Winchester Highlands Real Estate

Welcome to Winchester Highlands, a charming neighborhood nestled in the heart of Winchester, Massachusetts. Known for its picturesque landscapes and tight-knit community, this area offers a unique blend of suburban tranquility and urban convenience.

Winchester Highlands is characterized by its tree-lined streets, well-maintained homes, and beautiful parks, making it an ideal place for families and individuals seeking a serene environment. The neighborhood is conveniently located just 10 miles north of downtown Boston, providing easy access to the city’s vibrant cultural scene, dining, and employment opportunities. Commuters will appreciate the nearby MBTA train station, which offers a quick and efficient route to the city.

The community is served by the highly regarded Winchester Public Schools, known for their commitment to academic excellence and a range of extracurricular activities. Families will find plenty of recreational options, including the scenic Wright-Locke Farm, where you can enjoy fresh produce and community events, as well as the beautiful Horn Pond, perfect for leisurely walks and outdoor activities.

Winchester Highlands is not just a place to live; it’s a community where neighbors become friends. Local cafes, boutiques, and family-owned restaurants create a warm, inviting atmosphere that encourages community engagement. Whether you’re taking a stroll through the charming streets or enjoying a weekend at one of the local parks, you’ll quickly fall in love with the character and charm that Winchester Highlands has to offer. Come explore this hidden gem and discover your new home in this vibrant community!

Newest Listings in Winchester Highlands

$2,400,000

5 Beds ⋅ 3 Baths ⋅ 73544924 MLS

Welcome to 9 Plymouth Rd — a classic 1959 single-family home tucked at the end of a private road on a dead-end street, set on a private 0.52-acre lot abutting conservation land in one of Winchester's most sought-after neighborhoods. This well-appointed 11-room residence offers 5 bedrooms, 3 full baths, and 1 half bath, giving your family room to spread out and settle in. Thoughtfully updated for year-round comfort, the home features central AC, central humidification, and an air exchanger. Outside, enjoy beautifully landscaped gardens, a spacious deck overlooking the private yard, lush irrigated grounds with an invisible dog fence, and a hot tub for unwinding after a long day. A wood-burning fireplace adds warmth and character to the living space. Located just minutes from top-rated schools, Winchester Center, and convenient commuter access to Boston, this is a rare opportunity to enjoy privacy, nature, and timeless New England living in an exceptional location.

9 Plymouth Rd, Winchester

Listing courtesy of Listing Agent: Steph Crawford Group from Listing Office: Real Broker MA, LLC.

$999,900

4 Beds ⋅ 2 Baths ⋅ 73541288 MLS

A rare Winchester opportunity under $1M, 258 Cross Street blends timeless character, meaningful updates, everyday function, and exciting long-term upside. Set on a level, fenced corner lot, this 4 bed, 2 bath Colonial offers the space buyers need today with the flexibility to evolve over time. Inside - hardwood floors, crown molding, arched openings, bay windows, and detailed trim add warmth, while the updated kitchen features stone counters, upgraded cabinetry, stainless appliances, gas cooking, and great natural light. Both full baths have been tastefully updated, including a larger bath with double vanity, tiled shower, and soaking tub. Four bedrooms on the upper levels create options for guests, office, fitness, hobbies, or future needs. Brand new AC, central heat, full basement with laundry/storage, patio, fenced yard, shed, and 4-car parking add real utility. Previously prepared conceptual expansion plans are available for review. Minutes from the iconic, and picturesque downtown. Rear vestibule is the perfect place for a 1st floor half bath (see attached rendering). Smaller upstairs bathroom could be converted to a 1/2 bath with stackable laundry or a dedicated laundry room (SEE ATTACHED RENDERINGS).

258 Cross Street, Winchester

Listing courtesy of Listing Agent: Justin Blankenship from Listing Office: Fiv Realty Co.

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