Milwaukie, Gladstone, Happy Valley, Clckmas, Dmscus, Estacada Real Estate

Welcome to the vibrant communities of Milwaukie, Gladstone, Happy Valley, Clackamas, Damascus, and Estacada in the picturesque state of Oregon! Nestled just southeast of Portland, this region boasts a unique blend of suburban charm, natural beauty, and rich cultural heritage.

Milwaukie, known for its historic downtown and vibrant farmers market, offers a delightful mix of local shops and eateries. Just a stone's throw away, Gladstone is known for its strong sense of community and access to the scenic Willamette River, perfect for outdoor enthusiasts and families alike.

Happy Valley, aptly named for its picturesque views and family-friendly atmosphere, features stunning parks and top-notch schools, making it an ideal spot for those seeking a suburban lifestyle with a touch of nature. Clackamas, with its bustling shopping centers and recreational opportunities, provides a perfect balance of urban convenience and outdoor adventures.

Further southeast lies Damascus, a community that embraces a rural feel while still being close to urban amenities. Residents enjoy spacious properties and a slower pace of life, making it an appealing option for those looking to escape the hustle and bustle.

Finally, Estacada, surrounded by lush forests and the Clackamas River, is a hidden gem for nature lovers and outdoor adventurers. With its charming downtown and welcoming community, it’s a place where you can truly unwind and appreciate the beauty of Oregon.

Whether you’re drawn to the rich history, outdoor activities, or the friendly neighborhoods, this region offers something for everyone. Come explore the diverse lifestyles and opportunities waiting for you in these enchanting Oregon communities!

Newest Listings in Milwaukie, Gladstone, Happy Valley, Clckmas, Dmscus, Estacada

$765,000

4 Beds ⋅ 2 Baths ⋅ 166871491 MLS

Unobstructed views of majestic Mt. Hood and the surrounding valleys define this lovingly maintained 1959 “golden era” home. Perfectly positioned on an oversized corner lot at the end of a tranquil cul-de-sac, it offers exceptional potential for additional development, multi-generational living, flexible use of space—or simply move right in and enjoy it for years to come.Inside, you’ll find gleaming pegged oak plank floors, striking fireplaces, timeless built-ins, and graceful bay windows that bathe the home in natural light. The country kitchen, with its second fireplace and generous island, is ideal for both grand gatherings and intimate dinners, all while showcasing spectacular views. A formal dining room flows onto a covered porch—the perfect spot for morning coffee or alfresco evenings with friends.The extra-deep, oversized garage is a tinkerer’s paradise. A spacious unfinished 20’ x 21’ area offers the opportunity to create additional living space for recreation, hobbies, or multi-generational living. There’s even more storage beyond that, making this an excellent home for creative projects or future expansion.Outside, exquisitely landscaped gardens and a private backyard sanctuary create a serene, almost storybook retreat. Warm, inviting, secluded, and lovingly cared for—brimming with character, romance, and possibility—this truly exceptional home is a must-see.

10065 SE CRESTHILL RD, Happy Valley

$99,900

2 Beds ⋅ 2 Baths ⋅ 185921162 MLS

Check out this charming single-wide manufactured home in Johnson City Mobile Estates! Filled with natural light, this inviting home features a spacious living room, a beautiful kitchen with abundant cabinet and counter space, and a convenient utility room with newer washer/dryer and built-in storage. The primary bedroom includes a private ensuite bathroom, while the second bedroom is located near the guest bathroom, making it ideal for hosting, a home office, or a hobby space. New roof July 2026, along with new interior paint, vinyl windows and backdoor. Monthly space rent is $970 and includes water, sewer, and garbage. All ages are welcome!

16261 SE 79TH AVE, Milwaukie

$674,500

4 Beds ⋅ 3 Baths ⋅ 633846277 MLS

Seclusion and Convenience in desirable Scott Mountain neighborhood. Quiet cul-de-sac, beautiful expansive year-round sunset views, in this solid, well-maintained and updated home. Over 30 years with no smoking or pets. Large open layout living & dining rooms, vaulted ceiling, oak floors (Swedish finish). The huge 4th bedroom includes its own fireplace and wet bar (kitchenette) - a natural guest suite. Don't miss your chance to own this gem, available for the first time in over 30 years. Great year-round views from master bedroom, kitchen, dining room and deck: sunsets valley & hills, city lights, fireworks, too! Updated kitchen, utilities, roof, etc. Bonus room/office. Large garage w/ lots of storage. Large fenced backyard, Shed-10'x12', gated RV parking. No telephone poles or overhead power lines. Low HOA fees & taxes.

10787 SE 96TH CT, Happy Valley

$350,000

3 Beds ⋅ 1 Baths ⋅ 423063696 MLS

Opportunity knocks with this 3-bedroom, 1-bath home in Milwaukie! Whether you're an investor, flipper, or buyer looking to build sweat equity, this property is full of potential. The home features a single-car garage and sits on a spacious, level 0.40-acre lot, offering plenty of room for gardening, outdoor entertaining, future improvements, or possible expansion (buyer to verify).This is a cash-only sale. No sign on the property. Please do not disturb the tenant. Showings are by appointment only. Don't miss this opportunity to unlock the potential of this property in a desirable location. Property sold as-is. Buyer to perform all due diligence.

4618 SE INA AVE, Milwaukie

$47,000

2 Beds ⋅ 2 Baths ⋅ 341274877 MLS

Affordable, move-in ready living in a desirable 55+ community! This light cosmetic fixer features: 2-bedroom, 2-bath, 1,440 square feet of comfortable single-level living. The bright, open floor plan features a spacious kitchen with an island, pantry, abundant cabinetry, and included appliances. The primary suite offers a private bath, while the second bedroom provides flexibility for guests or a home office. Enjoy year-round comfort with a new 2025 installed heat pump, plus the convenience of a dedicated laundry room included. Outside, you'll find a covered deck, tool shed, carport, and low-maintenance yard. Conveniently located near shopping, dining, medical facilities, and freeway access. Buyer must receive park approval.

13640 SE HIGHWAY 212 Unit #18, Clackamas

$630,000

4 Beds ⋅ 2 Baths ⋅ 484440976 MLS

Welcome home to your secluded garden oasis, boasting proximity to both mountain recreation and downtown amenities. The rare combination of flat acreage and ideal location marry here in Damascus. A bright and inviting kitchen opens to your spacious entertaining patio nestled under large trees, meander through your garden and enjoy the fruits along the way. Sit under the established vine covered pergola and enjoy your scenic surroundings. Mature landscaping across the property, berries, apple, pear, fig, & cherry trees. Barn with horse stalls, and workshop for all your maker dreams. Property is fully fenced, French drain from house to road, and roof recently replaced. Primary in basement was living room and is non-conforming. Creek access at property end. Your own slice of paradise

24620 SE SUNSHINE VALLEY RD, Damascus

$782,000

3 Beds ⋅ 1 Baths ⋅ 616994372 MLS

Welcome to this charming ranch style home, situated on **On almost 5 acres** in Estacada. Offering the perfect blend of country living and modern updates, this property is ideal for those looking for space, privacy, and exceptional shop facilities. The home features **updated vinyl windows**, newer flooring, roof replaced in 2016, Has High speed fiber, along with copper plumbing updates. Enjoy outdoor living on the spacious **covered deck**, or relax on the expansive **concrete patio** that wraps around the home, with a large outdoor brick fire pit. The backyard is thoughtfully designed with **raised garden beds**, concrete retaining walls, and plumbing in place for a future automated sprinkler system, including an underground irrigation vault. Two impressive shops make this property stand out. The **24' x 30' AG building** was upgraded with new metal siding and roofing, a concrete floor, and a large concrete walkway connecting it to the patio. The **30' x 44' permitted shop** features **200-amp electrical service**, an insulated ceiling, concrete floors, three insulated roll-up doors, and walls that are nearly fully sheeted. It also includes an enclosed exterior air compressor with interior copper air lines, an insulated room housing the well pressure tank, and updated PEX-A water lines to the home. Whether you're looking for room for hobbies, a home business, or simply a peaceful country retreat with outstanding outbuildings, this versatile property offers endless possibilities just minutes from downtown Estacada.

34911 SE SURFACE RD, Estacada

$654,000

4 Beds ⋅ 3 Baths ⋅ 774325576 MLS

This nicely updated split level home has 4 bedrooms, 3 bathrooms, Kitchen appliances are stainless steel, new gas furnace and hot water heater, Roof is 7 years old, new vinyl flooring throughout, new vinyl double pane windows; On 1 acre with a 20'x20' shop with new roof, 10x20 shed, washer and dryer included, 2 wood burning fireplaces have been re-furbished, large double car garage. 4th bedroom on lower-level non-conforming with free standing closet.

20990 SE HIGHWAY 212, Damascus

$449,000

3 Beds ⋅ 2 Baths ⋅ 146580718 MLS

Great starter home sitting on a flat junior acre in Eagle Creek. This home has been completely updated with great detail and style. New paint throughout. The kitchen and and bathrooms has been fully remodeled with great modern style. The property has been prepped for a 40'x60' shop. This is a great opportunity for someone looking for a great home in the country for an affordable price!

30581 SE HIGHWAY 211, Eagle Creek

$899,900

4 Beds ⋅ 2 Baths ⋅ 754038264 MLS

Welcome home to this beautifully custom-built home featuring soaring ceilings, timeless finishes, and an expansive floor plan. The home is designed for comfortable living and effortless entertaining. Enjoy the convenience of primarily one level living, with everything you need on the main floor, plus a family and bedroom upstairs. At the heart of the home is a generous kitchen, perfect for gathering with family and friends. Complete with a butler's pantry, breakfast bar, cozy dining nook. The easy access to the back patio it's designed for both everyday living and memorable occasions.Gleaming hardwood floors extend throughout the main living areas, while soaring ceilings and an open, thoughtfully designed floor plan create a light-filled, expansive atmosphere that feels both elegant and inviting. Those working from home will appreciate the dedicated office featuring beautiful built-ins.Enjoy added peace of mind with major system updates already completed, including a new furnace(2026), water heater(2025), and roof(2022). Looking for room to grow? The upper level offers flexibility, with plumbing already in place for an additional bathroom and ample space to easily create a fifth bedroom; perfect for evolving needs or added value.Who wouldn’t love the oversized garage which provides abundant space for vehicles, storage, hobbies, or a workshop. Perfect for so many options.Every detail of this beautifully appointed residence has been thoughtfully designed to deliver comfort, style, and enduring quality. An extraordinary place to call home!

10523 SE CHARLOTTE DR, Happy Valley

$1,200,000

4 Beds ⋅ 3 Baths ⋅ 268537834 MLS

Magical private and wooded acre in the heart of Damascus with grand chalet style home and wrap around deck! Listen to the birds as you sip your coffee through the slider off of the magnificent living room space. Windows galore will bring in the natural light and give you a view of all the beautiful nature that surrounds this home. Plenty of room for dual living with upstairs loft and bedroom with bathroom. Main level has one bedroom and a full updated bathroom! Kitchen has newer appliances and eating area and opens up to a formal dining area with slider to the massive deck. Cozy wood burning fireplaces on the main level and lower level. Newer flooring and carpet has been done! Lower level can be used for separate living quarters with a family room, two bedrooms, a full bathroom and utility area. It also has its own entrance! HVAC was updated in 2025 and the roof was completed in 2021, Vinyl windows in 2021. The big ticket items have been done for you! Wood shop is 16x14 and full of memories and projects made with love-you will enjoy the fire pit and space outside for gardening, playing and bbqing. Lovely circular driveway with RV parking and hook up near your 2 car garage and plenty of parking for company. Mature apple, plum and acorn trees for years to come. You do not want to miss this show stopper~ready for loving new owners.

10321 SE EASTMONT DR, Damascus

$1,339,000

3 Beds ⋅ 3 Baths ⋅ 443447606 MLS

Builder's own custom 3 bedroom 3 bath one level located on 9.55 fenced level acres and loaded with amenities-Grand front porch transitions to the spacious foyer and opens to the great room with 11' ceilings, floor to ceiling stone fireplace, built-ins, surround sound, access to the 19'x14' covered patio and expands to the kitchen and dining rooms. Cook's kitchen boasts 40' professional propane range with convection oven, stainless steel appliances, slab granite counters, walk-in pantry, spacious island eating bar and flows seamlessly into the generous dining room with 9' built-in granite accented buffet, hardwood floors and double chandelier. The primary en-suite bedroom features 9' ceilings, spacious bath with tile floor, slab marble double vanity, accessible roll in shower with double shower heads, classic free standing oval tub, heated towel racks, linen closet plus the walk-in closet with organizers. Bountiful amenities include easy care hardwood floors, versatile den/office/bedroom with full bath, desirable mud room off the garage with separate outside entrance, utility room with sink, built-ins and abundant counter space, professionally landscaped yard with sprinklers, paved driveway, 60'x40' 4 stall multi-use barn with attached 60'x24' shop, 20'x12 well house with storage, 20'x24' greenhouse, 60'x100' outdoor arena, 2 fenced pastures with water, complete hook-up for your trailer/motor-home, private gated/paved driveway PLUS propane fueled Generac generator. This property is what dreams are made of...call today for your private showing.

41055 SE KITZMILLER RD, Eagle Creek

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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.