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$1,299,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1,400 Sq. Ft.
  • Updated 3 days ago
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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.

Full Property Details for 4399 Glenwood Dr

General

  • Price: $1,299,000
  • Status: Active
  • Type: Single Family
  • Source: RE_Infolink
  • MLS ID: ML82037469
  • Updated: 3/6/2026
  • Added to Site: 3 day(s) ago

Interior

  • Rooms/Areas: Den / Study / Office, Loft
  • Interior Features: Vaulted Ceiling
  • Flooring: Carpet, Wood

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2
  • Bathroom Features: 1 Shower over Tub, Tile, Updated Bath, Full on Ground Floor, Primary - Stall Shower(s)

Bedrooms

  • Total Bedrooms: 3
  • Bedroom Features: Primary Bedroom on Ground Floor, Ground-Floor Bedroom

Other Rooms

  • Family Room: No Family Room
  • Kitchen: Dishwasher, Gas Cooktop, Hood over Range, Self-Cleaning Oven, Countertop - Quartz, Refrigerator, Gas Oven
  • Laundry: Washer / Dryer
  • Guest Quarters: 530 SF, 1BR/1BA, 530

Additional Information

  • Extras: Not Applicable
  • Security/Safety: None

Parking

  • Parking Features: Off-Street Parking, Uncovered Parking

Location

  • Area: Scotts Valley North
  • County: Santa Cruz
  • Cross Streets: Glenwood Cutoff

Heating & Cooling

  • Cooling Type: Whole House / Attic Fan, Other
  • Heating Type: Wall Furnace

Utilities

  • Sewer: Septic System Connected, Existing Septic System
  • Water: Well
  • Telecomm.: Cable TV
  • Utility Description: Generator, Individual Electric Meters, Propane on Site

Structural Information

  • Architectural Style: Traditional
  • Construction: Detached, Wood Frame
  • Foundation: Concrete Perimeter
  • Roof: Rolled Composition, Shingle, Composition
  • Disability Access: None
  • Square Feet: 1,400
  • Year Built: 1993

Lot Features

  • Property View: Hills, River / Stream, Forest / Woods
  • Lot Size (Acres): 0.4
  • Minimum Lot Size: 17424
  • Lot Size (Sq. Ft.): 17,424
  • Grounds/Landscape: Back Yard, Fenced, Balcony / Patio, Sprinklers - Lawn, Drought-Tolerant Plants, Storage Shed / Structure
  • Zoning: RA
  • Lot Description: Seasonal Stream, Mostly Level
  • Fencing (Description): Fenced

Green Features

  • Energy Efficient: Low-Flow Shower, Low-Flow Toilet, Floor Insulation

Listed by Miritz & Bailey Real Estate, Inc, Lisa Dailey-goodrich

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Listing agent

— 4399 Glenwood Dr —

  • Lisa Dailey-goodrich

    Miritz & Bailey Real Estate, Inc

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 4399 Glenwood Dr

School District:Scotts Valley Unified School District
NameGradesDistance
Vine Hill Elementary School
151 Vine Hill School Road, Scotts Valley, CA 95066
K-53 mi
Scotts Valley Middle School
8 Bean Creek Road, Scotts Valley, CA 95066
6-85 mi
Scotts Valley High School
555 Glenwood Drive, Scotts Valley, CA 95066
9-122.8 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 4399 Glenwood Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
3/06/2026
Listed
$1,299,000
79.17%
MLS
10/14/2015
Sold
$725,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 4399 Glenwood Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$5,733
10%
$450,435
4%
2023
$5,218
2%
$432,945
2%
2022
$5,131
4%
$424,455
2%
2021
$4,915
1%
$416,132
1%
2020
$4,879
1%
$411,866
2%
2019
$4,810
6%
$403,789
2%
2018
$4,543
106%
$395,872
122%
2017
$2,202
4%
$178,135
2%
2016
$2,121
1%
$174,642
2%
2015
$2,091
2%
$172,018
2%
2014
$2,044
—
$168,649
—
2013
$2,048
—
$167,887
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Listed by Miritz & Bailey Real Estate, Inc, Lisa Dailey-goodrich

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4399 Glenwood Dr, Scotts Valley, CA 95066 (MLS# ML82037469) is a Single Family property with 3 bedrooms and 2 full bathrooms. 4399 Glenwood Dr is currently listed for $1,299,000 and was received on March 06, 2026. Want to learn more about 4399 Glenwood Dr? Do you have questions about finding other Single Family real estate for sale in Scotts Valley? You can browse all Scotts Valley real estate or contact a Coldwell Banker agent to request more information.

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