About 4399 Glenwood Dr
FINAL OPEN HOUSE SUNDAY (09/20/2026) before the owner takes the property off the market. 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 its 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. Enjoy this versatile property that seamlessly balances premium lifestyle, a prime commuter location & long-term income potential.
Features of 4399 Glenwood Dr
| MLS® # | ML82053482 |
|---|---|
| Price | $1,199,000 |
| Bedrooms | 3 |
| Bathrooms | 2.00 |
| Full Baths | 2 |
| Square Footage | 1,400 |
| Square Footage | Other |
| Acres | 0.40 |
| Year Built | 1993 |
| Type | Single Family Residential |
| Sub-Type | Single Family Home |
| Style | Traditional |
| Status | Active |
Community Information
| Address | 4399 Glenwood Dr |
|---|---|
| Area | Scotts Valley North |
| City | Scotts Valley |
| County | Santa Cruz |
| State | CA |
| Zip Code | 95066 |
Amenities
| Amenities | High Ceiling , Vaulted Ceiling , Walk-in Closet |
|---|---|
| Utilities | Generator, Individual Electric Meters, Propane On Site |
| Parking Spaces | 5 |
| Garages | Off-Street Parking, Uncovered Parking |
| View | Hills, River / Stream, Forest / Woods |
| Is Waterfront | No |
| Has Pool | No |
Interior
| Appliances | Dishwasher, Cooktop - Gas, Hood Over Range, Oven - Self Cleaning, Countertop - Quartz, Refrigerator, Oven - Gas |
|---|---|
| Heating | Heat Pump, Wall Furnace |
| Cooling | Other, Whole House / Attic Fan |
| Fireplace | No |
| # of Stories | 2 |
Exterior
| Lot Description | Stream - Seasonal, Grade - Mostly Level |
|---|---|
| Windows | Low Flow Shower , Low Flow Toilet, Insulation - Floor |
| Roof | Rolled Composition, Shingle, Composition |
| Construction | Wood Frame |
| Foundation | Concrete Perimeter |
Additional Information
| Zoning | RA |
|---|---|
| Foreclosure | No |
| Short Sale | No |
| RE / Bank Owned | No |
Listing Details
| Agent | Lisa Dailey-goodrich |
|---|---|
| Office | Miritz & Bailey Real Estate, Inc |
| Contact Info | 831-325-6320 |