Set on a premier and picturesque tree-lined street in the highly coveted North of Montana neighborhood, this beautifully renovated one story home offers the perfect blend of classic character and modern upgrades. The residence is situated on one of the largest Gillette Regent Square lots available at 8,920 square feet with 60 feet of frontage. This stunning property features 2,614 square feet of living space with four bedrooms and two bathrooms, plus a one-bedroom, one-bathroom detached guest house, creating a flexible and inviting living environment. The formal entry reveals a bright and airy home with high ceilings, wood floors, center hall plan, and elegant French doors, all enhancing the home's charm. The living room and formal dining room feature large picture windows overlooking the newly landscaped front yard. The dining room's cove ceilings and the living room's custom built-ins, beamed ceilings, and striking fireplace are just a few of the home's carefully crafted architectural details. The gourmet kitchen boasts high-end stainless-steel appliances, custom cabinetry, ample counter space, bar seating, and French doors leading outside, perfect for both everyday cooking and large scale entertaining. The primary suite serves as a secluded retreat, complete with an en-suite bathroom featuring double sinks, an enclosed separate shower, and a soaking tub. Three additional bedrooms, all flooded with natural light from their gorgeous French doors, all lead outdoors and share a beautifully updated skylight-lit hallway bathroom. The detached guest house adds privacy and flexibility, featuring one bedroom, a great room, and a full bathroom, ideal for guests, a home office, or a future potential ADU conversion. The expansive backyard is a true outdoor oasis, complete with a large sport court, turf area, and a generous seating spot, creating the perfect setting for relaxation and entertaining. Additional highlights include brand-new electrical throughout, new cedar closets, a California basement for extra storage, a large driveway with an electric car charger, and brand-new front and backyard landscaping that enhances the home's appeal. Located in the Franklin Elementary School district and adjacent to Montana Avenue's vibrant boutique shopping and award winning dining, and moments from the Brentwood Country Mart, hiking, bike paths, bluffs and the beach, this is a rare opportunity to own a beautifully updated home in one of north Santa Monica's most sought-after neighborhoods.