Winchester Highlands Homes for Sale

Welcome to Winchester Highlands, a picturesque gem nestled in the heart of Middlesex County, Massachusetts. This charming neighborhood, part of the vibrant town of Winchester, offers a delightful blend of suburban tranquility and urban convenience. Known for its lush landscapes and friendly community, Winchester Highlands is the perfect place for families, professionals, and retirees alike to call home.

The region boasts a rich history, with beautifully preserved architecture that reflects its New England roots. Residents enjoy access to top-rated schools, making it an ideal location for families seeking a nurturing environment for their children. The area is also known for its abundance of parks and recreational facilities, providing ample opportunities for outdoor activities, from hiking and biking to picnicking in the sun.

When it comes to homes for sale in Winchester Highlands, you’ll find a diverse array of properties that cater to various tastes and budgets. Whether you’re looking for a charming colonial home with classic features, a modern townhouse with contemporary amenities, or a spacious single-family residence, the options are plentiful. Many homes boast expansive yards, perfect for entertaining or enjoying a quiet evening under the stars.

With its close-knit community atmosphere, excellent schools, and convenient access to Boston via the nearby commuter rail, Winchester Highlands truly offers the best of both worlds. Discover your dream home in this enchanting neighborhood and experience the vibrant lifestyle that awaits you in Winchester, MA. Your perfect home is just a showing away!

Newest Winchester Highlands Homes for Sale

$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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