Winchester Highlands, MA homes for sale & real estate

Winchester Highlands, MA Homes for Sale

Charming townhouse located at The Village, one of Winchester’s most sought-after and impeccably maintained communities, offers 1,843sf of living space. Featuring 3 generously sized bedrooms with full-height ceilings, and 2.5 updated bathrooms, it is one of the largest homes in the community. The home is flooded with natural light thanks to its end-unit position, windows on three sides, and a skylight in the dining area. The freshly painted interior is complemented by refinished hardwood parquet floors, new carpeting in two of the bedrooms, and wood flooring in the third bedroom. The expansive living room is anchored by a wood-burning fireplace, while the open-concept kitchen and dinin

Winchester Highlands, MA Homes for Sale

Bathed in natural light and brimming with timeless charm, this 3-bedroom, 1-bath home is perfectly situated on a quiet dead-end street. The seamlessly flowing floor plan creates a warm, welcoming atmosphere, highlighted by beautifully refinished hardwood floors throughout. The exquisitely remodeled kitchen showcases sophisticated shaker cabinetry, rich quartz countertops, stainless steel appliances, and recessed lighting—perfect for everyday living. Enjoy two spacious, window-lined porches, freshly painted with new vinyl flooring, offering sun-soaked spaces year-round. The oversized detached garage with electricity makes an excellent workshop and also holds potential for conversion in

Winchester Highlands, MA Homes for Sale

This isn’t just a house — it’s a front-row seat to the good life, where you can walk to shops, schools, cafés, restaurants, and everything the town has to offer! This 5-bedroom, 3.5-bath Victorian sits proudly in the heart of Winchester Center, in the highly coveted Lincoln School district. Original hardwood floors, soaring ceilings, and stunning architectural details give this home its timeless character, while the updated kitchen and spacious rooms bring modern comfort to everyday living. With its gorgeous design and generous layout, it’s perfect for hosting friends or enjoying quiet evenings at home. And the best part? The backyard offers a quiet space with

Winchester Highlands, MA Homes for Sale

Welcome to your next chapter in this beautifully maintained multi-level home blending comfort, style, and convenience. Step into the sun-filled kitchen and dining area, where vaulted ceilings, skylights, cherry cabinetry, granite counters, and a large island create a warm gathering space. From here, open the slider to a sprawling two-tier deck, perfect for entertaining or relaxing outdoors. The dining room overlooks a spacious living room with a traditional brick fireplace, built-in speakers, and an additional seating nook for cozy evenings. The main level also features a private primary suite with a full bath, wet bar, and direct deck access, creating your own retreat. Upstairs, you’

Winchester Highlands, MA Homes for Sale

This 2024 construction offers single-level living with 2 bedrooms + flex room. The open-concept layout creates an airy, contemporary atmosphere. The bonus flex room/den adapts effortlessly to your needs. The stylish white kitchen showcases shaker cabinets with ample storage & a center island and flows seamlessly into the dining/living areas for dinner conversations. Enjoy your private outdoor space in your enclosed patio accessible off of the living room. The primary suite impresses with a huge walk in custom closet & a luxurious en-suite bath with double vanity. The second bed is spacious and bright. The one-car garage also has additional storage space, while elevator access &

Winchester Highlands, MA Homes for Sale

On the Winchester line! This custom-built 2014 home offers nine-foot ceilings and an open, spacious layout. A grand entryway leads to a formal dining room and an oversized chef’s kitchen with granite island, repurposed oak table extension, prep sink, high-end appliances, wine refrigerator, and pantry. The kitchen flows seamlessly into a fireplaced family room with built-in media storage and a sun-filled three-season room. The first-floor primary suite includes a walk-in closet or office and ensuite bath, while a second primary suite features a spa bath with sauna and direct access to a private deck. An additional ensuite bedroom plus two more generous bedrooms provide comfort for all.