Winchester Highlands Real Estate

Welcome to Winchester Highlands, a hidden gem nestled in the heart of Massachusetts’ Middlesex County. This charming neighborhood in the picturesque town of Winchester offers a perfect blend of suburban tranquility and vibrant community life, making it an ideal place for families, professionals, and retirees alike.

Winchester Highlands is renowned for its stunning landscapes, featuring tree-lined streets and beautifully maintained parks that invite outdoor activities year-round. The area is rich in history, with a quaint downtown that boasts a delightful mix of boutique shops, cozy cafes, and essential services. Residents enjoy the convenience of local amenities while being just a short drive or train ride away from the bustling city of Boston, making it easy to experience urban excitement without sacrificing the peace of suburban living.

Education is a cornerstone of the Winchester Highlands community, with top-rated schools serving students from kindergarten through high school. Families here take pride in their strong sense of community, often coming together for local events, farmers’ markets, and seasonal festivities that celebrate the unique character of the area.

For nature lovers, the nearby Middlesex Fells Reservation offers miles of hiking trails, scenic views, and opportunities for outdoor recreation, ensuring that residents can enjoy the beauty of nature right at their doorstep. Whether you’re looking to settle down in a charming single-family home or a modern condo, Winchester Highlands provides a welcoming atmosphere that feels like home.

Discover the warmth and charm of Winchester Highlands, where community spirit and natural beauty come together to create a truly exceptional living experience.

Newest Listings in Winchester Highlands

$974,900

4 Beds ⋅ 3 Baths ⋅ 73575764 MLS

Looking for a quiet retreat, with a SIDE STREET DRIVEWAY, built in privacy but still connected to the urban hustle and bustle of Boston metro? A rare Winchester opportunity, has arrived, priced comfortably 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, 2.5 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. Owners JUST put in an unused half bathroom on the first floor PERFECT for entertaining and preserving the privacy of your 2nd floor bathrooms. 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. Minutes from the iconic, and picturesque downtown Winchester where you'll find quaint coffee shops, local boutiques, and even a Commuter rail stop! Quick entry to Boston, Burlington, and the surrounding metro Boston area via nearby I95, Rt2, Rt3. Like spending your free time outdoors? You are mere minutes from the Medford Fells, one of Greater Boston's greenest and most resident friendly (humans and dogs alike) stretches of nature. Smaller upstairs bathroom could be converted to a 1/2 bath with stackable laundry or a dedicated laundry room (SEE ATTACHED RENDERINGS). Some of the previously prepared conceptual expansion plans are in the photos, the rest are available for review upon request.

258 Cross St, Winchester

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

$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.

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