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

$2,225,000

4 Beds ⋅ 4 Baths ⋅ 73554545 MLS

Rarely available in one of Winchester’s most desirable neighborhoods, this beautifully maintained Colonial offers the perfect blend of modern comfort and convenience. Set on a quiet cul-de-sac surrounded by historic homes, this late 1990s residence provides newer construction, a thoughtfully designed floor plan and an exceptional location just minutes from Winchester Center, commuter rail, Lincoln Elementary School and the Middlesex Fells Reservation with miles of trails, hiking, running and The Sheepfold dog park. The traditional yet open layout features an updated kitchen, spacious living and dining areas, refreshed baths, fresh paint and updated mechanical systems. A versatile bonus room with a private staircase offers endless possibilities as a home office, media room, guest space, playroom or fitness area. The finished lower level with half bath adds valuable living space. Enjoy outdoor living on the wraparound deck overlooking a private backyard with mature landscaping.

6 Davey Ln, Winchester

Listing courtesy of Listing Agent: Gretchen Papineau from Listing Office: Coldwell Banker Realty - Andovers/Readings Regional.

$2,500,000

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

258 Cross Street, Winchester

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

$1,675,000

5 Beds ⋅ 4 Baths ⋅ 73538393 MLS

Excellent New Price! Classic curb appeal abounds at this expansive five-bedroom colonial in the desirable Winchester Highlands neighborhood. The sun-filled first floor features a gracious floor plan with a thoughtfully designed eat-in kitchen showcasing premium appliances including a Sub-Zero refrigerator and Fisher & Paykel DishDrawer. A dining room, living room with wood-burning fireplace, office, mudroom and powder room complete this level. Upstairs, the generous primary suite includes full bath and convenient laundry and is complemented by four additional bedrooms and a family bath. A walk-up attic provides flexible bonus space and storage, while the finished lower level offers a spacious family room, bonus room, and kitchenette with ADU potential. Enjoy the private backyard retreat complete with a fully fenced yard and pristine in-ground pool, plus two-car attached garage. An extraordinary opportunity to enjoy space, comfort, and refined living in one of Winchester’s most sought-after neighborhoods, a short stroll to the incredible nature at the Fells Reservation.

117 Highland Ave, Winchester

Listing courtesy of Listing Agent: Dara Singleton from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.

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