Lake Oswego Homes with Private Road Lot description

Welcome to Lake Oswego, Oregon—a picturesque gem nestled in Clackamas County that perfectly blends suburban charm with urban convenience. Just a short drive from downtown Portland, this vibrant city is renowned for its stunning lake views, lush green spaces, and a strong sense of community. With a rich history dating back to the 1800s, Lake Oswego boasts a unique blend of modern amenities and historic charm, making it an ideal place to call home.

One of the most alluring aspects of Lake Oswego is its diverse array of real estate options, particularly homes situated on private roads. These exclusive properties offer a sense of tranquility and privacy, allowing residents to enjoy serene surroundings while still being close to the heart of the city. Imagine waking up to the gentle sounds of nature, with beautifully landscaped yards and the added benefit of reduced traffic and noise. Homes on private roads often feature spacious lots, providing ample outdoor space for families, pets, and entertaining.

The community is known for its top-rated schools, vibrant local culture, and an abundance of recreational activities, including hiking, boating, and dining along the scenic waterfront. With a delightful mix of boutique shops, art galleries, and gourmet restaurants, Lake Oswego offers a lifestyle that is both relaxed and sophisticated. Whether you’re looking for a cozy retreat or a spacious family home, the charm of Lake Oswego’s private road residences promises a peaceful and fulfilling living experience. Discover your dream home in this enchanting city today!

Newest Lake Oswego Homes with Private Road Lot description

$425,000

514508418 MLS

Exceptional Opportunity in One of Lake Oswego’s Most Coveted Neighborhoods – This rare .32-acre lot offers the perfect canvas for your custom home, nestled in a tranquil, park-like setting just off street level for privacy and easy driveway access. Enjoy peek-a-boo views of Lake Oswego from the homesite, with all property corners marked and utilities available at both Westview Drive and South Shore Blvd to streamline development. Stakes outlining the buildable footprint are visible from the private driveway entrance. Exclusive lake easement rights provide access to Maple Circle, Alder Point Club, Blue Heron, and Lakeview Recreation Club—offering boat slips, kayak/paddleboard storage, and year-round recreational opportunities. Ideally located near top-rated schools, scenic parks, and upscale shopping and dining, this property blends natural beauty, privacy, and premier amenities. MLS#556564395 includes a proposed build plan inspired by Frank Lloyd Wright to help you visualize the possibilities. Buyer to perform their own due diligence.

17035 WESTVIEW DR, Lake Oswego

$550,000

2 Beds ⋅ 2 Baths ⋅ 127388334 MLS

Welcome to this well-maintained one level home in the Woodside community of Lake Oswego, featuring vaulted ceilings, skylights, laminate wood flooring, and tile flooring in the kitchen, dining room, and bathrooms. The living room features a wood-burning fireplace, while the kitchen includes a built-in oven, dishwasher, disposal, and eating area. Sliding doors open to a private, fully fenced patio and yard with a level setting and established garden. The primary bedroom includes a closet organizer and private bathroom; a second bedroom and full bathroom complete the home. A detached two-car garage provides additional parking and storage. Woodside residents have access to a common area with lake access, tennis courts, trails, and a pool. The combination of a one level layout, private outdoor space, detached garage, and Woodside amenities makes this a home worth seeing.

4238 WOODSIDE CIR, Lake Oswego

$2,249,000

5 Beds ⋅ 4 Baths ⋅ 162770319 MLS

Positioned down a private drive at the end of a quiet cul-de-sac in Lake Oswego's Palisades neighborhood, this custom-built contemporary home offers bright, open spaces and serene valley views. A soaring foyer leads into a light-filled great room, where sliding doors open to the main-level deck. The main floor's 3,053 square feet flow from the living room through a formal dining room to a chef's kitchen at the heart of the home, where an expansive island with quartz counters anchors a full suite of built-in appliances, complemented by a spacious walk-in pantry and built-in bar. Wide planked oak floors run throughout the main living spaces, and a bonus room off the foyer is a perfect work-from-home zone. The main-level primary suite is a true retreat, with walk-in closet fitted with custom organizers and a spa-inspired bath featuring a soaking tub, walk-in shower, double vanities, and heated tile floors. A separate wing on the opposite side of the main floor functions as a private guest suite with spacious en-suite bedroom with full-bath, and the laundry room. Downstairs, 1,376 square feet of additional living space centers on a spacious family room that opens to its own deck, creating a second full outdoor entertaining zone. Two additional en-suite bedrooms round out the lower level. Enjoy abundant storage throughout the home including an unfinished 32-by-17-foot storage space, which could readily become the perfect wine cellar. Enjoy the wooded trails of Cooks Butte Park, eligibility for Greentree Pool, and a quick drive to downtown Lake Oswego's shops and restaurants, served by top LOSD schools: Hallinan Elementary, Lakeridge Middle, and Lakeridge High.

1921 MAPLELEAF CT, Lake Oswego

$799,900

4 Beds ⋅ 3 Baths ⋅ 699376747 MLS

OPEN HOUSE SUN SEPT 6, 11am-1pm! Don't miss this one! Major systems in good form. Enjoy the heart of Lake Oswego in this spacious 4-bedroom, 3-bath Glenmorrie home! New carpet, a fully remodeled kitchen with cherry hardwood floors, granite countertops, stainless steel appliances, and ample storage are just the beginning. At .35-acres, this property offers exceptional space to accommodate hobbies, recreation, and entertaining. The 32' x 22' RV pad with hookups provides room for your RV, boat, or additional vehicles/equipment. Generator housed in Zombie box. 16' x 12' storage shed. Major systems are newer + Roof (2018), Windows (2022), Pool Deck (2025), Pool Heater and Filter (2025), Exterior Paint (2022), Beauftiful Kitchen Remodel (2018), New Entry door and Garage Door (2017), Generator (2022), Fencing (2025), Carpet (2026), Paint (2026).NO HOA. Fully fenced backyard, ample deck space, multiple areas for outdoor dining, relaxation, and gatherings. The pool is summer-season ready, making this property an ideal setting for entertaining. All kitchen appliances are included, along with the wine refrigerator, mini-refrigerator, washer and dryer. Conveniently located with quick access to George Rogers Park, shopping, dining, commuting routes, and everything Lake Oswego!

2360 GLENMORRIE DR, Lake Oswego

$3,295,000

5 Beds ⋅ 5 Baths ⋅ 191552232 MLS

Experience luxury lakefront living at its finest on Oswego Lake. This extensively remodeled estate offers over 6,300 square feet of living space, breathtaking elevated lake views, and a fully independent lower-level apartment ideal for multi-generational living, guests, or Airbnb potential. Positioned on the quiet south side of the lake, this rare just under one-acre property offers exceptional privacy, minimal traffic, and panoramic views high above the water.Step inside to soaring ceilings and expansive windows that flood the home with natural light while framing picturesque lake views throughout. Beautiful solid oak floors guide you through the formal living / dining rooms, enhanced with custom lighting, built-ins, a wood-burning fireplace, and past a private home office with French doors. The spacious family room is designed for entertaining with a full wet bar and an additional fireplace. The chef’s kitchen features custom cabinetry, a sprawling quartz island, abundant storage, double dishwashers, and Thermador appliances.An expansive Trex deck extends off the main level, creating the perfect space to relax or entertain while enjoying sweeping lake views. Upstairs, the luxurious primary suite offers heated floors, dual vanities, a soaking tub, glass walk-in shower for two, and a generous custom walk-in closet with built-ins. Two additional en-suite bedrooms, an over-sized bonus room, and ample storage complete the upper level.The fully self-contained lower level includes exterior access, two bedrooms, two full bathrooms, a full kitchen, living area with fireplace, and private Trex deck overlooking the lake. Outside, follow your private stairway down to a boathouse with lift, paddle board storage, and rooftop deck offering direct lake access. A rare opportunity to own an exceptionally expansive and fully remodeled lakefront estate with unmatched privacy, flexibility, and views.

1949 CEDAR CT, Lake Oswego

$2,295,000

4 Beds ⋅ 3 Baths ⋅ 301876751 MLS

Open Sat 8/22 2-4pm! Nestled among the trees on a 3.5 acre lot in Lake Oswego's prestigious Skyland neighborhood. It's European inspired style gives a sense of grandeur, luxury, and ultimate privacy. Tucked up along the hillside, you will enjoy jaw-dropping views all year long. This home is an entertainer's dream with a pool, game room, 3-car garage, 200 bottle wine cellar, multiple wrap around decks, four custom water features and much, much more. Sweeping views of Mt.Hood, Mt.St Helens, Mt.Adams, and the Willamette River. The living room features vaulted ceilings and and a stately gas fireplace. Recent updates include carpet, rebuilt furnaces with smart thermostats, refurbished deck, freshly trimmed trees, new lighting in bedrooms, and much more! Although this home has 3 stories, it has main-floor living with the kitchen, laundry room, primary suite, guest room, and additional full bathroom all on the main level.

1777 SKYLAND DR, Lake Oswego

$4,450,000

5 Beds ⋅ 4 Baths ⋅ 636450776 MLS

Set at the end of a long, gated, and fully paved private drive in the coveted Stafford belt, this nearly 5-acre compound offers something the Lake Oswego market rarely delivers: genuine privacy at this scale, without any sacrifice of proximity.The primary residence has been beautifully remodeled, balancing refined, modern finishes with the warmth of a world-class estate. Custom millwork, Italian tile, high-end fixtures, and a luxurious Thermador kitchen anchor the heart of the home, which opens to a resort-caliber outdoor sanctuary. The fully rebuilt pool, expansive paverscape, gazebo with fire pit, and freestanding hot tub frame the outdoor lifestyle.A standalone guest house, adjacent to the pool, operates on its own gas and electric lines and serves guests or multi-generational living with ease. A professional 4-stall horse barn with tack room, round pen, and manicured pastures completes one of the most compelling horse properties to come to market in Lake Oswego.Approximately one mile to Lakeridge High School and just minutes to Lake Oswego dining, shopping, and lake access. The city when you want it, and a quiet, gated retreat when you don't. More than a home. A sanctuary and a legacy. Request a copy of the expansive updates list.

1925 CHILDS RD, Lake Oswego

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