3366 Woolsey Rd, Windsor, CA 95492
OFF MARKET

3366 Woolsey Rd
Windsor, CA 95492

  • 3 Beds
  • 3 Baths
  • 1,792 sqft (on 20 acres)

$1,875,900

Trulia Estimate
as of May 25, 2026
Est. Refi. Payment $11,185/mo*
Refinance Your Home

$1,875,900

Trulia Estimate
as of May 25, 2026
Est. Refi. Payment $11,185/mo*
Refinance Your Home
3 Beds
3 Baths
1,792 sqft
(on 20 acres)

Local Information

Map showing home location
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Commute Destination

Description

This single-family home is located at 3366 Woolsey Rd, Windsor, CA. 3366 Woolsey Rd is in Windsor, CA and in ZIP code 95492. This property has 3 bedrooms, 3 bathrooms and approximately 1,792 sqft of floor space. This property has a lot size of 20.00 acres and was built in 1983.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
No Info
Outdoor
No Info
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 3366 Woolsey Rd

Interior Features

Heating & Cooling
Heating: OtherHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1983
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 20.00 acres

Price History for 3366 Woolsey Rd

DatePriceEventSource
05/14/2008$1,800,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax$17,824
Assessment$1,506,106
Home facts updated by county records

Comparable Sales for 3366 Woolsey Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
2487 Olivet Road, Santa Rosa, CA
0.62
Single-Family Home
$1,262,500
04/03/26
4
2
2,456
4020 Woolsey Road, Santa Rosa, CA
0.70
Single-Family Home
$825,000
11/21/25
2
2
1,156
1800 Gerhard Drive, Santa Rosa, CA
1.18
Single-Family Home
$1,360,000
03/20/26
5
3
2,320
1288 Triple Oak Way, Fulton, CA
1.21
Single-Family Home
$1,250,000
07/10/25
3
2
1,884
1288 Triple Oak Way, Santa Rosa, CA
1.21
Single-Family Home
$1,250,000
07/10/25
3
2
1,884
1623 Willowside Road, Santa Rosa, CA
1.52
Single-Family Home
$1,600,000
03/26/26
2
2
1,000
4022 Woolsey Road, Santa Rosa, CA
0.69
Single-Family Home
$759,000
04/06/26
2
1
928
241 Royal Court, Santa Rosa, CA
1.28
Single-Family Home
$3,023,241
08/11/25
4
4
3,907
2290 Woolsey Road, Fulton, CA
1.42
Single-Family Home
$2,275,000
07/16/25
4
4
3,440
1757 Willowside Road, Santa Rosa, CA
1.19
Single-Family Home
$949,000
06/23/25
2
2
2,276

Nearby homes

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Assigned Schools

These are the assigned schools for 3366 Woolsey Rd.
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The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Santa Rosa

At least 1275 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 restaurants

  • 60 % Say it's walkable to grocery stores

  • 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

  • 30 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Melissany920
    "Close knit Lots of families and pride of ownershio. Historic area, close to downtown and shopping, restaurants and entertainment"
    0
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  • 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. "
    0
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  • 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
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  • 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
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  • Trulia User
    "Safe neighborhood to raise a family in and the park nearby Howarth is amazing. Spring Lake is also great for hiking. "
    0
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  • 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
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  • 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
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  • 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
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  • 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
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  • Irene.e.harrell
    "Downtown is super dog friendly with a lot of the restaurants having patios and dog friendly spaces. "
    0
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  • 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
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  • Whitetreelucida
    "Friendly people beautiful nature Lots of cultural activities, yoga, music, gardening, heirloom, vegetables, cows, and horses. "
    0
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  • 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
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  • 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
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  • 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
  • Patti
    "There are endless miles of trails for hiking, biking and running/ walking. Dogs are friendlier then the people."
    0
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  • 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
  • Peri Lyn Olsson
    "Dog poop is not always picked up and occasionally there are aggressive dogs. …………………………………………………………………"
    1
    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
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  • 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
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  • 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
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  • 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
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  • Caroline C.
    "I love it. Easily one of the best things about living in Sonoma County, my 4 mile "commute" from Santa Rosa to where I work in Rohnert Park, CA takes about 12 minutes. "
    0
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  • Caroline C.
    "Welcome to Casa Del Sol! We are a pet-friendly, family-based community where everyone, including dogs, enjoy taking a walk in beautiful Casa Del Sol. Our neighbors who own dogs help to protect it's beauty by leashing their pets and cleaning up after them. I can't think of one thing to not like!"
    0
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  • 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
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  • 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
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  • 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
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  • Melissa M.
    "Lived here 4 years. Nice established neighborhood mainly older population nice streets older well kept home. "
    0
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  • 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
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  • 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
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  • 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
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3366 Woolsey Rd, Windsor, CA 95492 is a 3 bedroom, 3 bathroom, 1,792 sqft single-family home built in 1983. This property is not currently available for sale. 3366 Woolsey Rd was last sold on May 14, 2008 for $1,800,000. The current Trulia Estimate for 3366 Woolsey Rd is $1,875,900.