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. Known for its stunning natural beauty, Lake Oswego boasts serene waterfronts, lush parks, and a charming downtown area that perfectly blends modern amenities with a quaint, small-town feel. With a rich history dating back to the 1800s, this vibrant community offers a unique mix of cultural experiences, recreational activities, and a welcoming atmosphere.

One of the standout features of Lake Oswego is its enchanting collection of cottage-style homes. These delightful abodes, often characterized by their cozy aesthetics, intricate woodwork, and inviting gardens, capture the essence of a fairytale setting. Imagine waking up in a charming cottage with a white picket fence, surrounded by blooming flowers and the gentle sounds of nature. These homes often come with spacious layouts, perfect for families or those seeking a peaceful retreat.

Cottage-style homes in Lake Oswego are not just about beauty; they also reflect a sense of community and connection. Many of these residences are located within walking distance of local shops, cafes, and parks, making it easy to enjoy the best that Lake Oswego has to offer. Whether you're strolling along the scenic waterfront or exploring the vibrant arts scene, you'll find that this city embraces a lifestyle that is both relaxed and enriching.

In Lake Oswego, the charm of cottage living meets the allure of a thriving community, making it an ideal place to call home. Discover the magic of Lake Oswego, where every corner holds the promise of a cozy, fulfilling life.

Newest Lake Oswego Homes with Cottage Style

$729,000

3 Beds ⋅ 2 Baths ⋅ 236793980 MLS

Step into your very own storybook setting in the coveted Bryant neighborhood of Lake Oswego! This delightful 1950s gem captures the essence of an enchanted cottage with all the modern conveniences! Inside, new interior paint complements 3 light-filled bedrooms and 2 full bathrooms, while two wood-burning fireplaces create a soulful environment for relaxing evenings with friends and family. The classic kitchen is equipped with stainless steel appliances, a new disposal, paint and artful light fixtures ensuring solid functionality and a dash of style! Throughout the home, natural light pours through newer Milgard windows. Wall-to-wall carpet feels great underfoot, and a refreshed downstairs bathroom features newer tile and a new toilet. Beyond its lovely curb appeal, this home offers genuine value due to its many structural and exterior upgrades. You can rest easy knowing there’s a brand-new roof, fresh exterior paint, new stairs and banister on the front porch, updated landscaping, and a radon mitigation system in place. Outdoor living is a dream on the brand-new back deck overlooking a huge backyard, with ample space to garden and a dedicated well to keep the yard lush all summer long! Year-round climate control is handled by a newer HVAC system and water heater that are expected to operate reliably for years to come. But it doesn’t end there: The enchantment extends into the surrounding neighborhood, as this home is within the boundaries of the beloved Lake Grove Swim Park, where kids and adults enjoy access to one of Lake Oswego’s sweetest summer traditions on Oswego Lake! Plus, you’re just minutes from top Lake Oswego schools including the newly-rebuilt Lakeridge Middle School, popular local eateries, premier shopping on Boones Ferry Road and the Bridgeport Village Mall, and easy freeway access to I-5 and Highway 217. It’s a whimsical, turnkey retreat that offers the best of Lake Oswego living at a compelling price for the Bryant neighborhood!

17521 HILL WAY, Lake Oswego

$799,000

3 Beds ⋅ 1 Baths ⋅ 211042212 MLS

Every once in a while, a home comes along that simply feels different. Thoughtfully transformed over the years by an interior designer, this one-of-a-kind Lake Oswego property is a reflection of timeless design, quality craftsmanship, and spaces meant to be enjoyed. Every room has been carefully curated to feel warm, inviting, and effortlessly livable, blending character with modern comfort in a way that’s difficult to replicate.At the heart of the home, the beautifully renovated kitchen was designed to bring people together. With quality finishes, thoughtful details, and seamless flow into the surrounding living and dining spaces, it’s equally suited for everyday living, holiday gatherings, and memorable evenings spent 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 you’re 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, relax along the shoreline, and enjoy everything that makes Lake Oswego living so special.

4428 SUNSET DR, Lake Oswego

$889,000

3 Beds ⋅ 3 Baths ⋅ 195828976 MLS

A one-of-a-kind historic gem, this Storybook Cottage was built in 1918 by Nan McBride on the 600 acre estate of the area's first resident, P. Farnsworth Morey. Decorative period charm fills every eyeful - in the architecture, the interior and the setting. Hidden behind a tall laurel hedge, rounded garden arbors and white picket fences frame the house with its quaint shake siding, double hipped roof and multi-paned windows. Inside, arched doorways, beadboard walls, cute shelved nooks and tin metal-looking accents add vintage whimsy to the unique floorpan. The roomy Living Room has a big fireplace, French doors to a small garden and a bank of windows viewing an outdoor patio. The Kitchen is a charming and functional combo of rustic wood cupboards, marble counters and SS appliances, and it opens to the formal Dining Room. Upstairs in the airy Primary, the natural wood ceiling follows the roofline angles creating a warm cozy feeling, and four windows look out to treetops. Two more sweet Bedrooms, one Den or Office, and three remodeled Bathrooms complete this enchanting English cottage. Out back, two decks (one w/hot tub) view the wooded ravine with a creek at bottom, a protected riparian area. McBride named her cottage "Mole End" taken from the popular novel "The Wind In The Willows." Along with a few historic souvenirs that are left with the house, a carved wooden statue of characters from the story greets visitors at the main entry. This erstwhile estate of the Morey family is now an area of upscale homes, reputable schools, and lovely, leafy walks along the river or to George Rogers Park. Just a 5-minute drive to the vibrant center of Lake Oswego where there are shops, restaurants and other amenities.

2805 GLENMORRIE DR, Lake Oswego

$1,749,000

3 Beds ⋅ 3 Baths ⋅ 507036544 MLS

This beautifully reimagined Cape Cod home combines lake views, 3 lake easements, and a fully remodeled designer interior in one of the area's most sought-after neighborhoods. Enjoy paddleboarding, kayaking, shopping and fine dining just steps from your door, then return home to nearly 2,000 sq. ft. of beautiful, light-filled living space. Premium finishes throughout featuring a chef's kitchen with premium Café appliances, custom cabinetry, and seamless indoor-outdoor living through dramatic accordion doors that open to a year-round covered space with built-in heaters. The main floor offers a flex space to be an office or guest room with a built-in murphy bed and a full bathroom. Upstairs is a luxurious primary suite with a vaulted ceiling, lake views and a private balcony. Customized built-in cabinetry and a spa-like primary bathroom with tub and shower. The second bedroom upstairs has it's own private deck with lake views and vaulted ceilings. The basement offers a spacious flex space to watch movies or use as a bedroom. With 3 bedrooms, 3 full baths, office/guest accommodations, a spacious bonus room, and a luxurious primary suite with lake views, every space has been thoughtfully designed. Smart home technology, EV charger, a fenced backyard with multiple entertaining areas and private balconies complete this exceptional offering.

214 NORTHSHORE RD, Lake Oswego

$650,000

2 Beds ⋅ 2 Baths ⋅ 740321551 MLS

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

$2,995,000

4 Beds ⋅ 3 Baths ⋅ 534254073 MLS

A rare Richard Sundeleaf-designed lakefront treasure on Oswego Lake, this beautifully renovated 1939 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 completed in 2009 and 2025. Highlights include expansive picture windows, refined living spaces, a main-level primary suite, updated kitchen with premium appliances, multiple fireplaces, 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

$550,000

2 Beds ⋅ 2 Baths ⋅ 744947201 MLS

Live NON DISTRESSED Auction August 13th at 12:00pm! Bidding to start from $550,000.00! 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.

804 3rd ST Unit #C1, Lake Oswego

$1,999,500

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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