Lake Oswego Homes with Cottage Style

Lake Oswego Homes with Cottage Style

Welcome to Lake Oswego, Oregon—a picturesque city nestled in Clackamas County, just a stone's throw from the vibrant heart of Portland. Renowned for its stunning lake, lush parks, and a tight-knit community, Lake Oswego offers a unique blend of suburban tranquility and urban convenience. With its charming downtown area filled with boutique shops, gourmet restaurants, and art galleries, this city is a haven for those who appreciate a rich cultural scene.

One of the most enchanting aspects of Lake Oswego is its diverse architectural landscape, particularly the delightful cottage-style homes that dot the neighborhood. These quaint and cozy residences exude a warmth that invites you to unwind and enjoy the simple pleasures of life. Often characterized by their charming gabled roofs, inviting front porches, and well-tended gardens, cottage-style homes in Lake Oswego create a storybook atmosphere that captivates residents and visitors alike.

Living in a cottage home here means more than just enjoying a beautiful aesthetic; it’s about embracing a lifestyle that values community, nature, and comfort. With access to scenic walking trails, serene lakeside parks, and a plethora of outdoor activities, residents can savor the beauty of the Pacific Northwest right at their doorstep.

Whether you’re looking for a cozy retreat or a vibrant community to call home, Lake Oswego’s cottage-style residences offer an idyllic setting that perfectly complements the charm of this enchanting city. Come discover the magic of Lake Oswego and find your dream home in this enchanting corner of Oregon!

Newest Lake Oswego Homes with Cottage Style

5675 CHILDS RD, Lake Oswego
$689,000
2 Beds ⋅ 2 Baths ⋅ 412826516 MLS
Vaulted ceilings, a creative loft space, and personality throughout — this home is full of character and ready for your vision. Situated on a large corner lot along a private rd in unincorporated Clackamas County, it offers space, flexibility, and room to make it uniquely your own. A wonderful loft area, which could be used as a second bedroom, adds versatility to the layout, while two fully remodeled bathrooms showcase distinctive design and updated comfort. Unique details and thoughtful touches create a home with warmth and individuality, leaving room for imagination throughout. A pre-home inspection has been completed with many items already addressed, providing added confidence for buyers. Major systems include an updated new roof. Outside, enjoy a long driveway with ample parking and plenty of room for cars, trucks, recreational vehicles, or toys. The property also features an approx. 500 sq. ft. detached studio — ideal for creative space, hobbies, or a private retreat (not included in home square footage). A working hot tub (currently winterized) and spacious yard complete the outdoor setting. A rare opportunity to personalize a home with character, space, and flexibility in a peaceful yet convenient location.

5675 CHILDS RD, Lake Oswego
3750 UPPER DR, Lake Oswego
$1,175,000
3 Beds ⋅ 2 Baths ⋅ 534588003 MLS
A rare build or remodel opportunity in one of Lake Oswego's most sought after lake view locations. Minutes from the shops and restaurants of Lake Grove, with walking distance access to three Oswego Lake easements: Goodin, Springbrook, and Summit Court. With lake views from the backyard, this private 1940s cottage with Nantucket style shingle siding offers single level living and all the charm of classic Lake Oswego. Oak hardwood floors and parquet entry set a warm tone throughout the main level, where three bedrooms, two baths, and an office are all conveniently on one floor. The office flows into the main living area, anchored by a family room with a warm gas fireplace and wood accent wall, a dining area with a mini wet bar, and a sun filled sitting room with a generous skylight and French doors to the backyard. The open concept kitchen is designed for easy flow and gathering, with a walk in pantry for added storage. The primary suite includes a walk in closet, French doors to the wraparound deck, and a view of the serene water feature. A lower level bonus room with new carpet and fresh paint offers flexible space for a flex/media room, home gym, or guest retreat, alongside a large dry storage area. Gracious grounds with raised beds, a meandering path, and mature backyard gardens complete an outdoor setting made for quiet enjoyment. A freestanding cottage with its own private entrance, lake views, lounge area, and two sliding glass doors to a spacious deck rounds out this exceptional property. Served by Lake Grove Elementary, Lake Oswego Junior High, and Lake Oswego High School, with a detached two car garage completing the package, this is an opportunity to secure one of Lake Oswego's most coveted lakeside addresses.

3750 UPPER DR, Lake Oswego
311 E AVE Unit #7, Lake Oswego
$649,900
2 Beds ⋅ 2 Baths ⋅ 776248346 MLS
Open Sat 2:00-4:00. Introducing The Oswego Cottages in Lake Oswego’s sought-after Historic First Addition neighborhood ideally located just blocks from downtown Lake Oswego, Tryon Creek State Natural Area, local restaurants, grocery stores, the theater, library, coffee shops, and more. Beautifully designed featuring stylish kitchen with quartz countertops, stainless steel appliances, and a spacious island perfect for gatherings. Step outside to a private covered patio, ideal for year-round outdoor living and entertaining. Pictures are of similar unit.

311 E AVE Unit #7, Lake Oswego
4428 SUNSET DR, Lake Oswego
$820,000
3 Beds ⋅ 1 Baths ⋅ 211042212 MLS
Every once in a while, a home comes along that simply feels different. A newly renovated laundry and mudroom sets the tone for the thoughtful design found throughout this one-of-a-kind Lake Oswego property, pairing elevated finishes with beautifully organized, everyday functionality. Thoughtfully transformed over the years by an interior designer, every room reflects timeless design, quality craftsmanship, and spaces meant to be enjoyed.At the heart of the home, the beautifully renovated kitchen was designed to bring people together. Quality finishes, thoughtful details, and seamless flow into the surrounding living and dining spaces make it equally suited for everyday living, holiday gatherings, and memorable evenings with family and friends.Just beyond the main home, a detached private flex space offers endless possibilities. Originally designed as a private interior design workspace, this versatile space is ideal for a home office, art studio, fitness studio, wellness room, hobby space, or creative retreat.Step outside and discover what truly sets this property apart. Nestled on an expansive, park-like lot, the grounds feel like your own private sanctuary. Towering evergreens create a breathtaking natural backdrop while lush lawn, mature landscaping, raised garden beds, a tranquil fountain, charming pathways, and thoughtfully designed outdoor living spaces invite you to slow down and savor every season. Whether hosting summer dinners under the trees, harvesting from the garden, or enjoying a quiet morning coffee, this backyard was designed to be experienced.Completing the lifestyle, the property includes access to the Goodin, Springbrook, and Summit Court Lake Easements, offering opportunities to swim, paddle, and enjoy everything that makes Lake Oswego living so special.

4428 SUNSET DR, Lake Oswego
310 G AVE Unit #5, Lake Oswego
$649,900
2 Beds ⋅ 2 Baths ⋅ 740321551 MLS
Open Sat 2:00-4:00. This cottage has its own gate to the off-street assigned parking and a large outdoor area. Introducing The Oswego Cottages in Lake Oswego's sought-after Historic first Addition neighborhood ideally located just blocks from downtown Lake Oswego, Tryon Creek State Natural Area, local restaurants, grocery stores, the theater, library, coffee shop, and more. Beautifully designed and high-quality finishes featuring stylish kitchen with quartz counter-tops, stainless-steel appliances, and a spacious island perfect for gatherings. Step outside to a private covered patio, ideal for year-round outdoor living and entertaining. Micro HOA of only $103 a month.

310 G AVE Unit #5, Lake Oswego
808 3rd ST, Lake Oswego
$649,900
2 Beds ⋅ 2 Baths ⋅ 790701172 MLS
Open Sat 2:00-4:00. Introducing The Oswego Cottages in Lake Oswego's sought-after Historic first Addition neighborhood ideally located just blocks from downtown Lake Oswego, Tryon Creek State Natural Area, local restaurants, grocery stores, the theater, library, coffee shop, and more. Beautifully designed featuring stylish kitchen with quartz counter-tops, stainless steel appliances, and a spacious island perfect for gatherings. Step outside to a private covered patio, ideal for year-round outdoor living and entertaining. (Pictures are of a similar unit)

808 3rd ST, Lake Oswego
2430 SUMMIT CT, Lake Oswego
$2,745,000
4 Beds ⋅ 3 Baths ⋅ 534254073 MLS
A rare waterfront Richard Sundeleaf-designed treasure on Oswego Lake, this beautifully renovated Tudor Revival-style English cottage rests on a coveted 0.33-acre double lot with 100+ feet of shoreline, southern exposure, and sweeping nearly 180-degree lake views. Offering 3 bedrooms, 3 baths, and timeless architectural character, the home blends historic pedigree with thoughtful modern updates. Highlights include expansive picture windows, refined living spaces, a main-level primary suite, updated kitchen with premium appliances, and seamless indoor-outdoor living. The waterfront experience is exceptional, featuring a boathouse with rooftop sundeck, dock, swim ladder, boat lift, lakeside lawn, and stone patio with rustic outdoor fireplace. Just minutes to downtown Lake Oswego’s boutiques, dining, Farmers Market, and top-rated schools, this is a singular opportunity to own a landmark lakefront residence.

2430 SUMMIT CT, Lake Oswego
17332 LAKE HAVEN DR, Lake Oswego
$1,879,000
4 Beds ⋅ 2 Baths ⋅ 637966999 MLS
Rarely does an Oswego Lake property offer 0.40 acres of flat main canal frontage, exceptional privacy, mature gardens, and the flexibility to enjoy today while thoughtfully shaping its future. Tucked behind lush landscaping in one of Lake Oswego's most desirable waterfront settings, this remarkable property offers an increasingly rare combination of land, lifestyle, and long-term potential. The 0.40-acre homesite is the true centerpiece. Flat waterfront lots of this size on Oswego Lake's main canal are becoming exceptionally difficult to find, creating an estate-like setting with expansive lawns, mature trees, colorful gardens, and seamless indoor-outdoor living. Launch your boat from the private dock with covered boat lift, paddleboard or kayak from your backyard, entertain along the water, or simply enjoy peaceful mornings overlooking the canal. Grandfathered lake water rights for irrigation help preserve the mature landscape that has taken decades to create. Thoughtfully maintained, the home is comfortable to enjoy from day one, offering four bedrooms, hardwood floors, an updated kitchen, two gas fireplaces, inviting living spaces, and beautiful garden and water views. A detached oversized two-car garage includes a finished, heated and cooled bonus room, ideal for a private office, gym or creative workspace. Professionally prepared conceptual architectural plans are available for buyers who wish to reimagine the home over time, illustrating one possible renovation while respecting the property's existing character and extraordinary setting. Whether you're searching for a move-in-ready waterfront home, an exceptional homesite for a future luxury renovation, or a legacy property to enjoy for generations, this rare main canal offering presents an opportunity that is becoming increasingly difficult to find on Oswego Lake.

17332 LAKE HAVEN DR, Lake Oswego
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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.

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