Westwood Highlands is a small single-family enclave on the southwest slope of Mount Davidson, in San Francisco's 94127 ZIP. Over the trailing 12 months of 2026 its median house sold for $2.58M, about 11% above the prior year, and the typical listing closed in under two weeks.
If you are searching "Westwood Highlands," you are almost certainly looking at houses, not condos, and you are trying to work out two things: what a home here actually costs, and whether the list prices you see online mean anything. I'm Chris Chour, founder and broker of EON Real Estate. Most of my work is single-family and condo transactions in San Francisco's higher-priced neighborhoods, and Westwood Highlands is one of the pockets where the gap between the list price and the sale price is wide enough to change how you write an offer. The neighborhood is almost entirely 1920s-to-1940s houses on quiet, curving streets, owner-occupied at a high 92.9% rate, according to Census data. That scarcity of available inventory, more than any single feature of any one house, is what sets the price. Unless otherwise noted, all market figures in this guide come from MLS data.
How to read the Westwood Highlands market
Start with the shape of the inventory. Of the 13 homes that closed in the neighborhood over the trailing 12 months of 2026, all 13 were single-family houses. There were no condos, no two-unit buildings, no TICs in the closed set. That matters because it means every comparable sale is genuinely comparable: you are pricing a house against other houses, not untangling a blended median that mixes a flat with a detached home. For a wider look at how the city's housing eras price differently, our guide to San Francisco home styles is a useful companion.
Next, weight the most recent sales most heavily. The last 30 days produced no closings at all, which is normal for a neighborhood this small. The trailing 90 days produced three sales at a $3.30M median, and the trailing 180 days produced five at a $2.70M median. Those recent windows ran above the full-year $2.58M median because the homes that happened to sell in them were larger, renovated and view-oriented. That is the first lesson of a thin market: a three-sale median swings hard on which three houses sold, so the 12-month median of $2.58M is the steadier number to anchor to, and the recent run tells you demand at the top of the range is real.
Finally, treat the list price as a marketing number, not a ceiling. The neighborhood's median price per square foot over the trailing 12 months was $1,190, and homes spent a median of 13 days on the market before closing. When inventory is this scarce and buyers this motivated, listing agents routinely price below the expected sale value to concentrate demand into a short window and draw multiple offers. The result is a set of closings that sit noticeably above where they started. Reading those two prices against each other is the single most useful skill in this neighborhood.
Westwood Highlands by the numbers
Here is the trailing-12-month picture as of October 2026, drawn from closed single-family sales inside the neighborhood.
Westwood Highlands by the numbers
For context, the citywide median sale price was $1.75M over the same window, a figure that blends houses with condos and multi-unit buildings. A single-family median of $2.58M puts Westwood Highlands roughly 47% above that citywide figure, which is less a statement about any one house than about what a detached home on a quiet block costs in this part of the city. If you want to see where the neighborhood sits against the top of the market, our ranking of San Francisco's richest neighborhoods gives the full field.
What drives the price spread
Closed sales over the trailing 12 months ran from $2.135M to $4.80M. That is a wide range for 13 houses, and four distinct levers explain almost all of it. Knowing which lever a given listing pulls tells you where its offer is likely to land.
Views
Westwood Highlands climbs the side of a hill, so some blocks look out over the ocean or the downtown skyline and some face into the slope. The highest price per square foot in the set, $1,346, belonged to a renovated house on the 400 block of Hazelwood Avenue with both city and water views. A home with no view on the same street traded lower on a per-foot basis despite a full renovation. View is the first thing I check when a Westwood Highlands listing comes out, because it moves the number more than square footage does.
Condition and renovation
Most of the recent high closings were fully renovated houses that kept their 1920s-to-1940s period shell. A remodeled kitchen and updated baths, plus a reconfigured primary suite, can lift a sale by hundreds of thousands of dollars over an unremodeled house of the same size. The flip side: a dated but structurally sound home on a good block is where a buyer willing to renovate finds the most room. These are houses built around 1938 at the neighborhood median, so renovation scope is a real variable, not a cosmetic one.
Size and bedroom count
Three-bedroom houses made up a little over half of the closed sales and carried a $2.70M median; four-bedroom houses were about 38% of sales at a $2.55M median. Counterintuitively, the three-bedroom median sat higher, because several of the three-bedroom sales were the renovated view homes while a couple of the larger houses were unremodeled or awkwardly laid out. Square footage sets the floor of a valuation here, not the ceiling.
Parking and outdoor space
Garage parking is close to universal in this housing era, but the number of spaces and the usability of the yard still move offers. On a hill, a level or usable rear garden is scarcer than the house count suggests, and buyers pay for it. When you compare two listings at a similar price, the parking count and the outdoor space are often the tiebreaker.
What a recent sale looked like
Consider 477 Hazelwood Avenue, a three-bedroom, four-bath house of 2,593 square feet that closed in August 2026. It came on the market at $2.395M and closed eight days later at $3.49M, about 46% over its asking price, which worked out to $1,346 per square foot, the highest in the neighborhood's trailing-12-month set. The drivers were exactly the ones above: a renovated interior, two-car parking, and a sweep of city and water views.
Now set it beside 221 Cresta Vista Drive, a larger four-bedroom, five-bath house of 3,300 square feet. It listed at $2.325M and took 119 days to sell, finally closing in July 2026 at $2.25M, slightly under its asking price. More space, lower price, and far more time on the market. The difference was not the square footage; it was the combination of view, condition, and how the home was priced and presented. When I run a Westwood Highlands comp set for a buyer, this is the pairing I show them first, because it demolishes the assumption that the biggest house or the lowest price per foot is the best value. In this neighborhood, the renovated view home that looks expensive on paper often closes faster and competes harder than the larger fixer down the street. For a sense of how long an offer-to-close timeline runs once you are in contract, see our guide to how long the buying process takes.
What to consider before you buy here
This is the part most neighborhood write-ups skip, so I will be direct about the tradeoffs.
The list price tells you almost nothing
Because strategic underpricing is the norm, the asking price is a starting gun, not a guide to value. Several homes closed 45% to 55% above list over the past year. If you anchor your budget to list prices, you will lose every competitive house and conclude the market is irrational. It is not; you are reading the wrong number. Build your budget off recent closed prices per square foot, adjusted for view and condition, and treat the list price as marketing.
Inventory is thin and sporadic
Thirteen sales in a year is roughly one a month, and the last 30 days had none. You may wait weeks for a home that fits, then face three other offers when it appears. The fall selling season tends to bring a cluster of listings, but there is no steady pipeline. Patience and a pre-approved, decisive offer matter more here than in a higher-turnover neighborhood.
Topography and transit are real constraints
The neighborhood earns a 62 Walk Score and a 63 Transit Score, both in the middle of the range. The Muni 43 Masonic bus runs along its edges, but there is no rail stop inside the neighborhood, and the hillside means some errands that look close on a map are a steep climb on foot. If a short walk to a train is near the top of your list, test the specific block before you fall for the house.
Is Westwood Highlands an expensive area?
Yes, and over the trailing 12 months of 2026 the median single-family home in Westwood Highlands sold for $2.58M, roughly 47% above the $1.75M citywide median that blends every property type. Recent closings have ranged from $2.135M to $4.80M, and the median price per square foot was $1,190. It is a high-priced, detached-home neighborhood with no lower-cost condo tier to pull the median down.
Where is Westwood Highlands in San Francisco?
As of 2026, Westwood Highlands sits in south-central San Francisco in the 94127 ZIP, on the southwest slope of Mount Davidson, bordering the Sunnyside and Miraloma Park areas. Its homes cluster on streets like Hazelwood Avenue, Brentwood Avenue, and Cresta Vista Drive. Mount Davidson Park forms the open-space edge on its north side, and Monterey Boulevard anchors the retail and bus service along the southern border.
Are home prices in Westwood Highlands going up or down?
Prices are up: the median single-family sale price rose about 11% over the trailing 12 months of 2026 versus the prior year, from roughly $2.325M to $2.58M, and median price per square foot climbed about 9% over the same period. The sample is small, 13 sales against four a year earlier, so read the trend as firmly positive rather than precise. Demand at the renovated, view-home end of the range has been the strongest.
How fast do homes sell in Westwood Highlands?
Fast, with a 13-day median time on the market over the trailing 12 months of 2026, and several homes sold in under a week. One house closed in zero days, and another in four. The exception was a larger home that sat 119 days before closing slightly under its list price, which pulled the average up to 19 days. Well-priced, renovated houses here are typically under contract within two weeks.
Why do Westwood Highlands homes sell over the asking price?
Because in 2026 list prices here are set below expected value on purpose, and several Westwood Highlands houses closed 45% to 55% over asking, including one that went from a $2.395M list to a $3.49M sale. With roughly one home selling a month and strong buyer demand, listing agents price low to concentrate offers into a short window. The over-asking result is a feature of the pricing strategy, not a sign the home was a bargain.
What is the cost of a home in Westwood Highlands?
As of the trailing 12 months of 2026, expect a single-family house to cost around $2.58M at the median, with most sales between $2M and $3M and a renovated view home reaching into the $3M to $4.8M range. At a median of $1,190 per square foot, a typical 2,500-square-foot house pencils close to $3M. Budget off recent closed prices, not list prices, which run well below the final number.
Talk to me about Westwood Highlands
When you are ready to look at Westwood Highlands, I can pull the block-specific comp set, separate the renovated view homes from the fixers, and show you what each one is likely to actually close at rather than what it is listed at. That one exercise is usually the difference between writing a winning offer and chasing the market. Reach out and we will start with the houses that fit your budget read the right way.
