




23594 Hillside Dr, Crestline, CA, 92325
About This Home
Up in the hills of a sweet mountain town named Crestline, you'll find Hillside House, a thoughtfully curated boutique retreat created for reconnecting and escaping the everyday. This beloved couples getaway has earned a devoted following, an exceptional reputation, and recognition as a top-performing Airbnb property. On the main level, imagine cozy evenings by the fireplace, surrounded by books and music. Upstairs, the oversized bedroom becomes its own retreat with a romantic clawfoot soaking tub, custom mural, and a serene atmosphere made for unwinding. Step outside to discover multiple outdoor spaces to listen to the birds or dive into that novel you can't put down. Imagine morning coffee on the deck, dinners beneath the trees and starlit evenings soaking in the very private backyard hot tub. Beyond the beauty, Hillside House offers a rare opportunity to acquire an established, turnkey short-term rental with a recognizable identity and loyal following. Every detail has been intentionally curated, allowing the next owner to step directly into a successful mountain hospitality experience. Hillside House captures the best of Crestline living — affordable mountain charm just a short drive from Los Angeles. A rare chance to own not just a cabin, but a destination. Financials available upon request. Property has an active San Bernardino County STR permit.
Getting Around
Schools
Construction
Condition
- Year built: 1989
Type & Style
- Home type: SingleFamily
- Property subType: Single Family Residence
Interior
Appliances
- Appliances included: Dishwasher,Gas Range,Refrigerator,Water Heater,Dryer,Washer
Bathroom
- Features: Tub Shower
Bedroom
- Features: All Bedrooms Up
Bedrooms & Bathrooms
- Bedrooms: 1
- Bathrooms: 2
- Full bathrooms: 1
- 1/2 bathrooms: 1
- Main level bathrooms: 1
Features
- Beamed Ceilings,Balcony,Tile Counters,All Bedrooms Up
- Fireplace features: Gas,Living Room
- Fireplace: Yes
- Common walls with other units/homes: No Common Walls
Heating & Cooling
- Heating features: Central
- Cooling features: Ductless
Interior Area
- Total interior livable area: 816 sqft
Kitchen
- Features: Tile Counters
Property
Accessibility
- Accessibility features: None
Details
- Parcel number: 0338043640000
- Special condition: Standard
Features
- Levels: Two
- Stories: 2
- Entry location: 2
- Pool features: None
- Patio & porch: Deck
- Has spa: Yes
- Spa features: Above Ground
- Has view: Yes
- View description: Trees/Woods
Lot
- Lot size: 3,740 sqft
- Features: Back Yard
Parking
- Total spaces: 2
- Parking features: Driveway,Garage
- Has garage: Yes
- Attached garage spaces: 2
- Covered spaces: 2
Climate Risk is Financial Risk
Every home has a financial story beyond the listing price. Below, you’ll see the climate risks that could affect this property — and in Bills & Affordability, how those risks may influence repairs, insurance, utilities, and long-term value.
Biggest Threats for This Home
- Wildfire
- Earthquake
- Heat Wave
- Landslide
How This Home’s Risks Compare
FEMA Declared Disasters in San Bernardino County and California
Understanding the Costs
Financial advisors generally recommend spending no more than 30% of your gross household income on housing costs. In practice, many households stretch to 35% or beyond — especially in high-cost markets.
Estimated Costs Today
| Monthly | Annual | |
|---|---|---|
| Mortgage | $1,714 | $20,568 |
| Home Insurance * | $167 | $2,004 |
| Property Taxes | $368 | $4,416 |
| Electricity | $398 | $4,786 |
| Total | $2,647 | $31,764 |
Income You'd Need if You Spent...
California FAIR Plan Programs
How Costs Could Change Over Time
Climate risk is quickly impacting all of the major home ownership costs. Adjust the growth rates and percentage of income spent on housing below to see how your housing costs could change over the next 10 years — and what income you'd need to keep up.
Comparing Against the Market
Price Per Sq Ft
vs Other Active Listings
Avg $/sqft
vs Homes Sold Last Month
Median $/sqft
Current Market Trends
Median Price Per Square Foot
The median price per square foot of homes sold in this area each month. Compare this to this listing's price per square foot to gauge whether the home is priced in line with recent sales.
Historicals for This Listing
Zestimate History ($/sqft)
Price History
| Date | Event | Price |
|---|---|---|
| 2026-07-21 | Listed for sale | $339,000 |
| 2026-01-11 | Listing removed | $350,000 |
| 2025-06-23 | Listed for sale | $375,000 |
| 2021-06-24 | Sold | $280,000 |
| 2021-06-16 | Pending sale | $275,000 |
| 2016-09-20 | Listing removed | $176,000 |
| 2016-07-16 | Listed for sale | $176,000 |
| 2005-12-30 | Sold | $236,500 |
| 2004-09-23 | Sold | $185,000 |
| 2003-01-09 | Sold | $137,500 |
| 2001-07-23 | Sold | $124,500 |
| 2000-02-14 | Sold | $104,000 |
| 1996-10-31 | Sold | $102,000 |
