About 4399 Glenwood Drive
TWO HOUSES in rare historic setting overlooking the 1880s Glenwood Train Turnaround & bordering the Glenwood to Wrights rail tunnel! Discover a rare dual-residence opportunity perfectly blending mountain serenity, historic rail heritage & everyday convenience, nestled at the border of Scotts Valley & Los Gatos in the coveted Santa Cruz Mountains. This unique property features 2 fully independent homes surrounded by tranquil wooded views, open pastures & a seasonal creek. 4399 Glenwood Dr is a meticulously maintained & updated 3BR/2BA sanctuary offering 1400 SF of warm living space. The home sits within a fully fenced, private oasis combining peaceful seclusion with effortless access to Highway 17, Santa Cruz beaches & Silicon Valley employment hubs. 4401 Glenwood Dr is tucked privately behind the main house on it's own private right of way. This updated 1BR/1BA, 530 SF home serves as an ideal source for rental income, multi-generational living, or guest accommodations. While the residences share a private well & whole-house backup generator, they provide complete independence with separate parcels, individual septic systems, & dedicated PG&E meters. Enjoy this versatile property that seamlessly balances premium lifestyle, a prime commuter location & long-term income potential.
Open House
Features of 4399 Glenwood Drive
| MLS® # | ML82053482 |
|---|---|
| Price | $1,199,000 |
| Bedrooms | 3 |
| Bathrooms | 2.00 |
| Full Baths | 2 |
| Square Footage | 1,400 |
| Acres | 0.40 |
| Year Built | 1993 |
| Type | Residential |
| Sub-Type | Single Family Residence |
| Style | Traditional |
| Status | Active |
Community Information
| Address | 4399 Glenwood Drive |
|---|---|
| Area | 699 - Not Defined |
| City | Scotts Valley |
| County | Santa Cruz |
| Zip Code | 95066 |
Amenities
| Parking Spaces | 5 |
|---|---|
| Parking | Off Street, Uncovered |
| Garages | Off Street, Uncovered |
| View | Hills, Trees/Woods, River |
| Is Waterfront | No |
| Has Pool | No |
Interior
| Interior | Carpet, Laminate, Tile, Wood |
|---|---|
| Interior Features | Loft |
| Appliances | Dishwasher, Gas Cooktop, Gas Oven, Refrigerator, Range Hood, Self Cleaning Oven |
| Heating | Heat Pump, Wall Furnace |
| Cooling | Whole House Fan |
| Has Basement | No |
| Fireplace | No |
| # of Stories | 2 |
Exterior
| Roof | Composition, Shingle |
|---|---|
| Foundation | Concrete Perimeter |
School Information
| District | Other |
|---|---|
| Elementary | Other |
| Middle | Scotts Valley |
| High | Other |
Additional Information
| Date Listed | July 8th, 2026 |
|---|---|
| Days on Market | 73 |
| Zoning | RA |
| Foreclosure | No |
| Short Sale | No |
| RE / Bank Owned | No |
Listing Details
| Agent | Lisa Dailey-goodrich |
|---|---|
| Office | Miritz & Bailey Real Estate, Inc |