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4399 Glenwood Drive, 
Scotts Valley, CA 95066

$1,299,000

3

Beds

2

Baths

1,400

Sq Ft

Single Family

Virtual Tour

Active

Listed by

Lisa Dailey-Goodrich

Miritz & Bailey Real Estate, Inc

lisadaileygoodrich@gmail.com

Last updated:

May 1, 2026, 02:33 PM

MLS#

ML82037469

Source:

Bay East CCAR bridgeMLS

About This Home

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.

Home Facts

Single Family

2 Baths

3 Bedrooms

Built in 1993

Price Summary

1,299,000

$927 per Sq. Ft.

MLS #:

ML82037469

Last Updated:

May 1, 2026, 02:33 PM

Added:

1 month(s) ago

Rooms & Interior

Bedrooms

Total Bedrooms:

3

Bathrooms

Total Bathrooms:

2

Full Bathrooms:

2

Interior

Living Area:

1,400 Sq. Ft.

Structure

Structure

Architectural Style:

Single Family Residence, Traditional

Building Area:

1,400 Sq. Ft.

Year Built:

1993

Lot

Lot Size (Sq. Ft):

17,424

Finances & Disclosures

Finances

Price:

$1,299,000

Price per Sq. Ft:

$927 per Sq. Ft.

MLS Logo
Bay East 2026. CCAR 2026 bridgeMLS 2026. Information Deemed Reliable But Not Guaranteed. This information is being provided by the Bay East MLS, or CCAR MLS, or bridgeMLS. The listings presented here may or may not be listed by the Broker/Agent operating this website. This information is intended for the personal use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated at May 1, 2026

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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.