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$1,199,000

Discover a rare dual-residence opportunity perfectly blending mountain serenity with everyday convenience nestled at the border of Scotts Valley & Los Gatos in the coveted Santa Cruz Mountains, This unique property features two fully independent homes surrounded by tranquil wooded views, open pastures & a seasonal creek. 4399 Glenwood Dr is a meticulously maintained & updated 3BR/2BA sanctuary offering +-1400 SF of warm living space. The home sits within a fully fenced, private oasis combining peaceful seclusion with effortless access to Highway 17, Santa Cruz beaches & Silicon Valley employment hubs. 4401 Glenwood Dr is tucked privately behind the main house on it's own private right of way. This updated 1BR/1BA, +-530 SF home serves as an ideal source for rental income, multi-generational living, or guest accommodations. While the residences share a private well & whole-house backup generator, they provide complete independence with separate parcels, individual septic systems, & dedicated PG&E meters. Enjoy this versatile property that seamlessly balances premium lifestyle, a prime commuter location, & long-term income potential.

4 Beds ⋅ ML82054170 MLS

Discover a rare dual-residence opportunity perfectly blending mountain serenity with everyday convenience nestled at the border of Scotts Valley & Los Gatos in the coveted Santa Cruz Mountains, This unique property features two fully independent homes surrounded by tranquil wooded views, open pastures & a seasonal creek. 4399 Glenwood Dr is a meticulously maintained & updated 3BR/2BA sanctuary offering +-1400 SF of warm living space. The home sits within a fully fenced, private oasis combining peaceful seclusion with effortless access to Highway 17, Santa Cruz beaches & Silicon Valley employment hubs. 4401 Glenwood Dr is tucked privately behind the main house on it's own private right of way. This updated 1BR/1BA, +-530 SF home serves as an ideal source for rental income, multi-generational living, or guest accommodations. While the residences share a private well & whole-house backup generator, they provide complete independence with separate parcels, individual septic systems, & dedicated PG&E meters. Enjoy this versatile property that seamlessly balances premium lifestyle, a prime commuter location, & long-term income potential.

4399 Glenwood DR, Scotts Valley

Listed by Lisa Dailey-goodrich, 831-325-6320 from Miritz & Bailey Real Estate, Inc
(If provided) CoList: from

$1,199,000

TWO HOUSES! Discover a rare dual-residence opportunity perfectly blending mountain serenity with everyday convenience nestled at the border of Scotts Valley & Los Gatos in the coveted Santa Cruz Mountains, This unique property features two fully independent homes surrounded by tranquil wooded views, open pastures & a seasonal creek. 4399 Glenwood Dr is a meticulously maintained & updated 3BR/2BA sanctuary offering +-1400 SF of warm living space. The home sits within a fully fenced, private oasis combining peaceful seclusion with effortless access to Highway 17, Santa Cruz beaches & Silicon Valley employment hubs. 4401 Glenwood Dr is tucked privately behind the main house on it's own private right of way. This updated 1BR/1BA, +-530 SF home serves as an ideal source for rental income, multi-generational living, or guest accommodations. While the residences share a private well & whole-house backup generator, they provide complete independence with separate parcels, individual septic systems, & dedicated PG&E meters. Enjoy this versatile property that seamlessly balances premium lifestyle, a prime commuter location, & long-term income potential.

3 Beds ⋅ 2 Baths ⋅ ML82053482 MLS

TWO HOUSES! Discover a rare dual-residence opportunity perfectly blending mountain serenity with everyday convenience nestled at the border of Scotts Valley & Los Gatos in the coveted Santa Cruz Mountains, This unique property features two fully independent homes surrounded by tranquil wooded views, open pastures & a seasonal creek. 4399 Glenwood Dr is a meticulously maintained & updated 3BR/2BA sanctuary offering +-1400 SF of warm living space. The home sits within a fully fenced, private oasis combining peaceful seclusion with effortless access to Highway 17, Santa Cruz beaches & Silicon Valley employment hubs. 4401 Glenwood Dr is tucked privately behind the main house on it's own private right of way. This updated 1BR/1BA, +-530 SF home serves as an ideal source for rental income, multi-generational living, or guest accommodations. While the residences share a private well & whole-house backup generator, they provide complete independence with separate parcels, individual septic systems, & dedicated PG&E meters. Enjoy this versatile property that seamlessly balances premium lifestyle, a prime commuter location, & long-term income potential.

4399 Glenwood DR, Scotts Valley

Listed by Lisa Dailey-goodrich, 831-325-6320 from Miritz & Bailey Real Estate, Inc
(If provided) CoList: from

$1,650,000

Tucked away from Vine Hill Road in the Happy Valley School District, this Santa Cruz retreat feels like a private world of its own. Set on 3.5+ park-like acres with gardens, winding paths, towering redwoods, and a seasonal creek with sandy beach area, the property offers privacy, natural beauty, and architectural character just minutes from town. The custom home brings the outdoors in, with dramatic windows, multiple decks, and serene views of the gardens and forest. A two-story atrium creates a striking first impression, while the generous floor plan offers space to gather, relax, work from home, or enjoy the peaceful setting. Distinctive living areas, including a sunroom, lounge spaces, and an upstairs wing, give the home flexibility and personality rarely found in a typical Santa Cruz property. The grounds are a true highlight, with lush landscapes, quiet corners, and open areas that feel like a private botanical retreat. Close to DeLaveaga Park trails, downtown Santa Cruz, beaches, commute routes, and everyday conveniences, this home offers the best of Happy Valley living: privacy, space, nature, and access to everything that makes Santa Cruz special. A rare opportunity to own a magical creekside property with room to breathe, explore, and create your own private sanctuary.

5 Beds ⋅ 3 Baths ⋅ ML82046835 MLS

Tucked away from Vine Hill Road in the Happy Valley School District, this Santa Cruz retreat feels like a private world of its own. Set on 3.5+ park-like acres with gardens, winding paths, towering redwoods, and a seasonal creek with sandy beach area, the property offers privacy, natural beauty, and architectural character just minutes from town. The custom home brings the outdoors in, with dramatic windows, multiple decks, and serene views of the gardens and forest. A two-story atrium creates a striking first impression, while the generous floor plan offers space to gather, relax, work from home, or enjoy the peaceful setting. Distinctive living areas, including a sunroom, lounge spaces, and an upstairs wing, give the home flexibility and personality rarely found in a typical Santa Cruz property. The grounds are a true highlight, with lush landscapes, quiet corners, and open areas that feel like a private botanical retreat. Close to DeLaveaga Park trails, downtown Santa Cruz, beaches, commute routes, and everyday conveniences, this home offers the best of Happy Valley living: privacy, space, nature, and access to everything that makes Santa Cruz special. A rare opportunity to own a magical creekside property with room to breathe, explore, and create your own private sanctuary.

450 Vine Hill RD, Santa Cruz

Listed by Seb Frey, 408-596-1623 from Compass
(If provided) CoList: from

$6,495,000

Nestled in a meadow & surrounded by over 21 acres of natural beauty, this magnificent gated Tuscan-inspired estate includes 1.5 acres of Pinot Noir grapes, offering a unique opportunity to own a private vineyard just 10 minutes from both Santa Cruz & Hwy 17 for easy access to Silicon Valley. At the heart of the single-level home lies a charming gated interior courtyard adorned with fruit trees, an outdoor fireplace, & a welcoming guest suite. The homes open layout, with abundant windows & French doors, invites seamless indoor-outdoor living. The spacious great room flows effortlessly into a chefs kitchen with other spaces including a formal dining room, family room & a pass-through bar opening to a built-in BBQ center beside the resort-style pool. The expansive grounds offer a bocce court, greenhouse, raised garden beds, a custom playground, a two-story treehouse with suspension bridge, pool & spa with designated bath, & multiple outdoor dining & lounge spaces. For automotive enthusiasts, an attached 4-car garage pairs with a separate 2-story barn/workshop featuring a car lift and room to accommodate up to 7 additional vehicles. The garage barn sits on an elevated section of the property, offering panoramic views & additional usable land.

5 Beds ⋅ 6 Baths ⋅ ML82039956 MLS

Nestled in a meadow & surrounded by over 21 acres of natural beauty, this magnificent gated Tuscan-inspired estate includes 1.5 acres of Pinot Noir grapes, offering a unique opportunity to own a private vineyard just 10 minutes from both Santa Cruz & Hwy 17 for easy access to Silicon Valley. At the heart of the single-level home lies a charming gated interior courtyard adorned with fruit trees, an outdoor fireplace, & a welcoming guest suite. The homes open layout, with abundant windows & French doors, invites seamless indoor-outdoor living. The spacious great room flows effortlessly into a chefs kitchen with other spaces including a formal dining room, family room & a pass-through bar opening to a built-in BBQ center beside the resort-style pool. The expansive grounds offer a bocce court, greenhouse, raised garden beds, a custom playground, a two-story treehouse with suspension bridge, pool & spa with designated bath, & multiple outdoor dining & lounge spaces. For automotive enthusiasts, an attached 4-car garage pairs with a separate 2-story barn/workshop featuring a car lift and room to accommodate up to 7 additional vehicles. The garage barn sits on an elevated section of the property, offering panoramic views & additional usable land.

220 Falcon HL, Santa Cruz

Listed by Lyng-Vidrine Team, 831-345-0503 from David Lyng Real Estate
(If provided) CoList: Dennis Lunder from Dennis A. Lunder, Broker