4399 Glenwood DR Scotts Valley CA 95066 MLS #ML82037469

There are multiple listings for this address:
4399 Glenwood DR
Scotts Valley, CA, 95066
$1,299,000
3 Beds
2 Baths
1,400 SqFt
0.4 Acres
$1,299,000
4399 Glenwood DR
Scotts Valley, CA, 95066
MLS #ML82037469 image #0
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, 4933 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.

Property Details

Price:
$1,299,000
MLS #:
ML82037469
Status:
Active
Beds:
3
Baths:
2
Type:
Single Family
Subtype:
Duplex
Listed Date:
Mar 6, 2026
Finished Sq Ft:
1,400
Total Sq Ft:
1,930
Lot Size:
17,424 sqft / 0.40 acres (approx)
Year Built:
1993
TraditionalOtherOtherScotts ValleyOtherTrees/woods

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
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
Need more info?
Ask a Question
Ready to go see it?
Schedule a Showing

Get Out There, A Simply Outgoing Approach to Life. James Outland Jr. is one of those rare people who simply has an outgoing approach to life. No matter the activity… from dune buggy riding to skydiving to motorcycling to riding the local Pismo Beach waves… James Outland Jr. approaches life with a “just get out there and do it” kind of attitude. A zest for Life. James’ zest for life is obviously apparent in his many exciting hobbies. In his spare time, he loves riding dune buggies or hi…

More About James

Mortgage Calculator

 

Map

Current real estate data for Single Family in Scotts Valley as of Apr 12, 2026
43
Single Family Listed
42
Avg DOM
653
Avg $ / SqFt
$1,527,690
Avg List Price

Community

Similar Listings Nearby

broker reciprocity
MLS# ML82028887broker reciprocity
17060 Lon RD
Los Gatos, CA

$1,499,999

1.1 miles away

broker reciprocity
MLS# ML82003697broker reciprocity
24035 Stage Stop WY
Los Gatos, CA

$1,499,000

1.4 miles away

broker reciprocity
MLS# ML82039614broker reciprocity
489 Northridge DR
Scotts Valley, CA

$1,499,000

1.2 miles away

broker reciprocity
MLS# ML82040197broker reciprocity
14161 Old Japanese RD
Los Gatos, CA

$1,399,000

0.9 miles away

broker reciprocity
MLS# ML82037708broker reciprocity
25435 Hutchinson RD
Los Gatos, CA

$1,222,000

1.5 miles away

Property Summary

    4399 Glenwood DR Scotts Valley CA is a Single Family for sale in Scotts Valley, CA, 95066. It is listed for $1,299,000 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 $928. The average price per square foot for Single Family listings in Scotts Valley is $653. The average listing price for Single Family in Scotts Valley is $1,527,690. To schedule a showing of MLS#ml82037469 at 4399 Glenwood DR in Scotts Valley, CA, contact your James Outland agent at 8057482262.
4399 Glenwood DR
Scotts Valley, CA
4399 Glenwood DR
Scotts Valley, CA, 95066
$1,299,000
Beds
0 Baths
1,930 SqFt
0.4 Acres
$1,299,000
4399 Glenwood DR
Scotts Valley, CA, 95066
MLS #ML82039988 image #0
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, 4933 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.

Property Details

Price:
$1,299,000
MLS #:
ML82039988
Status:
Active
Beds:
0
Baths:
0
Type:
Single Family
Subtype:
Duplex
Listed Date:
Mar 24, 2026
Finished Sq Ft:
1,930
Total Sq Ft:
1,930
Lot Size:
17,424 sqft / 0.40 acres (approx)
Year Built:
1993
TraditionalOtherOtherScotts ValleyOtherTrees/woods

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
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
Need more info?
Ask a Question
Ready to go see it?
Schedule a Showing

Get Out There, A Simply Outgoing Approach to Life. James Outland Jr. is one of those rare people who simply has an outgoing approach to life. No matter the activity… from dune buggy riding to skydiving to motorcycling to riding the local Pismo Beach waves… James Outland Jr. approaches life with a “just get out there and do it” kind of attitude. A zest for Life. James’ zest for life is obviously apparent in his many exciting hobbies. In his spare time, he loves riding dune buggies or hi…

More About James

Mortgage Calculator

 

Map

Current real estate data for Single Family in Scotts Valley as of Apr 12, 2026
43
Single Family Listed
42
Avg DOM
653
Avg $ / SqFt
$1,527,690
Avg List Price

Community

Similar Listings Nearby

broker reciprocity
MLS# ML82028887broker reciprocity
17060 Lon RD
Los Gatos, CA

$1,499,999

1.1 miles away

broker reciprocity
MLS# ML82003697broker reciprocity
24035 Stage Stop WY
Los Gatos, CA

$1,499,000

1.4 miles away

broker reciprocity
MLS# ML82039614broker reciprocity
489 Northridge DR
Scotts Valley, CA

$1,499,000

1.2 miles away

broker reciprocity
MLS# ML82040197broker reciprocity
14161 Old Japanese RD
Los Gatos, CA

$1,399,000

0.9 miles away

broker reciprocity
MLS# ML82037469broker reciprocity
4399 Glenwood DR
Scotts Valley, CA

$1,299,000

0.0 miles away

broker reciprocity
MLS# ML82037708broker reciprocity
25435 Hutchinson RD
Los Gatos, CA

$1,222,000

1.5 miles away

Property Summary

    4399 Glenwood DR Scotts Valley CA is a Single Family for sale in Scotts Valley, CA, 95066. It is listed for $1,299,000 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 $673. The average price per square foot for Single Family listings in Scotts Valley is $653. The average listing price for Single Family in Scotts Valley is $1,527,690. To schedule a showing of MLS#ml82039988 at 4399 Glenwood DR in Scotts Valley, CA, contact your James Outland agent at 8057482262.
Scroll to Top