of splitting lots or other development opportunities. These parcels offer a serene rural setting while offering easy access to urban amenities. Additional Information: Lot map available upon request. Contact listing agent for more details.

Bell and Baker RD, Sherwood

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