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10040 Highway 9, Ben Lomond
$2,399,000
13 Beds ⋅ ML82064484 MLS ⋅ Windsor Woods BLDG.
Nestled among the towering redwoods of the San Lorenzo Valley, this 8-unit multifamily property has excellent rental history with low vacancy, appealing to long-term tenants, and offers the fundamentals a thoughtful investor looks for: high occupancy, high income potential, and a desirable location for easy access to highways and public transportation. Versatility of units makes this great for buyers searching for solid investment return: live in one, rent the others, or a community compound. Property has been well-maintained by the current owner. Set on a bright and sunny flat lot with one new roof, repairs, and painting completed in 2026. The property features a mix of 1- and 2-bed cottages, two 2-bed apartments, 3 studio apartments, and a 3-bed/2-bath house, with inviting front porches, vibrant exterior finishes, and a peaceful, community-oriented layout that tenants love, with the opportunity to create a large raised-bed garden. Additional highlights include on-site parking for all units and a large garage for storage and extra income potential. With the flexible unit mix and upside potential, this is an exceptional opportunity for investors seeking immediate cash flow and long-term appreciation in one of the most desirable and supply-constrained rental markets in CA.

10040 Highway 9, Ben Lomond

Listed by Sage Goncharoff, 831-440-7876 from Action Properties Inc
(If provided) CoList: from

1160 Dundee AVE, Ben Lomond
$649,000
2 Beds ⋅ 1 Baths ⋅ ML82058773 MLS
Welcome to sunrise cottage, this beautifully remodeled 2 bed, 1 bath home blends modern comfort with timeless mountain charm. Thoughtfully updated with no expense spared, the inviting interior features a stylish Waypoint kitchen with quartzite countertops, butcher block island, stainless steel appliances, and an open-concept living and dining area complete with custom built-in cabinetry, and premium wood burning fireplace insert. The updated bathroom includes a stackable washer/ dryer, while the split-bedroom layout provides separation of space. Outside, the property offers exceptional parking for up to 5 vehicles on a freshly paved driveway. Two spacious storage sheds offers ample room for hobbies and gear, one of which offers built in workshop tools. The durable TimberTech wraparound deck and outdoor pizza oven create the perfect setting for relaxing or entertaining beneath the redwoods. Convenient features like the Tesla powerwall backup battery, dual pane windows, included backup generator, and the option to buy this home fully furnished make it a unique and resilient offering. Ideally located up the hill from hwy 9 but without the traffic noise. Enjoy nearby Highlands Park, San Lorenzo River swimming holes, scenic hiking trails, and local restaurants/ shopping.

1160 Dundee AVE, Ben Lomond

Listed by Peter Eubank, 831-471-7330 from Room Real Estate
(If provided) CoList: from

355 Waldeberg RD, Ben Lomond
$849,000
4 Beds ⋅ 3 Baths ⋅ ML82062285 MLS
Welcome to a truly special home nestled among majestic redwoods, where nature and tranquility surround you. Set in a peaceful, wooded setting with the sound of a creek flowing in the distance. This is more than a home, it is a peaceful sanctuary where you can slow down an connect with nature. Wake up to the soothing sounds of flowing water, towering trees and abundant natural beauty right outside your door. The property provides a wonderful connection to nature while still offering a comfortable, cozy place to call home. Open floor plan, Soaring ceilings, skylights and hardwood floors. Extensive decking expands the living space. sparkling Jacuzzi lap pool is the ultimate place to unwind. Plenty of room to garden & hike trails to Marshall creek. Close to the peaceful town of Ben Lomond. Everyday feels like a getaway.

355 Waldeberg RD, Ben Lomond

Listed by Rhonda Prunella, 408-334-8542 from CENTURY 21 Masters
(If provided) CoList: from

8455 Highway 9, Ben Lomond
$749,000
2 Beds ⋅ 2 Baths ⋅ ML82057041 MLS
Redwood Retreat with easy access! This lovely 2 bedroom, 2 bath home across from the entrance to Highlands Park, set back from Hwy 9 behind a large turnout and a protective wall of redwoods. Surrounded by decks and gardens, the home captures sunlight filtering through the trees at every time of day, creating a private, enchanting setting. Inside, dark hardwood floors and gas fireplace anchor the living room. The kitchen features granite countertops, stainless steel appliances, slate tile flooring, plus an island offering additional counter space and bar seating. Kitchen opens to the living area & generous dining room, perfect for entertaining, storage, etc The spacious primary suite with high vaulted open beam ceilings, large closet, and access to the upper decks. A large bathroom featuring double sinks, granite counters and a newly remodeled shower. Views of the park and redwoods from both bedroom windows. 2nd bedroom is also large with a generous closet, vaulted ceilings and views of the trees. Double French doors access upper decks and bring light. New retaining walls throughout the property, newer roof and gutters in Dec 2024. A covered carport plus extra parking and additional storage area. This home is a lovely retreat very close to schools, parks, Felton & Ben Lomond!

8455 Highway 9, Ben Lomond

Listed by Carie Sigur, 831-359-3190 from Vista Properties Inc
(If provided) CoList: from

10040 Highway 9, Ben Lomond
$2,399,000
ML82055141 MLS ⋅ Windsor Woods BLDG.
Nestled among the towering redwoods of the San Lorenzo Valley, this 8-unit multifamily property has excellent rental history with low vacancy, appealing to long-term tenants, and offers the fundamentals a thoughtful investor looks for: high occupancy, high income potential, and a desirable location for easy access to highways and public transportation. Versatility of units makes this great for buyers searching for solid investment return: live in one, rent the others, or a community compound. Property has been well-maintained by the current owner. Set on a bright and sunny flat lot with one new roof, repairs, and painting completed in 2026. The property features a mix of 1- and 2-bed cottages, two 2-bed apartments, 3 studio apartments, and a 3-bed/2-bath house, with inviting front porches, vibrant exterior finishes, and a peaceful, community-oriented layout that tenants love, with the opportunity to create a large raised-bed garden. Additional highlights include on-site parking for all units and a large garage for storage and extra income potential. With the flexible unit mix and upside potential, this is an exceptional opportunity for investors seeking immediate cash flow and long-term appreciation in one of the most desirable and supply-constrained rental markets in CA.

10040 Highway 9, Ben Lomond

Listed by Sage Goncharoff, 831-440-7876 from Action Properties Inc
(If provided) CoList: from

110 Azalea WAY, Ben Lomond
$749,000
3 Beds ⋅ 1 Baths ⋅ ML82053242 MLS
Nestled beneath a majestic canopy of towering redwoods at the end of a peaceful private lane, this enchanting retreat is a place where nature & home exist in perfect harmony. Warm, inviting interiors unfold through an open-concept design filled w/ natural light. Beautifully updated kitchen w/ stainless steel appliances flows effortlessly into the heart of the home. Ideal setting for both quiet mornings & effortless entertaining.Upstairs, 3 spacious bdrms offer peaceful retreats complemented by a full bath. Beautiful private backyard with a generous patio, invites al fresco dining, morning coffee, or evenings spent beneath the trees. A storage shed provides added convenience. Multiple end of street parking spaces including a dedicated off-street parking space by the home ensures plenty of room for family & guests alike.Thoughtfully appointed w/ bamboo flooring, dual-pane windows, & tranquil woodland views from nearly every room, the home offers a rare sense of serenity while remaining just moments from downtown Ben Lomond, scenic hiking trails, & easy commute to Silicon Valley.Whether you're searching for a full-time residence or a peaceful mountain escape, this is an opportunity to embrace the timeless beauty and relaxed lifestyle of the Santa Cruz Mountains.

110 Azalea WAY, Ben Lomond

Listed by Marisa Irene Thompson, 408-761-0609 from Golden Gate Sotheby's International Realty
(If provided) CoList: from

595 Wente ST, Ben Lomond
$2,385,000
4 Beds ⋅ 6 Baths ⋅ ML82052088 MLS
Tucked away on a quiet, low-traffic lane, this meticulously maintained single-level estate offers luxury living on 1.4 level acres with equestrian amenities, a detached ADU, and an expansive workshop/garage. All within walking distance of restaurants, coffee shops, grocery shopping, and everyday conveniences. The thoughtfully designed home features acacia wood floors, vaulted ceilings, walls of windows, a gas fireplace, built-in entertainment center, and a chefs kitchen with a custom cherry wood island, granite countertops, premium Miele appliances, walk-in pantry, appliance garage, and abundant custom storage. An attached 2 car garage, plus an office with separate entrance. The resort-style grounds include a sparkling pool, spa, lush gardens, mature fruit trees, raised beds, pasture, barn with stable, and fully fenced acreage. Entertain year-round beneath a custom gazebo with integrated lighting, outdoor kitchen, gas BBQ, smoker, and a stunning gas fireplace with a wood-fired pizza oven handcrafted by renowned local mason. The detached ADU offers abundant natural light, a gas fireplace, and separate driveway entrance. The enormous workshop/garage provides ideal space for creative pursuits, or a home-based business. A rare blend of privacy, convenience, & luxury living.

595 Wente ST, Ben Lomond

Listed by Teresa Marlow, 831-818-3430 from Compass
(If provided) CoList: from

board logoThe data relating to real estate for sale on this display comes in part from the Internet Data Exchange program of the MLSListingsTM MLS system. Real estate listings held by brokerage firms other than Bailey Properties are marked with the Internet Data Exchange and detailed information about them includes the names of the listing brokers and listing agents.
Based on information from MLSListings MLS as of . All data, including all measurements and calculations of area, is obtained from various sources and has not been, and will not be, verified by broker or MLS. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.


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