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Courtstyle and Wimbledon Place, which is also referred to as Courtside by many locals, are townhome communities located between La Rinconada Golf Course and Winchester Boulevard, just behind the Los Gatos Bay Club Courtside.  (The Bay Club Courtside was originally just “Courtside”, and that seems to be the reason for the community’s nickname.) This is a convenient commute location near both highways 17 and 85, and the area is within the Los Gatos Union School District, which is a big draw.

The Courtstyle and Wimbledon Place communities are sometimes confused with each other since they are nearby neighbors with some similar features and not terribly far apart in age, but they are distinct.

Courtstyle and Wimbledon Place map

The Wimbledon Place HOA put Wimbledon Place signs up at the front and back entrances of the community not too long ago with the intention of getting the neighborhood branding corrected.

Wimbledon Place sign


Wimbledon Place, or Courtside

Courtside Los Gatos - townhomes green

The Wimbledon Place townhouses were built in 1977 and often “feel” like you’re in a single family home as the rooms are a good size, the floor plans are fairly open, and living rooms frequently feature vaulted and beamed ceilings.  This is an uncrowded neighborhood, with plenty of parking in driveways and other designated spaces. It’s a very tidy, well kept neighborhood and seems to be one of the best values in town.

In the past, some of the homes felt dark as there were a lot of oversized (but beautiful!) redwood trees. When I was there this week, I noticed that a number of them had been cut down.  It’s sad to see them go, but at the same time, they were close to power lines and cast a lot of shade. There are still a good number of trees there, too.

What are the homes like at Wimbledon Place?

There are 111 townhouses in this community, and they are Planned Unit Developments, not condominiums.

Courtside or Wimbledon Place End Units - tan homes

Homes are mostly 2 and 3 bedrooms, but there is a very small handful with 4 (some of which may be later conversions of a den or other space).  Home sizes start at 1409 SF (2 bedroom units) and go to almost 2400 SF of living space, with the average being 1877 square feet. Most townhouses are 2 stories, but there are 38 single story properties in the mix. All have 2 car garages and some dedicated outdoor place.

Wimbledon Place currently has dues of about $522. The community includes not 1, but 3 swimming pools! The HOA  dues also cover the roofs of each unit.

One of the 3 pools at Wimbledon Place (Courtside)

What do homes sell for at Courtside, or Wimbledon Place?

This is not a “high turnover” community, so there are not tons of recent sales. The three sales year to date here have been between about $1,250,000 and $1,600,000. Much will depend on the numbers of bedrooms and bathrooms, square footage, and condition.

Location within the community will be really important, also.

High voltage power lines run down the middle of Wimbledon Drive, and highway 85 and the train tracks are near by, so this may impact values depending on any particular unit’s proximity to them. Below is a view looking toward the freeway.

ourtside Power Lines view toward freeway

Same street, but opposite direction – notice the beautiful hills in the background:

Wimbledon Drive Power Lines view toward the hills



Just around the corner, and on the other side of the railroad tracks and walking trail, is the slightly younger, smaller, and more modest Courtstyle community. Inside, these also feel like a house more than a townhouse, and also include cathedral  ceilings and other luxury perks. It’s part of the Los Gatos Union School District, which is a priority for many local home buyers.

Courtstyle sign

Courtstyle and Wimbledon Place both have the close proximity of the train tracks, an Wimbledon Place has the high voltage lines running down the middle of the main street, but Courtstyle is directly adjacent to the freeway, so there is an added noise issue there that probably explains, in part, why these homes are a little more affordable.

Built in 1984, the Courtstyle complex consists of 46 units, all 2 stories, all with 2 car attached garages.  Three units have 928 SF with 2 bedrooms and 1.5 bathrooms.   The rest are mostly 1626 SF, or 1842 SF , or 1856 SF with three bedrooms and two and one half baths, except one, which appears to have 3 full baths.  One unit is said to have 1,676 SF via the county records, but 1,800 SF when last reported on the MLS.  and 3 bedrooms, 2.5 baths.

These often have really good sized back yard for townhomes. It may be that this is the case since the units are more forward on the lots. The downside to that is many homes do not have a full sized driveway, and there’s not much landscaping or greenery in front.

Courtstyle and Wimbledon Place are both Planned Unit Developments, not condominiums (different type of ownership, not the type of architecture – see also

Courtstyle townhomes

The HOA dues are $580 as of this writing (perhaps less for smaller units) and that does include the roofs and a pool.

What are Courtstyle homes selling for now?

The 2 townhouses at Courtstyle which have sold and closed so far in 2018 have been purchased for about $1.3 million. This community generally sells for a bit less than Wimbledon Place as the homes are smaller and are closer to the freeway and train tracks.


Homes for sale & sold in last 24 months in Courtstyle and Wimbledon Place

Please browse listings of homes for sale or sold in the last two years below. Or view by map using this link.

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See all Courtstyle Wimbledon Place Courtside.
(all data current as of 4/14/2024)

Listing information deemed reliable but not guaranteed. Read full disclaimer.