Sherwood, OR Real Estate Search

Sherwood, OR Historical Homes for Sale

Sherwood, Oregon, is home to a variety of charming historical homes that capture the essence of the area's rich heritage. Nestled in a picturesque setting, these properties range from the classic Victorian styles to quaint Craftsman bungalows, each telling its own unique story through architectural details and period features. Many historical homes in Sherwood have been lovingly restored, marrying modern amenities with vintage charm, making them appealing to both history enthusiasts and modern buyers alike. The allure of the past combined with the growing community and easy access to local amenities makes Sherwood an attractive location for those looking to invest in real estate with character and history.

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Newest Sherwood, OR Historical Homes for Sale

$777,950
5 Beds 3 Baths 427464864 MLS
Welcome to a beautiful, shows like new, 5 bedroom, plus den and upstairs bonus room tucked into one of Sherwood’s most desirable neighborhoods. With its inviting curb appeal, thoughtful updates, and spacious floor plan, this residence offers the perfect blend of comfort and style. Step inside to find light-filled living spaces with soaring ceilings, warm finishes, and an open layout ideal for entertaining. The gourmet kitchen features modern SS appliances, ample counter space, quartz counters, walk-in pantry and a convenient island eating bar. A catch-all mud bench off the garage keeps everything tidy. The pocket office with built in desk is a surprising addition - but packs a punch for a homework center or secondary office! A cozy family room with a fireplace creates the perfect place to relax. Laminate floors throughout the main. Upstairs, the primary suite is a true retreat with a walk-in closet and spa-inspired ensuite, with double sinks, tiled shower and deep soaking tub. Additional bedrooms are generously sized, offering plenty of flexibility for guests, a home office, or hobbies. The loft is a favorite space for a secondary family room or teen hang out. Main floor full bedroom and bath offers guest room, multigenerational options or spacious private home office. Out back, enjoy a private yard with mature landscaping—perfect for summer gatherings, gardening, or simply unwinding. The backyard is certified Backyard Habitat landscaping and is on a Hydra wise professional watering system. Custom, motorized awning covers the patio. Lovely views of Parrot Mtn from your backyard/patio/dining and family room. Located minutes from Sherwood’s award-winning schools, charming Old Town and wine country, this home provides both tranquility and convenience.

17412 SW TRILLIUM LN, 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

$2,250,000
6 Beds 4 Baths 288377015 MLS
Close-in country estate, Sherwood School District, 6 bedrooms, primary bedroom on the main, 6 car garage, motorcourt, RV parking, detached guest house, and VIEW! And it's not too good to be true! This stunning setting in Sherwood Oregon's sought after wine country offers a perfect blend of luxury and natural beauty. Embellished in stone, natural tile, and warm wood accents, this architectural masterpiece boasts a magnificent floor plan designed to live well and entertain in style! Imagine tranquil moments on the back deck or front porch, surrounded by sky-reaching trees... warming up by the wind-sheltered fire-pit where the concrete radiates warmth while you take in the natural views all around you. It's incredible here! The property's top-quality architecture and finishes are evident throughout from the gourmet kitchen adorned with stone and tile accents, to the rich cabinetry and built-ins. The kitchen and dining room flow into the spacious living room with floor to ceiling fireplace and walls of windows that frame the views. You'll also find the primary bedroom on the main, and downstairs, a spacious family/bonus room providing additional space for relaxation, activities watching movies, hosting, and endless possibilities. The estate's expansive outdoor spaces are a testament to its thoughtful design, offering so much room for enjoyment and the captivating presence of nature and wildlife, including the serene ambiance and sound of trickling water from the nearby creek.The expansive driveway affords plenty of parking and play space, and the property's clever positioning lends to its grand appeal, offering the essence of endless nature, with less maintenance required. A detached garage with separate living quarters above rounds out the estate. The carriage house provides versatile options for guests or additional living space. *Square Footage, bedroom and bath quantified for main house and ADU reflecting total living space. A complete list of updates is on file.

17725 NE LEANDER DR, 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

$2,295,000
7 Beds 5 Baths 584723010 MLS
This Parrett Mountain custom home is a masterclass in design and craftsmanship. The home commands attention not only for its scale, but for the intentionality and artistry woven throughout. When you enter the home, a dramatic wall of glass frames a sweeping five-mountain view, flooding the interiors with natural light and creating a seamless connection to the surrounding landscape. Crowning the home, a glass turret observatory offers a breathtaking vantage point for stargazing. The main level is anchored by a stunning great room with soaring ceilings, spacious gourmet kitchen and a serene, primary suite all designed for an elevated daily experience. From the main level, a sculptural handcrafted staircase leads to a skybridge, connecting two private rooms hidden behind custom bookcases. The lower level of the home provides exceptional versatility, featuring a second full kitchen, 2 additional bedrooms, bonus laundry room, a theater room and outdoor access. This is an ideal layout for multigenerational living or private guest quarters. Set up for entertainment, the home includes a private theater, expansive arcade, dance hall, sunroom and greenhouse. Outdoors, the grounds are meticulously maintained with beautiful hardscaping, a fully equipped outdoor kitchen, a custom waterfall hot tub and mature landscaping. In addition to an oversized three-car attached garage, there is a 30' x 74' shop with a full-size RV bay and a 580 sq ft, heated shop with ½ bath. Electric - 400 amp service to home; separate 200 amp meter/service to shop. Home is also equipped with a 15kw Generator. The main home has comfortable heated flooring throughout, a whole house sounds system, a smart system and is pre-wired for an automatic entry gate. This is a true luxury estate in one of the region’s most coveted neighborhoods with convenient access to Sherwood, Wilsonville, Newberg and Portland.

16700 SW PARRETT MOUNTAIN RD, Sherwood

$724,900
4 Beds 4 Baths 156457775 MLS
Nestled beneath a canopy of mature trees on 4.33 serene acres in Sherwood, Oregon. This ideal tri-level home built in 1972 offers the perfect setting for multi-family living. New roof, septic tank, skylights, and interior paint. The spacious layout includes four bedrooms and four full bathrooms. The main floor features a warm and inviting living room, a centrally located kitchen with hardwood floors and stainless steel appliances, a dedicated dining area, and a versatile multi-use room that can easily serve as a fifth bedroom. A full bathroom and convenient utility room are located on the main level. Upstairs, you'll find two primary suites each with their own bathroom, and an additional generously sized bedroom. The lower level is perfectly suited for extended living or guest quarters, offering a second full kitchen, a bedroom, and a bathroom with both interior and private exterior access. Thoughtfully designed home with an additional 512 sqft storage room that could be used in various ways. Step outside to enjoy peaceful, private views from the expansive wraparound deck, with the year round Chicken Creek flowing through the rear of the property. Fresh interior paint. Only 1.5 miles from the high school and a little over 2 miles from Ridges Elementary. Embrace country living with all the conveniences of nearby shopping, dining, and entertainment. Schedule your private showing today and experience the unique charm and versatility of this exceptional home.

22665 SW SCHALTENBRAND LN, Sherwood

$1,649,000
3 Beds 2 Baths 726255712 MLS
Experience the ultimate in rural living at this stunning custom estate, perfectly positioned on 5 completely usable acres. This home blends refined country living with timeless craftsmanship, featuring a gourmet kitchen with granite countertops, a copper sink, hardwood floors, and premium woodwork throughout. Enjoy three fireplaces, formal living and dining rooms, and a dramatic two-story family room that anchors the home with warmth and grandeur.From the dual staircase, you’ll find a serene primary suite with its own cozy fireplace, separate closets, and a spacious bathroom with a jetted soaking tub, picture window and spa vibes. Two additional bedrooms share a dual-sink bathroom, and a generous bonus room offers flexible space for work, play, or relaxation. Nearly every room captures a picturesque view, creating a sense of calm and connection to the land.Unwind on the wrap-around porch as the sun sets, stay comfortable year-round with AC, and appreciate the paved circular driveway and oversized three-car garage with high ceilings and abundant natural light. For added peace of mind, the home is equipped with a whole-home sprinkler system.Bring your animals home to the 24x32 barn, complete with space to customize two stalls—ideal for horses or hobby farming. The large pastures are cross-fenced with durable vinyl fencing, offering both beauty and functionality.A rare opportunity to embrace rural elegance without compromise.

21550 SW MOUNTAIN HOME RD, Sherwood

$599,000
4 Beds 2 Baths 539855128 MLS
Tucked away at the end of a quiet cul-de-sac on a private lot, this beautifully refreshed 4-bedroom Sherwood home with a spacious bonus room offers the perfect balance of comfort, functionality, and inviting living spaces.Step inside to bright, welcoming interiors designed for both everyday living and gathering with friends and family. The main level features a spacious great room along with a cozy living room centered around a warm fireplace—an ideal place to unwind on cooler evenings. The living room opens to an expansive deck overlooking the private backyard, creating a wonderful space for summer BBQs, entertaining guests, or enjoying a peaceful morning coffee.The kitchen has been refreshed with brand-new stainless steel appliances and offers generous space to cook, prep, and connect. Just off the kitchen, a comfortable eating area and breakfast bar provide the perfect spot for casual meals or conversation while cooking.Upstairs, the primary suite feels like a relaxing retreat with beautiful vaulted ceilings that create an open, airy feel. The suite includes a private bathroom and a spacious walk-in closet. Three additional bedrooms offer flexibility for family, guests, a home office, or creative space.A standout feature of the home is the large vaulted bonus room, providing endless possibilities—whether used as a media room, playroom, home gym, office, or hobby space.Recent 2026 updates include fresh interior paint, new luxury vinyl plank flooring, brand-new carpet throughout, and recently serviced major systems, making this home truly move-in ready.Located near parks, schools, and the charm of Old Town Sherwood, you’ll enjoy easy access to Snyder Park, local restaurants, shopping, and community events while remaining just a short drive to Bridgeport Village and major commuter routes into Portland.

22436 SW MEISSINGER PL, Sherwood

$699,000
3 Beds 2 Baths 647918091 MLS
Charming, artistic design meets updated traditional style on an oversized lot backing to serene greenspace and walking trails. This light-filled home features vaulted ceilings, abundant natural light, warm wood tones, and striking metal lighting, creating an inviting and distinctive living experience in a highly desirable neighborhood. The open entry showcases picture windows, while angled vaulted ceilings in the living and dining areas offer architectural interest and comfortable gathering spaces. Engineered hardwood floors flow throughout, complemented by expansive windows that bring the outdoors in. The kitchen opens seamlessly to the nook and great room, featuring extensive built-ins, tile counters, a gas cooktop, double ovens, and a generous pantry. The great room impresses with soaring ceilings, a cozy fireplace, and a wall of windows framing tranquil garden views. French doors lead to a bright sunroom with vaulted ceilings and skylights—ideal for a home office, bonus space, or flex living. Upstairs, the primary suite and two additional bedrooms are thoughtfully arranged, with a Jack-and-Jill bath connecting the secondary bedrooms. The spacious primary retreat includes custom floor-to-ceiling built-ins, double vanity, organized closet system, and a walk-in shower. Set on a .25-acre lot, the backyard is a true gardener’s haven with raised beds, lush perennials, lawn areas, trellised vines, a greenhouse, potting shed, and a peaceful courtyard. Backing to expansive greenspace, this property offers exceptional privacy and a rare connection to nature.

22971 SW HOSLER WAY, Sherwood

$1,025,000
3 Beds 2 Baths 137053156 MLS
Set within the highly sought-after Sherwood View Estates, this custom-built home offers a refined take on one-level living in one of Sherwood’s most established neighborhoods. Known for its enduring quality, generous homesites, and close proximity to Old Town Sherwood, this location continues to attract those seeking both convenience and a sense of retreat. Thoughtfully designed and built with lasting craftsmanship, the home spans over 3,200 square feet on one level, creating a seamless flow that supports both everyday living and effortless entertaining. Rich millwork, vaulted ceilings, and expansive windows bring warmth and natural light into the main living spaces, while carefully curated finishes reflect a level of quality that stands apart. At the heart of the home, the spacious kitchen features a large gathering island, double ovens, ample storage, a nook and a butler’s pass-through, connecting the living areas seamlessly. The vaulted great room, anchored by a fireplace and custom built-ins, offers an inviting place to gather, while the formal dining room is well-suited for hosting. The primary suite provides a peaceful setting with its own fireplace, patio access, and a well-appointed ensuite with soaking tub, walk-in shower, and dual vanities. Two additional bedrooms, a dedicated office, a generous utility space and a three-car garage offer flexibility for a variety of lifestyles. Outside, the vaulted covered patio and built-in BBQ create an effortless extension of daily living, surrounded by established landscaping that offers privacy and a calm connection to the outdoors. Located just minutes from restaurants, shops, and community events in downtown Sherwood, this home presents a rare opportunity to experience elevated one-level living in a location that continues to stand the test of time.

23827 SW ROBSON TER, Sherwood

$1,100,000
4 Beds 3 Baths 200406948 MLS
$1,100,000 | 4 Bed | 3 Full Bath | 4,781 SF | Garage + large shop. Are you ready for summer in wine country? Experience the best of Oregon's wine country in this stunning 4,781 sq. ft. daylight ranch, secretly situated on 2.6 acres of serene beauty. In this neighborhood of $2mil+ homes, this is your opportunity to put your own custom finishes on this solid canvas! With four bedrooms, three baths, an office, and two levels, this home offers a spacious and versatile layout, complete with hardwood floors throughout the main level wrapped in custom handwoven rugs for added elegance. The tile roof adds durability and charm, while the outdoor deck surrounds the house to provide a peaceful retreat with views of mature landscaping and surrounding trees. Likewise the circular driveway surrounds the house and shop, including a permeable paver section near the house, giving two routes of entry and exit. The lower level has an extra bonus room, a fourth bedroom, an office, and a wet bar. A storage/workshop on the same level adds functionality for hobbies or projects. The property is a haven for those seeking both functionality and lifestyle. A detached 40x60 warehouse includes a second 40x20 office and a 40x40 open shop with concrete floors, ideal for small business operations or creative pursuits. The solar array with storage batteries provide essential backup power. Nestled between the award-winning towns of Sherwood and Newberg, this home is surrounded by breathtaking vistas of vineyards, hazelnut orchards, and Christmas tree farms. You will benefit from a Sherwood address yet Yamhill county taxes and Newberg schools. The mature landscaping, enhanced by native plantings, provides year-round beauty and tranquility. Enjoy cycling to Bald Peak State Park and taking in the spectacular views of Yamhill County. This property is more than a home—it's a destination. Come see for yourself why this is the perfect place to call home.

16645 NE LEANDER 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

$2,442,500
6 Beds 5 Baths 385340947 MLS
Original Owner, Custom Sherwood estate — Over sixteen private acres in Oregon’s beautiful wine country featuring an income producing Christmas Tree Farm. This impressive six-bedroom, five-bathroom residence combines luxury and functionality. From the moment you arrive, you’ll notice the attention to detail and smart upgrades that make this property truly stand out. Inside, a flowing floor plan showcases vaulted ceilings, rich millwork, and expansive windows that fill the home with natural light. The gourmet kitchen features high-end appliances, a large island, and seamless flow into the spacious great room — perfect for entertaining or relaxing. The primary suite offers a private retreat on the main floor with a spa-inspired bath and stunning views of the surrounding landscape. Five additional generously sized bedrooms provide flexibility for guests, a second home office, or multi-generational living. Central vacuum and whole house sound system! Step outside to enjoy resort-style amenities. A sparkling, solar heated pool - enjoyable from spring through fall! Large sport court - basketball, pickleball or tennis anyone? Expansive patios to spread out and take it all in. There’s room for recreation, gardening, animals and all your toys. Enjoy mature, fruit producing Kiwi, Pomegranate and Grapes while adding what inspires you to the fertile garden plot, ready for planting. So many ways to enjoying the peace and quiet of country living. This is more than a home — it’s a lifestyle. Experience it all just minutes from charming Old Town Sherwood shops & entertainment, Top-Rated Sherwood Schools and a quick commute to I-5. Welcome to your next chapter!

13680 SW MORGAN RD, Sherwood

$1,599,000
4 Beds 4 Baths 762893847 MLS
In a market where you can’t easily buy prime view property and build a multigenerational home at this price point, this one stands out! Perched atop one of Sherwood Wine Country's most coveted hilltop settings with Mt. Hood and valley views, this custom daylight ranch estate delivers an extraordinary combination of scale, privacy, and versatility on a premier 1.5-acre lot at the end of a private drive, representing the most compelling value-per-square-foot in the 97140 luxury market. Thoughtfully designed for modern living, the home offers a rare multigenerational floor plan with up to three independent living quarters, each with private spaces and full baths. The flexible layout is also ideal, accommodating a guest wing, home office, or private studio. The main level impresses with soaring vaulted ceilings, formal dining, and a gourmet kitchen that flows effortlessly to expansive patios, where sweeping Yamhill Valley and vineyard vistas stretch to the horizon.You'll also find generous living spaces, an elevated primary suite, and additional bedrooms here.The lower level is an entertainer's sanctuary, complete with a bedroom suite, dedicated wine cellar, sauna, and wet bar, a natural complement to the world-class wineries just minutes away. The massive 6-car tandem garage with mower access provides unmatched utility for the collector or hobbyist of any kind. Additional highlights include ADA-friendly features, newer high-efficiency HVAC systems, 50 year tile roof, ensuring longevity, comfort and accessibility at every turn. Whether you're envisioning a private estate, a multigenerational compound, or a luxurious retreat, this hilltop masterpiece offers the canvas and the footprint to bring that vision to life.Quiet. Private. Unmistakably Oregon. Just minutes from the Allison Inn and Spa, along with some the finest vineyards and wineries the Willamette Valley has to offer. Opportunity and views this good shouldn't wait. And neither should you.

30525 NE CANTER LN, Sherwood

$2,175,000
4 Beds 3 Baths 204128147 MLS
A custom-crafted escape with unmatched charm and potential! 2014 Craftsman-style home, set on 4.23 acres spanning 3,117 square feet, this property invites you to enjoy both comfort and elegance amidst the breathtaking Parrett Mountain and vineyard views. Step inside to discover an open floor plan that seamlessly connects thoughtfully designed spaces. Impressive features abound, including durable wood-laminate floors, custom cabinetry, and exquisite stone accents. Expansive windows flood the home with natural light, showcasing stunning territorial views. The gourmet kitchen is a chef's paradise, featuring quality appliances, polished granite countertops, and a spacious island—ideal for hosting unforgettable gatherings. Adjacent, the inviting great room centers around a cozy fireplace, with high vaulted ceilings and beautiful built-in cabinetry, perfect for relaxing evenings. This home boasts four bedrooms plus a versatile den/office. The fourth bedroom upstairs serves double duty as a bonus room with its own full bath, offering ultimate flexibility for guests, recreation, or personalized use. The master suite with a spa-inspired ensuite has heated floors, and a walk-in closet. A private den/office provides a functional yet serene workspace for remote work or study. The expansive patio, complemented by a beautiful water feature and natural gas fire-pit, provides a tranquil setting for outdoor living. The extensive yard space offers endless possibilities for anyone with visions of a pool or hobby farm. A large "contractor's shop" + half-bath is a standout feature, ideal for projects or ample storage. Its generous size makes it suitable for various uses, from workshops to vehicle or equipment storage. There is plenty of room for a small barn, pool or sports court. Located just minutes from modern conveniences but still has privacy and stunning rural vineyard views, all season long. Just a few minutes to the conveniences of Sherwood or Newberg.

21501 SW NICHOLAS VIEW DR, Sherwood

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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 © 2026 RMLS of Portland, Oregon. All information provided is deemed reliable but is not guaranteed and should be independently verified. This content last updated on . Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.