3434 Woolsey Rd, Windsor, CA 95492
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Property image
OFF MARKET

3434 Woolsey Rd
Windsor, CA 95492

  • 5 Beds
  • 3.5 Baths
  • 5,800 sqft

$3,171,800

Trulia Estimate
as of Aug 24, 2026

$3,171,800

Trulia Estimate
as of Aug 24, 2026
  • 5 Beds
  • 3.5 Baths
  • 5,800 sqft

Home Highlights

Property Type
Single-Family Home
Living Area
5,800 sqft
Price/Sqft
$547
Parking
Attached Garage

Local Information

  • Map ViewExplore the area around 3434 Woolsey Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Available: August 30, 2024
Your friends will be clamoring for invitations to sip wine poolside while overlooking award-winning vineyards at this gorgeous property. Not only is it an easy commute to highway 101, Healdsburg or Santa Rosa, it has lots of room for family and friends. This California Tudor has been updated and features four bedrooms including a primary with a large ensuite bath as well as three additional bathrooms. In addition there is a home office/workout room. This is a lifestyle few get to enjoy and it is waiting in this furnished two story home.

short term lease option (3-6 mos) utilities at a capped amount. short term lease rate $10K/mo
Long term (12 mos) tenant pays all utilities
3434 Woolsey Rd, Windsor, CA 95492 is a 5 bedroom, 4 bathroom, 5,800 sqft single-family home. It last sold for $1,600,000 on Mar 11, 1997 (19,900% above the $8,000 asking price). More recently, it was listed as a rental in August 2024 with an asking price of $8,000 per month. That rental listing was removed on September 13, 2024. It is currently off market. The Trulia Estimate is $3,171,800, with a rent estimate of $7,814/month.

Home Details for 3434 Woolsey Rd

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 1 Year

Interior Features

Appliances & Utilities
DryerWasher
Room & Shared Space
Shared space is furnished

Exterior Features

Pool
Pool
Parking & Garage
Parking: Attached, On Site

Comparable Sales for 3434 Woolsey Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
2280 Olivet Ln, Santa Rosa, CA
0.37
Single-Family Home
$1,285,000
07/06/26
3
3
2,555 sqft
2875 Woolsey Road, Windsor, CA
0.78
Single-Family Home
$2,900,000
07/30/26
5
4
4,747 sqft
2487 Olivet Road, Santa Rosa, CA
0.53
Single-Family Home
$1,262,500
04/03/26
4
2
2,456 sqft
4020 Woolsey Road, Santa Rosa, CA
0.60
Single-Family Home
$825,000
11/21/25
2
2
1,156 sqft
1800 Gerhard Drive, Santa Rosa, CA
1.38
Single-Family Home
$1,360,000
03/20/26
5
3
2,320 sqft
2487 Woolsey Rd, Fulton, CA
1.18
Single-Family Home
$1,175,000
06/26/26
3
2
2,634 sqft
4022 Woolsey Road, Santa Rosa, CA
0.60
Single-Family Home
$759,000
04/06/26
2
1
928 sqft
1558 Olivet Road, Santa Rosa, CA
1.79
Single-Family Home
$1,481,585
10/07/25
3
2
2,516 sqft
1888 Judson Lane, Santa Rosa, CA
2.00
Single-Family Home
$1,200,000
01/06/26
4
3
2,335 sqft
2855 Fulton Road, Fulton, CA
1.99
Single-Family Home
$1,594,000
05/06/26
3
3.5
2,090 sqft

Nearby homes

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Around this home

What Locals Say about Santa Rosa

At least 1280 Trulia users voted on each feature.

  • 87 % Say it's dog friendly

  • 85 % Say there are sidewalks

  • 82 % Say car is needed

  • 74 % Say yards are well-kept

  • 73 % Say there's holiday spirit

  • 70 % Say parking is easy

  • 62 % Say streets are well-lit

  • 62 % Say people would walk alone at night

  • 61 % Say kids play outside

  • 60 % Say it's walkable to grocery stores

  • 59 % Say it's walkable to restaurants

  • 58 % Say neighbors are friendly

  • 56 % Say they plan to stay for at least 5 years

  • 54 % Say it's quiet

  • 50 % Say there's wildlife

  • 29 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Vasanders
    "This is a wonderful neighborhood for walking your dog. "
    1
    Flag
  • Meeyatt
    "Great access to public transportation"
    0
    Flag
  • Trulia User
    "There’s not much open space to run around and most yards are small"
    0
    Flag
  • Julcooney
    "Dogs are always on leashes, and you don’t hear dog barking in the neighborhood…"
    0
    Flag
  • Melissany920
    "Close knit Lots of families and pride of ownershio. Historic area, close to downtown and shopping, restaurants and entertainment"
    0
    Flag
  • Vasanders
    "We are new to the area but this seems like a safe and quiet neighborhood with lots of families and people out walking their dogs. "
    1
    Flag
  • Vasanders
    "I am recently retired and do not commute except from my house to the yoga studio which is about a mile, no traffic. "
    0
    Flag
  • Trulia User
    "I always see people walking their dogs on leash in the neighborhoods. There are breed restrictions to keep in mind. I wish apartments & landlords were more open to larger breeds "
    0
    Flag
  • Trulia User
    "Safe neighborhood to raise a family in and the park nearby Howarth is amazing. Spring Lake is also great for hiking. "
    0
    Flag
  • Pedro Castaneda
    "Every year there is more traffic and the road I live on is right off a main road so it’s difficult to get on main rd when there is a lot of traffic "
    0
    Flag
  • 7fnqhjf424
    "Backcountry roads winding through wine country. Half an hour morning commute double that coming home because of all the work trucks, cement mixer trucks, heavy dump trucks, farming equipment and clueless tourists. "
    0
    Flag
  • 6kxpb7c792
    "Dog owners don’t pick up their waste. Usually, the smaller the dog the less likely the owner thinks they should be a good person. Completely unacceptable."
    0
    Flag
  • Liz Jahren
    "We have lots of dogs! They need to be able to be kind. They must be on leash. Owners must pick up poop. "
    1
    Flag
  • Gianni3333
    "It’s great with lots of bike trails and nearby bus stops. There train stops down the street. Traffic is light most of the time. "
    1
    Flag
  • Irene.e.harrell
    "Downtown is super dog friendly with a lot of the restaurants having patios and dog friendly spaces. "
    0
    Flag
  • Dustin w.
    "i lived in this neighborhood for years. parking is a mess because no one uses their garage for cars. the houses are cheaply made and in terrible condition. it is a very safe neighborhood. there are stray cats everywhere to keep the rodent population under control. great location if you like to walk. "
    1
    Flag
  • Whitetreelucida
    "Friendly people beautiful nature Lots of cultural activities, yoga, music, gardening, heirloom, vegetables, cows, and horses. "
    0
    Flag
  • Trulia User
    "dogs bark alot but many are very sweet. people look out for another dogs aswell (if they go missing ect)"
    2
    Flag
  • Patti
    "Do not move to Santa Rosa it’s gross lots of homeless It’s scary at night there is lots of drugs and everyone cars guns in their cars and drugs too. Police do a good job though "
    0
    Flag
  • Ymkje Dioquino
    "We haven’t lived here long enough to know, but we’ve attended several fun events in the area! We especially the Sofa winterblast event:)"
    9
    Flag
  • Rrph9cpb5d
    "We enjoy weekly community prayer for our city at the town square, festivals, farmers markets, wineries and theatrical events. Many churches host weekly activities for highschoolers and junior highers."
    2
    Flag
  • Abbie Gubera
    "General awareness and kindness in our neighborhood. We have an island a family on our street has "adopted" to take care of which makes it like we have a private park"
    2
    Flag
  • Isabelle Garson
    "Work from home. When I commuted it was best to avoid rush hour and leave at 10 instead of 9 and 6 instead of 5."
    1
    Flag
  • Trulia User
    "The neighborhood is great, but the number of young families is diminishing. Cost of housing is too high for most young families. This is not good for sustaining good elementary schools and child-friendly spaces. Hope things turn around quickly or this area will be a 55+ community soon."
    5
    Flag
  • Abbie Gubera
    "all the nearby state parks, open space, amenities, grocery stores (gourmet) and the beauty of it with all the trees and vineyards"
    1
    Flag
  • Trulia User
    "Our area is nice, pretty clean and good schools. We had fires 5 years ago, the likelihood of it happening here again is pretty slim. Excellent grocery store, an a few restaurants and good stores. We have lived here for about 7 years. We have no desire to move. Also it easy access to freeway and shopping centers. And hospital and medical clinics. Farmers markets every Wednesday and Saturday. Excellent area for families and friends. 100 words are hard to come up with."
    0
    Flag
  • Trulia User
    "None it’s quiet nothing goes on around here except the basic living. That’s why I like this area simple Clean and everyone is respectful quiet and friendly "
    0
    Flag
  • Trulia User
    "I’ve lived in this area 6 years. People are friendly and courteous hen you see them. A good portion of the neighbors are good about keeping their places up and seems to be tidy. Several good stores and restaurants locally. "
    1
    Flag
  • Trulia User
    "I have a very short commute, I drive to work earlier than most of the traffic, and I drive my own vehicle "
    0
    Flag
  • Trulia User
    "we are right next to the fairgrounds. we can see fireworks, hear music and be first in line for events."
    6
    Flag
  • Trulia User
    "The Saturday and Wednesday farmers markets are wonderful. Just a few miles to Russian river resort area. The local airport is minutes away. Molesberry’s market, local pub and several restaurants. I love it. "
    0
    Flag
  • Cindy A
    "Santa Rosa can be a good place for families depending on the area. Smoke and fire season has made it a bit less nice ."
    0
    Flag
  • Sierra S.
    "Yes, it’s a great place to raise a family. Perfect weather and close to many amenities such as the ocean, Red forest and wine country. "
    1
    Flag
  • Suzanne J.
    "Remote, private, yet close to town. It’s clean, quiet, safe. I have nothing else to say, thus I’ll try to put the 100 characters here."
    0
    Flag
  • Kat R
    "I’ve lived in this neighborhood for 6 years and feel at home. It is easy to meet people and make friends. Also, close to regional parks ."
    0
    Flag
  • Melissa M.
    "Lived here 4 years. Nice established neighborhood mainly older population nice streets older well kept home. "
    0
    Flag
  • Grkalmar
    "I’ve lived here for three years. It’s not perfect, there is still a little bit of crime but it’s not that bad. I think it’s a great area for families."
    8
    Flag
  • Trulia User
    "There is too many homeless around Santa Rosa as of recent. We don't have the funding for everyone here as it is. "
    0
    Flag
  • Charvindavis1976
    "There are stores very close to me. The freeway is around the corner as well. So, when I get off work and need to pick something up for dinner before I go home, it’s very easy to handle. "
    0
    Flag
  • Allyssa C.
    "My husband and I love living in Santa Rosa, it’s safe for me to run & I want to raise my family here"
    1
    Flag

LGBTQ Local Legal Protections

Price and Tax history

DateEventPrice
Sep 13, 2024
Source: Zillow Rentals
ListingRemoved
$8,000
Aug 30, 2024
Source: Zillow Rentals
Listed For Rent
$8,000
Jul 27, 2024
Source: Zillow Rentals
ListingRemoved
Jun 11, 2024
Source: Zillow Rentals
Listed For Rent
$8,000
May 8, 2023
Source: Zillow Rentals
ListingRemoved

Frequently asked questions about 3434 Woolsey Rd

  • What is 3434 Woolsey Rd estimated to be worth?
    Trulia's estimated value for 3434 Woolsey Rd in Windsor, CA is $3,171,800.
  • What is the price history for 3434 Woolsey Rd?
    3434 Woolsey Rd in Windsor, CA last sold for $1,600,000 in March 1997.
  • Is Windsor a buyer's or seller's market?
    Windsor is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Windsor?
    The median sale price in Windsor is $727K. That is down $21.33K from the prior month.
  • Does 3434 Woolsey Rd have a pool?
    Yes, 3434 Woolsey Rd in Windsor, CA has a pool.
  • Does 3434 Woolsey Rd have laundry facilities?
    Yes, 3434 Woolsey Rd in Windsor, CA has in-unit laundry.

Homes for rent near 3434 Woolsey Rd

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Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.
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