Winchester Highlands Homes with Colonial Style

Welcome to Winchester Highlands, a picturesque neighborhood nestled in the heart of Winchester, Massachusetts, within Middlesex County. Known for its charming streets and vibrant community spirit, this area offers a perfect blend of suburban tranquility and urban convenience. With its rich history and stunning natural landscapes, Winchester Highlands is an ideal place for families, professionals, and retirees alike.

The neighborhood boasts a variety of architectural styles, but it is particularly renowned for its beautiful Colonial-style homes. These timeless residences exude elegance and charm, featuring classic elements such as symmetrical facades, gabled roofs, and inviting front porches. Many of these homes are set on spacious lots, surrounded by lush greenery and mature trees, creating a serene environment that feels like a retreat from the hustle and bustle of city life.

In addition to their aesthetic appeal, Colonial homes in Winchester Highlands are designed with functionality in mind. Spacious floor plans, multiple bedrooms, and ample living areas make these homes perfect for entertaining guests or enjoying family time. Many properties also feature modern updates while preserving their historic character, offering the best of both worlds.

Living in Winchester Highlands means enjoying access to top-rated schools, vibrant local shops, and a strong sense of community. Residents can take advantage of nearby parks, recreational facilities, and a variety of outdoor activities, making it a great place to raise a family or enjoy a peaceful lifestyle.

Discover the charm of Winchester Highlands and the allure of its Colonial-style homes—where history meets modern living in one of Massachusetts' most sought-after neighborhoods.

Newest Winchester Highlands Homes with Colonial Style

$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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