Healdsburg, CA Homes for Sale with Pool

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

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

Stunning Dry Creek Valley estate set on 11.91 acres with sweeping views of Mount St. Helena and the Dry Creek ridgeline. This 1,920 SF Mediterranean-style residence is thoughtfully designed for relaxed Wine Country living and effortless entertaining, featuring an open floor plan, vaulted ceilings, and expansive windows that frame the surrounding landscape. Spanish tile floors run throughout the

Caroline Johnson The Agency

Nestled in the heart of Sonoma County's renowned Dry Creek Valley, this exceptional 67-acre ranch offers a rare combination of premier vineyards, a boutique winery open for public tastings and limited events, and complete privacy on sought-after benchland with premium southwestern exposure. Perched atop a scenic knoll, the estate residence 3200 Sq ft +/- commands sweeping panoramic views over the

Jeff Bounsall Coldwell Banker Realty

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

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

Set in the heart of prestigious Dry Creek Valley, just minutes from downtown Healdsburg, 1099 Dry Creek Road is a newly built modern estate that redefines wine country luxury. Designed for seamless indoor-outdoor living, this private 1.6 acre retreat is surrounded by vineyard and mountain views, offering both tranquility and convenience. The main residence spans approximately 3,753 sq ft with 3

Grace Lucero Vanguard Properties

Premier Alexander Valley estate with Stunning Views nestled along a peaceful, paved country lane, this exceptional ranch estate offers breathtaking panoramic views of Mt. St. Helena, the Russian River Valley, the Mayacamas Mountains, vineyards and iconic Chalk Hill valley. The property features a spacious 3,006 sq. ft. (+/-) multi-level ranch residence, complemented by a sparkling inground

Jeff Bounsall Coldwell Banker Realty

Set in the heart of Healdsburg's coveted Dry Creek Valley, this 40+/- acre vineyard estate offers a rare blend of natural beauty and understated elegance. The 3,678+/- square-foot main residence is perfectly positioned to capture sweeping, unobstructed views of Geyser Peak and Mount St. Helena, with vineyards, rolling hills, and the valley floor nestled in between. A charming approximately 650

Carole Sauers Golden Gate Sotheby's

Welcome to Healdsburg! A sprawling single-level home set on 1.4 acres in Healdsburg's coveted Vintage Hills neighborhood. Perfectly marrying the charm of country living with the convenience of city services, all tucked away on a peaceful lane that embodies the best of Wine Country living. This property is as practical as it is beautiful, offering exceptional energy efficiency with an owned solar

Ann Amtower Compass

Nestled in Healdsburg on a secluded 6-acre property cherished by one family for over 42 years, this tranquil retreat offers serenity, privacy, and conveniencejust an 8-minute drive from the vibrant Healdsburg Plaza. The home features vaulted ceilings crafted with local clear-heart tongue-and-groove redwood, a cozy fireplace, generous living spaces, 3 bedrooms, 3 full bathrooms, a laundry room,

Mary Curran Compass

Come and enjoy the elegant architecture of this beautiful custom home, set on over 1/2 acre in the heart of Healdsburg's wine country. Upscale amenities include a chef's kitchen with Viking appliances, Brazilian wood floors and solar with 2 battery backups. The open floor plan offers abundant natural light, walk in pantry, spacious laundry and 2 central air and heating systems. The serene grounds

Michael Tremont Dayton & Tremont Real Estate

Enjoy this well maintained and tastefully updated 4 bedroom 3 bath home within close proximity to schools, shopping and restaurants. The interior has been freshly painted, and the open floor plan offers abundant natural light. Relax and entertain by the pool in the low maintenance and peaceful back yard. Plenty of storage throughout the home and in the oversized two car garage.

Michael Tremont Dayton & Tremont Real Estate

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

Ride your bikes to town from your front door! Welcome to your private Sonoma Wine Country retreat, just five minutes from Healdsburg Plaza. Set on a gated 2.68-acre parcel, this single-level residence offers exceptional privacy and sweeping vineyard views across the Russian River Valley. Designed for effortless indoor-outdoor living, the home is encircled by a newly constructed 2,000-square-foot

Ann Amtower Compass

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

At the end of a quiet cul-de-sac in the coveted Fitch Mountain Villas, a sense of calm begins before you even step inside. Surrounded by thoughtfully curated, zen-like gardens, the home unfolds as a private retreat where indoor and outdoor living feel naturally connected. Light fills the interior, drawing you toward a custom-designed kitchen with stainless steel appliances and abundant storage,

Jess Young Golden Thread Real Estate

Set in the heart of Alexander Valley in Healdsburg, this gated 44-acre estate offers breathtaking views of Mount St.Helena, surrounded by rolling vineyards and hills. This fully off-grid, sustainable, carbon-neutral home was designed by an award-winning architect. The estate is pure luxury and blends warm modern design with floor-to-ceiling windows that connect indoor and outdoor living. The main

Krystal Rubiogomez Compass

In-Town Healdsburg Farmhouse Estate on 2.16 Acres: Set on a rare 2.16-acre parcel in downtown Healdsburg, this exceptional property offers remarkable flexibility - whether envisioned as a private family compound, future development opportunity, or a turnkey wine country retreat. The thoughtfully designed single-level farmhouse spans approximately 3,326 square feet and features three generously

Grace Lucero Vanguard Properties

Premier southern Alexander Valley estate, winery, vineyards, cattle ranch along the Russian River in Sonoma County's renowned southern Alexander Valley AVA comprises approximately 320 acres across three parcels, offering an exceptional turn-key wine country property that combines a fully operational 25,000-case winery, productive vineyards, and expansive ranch potential with stunning panoramic

Jeff Bounsall Coldwell Banker Realty

Flora Ranch Estate sits on 40+ acres atop a gentle vineyard knoll with a beautiful custom-built Mediterranean inspired home overlooking Alexander Valley, Mt Saint Helena and Chalk Hill with breathtaking 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.

David Hunt Sonoma Realty Group

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

Just over a mile from the historic Healdsburg Plaza, 620 Dry Creek Road is a rare compound at the entrance to one of Sonoma County's most celebrated wine valleys. Set on 1.27 level, peaceful acres bordered by redwood trees and open pasture, the property brings together four distinct structures: a 3-bedroom, 2-bath main house with a loft, skylights, two fireplaces, and southern views of vineyards

Grace Lucero Vanguard Properties

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

Perfect wine country retreat completely lock and go, 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, turnkey home, look no further.

Hans Amador Luxe Places International

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

Nestled on one of Healdsburg's most coveted streets, just a short stroll from the vibrant Plaza, 438 Matheson St. is a stunning example of early 20th-century charm paired with modern-day versatility. Set on a generous corner lot spanning approximately a quarter acre, this property boasts a serene oasis with formal gardens, a sparkling pool, and room to expand with additional flower or vegetable

Alain-Martin Pierret Compass

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

Seth Cotter Ohana Realty Corp.

Rarely does a home of such architectural intention arrive on the market. Conceived by BAR Architects & Interiors a celebrated San Francisco firm whose work runs through the fabric of California's finest resort communities this 5,642 square foot site-responsive residence is expressed with an unmistakable fluency in luxury living. The design is organized under a signature butterfly roof, a floating

Curtis Tischler Sagepoint Real Estate Company

Welcome to beautiful Alexander Valley! This sprawling single-level mid-century modern home is located 13 short minutes from the Healdsburg Plaza. Drive through your private gate to a flat 3-acre lot, ideally situated among vineyards with incredible 360-degree views. A Wine Country entertainer's dream! Enjoy warm Sonoma County days, lounging by the saltwater pool, and preparing a feast in your

Ann Amtower Compass

Set on approximately 15 acres in Sonoma County, this newly constructed property offers a rare combination of modern design, usable land, and a versatile multi-residence layout. Thoughtfully planned and designed for both everyday living and entertaining, the property provides a seamless blend of indoor comfort and outdoor lifestyle. The main residence features clean architectural lines, an

Kellie Larson Luxe Places International

Ten minutes from the Healdsburg plaza, at the quiet end of Eastside Road, fruit trees scent the air and the energy shifts the moment you turn onto the property. 10936 Eastside Road sits on 3.25 private acres at the end of a dead-end lane a single-level, approximately 1,840-square-foot home with 3 bedrooms plus a bonus room, 3 bathrooms, and a rare blend of privacy, wine-country setting, and

David Hargreaves W Real Estate

979 Lupine Court represents Healdsburg living at its finest. An entertaining oasis, this 4 bedroom, 3 bathroom, fully detached 2,346 sq ft home with spacious bedrooms and bright, airy layout, surrounding the lavish pool area beckons those who want to share in the wine country lifestyle. Entry level features 1 bedroom, 1 full bathroom, large open-plan kitchen with adjoining family room w/ gas

Patrick Shannon Trinity Realty, Inc

Experience the pinnacle of Healdsburg living in this newly constructed, full-floor penthouse where world-class architecture meets the serene beauty of the preserve. Accessible via a private elevator entrance, this residence was designed by the visionary firm Olson Kundig, recently honored in the 2025 AD100, defining modern sophistication within the exclusive Mill District enclave. The expansive

Garrett Frakes Polaris Pacific