Winchester Highlands Homes for Sale

Welcome to Winchester Highlands, a picturesque neighborhood nestled in the heart of Winchester, MA. Located in Middlesex County, Winchester is a charming town known for its historic charm, top-rated schools, and vibrant community spirit. Winchester Highlands offers the perfect blend of suburban tranquility and urban convenience, making it an ideal place to call home.

If you are looking for homes for sale in Winchester Highlands, you are in luck. The real estate market in this area is thriving, with a variety of housing options to suit every lifestyle. From cozy single-family homes with lush green yards to modern townhouses with all the latest amenities, there is something for everyone in Winchester Highlands.

Whether you are a first-time homebuyer looking to settle down or a growing family in need of more space, Winchester Highlands has it all. With tree-lined streets, well-maintained parks, and easy access to shopping and dining options, this neighborhood truly has something for everyone.

Don't miss your chance to be a part of this vibrant community. Explore the homes for sale in Winchester Highlands today and discover the perfect place to put down roots and create lasting memories.

Newest Winchester Highlands Homes for Sale

$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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