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Shawn Bengtson

Office Broker - DRE 01236964

  • Office 760-805-7199
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4399 Glenwood Drive, Scotts Valley – $1,299,000

  • 3 Beds
  • 2 Baths
  • 1,400 Sqft
  • .4 Acres
  • 3 Beds
  • 2 Baths
  • 1,400 Sqft
  • .4 Acres

4399 Glenwood Drive

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.

Essential Information

  • MLS® #ML82037469
  • Price$1,299,000
  • Bedrooms3
  • Bathrooms2.00
  • Full Baths2
  • Square Footage1,400
  • Acres0.40
  • Year Built1993
  • TypeResidential
  • Sub-TypeSingle Family Residence
  • StyleTraditional
  • StatusActive

Community Information

  • Address4399 Glenwood Drive
  • Area699 - Not Defined
  • CityScotts Valley
  • CountySanta Cruz
  • Zip Code95066

Amenities

  • Parking Spaces5
  • ParkingOff Street, Uncovered
  • GaragesOff Street, Uncovered
  • ViewHills, Trees/Woods, River

Interior

  • InteriorCarpet, Wood
  • Interior FeaturesLoft
  • HeatingWall Furnace
  • CoolingWhole House Fan
  • # of Stories2

Appliances

Dishwasher, Gas Cooktop, Gas Oven, Refrigerator, Range Hood, Self Cleaning Oven

Exterior

  • RoofComposition, Shingle
  • FoundationConcrete Perimeter

School Information

  • DistrictOther
  • ElementaryOther
  • MiddleScotts Valley
  • HighOther

Additional Information

  • Date ListedMarch 6th, 2026
  • Days on Market12
  • ZoningRA

Listing Details

  • AgentLisa Dailey-goodrich

Office

Miritz & Bailey Real Estate, Inc

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Lisa Dailey-goodrich, Miritz & Bailey Real Estate, Inc.

Based on information from California Regional Multiple Listing Service, Inc. as of March 18th, 2026 at 12:55am PDT. This information is for your personal, non-commercial use and may not be used for any purpose other than to identify prospective properties you may be interested in purchasing. Display of MLS data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and should investigate the data themselves or retain appropriate professionals. Information from sources other than the Listing Agent may have been included in the MLS data. Unless otherwise specified in writing, Broker/Agent has not and will not verify any information obtained from other sources. The Broker/Agent providing the information contained herein may or may not have been the Listing and/or Selling Agent.