18385 Chelmsford DR
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!!
Last checked:
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Last updated Apr 20, 2025
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MLS# 82002741 —
This home is listed in more than one place. See it here, and here.
The Building
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Year Built:1990
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Age:35
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Construction Type:Wood Frame
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Type:Detached
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Subclass:Single Family Home
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Roofing:Concrete
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Foundation:Concrete Slab
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# of Stories:2
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Structure SqFt:2604
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Structure SqFt Source:Assessor
Interior
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Kitchen:Dishwasher, Island with Sink, Garbage Disposal, Hookups - Gas, Microwave, Countertop - Quartz, Pantry, Exhaust Fan, Oven Range - Gas, Refrigerator
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Dining Room:Formal Dining Room, Breakfast Nook
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Family Room:Separate Family Room
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Additional Rooms:Artist Studio, Formal Entry, Laundry Room, Office Area, Workshop
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Fireplace:Yes
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Fireplaces:Dual See Thru, Family Room, Gas Starter, Living Room, Other Location, Primary Bedroom, Wood Burning
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Fireplaces:3
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Flooring:Carpet, Vinyl / Linoleum, Hardwood
Room Dimensions
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Living SqFt:2604
Location
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Cross Street:Bollinger Road
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City Limits:Yes
The Property
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Lot Acres:0.1791
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Lot Size Area Min:7800.00
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Zoning:R1
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Parcel Number:375-22-039
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Horse Property:No
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Yard/Grounds:Gazebo, Sprinklers - Auto, Storage Shed / Structure
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Fencing:Fenced
Listing Agent
- Contact info:
- No listing contact info available
Taxes
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Property ID:82002741
Beds
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Total:4
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Bedrooms:Primary Suite / Retreat, Walk-in Closet, Ground Floor Bedroom
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Beds Max:4
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Beds Min:4
Baths
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Full Baths:3
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Bathroom Features:Shower over Tub - 1, Double Sinks, Skylight, Full on Ground Floor, Primary - Oversized Tub, Primary - Stall Shower(s), Stall Shower - 2+, Primary - Tub with Jets, Tubs - 2+
The Listing
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Branded Additional Tour:
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Additional Listing Info:Not Applicable
Heating & Cooling
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Cooling Methods:Central AC, Multi-Zone
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Heating Methods:Central Forced Air
Utilities
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Utilities:Public Utilities
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Sewer/Septic System:Sewer - Public, Sewer Connected
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Water Source:Public
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Energy Features:Double Pane Windows, Energy Star Appliances
Appliances
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Laundry:Electricity Hookup (220V), Washer, Washer / Dryer, Inside, Dryer
The Community
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Complex Name:Barrington Bridge
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HOA:Yes
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HOA Fee:Monthly
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HOA Fee:$70
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Association Fees Include:Maintenance - Road, Insurance - Common Area
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Amenities Misc.:Walk-in Closet, Wet Bar, High Ceiling, Skylight
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Pool:No
Parking
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Description and Access:Attached Garage, Gate / Door Opener
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Garage:2
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Garage:2
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Garage Spaces:2
Monthly cost estimate

Asking price
$3,490,000
Expense | Monthly cost |
---|---|
Mortgage
This calculator is intended for planning and education purposes only. It relies on assumptions and information provided by you regarding your goals, expectations and financial situation, and should not be used as your sole source of information. The output of the tool is not a loan offer or solicitation, nor is it financial or legal advice. |
$18,687
|
Taxes | N/A |
Insurance | $959 |
HOA fees | $70 |
Utilities | $199 See report |
Total | $19,915/mo.* |
*This is an estimate |
Walk Score®
Provided by WalkScore® Inc.
Walk Score is the most well-known measure of walkability for any address. It is based on the distance to a variety of nearby services and pedestrian friendliness. Walk Scores range from 0 (Car-Dependent) to 100 (Walker’s Paradise).
Bike Score®
Provided by WalkScore® Inc.
Bike Score evaluates a location's bikeability. It is calculated by measuring bike infrastructure, hills, destinations and road connectivity, and the number of bike commuters. Bike Scores range from 0 (Somewhat Bikeable) to 100 (Biker’s Paradise).
Transit Score®
Provided by WalkScore® Inc.
Transit Score measures a location's access to public transit. It is based on nearby transit routes frequency, type of route (bus, rail, etc.), and distance to the nearest stop on the route. Transit Scores range from 0 (Minimal Transit) to 100 (Rider’s Paradise).
Soundscore™
Provided by HowLoud
Soundscore is an overall score that accounts for traffic, airport activity, and local sources. A Soundscore rating is a number between 50 (very loud) and 100 (very quiet).
Air Pollution Index
Provided by ClearlyEnergy
The air pollution index is calculated by county or urban area using the past three years data. The index ranks the county or urban area on a scale of 0 (best) - 100 (worst) across the United Sates.
Sale history
Date | Event | Source | Price | % Change |
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4/16/25
Apr 16, 2025
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Listed / Active | MLSLISTINGS | $3,490,000 | 172.7% (12.5% / YR) |
7/1/11
Jul 1, 2011
|
BRIDGE | $1,280,000 |

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.