Winchester Highlands Real Estate

Welcome to Winchester Highlands, a picturesque neighborhood nestled in the heart of Winchester, Massachusetts, within the charming Middlesex County. Known for its beautiful landscapes, rich history, and vibrant community spirit, Winchester Highlands is the perfect place to call home.

This serene neighborhood is characterized by its tree-lined streets, stunning colonial and contemporary homes, and a strong sense of community. Residents enjoy a tranquil suburban lifestyle, complemented by easy access to the bustling amenities of nearby Boston, just a short drive away. The area boasts excellent schools, making it an ideal choice for families seeking quality education and a nurturing environment for their children.

Winchester Highlands is not just about beautiful homes; it’s also about the lifestyle. Outdoor enthusiasts will appreciate the nearby parks and recreational facilities, including the scenic Winchester Town Common, where you can enjoy leisurely strolls, picnics, and community events throughout the year. For those who enjoy nature, the Middlesex Fells Reservation offers miles of hiking trails and stunning views, perfect for weekend adventures.

The local dining scene is a delightful mix of cozy cafes and upscale restaurants, providing a variety of culinary experiences to suit all tastes. Additionally, Winchester’s vibrant downtown area features charming boutiques and shops, ensuring that residents have everything they need right at their fingertips.

With a rich tapestry of culture, community, and convenience, Winchester Highlands is more than just a neighborhood; it’s a place where memories are made and dreams are realized. Come discover the charm of Winchester Highlands and see why so many choose to call this beautiful community home!

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.

Start Your Search

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.