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5-Bedroom Homes for Sale in 95448

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  • /45

    $2,695,000 Open Sat 12PM - 2PM

    • 5 Beds
    • 5.5 Baths
    • 3,252 Sq Ft

    1003 Sunnyside Dr, Healdsburg, CA 95448

    Modern Luxury Meets Timeless Design in This Exceptional Estate. This stunning single-story home blends sleek sophistication with everyday comfort. Featuring 3 spacious bedrooms, a dedicated office, and a thoughtfully designed great room, the home is adorned with Restoration Hardware finishes and wide-plank oak floors throughout. The formal dining room offers a refined space for entertaining,

    Kellie Larson Luxe Places International

    1003 Sunnyside Dr, Healdsburg, CA 95448
  • /35

    $745,000

    • 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. Nestled on 3.3 acres in Sonoma's wine country, this 5-bedroom, 5-bath home embraces sustainable architecture. The idyllic setting is just 10 minutes from charming Healdsburg. The H-shaped, single-level floor plan is anchored by a great room positioned under a distinctive butterfly-shaped roof. The

    Joseph Maehler Pacaso Inc

    2252 W Dry Creek Rd, Healdsburg, CA 95448
  • /20

    $7,900,000

    • 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
  • /51

    $4,950,000

    • 7 Beds
    • 5 Baths
    • 4,151 Sq Ft

    7011 Dry Creek Rd, Healdsburg, CA 95448

    Discover the epitome of country living on 29+/- acres nestled in the esteemed Dry Creek Valley. This unique property features two turn of the century farmhouse homes, each offering its own charm and functionality, plus a 900 +/- sq ft unit built in 1998, making it an exceptional opportunity for multi-generational living, investors or those seeking to build their own wine country estate. Built in

    Monica Bugica Compass

    7011 Dry Creek Rd, Healdsburg, CA 95448
  • /96

    $6,950,000

    • 6 Beds
    • 5 Baths
    • 5,132 Sq Ft

    9110 Chalk Hill Rd, Healdsburg, CA 95448

    Don't miss this splendid property! A gated entry crosses a private bridge over a rocky creek bed. Just around the corner is an enchanted pond enhanced by boat and swimming docks. The pond is bordered by mature trees and augmented by a fenced garden with fruit trees. A newer RV unit sits near the lake so that camp outs, swimming, barbeques and volley ball, and rests can be thoroughly enjoyed. Wind

    Richard Frank Sterling California Properties

    9110 Chalk Hill Rd, Healdsburg, CA 95448
  • /67

    $4,500,000

    • 5 Beds
    • 6 Baths
    • 6,340 Sq Ft

    13404 Flora Ranch Rd, Healdsburg, CA 95448

    Flora Ranch Estate sits on 40+ acres atop a vineyard knoll with a beautiful custom-built Mediterranean inspired home overlooking Alexander Valley and Mt Saint Helena with panoramic views. Inside the home, warm, inviting spaces feature soaring beam-wrapped cathedral ceilings, an open-concept layout, and serene seating areas throughout to relax amongst the views. Step onto the wrap-around back deck

    David Hunt Sonoma Realty Group

    13404 Flora Ranch Rd, Healdsburg, CA 95448
  • /71

    $3,650,000

    • 6 Beds
    • 4 Baths
    • 3,400 Sq Ft

    12076 Cloud Ridge Rd, Healdsburg, CA 95448

    Situated amidst the redwoods in Healdsburg's scenic Mill Creek, this nearly 43-acre property blends peace, privacy, and timeless design. Accessed by a private road, the main home is a 4BD/3BA Craftsman built from first-growth redwood, with one bed and bath conveniently located on the main level. A spacious paver patio wraps the home, offering the perfect spot to soak in the views. Inside, the

    Morgan- Sullivan Group Re eXp Realty of California Inc

    12076 Cloud Ridge Rd, Healdsburg, CA 95448
  • /99

    $5,995,000

    • 5 Beds
    • 4 Baths
    • 4,000 Sq Ft

    681 S Fitch Mountain Rd, Healdsburg, CA 95448

    Just blocks away from the Healdsburg Plaza, this property is a rare gem. Fully restored in 2024, this legacy property was once owned by Coronel Roderick Matheson's family (for whom the broad, cherry tree-lined street in Healdsburg is named after in the 1900's). In 2024, the home & grounds underwent a complete structural & interior restoration, elevating it to current luxury & custom construction

    Tatiana Mcwilliams Live Wine Country

    681 S Fitch Mountain Rd, Healdsburg, CA 95448
  • /33

    $5,995,000

    • 5 Beds
    • 4.5 Baths
    • 5,629 Sq Ft

    991 Grove St, Healdsburg, CA 95448

    Exquisite 4 bedroom residence with separate 1 bedroom/1 bath ADU situated on approx .3 acres. Recently completed in 2021, this home is an oasis close to the Healdsburg Plaza. The main residence features soaring ceilings, a dramatic centerpiece fireplace, architectural suspended staircase, walls of windows, a sleek modern kitchen with grey tone cabinetry and Miele appliances. The floor plan is

    Sheryl Morgensen Sotheby's International Realty

    991 Grove St, Healdsburg, CA 95448
  • /28

    $3,850,000

    • 21 Beds
    • 13 Baths
    • 13,462 Sq Ft

    103 Bailhache Ave, Healdsburg, CA 95448

    Prime Development Opportunity in Healdsburg! Be part of Healdsburg's future while honoring its past with this rare development opportunity in Sonoma County's renowned wine country. Available for the first time in 50 years, this local family whose blue-collar legacy helped shape Healdsburg, spans over 3.17 acres across three contiguous APNs. Ideally positioned at the beginning of Bailhache Avenue

    Niccolo Pigni Engel & Völkers

    103 Bailhache Ave, Healdsburg, CA 95448
  • /19

    $910,000

    • 5 Beds
    • 2 Baths
    • 1,620 Sq Ft

    105 Bailhache Ave, Healdsburg, CA 95448

    Available for the first time in over 50 years, 105 & 105A Bailhache Ave presents a rare opportunity just outside Healdsburg city limits. Set on a flat 0.36-acre parcel, this property features two detached single-story homes: a 2BD/1BA in front and a 3BD/1BA in back each offering charm, privacy, and potential. Whether you choose to renovate, rent, live multigenerational, or redevelop, the rural

    Niccolo Pigni Engel & Völkers

    105 Bailhache Ave, Healdsburg, CA 95448
  • /18

    $950,000

    • 8 Beds
    • 5 Baths
    • 3,930 Sq Ft

    107 Bailhache Ave, Healdsburg, CA 95448

    Offered for the first time in 50 years, this rare multi-cottage property sits on a flat, sunny parcel just minutes from downtown Healdsburg. Steeped in local history, 107 Bailhache Ave includes five detached single-story homes totaling approximately 3,900 sq ft of combined living space. The mix features three 2BD/1BA cottages and two 1BD/1BA units, each with private entrances and outdoor areas.

    Niccolo Pigni Engel & Völkers

    107 Bailhache Ave, Healdsburg, CA 95448
  • /27

    $1,990,000

    • 6 Beds
    • 4 Baths
    • 4,000 Sq Ft

    103 Bailhache Ave, Healdsburg, CA 95448

    Offered for the first time in over 50 years, 103 Bailhache Ave is a rare dual-zoned property (heavy industrial + residential) at the entrance to Healdsburg. Set on a parcel ripe with potential, this 4,000+/- sq ft opportunity includes four 1,000+/- sq ft commercial shop spaces ideal for artisans, tradespeople, or boutique production, plus a 2,600+/- sq ft residence divided into two spacious

    Niccolo Pigni Engel & Völkers

    103 Bailhache Ave, Healdsburg, CA 95448
  • /47

    $750,000

    • 5 Beds
    • 3 Baths
    • 2,592 Sq Ft

    15900 Healdsburg Ave, Healdsburg, CA 95448

    Unlock the potential of this spacious 5-bedroom, 3-bathroom home set on a generous 0.8614-acre lot at the base of a hillside. Located in desirable North Healdsburg, this property offers a rare blend of privacy, space, and city services an ideal canvas for your vision. The mostly flat, usable yard provides endless opportunities for gardening, outdoor entertaining, or more. Inside, the home is

    Brook Terhune Corcoran Icon Properties

    15900 Healdsburg Ave, Healdsburg, CA 95448
  • /99

    $44,000,000

    • 11 Beds
    • 9.5 Baths
    • 9,000 Sq Ft

    13414 Chalk Hill Rd, Healdsburg, CA 95448

    Harvest the opportunity to own the most premier Chalk Hill winery and estate available for sale in Sonoma County, Medlock Ames, located at beautiful Bell Mountain in Healdsburg with an additional Alexander Valley tasting room. This sprawling vineyard estate sits majestically on 342 acres of which 47 are prime Russian River and Alexander Valley appellation providing the best of the best 92 to 96

    Christine Wilhelm Mayacama Luxury Real Estate

    13414 Chalk Hill Rd, Healdsburg, CA 95448
  • /36

    $2,900,000

    • 5 Beds
    • 4 Baths
    • 4,516 Sq Ft

    1194 Felta Rd, Healdsburg, CA 95448

    This peaceful Gentleman's Ranch is nestled in a beautiful natural setting and is a magical palette for a creative lifestyle. The charming 1910 Craftsman residence shows it's original details well. This main home is about 3,075 sf. (3/2)include a full 'daylight' basement. Rustic out buildings include: guest home is 840 sf. (2/1)and studio-loft at approx 600 sf. 30 magical acres of privacy yet only

    Eric Drew Healdsburg Sotheby's Internati

    1194 Felta Rd, Healdsburg, CA 95448
  • /58

    $7,900,000

    • 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 Inc

    5285 Westside Rd, Healdsburg, CA 95448
  • /43

    $4,700,000 New Construction

    • 6 Beds
    • 5 Baths
    • 5,200 Sq Ft

    8353 W Dry Creek Rd, Healdsburg, CA 95448

    Luxury custom home in the countryside with beautiful guest home overlooking the world famous Dry Creek Valley full of wineries and vineyards. This home has a hobby vineyard sprinkled with 100 olive trees and numerous fruit trees. Not so secluded as you can get to downtown Healdsburg in about 15 minutes to enjoy all the 5 star restaurants and music festivals thrown throughout the year. Also close

    Steve Vail Vail and Associates Realtors

    8353 W Dry Creek Rd, Healdsburg, CA 95448
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