Healdsburg, CA Homes for Sale with Private Pool

Perched on a gentle knoll with mountain views, this fully remodeled 5 bed/4 bath home offers the perfect blend of vintage charm and modern style just under a mile from Healdsburg's historic Plaza. Thoughtfully updated throughout, the home features a warm, modern aesthetic with preserved architectural details, a sleek chef's kitchen, and updated bathrooms. The spacious layout offers flexibility

Samantha Marquis Compass

Just minutes from the famed Healdsburg Plaza, this stunning property offers luxury living on 1/3 of an acre. A large, usable yard features a pool with built-in spa, covered indoor/outdoor living, outdoor fireplace, and mature landscaping for privacy. Fully rebuilt in 2018, the home blends high-end modern finishes with timeless design. Enjoy engineered wood flooring, slab stone countertops, custom

Randy Waller W Real Estate

Nestled in the stunning hills of Healdsburg, this exquisite property offers a unique blend of luxury and natural beauty. Spanning 1.5 acres, this estate home features breathtaking valley views and is adorned with 300 syrah and zinfandel vines, perfect for the wine enthusiast. The impressive residence boasts 4 bedrooms and 4 bathrooms, providing ample space for relaxation and entertaining. The

Kellie Larson Luxe Places International

Idyllic country home, on 2.4+/- acres in the heart of Dry Creek Valley, blends rustic charm w/refined elegance. Board & batten siding, vaulted ceilings with exposed trusses, white shiplap walls, and vintage heart pine floors channels quintessential farmhouse inspiration. Expansive folding glass doors opens from the light-filled living area to screened porch framing vineyard & hillside views. The

Sheryl Morgensen Sotheby's International Realty

Escape. Entertain. Establish Roots. A Chalk Hill estate that redefines wine country living. Located in the prestigious Chalk Hill AVA, this extraordinary 268 acre estate offers scale, privacy and a rare opportunity to create a generational legacy in one of Sonoma County's most sought-after settings. With two legal parcels, it presents the flexibility to retain the property as a grand private

Ryan Anderton Sonoma Realty Group

Discover the epitome of luxury and tranquility in this architecturally significant home, offering a resort-style lifestyle. Nestled on a soulful and pristine 1.07-acre lot in Healdsburg's coveted Vintage Hills community, this meticulously manicured property provides a serene retreat where the home's regal design seamlessly blends with its natural surroundings. Effortlessly transition between

Bob Besancon The Agency

Welcome to a rare opportunity in the heart of Healdsburg, just 4 blocks from the vibrant Healdsburg Plaza. This exceptional property offers 2 separate parcels, providing a unique blend of luxury, convenience, and potential. The main residence at 504-506 Fitch is a beautifully remodeled single-level home featuring 3bd/2ba, perfect for both relaxation and entertainment. The 2018 remodel has

Ann Amtower Compass

Now is the time to seize this unique opportunity to live, work, and create your future micro-winery, tasting room, and outdoor event space. With over a million dollars in renovation to the outdoor living space, electrical, and new foundation, this 1.75 acre parcel illuminates with possibilities. Breath life into these two large structures for the ideal posh country home, short term rental, or

Kelley Urbani Engel & Völkers Coastal Mendo

Looking for the perfect project with privacy, views and room for all your country property dreams? Not far from downtown Healdsburg near Dry Creek Valley is this amazing opportunity with a single story home in Madrona Knolls. This is a small community of homes on large parcels just behind The Madrona. Ideal location where you can live in the country and still be just minutes to downtown

Elisea Albertson Vanguard Properties

Charming 3-bedroom, 2-bath home located in the heart of beautiful Healdsburg, CA. This inviting property features a spacious backyard with a poolperfect for relaxing or entertaining guests on warm Sonoma days. The garage has been converted into an additional family room, providing valuable extra living space. Just minutes from top-rated local schools, it's ideally located near shopping,

Ashley McSweeney Keller Williams Realty

This charming 3-bedroom, 2.5-bathroom home spanning 2,208 square feet and situated on nearly half an acre! This property, located on a peaceful dead-end street just a 5-minute drive from downtown Healdsburg, presents a unique chance to own the home of your dreams. Step into your own private backyard retreat, featuring an in-ground pool, spa, and a spacious patio perfect for sunbathing, evening

Elizabeth Frydrych Golden Gate Sotheby's

Turn-key oasis in the middle of Healdsburg! This property exudes easy Wine Country living with a solar-heated pool in a spa like setting. Located less than one mile from the Healdsburg Plaza, this completely updated single-level was converted from a 4-bedroom into a 3-bedroom, adding an oversized walk-in closet and laundry closet. The remodeled kitchen features Cambria quartz countertops,

Ann Amtower Compass

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

Nestled in Healdsburg near the Plaza, modernized with care and precision this 2-bedroom, 3-bath home blends elegance with small-town appeal. Just a short stroll and you'll have easy access to renowned restaurants, boutique shopping, and local attractions. The spacious living and dining room combo is an inviting highlight, with 9.5-foot high ceilings and stunning glass doors that flood the space

Eric Drew Healdsburg Sotheby's Internati

Welcome to 813 Sparrow Court - a charming single-level home nestled in one of Healdsburg's desirable neighborhoods. This 3-bedroom, 2-bathroom property offers a thoughtful layout with a spacious living room, a dedicated dining area, and a kitchen that seamlessly opens to the family room - ideal for entertaining or everyday living. The roof was replaced just 5 years ago, offering peace of mind

Julian Solano Excellerate Real Estate

Charming 2 Bed/2 Bath Home in a 55+ Adult Community with a Prime Location near amenities. This inviting 2-bedroom, 2-bathroom home offers a harmonious blend of comfort and convenience and a 200+/-sq.ft. Sun room. Situated just across the street from the Clubhouse and Swimming Pool, this property ensures easy access to social and recreational activities. The home is a mere three houses away from

John Torres The Agency

Welcome to 528 Sanns Lane, a stunning 1-story, 4-bedroom, 2-bathroom home located in the heart of Healdsburg. This 2,080-square-foot residence is the perfect blend of modern elegance and an entertainer's paradise, set on a beautifully landscaped .21-acre lot featuring a variety of fruit trees, including Jack Black Fig, Satsuma Mandarin Orange, Gravenstein Apple, Apricots, Fuyu Persimmon, and

Natalee Tappin The Agency

New co-ownership opportunity: Own one-eighth of this professionally managed, turnkey home by Pacaso. 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 the

Joseph Maehler Pacaso Inc

Discover the perfect fusion of modern luxury and the natural beauty of wine country at 8163 W Dry Creek Road. This stunning residence, set on an expansive 1.95 acre parcel, offers 3,236 square feet of sophisticated living space designed for comfort and ease. Step inside to experience a seamless blend of contemporary design and smart functionality. The sleek, modern construction is complemented by

Leslie Hanson Compass

Welcome to your dream retreat in the heart of Sonoma County wine country! This spacious two-bedroom home offers the perfect blend of convenience, comfort, and luxury living. Located just a leisurely stroll away from Healdsburg's celebrated plaza, you'll have easy access to world-class restaurants and lodging, ensuring that every culinary desire is fulfilled and every stay is nothing short of

Peggy Decker The Agency

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

Jeffrey Schween Compass

Modern Sanctuary with Sweeping Views. Nestled on a serene ridge above Healdsburg, this one-acre property is a rare retreat offering panoramic views of the town and beyond. A beautifully remodeled 3-bedroom, 2.5-bath home blends contemporary design with tranquil outdoor living. Meticulously upgraded in 2022, the single-level residence features custom finishes throughout, from the elegant hardwood

Graham Sarasy Healdsburg Sotheby's Int'l Rea

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

A blank canvas awaits for your own design elements in the highly sought after Healdsburg neighborhood of Fitch Mountain Villas. All the exterior of this home has been updated; new cement siding, new roof and new windows - which allows for the next owner to enjoy all the beautification pleasures of updating the original yet clean interior. Situated on a quiet street only a few steps away from the

David Hunt Sonoma Realty Group

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

Niccolo Pigni Engel & Völkers

**Price Improved!** Welcome to 979 Lupine Court, a well-located 4 bedroom, 3 bath, fully-detached home in desirable Piedmont Terrace location. A wonderful lifestyle awaits you in this ample 2,346 sq ft retreat. Lower level features 1 bedroom, 1 full bathroom, large open-plan kitchen with adjoining family room w/ gas fireplace, living and dining rooms. Deck access off kitchen to expansive

Patrick Shannon Trinity Realty, Inc

A contemporary masterpiece nestled in the heart of Healdsburg, a town celebrated for its charm & character. Visually striking & eminently livable, the Glass Pavilion is an architecturally significant home, designed by AIA award-winning architect Stanley Saitowitz - his considerable accomplishments have earned him both the American Institute of Architecture's Innovation Award (2017) & the Cooper

Jeffrey Schween Compass