Healdsburg, CA Homes for Sale with Pool

Originally built in 1890 and reimagined beginning in 2021, this Healdsburg home blends historic character with modern luxury. Vintage Douglas fir floors, some reclaimed from a Seattle silo, set the tone for artisan craftsmanship throughout. The kitchen features custom cabinetry, a vintage ILVE stove from Italy, Fisher & Paykel dual-drawer refrigeration, and a large marble island. Comfort details

Kellie Larson Luxe Places International

Stunning single-story home on an incredible lot with privacy and views in downtown Healdsburg. Renovated in 2025, this high-end Mid-Century style home has designer touches, boasts 4 generous bedrooms, plenty of space for gathering and entertaining, a fabulous pool and sits on a .45-acre parcel. Tucked back off University, the sun filled flag lot has mature landscaping and views to Fitch Mountain

Elisea Albertson Vanguard Properties

New co-ownership opportunity by Pacaso: Own one-eighth of Olive Grove, a professionally managed, turnkey home. Tucked into the rolling hills of Healdsburg, this private retreat offers the ultimate wine country escape. Set on over three acres with heritage olive trees and a private orchard, this design-forward estate is just minutes from Sonoma's world-renowned wineries. A winding drive leads to

Maxx Rifkin Pacaso Inc

Residence A102 boasts exquisite Italian-made MandiCasa cabinetry, premium Miele appliances, temperature-controlled wine storage, Waterworks fixtures, natural stone countertops, and wide-plank hardwood flooring. The home features an impressive 18-foot vaulted ceiling and expansive floor-to-ceiling windows. Sliding glass walls open to reveal a generous 645 sq. ft. terrace, complete with a fully

Garrett Frakes Polaris Pacific

Experience the pinnacle of wine country living at this exceptional Dry Creek Valley estate, set on 25.9 private acres surrounded by world-class vineyards. This stunning home offers 4 bedrooms, one a newly added in-law unit, 4 full baths, and 2 powder rooms, masterfully blending modern sophistication with natural beauty. Expansive terraces, manicured grounds, and panoramic vineyard views create a

Emily Martin Healdsburg Sotheby's Int'l Rea

Welcome to 4395 Pine Flat Rd, an elegant Healdsburg estate offering some of the most breathtaking views in Sonoma County. Just minutes from downtown yet worlds away, this extraordinary property blends luxury, comfort, and resort-style amenities on 10+ mostly usable acres. The Main Residence consists of a four-bedroom, five-bathroom home is designed for both entertaining and everyday living. High

Elisea Albertson Vanguard Properties

Introducing The Grove, an exclusive enclave of 23 luxury townhomes in the heart of Healdsburg, just one block from the Foley Family Community Pavilion and three blocks from the iconic Healdsburg Plaza. This thoughtfully redesigned residence blends contemporary sophistication with exceptional craftsmanship across 1,507 square feet, offering a spacious primary suite and a versatile upper-level loft

Jonathan Bruington W Real Estate

Experience the pinnacle of Healdsburg living in this newly constructed top-floor penthouse, where world-class architecture meets the serene beauty of the preserve. Designed by the visionary firm Olson Kundig, recently honored in the 2025 AD100, this residence defines modern sophistication within the exclusive Mill District enclave. The expansive single-floor layout is anchored by a true chef's

Garrett Frakes Polaris Pacific

Tucked just minutes from the heart of downtown Healdsburg, this striking newer home offers a rare blend of modern design & privacy with a wine country lifestyle ease. Set amid meadow views, gardens, and forested hills, the property delivers true single-level living with seamless indoor-outdoor flow-perfect for everyday comfort and effortless entertaining. Glass-walled Nano doors open the

Jeffrey Schween Compass

5100 West Soda Rock offers a rare opportunity to shape a Wine Country retreat in a coveted Alexander Valley setting. Down a quiet country road and set on approximately five acres, the property enjoys broad, calming views from its bench-land position, with the top of the knoll showcasing some of the most striking vistas on the site. The land's gentle elevation and open layout create multiple

Erin Lail Coldwell Banker BofV ST Helena

Located in Healdsburg's premier Mill District neighborhood, this impeccably designed studio in the Canopy collection offers an exceptional blend of style, function, and convenience just steps from the historic town plaza. Nestled among a preserved grove of redwoods and adjacent to a community park, this luxury residence is part of a one-of-a-kind development by world-renowned architects Olson

Jess Young Golden Thread Real Estate

Perched on a private ridge above Healdsburg, on nearly an acre overlooking town, the setting delivers sweeping panoramic views and a level of privacy that feels worlds away, yet the Plaza, Russian River, and Healdsburg's celebrated dining scene are just minutes below. Originally built in 1948 and extensively remodeled, the single-level residence blends mid-century character with refined

Kellie Larson Luxe Places International

Price Reduction! Best value of a remodeled home within walking distance to downtown, Welcome to the Grove Lofts, a collection of 23 luxurious townhomes conveniently located within walking distance of the charming downtown Healdsburg. This neighborhood is renowned for its exceptional restaurants and tasting rooms, promising an unforgettable culinary experience. If you're seeking a low-maintenance,

Hans Amador Luxe Places International

Residence B201 at Canopy at Mill District offers a serene sanctuary designed by world-renowned AD100 architect Olson Kundig. This brand-new, one-bedroom plus den is perfectly perched on the second floor, looking into beautiful redwood trees and overlooking the tranquil preserve. The open floor plan features a gourmet kitchen that flows seamlessly into the living and dining areas, all with balcony

Garrett Frakes Polaris Pacific

Welcome to Wine Country living in the highly sought-after Fitch Mountain Villas. This charming 3-bedroom, 2.5-bathroom corner-lot home offers 1,692 square feet of beautifully updated living space. The well-designed floor plan is perfect for both entertaining and everyday living, featuring a spacious main room centered around a cozy gas log fireplace and glass slider to the fully fenced yard. Move

David Hunt Sonoma Realty Group

Sited upon a naturally protected contour on 113 acres in one of Northern California's most desirable wine country settings, The Clearview Estate is a luxury vineyard estate near Healdsburg in Sonoma County, offering remarkable privacy, unobstructed sweeping views, and refined living in the heart of wine country. Just minutes from the Michelin-starred dining of Healdsburg, renowned wineries, and

Kevin McDonald Sotheby's International Realty

165 Sycamore Court is a newly completed 5-bedroom, 6.5-bathroom custom estate at Montage Residences Healdsburg, set on a private court with panoramic Dry Creek Valley views. Designed by BAR Architects, this 7,899 total sq / ft home offers seamless indoor-outdoor living with dual primary suites, a vaulted great room, media room, display wine storage, and expansive terraces featuring an

Seth Cotter Ohana Realty Corp.

Welcome to beautiful Alexander Valley! This sprawling single-level mid-century modern home sits on a flat 3 acres, ideally situated among vineyards with incredible 360-degree views. A Wine Country entertainer's dream! Enjoy warm Sonoma County days, lounging by the pool, and preparing a feast in your outdoor kitchen. A 300+ year old heritage oak tree sits at the north end of the property, creating

Ann Amtower Compass