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A rare offering in one of Winchester's most desirable neighborhoods, this spacious mid-century contemporary spans approximately 3,500 square feet with 5 bedrooms and 3.5 baths on a private 0.24-acre lot. The open main level flows from a light-filled living room with a cathedral ceiling, stained-glass accents, and a fireplace into the dining room, family room, and a renovated kitchen with Silestone quartz countertops, upgraded cabinetry, and direct deck access. Upstairs, two ensuite bedrooms anchor the floor plan, including a generous primary suite with a large jetted soaking tub, vanity, and walk-in closet. Three additional bedrooms and a family bath complete the level. Hardwood floors run throughout, a second fireplace warms the lower-level bonus room, and ductless mini-splits deliver year-round comfort throughout the house. The walk-out lower level offers a versatile bonus room with its own exterior entrance, ideal for a home office, gym, media room, playroom, or guest suite. Three decks extend the living space outdoors for entertaining and dining above the private backyard, and an attached two-car garage adds everyday ease. Set on a quiet street with easy access to commuter rail, downtown Winchester, parks, and bike or jog trails, this is a rare chance to live in your dream home in a community that has it all. $1,749,000 Active

17 Churchill Rd Winchester, Massachusetts

5 Beds 4 Baths 3,508 SqFt 0.24 Acres

An exceptional opportunity in one of Winchester’s most desirable neighborhoods, directly across from the Winchester Country Club. Set on a beautiful .39-acre lot, this distinctive 4-bedroom, 3.5-bath Colonial offers approximately 2,709 sq. ft. of living space, a 2-cargarage, generous room proportions, and a flexible floor plan ready for its next chapter. Offering wonderful possibilities with its generous proportions, flexible floor plan, and impressive setting, the property presents an ideal canvas for buyers looking to renovate and personalize a home to their exact vision. Reimagine the existing spaces with sophisticated modern finishes, create a timeless renovation that complements the home’s character, or explore the possibilities for a more extensive transformation. The spacious lot also provides plenty of room to enhance the outdoor experience with thoughtfully designed landscaping, gardens, patios, entertaining areas, or other outdoor amenities. Beyond the property itself, the location stands out, with the Winchester Country Club just across the street and downtown Winchester conveniently nearby, offering restaurants, cafés, shops, services, and commuter rail access to Boston. Convenient access to Winchester public schools, major routes, and nearby public transportation makes commuting and exploring the Greater Boston area easy. Bring your architect, contractor, and creativity and transform this property into something truly special. With its substantial lot, desirable neighborhood setting, proximity to downtown, and access to everything Winchester has to offer, 25 Arlington Street presents a rare chance to create a home that reflects your own style in an exceptional location. $1,529,000 Pending

25 Arlington St Winchester, Massachusetts

4 Beds 4 Baths 2,709 SqFt 0.39 Acres

Completely renovated and beautifully appointed, this exceptional two-level residence offers sophisticated, move-in-ready living in one of Winchester’s most convenient locations. Featuring 3 bedrooms, 3.5 baths, and a private one-car garage, this stylish home combines modern luxury, thoughtful updates, and everyday convenience. The stunning renovated kitchen features high-end stainless steel appliances, contemporary finishes, and a clean, modern aesthetic. The spacious two-level layout provides excellent separation between living and sleeping areas, creating a comfortable and versatile floor plan. Additional amenities include central AC, in-unit laundry, a security system, and the convenience of a private one-car garage. Ideally situated close to vibrant downtown Winchester, enjoy easy access to shops, restaurants, cafés, the commuter rail to Boston, and the beautiful hiking and recreation trails of the Middlesex Fells Reservation. A rare opportunity to enjoy a completely renovated, high-end residence with the space, amenities, and location that make Winchester living so desirable. $4,500 Active

5A Euclid Ave 5A Winchester, Massachusetts

3 Beds 4 Baths 1,520 SqFt

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