Are yards well-kept in Jollyman, Cupertino, CA?

As of early 2026, 86% of users say yards are well-kept

Is Jollyman, Cupertino, CA dog-friendly?

As of early 2026, 86% of users say it's dog friendly

Is parking easy in Jollyman, Cupertino, CA?

As of early 2026, 85% of users say parking is easy

Does Jollyman, Cupertino, CA have sidewalks?

As of early 2026, 82% of users say there are sidewalks

Is Jollyman, Cupertino, CA walkable to grocery stores?

As of early 2026, 80% of users say it's walkable to grocery stores

Does Jollyman, Cupertino, CA show holiday spirit?

As of early 2026, 75% of users say there's holiday spirit

Is a car needed in Jollyman, Cupertino, CA?

As of early 2026, 75% of users say car is needed

Is Jollyman, Cupertino, CA quiet?

As of early 2026, 73% of users say it's quiet

Is Jollyman, Cupertino, CA walkable to restaurants?

As of early 2026, 65% of users say it's walkable to restaurants

Are the streets well-lit in Jollyman, Cupertino, CA?

As of early 2026, 62% of users say streets are well-lit

Would people walk alone at night in Jollyman, Cupertino, CA?

As of early 2026, 61% of users say people would walk alone at night

Do residents of Jollyman, Cupertino, CA plan to stay at least 5 years?

As of early 2026, 58% of users say they plan to stay for at least 5 years

Do kids play outside in Jollyman, Cupertino, CA?

As of early 2026, 55% of users say kids play outside

Is there wildlife in Jollyman, Cupertino, CA?

As of early 2026, 52% of users say there's wildlife

Are neighbors friendly in Jollyman, Cupertino, CA?

As of early 2026, 42% of users say neighbors are friendly

Are there community events in Jollyman, Cupertino, CA?

As of early 2026, 26% of users say there are community events

What is 20653 Cheryl Dr estimated to be worth?

Trulia's estimated value for 20653 Cheryl Dr in Cupertino, CA is $2,836,700 .

What is the price history for 20653 Cheryl Dr?

20653 Cheryl Dr in Cupertino, CA last sold for $2,550,000 in June 2022.

Is Cupertino a buyer's or seller's market?

Cupertino is currently a seller's market, based on recent for-sale activity.

What's the median sale price in Cupertino?

The median sale price in Cupertino is $3.03M. That is down $180K from the prior month.

How big is the lot at 20653 Cheryl Dr?

The lot at 20653 Cheryl Dr in Cupertino, CA is about 0.17 acres (7,405 sq ft).

Does 20653 Cheryl Dr have a garage?

Yes, 20653 Cheryl Dr in Cupertino, CA has a garage.

OFF MARKET

$2,836,700

Trulia Estimate

3 Beds
2 Baths
1,416 sqft

20653 Cheryl Dr, Cupertino, CA 95014

Jollyman

Est. Refi. Payment $17,834/mo*

Refinance Your Home

Currently Off Market - Sold Jun 9, 2022 for $2,550,000

Home Value

Trulia Estimate

$2.84M

Since last month

$64K (+2.2%)

Since last year

$84K (+3%)

Since last sale

$361K (+14.2%)

Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +76% in the last 10 years

Month	Estimated value
2026
September 2026	$2.91M
August 2026	$2.84M
July 2026	$2.85M
June 2026	$2.89M
May 2026	$2.96M
April 2026	$2.99M
March 2026	$3.05M
February 2026	$3.05M
January 2026	$2.91M
2025
December 2025	$2.89M
November 2025	$2.9M
October 2025	$2.9M
September 2025	$2.92M
August 2025	$2.83M
July 2025	$2.89M
June 2025	$2.93M
May 2025	$2.93M
April 2025	$3.05M
March 2025	$3.07M
February 2025	$3.05M
January 2025	$2.97M
2024
December 2024	$3M
November 2024	$2.95M
October 2024	$3.04M
September 2024	$2.95M
August 2024	$2.95M
July 2024	$2.93M
June 2024	$2.96M
May 2024	$2.99M
April 2024	$2.94M
March 2024	$2.92M
February 2024	$2.81M
January 2024	$2.68M
2023
December 2023	$2.56M
November 2023	$2.63M
October 2023	$2.41M
September 2023	$2.6M
August 2023	$2.57M
July 2023	$2.56M
June 2023	$2.46M
May 2023	$2.4M
April 2023	$2.33M
March 2023	$2.33M
February 2023	$2.38M
January 2023	$2.34M
2022
December 2022	$2.44M
November 2022	$2.43M
October 2022	$2.54M
September 2022	$2.56M
August 2022	$2.4M
July 2022	$2.47M
June 2022	$2.55M
May 2022	$2.73M
April 2022	$3.02M
March 2022	$3.01M
February 2022	$2.54M
January 2022	$2.52M
2021
December 2021	$2.45M
November 2021	$2.39M
October 2021	$2.32M
September 2021	$2.26M
August 2021	$2.29M
July 2021	$2.36M
June 2021	$2.38M
May 2021	$2.48M
April 2021	$2.4M
March 2021	$2.27M
February 2021	$2.28M
January 2021	$2.26M
2020
December 2020	$2.21M
November 2020	$2.22M
October 2020	$2.15M
September 2020	$2.11M
August 2020	$2.11M
July 2020	$2.1M
June 2020	$2.08M
May 2020	$2.08M
April 2020	$2.15M
March 2020	$2.14M
February 2020	$2.11M
January 2020	$2.01M
2019
December 2019	$2.01M
November 2019	$1.99M
October 2019	$2M
September 2019	$2.01M
August 2019	$2.01M
July 2019	$2.05M
June 2019	$2M
May 2019	$2.04M
April 2019	$2.06M
March 2019	$2.1M
February 2019	$2.18M
January 2019	$2.23M
2018
December 2018	$2.27M
November 2018	$2.28M
October 2018	$2.26M
September 2018	$2.36M
August 2018	$2.33M
July 2018	$2.48M
June 2018	$2.46M
May 2018	$2.42M
April 2018	$2.41M
March 2018	$2.35M
February 2018	$2.19M
January 2018	$2.13M
2017
December 2017	$2.07M
November 2017	$2.02M
October 2017	$1.96M
September 2017	$1.92M
August 2017	$1.87M
July 2017	$1.84M
June 2017	$1.78M
May 2017	$1.76M
April 2017	$1.73M
March 2017	$1.73M
February 2017	$1.71M
January 2017	$1.69M
2016
December 2016	$1.69M
November 2016	$1.68M
October 2016	$1.67M
September 2016	$1.66M

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
20666 Craig Ct, Cupertino, CA	0.07	Single-Family Home	$3,150,000	11/19/25	3	2	1,416
7453 Bollinger Rd, Cupertino, CA	0.27	Single-Family Home	$2,300,000	10/31/25	3	2	1,115
7492 De Foe Dr, Cupertino, CA	0.36	Single-Family Home	$2,530,000	10/30/25	3	2	1,115
7577 Bollinger Rd, Cupertino, CA	0.31	Single-Family Home	$3,130,000	04/24/26	4	2	1,728
10581 Whitney Way, Cupertino, CA	0.40	Single-Family Home	$3,450,000	11/12/25	3	2	1,838
7490 Dumas Dr, Cupertino, CA	0.42	Single-Family Home	$3,160,000	04/08/26	3	2	1,265
10151 Bonny Dr, Cupertino, CA	0.33	Single-Family Home	$3,485,000	08/25/26	4	2	1,780
7733 Lilac Way, Cupertino, CA	0.45	Single-Family Home	$3,000,000	05/26/26	4	2	1,635
20087 Pacifica Dr, Cupertino, CA	0.58	Single-Family Home	$2,920,000	04/13/26	3	2	1,169
20571 Sunrise Dr, Cupertino, CA	0.28	Single-Family Home	$3,500,000	05/06/26	3	1	1,253

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.

Address	Distance	Price	Bed	Bath	Sqft	Status
20665 Nancy Ct, Cupertino, CA 95014	0.05	$3,634,000	4	3	1,779	Off Market
20684 Nancy Ct, Cupertino, CA 95014	0.04	$3,455,600	3	2	1,416	Off Market
10386 Tonita Way, Cupertino, CA 95014	0.07	$3,503,800	3	2	1,784	Off Market
10376 Tonita Way, Cupertino, CA 95014	0.08	$3,788,900	5	3.5	2,139	Off Market
20692 Cheryl Dr, Cupertino, CA 95014	0.07	$3,341,200	4	3	1,779	Off Market
10525 John Way, Cupertino, CA 95014	0.09	$3,494,500	3	1.5	1,762	Off Market
10470 Westacres Dr, Cupertino, CA 95014	0.11	$3,280,100	3	2	1,514	Off Market
20690 Rodrigues Ave, Cupertino, CA 95014	0.18	$3,628,800	3	2	1,640	Off Market
20600 Rodrigues Ave, Cupertino, CA 95014	0.19	$5,452,400	6	6	3,794	Off Market
10567 John Way, Cupertino, CA 95014	0.14	$4,804,200	4	4.5	3,551	Off Market
20808 Shelly Dr, Cupertino, CA 95014	0.18	$3,453,800	3	2	1,658	Off Market
20500 Town Center Ln #176, Cupertino, CA 95014	0.22	$1,352,100	3	2	1,193	Off Market

Local Information

Map ViewExplore the area around 20653 Cheryl Dr.
Schools1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

Built in 1963

1,416 sqft

$2,003/sqft

Garage

About this House

This single-family home is located at 20653 Cheryl Dr, Cupertino, CA. 20653 Cheryl Dr is in the Jollyman neighborhood in Cupertino, CA and in ZIP code 95014. This property has 3 bedrooms, 2 bathrooms and approximately 1,416 sqft of floor space. This property has a lot size of 7405 sqft and was built in 1963.

20653 Cheryl Dr, Cupertino, CA 95014 is a 3 bedroom, 2 bathroom, 1,416 sqft single-family home in Jollyman, built in 1963. It last sold for $2,550,000 on Jun 9, 2022. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,836,700, with a rent estimate of $5,337/month.

Home Details for 20653 Cheryl Dr

Interior Features
Levels, Entrance, & Accessibility Stories: 1
Interior Details Number of Rooms: 6
Fireplace & Spa Fireplace

Property Information
Year Built Year Built: 1963Year Updated: 1963
Property Type / Style Property Type: Single Family HomeArchitecture: Other

Exterior Features
Parking & Garage GarageParking: Garage Attached

Community
Units in Building: 1

Lot Information
Lot Area: 7405 sqft

Price and Tax history

Date	Event	Price
Jun 9, 2022 Source: N/A	Sold	$2,550,000
May 11, 2022 Source: MLSListings Inc #ML81891015	Listed For Sale	$2,398,000

Year	Property tax	Tax assessment
2026	Unavailable	$2,760,201

Additional Cost

Market trends in Cupertino

Last updated August 2026

Avg. sale price

$3.03M

$180KMoM

Sale-to-List Price

101.6%

0.4%MoM

Price per sq ft

$1.45K

$65MoM

Available listings

1MoM

Around this home

Abraham Lincoln Elementary School
K-5
Public
662 Students
Cupertino Union School District
9/10
GreatSchools Rating
Parent Rating Average
Amazing principal. Teachers are also excellent, though the experience and things like amount of homework can differ significantly even between teachers within the same grade. Social growth, personal responsibility, and citizenship are important here. About the only thing I can really complain about is that the provider for the school lunches (across all of CUSD, not just this school) is below average, but due to the state program at least it's currently free.
Parent Review
3y ago
27 Reviews

View nearby schools on GreatSchools

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

Neighborhood Overview

Jollyman

9 Homes For You
Buy: $1.25m - $5.45m

See Local Highlights

Neighborhood stats provided by third party data sources.

What Locals Say about Jollyman

At least 18 Trulia users voted on each feature.

86 % Say yards are well-kept
86 % Say it's dog friendly
85 % Say parking is easy
82 % Say there are sidewalks
80 % Say it's walkable to grocery stores
75 % Say there's holiday spirit
75 % Say car is needed
73 % Say it's quiet
65 % Say it's walkable to restaurants
62 % Say streets are well-lit
61 % Say people would walk alone at night
58 % Say they plan to stay for at least 5 years
55 % Say kids play outside
52 % Say there's wildlife
42 % Say neighbors are friendly
26 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.

biapayne
Resident
8y ago
"Great schools, nice parks, teen center, 11PM teen curfew, lots of restaurants, good weather, housing is very expensive. "
2
Flag
Neelika C.
12y ago
"Love the Cupertino area. This tract is like a quiet bedroom community yet is walking distance from Apple HQ and restaurants and shopping."
0
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Frequently asked questions about 20653 Cheryl Dr

What is 20653 Cheryl Dr estimated to be worth?
Trulia's estimated value for 20653 Cheryl Dr in Cupertino, CA is $2,836,700.
What is the price history for 20653 Cheryl Dr?
20653 Cheryl Dr in Cupertino, CA last sold for $2,550,000 in June 2022.
Is Cupertino a buyer's or seller's market?
Cupertino is currently a seller's market, based on recent for-sale activity.
What's the median sale price in Cupertino?
The median sale price in Cupertino is $3.03M. That is down $180K from the prior month.
How big is the lot at 20653 Cheryl Dr?
The lot at 20653 Cheryl Dr in Cupertino, CA is about 0.17 acres (7,405 sq ft).
Does 20653 Cheryl Dr have a garage?
Yes, 20653 Cheryl Dr in Cupertino, CA has a garage.