1335 Winona Dr, San Jose, CA 95125
OFF MARKET

1335 Winona Dr
San Jose, CA 95125

Willow Glen
  • 4 Beds
  • 3 Baths
  • 2,408 sqft (on 0.26 acres)

$2,699,100

Trulia Estimate
as of Jul 20, 2026
Est. Refi. Payment $16,287/mo*
Refinance Your Home

$2,699,100

Trulia Estimate
as of Jul 20, 2026
Est. Refi. Payment $16,287/mo*
Refinance Your Home
4 Beds
3 Baths
2,408 sqft
(on 0.26 acres)

Local Information

  • Map ViewExplore the area around 1335 Winona Dr.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

This single-family home is located at 1335 Winona Dr, San Jose, CA. 1335 Winona Dr is in the Willow Glen neighborhood in San Jose, CA and in ZIP code 95125. This property has 4 bedrooms, 3 bathrooms and approximately 2,408 sqft of floor space. This property has a lot size of 0.26 acres and was built in 1962.
1335 Winona Dr, San Jose, CA 95125 is a 4 bedroom, 3 bathroom, 2,408 sqft single-family home in Willow Glen, built in 1962. It is currently off market. The Trulia Estimate is $2,699,100, with a rent estimate of $6,294/month.

Home Highlights

Parking
Garage
Outdoor
No Info
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 1335 Winona Dr

Interior Features

Heating & Cooling
Heating: OtherHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 1
Interior Details
Number of Rooms: 8
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1962Year Updated: 1962
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: 0.26 acres

Market trends in Willow Glen

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.84M
$19.92KMoM
Sale-to-List Price
103.7%
0.5%MoM
Price per sq ft
$1.09K
$22MoM
Available listings
183
10MoM
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Property Tax and Assessment

Year2025
Tax$11,480
Assessment$829,689
Home facts updated by county records

Comparable Sales for 1335 Winona Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1355 Robsheal Dr, San Jose, CA
0.12
Single-Family Home
$2,850,000
07/10/26
4
2.5
2,658
1369 Dry Creek Rd, San Jose, CA
0.18
Single-Family Home
$2,600,000
07/01/26
4
2.5
2,701
1351 Robsheal Dr, San Jose, CA
0.12
Single-Family Home
$3,200,000
04/17/26
3
2.5
2,412
1834 Hicks Ave, San Jose, CA
0.23
Single-Family Home
$2,360,000
08/15/25
4
3
2,450
1736 Wilcox Way, San Jose, CA
0.10
Single-Family Home
$2,299,950
05/07/26
3
2.5
2,036
1806 Cottle Ave, San Jose, CA
0.17
Single-Family Home
$3,550,000
02/23/26
4
3.5
2,595
1413 Robsheal Dr, San Jose, CA
0.28
Single-Family Home
$4,300,000
06/25/26
4
3
3,102
1727 Marlyn Way, San Jose, CA
0.19
Single-Family Home
$2,675,000
03/05/26
4
2
1,986
1538 Cherry Ave, San Jose, CA
0.26
Single-Family Home
$2,755,000
05/18/26
4
2.5
2,311
1552 Peregrino Way, San Jose, CA
0.38
Single-Family Home
$857,500
12/23/25
4
3
2,845

Nearby homes

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Assigned Schools

These are the assigned schools for 1335 Winona Dr.
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

Willow Glen
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Willow Glen

At least 670 Trulia users voted on each feature.

  • 95 % Say there are sidewalks

  • 93 % Say it's dog friendly

  • 79 % Say car is needed

  • 78 % Say there's holiday spirit

  • 74 % Say it's walkable to restaurants

  • 71 % Say yards are well-kept

  • 69 % Say it's walkable to grocery stores

  • 67 % Say parking is easy

  • 67 % Say people would walk alone at night

  • 65 % Say it's quiet

  • 65 % Say kids play outside

  • 60 % Say streets are well-lit

  • 58 % Say they plan to stay for at least 5 years

  • 58 % Say neighbors are friendly

  • 41 % Say there are community events

  • 39 % Say there's wildlife

Sourced by Trulia users. Learn more about our methodology.
  • Carnation Salinas
    "I lived in Willow Glen for 19 years, I also was raised in this area and went to the school’s here. It has been a great privilege being able to be around the community. It offers some great places and opportunities for single, families, and friends to share a meaningful connection conversations, making new friends, having meals, dancing on the avenue, music, crafts, biking, baking and so very much more all in one place, Christmas is the best time of the year, especially when you’re neighbors go all out and decorate the whole community, and people from all over come to see all the lights and decorations and the ambiance of the city (Willow Glen)within a city . It’s a beautiful and unique place, when you get a chance you have to come and see all the things going on in the neighborhood that I have always enjoyed. Be Blessed and Enjoy your time here!"
    0
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  • Sai Manish Reddy Nandyala
    "Quiet streets and nearby parks are great, but limited dog-friendly cafes and few off-leash areas nearby options."
    0
    Flag
  • Trulia User
    "Willow Glen is like a small close knit town inside a big city. Lots of neighborhood traditions and events. Good local schools. "
    0
    Flag
  • Michael Amaya
    "Some events that make our neighborhood special are Children learning events, Farmers markets, protests, etc. "
    0
    Flag
  • Tad
    "It's a nice small community, ppl walk at night, very quiet community. People are every nice, it's really nice at night specially during summer and fall. "
    0
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  • Laura Hughes
    "Everyone has a dog, and people love to greet your dogs in stores. Water bowls are everywhere! You meet so many people just for having dog friends."
    0
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  • Caleb Morris
    "Lovely place to live. Walkable. Nice restaurants. Safe. Wish there was public transit. We walk our dog here a lot. Good parks. Live close to Lincoln if you can!"
    0
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  • Trulia User
    "This a perfect place for families and great location fir kids and pets. Great wild life, walking distance to park, church and movies, and 24 hrs gym and food."
    0
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  • Trulia User
    "Every Christmas every house decorates and places a tree in front of their house. You can walk up the hill to the church events and just to hike and e joy the sunset."
    0
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  • Trulia User
    "I lived in the neighborhood for 7 years and would consider it one of the best and most charming neighborhoods in Silicon Valley! Walking and biking distance to most I need and overall a great community!"
    11
    Flag
  • Trulia User
    "Neighborhood book corner boxes, eveeyone dresses up thier house for holiday, lots of areas to walk a dog, hikes, deog groomers, shops and movie theatre near in walking distance."
    2
    Flag
  • Trulia User
    "My neighborhood is mostly quiet and only two miles from downtown, where I work. Good mix of houses and appartment or condos."
    1
    Flag
  • Trulia User
    "great transportation near by great schools grocery stores near by and light rail close everyone is nearby "
    1
    Flag
  • Trulia User
    "it's just a good area better than most and neighbors are friendly schools are close by and lots of nice restaurants "
    1
    Flag
  • Trulia User
    "it's an old, little, upgraded town, that has changed downtown to a nice place to take a walk on main st. they have so many variety of stores, coffee shops, ice cream parlors, jamba juice, restaurants, and a pet store."
    5
    Flag
  • Trulia User
    "I love my neighborhood. It’s a mile away from Caltrain, there’s a bus stop right outside the complex and restaurants, pharmacy, stores are within walking distance"
    0
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  • Trulia User
    "This is a nicer part of San Jose, but the crime and traffic have Increased exponentially. It was once a very connected and safe community, but no more."
    0
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  • Trulia User
    "Lots of parks to run and play, and neighbourhood streets to explore. Friendly environment. Plenty of other dogs"
    1
    Flag
  • Trulia User
    "many pups everywhere. and dog parks. anyone with a dog would like here. people walk at all times of day"
    0
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  • Trulia User
    "There is a neighborhood yearly potluck. Holidays are always fun with many homes decorated for Halloween, Christmas and even Easter. "
    0
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  • Trulia User
    "dogs r welcome and people are super friendly to eachother. however, have packages delivered to your side gate or elsewhere because although neighbors are friendly and it's a great neighborhood, not a gated community, thieves like to cruise the neighborhood for any packages left outside in plain sight. "
    0
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  • Trulia User
    "most of the people are friendly. stand up social, caring people. everything is at walking distance.very quiet peaceful neighborhood"
    1
    Flag
  • Trulia User
    "The community i wonderful. Good achocolatada and nearby restaurants.The streets have Christmas trees lined during the season. I’m certain areas the residents will have to interview you to make sure you’re the right fit."
    0
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  • Trulia User
    "There are friendly neighbors, some people feel a little too safe where they feel they don't have to worry or notice when strangers pass through. there is great school optional things for kids families to do"
    0
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  • Trulia User
    "Great for families and young professionals without children. Trees and houses are beautiful and well kept. Awesome for running and walking. Overall amazing place to live. "
    0
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  • Trulia User
    "beautiful neighborhood, but way too close to homeless encampment. there is a very thin line between wealthy and poor. schools are gradually declining."
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  • Trulia User
    "I have lived in the neighborhood for 8.5 years. I love my neighbors, I feel safe walking my dog at night. "
    0
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  • Beatrice H. T.
    "Parks nearby. Clean and safe environment for family life. It is a convenient location where you can drive to highway 280 or take public transportation to San Jose city center"
    6
    Flag
  • Nina S.
    "I am only a 3 minute drive from work, so it is extremely convenient for me. I also prefer to walk most of the time and I can get to work, grocery stores, my pharmacy, medical professionals, and many more within an hour of walking. I feel save enough to walk on my own as well, but I would still need a dog while walking at night. My neighbors are amazing and I love the community."
    3
    Flag
  • Brent F.
    "We have an annual summer street party, and holiday tree decorating for Christmas. This is a lovely place to live."
    2
    Flag
  • Jennifer S.
    "We’ve been here over two years and love it very much. It feels safe and neighborly. We especially love Halloween and checking out everyone’s displays."
    10
    Flag
  • Tani H.
    "access to freeway is quick, not a lot of congestion that I've had to deal with so far in both directions."
    1
    Flag
  • Lisamacwillowglen
    "Great place to raise kids. Tree lined streets. Main a street with great restaurants. Block parties, good schools."
    1
    Flag
  • Alexandra.balbierz
    "Lots of sidewalks for long walks. Not a lot of walking-distance parks, though. But lots of dogs in the neighborhood, regardless!"
    1
    Flag
  • Veronica83pinkcake
    "I live here for four years and I love my neighborhood, schools are close and stores and public transportations"
    8
    Flag
  • Brent F.
    "Dogs are welcome everywhere I go in Willow Glen. Owners are respectful, and all of the dogs I encounter are well behaved."
    1
    Flag
  • Brianklittle
    "Very child friendly. Nice neighbors. Parks are close by. Lots of kids between 8 - 14 years of age. "
    0
    Flag
  • Ameliav
    "The trees in front of the houses every Christmas. Clean-up days and Halloween’s and pretty much any other Holiday."
    1
    Flag
  • Erika S.
    "Potlucks, dinner parties, communal Halloween trick or treating, dog owner get togethers, start of summer parties"
    0
    Flag
  • Lauren M.
    "Neighborhood holiday spirit, the cable cars go through the neighborhoods around Christmas time. I feel safe walking my dog around the well lit neighborhoods. "
    1
    Flag

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Homes for sale near 1335 Winona Dr

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Off Market Homes Near 1335 Winona Dr

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