Healdsburg, CA Homes

• 

  

  

  /32

  $1,795,000

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft

  10957 Westside Rd, Healdsburg, CA 95448

  Off-Grid Oasis | 75+/- Acres of Serenity & Self-Sufficiency. Escape to this rare 75-acre off-grid sanctuary with sweeping views of Black Mountain and beyond. Designed for sustainable, multi-family living, the property features a spacious main home with an open floor plan, large view deck, and BBQ area ideal for outdoor entertaining. A separate guest house offers privacy for visitors or extended

  

  Heidi Faulkner

  Artisan Sotheby's Int'l Realty

  

  10957 Westside Rd, Healdsburg, CA 95448
• Explore Healdsburg

• 

  

  

  /33

  Starting at $2,176 Per Month

  • 1 - 3 Beds

  80 Dovetail Ln, Healdsburg, CA 95448

  Exceptional Location. Affordable Opportunity. Bowman Place offers the rare combination of a premier location and affordable housing. Surrounded by upscale hotels, acclaimed restaurants, and everyday conveniences, residents can enjoy a connected lifestyle in one of the area's most desirable neighborhoods. At a time when housing costs continue to challenge working households, Bowman Place

  Bowman Place

  

  80 Dovetail Ln, Healdsburg, CA 95448
• 

  $795,000

  Sold Aug 26, 2026

  362 Piper St, Healdsburg, CA 95448

  • 2 Beds
  • 1.5 Baths
  • 1,180 Sq Ft
  • Built 1993

  Last Sold Summary

  • 9% Below List Price
  • $674/SF
  • 88 Days On Market

  Current Estimated Value $835,049

  Last Listing Agent Emily Martin Healdsburg Sotheby's Int'l Realty

  

  362 Piper St, Healdsburg, CA 95448
• 

  Not Listed For Sale

  2011 Madrone Ave, Healdsburg, CA 95448

  • 2 Beds
  • 1 Bath
  • 614 Sq Ft
  • Built 1953

  

  2011 Madrone Ave, Healdsburg, CA 95448

  Last Sold Summary

  • 194 Days On Market

  Last Listing Agent Mike Downes Vanguard Properties
• 

  

  

  /45

  $450,000

  $25K PRICE DROP

  • Land
  • 72.7 Acres
  • $6,190 per Acre

  11311 Pine Flat Rd, Healdsburg, CA 95448

  HEALDSBURG, CA A sprawling 72-acre parcel of land at 11311 Pine Flat Road has been listed for sale, offering a rare opportunity to create a private sanctuary amidst the rolling hills of Sonoma County. With a diverse landscape of open meadows and mature timber, this property presents a blank canvas for a variety of ventures, from a grand estate home with breathtaking views to a tranquil

  

  Yovany Acosta

  11311 Pine Flat Rd, Healdsburg, CA 95448
• 

  

  /20

  $13,239

  Total Monthly Price

  • 3 Beds
  • 3 Baths
  • 2,615 Sq Ft
  • 870 Fitchview Lane-SI ID1538705P

  870 Fitch View Ln Unit SI ID1538705P, Healdsburg, CA 95448

  The advertised rate of $13,239/month is the lowest available price, based on a 30 day(s) stay with a move-in date of January 3, 2027. Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

  870 Fitchview Lane-SI ID1538705P

  870 Fitch View Ln Unit SI ID1538705P, Healdsburg, CA 95448
• 

  $515,000

  Sold Aug 05, 2026

  779 Bob Crosby Way, Windsor, CA 95492

  • 1 Bed
  • 1 Bath
  • 707 Sq Ft
  • Built 1999

  Last Sold Summary

  • 6% Below List Price
  • $728/SF
  • 46 Days On Market

  Current Estimated Value $541,106

  Last Listing Agent Elaine Nealley Coldwell Banker Realty

  

  779 Bob Crosby Way, Windsor, CA 95492
• 

  Est $2,706,514

  Not Listed For Sale

  9512 W Dry Creek Rd, Healdsburg, CA 95448

  • 2 Beds
  • 2 Baths
  • 1,365 Sq Ft
  • Built 1908

  

  9512 W Dry Creek Rd, Healdsburg, CA 95448

  Last Sold Summary

  • 128 Days On Market

  Last Listing Agent Eric Drew Healdsburg Sotheby's International Realty
• 

  

  /95

  $13,500,000

  • 4 Beds
  • 4.5 Baths
  • 4,858 Sq Ft

  437 W Dry Creek Rd, Healdsburg, CA 95448

  Located just minutes from downtown Healdsburg, this stunning architectural Wine Country estate crowns 20 acres at the gateway to Dry Creek Valley. A scenic drive leads to a dramatic arrival courtyard framed by fountains and gardens designed by Roche + Roche Landscape Architects. Masterfully designed by acclaimed architect Jeffrey Trapold and built in 2008 by award-winning builder JMA Jim Murphy &

  Graham Sarasy Healdsburg Sotheby's Int'l Realty

  

  437 W Dry Creek Rd, Healdsburg, CA 95448
• 

  

  /24

  $8,788

  Total Monthly Price

  • 3 Beds
  • 2 Baths
  • 1,603 Sq Ft
  • Condo for Rent

  600 Dry Creek Rd Unit SI ID1538716P, Healdsburg, CA 95448

  The advertised rate of $8,788/month is the lowest available price, based on a 1 month(s) and 2 day(s) stay with a move-in date of February 8, 2027. Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed

  600 Dry Creek Rd Unit SI ID1538716P, Healdsburg, CA 95448
• 

  $1,685,000

  Sold Oct 24, 2025

  14771 Mcdonough Heights Rd, Healdsburg, CA 95448

  • 3 Beds
  • 2 Baths
  • 1,729 Sq Ft
  • Built 1954

  Last Sold Summary

  • $975/SF
  • 14 Days On Market

  Current Estimated Value $1,629,976

  Last Listing Agent Grace Lucero Vanguard Properties

  

  14771 Mcdonough Heights Rd, Healdsburg, CA 95448
• 

  Est $959,217

  Not Listed For Sale

  619 Larkspur Dr, Healdsburg, CA 95448

  • 3 Beds
  • 2.5 Baths
  • 1,492 Sq Ft
  • Built 2013

  

  619 Larkspur Dr, Healdsburg, CA 95448

  Last Sold Summary

  • 49 Days On Market

  Last Listing Agent John Dayton Dayton & Tremont Real Estate
• 

  

  /35

  $829,000

  • 5 Beds
  • 5 Baths
  • 2,415 Sq Ft

  2252 W Dry Creek Rd, Healdsburg, CA 95448

  New co-ownership opportunity: Own one-eighth of this turnkey home, professionally managed by Pacaso. The Hollow occupies 3.3 acres on West Dry Creek Road in Healdsburg, where the H-shaped single-level floor plan and distinctive butterfly roof give the property an architectural identity that stands apart in Dry Creek Valley. The sustainable design integrates natural materials and passive light

  Maxx Rifkin Pacaso Inc

  

  2252 W Dry Creek Rd, Healdsburg, CA 95448
• 

  

  /49

  $27,381

  Total Monthly Price

  • 4 Beds
  • 4 Baths
  • Condo for Rent

  2234 Lytton Springs Rd Unit SI ID1538722P, Healdsburg, CA 95448

  The advertised rate of $27,381/month is the lowest available price, based on a 30 day(s) stay with a move-in date of January 4, 2027. Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

  2234 Lytton Springs Rd Unit SI ID1538722P, Healdsburg, CA 95448
• 

  $150,000

  Sold Mar 30, 2026

  0 None, Healdsburg, CA 95448

  • Land
  • 8 Acres
  • $18,750 per Acre

  Last Sold Summary

  • 23% Below List Price
  • 81 Days On Market

  Current Estimated Value $859,667

  Last Listing Agent Eric Drew Healdsburg Sotheby's International Realty

  

  0 None, Healdsburg, CA 95448
• 

  Est $1,201,304

  Not Listed For Sale

  5750 Palmer Creek Rd, Healdsburg, CA 95448

  • 3 Beds
  • 2 Baths
  • 2,041 Sq Ft
  • Built 2002

  

  5750 Palmer Creek Rd, Healdsburg, CA 95448

  Last Sold Summary

  • 9 Days On Market

  Last Listing Agent David Hunt Sonoma Realty Group
• 

  

  /63

  $4,250,000

  $250K PRICE DROP

  • 4 Beds
  • 6 Baths
  • 3,142 Sq Ft

  22200 Puccioni Rd, Healdsburg, CA 95448

  Set amidst approximately 25 picturesque acres in the heart of Healdsburg wine country, this exceptional gated estate offers an unparalleled blend of luxury, recreation, and agricultural beauty. Designed for those who appreciate the Sonoma County lifestyle, the property combines vineyard living, resort-inspired amenities, and thoughtfully curated outdoor spaces into one remarkable offering. The

  Kellie Larson Luxe Places International

  

  22200 Puccioni Rd, Healdsburg, CA 95448
• 

  

  /23

  $4,507

  Total Monthly Price

  • 1 Bed
  • 1 Bath
  • 893 Sq Ft
  • Condo for Rent

  9410 Chalk Hill Rd Unit SI ID1538699P, Healdsburg, CA 95448

  The advertised rate of $4,508/month is the lowest available price, based on a 30 day(s) stay with a move-in date of January 10, 2027. Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

  9410 Chalk Hill Rd Unit SI ID1538699P, Healdsburg, CA 95448
• 

  $945,000

  Sold Feb 24, 2026

  1158 Hillside Dr, Healdsburg, CA 95448

  • 2 Beds
  • 2 Baths
  • 1,135 Sq Ft
  • Built 1977

  Last Sold Summary

  • $833/SF
  • 4 Days On Market

  Current Estimated Value $940,934

  Last Listing Agent Michael Tremont Dayton & Tremont Real Estate

  

  1158 Hillside Dr, Healdsburg, CA 95448
• 

  Est $5,677,000

  Not Listed For Sale

  650 S Fitch Mountain Rd, Healdsburg, CA 95448

  • 3 Beds
  • 3 Baths
  • 3,483 Sq Ft
  • Built 1930

  

  650 S Fitch Mountain Rd, Healdsburg, CA 95448

  Last Sold Summary

  • 32 Days On Market

  Last Listing Agent Chad Verbish Vanguard Properties
• 

  

  /51

  $1,995,000

  • 2 Beds
  • 2 Baths
  • 1,280 Sq Ft

  317 Alexander Valley Rd, Healdsburg, CA 95448

  Set on approximately 4.62 acres along desirable Alexander Valley Road, this versatile wine country property offers a rare combination of usable land, multiple living spaces, and functional improvements. The mostly level parcel features a small old vine Zinfandel vineyard with room for potential expansion, along with ample space for gardens, animals, or additional agricultural use. The main

  Kellie Larson Luxe Places International

  

  317 Alexander Valley Rd, Healdsburg, CA 95448
• 

  

  /20

  $14,516 Per Month

  • 3 Beds
  • 2.5 Baths
  • Condo for Rent

  3245 W Dry Creek Rd Unit SI ID1604785P, Healdsburg, CA 95448

  The advertised rate of $14,516/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 24, 2026. Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can

  3245 W Dry Creek Rd Unit SI ID1604785P, Healdsburg, CA 95448
• 

  $3,045,000

  Sold Apr 15, 2026

  9981 W Dry Creek Rd, Healdsburg, CA 95448

  • 3 Beds
  • 2.5 Baths
  • 3,344 Sq Ft
  • Built 2003

  Last Sold Summary

  • $911/SF
  • 324 Days On Market

  Current Estimated Value $3,027,374

  Last Listing Agent Alain-Martin Pierret Compass

  

  9981 W Dry Creek Rd, Healdsburg, CA 95448
• 

  Est $1,733,749

  Not Listed For Sale

  5377 Dry Creek Rd, Healdsburg, CA 95448

  • 3 Beds
  • 2 Baths
  • 2,333 Sq Ft
  • Built 1993

  

  5377 Dry Creek Rd, Healdsburg, CA 95448

  Last Sold Summary

  • 29 Days On Market

  Last Listing Agent Grace Lucero Vanguard Properties
• 

  

  /31

  $759,000

  $20K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,280 Sq Ft

  333 Orangewood Dr, Healdsburg, CA 95448

  A completely reimagined single-story home in Healdsburg's most sought-after 55+ community, and one of the best options in the market for Wine Country living. Positioned to face open space, every detail has been thoughtfully updated high-end flooring, crown molding, custom fireplace, remodeled kitchen with new appliances, wine bar with built-in refrigerator, and remodeled bathrooms. New windows,

  Ryan Styles Engel & Volkers Sonoma

  

  333 Orangewood Dr, Healdsburg, CA 95448
• 

  

  /18

  $2,950 Per Month

  • Studio
  • 1 Bath
  • 450 Sq Ft
  • House for Rent

  8330 Chalk Hill Rd, Healdsburg, CA 95448

  Property Id: 973068 Stunning views of vineyards and sun sets await you at this paradise on top of a hill. Fully furnished one king bedroom, bathroom, and sitting area along with a kitchenette with access to washer dryer. Gorgeous furnishings that are brand new. High speed free STARLINK for wifi included! Secure location adjoining a large home in a gated estate. EMAIL TODAY FOR

  8330 Chalk Hill Rd, Healdsburg, CA 95448
• 

  $650,000

  Sold Mar 13, 2026

  147 Quarry Ridge, Healdsburg, CA 95448

  • 3 Beds
  • 1.5 Baths
  • 1,484 Sq Ft
  • Built 2000

  Last Sold Summary

  • $438/SF
  • 28 Days On Market

  Current Estimated Value $654,038

  Last Listing Agent Shannan Luft Coldwell Banker Realty

  

  147 Quarry Ridge, Healdsburg, CA 95448
• 

  Not Listed For Sale

  11988 Windy Hollow Ln, Healdsburg, CA 95448

  

  11988 Windy Hollow Ln, Healdsburg, CA 95448

  Last Sold Summary

  • 62 Days On Market

  Last Listing Agent Jonathan Bruington W Real Estate
• 

  

  /35

  $740,000

  • 4 Beds
  • 4 Baths
  • 3,129 Sq Ft

  6165 W Dry Creek Rd, Healdsburg, CA 95448

  New co-ownership opportunity by Pacaso: Own one-eighth this professionally managed, turnkey home. Olive Grove is set along a private driveway on West Dry Creek Road in Healdsburg, where ancient olive and fruit trees frame the approach to a renovated hillside compound. The board and batten exterior with a metal roof reads as modern and grounded against the surrounding hillside, with a main

  Maxx Rifkin Pacaso Inc

  

  6165 W Dry Creek Rd, Healdsburg, CA 95448
• 

  

  /72

  $15,500 Per Month

  • 3 Beds
  • 3.5 Baths
  • 2,197 Sq Ft
  • House for Rent

  705 Chiquita Rd, Healdsburg, CA 95448

  Ideally located right outside the Healdsburg City limits, just 2 miles from the Plaza! This recently remodeled 3 bedroom home features a large Great Room with cathedrals ceilings & picturesque gas fireplace. There are picture windows and doors throughout that bring the outside in. The home sits on 3 acres among beautiful heritage oak trees that can be seen from every room. French doors from the

  Tatiana Mcwilliams Live Wine Country

  

  705 Chiquita Rd, Healdsburg, CA 95448
• 

  $9,400,000

  Sold Jun 16, 2026

  13000 Los Amigos Rd, Healdsburg, CA 95448

  • Land
  • 1,260.42 Acres
  • $7,458 per Acre

  Last Sold Summary

  • 111 Days On Market

  Last Listing Agent Douglas Swanson Swanson Real Property, Inc

  

  13000 Los Amigos Rd, Healdsburg, CA 95448
• 

  Est $485,290

  Not Listed For Sale

  219 Powell Ave, Healdsburg, CA 95448

  • Studio
  • 800 Sq Ft

  

  219 Powell Ave, Healdsburg, CA 95448

  Last Sold Summary

  • 8 Days On Market

  Last Listing Agent Richard Cooper Giovannoni & Cooper Realty
• 

  

  /20

  $7,900,000

  Pre-Foreclosure

  • 6 Beds
  • 3 Baths
  • 1,614 Sq Ft

  5285 Westside Rd, Healdsburg, CA 95448

  Located on Westside Rd., one of Sonoma County's premier wine country roads, this 350+ ac. legacy ranch is less than 15 min. from downtown Healdsburg. In the same family since 1958, Bucher Farms is developed with 35 ac. of premium Pinot Noir and Chardonnay wine grapes which have earned consistently high scores in the wine press for some of Sonoma County's most prestigious wineries including

  Darryl Vice Vice Properties

  5285 Westside Rd, Healdsburg, CA 95448
• 

  

  /26

  $12,800 Per Month

  • 4 Beds
  • 3 Baths
  • House for Rent

  14950 Chalk Hill Rd, Healdsburg, CA 95448

  Single Story 4BR/3BA Single Family Home* $12,800/month annual lease* Furnished* 6 acres of land* Swimming pool* Deck* Pizza oven* Hot tub* Fireplace* Laundry room* Air conditioning* Parking* Garden* Pickle Ball court* Badminton court* Bocce ball court* Horse corral* Creek* Short term lease available, 30 days minimum*

  14950 Chalk Hill Rd, Healdsburg, CA 95448
• 

  $199,000

  Sold Mar 24, 2026

  8109 B St, Windsor, CA 95492

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1990

  Last Sold Summary

  • $173/SF
  • 47 Days On Market

  Last Listing Agent Kathleen Munoz eXp Realty of California, Inc

  

  8109 B St, Windsor, CA 95492
• 

  Est $1,740,395

  Not Listed For Sale

  8909 Mill Creek Rd, Healdsburg, CA 95448

  • 2 Beds
  • 2 Baths
  • 1,153 Sq Ft
  • Built 2016

  

  8909 Mill Creek Rd, Healdsburg, CA 95448

  Last Sold Summary

  • 35 Days On Market

  Last Listing Agent Caroline Johnson The Agency
• 

  

  /23

  $2,900,000

  • Land
  • 1,020 Acres
  • $2,843 per Acre

  9007 Stewarts Point-Skaggs Springs Rd, Healdsburg, CA 95448

  The Waltenspiel Ranch offers 1019+/- acre haven just 30 minutes from downtown Healdsburg. This generational ranch is a nature lover's paradise, nestled among rolling hills and majestic oak trees, offering breathtaking views at every turn. Miles of well-maintained trails wind through the property, perfect for hiking, biking, and horseback riding. Water is abundant, with numerous natural springs

  Darryl Vice Vice Properties

  9007 Stewarts Point-Skaggs Springs Rd, Healdsburg, CA 95448
• 

  

  /18

  $20,000 Per Month

  • 3 Beds
  • 2.5 Baths
  • 2,170 Sq Ft
  • House for Rent

  212 Tucker St, Healdsburg, CA 95448

  Contemporary townhouse located two blocks from the Town Plaza. AIA Award winning design by renowned architect Stanley Saitowitz, completed in fall 2021, and recently published. Large private courtyard with pool. Exquisite finishes. Top of the line appliances. Ready to move in.

  Georgina McInerney Compass

  212 Tucker St, Healdsburg, CA 95448
• 

  $975,950

  Sold Nov 24, 2025

  225 Mountain View Dr, Healdsburg, CA 95448

  • 2 Beds
  • 2 Baths
  • 1,284 Sq Ft
  • Built 1974

  Last Sold Summary

  • $760/SF
  • 37 Days On Market

  Current Estimated Value $948,004

  Last Listing Agent Andrew Meyer Singletrack Real Estate

  

  225 Mountain View Dr, Healdsburg, CA 95448
• 

  Est $1,557,187

  Not Listed For Sale

  2859 Wallace Creek Rd, Healdsburg, CA 95448

  • 2 Beds
  • 2 Baths
  • 1,700 Sq Ft
  • Built 1947

  

  2859 Wallace Creek Rd, Healdsburg, CA 95448

  Last Sold Summary

  • 48 Days On Market

  Last Listing Agent Grace Lucero Vanguard Properties

Showing Results 1 - 40, Page 1 of 18