Living in Smiley Heights, Redlands
Smiley Heights is the hillside neighborhood on Redlands’ south side, built on the land where the Smiley brothers once ran Cañon Crest Park, one of Southern California’s most famous gardens. Today it’s known for custom and mid-century homes on larger lots, winding streets, and views across the valley to the San Bernardino Mountains. Prospect Park and Kimberly Crest sit right next door, and downtown is a short drive down the hill.
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Smiley Heights at a glance
| Best for | Buyers who want space, privacy, and views close to central Redlands |
|---|---|
| Home styles | Mid-century homes and custom builds, many on larger hillside lots |
| Setting | Winding, tree-lined hillside streets on the south side of the city |
| Nearby | Prospect Park, Kimberly Crest, Sunset Drive, downtown Redlands |
| Median price | [UPDATE MONTHLY FROM MLS] |
| Average days on market | [UPDATE MONTHLY FROM MLS] |
What it's like to live in Smiley Heights
Smiley Heights is quiet and residential. There’s no commercial strip inside the neighborhood, so daily life is about the house, the yard, and the view. Streets curve with the hillside, many homes sit back from the road behind mature trees, and evenings are dark and still compared with the valley floor.
You’re still close to everything. Downtown Redlands, the University of Redlands, and I-10 are a short drive away, and Prospect Park’s shaded trails are within walking distance for much of the neighborhood.
From Cañon Crest Park to Smiley Heights
In 1889, twin brothers Albert and Alfred Smiley, the New York hoteliers behind Mohonk Mountain House, bought about 200 acres of the heights south of Redlands for their winter homes. They built carriage roads and walking paths, planted rare trees and flowers from around the world, and opened the grounds to the public as Cañon Crest Park.
The park drew thousands of tourists every year and helped put Redlands on the map. Both brothers died in Redlands, Alfred in 1903 and Albert in 1912. By the mid-20th century the park had given way to residential development, and the hills became the neighborhood we know today. Losing Cañon Crest Park is one reason Redlands fought to save neighboring Prospect Park in the 1960s.
Homes in Smiley Heights
Most homes here were built from the mid-20th century onward, which makes Smiley Heights very different from the Victorian and Craftsman streets near downtown. Expect single-story mid-century ranch homes, larger custom homes from later decades, and lots that are generous by Redlands standards.
What buyers should know about hillside homes
- Check the fire hazard disclosure. Some hillside areas in the region fall within designated fire hazard severity zones. Review the Natural Hazard Disclosure and get insurance quotes early in escrow.
- Look at drainage and slope. Ask your inspector to review grading, retaining walls, and how water moves across the lot.
- Views can be protected or not. Ask what could be built below or beside the property, and whether trees on neighboring lots might grow into the view.
- Mid-century systems age too. Original plumbing, electrical panels, and roofs on 1950s and 1960s homes deserve a close look.
Nearby parks and landmarks
- Prospect Park. A 39-acre park of tree-shaded trails bought by the city in 1968, and home to the outdoor Redlands Theatre Festival.
- Kimberly Crest House and Gardens. An 1897 château-style mansion with terraced Italian gardens at 1325 Prospect Drive, on the National Register and open for tours.
- Sunset Drive. A scenic route along the south Redlands hills, popular with walkers and cyclists.
- Downtown Redlands. State Street, Smiley Library, and the Redlands Bowl are a short drive down the hill.
Smiley Heights real estate market
[ADD 2–3 SENTENCES MONTHLY: median sale price, price per square foot, days on market, and active listings for Smiley Heights, with the month and source. Smiley Heights often sees few sales a month, so a 6- or 12-month figure may be more meaningful.]
A strong fit if you want
A larger lot, privacy, valley and mountain views, and a quiet street that’s still minutes from downtown.
Think it through if you need
Walkability to shops, a lower price point, a home with no hillside upkeep, or easy insurance. Listings are limited and turn over slowly.
Why buy or sell in Smiley Heights with Leo
I’m Leo Dominguez, a Redlands REALTOR® with Len Group Redlands at Keller Williams, and I teach at the University of Redlands. Homes in Smiley Heights are one of a kind, so pricing them takes local judgment, not just an online estimate. My background in digital marketing means sellers get a listing presented like the special property it is, and buyers get someone who watches the neighborhood closely for the rare home that fits.
Smiley Heights FAQ
Where is Smiley Heights in Redlands?
Smiley Heights is on the hills of Redlands’ south side, near Prospect Park and Kimberly Crest, a short drive from downtown.
Why is it called Smiley Heights?
It’s named for Albert and Alfred Smiley, who created Cañon Crest Park on these hills in the 1890s. The park was known to the public as Smiley Heights.
What kinds of homes are in Smiley Heights?
Mostly mid-century homes and larger custom homes, many on bigger hillside lots with views of the valley and the San Bernardino Mountains.
Is homeowners insurance harder to get in Smiley Heights?
It can take more shopping. Hillside homes may sit in a fire hazard zone, so review the hazard disclosure and get quotes early in escrow.
Thinking about Smiley Heights?
Whether you’re looking for the right hillside home or getting ready to sell one, let’s talk about what your street is worth today.
Len Group Redlands – Keller Williams Redlands | DRE #02167691 | [PHONE]
STEP 1
CHOOSE TO BUY OR SELL A HOME.
During our phone call, we’ll introduce you to our customized real estate buying and selling process, crafted to alleviate your concerns and streamline your experience
STEP 2
GET A CUSTOM BUY OR SELL PLAN.
We will create a tailored plan for your home buying or selling journey, ensuring you make a well-informed financial decision that aligns with your family’s needs and timeline.
STEP 3
ENJOY PEACE OF MIND.
Our specialized and personal approach is aimed at reducing your worry and stress, enabling you to relax and genuinely enjoy the process of buying or selling your home, free from feeling overwhelmed.