For Sale31d on market
4399 Glenwood Dr
Scotts Valley, CA, 95066 • 95066 • Santa Cruz County
$1,299,000
$928/sqft
Down payment assistance available
3Beds
2Baths
1,400Sqft
0.4 acLot
1993Built
Property DNA
Scenic Views
Forest/Woods · Hills
Traditional Style
Built 1993 · 33 years of history
Outdoor Living
Balcony/Patio
Special Features
Other · Zoned2ndUnit
Wood Floors
Quality flooring throughout
This home is getting attention
Listed 31 days ago · 4,057 views · 161 saves
Market activity
Demand and pricing signals for this listing
4,057 views
People checking out this listing
161 saves
Buyers have saved this home
31 days on market
Established listing
$928/sqft
Price per square foot
About this home
Single Family · Built 1993
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.
Standout features identified
Our analysis highlights open pastures, peaceful seclusion, and tranquil wooded surroundings as key attractions of this home.
Estimated monthly payment
Based on current rates
$8,289/month
Principal & Interest$6,557
Property Tax$1,299
Insurance$433
Down payment20% ($259,800)
3%50%
Est. 6.48% rate · 30yr fixed · $1,039,200 loan
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At a glance
Key facts and listing details
TypeSingle Family Residence, Residential
Year Built1993
HeatingWall Furnace
CoolingOther, Whole House Fan
Parking5 Parking spaces
Lot0.40 Acres
Days on Zillow31 Days
Price/sqft$928
Property
Home typeSingle Family
Sub-typeSingle Family Residence, Residential
StyleTraditional
Year built1993
Stories2
Systems
HeatingWall Furnace
CoolingOther, Whole House Fan
RoofComposition, RolledHotMop, Shingle
Water / SewerWell / Septic Tank
Parking & Outdoor
ParkingOff Street
Lot0.40 Acres
Location & Tax
Neighborhood95066
ZoningRA
Annual tax$5,733
Parcel09306104
Bathrooms & Fees
Full baths2
Features & details
14 categories of property features
Interior Features
Interior
Vaulted Ceiling(s)
Appliances
Gas Cooktop
Dishwasher
Range Hood
Gas Oven
Self Cleaning Oven
Refrigerator
Washer/Dryer
Flooring
Carpet
Wood
Heating
Wall Furnace
Cooling
Other
Whole House Fan
Accessibility
None
Exterior Features
Exterior
Back Yard
Fenced
Storage Shed Structure
Drought Tolerant Plants
Parking
Off Street
Patio & Porch
Balcony/Patio
Lot Features
Mostly Level
Views
Forest/Woods
Hills
Utilities
Propane
Gas
Generator
PropaneOnSite
Other Structures
Other
Zoned2ndUnit
Room details
4 rooms detailed
Bedroom
GroundFloorBedroomPrimaryBedroomonGroundFloor
Bathroom
PrimaryStallShowersShoweroverTub1TileUpdatedBathsFullonGroundFloor
Dining Room
DiningArea
Family Room
NoFamilyRoom
Listing insights
Market data and value estimates
StatusFor Sale
Days on market31
Est. value$1,261,900
Est. rent$4,229/mo
Tax rate1.10%
Price/sqft$928
On marketMar 6, 2026
PostedMar 7, 2026
Last sold$725,100
MLS updatedApr 4, 2026
Tour days9
Views4,057
Favorites161
How are the schools in Scotts Valley?
3 schools rated nearby
Location
Scotts Valley, CA, 95066
Price history
4 events
DateEventPrice$/sqftSource
Mar 7, 2026Listed For Sale$1,299,000$928MLSListings Inc
Nov 3, 2021Listing Removed——Zillow Rental Manager
Oct 26, 2021Listed For Rent$4,000$3Zillow Rental Manager
Oct 22, 2015Sold$725,100$518Agent Provided
Listed For Sale$1,299,000
Mar 7, 2026•$928/sqft•MLSListings Inc
Listing Removed—
Nov 3, 2021•Zillow Rental Manager
Listed For Rent$4,000
Oct 26, 2021•$3/sqft•Zillow Rental Manager
Sold$725,100
Oct 22, 2015•$518/sqft•Agent Provided
Tax history
25 years of records
YearTax paidAssessed value
Apr 7, 2025$5,733$450,435
Apr 7, 2024$5,355$441,603
Apr 7, 2023$5,218$432,945
Apr 7, 2022$5,131$424,455
Apr 7, 2021$4,915$416,132
Apr 7, 2020$4,879$411,866
Apr 7, 2019$4,810$403,789
Apr 7, 2018$4,543$395,872
Apr 7, 2017$2,202$178,135
Apr 7, 2016$2,121$174,642
Apr 7, 2015$2,091$172,018
Apr 7, 2014$2,044$168,649
Apr 7, 2012—$164,595
Apr 7, 2011—$161,368
Apr 7, 2010—$160,162
Apr 7, 2009—$160,543
Apr 7, 2008—$157,395
Apr 7, 2007—$154,309
Apr 7, 2006—$151,284
Apr 7, 2005—$148,318
Apr 7, 2004—$145,410
Apr 7, 2003—$142,745
Apr 7, 2002—$139,946
Apr 7, 2001—$137,202
Apr 7, 2000—$134,512
Nearby homes
Neighborhood details
Local context around this listing
Scotts Valley, CA • Santa Cruz County
Nearby cities
AptosBen LomondBoulder CreekCapitolaFeltonLos GatosSanta CruzScotts Valley
Nearby zip codes
9506695067
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Based on information from the MLSListings MLS as of 2026-04-07 11:19:10 PDT. All data, including all measurements and calculations of area, is obtained from various sources and has not been, and will not be, verified by broker or MLS. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
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