There are multiple listings for this address:
TWO HOUSES in rare historic setting overlooking the 1880s Glenwood Train Turnaround & bordering the Glenwood to Wrights rail tunnel! Discover a rare dual-residence opportunity perfectly blending mountain serenity, historic rail heritage & everyday convenience, nestled at the border of Scotts Valley & Los Gatos in the coveted Santa Cruz Mountains. This unique property features 2 fully independent homes surrounded by tranquil wooded views, open pastures & a seasonal creek. 4399 Glenwood Dr is a meticulously maintained & updated 3BR/2BA sanctuary offering 1400 SF of warm living space. The home sits within a fully fenced, private oasis combining peaceful seclusion with effortless access to Highway 17, Santa Cruz beaches & Silicon Valley employment hubs. 4401 Glenwood Dr is tucked privately behind the main house on its own private right of way. This updated 1BR/1BA, 530 SF home serves as an ideal source for rental income, multi-generational living, or guest accommodations. Enjoy this versatile property that seamlessly balances premium lifestyle, a prime commuter location & long-term income potential.
Property Details
Price:
$1,174,000
MLS #:
ML82053482
Status:
Active
Beds:
3
Baths:
2
Type:
Single Family
Subtype:
Duplex
Neighborhood:
699notdefined
Listed Date:
Jul 8, 2026
Finished Sq Ft:
1,930
Total Sq Ft:
1,930
Lot Size:
17,424 sqft / 0.40 acres (approx)
Year Built:
1993
See this Listing
Schools
School District:
Other
Elementary School:
Other
Middle School:
Scotts Valley
High School:
Other
Interior
Appliances
DW, RF, GO, GS, HOD, SCO
Cooling
WHF
Flooring
TILE, LAM, CARP
Heating
WL
Exterior
Accessibility Features
NO
Architectural Style
TRD
Parking Spots
5
Parking Total
5
Roof
CMP, SHN
View
HI, RV, TW
Financial
Taxes
$11,242
Map
Community
- Address4399 Glenwood DR Scotts Valley CA
- CityScotts Valley
- CountySanta Cruz
- Zip Code95066
Market Summary
Current real estate data for Single Family in Scotts Valley as of Sep 29, 2026
45
Single Family Listed
58
Avg DOM
684
Avg $ / SqFt
$1,456,064
Avg List Price
Property Summary
- 4399 Glenwood DR Scotts Valley CA is a Single Family for sale in Scotts Valley, CA, 95066. It is listed for $1,174,000 and features 3 beds, 2 baths, and has approximately 1,400 square feet of living space, and was originally constructed in 1993. The current price per square foot is $839. The average price per square foot for Single Family listings in Scotts Valley is $684. The average listing price for Single Family in Scotts Valley is $1,456,064.
Similar Listings Nearby
Courtesy of Miritz & Bailey Real Estate, Inc. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the California Regional Multiple Listing Service. Detailed information about real estate listings held by brokerage firms other than include the name of the listing broker. Neither the listing company nor shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. California Regional Multiple Listing Service. All rights reserved.4399 Glenwood DR
Scotts Valley, CA
TWO HOUSES in rare historic setting overlooking the 1880s Glenwood Train Turnaround & bordering the Glenwood to Wrights rail tunnel! Discover a rare dual-residence opportunity perfectly blending mountain serenity, historic rail heritage & everyday convenience, nestled at the border of Scotts Valley & Los Gatos in the coveted Santa Cruz Mountains. This unique property features 2 fully independent homes surrounded by tranquil wooded views, open pastures & a seasonal creek. 4399 Glenwood Dr is a meticulously maintained & updated 3BR/2BA sanctuary offering 1400 SF of warm living space. The home sits within a fully fenced, private oasis combining peaceful seclusion with effortless access to Highway 17, Santa Cruz beaches & Silicon Valley employment hubs. 4401 Glenwood Dr is tucked privately behind the main house on its own private right of way. This updated 1BR/1BA, 530 SF home serves as an ideal source for rental income, multi-generational living, or guest accommodations. Enjoy this versatile property that seamlessly balances premium lifestyle, a prime commuter location & long-term income potential.
Property Details
Price:
$1,174,000
MLS #:
ML82054170
Status:
Active
Beds:
0
Baths:
0
Type:
Single Family
Subtype:
Duplex
Neighborhood:
699notdefined
Listed Date:
Jul 14, 2026
Finished Sq Ft:
1,930
Total Sq Ft:
1,930
Lot Size:
17,424 sqft / 0.40 acres (approx)
Year Built:
1993
See this Listing
Schools
School District:
Other
Elementary School:
Other
Middle School:
Scotts Valley
High School:
Other
Interior
Appliances
DW, RF, GO, GS, HOD, SCO
Cooling
WHF
Flooring
TILE, LAM, CARP
Heating
WL
Exterior
Accessibility Features
NO
Architectural Style
TRD
Parking Spots
5
Parking Total
5
Roof
CMP, SHN
View
HI, RV, TW
Financial
Taxes
$11,242
Map
Community
- Address4399 Glenwood DR Scotts Valley CA
- CityScotts Valley
- CountySanta Cruz
- Zip Code95066
Market Summary
Current real estate data for Single Family in Scotts Valley as of Sep 29, 2026
45
Single Family Listed
58
Avg DOM
684
Avg $ / SqFt
$1,456,064
Avg List Price
Property Summary
- 4399 Glenwood DR Scotts Valley CA is a Single Family for sale in Scotts Valley, CA, 95066. It is listed for $1,174,000 and features 0 beds, 0 baths, and has approximately 1,930 square feet of living space, and was originally constructed in 1993. The current price per square foot is $608. The average price per square foot for Single Family listings in Scotts Valley is $684. The average listing price for Single Family in Scotts Valley is $1,456,064.