Discover the perfect blend of mountain serenity and everyday convenience at this exceptional dual-residence property on the border of Scotts Valley and Los Gatos in the coveted Santa Cruz Mountains. Surrounded by natural beauty, 4399 Glenwood Drive is a meticulously maintained and thoughtfully updated 3 bedroom, 2 bath home offering +-1400 SF of warm, inviting living space. Set within a fully fenced private oasis, the home combines peaceful seclusion with effortless access to Highway 17, placing Santa Cruz beaches and Silicon Valley employment hubs just minutes away. Privately positioned behind the main residence on its own private right of way, 4401 Glenwood Drive is a charming updated 1 bedroom, 1 bath, +-530 SF second home. Ideal for rental income, multi-generational living or guests, this fully independent unit offers exceptional flexibility and long-term value. The homes share a well and whole house generator, while each residence maintains its own parcel, septic system, and PG&E meters providing both autonomy and convenience. Enjoy tranquil wooded surroundings, open pastures and views of a seasonal creek from this peaceful and versatile property--an opportunity that seamlessly blends lifestyle, location and income potential.
MLS #
ML82037469
MLS Source
MLSListings, Inc.
Days on Site
4
Bedrooms
Ground Floor Bedroom, Primary Bedroom on Ground Floor
Bathrooms
Primary - Stall Shower(s), Shower over Tub - 1, Tile, Updated Bath(s), Full on Ground Floor
Appliances
Cooktop - Gas, Dishwasher, Hood Over Range, Oven - Gas, Oven - Self Cleaning, Refrigerator, Washer/Dryer
Dining Room
Dining Area
Family Room
No Family Room
Flooring
Carpet, Wood
Cooling
Other, Whole House Fan
Heating
Wall Furnace
Roof
Composition, Rolled/Hot Mop, Shingle
Foundation
Concrete Perimeter
Style
Traditional
Garage/Parking
Off-Street Parking, Garage: 0 Car(s)
Elementary District
Scotts Valley Unified
High School District
Scotts Valley Unified
Sewer
Septic Tank
Water
Well
Zoning
RA
4399 Glenwood Dr is a Single Family Residence in Scotts Valley, CA 95066. This 1,400 square foot property sits on a 0.4 Acres Lot and features 3 bedrooms & 2 full bathrooms. It is currently priced at $1,299,000 and was built in 1993. This address can also be written as 4399 Glenwood Dr, Scotts Valley, CA 95066.
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This listing information is up-to-date as of March 09, 2026. For the most current information, please contact Lisa Dailey-goodrich, (831) 325-6320