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18385 Chelmsford Drive

Cupertino, CA 95014

4 beds
3 baths
2,604 sqft
7,800 sqft lot
$1,340 per sqft
1990 build
– on site

Welcome to 18385 Chelmsford Drive, a beautifully updated home nestled in a peaceful Cupertino neighborhood with top-rated schools and unbeatable access to Silicon Valley's best amenities. This flexible floor plan includes a main-level bedroom and full bath ideal for guests, in-laws, or a home office. The formal entry opens to soaring ceilings, a bright living and formal dining areas offer an elegant setting for gatherings. The gorgeously renovated kitchen with quartz countertops, center island, and stainless steel appliances flows into a breakfast nook and family room for an open, connected feel. Upstairs, the luxurious primary suite offers a private retreat complete with vaulted ceilings, a cozy sitting area, two-way fireplace, dual vanities, a soaking tub, separate shower, skylights, and a spacious walk-in closet. The peaceful backyard provides a perfect space to relax or entertain, surrounded by mature landscaping and a tranquil atmosphere. Additional features include double pane windows, central HVAC, two car garage and much more. Conveniently located near Apple Park, Saratoga Creek Trail, Valley Fair, library and schools. Moments from downtown Cupertino, this home provides seamless access to world-class shopping, fine dining, vibrant culture and top-rated Cupertino School!!

Listed By CRMLS_CA / Shawn Luo / AEZ Investment, Inc.

Last checked: Checking… • Last updated Apr 20, 2025 •

MLS# ML82002741 —

This home is listed in more than one place. See it here, and here.

The Building

Year Built:

1990
Year Built Source:

Assessor
New Construction:

No
Roof:

Concrete
Foundation:

Slab
Stories Total:

2
Common Walls:

No Common Walls

Interior

Kitchen Features:

Quartz Counters
Eating Area:

Breakfast Nook
Window Features:

Skylight(s)
Flooring:

Carpet, Wood
Room Type:

Retreat, Walk-In Closet, Art Studio, Formal Entry, Laundry, Office, Workshop
Living Area Source:

Assessor
Fireplace:

Yes
Fireplace:

Family Room, Gas Starter, Living Room, Wood Burning
Laundry:

Washer Included, Dryer Included
Laundry:

1

Room Dimensions

Living Area:

2604.00

Location

Directions:

Cross Street: Bollinger Road
Latitude:

37.31309540
Longitude:

-121.99806114

The Property

Property Type:

Residential
Subtype:

Single Family Residence
Zoning:

R1
Lot Size Area:

7800.0000
Lot Size Acres:

0.1791
Lot Size SqFt:

7800.00
Lot Size Source:

Assessor

Listing Agent

Contact info:

Beds

Total Bedrooms:

4

Baths

Total Baths:

3
Bathroom Features:

Double sinks in bath(s)
Full & Three Quarter Baths:

3
Full Baths:

3

The Listing

Special Listing Conditions:

Standard
Parcel Number:

37522039

Heating & Cooling

Heating:

1
Heating:

Central
Cooling:

Yes
Cooling:

Central Air

Utilities

Sewer:

Public Sewer
Water Source:

Public

Appliances

Appliances:

Dishwasher, Disposal, Microwave, Vented Exhaust Fan, Refrigerator
Included:

Yes

Schools

High School:

Cupertino
High School:

CUPERT
High School District:

Other

The Community

Association:

Barrington Bridge HOA
Association:

Yes
Association Fee:

$70
Association Fee Frequency:

Monthly
Assessments:

No

Parking

Parking:

Yes
Parking:

Gated
Parking Spaces:

2.00
Attached Garage:

Yes
Garage Spaces:

2.00

Monthly cost estimate

Asking price

$3,490,000

Expense	Monthly cost
Mortgage	$18,687
Taxes	N/A
Insurance	$959
HOA fees	$70
Utilities	$199 See report
Total	$19,915/mo.^*
	^*This is an estimate

Explore the Area

My Commute

From

Walk Score®

Provided by WalkScore® Inc.

Bike Score®

Provided by WalkScore® Inc.

Transit Score®

Provided by WalkScore® Inc.

Soundscore™

Provided by HowLoud

Air Pollution Index

Provided by ClearlyEnergy

Sale history

Date	Event	Source	Price	% Change
4/16/25 Apr 16, 2025	Listed / Active	CRMLS_CA	$3,490,000	172.7% (12.5% / YR)
7/1/11 Jul 1, 2011		BRIDGE	$1,280,000
5/31/11 May 31, 2011	Price Changed	MLSLISTINGS

81% of nearby similar homes sold for over asking price

Similar homes that sold in bidding wars went $400k above asking price on average, but some went as high as $1.6M over asking price.

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This house located in Eastside, Cupertino, CA 95014 is currently for sale for $3,490,000. 18385 Chelmsford Drive is a 2,604 square foot house with 4 beds and 3 baths that has been on Estately for 4 days. 18385 Chelmsford Drive is in the Eastside neighborhood of Cupertino and has a WalkScore® of 21, making it car-dependent. This house is in the attendance area of Cupertino High School, Hyde Middle School, and Sedgwick Elementary School.

Listing Courtesy of: CRMLS_CA and AEZ Investment, Inc.. Based on information from California Regional Multiple Listing Service, Inc. as of 23:11 on Apr 20.

This information is for your personal, non-commercial use and may not be used for any purpose other than to identify prospective properties you may be interested in purchasing. Display of MLS data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and should investigate the data themselves or retain appropriate professionals. Information from sources other than the Listing Agent may have been included in the MLS data. Unless otherwise specified in writing, Broker/Agent has not and will not verify any information obtained from other sources. The Broker/Agent providing the information contained herein may or may not have been the Listing and/or Selling Agent.