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Lovely single-level home located in the highly desirable Greens neighborhood. Situated on an approximately 8,900 SF lot backing to Tayman Park Golf Course, 412 Fairway Court offers 2,186 SF of comfortable living space. Nestled on a quiet cul-de-sac, the property features beautiful front landscaping that enhances its curb appeal while providing a welcoming sense of privacy. Despite its peaceful setting, the home enjoys the convenience of being within close proximity of the Healdsburg Plaza, offering easy access to renowned restaurants, tasting rooms, boutiques, and community events. The home features three bedrooms and two full bathrooms, along with both a living room and family room, each highlighted by a cozy wood-burning fireplace. A separate dining room with French doors opens to the rear deck and patio, creating an ideal setting for indoor-outdoor entertaining. The kitchen features a vaulted ceiling and skylight that fills the space with abundant natural light. Beautiful Red Oak hardwood flooring flows throughout the main living areas, adding warmth and character. The spacious primary suite offers a large walk-in closet and an ensuite bathroom complete with both a soaking tub and walk-in shower. A sliding glass door provides direct access from the primary bedroom to the back deck, creating the perfect location for a private hot tub retreat. The expansive backyard offers ample room for a pool, garden, or other outdoor amenities while enjoying the peaceful setting and golf course backdrop of Tayman Park Golf Course and Fitch Mountain.

3 Beds ⋅ 2 Baths ⋅ 326048347 MLS

Lovely single-level home located in the highly desirable Greens neighborhood. Situated on an approximately 8,900 SF lot backing to Tayman Park Golf Course, 412 Fairway Court offers 2,186 SF of comfortable living space. Nestled on a quiet cul-de-sac, the property features beautiful front landscaping that enhances its curb appeal while providing a welcoming sense of privacy. Despite its peaceful setting, the home enjoys the convenience of being within close proximity of the Healdsburg Plaza, offering easy access to renowned restaurants, tasting rooms, boutiques, and community events. The home features three bedrooms and two full bathrooms, along with both a living room and family room, each highlighted by a cozy wood-burning fireplace. A separate dining room with French doors opens to the rear deck and patio, creating an ideal setting for indoor-outdoor entertaining. The kitchen features a vaulted ceiling and skylight that fills the space with abundant natural light. Beautiful Red Oak hardwood flooring flows throughout the main living areas, adding warmth and character. The spacious primary suite offers a large walk-in closet and an ensuite bathroom complete with both a soaking tub and walk-in shower. A sliding glass door provides direct access from the primary bedroom to the back deck, creating the perfect location for a private hot tub retreat. The expansive backyard offers ample room for a pool, garden, or other outdoor amenities while enjoying the peaceful setting and golf course backdrop of Tayman Park Golf Course and Fitch Mountain.

412 Fairway Ct, Healdsburg

$1,800,000

Discover this gracious, single-level 4-bedroom home on an in-town 1.01+/- acre lot. A perfect blend of comfort, functionality, and location. The layout is open and effortless, with vaulted ceilings and large windows that fill the rooms with natural light. The family room and kitchen connect for everyday living and entertaining, with direct access to the outdoors. The spacious primary suite includes a walk-in closet, en suite bath, and French doors leading to the deck. The expansive yard unfolds in every direction with sunny open spaces and the shade of mature redwoods. There is plenty of room to add an ADU, additional gardens, and a pool. A fully paid-for solar system with Tesla backup battery keeps energy costs low while adding lasting value. Another feature is the large 3-car garage. Enjoy the best of both worlds a sense of country privacy with city services, in a beloved and coveted neighborhood.

4 Beds ⋅ 2 Baths ⋅ 326000733 MLS

Discover this gracious, single-level 4-bedroom home on an in-town 1.01+/- acre lot. A perfect blend of comfort, functionality, and location. The layout is open and effortless, with vaulted ceilings and large windows that fill the rooms with natural light. The family room and kitchen connect for everyday living and entertaining, with direct access to the outdoors. The spacious primary suite includes a walk-in closet, en suite bath, and French doors leading to the deck. The expansive yard unfolds in every direction with sunny open spaces and the shade of mature redwoods. There is plenty of room to add an ADU, additional gardens, and a pool. A fully paid-for solar system with Tesla backup battery keeps energy costs low while adding lasting value. Another feature is the large 3-car garage. Enjoy the best of both worlds a sense of country privacy with city services, in a beloved and coveted neighborhood.

219 Burgundy Rd, Healdsburg

$1,757,500

Set on approximately 4.59 level, usable acres just minutes from downtown Healdsburg, this property offers a rare combination of privacy, flexibility, and long-term potential in the heart of Sonoma County wine country. The approximately 1,938+/- sq ft single-level main residence is thoughtfully designed across two wings, creating both separation and functionality. One wing features a walk-in pantry off the dining area, a secondary en-suite bedroom, and an additional bedroom served by a full hall bath. The opposite wing is anchored by a private primary suite with walk-in closet and ensuite bath, along with a half bath, large storage room, and multiple closets. Living spaces open to an expansive redwood deck overlooking the surrounding valley, offering an easy indoor-outdoor connection. A detached approximately 840+/- sq ft ADU provides a full great room, kitchen, and dining area, along with two bedrooms and one full bath, well suited for extended living, guests, or workspace. The property includes a three-car garage, with the third bay currently utilized as a workout studio and filming space. The land is largely level and fully usable, well suited for agriculture, gardens, animals, or future expansion. A designated building envelope is in place for those considering additional improvements or a second residence (buyer to verify). Owned solar is already installed, supporting long-term efficiency. Located approximately 1.2 miles from the Healdsburg Plaza, with convenient access to wineries, dining, and everyday amenities. Ideal for multi-generational living or compound-style use, this is a rare opportunity to secure usable acreage with flexibility and long-term upside in one of Sonoma County's most sought-after locations.

5 Beds ⋅ 5 Baths ⋅ 326038511 MLS

Set on approximately 4.59 level, usable acres just minutes from downtown Healdsburg, this property offers a rare combination of privacy, flexibility, and long-term potential in the heart of Sonoma County wine country. The approximately 1,938+/- sq ft single-level main residence is thoughtfully designed across two wings, creating both separation and functionality. One wing features a walk-in pantry off the dining area, a secondary en-suite bedroom, and an additional bedroom served by a full hall bath. The opposite wing is anchored by a private primary suite with walk-in closet and ensuite bath, along with a half bath, large storage room, and multiple closets. Living spaces open to an expansive redwood deck overlooking the surrounding valley, offering an easy indoor-outdoor connection. A detached approximately 840+/- sq ft ADU provides a full great room, kitchen, and dining area, along with two bedrooms and one full bath, well suited for extended living, guests, or workspace. The property includes a three-car garage, with the third bay currently utilized as a workout studio and filming space. The land is largely level and fully usable, well suited for agriculture, gardens, animals, or future expansion. A designated building envelope is in place for those considering additional improvements or a second residence (buyer to verify). Owned solar is already installed, supporting long-term efficiency. Located approximately 1.2 miles from the Healdsburg Plaza, with convenient access to wineries, dining, and everyday amenities. Ideal for multi-generational living or compound-style use, this is a rare opportunity to secure usable acreage with flexibility and long-term upside in one of Sonoma County's most sought-after locations.

14631 Kinley Dr, Healdsburg

$1,750,000

Don't miss your chance to make this Healdsburg Mid-Century Modern beauty your own! Offering 3 bedrooms, 2 full baths, and an open-concept layout, this home has an easy, comfortable flow that makes everyday living feel a little like a vacation. A versatile room just off the kitchen and living area offers the perfect space for a home office, cozy family room, hobby space, or whatever fits your lifestyle. Thoughtfully upgraded throughout, this home blends elegant finishes with the ultra-clean lines and timeless design that make Mid-Century Modern homes so special. There are too many upgrades to list, and the home has recently been freshly painted inside and out. Step through the slider and take in the beautiful views of your private backyard oasis, complete with a pool and built-in spa. Designed for both relaxation and everyday enjoyment, the backyard offers plenty of space for lounging, gardening, entertaining, and storage. All of this, just a mile from the Healdsburg Plaza, where you can enjoy some of the area's best restaurants, wineries, tasting rooms, and shopping. Come see this special home for yourself, you just might fall in love at first sight!

3 Beds ⋅ 2 Baths ⋅ 326079913 MLS

Don't miss your chance to make this Healdsburg Mid-Century Modern beauty your own! Offering 3 bedrooms, 2 full baths, and an open-concept layout, this home has an easy, comfortable flow that makes everyday living feel a little like a vacation. A versatile room just off the kitchen and living area offers the perfect space for a home office, cozy family room, hobby space, or whatever fits your lifestyle. Thoughtfully upgraded throughout, this home blends elegant finishes with the ultra-clean lines and timeless design that make Mid-Century Modern homes so special. There are too many upgrades to list, and the home has recently been freshly painted inside and out. Step through the slider and take in the beautiful views of your private backyard oasis, complete with a pool and built-in spa. Designed for both relaxation and everyday enjoyment, the backyard offers plenty of space for lounging, gardening, entertaining, and storage. All of this, just a mile from the Healdsburg Plaza, where you can enjoy some of the area's best restaurants, wineries, tasting rooms, and shopping. Come see this special home for yourself, you just might fall in love at first sight!

804 Josephine Ln, Healdsburg

$1,700,000

Location, Location, Location!!! Charming Home in the Heart of Healdsburg!! Desirable Greens neighborhood at the end of a cul-de-sac. This home features, Entry with high ceiling. Stepdown Formal Living room with fireplace. Formal Dining room with doors leading to back yard. Kitchen with tile countertops, and breakfast bar. Family room with skylight, freestanding fireplace and doors leading to back yard. 4 bedrooms, (one downstairs), 3 full baths, (one downstairs). Indoor Laundry room with additional cabinets. Attached two car garage. Primary Bedroom upstairs has high ceiling, walk in closet and primary bath with double sinks, separate tub and shower. R.V. parking! Large Lot!! Lots of storage! Artificial grass in front for water conservation. Shutters throughout. NO HOA.

4 Beds ⋅ 3 Baths ⋅ 325088467 MLS

Location, Location, Location!!! Charming Home in the Heart of Healdsburg!! Desirable Greens neighborhood at the end of a cul-de-sac. This home features, Entry with high ceiling. Stepdown Formal Living room with fireplace. Formal Dining room with doors leading to back yard. Kitchen with tile countertops, and breakfast bar. Family room with skylight, freestanding fireplace and doors leading to back yard. 4 bedrooms, (one downstairs), 3 full baths, (one downstairs). Indoor Laundry room with additional cabinets. Attached two car garage. Primary Bedroom upstairs has high ceiling, walk in closet and primary bath with double sinks, separate tub and shower. R.V. parking! Large Lot!! Lots of storage! Artificial grass in front for water conservation. Shutters throughout. NO HOA.

401 Fairway Ct, Healdsburg

$1,654,000

Set along one of Healdsburg's most picturesque streets, this rare find features two separate bungalow-style homes on a spacious 1/4 acre parcel just minutes from Healdsburg Plaza. With turn-of-the-century character and a just-remodeled interior, the primary home (#133) is a perfect blend of historic and new. Classic bungalow-styling features two bedrooms and one bathroom, approximately 750 sq.ft. of living space, all updated to please the modern aesthetic. Tall ceilings and windows, LED lighting, an inviting front porch, new cabinetry and appliances, luxury vinyl plank flooring, and an energy-efficient mini-split system make this home ready for you to move right in and enjoy. The second home is set to the back of the parcel with its own private entrance and separate house address. Built in a cottage style, this sweet unit is one bedroom, one bath with approximately 647 square feet of living space. The interior is freshly painted with new lighting fixtures. Both homes have air-conditioning, laundry, separate detached garages, and fully fenced yards. This property is truly unique. Two homes on a 1/4 acre lot, two separate addresses, two electric meters, and two water meters. Whether you're envisioning a private family compound, a wine country getaway with guest accommodations, multi-generational living, or the flexibility of a primary residence paired with a second home, the possibilities are as timeless as the homes themselves. Just 0.7 mile from celebrated Healdsburg Plaza, enjoy the perfect balance of neighborhood charm and world-class dining, wineries, and boutique shopping.

3 Beds ⋅ 2 Baths ⋅ 326064711 MLS

Set along one of Healdsburg's most picturesque streets, this rare find features two separate bungalow-style homes on a spacious 1/4 acre parcel just minutes from Healdsburg Plaza. With turn-of-the-century character and a just-remodeled interior, the primary home (#133) is a perfect blend of historic and new. Classic bungalow-styling features two bedrooms and one bathroom, approximately 750 sq.ft. of living space, all updated to please the modern aesthetic. Tall ceilings and windows, LED lighting, an inviting front porch, new cabinetry and appliances, luxury vinyl plank flooring, and an energy-efficient mini-split system make this home ready for you to move right in and enjoy. The second home is set to the back of the parcel with its own private entrance and separate house address. Built in a cottage style, this sweet unit is one bedroom, one bath with approximately 647 square feet of living space. The interior is freshly painted with new lighting fixtures. Both homes have air-conditioning, laundry, separate detached garages, and fully fenced yards. This property is truly unique. Two homes on a 1/4 acre lot, two separate addresses, two electric meters, and two water meters. Whether you're envisioning a private family compound, a wine country getaway with guest accommodations, multi-generational living, or the flexibility of a primary residence paired with a second home, the possibilities are as timeless as the homes themselves. Just 0.7 mile from celebrated Healdsburg Plaza, enjoy the perfect balance of neighborhood charm and world-class dining, wineries, and boutique shopping.

135 Sherman St, Healdsburg

$1,600,000

There is an ease to life at 521 Prince Avenue that captures the best of in-town Healdsburg living. Originally built in 1910, this beautifully renovated single-level home blends classic period charm with modern comfort, high-end finishes, and a distinctly Wine Country sense of place. From its inviting exterior, wrap-around porch, and original water tower to its warm, refined interior, the home offers character without compromise. Inside, the three-bedroom, two-bath floor plan is open, comfortable, and thoughtfully designed for everyday living or relaxed weekend escapes. The remodeled kitchen features high-end appliances and flows naturally into the dining and living spaces, where oak flooring, smooth textured walls, updated windows, 8-foot doors, and a gas fireplace with reclaimed timber mantel create a polished yet welcoming atmosphere. The primary suite includes double walk-in closets and direct access to a spacious rear deck, offering a quiet place to begin or end the day. The outdoor spaces are designed for ease, with usable areas to enjoy without the burden of maintaining a large yard. Xeriscaped landscaping, updated fencing, exterior lighting, and a detached one-car garage further support the low-maintenance lifestyle. Set just a few blocks from the Healdsburg Plaza, the home offers exceptional access to downtown restaurants, tasting rooms, boutiques, parks, and the broader Wine Country experience. Whether used as a luxury getaway or a full-time residence, 521 Prince Avenue delivers historic charm, turnkey comfort, and effortless connection to one of Sonoma County's most desirable lifestyle destinations.

3 Beds ⋅ 2 Baths ⋅ 326029431 MLS

There is an ease to life at 521 Prince Avenue that captures the best of in-town Healdsburg living. Originally built in 1910, this beautifully renovated single-level home blends classic period charm with modern comfort, high-end finishes, and a distinctly Wine Country sense of place. From its inviting exterior, wrap-around porch, and original water tower to its warm, refined interior, the home offers character without compromise. Inside, the three-bedroom, two-bath floor plan is open, comfortable, and thoughtfully designed for everyday living or relaxed weekend escapes. The remodeled kitchen features high-end appliances and flows naturally into the dining and living spaces, where oak flooring, smooth textured walls, updated windows, 8-foot doors, and a gas fireplace with reclaimed timber mantel create a polished yet welcoming atmosphere. The primary suite includes double walk-in closets and direct access to a spacious rear deck, offering a quiet place to begin or end the day. The outdoor spaces are designed for ease, with usable areas to enjoy without the burden of maintaining a large yard. Xeriscaped landscaping, updated fencing, exterior lighting, and a detached one-car garage further support the low-maintenance lifestyle. Set just a few blocks from the Healdsburg Plaza, the home offers exceptional access to downtown restaurants, tasting rooms, boutiques, parks, and the broader Wine Country experience. Whether used as a luxury getaway or a full-time residence, 521 Prince Avenue delivers historic charm, turnkey comfort, and effortless connection to one of Sonoma County's most desirable lifestyle destinations.

521 Prince Ave, Healdsburg

$1,575,000

Live, Invest, or Build Your Dream Home in Downtown Healdsburg - Exceptional opportunity in downtown Healdsburg. Located on a sought-after quiet dead-end street just blocks from the Healdsburg Plaza, this single-story duplex offers flexibility, income potential, and an unbeatable location. The property includes two units, each with a private yard and dedicated laundry. Unit 327 features 2 bedrooms, 1 bathroom, and an attached one-car garage, while Unit 329 offers 3 bedrooms, 2 bathrooms, and a garage conversion providing valuable additional living or storage space. With approximately 2,099 square feet on a 6,300 square foot lot, the property presents a variety of possibilities for investors, owner-occupants, and those seeking a premier downtown location. Continue operating as an income-producing duplex, live in one unit while generating rental income from the other, or take advantage of this exceptional in-town setting to create the custom Healdsburg home you've always envisioned. Opportunities to secure a property with this combination of flexibility, location, and future potential are increasingly rare. Just a couple blocks from the vibrant shops, restaurants, tasting rooms, and community events of downtown Healdsburg, this is a unique chance to invest in one of Sonoma County's most desirable neighborhoods.

5 Beds ⋅ 3 Baths ⋅ 326048500 MLS

Live, Invest, or Build Your Dream Home in Downtown Healdsburg - Exceptional opportunity in downtown Healdsburg. Located on a sought-after quiet dead-end street just blocks from the Healdsburg Plaza, this single-story duplex offers flexibility, income potential, and an unbeatable location. The property includes two units, each with a private yard and dedicated laundry. Unit 327 features 2 bedrooms, 1 bathroom, and an attached one-car garage, while Unit 329 offers 3 bedrooms, 2 bathrooms, and a garage conversion providing valuable additional living or storage space. With approximately 2,099 square feet on a 6,300 square foot lot, the property presents a variety of possibilities for investors, owner-occupants, and those seeking a premier downtown location. Continue operating as an income-producing duplex, live in one unit while generating rental income from the other, or take advantage of this exceptional in-town setting to create the custom Healdsburg home you've always envisioned. Opportunities to secure a property with this combination of flexibility, location, and future potential are increasingly rare. Just a couple blocks from the vibrant shops, restaurants, tasting rooms, and community events of downtown Healdsburg, this is a unique chance to invest in one of Sonoma County's most desirable neighborhoods.

327 Plaza St, Healdsburg

$1,575,000

An elegant 1918 craftsman bungalow on one of Healdsburg's most coveted residential streets, just blocks from the Plaza. Few addresses in Healdsburg offer this kind of proximity combined with this much character. Inside, restored original fir floors, built-in cabinetry, and a quartzite kitchen with stainless appliances and a coffee bar nook with an additional sink. Two spacious walk-in closets and a thoughtfully added second full bath make the home as functional as it is charming. Step outside and the property opens up. A beautifully landscaped front and back yard with shaded porches is made for outdoor living. At the back of the property, a finished garage with its own split heating and cooling system offers flexible space ready for a home office, studio, or creative retreat. Newer roof and newer exterior paint complete the picture.

2 Beds ⋅ 2 Baths ⋅ 326042637 MLS

An elegant 1918 craftsman bungalow on one of Healdsburg's most coveted residential streets, just blocks from the Plaza. Few addresses in Healdsburg offer this kind of proximity combined with this much character. Inside, restored original fir floors, built-in cabinetry, and a quartzite kitchen with stainless appliances and a coffee bar nook with an additional sink. Two spacious walk-in closets and a thoughtfully added second full bath make the home as functional as it is charming. Step outside and the property opens up. A beautifully landscaped front and back yard with shaded porches is made for outdoor living. At the back of the property, a finished garage with its own split heating and cooling system offers flexible space ready for a home office, studio, or creative retreat. Newer roof and newer exterior paint complete the picture.

437 North St, Healdsburg

$1,575,000

Fabulous 4 bedroom home on a large .19 acre lot that has been freshly painted inside and out and has easy access to downtown Healdsburg. This spacious home has lots of windows and natural light with the main primary suite downstairs and another 3 bedrooms upstairs including one on suite. Enter the home onto the gorgeous wood floors. Plenty of entertaining spaces with a living room, family room with a fireplace and some built ins and a separate dining room off of the butlers panty. This 2450 square foot home sits on a beautifully landscaped lot with mature trees. A kitchen built for entertaining family and friends, updated lighting and high ceilings make this the perfect place to move right in and start enjoying all that Healdsburg has to offer. In addition this home is on a cul-de-sac and there is a detached garage and room for a pool, gardening and so much more!

4 Beds ⋅ 4 Baths ⋅ 326034631 MLS

Fabulous 4 bedroom home on a large .19 acre lot that has been freshly painted inside and out and has easy access to downtown Healdsburg. This spacious home has lots of windows and natural light with the main primary suite downstairs and another 3 bedrooms upstairs including one on suite. Enter the home onto the gorgeous wood floors. Plenty of entertaining spaces with a living room, family room with a fireplace and some built ins and a separate dining room off of the butlers panty. This 2450 square foot home sits on a beautifully landscaped lot with mature trees. A kitchen built for entertaining family and friends, updated lighting and high ceilings make this the perfect place to move right in and start enjoying all that Healdsburg has to offer. In addition this home is on a cul-de-sac and there is a detached garage and room for a pool, gardening and so much more!

997 Lupine Ct, Healdsburg

$1,550,000

This recently updated, move-in ready home is located in one of Healdsburg's most desirable neighborhoods and offers four bedrooms, including a versatile room ideal as a home office or library, along with 2.5 bathrooms, two of which feature heated floors. The light-filled kitchen is appointed with stainless steel appliances and granite countertops. The fenced backyard is designed for enjoying Wine Country's indoor-outdoor lifestyle, featuring a pool, garden area with raised beds, all while backing to a tranquil open space area. Ideally situated in the heart of Wine Country between Healdsburg's renowned Dry Creek Valley and Alexander Valley, the home is just minutes from Lake Sonoma, offering exceptional fishing, camping, and outdoor recreation. Enjoy a short drive to the vibrant Healdsburg Plaza, home to acclaimed restaurants, tasting rooms, boutique shopping, live music venues, and the popular Farmers Market at the Foley Family Pavilion. With convenient access to Highway 101, San Francisco and the greater Bay Area are within easy reach, and the Sonoma County Airport is just minutes away. Full property photos and video will be on-line on or before 6.13.2026

4 Beds ⋅ 3 Baths ⋅ 326049590 MLS

This recently updated, move-in ready home is located in one of Healdsburg's most desirable neighborhoods and offers four bedrooms, including a versatile room ideal as a home office or library, along with 2.5 bathrooms, two of which feature heated floors. The light-filled kitchen is appointed with stainless steel appliances and granite countertops. The fenced backyard is designed for enjoying Wine Country's indoor-outdoor lifestyle, featuring a pool, garden area with raised beds, all while backing to a tranquil open space area. Ideally situated in the heart of Wine Country between Healdsburg's renowned Dry Creek Valley and Alexander Valley, the home is just minutes from Lake Sonoma, offering exceptional fishing, camping, and outdoor recreation. Enjoy a short drive to the vibrant Healdsburg Plaza, home to acclaimed restaurants, tasting rooms, boutique shopping, live music venues, and the popular Farmers Market at the Foley Family Pavilion. With convenient access to Highway 101, San Francisco and the greater Bay Area are within easy reach, and the Sonoma County Airport is just minutes away. Full property photos and video will be on-line on or before 6.13.2026

1100 Sunnyside Dr, Healdsburg

$1,545,000

Prime Healdsburg Living Meets Incredible Potential. Nestled in the coveted Greens neighborhood, 410 Tee Drive presents a rare opportunity to secure a substantial 2,686 square foot residence in one of Healdsburg's most established enclaves. Featuring a classic wrap around porch and a floor plan designed for effortless flow, this home serves as the perfect canvas for your modern vision. The main level offers multiple living spaces designed for flexibility, anchored by a fireplace that adds warmth to the home's original character. The kitchen flows seamlessly to the backyard, making it an ideal setup for indoor-outdoor entertaining. Upstairs you will find the primary suite with a spacious bathroom featuring a shower and soaking tub, plus a walk-in closet. Two additional bedrooms and a second full bathroom also live upstairs. The oversized two-car garage includes a built-in workshop, while a separate mudroom and utility room complete with a full bathroom is conveniently located between the garage and the main house. The expansive backyard is a gardener's dream, featuring established citrus and fruit trees, a large deck, and dedicated space for a farm-to-table kitchen garden. Whether you are enjoying everything the Healdsburg Plaza has to offer, teeing off at Tayman Park, or exploring the Russian River or trails of Fitch Mountain, the location is truly second to none. Live comfortable in this home or bring your vision to transform this spacious property into your dream home.

3 Beds ⋅ 3 Baths ⋅ 326036825 MLS

Prime Healdsburg Living Meets Incredible Potential. Nestled in the coveted Greens neighborhood, 410 Tee Drive presents a rare opportunity to secure a substantial 2,686 square foot residence in one of Healdsburg's most established enclaves. Featuring a classic wrap around porch and a floor plan designed for effortless flow, this home serves as the perfect canvas for your modern vision. The main level offers multiple living spaces designed for flexibility, anchored by a fireplace that adds warmth to the home's original character. The kitchen flows seamlessly to the backyard, making it an ideal setup for indoor-outdoor entertaining. Upstairs you will find the primary suite with a spacious bathroom featuring a shower and soaking tub, plus a walk-in closet. Two additional bedrooms and a second full bathroom also live upstairs. The oversized two-car garage includes a built-in workshop, while a separate mudroom and utility room complete with a full bathroom is conveniently located between the garage and the main house. The expansive backyard is a gardener's dream, featuring established citrus and fruit trees, a large deck, and dedicated space for a farm-to-table kitchen garden. Whether you are enjoying everything the Healdsburg Plaza has to offer, teeing off at Tayman Park, or exploring the Russian River or trails of Fitch Mountain, the location is truly second to none. Live comfortable in this home or bring your vision to transform this spacious property into your dream home.

410 Tee Dr, Healdsburg

$1,435,000

Wonderful opportunity in Downtown Healdsburg. Two single story move in ready homes with a total of 4 bedrooms set back off of University on a private lane offering spacious yards, ample parking, and separate garages. The larger home has 2 bedrooms and 2 baths and has recent updates including fresh interior paint and a primary bathroom. Some additional amenities include travertine flooring, a modern kitchen with quality cabinetry, stunning countertops and high end appliances. The breakfast nook looks out to the sunny backyard which offers lots of space to garden or relax. The smaller home also has 2 bedrooms and was updated with new paint, flooring, freshly painted cabinets and more. These homes sit on a lot just under 10,000 square feet and are a perfect opportunity for an extended family needing an in-law unit, someone looking to live in one and rent the other or an investment opportunity. The downtown Healdsburg lifestyle is waiting for you with small town coffee shops, fine dining and a fabulous farmers market just a few blocks away.

4 Beds ⋅ 3 Baths ⋅ 326015062 MLS

Wonderful opportunity in Downtown Healdsburg. Two single story move in ready homes with a total of 4 bedrooms set back off of University on a private lane offering spacious yards, ample parking, and separate garages. The larger home has 2 bedrooms and 2 baths and has recent updates including fresh interior paint and a primary bathroom. Some additional amenities include travertine flooring, a modern kitchen with quality cabinetry, stunning countertops and high end appliances. The breakfast nook looks out to the sunny backyard which offers lots of space to garden or relax. The smaller home also has 2 bedrooms and was updated with new paint, flooring, freshly painted cabinets and more. These homes sit on a lot just under 10,000 square feet and are a perfect opportunity for an extended family needing an in-law unit, someone looking to live in one and rent the other or an investment opportunity. The downtown Healdsburg lifestyle is waiting for you with small town coffee shops, fine dining and a fabulous farmers market just a few blocks away.

433 University St, Healdsburg

$1,400,000

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 fireplace and inviting living and dining rooms. Kitchen opens to expansive pool/outdoor entertaining areas which includes custom electric awning. Dining room accesses the wraparound front porch. Upper floor features 3 bedrooms, including primary bedroom with en-suite w/ lovely basking tub and walk-in shower, additional full bath, and separate laundry room with appliances. Additional features include lovely hardwood and tile flooring, dramatic 2-story entry foyer w/ grand staircase, and grand high ceilings. This wine country retreat also includes 2-car garage w/ ample storage, dual-zone heating and cooling systems. Recently professionally painted throughout. This exceptional home sits atop a generous 7,231 sq ft private-feeling lot adjacent to privately-owned open space for additional privacy. Walking distance to lovely downtown Healdsburg and it's many shops and restaurants.

4 Beds ⋅ 3 Baths ⋅ 326038370 MLS

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 fireplace and inviting living and dining rooms. Kitchen opens to expansive pool/outdoor entertaining areas which includes custom electric awning. Dining room accesses the wraparound front porch. Upper floor features 3 bedrooms, including primary bedroom with en-suite w/ lovely basking tub and walk-in shower, additional full bath, and separate laundry room with appliances. Additional features include lovely hardwood and tile flooring, dramatic 2-story entry foyer w/ grand staircase, and grand high ceilings. This wine country retreat also includes 2-car garage w/ ample storage, dual-zone heating and cooling systems. Recently professionally painted throughout. This exceptional home sits atop a generous 7,231 sq ft private-feeling lot adjacent to privately-owned open space for additional privacy. Walking distance to lovely downtown Healdsburg and it's many shops and restaurants.

979 Lupine Ct, Healdsburg

$1,395,000

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 with full bath ideal as a guest retreat, office, or creative studio plus a convenient main-level half bath. Light-filled interiors showcase soaring vaulted ceilings, south-facing windows, white oak flooring, mosaic tile accents, fresh paint, and updated quartz countertops. The chef's kitchen features a gas range and newer, high-end appliances, seamlessly connecting to open living spaces designed for both everyday comfort and effortless entertaining. Step outside to a private deck with a gas log fireplace and tranquil views over a seasonal creek your own serene escape. Set within a peaceful grove yet moments from the energy of downtown, enjoy walkable access to acclaimed dining, boutique tasting rooms featuring Alexander Valley and Dry Creek Valley wines, and vibrant market mornings. Community amenities include a pool, spa, BBQ area, and HOA-maintained grounds, along with a one-car garage offering the perfect balance of luxury, convenience, and Wine Country living.

2 Beds ⋅ 3 Baths ⋅ 326019262 MLS

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 with full bath ideal as a guest retreat, office, or creative studio plus a convenient main-level half bath. Light-filled interiors showcase soaring vaulted ceilings, south-facing windows, white oak flooring, mosaic tile accents, fresh paint, and updated quartz countertops. The chef's kitchen features a gas range and newer, high-end appliances, seamlessly connecting to open living spaces designed for both everyday comfort and effortless entertaining. Step outside to a private deck with a gas log fireplace and tranquil views over a seasonal creek your own serene escape. Set within a peaceful grove yet moments from the energy of downtown, enjoy walkable access to acclaimed dining, boutique tasting rooms featuring Alexander Valley and Dry Creek Valley wines, and vibrant market mornings. Community amenities include a pool, spa, BBQ area, and HOA-maintained grounds, along with a one-car garage offering the perfect balance of luxury, convenience, and Wine Country living.

516 Grove St, Healdsburg

$1,330,250

This wonderful home sits on a 9980 s.f. lot with a generous 1877 s.f. floorplan. The entry leads to a formal living room and dining area which flows into a large kitchen with eat-in area plus island, and a family room with fireplace. There are 3 bedrooms, 2 bathrooms, and another room situated just off the entry which is perfectly suited for an office or study, but has a closet and could be used as a 4th bedroom. There is a brand new deck on the back of the house leading to the fenced backyard, also a brand new water heater, a 2020 roof and 2019 furnace. Plenty of room to bring your personal touches to this wonderful home. An excellent choice for family, executives or retirees to reside in a quiet neighborhood about .7 mile from the historic Healdsburg Plaza. Enjoy all the vibrancy Healdsburg has to offer in world-class dining, art galleries, wine tasting, outdoor adventures and Tuesday Concerts in the Plaza.

4 Beds ⋅ 2 Baths ⋅ 325078091 MLS

This wonderful home sits on a 9980 s.f. lot with a generous 1877 s.f. floorplan. The entry leads to a formal living room and dining area which flows into a large kitchen with eat-in area plus island, and a family room with fireplace. There are 3 bedrooms, 2 bathrooms, and another room situated just off the entry which is perfectly suited for an office or study, but has a closet and could be used as a 4th bedroom. There is a brand new deck on the back of the house leading to the fenced backyard, also a brand new water heater, a 2020 roof and 2019 furnace. Plenty of room to bring your personal touches to this wonderful home. An excellent choice for family, executives or retirees to reside in a quiet neighborhood about .7 mile from the historic Healdsburg Plaza. Enjoy all the vibrancy Healdsburg has to offer in world-class dining, art galleries, wine tasting, outdoor adventures and Tuesday Concerts in the Plaza.

421 Tee Dr, Healdsburg

$1,330,000

Step into your own private oasis at the end of a lane with custom homes around. Complete tranquility with this premier Healdsburg location, just minutes from downtown Healdsburg with its renowned restaurants, wineries, and boutiques, yet on all city services, no septic or well. The meticulously renovated 3-bedroom, 2-full-bathroom main house spans 1728 square feet of luxurious living with premium finishes throughout. The bonus room features a full bathroom and endless potential with approximately 630 sqft of finished space. The chef's kitchen showcases new countertops and backsplash and high-end Kitchenaid appliances, while new engineered hardwood floors flow seamlessly throughout the home. The primary suite features a generous en-suite bathroom and walk-in closet. Your outdoor paradise includes an extensively rebuilt wrap-around deck, expansive flat areas perfect for a pool, outdoor kitchen, bocce court, RV parking, and more. Additional upgrades include a newer roof, newer windows, and more. The mature landscaping features an abundance of trees, adding both beauty and seasonal bounty to this exceptional estate.This turnkey property perfectly balances resort-style luxury with the convenience of wine country living.

3 Beds ⋅ 3 Baths ⋅ 325102816 MLS

Step into your own private oasis at the end of a lane with custom homes around. Complete tranquility with this premier Healdsburg location, just minutes from downtown Healdsburg with its renowned restaurants, wineries, and boutiques, yet on all city services, no septic or well. The meticulously renovated 3-bedroom, 2-full-bathroom main house spans 1728 square feet of luxurious living with premium finishes throughout. The bonus room features a full bathroom and endless potential with approximately 630 sqft of finished space. The chef's kitchen showcases new countertops and backsplash and high-end Kitchenaid appliances, while new engineered hardwood floors flow seamlessly throughout the home. The primary suite features a generous en-suite bathroom and walk-in closet. Your outdoor paradise includes an extensively rebuilt wrap-around deck, expansive flat areas perfect for a pool, outdoor kitchen, bocce court, RV parking, and more. Additional upgrades include a newer roof, newer windows, and more. The mature landscaping features an abundance of trees, adding both beauty and seasonal bounty to this exceptional estate.This turnkey property perfectly balances resort-style luxury with the convenience of wine country living.

210 Burgundy Rd, Healdsburg

$1,325,000

Nestled on a tranquil 1.8-acre parcel, this single-story ranch offers the best of Healdsburg living with its peaceful country charm yet close to world-renowned wineries and culinary destinations just minutes away. Inside, the approx. 2,000-sqft floor plan, offers easy single-level living, a great room with a cozy fireplace, and a separate living room each bathed in natural light with accents of warm wood hues. The chef's kitchen features quartz countertops, double ovens with a cafe door, and a pantry. The primary suite offers direct access to the hot tub area, while the ensuite bathroom has been updated with designer touches. The property is private, backing to a creek and framed by 61 mature olive trees harvested by the owners to produce their own estate olive oil. This property is a rare blend of rural elegance and everyday comfort. Designed with entertaining and relaxed outdoor living in mind, the home opens to expansive decks ideal for al fresco dining and sunset lounging. An outdoor kitchen complete with a wood-fired pizza oven invites memorable gatherings, while a hot tub under the stars promises year-round indulgence. Native gardens, thoughtful landscaping, a chicken coop, and parking for 8+ vehicles round out the property's lifestyle offerings. A true wine country gem!

3 Beds ⋅ 3 Baths ⋅ 326012604 MLS

Nestled on a tranquil 1.8-acre parcel, this single-story ranch offers the best of Healdsburg living with its peaceful country charm yet close to world-renowned wineries and culinary destinations just minutes away. Inside, the approx. 2,000-sqft floor plan, offers easy single-level living, a great room with a cozy fireplace, and a separate living room each bathed in natural light with accents of warm wood hues. The chef's kitchen features quartz countertops, double ovens with a cafe door, and a pantry. The primary suite offers direct access to the hot tub area, while the ensuite bathroom has been updated with designer touches. The property is private, backing to a creek and framed by 61 mature olive trees harvested by the owners to produce their own estate olive oil. This property is a rare blend of rural elegance and everyday comfort. Designed with entertaining and relaxed outdoor living in mind, the home opens to expansive decks ideal for al fresco dining and sunset lounging. An outdoor kitchen complete with a wood-fired pizza oven invites memorable gatherings, while a hot tub under the stars promises year-round indulgence. Native gardens, thoughtful landscaping, a chicken coop, and parking for 8+ vehicles round out the property's lifestyle offerings. A true wine country gem!

14856 Chalk Hill Rd, Healdsburg

$1,320,000

Discover the best of Healdsburg living in this beautifully refreshed 3-bedroom, 2.5-bathroom home offering 2,208 square feet on nearly half an acre. Tucked away on a peaceful dead-end street, this inviting property is just minutes from the iconic Healdsburg Plaza, placing exceptional dining, wine tasting, shopping, and entertainment close at hand. Thoughtfully updated with fresh interior and exterior paint, a remodeled kitchen, new flooring, and numerous additional improvements, the home offers a stylish, comfortable, and move-in-ready setting. Views add another special dimension, creating a beautiful backdrop and a wonderful connection to the surrounding Wine Country landscape. Outside, the property truly shines as a private backyard retreat. An in-ground pool and spa are complemented by a spacious patio, creating the perfect setting for sunny afternoons, evening swims, outdoor dining, and entertaining with friends and family. Garden beds and generous yard space offer plenty of room for gardening and enjoying the outdoors. With its peaceful setting, expansive lot, inviting views, resort-like backyard, and proximity to downtown Healdsburg, this home offers a rare combination of privacy and convenience. Enjoy the space and tranquility of a residential retreat while being just minutes from everything that makes Healdsburg one of Wine Country's most desirable destinations.

3 Beds ⋅ 3 Baths ⋅ 326071481 MLS

Discover the best of Healdsburg living in this beautifully refreshed 3-bedroom, 2.5-bathroom home offering 2,208 square feet on nearly half an acre. Tucked away on a peaceful dead-end street, this inviting property is just minutes from the iconic Healdsburg Plaza, placing exceptional dining, wine tasting, shopping, and entertainment close at hand. Thoughtfully updated with fresh interior and exterior paint, a remodeled kitchen, new flooring, and numerous additional improvements, the home offers a stylish, comfortable, and move-in-ready setting. Views add another special dimension, creating a beautiful backdrop and a wonderful connection to the surrounding Wine Country landscape. Outside, the property truly shines as a private backyard retreat. An in-ground pool and spa are complemented by a spacious patio, creating the perfect setting for sunny afternoons, evening swims, outdoor dining, and entertaining with friends and family. Garden beds and generous yard space offer plenty of room for gardening and enjoying the outdoors. With its peaceful setting, expansive lot, inviting views, resort-like backyard, and proximity to downtown Healdsburg, this home offers a rare combination of privacy and convenience. Enjoy the space and tranquility of a residential retreat while being just minutes from everything that makes Healdsburg one of Wine Country's most desirable destinations.

620 Alta Vista Dr, Healdsburg

$1,300,000

Discover this updated bungalow at 635 Brown Street, Healdsburg, CA, where timeless charm blends seamlessly with modern convenience. The main house offers 2 spacious bedrooms and 2.5 bathrooms, thoughtfully designed across 1,839 square feet to provide both comfort and style. Relax and entertain on the rear deck or enjoy an evening with friends on the front porch. Additionally, the property features a detached Accessory Dwelling Unit with 1 bedroom and 1 bathroom, offering flexibility and potential-live in one and rent the other. This home combines the charm of classic features with the convenience of modern living, all situated in the friendly community of Healdsburg.

3 Beds ⋅ 4 Baths ⋅ 325060490 MLS

Discover this updated bungalow at 635 Brown Street, Healdsburg, CA, where timeless charm blends seamlessly with modern convenience. The main house offers 2 spacious bedrooms and 2.5 bathrooms, thoughtfully designed across 1,839 square feet to provide both comfort and style. Relax and entertain on the rear deck or enjoy an evening with friends on the front porch. Additionally, the property features a detached Accessory Dwelling Unit with 1 bedroom and 1 bathroom, offering flexibility and potential-live in one and rent the other. This home combines the charm of classic features with the convenience of modern living, all situated in the friendly community of Healdsburg.

635 Brown St, Healdsburg

$1,300,000

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 charmall just minutes from downtown Healdsburg and world-class wineries.

2 Beds ⋅ 2 Baths ⋅ 325040931 MLS

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 charmall just minutes from downtown Healdsburg and world-class wineries.

2267 Westside Rd, Healdsburg

$1,200,000

RARE opportunity to own your own office building in Healdsburg or hold as an investment property. This attached office Condo is One block from City Hall, four blocks to Plaza 15 min to Sonoma County Airport 2,500 sf on two floors. Walk to adjoining Park Point Health Club. Ample parking at your front door. Walk to lunch and a dozen great restaurants. 6% cap rate on existing lease.

325094792 MLS

RARE opportunity to own your own office building in Healdsburg or hold as an investment property. This attached office Condo is One block from City Hall, four blocks to Plaza 15 min to Sonoma County Airport 2,500 sf on two floors. Walk to adjoining Park Point Health Club. Ample parking at your front door. Walk to lunch and a dozen great restaurants. 6% cap rate on existing lease.

225 Foss Creek Cir, Healdsburg

$1,150,000

Ideally located in Healdsburg's highly desirable Parkland Farms neighborhood, this spacious 5-bedroom, 3-bath home offers approximately 2,500 sq ft just minutes from the Healdsburg Plaza, renowned wineries, restaurants, shopping, parks, and scenic walking trails. Designed with both comfort and functionality in mind, the flexible floor plan features a full bedroom and bathroom on the main level, formal living and dining rooms, fresh interior paint, updated flooring, plantation shutters, and an open-concept kitchen, dining, and family room centered around a cozy gas fireplace. French doors lead to the backyard, creating seamless indoor-outdoor living. Upstairs, the generous primary suite offers a walk-in closet, soaking tub, and dual-sink vanity, while three additional bedrooms and an upstairs laundry room provide plenty of space for family or guests. Outside, enjoy a low-maintenance backyard complete with a built-in BBQ, outdoor kitchen, paver patio, detached two-car garage, and gated driveway, perfect for entertaining and everyday living. With its unbeatable location, versatile layout, and easy access to everything Healdsburg has to offer, this home is the perfect place to enjoy Wine Country living.

5 Beds ⋅ 3 Baths ⋅ 326043689 MLS

Ideally located in Healdsburg's highly desirable Parkland Farms neighborhood, this spacious 5-bedroom, 3-bath home offers approximately 2,500 sq ft just minutes from the Healdsburg Plaza, renowned wineries, restaurants, shopping, parks, and scenic walking trails. Designed with both comfort and functionality in mind, the flexible floor plan features a full bedroom and bathroom on the main level, formal living and dining rooms, fresh interior paint, updated flooring, plantation shutters, and an open-concept kitchen, dining, and family room centered around a cozy gas fireplace. French doors lead to the backyard, creating seamless indoor-outdoor living. Upstairs, the generous primary suite offers a walk-in closet, soaking tub, and dual-sink vanity, while three additional bedrooms and an upstairs laundry room provide plenty of space for family or guests. Outside, enjoy a low-maintenance backyard complete with a built-in BBQ, outdoor kitchen, paver patio, detached two-car garage, and gated driveway, perfect for entertaining and everyday living. With its unbeatable location, versatile layout, and easy access to everything Healdsburg has to offer, this home is the perfect place to enjoy Wine Country living.

367 Arabian Way, Healdsburg

$1,130,000

Sweeping southwest views across the Coast Range and a private setting make this Wine Country home feel worlds away, yet Healdsburg Plaza is just seven minutes away. Natural light fills the single-level home through skylights, large windows, and multiple glass doors. The great room features a fireplace and opens to a spacious view deck, creating a natural extension of the living space. The kitchen offers a center island, generous storage, and direct access to a charming brick patio with a built-in BBQ and refrigerator. The primary suite opens to the view deck and includes a walk-in closet and an updated bath with dual shower heads. A second ensuite bedroom provides privacy for guests, while the third bedroom offers flexibility for an office or additional sleeping space. Fitch Mountain Park and Open Space Preserve hiking trails are an easy walk from the property. Whether you're looking for a full-time home or a weekend Wine Country getaway, this property offers privacy, beautiful views, and convenient access to Healdsburg's restaurants, tasting rooms, shops, and seasonal events.

3 Beds ⋅ 3 Baths ⋅ 326060643 MLS

Sweeping southwest views across the Coast Range and a private setting make this Wine Country home feel worlds away, yet Healdsburg Plaza is just seven minutes away. Natural light fills the single-level home through skylights, large windows, and multiple glass doors. The great room features a fireplace and opens to a spacious view deck, creating a natural extension of the living space. The kitchen offers a center island, generous storage, and direct access to a charming brick patio with a built-in BBQ and refrigerator. The primary suite opens to the view deck and includes a walk-in closet and an updated bath with dual shower heads. A second ensuite bedroom provides privacy for guests, while the third bedroom offers flexibility for an office or additional sleeping space. Fitch Mountain Park and Open Space Preserve hiking trails are an easy walk from the property. Whether you're looking for a full-time home or a weekend Wine Country getaway, this property offers privacy, beautiful views, and convenient access to Healdsburg's restaurants, tasting rooms, shops, and seasonal events.

1026 Sunset Dr, Healdsburg

$1,050,000

9206 Chalk Hill Road offers a thoughtful expression of Wine Country living, where natural surroundings, everyday comfort and careful stewardship come together. Set on approximately 1.38 acres, the property follows the natural contours of the hillside, with mature native oaks, a seasonal creek and a landscape that changes beautifully with the seasons. Inside, the home has an open, natural flow with soaring vaulted ceilings, expansive windows and abundant natural light. The kitchen, dining and living areas connect seamlessly, while the bedrooms and primary living spaces are arranged on one level for an easy, functional floor plan once inside. An expansive deck extends the living space into the surrounding landscape and an fenced-in patio off the kitchen completes the ease for this property's indoor-outdoor lifestyle. Outdoor living continues to unfold throughout the property. A lower terrace with cafe lighting and a custom wet bar has become a favorite gathering place, while the upper deck offers a different perspective among the oaks. A versatile loft adjoining the garage provides additional flexibility for an office, art studio, fitness room or hobby space. Owned solar, an EV charger and new appliances reflect the attentive ownership and thoughtful care that has been poured into this home for years. Just minutes from both Windsor and Healdsburg, this is a beautiful, well-maintained home for buyers who appreciate room to breathe, natural surroundings and the character of the Chalk Hill setting.

3 Beds ⋅ 2 Baths ⋅ 326068867 MLS

9206 Chalk Hill Road offers a thoughtful expression of Wine Country living, where natural surroundings, everyday comfort and careful stewardship come together. Set on approximately 1.38 acres, the property follows the natural contours of the hillside, with mature native oaks, a seasonal creek and a landscape that changes beautifully with the seasons. Inside, the home has an open, natural flow with soaring vaulted ceilings, expansive windows and abundant natural light. The kitchen, dining and living areas connect seamlessly, while the bedrooms and primary living spaces are arranged on one level for an easy, functional floor plan once inside. An expansive deck extends the living space into the surrounding landscape and an fenced-in patio off the kitchen completes the ease for this property's indoor-outdoor lifestyle. Outdoor living continues to unfold throughout the property. A lower terrace with cafe lighting and a custom wet bar has become a favorite gathering place, while the upper deck offers a different perspective among the oaks. A versatile loft adjoining the garage provides additional flexibility for an office, art studio, fitness room or hobby space. Owned solar, an EV charger and new appliances reflect the attentive ownership and thoughtful care that has been poured into this home for years. Just minutes from both Windsor and Healdsburg, this is a beautiful, well-maintained home for buyers who appreciate room to breathe, natural surroundings and the character of the Chalk Hill setting.

9206 Chalk Hill Rd, Healdsburg

$1,050,000

Perched in the hills overlooking Healdsburg, this well maintained 3 bedroom 2 1/2 bath home has amazing views of the surrounding mountains and vineyards. The kitchen has newer quartz counters and stainless appliances. Other updates include hardwood floors, new HVAC, dual pane windows, gutter guards, and a beautiful Trex deck. The peaceful backyard is elegantly landscaped and ready for your summertime entertaining.

3 Beds ⋅ 3 Baths ⋅ 326054923 MLS

Perched in the hills overlooking Healdsburg, this well maintained 3 bedroom 2 1/2 bath home has amazing views of the surrounding mountains and vineyards. The kitchen has newer quartz counters and stainless appliances. Other updates include hardwood floors, new HVAC, dual pane windows, gutter guards, and a beautiful Trex deck. The peaceful backyard is elegantly landscaped and ready for your summertime entertaining.

860 March Ave, Healdsburg

$1,050,000

This is a must see. You will love this charming 1940s single-story cottage, located less than a mile from the vibrant Healdsburg Plaza. This inviting 2-bedroom, 2-bath home offers approximately 928 square feet of living space and has been thoughtfully updated over the years. Interior highlights include vaulted ceilings, a cozy fireplace, and an open-concept floor plan that creates a bright and welcoming atmosphere. Love the ivy covered front courtyard, private space with garden bed perfect for your morning coffee. A covered carport provides flexible use as parking or an outdoor dining and entertaining area. The sunny backyard is ideal for gardening and relaxing, offering plenty of space to enjoy the outdoors. The property also features a detached ADU built in 2016, providing approximately 640 square feet of additional living space. The ADU includes an open-concept living room and kitchen with vaulted ceilings, a one-bedroom ensuite, an interior laundry/mudroom, and a convenient half bath. An additional charming detached flex space offers versatile spot perfect for a home office, exercise room, art studio. This is a well-loved property, filled with wonderful memories, now ready for its next owner to add their personal touch. This is a perfect opportunity for owner to live in one and rent the other like the current owner did. It is a versatile property, offering multi-generational living, with a guest house, and has investment potential.

3 Beds ⋅ 4 Baths ⋅ 326020947 MLS

This is a must see. You will love this charming 1940s single-story cottage, located less than a mile from the vibrant Healdsburg Plaza. This inviting 2-bedroom, 2-bath home offers approximately 928 square feet of living space and has been thoughtfully updated over the years. Interior highlights include vaulted ceilings, a cozy fireplace, and an open-concept floor plan that creates a bright and welcoming atmosphere. Love the ivy covered front courtyard, private space with garden bed perfect for your morning coffee. A covered carport provides flexible use as parking or an outdoor dining and entertaining area. The sunny backyard is ideal for gardening and relaxing, offering plenty of space to enjoy the outdoors. The property also features a detached ADU built in 2016, providing approximately 640 square feet of additional living space. The ADU includes an open-concept living room and kitchen with vaulted ceilings, a one-bedroom ensuite, an interior laundry/mudroom, and a convenient half bath. An additional charming detached flex space offers versatile spot perfect for a home office, exercise room, art studio. This is a well-loved property, filled with wonderful memories, now ready for its next owner to add their personal touch. This is a perfect opportunity for owner to live in one and rent the other like the current owner did. It is a versatile property, offering multi-generational living, with a guest house, and has investment potential.

823 Prince Ave, Healdsburg

$1,037,500

"The Cottage Surrounded by the Redwoods" and other fantastic trees, gardens, and flowers would be the perfect name for this 2 bedroom 2 bathroom farmhouse. Walking distance from the Healdsburg square and Downtown Healdsburg, this single level home is ready for your personal touch, and could also qualify for your ADU/Guest House if you decided to build another home on this large almost acres flat usable lot. This ranch neighborhood has built its way up to a very prominent high end area. Don't miss out on this opportunity! Be sure to see the property video.

2 Beds ⋅ 2 Baths ⋅ 326052562 MLS

"The Cottage Surrounded by the Redwoods" and other fantastic trees, gardens, and flowers would be the perfect name for this 2 bedroom 2 bathroom farmhouse. Walking distance from the Healdsburg square and Downtown Healdsburg, this single level home is ready for your personal touch, and could also qualify for your ADU/Guest House if you decided to build another home on this large almost acres flat usable lot. This ranch neighborhood has built its way up to a very prominent high end area. Don't miss out on this opportunity! Be sure to see the property video.

451 W North St, Healdsburg

$1,030,000

Built circa 1870 in the Homestead Cottage style, this home features three bedrooms, one bath in the main section of house and a one bedroom, one bath attached guest addition in the rear of home. The extra large lot and floor plan of the home provides opportunities for expansion and modernization. The parcel slopes gently from Grant Street to the South creating privacy and a wonderful shaded rear yard with mature trees which include avocado and lemon trees. The location of this vintage home is ideal and a short distance to many of Healdsburg's best amenities.

4 Beds ⋅ 2 Baths ⋅ 326070618 MLS

Built circa 1870 in the Homestead Cottage style, this home features three bedrooms, one bath in the main section of house and a one bedroom, one bath attached guest addition in the rear of home. The extra large lot and floor plan of the home provides opportunities for expansion and modernization. The parcel slopes gently from Grant Street to the South creating privacy and a wonderful shaded rear yard with mature trees which include avocado and lemon trees. The location of this vintage home is ideal and a short distance to many of Healdsburg's best amenities.

216 Grant St, Healdsburg

$990,000

This charming Craftsman bungalow is conveniently located in town near everyday amenities. An inviting three bedroom, two bath single level home with hardwood floors, offering timeless character with built-ins and window seats, paired with an open floor plan and updated chef's kitchen. Recently remodeled bathroom with Restoration Hardware vanity, Carrara marble, and Lefroy Brooks plumbing fixtures. The thoughtfully designed outdoor space features low maintenance landscaping, fruit trees, raised garden beds with tomatoes, herbs, vegetables, and a beautifully designed stone fire pit for relaxed gatherings. With dual-pane Milgard windows, fresh interior paint, an electric car charging station, and newer roof, this beautifully updated home captures the essence of Healdsburg living.

3 Beds ⋅ 2 Baths ⋅ 326038692 MLS

This charming Craftsman bungalow is conveniently located in town near everyday amenities. An inviting three bedroom, two bath single level home with hardwood floors, offering timeless character with built-ins and window seats, paired with an open floor plan and updated chef's kitchen. Recently remodeled bathroom with Restoration Hardware vanity, Carrara marble, and Lefroy Brooks plumbing fixtures. The thoughtfully designed outdoor space features low maintenance landscaping, fruit trees, raised garden beds with tomatoes, herbs, vegetables, and a beautifully designed stone fire pit for relaxed gatherings. With dual-pane Milgard windows, fresh interior paint, an electric car charging station, and newer roof, this beautifully updated home captures the essence of Healdsburg living.

236 Powell Ave, Healdsburg