About The Property

18 Grayson Rd, Winchester is a meticulously maintained 3-bedroom colonial set in the sought-after Winchester Highlands neighborhood, just steps from Muraco Elementary and the Middlesex Fells. Built in 1931 and offering approximately 2,992 square feet of living space, this classic home blends timeless character with thoughtful, modern updates.

Inside 18 Grayson Rd, Winchester

Rich hardwood floors flow through the formal dining room into the oversized, fireplaced living room ideal for entertaining. The beautifully appointed kitchen features pendant lighting and a sunny breakfast area with access to a private deck. Upstairs, you’ll find two spacious bedrooms and a primary suite that boasts a walk-in closet and a stunning en-suite bath with a clawfoot tub.

From the driveway, enter a newly renovated, partially finished basement including a mudroom and ample flex space for an exercise room or media/play area. Recent updates include a new furnace, water heater, and an expanded, permeable-paver driveway accommodating up to four off-street parking spaces, plus a 1-car attached garage. Central air, insulated windows and doors, and a programmable thermostat help reduce annual energy costs.

Winchester Highlands Location & Schools

Families will appreciate Winchester’s top-rated schools — Muraco Elementary, McCall Middle School, and Winchester High School — while commuters enjoy easy highway access and public transportation. Situated on a level 0.16-acre lot, this Winchester home is steps from the Tri-Community bike path, hiking trails, Leonard Field, playgrounds, and tennis courts, with conservation areas and parks nearby.

Offered at $1,699,000, 18 Grayson Rd, Winchester is a rare opportunity to own a move-in-ready colonial in one of the area’s most desirable locations. Contact the Andersen Group Realty team to learn more, view the virtual tour, or schedule a private showing — and be sure to explore more homes for sale across Greater Boston.