Lake Oswego Homes with On Street Parking

Welcome to Lake Oswego, Oregon – a picturesque haven that perfectly blends suburban charm with urban convenience. Nestled just a short drive from downtown Portland, this vibrant city is renowned for its stunning natural beauty, top-rated schools, and a strong sense of community. With its serene lakes, lush parks, and scenic trails, Lake Oswego offers residents an idyllic lifestyle that encourages outdoor recreation and relaxation.

One of the many appealing features of Lake Oswego is its diverse array of homes, particularly those that provide convenient on-street parking. This thoughtful amenity not only enhances accessibility for residents and their guests but also contributes to the neighborhood's inviting atmosphere. Imagine returning home after a long day, where ample on-street parking makes it easy to welcome friends and family or simply enjoy the peaceful surroundings of your community.

The real estate in Lake Oswego is as varied as its residents, with charming single-family homes, modern townhouses, and luxurious waterfront properties available. The city’s commitment to maintaining a high quality of life is evident in its well-maintained streets and parks, making it a perfect place for families, young professionals, and retirees alike.

Whether you’re exploring the vibrant local shops and restaurants or taking a leisurely stroll along the scenic waterfront, Lake Oswego truly has something for everyone. Embrace the lifestyle you’ve always dreamed of in this enchanting city, where comfort meets convenience, and every day feels like a getaway. Discover your dream home in Lake Oswego today!

Newest Lake Oswego Homes with On Street Parking

$1,695,000

5 Beds ⋅ 3 Baths ⋅ 288488592 MLS

Originally built by Eslinger Homes as the developer’s personal residence, this exceptional Lake Oswego home offers a rare blend of timeless craftsmanship, architectural beauty, and everyday livability. With 5 bedrooms, 3 full baths, and a versatile main-level flex room, every space has been thoughtfully designed to bring people together. Soaring ceilings, skylights, walls of glass, wide-plank hardwood floors, shiplap accents, brushed brass hardware, and black-framed windows create a warm, refined Northwest aesthetic. At the heart of the home, an expansive 10+ foot island anchors a beautifully appointed kitchen featuring a farmhouse sink, 5-burner gas cooktop, double ovens, breakfast nook, oversized walk-in pantry, and butler’s pantry. The adjoining great room extends naturally to a covered outdoor living space with vaulted cedar ceilings, skylights, a gas fireplace, TV, and a spacious, level backyard designed for year-round entertaining. The private primary suite offers vaulted ceilings, a spa-inspired bath, and an oversized walk-in closet. Hardwood flooring is carried throughout the home, while marble-look porcelain tile, designer lighting, a Venetian plaster fireplace surround, and integrated smart home features beautifully complement the home's enduring design. Just minutes from parks, top-rated schools, shopping, dining, and everyday conveniences, this house is set within one of Lake Oswego's most walkable and established neighborhoods where mature trees, wide streets, and nearby amenities make it easy to enjoy the best of L.O!

6040 LAKEVIEW BLVD, Lake Oswego

$1,275,000

5 Beds ⋅ 3 Baths ⋅ 372920898 MLS

Situated on a private 0.61-acre lot in Lake Oswego, this turn-key home offers breathtaking mountain and river views. The grand two-story entry welcomes you into light-filled living spaces with hardwood floors and a formal living room with a wood-burning fireplace. The gourmet kitchen has quartz counters, premium Sub-Zero, Bosch, and Viking appliances, and a butler's pantry which leads into the formal dining room. Relax in the primary suite with its private sitting room and cozy fireplace, or step outside to enjoy multiple entertaining areas in a flat, secluded yard with mature landscaping.

1300 GLENMORRIE DR, Lake Oswego

$1,495,000

3 Beds ⋅ 2 Baths ⋅ 553223786 MLS

With the jaw-dropping valley and panoramic mountain views spread out before you, walls of glass and multiple decks taking in the cinematic vistas, an elevator accessing all 3 floors, 14’ ceilings, and glamorous finishes, this stunner is the pinnacle of Lake Oswego luxury living. Enter to light-drenched drama from every angle with sliding glass doors accessing the Mt Hood view decks, soaring gas hearth and exquisite built-ins, and the kind of entertainer’s floor plan just begging to host the party of the year high above it all. The plush interiors have been finished with updated plank and luxe flooring, a reimagined gourmet kitchen with breakfast dining featuring staggering views, and many high design updates. Escape to the dedicated primary penthouse level with serene bedroom featuring a gas fireplace and view sitting area, remodeled en-suite masterpiece bathroom with soaking tub, dressing room, and executive office. Downstairs you’ll find a pleasure paradise all its own with a sprawling media room featuring big screen projector and swanky full bar, covered decks for year-round enjoyment, a private waterfall patio, exterior access fitness studio with sauna, generous guest suites, and option for a wine/flex room. Situated in a premier location in a private enclave of prestigious homes that surround delightful Nansen Park with top of the world views, nearby Mountain Park aquatic and fitness club amenities, quick access to OHSU and health care, freeways, Lake Oswego, downtown Portland and key amenities including shopping, dining, miles of verdant urban trails. An easy-care crown jewel that offers some of the clearest sight lines across the entire Portland Metro!

33 NANSEN SMT, Lake Oswego

$699,900

3 Beds ⋅ 2 Baths ⋅ 712181519 MLS

Here's a massive opportunity in First Addition! HUGE PRICE IMPROVEMENTS MADE! Don't miss your chance! Designed for true lock-and-go living, Koval Cottages offers something Lake Oswego has never seen before: new-construction, detached fee simple homes in First Addition at an attainable entry price point. Perfect for downsizers, first-time buyers, small families, seasonal residents, or anyone seeking low maintenance luxury in the city’s most charming neighborhood. Each home showcases exceptional finish work, modern contemporary design, and a refined attention to detail throughout. A rare and extraordinary opportunity to own a standalone home in the heart of First Addition. Enjoy effortless access to downtown Lake Oswego’s restaurants, boutique shopping, cafes, and one of the region’s best Saturday Markets!

262 G AVE, Lake Oswego

$919,000

3 Beds ⋅ 3 Baths ⋅ 105876237 MLS

Nestled among the trees in the highly sought-after Mountain Park community, this beautifully updated Northwest Contemporary offers the perfect blend of modern comfort and timeless design! Soaring cedar ceilings, dramatic walls of windows and abundant natural light create an inviting atmosphere while seamlessly connecting the home to its peaceful wooded surroundings. The spacious great room is anchored by a stunning floor-to-ceiling stone gas fireplace and flows effortlessly to a spacious new deck overlooking the trees. Already plumbed for a hot tub, it's the perfect setting for entertaining or creating your own private outdoor retreat. The remodeled kitchen features custom wood cabinetry, tiled backsplash, stainless steel appliances, gas cooktop, generous prep space and a large center island. A second living area with a cozy wood-burning fireplace provides additional space to relax or gather. The versatile floor plan offers spacious bedrooms, including a primary suite with soaring vaults and a spa-inspired bathroom. A secondary bedroom includes a unique loft, perfect for a reading nook or extra storage. Dual laundry areas, with one on each level, add everyday convenience. Outside, enjoy refreshed landscaping, a new fence, multiple outdoor living spaces and a peaceful backyard surrounded by nature. An oversized driveway and attached two-car garage provide ample parking and storage. Located in the award-winning Lake Oswego School District and just minutes from shopping, dining, I-5, and downtown Lake Oswego, residents enjoy Mountain Park's exceptional amenities, including miles of scenic trails, parks, playgrounds, tennis and pickleball courts, basketball courts, a fitness center, swimming pool, and a vibrant recreation center. Whether you're sipping your morning coffee among the trees or unwinding on the deck at sunset, you'll feel like you're living in your own private treehouse. Experience Northwest living at its finest and schedule your private tour today!

71 TANGLEWOOD DR, Lake Oswego

$1,295,000

3 Beds ⋅ 3 Baths ⋅ 579983047 MLS

Offered for the first time, this thoughtfully reimagined Northwest contemporary blends the architectural character of the 1960s with the modern updates. Once inside, the home offers exceptional privacy and a peaceful setting just minutes from downtown Lake Oswego. Designed for true main-level living, the floor plan features a spacious primary suite, beautifully renovated living spaces, laundry room, and a generous flex room that’s easily large enough to serve as a fourth bedroom, home office, or guest room. Vaulted wood ceilings, exposed beams, expansive windows, and sliding doors fill the home with natural light while creating a seamless connection to the surrounding landscape. The heart of the home is the completely redesigned kitchen, featuring custom cabinetry, quartz countertops, a large island, new appliances, and abundant storage. An adjoining wet bar adds both style and function. The open layout flows effortlessly into the dining and living areas before extending to expansive decks overlooking the surrounding trees and seasonal mountain views offering impressive space for outdoor living. The renovation extends well beyond the finishes with updated plumbing and electrical, a new roof, newer HVAC system, new lighting, wide-plank flooring, remodeled bathrooms, and carefully selected materials that complement the home’s original architecture while providing the confidence of updated systems. The daylight lower level offers flexibility with two oversized bedrooms, one with an adjoining sitting area, a beautifully remodeled full bath, a spacious family room with a fireplace, and direct access to a covered deck and the backyard. Whether used for guests, multigenerational living, or additional gathering space, the layout adapts to a variety of lifestyles. Thoughtfully designed landscaping, stone pathways, a custom water feature, and multiple outdoor living spaces create a peaceful setting while remaining just minutes from everything Lake Oswego has to offer.

2591 OVERLOOK DR, Lake Oswego

$2,195,000

4 Beds ⋅ 2 Baths ⋅ 103977290 MLS

Offered for the first time in nearly a century, 920 Fairway Road is one of Lake Oswego’s rarest legacy estates. Listed on the National Register of Historic Places, it is a place where architectural significance, natural beauty, and Oregon history converge. Cherished by the same family for four generations, this 1932 Craftsman/Tudor residence was commissioned by Willard Boutwell and designed by George Post, founder of Oregon’s chapter of the American Institute of Architects.Privately set on just over an acre of park-like grounds, the estate is framed by mature trees, historic stone walls, lush gardens, and the peaceful flow of Boutwell Creek. A cathedral-shaped solid oak entry door opens to soaring 16-foot vaulted ceilings, exposed timber trusses, original wide-plank oak floors, arched doorways, and a striking wood-burning fireplace featuring handcrafted metalwork by the artisan behind Timberline Lodge’s Silcox Hut.Thoughtfully designed for both grand entertaining and everyday living, the home offers four bedrooms, two full and two half baths, a spacious family room, a finished attic, and updated systems that honor its historic character. Outdoors, a spectacular 10,000-gallon pool with a stone fountain waterfall and adjoining wading pond creates a truly private retreat, complemented by two outbuildings, a chicken coop, and expansive grounds rarely found this close to downtown.Just steps from Oswego Lake Country Club and including deeded access to the coveted Forest Hills Lake Easement, the home offers the rare luxury of walking to downtown Lake Oswego’s acclaimed restaurants, boutiques, cafés, and farmers market, with Iron Mountain trails just moments away.Basement not included in square footage. Buyer to verify details.

920 FAIRWAY RD, Lake Oswego

$184,500

1 Beds ⋅ 1 Baths ⋅ 755267468 MLS

Welcome home to Mountain Park! Nestled in one of Lake Oswego's most sought-after communities, this stylish one-bedroom condo offers the perfect blend of comfort, convenience and modern living. The bright, open floor plan features an oversized kitchen island that's ideal for cooking, entertaining or gathering with friends. Expansive wall-to-wall windows fill the home with natural light and lead to a private covered patio overlooking a peaceful natural setting—your own tranquil retreat. Luxury vinyl plank flooring enhances the main living area and bedroom, while a new heat pump provides efficient year-round comfort. A new washer and dryer are included, along with one assigned parking space and the added benefit of no rental cap, making this an excellent option for homeowners and investors alike. Enjoy resort-style amenities at the Mountain Park Recreation Center, including indoor pools, a fitness center, tennis and pickleball courts, walking trails, parks, playgrounds and community events. Just minutes from highly rated schools, shopping, dining, downtown Lake Oswego and easy freeway access, this move-in-ready condo offers the best of low-maintenance living in a beautiful natural setting.

100 KERR PKWY Unit #52, Lake Oswego

$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

$1,895,000

4 Beds ⋅ 4 Baths ⋅ 747978286 MLS

Built in 2024 by an award-winning Street of Dreams builder, this like-new Contemporary home sits in the coveted Uplands neighborhood of Lake Oswego; One of the only neighborhoods where you can walk to the brand-new LO Junior High, High School and Uplands Elementary (serving Forest Hills for school years 2026/27 and 2027/28) as well as Springbrook park. Upon arrival, this striking home greets you with stacked stone and real wood siding, mature landscaping and extensive exterior lighting. The main level flows openly between a family room with high ceilings, a modern Montigo gas fireplace, and built-in shelving, opening directly to the covered deck overlooking the private backyard. The gourmet kitchen features stainless steel appliances, a Calcutta Izard quartz island, built in Subzero refrigerator, a five-in-one wall oven, bright white and wood cabinetry, and a walk in pantry with wine refrigeration. A spacious home office with walls of windows, mudroom off the garage, and beautiful half bath complete the main level. Upstairs, all four bedrooms offer large windows, blackout shades, and generous closet space. The primary suite features a walk-in closet with built-ins and a bath with a soaking tub, oversized walk-in shower, dual sinks, and heated tile floors. One of the other three bedrooms includes its own en suite bath and walk-in closet, with the remaining two sharing a full bath. The laundry room is bright and sunny with built-in shelving, counter space, and a stainless sink. The lower level is a kids haven with a oversized bonus room, plus a full bath, projector prewiring, and loads of storage. A private level yard with turf, a cement patio, upper deck, and full fencing is ready for family and pets. Enjoy swimming, paddle boarding or kayaking with three lake easements: Goodin, Springbrook Recreation, and Summit Court. Kruse Woods Village and Mercato Grove, loaded with shopping, dining and gathering, are both a short walk away.

3351 FIR RIDGE RD, Lake Oswego

$995,000

3 Beds ⋅ 2 Baths ⋅ 524060358 MLS

Designed for the ease of main-level living, this thoughtfully designed Lake Oswego home features a spacious primary suite, dedicated office, laundry room, and direct access to the garage on the main floor. Upstairs, two additional bedrooms are complemented by a generous bonus room and open loft, offering flexibility for a media room, play space, or home office.Vaulted ceilings elevate the living room, kitchen, primary suite, and office, creating an open, light-filled feel throughout. The kitchen features stainless steel appliances, a large pantry, and an oversized island that flows seamlessly into the main living spaces, making it equally suited for everyday living and entertaining.A private, fully fenced backyard with a patio extends the living space outdoors just off the kitchen and living room. Conveniently located near Lake Oswego's shops, restaurants, parks, and major commuter routes, the home combines a functional floor plan with an exceptional location.

15677 FIELDSTONE DR, Lake Oswego

$5,250,000

4 Beds ⋅ 4 Baths ⋅ 338843522 MLS

Stillwater Vista by TimberRidge Development - A Private Lake Oswego Retreat Above the Water Commanding a premier vantage above Oswego Lake. Stillwater Vista is a rare expression of architectural elegance and effortless lakefront living. Selected for the 2026 Street of Dreams Home Builder Showcase, this residence showcases an exceptional level of design, craftsmanship, and innovation in one of Lake Oswego’s most coveted settings. A dramatic great room features 20-foot vaulted ceilings, statement lighting, and a sculptural fireplace, while walls of glass frame serene lake views and open to a vaulted, covered upper terrace with a striking stone fireplace, integrated heating, and outdoor entertaining spaces. The kitchen is both a showpiece and a professional workspace, defined by exposed beam ceilings, a 12-foot island, side-by-side Sub-Zero refrigeration, and a 60-inch Wolf range, complemented by custom inset cabinetry and a fully equipped scullery. An indoor-outdoor bar enhances seamless entertaining. The main-level primary suite offers 17-foot vaulted ceilings, tranquil water views, and a spa-inspired bath with heated floors, slab marble, a soaking tub, and a custom dressing room with island and integrated laundry. The lower level is designed for leisure, featuring a lounge with fireplace, glass-enclosed wine cellar, fitness studio with sauna, and access to a covered lakeside terrace with hot tub and media setup. Residents enjoy access to Oswego Lake via a private neighborhood tram to a dedicated boat slip—an increasingly rare amenity completing this exceptional offering. Stillwater Vista is a showcase, a retreat, and a legacy property designed to be experienced.

843 TERRACE DR, Lake Oswego

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