$798,475Average Value$306Average Price per Sq Ft9Homes For Sale
Hillside East is a forested community in the foothills of the Chugach Mountains
Perched on the edge of the Chugach Mountains, Hillside East is a scenic neighborhood in Anchorage. This rural community puts homeowners right next to some of the most popular outdoor spots in the city, including the most-hiked trail in the entire state. Custom homes fill the hilly, tree-lined streets, creating a vibrant blend of architecture throughout the area. Living here feels like an escape into the wilderness, but it’s still just a 5-mile drive to nearby grocery stores and restaurants.
A custom chalet-style home in Hillside East offers views of both the mountains and the city skyline.
Forest views frame dog walkers along the Hilltop Trail Head path.
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Custom-built cabins and Craftsman homes at the base of the mountains
With each switchback in the road going up the hillside, the views get better and better. “It’s kind of like you’re sitting in the cockpit of an airplane,” says Christopher Scott, an associate broker at Jack White Real Estate. “You’re just looking down and can see everything. It’s beautiful.” Most of the houses in the neighborhood are custom-built, often in cabin or Craftsman styles. The area has dense foliage, with a mix of evergreens and leafy trees contributing to its natural feeling. Undeveloped lots are available for buyers who want to build their own home.
Home styles vary from chalet to custom designs.
Homes in the neighborhood come in a variety of styles that complement the natural surroundings.
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What to pay for a home in Hillside East
Homes in Hillside East come at a premium. “It’s definitely on the higher end in Anchorage. There are some generally affordable homes, but as the lots are larger up there, generally the homes are larger,” Scott says. Houses on lots under 1 acre range from the mid-$500,000s to the mid-$900,000s. Properties over 1 acre cost between the mid-$700,000s and the lower $2,000,000 range. Undeveloped lots can cost between the low $100,000s and mid-$300,000s. Almost every property is on a well and septic system, so you can save some money by not having a monthly water bill.
Popular hiking trails are right next door
The Chugach Mountains sit just east of the neighborhood, offering lots of recreation. The Glen Alps/Flattop Trailhead is the starting point to hike to Flattop Mountain, Alaska’s most visited peak. The 1.5-mile trail typically takes about an hour to reach and rewards hikers with panoramic views. The trailhead is also a jumping-off point to reach spots like the Williwaw Lakes and Little O’Malley Peak. Nearby Far North Bicentennial Park has 4,000 acres to explore by hiking, biking or cross-country skiing. Downhill skiers of all levels can enjoy some time at the Hilltop Ski Area, which has 30 acres of slopes and offers private and group lessons.
Prospect Heights Trailhead sits at the edge of hillside trails used for daily workouts.
A paraglider launches off Flattop Mountain at the Glen Alps Trailhead.
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Highly rated schools offer a wide variety of academic programs
Students in Hillside East might attend either the top-rated South Anchorage High School or the highly rated Service High School. South Anchorage High School has civic leadership and engineering programs, plus an Air Force JROTC chapter. Students at Service High have multiple academies to choose from:
Academy of Health & Human Services
Academy of Industry & Innovation
Biomedical Career Academy
Navy JROTC Leadership Academy
Your children are the highest priority at O'Malley Elementary School.
O'Malley Elementary School offers an encouraging environment for children to thrive in.
Hanshew Middle School is home to the Hawks.
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What kind of commute to expect in Hillside East
Because of its isolated location, Hillside East is a car-dependent neighborhood. There is no public transit in the area, but major thoroughfares connect to the rest of the city. O’Malley Road leads west to Seward Highway for a 12-mile drive into Downtown Anchorage, which typically takes about 20 minutes. Abbott Road and Huffman Road also lead west toward the city.
Grocery stores and popular restaurants are a short drive away
South Anchorage has a thriving commercial area, so you don’t have to drive all the way downtown for shopping and dining.
You can stock up on groceries at the Carrs on Huffman Road, about 5 miles away.
The Dimond Center and Walmart offer more shopping near the intersection of Dimond Boulevard and Old Seward Highway.
Head to South Restaurant + Coffeehouse for brunch or make a dinner reservation at Suite 100 for steak and seafood.
Swing by the drive-thru at Wee B’s for an elk or buffalo burger from this longstanding local favorite.
Dimond Center includes several national retailers, including a Best Buy.
Costco on Dimond Boulevard is a short drive from the community.
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How to deal with wildlife encounters in the Alaskan wilderness
Living in Hillside East means you’ll be face-to-face with nature on a daily basis. “You get to experience living at the foot of the Chugach Mountains, and it’s a common experience to see Alaskan wildlife in your yard, like Moose, bears and lynx. So those are special to see, and pretty common,” Scott says. While the animals can be a majestic sight, it’s important to stay safe. Common practices include keeping trash inside to prevent animals from rummaging through it. When you’re out on the trails, make lots of noise so you don’t catch a bear off guard, and always carry bear spray.
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Hillside East Demographics and Home Trends
On average, homes in Hillside East, Anchorage sell after 24 days on the market compared to the national average of 55 days. The median sale price for homes in Hillside East, Anchorage over the last 12 months is $880,000, up 10% from the median home sale price over the previous 12 months.
Surrounded by thoughtfully designed gardens and mature landscaping, this property offers an extraordinary outdoor experience. Multiple seating areas, walking paths, raised garden beds and abundant seasonal blooms complement the panoramic views of Mt. Susitna, Cook Inlet, and downtown. Wildlife is commonly observed on the property, offering a true AK experience throughout the changing seasons.
Welcome to your own exclusive homesite at the end of a privately maintained cul-de-sac. Enjoy panoramic views of the inlet and surrounding mountains, an ideal backdrop for your custom-built home. A rare blend of luxury and natural beauty high above Anchorage, find tranquility and serenity with Potter Highlands Walking Trail just outside your future doorstep.
Horse Property wonderful views overlooking Anchorage, the inlet, Sleeping Lady & often Mt. St Augustine to Mt Mckinley. 3.41 Acre hillside estate near Chugach State Park. Multigenerational home with 5 bedrooms, 5 full baths. Master suite on third floor has vaulted ceilings, huge walk-in closet, jacuzzi & large shower. New Roof just installed. The heated barn could also be used as a garage or shop
WHERE ALASKA'S WILDERNESS MEETS REFINED LIVING! Privately nestled on approximately 2.25 acres bordering Chugach State Park, this extraordinary custom Hillside estate captures panoramic views of the Chugach Mountains, Cook Inlet, city lights, Denali, and the Northern Lights. Exceptional craftsmanship, luxury amenities, and unmatched tranquility. See Supplemental Remarks for full estate details.
Welcome to your own exclusive homesite that offers a rare blend of luxury and natural beauty. Enjoy the serenity of a privately maintained cul-de-sac with panoramic views of the inlet and surrounding mountains, an ideal backdrop for your custom-built home. Find tranquility and daily connection to nature with Potter Highlands Walking Trail just outside your future doorstep.
Welcome to 9900 Hillhaven Circle, one of Alaska's most exquisite estates! Nestled against the backdrop of the majestic Chugach Mountains and surrounded by pristine wilderness, this extraordinary residence stretches 19,300 square feet on 4.5 acres and offers a rare combination of privacy, luxury, and natural beauty. Thoughtfully designed to harmonize with its surroundings, the estate features
Discover the perfect canvas for your Alaskan dream home on this rare Hillside East 2+ acre lot! Tucked away at the end of the road with nothrough traffic, this property offers peace, privacy, and the ultimate sense of seclusion while still being close to amenities and miles of trails. Surrounded by mature trees, you'll enjoy a natural setting with plenty of room to design your ideal retreat.An
Very unique opportunity on Anchorage's Hillside! Situated on just over an acre, this one-of-a-kind octagon-shaped home offers distinctive architecture and endless potential. Featuring 3 bedrooms plus an office, a wood-burning fireplace, and a spacious detached 2-car garage, the property provides plenty of room to live, work, and create. Extensive landscaping surrounds the home, adding character
Rare opportunity in a desirable Hillside neighborhood! This 4,000+ SF home sits on 1.17 acres and offers abundant space, distinctive character, and a layout suited for an ADU or in-law suite. Includes a 630 SF detached garage/shop and a recently replaced roof. Sold as-is and in need of substantial work--ideal for a capable buyer ready to take on a large project.
Welcome to your own exclusive acre and a half homesite that offers a rare blend of luxury and natural beauty. Bordering open space for privacy, you can enjoy the serenity of a privately maintained cul-de-sac with panoramic views of the inlet and surrounding mountains, an ideal backdrop for your custom-built home. Find tranquility and daily connection to nature with Potter Highlands Walking Trail
Welcome to your own exclusive homesite on a privately maintained cul-de-sac, offering a rare blend of luxury and natural beauty high above Anchorage. Backing to open space, enjoy the peaceful views of the mountains and inlet, an ideal backdrop for your custom-built home. Find serenity or outdoor adventure with Potter Highlands Walking Trail just outside your doorstep.
Perched on a sunny corner lot with Wolverine Peak and Rabbit Creek Valley as your backdrop, this home is made for those who crave adventure and comfort. Minutes to backcountry trails, then come home to sunshine that floods the living area all year - morning alpenglow over the mountains, evening light painting the sky. Open kitchen and living areas framed by windows, designed for gathering and
Big views, room to breathe, and Flattop just minutes away. This 3 bedroom, 2.5 bath Hillside home sits on 1.88 acres with wide open views of Cook Inlet, city lights, mountains, and Alaska sunsets. Inside, enjoy 2,718 square feet, radiant heat, a fireplace, and plenty of space to spread out. Private and peaceful, yet still close to town. Some homes have a view. This one has the whole Anchorage
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