Sherwood, OR Real Estate Search

Sherwood, OR Homes with a Pool for Sale

Real estate in Sherwood, OR offers a delightful selection of homes with pools for sale, catering to those who crave outdoor relaxation and entertainment. Nestled in the scenic landscape of the Pacific Northwest, Sherwood boasts a family-friendly atmosphere and a vibrant community. Homes with pools in this area often feature spacious backyards that provide a perfect setting for summer gatherings, barbecues, and tranquil evenings under the stars. With a variety of architectural styles available, potential buyers can find everything from charming ranch-style homes to modern two-story residences, all equipped with inviting pools to enhance the living experience. This desirable feature not only adds aesthetic appeal but also presents a perfect retreat for hot summer days, making Sherwood a coveted location for homebuyers seeking a blend of comfort and leisure.

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Newest Sherwood, OR Homes with a Pool for Sale

$1,150,000
3 Beds ⋅ 2 Baths ⋅ 440391829 MLS
Set on 5 picturesque acres with breathtaking views of Mount Hood, this exceptional property presents a phenominal opportunity to create a luxury estate tailored to your vision. This existing home has been taken down to the studs and the exterior needs fresh surfaces, offering a blank canvas for a full remodel, or, take advantage of the seller's approved building plans and start fresh with a brand new custom residence. An in-ground pool project has already been initiated by Victory Pools, with plumbing infastructure in place adding significant value toward your future backyard that only dreams are made of. Approximatley 3 acres of Christmas trees enhance the properties charm, privacy, and income potential. Surrounded by stunning natural beauty and endless possibilitys, this is an extraordinary opportunity to build a one-of-a-kind estate in a truly spectacular setting.

27616 SW 170TH AVE, Sherwood
$2,854,000
7 Beds ⋅ 6 Baths ⋅ 384943534 MLS
Experience the Pacific NW at its best on this extraordinary 19.9-acre private estate. Set behind a stately wrought-iron gate and accessed by a vineyard-lined drive, the property showcases a rare blend of elegance, recreation, and multi-generational living. This custom craftsman home is designed for both grand entertaining and everyday comfort, featuring expansive living spaces, vaulted ceilings, abundant natural light, multiple fireplaces, Brazilian Cherry floors, professional-grade appliances, and sweeping countryside views from every level. The luxurious primary suite serves as a private retreat, featuring its own foyer, coffee station, fireplace, balcony, spa-inspired bath with marble floors, a soaking tub, and an oversized walk-in closet. The walk-out lower level is dedicated to recreation and wellness, offering a large family room, media and game area, exercise room, professional-grade cedar sauna, wine cellar, and flexible space currently used as a recording studio. Outdoor living centers around a spectacular 40,000-gallon Neptune pool, covered deck areas, and panoramic views. A thoughtfully designed flexible or multi-generational living wing provides approximately 2,000 Sq. Ft. of additional living space with 3 bedrooms, 2 baths, office, full kitchen, living room, private entrances, attached garage, and its own outdoor deck, overlooking the pool and forested views. The estate grounds are a destination unto themselves, showcasing professionally landscaped gardens, a dramatic koi pond with cascading water features and oversized boulders, a custom greenhouse with water, power, a circular drive, extensive exterior lighting, and a 19-zone irrigation system. Modern conveniences include 3 heat pumps, 5 climate-controlled zones, an Aquatherm heat exchanger, a high-flow well, and a home security system. This exceptional offering combines privacy, luxury, and comfort on nearly 20 acres in the Chehalem Mountain AVA of Oregon Wine Country.

21029 SW LeBeau RD, Sherwood
$3,950,000
4 Beds ⋅ 4 Baths ⋅ 379302411 MLS
There is a moment driving through the vineyard rows toward the gate, when it becomes clear that this property is something different. The vines run along both sides of the private drive. The Cascade Range on the horizon. And then the house appears: French country architecture at its finest, hand-laid Austin Cream limestone, powder blue shutters, and an arched stone entry set down in the heart of the Willamette Valley. Designed and built by Teal Point Custom Homes as the builder's personal residence, every finish, every material, every detail chosen without compromise. The foyer is lined in Austin Cream limestone. The great room is anchored by a floor-to-ceiling stone fireplace beneath dark wood coffered beams. The kitchen features a hammered copper range hood, cabinetry finishes that read like collected antiques, artisan hand-painted tile, and vineyard views through arched windows. A climate-controlled wine room sits just off the entry behind a full stone arch. At 5,913 square feet on two private acres within a gated 52-acre estate, the home is as substantial as it is refined. Four bedrooms, a dedicated home office, a lower-level bonus, two living spaces, and outdoor living that rivals any resort in the region. The primary suite is its own retreat: vaulted beamed ceilings, arched details, a soaking tub overlooking the vineyard, furniture-style custom cabinetry, and an arched tile surround framing the walk-in shower entry. Outside, the covered terrace opens to a rectangular pool surrounded by vineyard. Mt. Hood straight ahead. A formal English garden with stone fountain, a putting green, and mature Italian cypress anchors the grounds. French country meets Pacific Northwest, elevated, intentional, and complete. Just two miles from downtown Sherwood, close enough to everything, worlds away from ordinary.

20923 SW EDY 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
$1,249,000
4 Beds ⋅ 3 Baths ⋅ 294873014 MLS
Located in one of Sherwood's most desirable areas, this 1.35 acre property, with valley views, offers rare space, privacy & versatility, just minutes from town. The multi-level layout creates separation & flexibility, while the many outdoor amenities including, heated pool, sport court, sauna & spacious yard are great for entertaining & everyday living. Spacious living room features beautiful fireplace & wall of windows w/gorgeous views. Dining area has slider to extended deck. Updated kitchen has granite countertops, large eating island, built-in desk and stainless applcs, including refrigerator & built-in range. Spacious primary suite has w-in closet & updated bathroom (2022} w/dual sinks, granite cntrtps, tiled shower & jetted tub. Updated lower level (2023) has LVP flooring, family room w/door to extended patio & pool access, 2 bdrms, full bathroom & storage. The property includes fenced in-ground heated pool, sauna, pizza oven, sport court, garden beds, fruit trees, pet kennel and shed. Attached 2-car garage & detached 1-car garage/workshop. Engineered hardwood flooring (2026). Carpet (2023). Furnace & AC (2018). Ring doorbell. Sprinkler system. Located near schools, Snyder park, dog park & Old Town Sherwood w/shopping, dining & so much more! Conditional city approval in place for proposed 3 lot minor partition. Buyers to complete independent due diligence.

15379 SW SUNSET BLVD, 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
$575,000
3 Beds ⋅ 2 Baths ⋅ 792313286 MLS
Location is everything with this Sherwood Village home! Backing directly to Langer Park, this property offers privacy, nature views, and unbeatable walkability. You’ll be just minutes from Target, Walmart, and Langer’s Entertainment Center, as well as local dining and schools, a perfect blend of convenience and community. Step inside to find vaulted ceilings that create an open, airy feel. The main level features a bright living room, family room, and dining area, plus a kitchen nook overlooking the backyard- ideal for morning coffee or casual meals. You’ll also find a laundry room, half bath, and a bonus room that can flex as an office, playroom, or guest space. Upstairs, the primary suite offers vaulted ceilings, a ceiling fan, dual sinks, and a walk-in closet. Two additional bedrooms provide flexibility for family, guests, or hobbies, with one offering extra storage or flex space. The spacious backyard is ready for your touch, with room to garden, entertain, or simply relax while enjoying your view of the park!

16045 SW RED CLOVER LN, 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.