1027 Westside Rd, Healdsburg, CA 95448
OFF MARKET

1027 Westside Rd
Healdsburg, CA 95448

  • 3 Beds
  • 3 Baths
  • 3,281 sqft (on 2.40 acres)

$3,280,000

Trulia Estimate
as of May 27, 2026
Est. Refi. Payment $19,518/mo*
Refinance Your Home

$3,280,000

Trulia Estimate
as of May 27, 2026
Est. Refi. Payment $19,518/mo*
Refinance Your Home
3 Beds
3 Baths
3,281 sqft
(on 2.40 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Come find peace and reflection, just minutes from Downtown Healdsburg. This magical modern estate on 2+ acres set among California's finest wineries was designed for entertaining and endless family fun. Blending the outdoors in with passive cooling stone walls and floor to ceiling windows that look out to serene views sprinkled with Heritage Oaks, wildflower walking paths and a sun filled area for "future'' pool. Bright open design flows seamlessly to the outdoor kitchen & grilling areas, built-in Hot Tub, Bocce court and commercial pizza oven. Main level Owner's Suite with spa bath, downstairs additional Bedroom & Guest Suite, Top of the line 1000 bottle refrigerated wine cellar accents the private home theater with wet bar plus loft area for a peaceful yoga retreat or office space. Cycle to nearby Dry Creek Valley and the Russian River AVAs featuring world class wine tasting and impeccable Michelin star dining. This is truly everything you could want for the wine country lifestyle. 2021-07-05
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
Garage
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 1027 Westside Rd

Interior Features

Heating & Cooling
Heating: RadiantAir ConditioningCooling System: CentralHeating Fuel: Radiant
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 8Types of Rooms: Dining Room
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 2011Year Updated: 2011
Property Type / Style
Property Type: Single Family HomeArchitecture: Contemporary

Exterior Features

Exterior Home Features
Exterior: Stucco, Wood
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Community

Units in Building: 1

Lot Information

Lot Area: 2.40 acres

Price History for 1027 Westside Rd

DatePriceEventSource
07/23/2021$2,820,000Sold
BAREIS #321045140
07/22/2021$2,850,000PendingBAREIS #321045140
07/08/2021$2,850,000ContingentBAREIS #321045140
06/29/2021$2,850,000Listed For SaleBAREIS #321045140
12/04/2020$2,950,000ListingRemovedAgent Provided
07/16/2020$2,950,000PriceChange
Agent Provided
06/16/2020$3,125,000Listed For SaleAgent Provided
03/17/2015$1,850,000Sold
BAREIS #21409616
12/05/2014$1,850,000ListingRemovedAgent Provided
08/13/2014$1,850,000PendingAgent Provided
07/09/2014$1,850,000PriceChange
Agent Provided
07/01/2014$1,995,000Listed For SaleAgent Provided
09/05/2008$475,000Sold
N/A
12/23/2002$135,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax$25,861
Assessment$2,247,841
Home facts updated by county records

Comparable Sales for 1027 Westside Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1039 Westside Road, Healdsburg, CA
0.29
Single-Family Home
$1,850,000
08/22/25
3
3.5
2,829
1019 Westside Road, Healdsburg, CA
0.12
Single-Family Home
$1,835,000
08/07/25
3
2.5
2,303
510 Westside Road, Healdsburg, CA
0.72
Single-Family Home
$1,900,000
05/29/25
3
2
1,500
426 Westside Rd, Healdsburg, CA
0.72
Single-Family Home
$1,600,000
09/16/25
3
2
1,882
699 Grove Street, Healdsburg, CA
1.03
Single-Family Home
$3,351,700
04/10/26
4
3
3,388
500 Westside Rd, Healdsburg, CA
0.66
Single-Family Home
$600,000
09/15/25
2
2
1,598
199 W Matheson Street, Healdsburg, CA
0.82
Single-Family Home
$950,000
12/24/25
3
1
1,260
980 Trentadue Way, Healdsburg, CA
1.30
Single-Family Home
$2,150,000
07/09/25
3
3
2,248
2859 Wallace Creek Road, Healdsburg, CA
1.25
Single-Family Home
$1,550,000
07/21/25
2
2
1,700
423 Matheson Street, Healdsburg, CA
1.49
Single-Family Home
$2,900,000
04/21/26
3
3
3,696

Nearby homes

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Assigned Schools

These are the assigned schools for 1027 Westside 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 Healdsburg

At least 97 Trulia users voted on each feature.

  • 96 % Say it's dog friendly

  • 88 % Say people would walk alone at night

  • 85 % Say there are sidewalks

  • 80 % Say yards are well-kept

  • 79 % Say there's holiday spirit

  • 78 % Say streets are well-lit

  • 75 % Say they plan to stay for at least 5 years

  • 73 % Say it's walkable to restaurants

  • 73 % Say car is needed

  • 73 % Say kids play outside

  • 70 % Say parking is easy

  • 66 % Say it's quiet

  • 66 % Say neighbors are friendly

  • 63 % Say there's wildlife

  • 62 % Say it's walkable to grocery stores

  • 56 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Melissa Langlois
    "Lots of neighborhood dog walking, all sidewalks, everyone is respectful with picking up after their dogs "
    0
    Flag
  • Whitteelucida
    "Good schools, concerned, parents, and safe playgrounds. A little isolated so trips to San Francisco or even Petaluma or Santa Rosa or Santa Rafael would be a good idea. "
    0
    Flag
  • Heather Cheda
    "Definitely! Always see people out walking with their dogs and playing with them in various parks. It’s a very dog friendly town. "
    0
    Flag
  • Whitney Lewis
    "Downtown has a grass area with a fountain that’s great for kids. Good schools. Good parks. The town feels very safe."
    0
    Flag
  • Jazmin A.
    "It’s very quiet and safe here. Lots of friendly people, hiking trails, community support. I love it here "
    0
    Flag
  • Abel M.
    "this is a really lovely place to live oft you want to retire or of you love the wine country and school district are really helpful "
    2
    Flag
  • Heather
    "We all know each other and look after one another. Nice, quiet, close knit community. Easy access to SF, the coast and other parts of CA"
    1
    Flag
  • Summerl0ve
    "Great neighborhood, close to parks, schools etc. with a neighborly feel & feeling of safety! I would feel comfortable having a loved one living in this neighborhood! "
    0
    Flag
  • Trulia User
    "Great place to raise kids. It’s a beautiful town and it’s got some of the best wine in the world. What’s not to love?"
    0
    Flag
  • Annette
    "Music in the Plaza, Saint Paddy’s day parade, Friday night art in the street, the lighting of the tree, and all the wonderful things they put on in the plaza throughout the year"
    1
    Flag
  • Trulia User
    "Safe and friendly neighbors make the children outgoing, funny and creative. We always have family fun events, inclusive to all cultures as well."
    0
    Flag
  • Sarah P
    "Its a nice place to live if you can afford it. Safe and inviting. Touristy but still has a local flair."
    0
    Flag
  • Fitch Mountain resident
    "I’m up the north side of Fitch mountain near Villa Chantecleer so a car or scooter is required. It’s only 12 minutes to the quaint Healdsburg plaza, 4 minutes to Big John and Garrett’s Ace hardware, and 15 to the upscale Oliver’s grocery store in Windsor. . "
    3
    Flag
  • Sarah P
    "Ive lived in Healdsburg most of my life. Live with a friend who boight her home in early 90.s. Nice neighbors. Walk my daughter to school. It has become a little pricey to live here but its worth it if you have the means."
    0
    Flag
  • Patti_poo22
    "holiday events on the town green. beautiful country scenery. elaborate dinners with friends with great local wine and food."
    0
    Flag
  • Kimzander83
    "I live here and love it the neighborhood is clean safe and friendly the homes are very nice inside the neighbors are fun and enjoy hanging out with one another "
    2
    Flag
  • Spencerchaffey
    "I’ve lived in this small town for two years, the people are friendly and communal. I love the lively atmosphere that permeates everywhere around the square. "
    1
    Flag
  • Brown
    "Healdsburg has a true sense of community, people say hello and during the week the pace is great. Weekends are different as there are many tourists."
    1
    Flag
  • Samanthacav
    "The people that live here and the bustling downtown make Healdsburg truly unique. There is a small town feel but you aren’t too far from a big city"
    1
    Flag
  • Candida
    "Weekend City feel, week day country feel. A community of participation. Bike, walk everywhere. Great Restaurants and Galleries. Movies and Theater, Tuesday Music on the Square, Great Farmers Market."
    1
    Flag

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1027 Westside Rd, Healdsburg, CA 95448 is a 3 bedroom, 3 bathroom, 3,281 sqft single-family home built in 2011. This property is not currently available for sale. 1027 Westside Rd was last sold on Jul 23, 2021 for $2,820,000. The current Trulia Estimate for 1027 Westside Rd is $3,280,000.