Vintage homes for sale & real estate in Healdsburg, CA

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ABOUT THIS HOME
Vintage Home for sale in Healdsburg, CA:
Healdsburg-an exquisite 1938c home effortlessly blending vintage charm w modern elegance. Nestled in a premier locale. this meticulously remodeled residence offers 2,681 +/-sqft of refined living space. Step inside to discover an inviting open-concept layout, ideal for both intimate gatherings or grand entertaining. The main residence boasts 3 spacious ensuite-bedrooms + office + 3.5 beautifully appointed bathrooms. Thoughtful design touches harmonize period details w contemporary conveniences, showcasing high-end finishes & designer elements throughout. The heart of the home features expansive living areas bathed in natural light, seamlessly connecting to a chef's kitchen w contempor

$3,965,000

4 beds4.5 baths3,507 sq ft

319 1st St, Healdsburg, CA 95448

Custom cabinetry • High-end finishes • Chef's kitchen

ABOUT THIS HOME
Vintage Home for sale in Healdsburg, CA:
Discover this cozy, single-level home in Healdsburg! Featuring 2 bedrooms and 1 bath, this home offers hardwood floors and a two car garage. Nestled on a 7,500 sq ft lot, it's perfect for easy living. Don't miss it

$900,000

2 beds1 bath970 sq ft

818 Josephine Ln, Healdsburg, CA 95448

Two car garage • Hardwood floors • 7,501 sq ft lot

ABOUT THIS HOME
Vintage Home for sale in Healdsburg, CA:
Exceptional Potential on Coveted Brown Street. Steeped in warmth and family legacy, this 3-bedroom, 2-bath home has been cherished by the same family for four generations. Originally built for their great-nonna and later enjoyed as a family retreat, it became a welcoming gathering place for friends, food, and celebration. The small kitchen in the basement once supported generous meals for the family's legendary parties a nod to their bakery roots in San Francisco. Located on coveted Brown Street, this property offers exceptional value in one of Healdsburg's most desirable areas. Enjoy close proximity to the town's vibrant culinary scene with award-winning restaurants, tasting rooms, and wo

$869,000

3 beds2 baths1,389 sq ft

820 Brown St, Healdsburg, CA 95448

Spacious yard • Wood-burning stove • Outdoor dining space

ABOUT THIS HOME
Vintage Home for sale in Healdsburg, CA:
Vintage Charm Meets Modern Style in Downtown Healdsburg - Timeless charm meets modern comfort in this beautifully updated 1880 farmhouse, located on one of Healdsburg's most iconic and sought-after streets. Just blocks from the Plaza, Giorgi and Badger parks, the river, and the golf course, this home offers the perfect blend of convenience and Wine Country lifestyle. Set on a thoughtfully designed 4,356 sq. ft. lot, the property maximizes every outdoor space with inviting front, back, and side yards surrounded by lush landscaping and privacy. Inside, natural light fills the 1,288 sq. ft. interior, showcasing 9' ceilings, engineered hardwood floors, and stylish designer lighting. The home fe

$1,497,000

2 beds1.5 baths1,288 sq ft

532 Matheson St, Healdsburg, CA 95448

Modern style • Inviting front yard • Vintage charm

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ABOUT THIS HOME
Vintage Home for sale in Healdsburg, CA:
Charming 1920s Home with Modern Upgrades on 3.2 Acres. Experience timeless elegance in this beautifully updated 1920s home, set behind a private iron gate on approx. 3.2 acres. The chef's kitchen features a large island, double ovens, and wine fridgeideal for entertaining. Enjoy cozy living spaces with a rustic fireplace, built-ins, and a Murphy bed in the den. The spacious primary suite offers garden views and a walk-in closet. Modern comforts include updated windows and owned solar. A detached studio with its own porch is perfect for a home office or creative space. Outside, relax in the landscaped English garden with a peaceful fountain. Additional outbuildings add to the property's char

$1,659,000

2 beds2 baths1,535 sq ft

2267 Westside Rd, Healdsburg, CA 95448

Rustic fireplace • Large walk-in closet • Built-in bookshelves

Property at 620 Brown St, Healdsburg, CA 95448, 4 beds, 4.5 baths

$3,750,000

4 beds4.5 baths2,800 sq ft

620 Brown St, Healdsburg, CA 95448

Property at 1561 S Fitch Mountain Rd, Healdsburg, CA 95448, 1 bed, 1 bath

$425,000

1 bed1 bath636 sq ft

1561 S Fitch Mountain Rd, Healdsburg, CA 95448

Property at 995 Dry Creek Rd, Healdsburg, CA 95448, 3 beds, 3 baths

$1,970,000

3 beds3 baths3,360 sq ft

995 Dry Creek Rd, Healdsburg, CA 95448

Property at 635 Brown St, Healdsburg, CA 95448, 3 beds, 3.5 baths

$1,450,000

3 beds3.5 baths1,839 sq ft

635 Brown St, Healdsburg, CA 95448

Property at 1311 W Dry Creek Rd, Healdsburg, CA 95448, 2 beds, 1.5 baths

$2,395,000

2 beds1.5 baths1,710 sq ft

1311 W Dry Creek Rd, Healdsburg, CA 95448

Property at 528 Sanns Ln, Healdsburg, CA 95448, 4 beds, 2 baths

$1,299,999

4 beds2 baths2,080 sq ft

528 Sanns Ln, Healdsburg, CA 95448

Property at 1558 Magnolia Dr, Healdsburg, CA 95448, 3 beds, 2.5 baths

$3,995,000

3 beds2.5 baths7,208 sq ft

1558 Magnolia Dr, Healdsburg, CA 95448

Property at 1241 Grove St, Healdsburg, CA 95448

$950,000

0 beds— baths1,700 sq ft

1241 Grove St, Healdsburg, CA 95448

Property at 5285 Westside Rd, Healdsburg, CA 95448, 6 beds, 3 baths

$7,900,000

6 beds3 baths1,614 sq ft

5285 Westside Rd, Healdsburg, CA 95448

Property at 555 - 557 Powell Ave, Healdsburg, CA 95448, 2 beds, 2 baths

$2,965,000

2 beds2 baths1,100 sq ft

555 - 557 Powell Ave, Healdsburg, CA 95448

Property at 9440 Mill Creek Rd, Healdsburg, CA 95448

$679,000

— beds— baths— sq ft

9440 Mill Creek Rd, Healdsburg, CA 95448

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ABOUT THIS HOME
Vintage Home for sale in Healdsburg, CA:
The property consists of three structures: two retail buildings and a single-family residence. The retail spaces are leased to an artist and a gift shop that is licensed to sell beer and wine. The residence is a three-story structure. The ground level contains is a garage that used as a workshop. The second level includes a single room currently used as a laundry area, with potential use as a third bedroom or office. This level also features a large patio with exterior stairs leading to the upper floor. The top level is an updated two-bedroom one-bath flat with attractive views, a functional layout, and a wood-burning fireplace. The grounds between the retail buildings and the residence inc

$1,100,000

2 beds1 bath3,915 sq ft

12060 Hwy 116 Hwy, Guerneville, CA 95446

Exterior stairs • Laundry area • Large patio

ABOUT THIS HOME
Vintage Home for sale in Healdsburg, CA:
Discover this Residential Development Opportunity on the edge of Northeast Santa Rosa / Windsor border. Unlock the potential of this 2.2+/- ac lot surrounded by developed neighborhood communities. Featuring two existing structures and multiple outbuildings, this property has potential for many opportunities. Public sewer, well, electricity, gas, cable and internet available to site. Don't miss this opportunity!

$1,100,000

4 beds3 baths2,204 sq ft

6283 - 6285 Old Redwood Hwy, Santa Rosa, CA 95403

2.2 ac lot • Public sewer • Electricity

ABOUT THIS HOME
Vintage Home for sale in Healdsburg, CA:
Life in the country, relaxation amongst the Redwoods, in cozy Cazadero! Gated home with long, elegant driveway, known as The Ohana House. Four short miles, eight minutes to highway 116. Cozy cabin with two comfy bedrooms, one bath, across from Austin Creek. Remodeled kitchen. Ample living room-kitchen with some upgrades. The front yard is your very own wonderland with full foliage. Driveway is perfect for parking multiple vehicles! Spacious deck for relaxing and entertainment. This home is great for primary residence or weekend wine country retreat. The location is a short drive to the spectacular Sonoma coast, 400+ Sonoma County wineries, Russian River, beaches, golf, and great local resta

$374,999

2 beds1 bath999 sq ft

4290 Cazadero Hwy, Cazadero, CA 95421

Ample living room • Gated home • Remodeled kitchen

ABOUT THIS HOME
Vintage Home for sale in Healdsburg, CA:
Nestled in the heart of the world renowned Alexander Valley AVA, this beautiful approximately 89.7 acre property offers exceptional potential in a premier wine growing region. Approximately 71 acres are currently fallow, providing a blank canvas for future vineyard development or agricultural use. The property is enrolled in the Williamson Act and consists of one legal description encompassing three APNs and three physical addresses. A reservoir and a high producing well support the property's agricultural capabilities, and an active VESCO permit granted in fall 2023 provides a valuable head start for future planting. Existing improvements include a 2 bedroom home and barns, offering opport

$3,500,000

2 beds1 bath1,300 sq ft

6114 Red Winery Rd, Geyserville, CA 95441

2 bedroom home • Barns • 71 acres fallow

ABOUT THIS HOME
Vintage Home for sale in Healdsburg, CA:
Explore the potential of 17390 Riverside Drive, Guerneville, CA a unique opportunity for your dream lifestyle or vacation retreat. This 768 square foot home on a 3,000 sq ft lot has experienced years of deferred maintenance, offering a perfect renovation canvas. With two bedrooms on the upper level, it's ready for personalization. Owned by the same family for generations, this home awaits new owners to transform it into a peaceful getaway or cozy residence. Enjoy a tranquil Russian River setting in close proximity to the water. The gated drive and unfinished sub area adds to its potential. Seize your chance to create a personalized oasis.

$295,000

2 beds1 bath768 sq ft

17390 Riverside Dr, Guerneville, CA 95446

Gated drive • 3,001 sq ft lot • Parking

ABOUT THIS HOME
Vintage Home for sale in Healdsburg, CA:
2 Beds | 2 Baths | Den | Laundry Room | Near the Russian River | Fully Renovated Home Turnkey Monte Rio Retreat – Ideal for Homeowners, Investors, and Short-Term Rental Buyers Beautifully renovated home located steps from the Russian River and surrounded by peaceful redwoods. This property is move-in ready, income-producing, and perfect as a primary residence, vacation home, or short term rental. Property Features & Upgrades Fully Renovated / Move-In Ready New hardwood flooring, remodeled kitchen, updated tiled bathrooms, modern fixtures, new lighting, and fresh interior paint. Updated Kitchen Premium appliances, upgraded countertops, stylish cabinetry — perfect for hostin

$589,000

2 beds2 baths1,221 sq ft

21401 Santa Clara Ave, Monte Rio, CA 95462

Fully renovated • Updated kitchen • Bonus den

Property at 14707 Willow Rd, Rio Nido, CA 95471, 2 beds, 2 baths

$525,000

2 beds2 baths960 sq ft

14707 Willow Rd, Rio Nido, CA 95471

Property at 20340 Highway 116, Monte Rio, CA 95642, 2 beds, 1 bath

$129,000

2 beds1 bath1,083 sq ft

20340 Highway 116, Monte Rio, CA 95642

Property at 14619 Eagle Nest Ln, Guerneville, CA 95446, 3 beds, 2 baths

$650,000

3 beds2 baths1,334 sq ft

14619 Eagle Nest Ln, Guerneville, CA 95446

Property at 14652 Canyon 1 Rd, Guerneville, CA 95446, 3 beds, 2 baths

$535,000

3 beds2 baths1,340 sq ft

14652 Canyon 1 Rd, Guerneville, CA 95446

Property at 6640 1st St, Forestville, CA 95436, 2 beds, 1 bath

$799,950

2 beds1 bath1,080 sq ft

6640 1st St, Forestville, CA 95436

Property at 15246 Rio Nido Rd, Guerneville, CA 95446, 1 bed, 1 bath

$415,000

1 bed1 bath528 sq ft

15246 Rio Nido Rd, Guerneville, CA 95446

Property at 3150 - 3146 Calistoga Rd, Santa Rosa, CA 95404, 4 beds, 2.5 baths

$1,095,000

4 beds2.5 baths3,104 sq ft

3150 - 3146 Calistoga Rd, Santa Rosa, CA 95404

Property at 2387 Meyers Dr, Santa Rosa, CA 95403, 3 beds, 1 bath

$597,000

3 beds1 bath1,158 sq ft

2387 Meyers Dr, Santa Rosa, CA 95403

Property at 21684 Starrett Hill Dr, Monte Rio, CA 95462, 3 beds, 1 bath

$549,000

3 beds1 bath— sq ft

21684 Starrett Hill Dr, Monte Rio, CA 95462

Property at 4350 Cazadero Hwy, Cazadero, CA 95421, 3 beds, 3 baths

$785,000

3 beds3 baths1,850 sq ft

4350 Cazadero Hwy, Cazadero, CA 95421

Property at 540 S Cloverdale Blvd, Cloverdale, CA 95425, 2 beds, 2 baths

$1,400,000

2 beds2 baths2,720 sq ft

540 S Cloverdale Blvd, Cloverdale, CA 95425

Property at 2437 Lomitas Ave, Santa Rosa, CA 95404, 2 beds, 1 bath

$649,000

2 beds1 bath1,247 sq ft

2437 Lomitas Ave, Santa Rosa, CA 95404

Property at 17410 Park Ave, Guerneville, CA 95446, 4 beds, 3 baths

$775,000

4 beds3 baths2,016 sq ft

17410 Park Ave, Guerneville, CA 95446

Property at 6581 St Helena Rd, Santa Rosa, CA 95404

$199,000

— beds— baths— sq ft

6581 St Helena Rd, Santa Rosa, CA 95404

Vintage Homes for Sale in Healdsburg

There are currently 16 vintage homes for sale in Healdsburg at a median listing price of $1.38M. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Healdsburg stay on the market for 92 days and receive 1 offers. Popular neighborhoods include Simi, South Area, Downtown Healdsburg, Chiquita, and North Area. This map is refreshed with the newest listings in Healdsburg every 15 minutes.

In the past month, 8 homes have been sold in Healdsburg. In addition to houses in Healdsburg, there were also 5 condos, 2 townhouses, and 4 multi-family units for sale in Healdsburg last month. Find your dream home in Healdsburg using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Healdsburg are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Healdsburg. Our Healdsburg real estate stats and trends will give you more information about home buying and selling trends in Healdsburg. If you're looking to sell your home in the Healdsburg area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Healdsburg with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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