Winchester Highlands, MA homes for sale & real estate

Winchester Highlands, MA Homes for Sale

Submerge yourself in historic elegance in this meticulously detailed Victorian home, brimming with classic design. Located on one of Winchester’s most serene and desirable cul-de-sacs, this stunning gem overflows with rich architectural details. Inside, you'll find three stately fireplaces, two oversized pocket doors, exquisite antique leaded light fixtures, stained glass, gleaming hardwood floors, soaring ceilings, and sun-drenched rooms with grand windows throughout. The unique layout features handsome fireplaces in both living and dining rooms, a charming updated kitchen, 2 en-suite bedrooms (another fireplace!), a private office, and laundry room. Enjoy a chat with a friend on the

Winchester Highlands, MA Homes for Sale

Opportunity to own the last available end unit! Welcome to 162 Swanton Street, the final new construction townhome by Ron Roy in the heart of Winchester. This home blends modern design with exceptional craftsmanship. The open-concept first floor features hardwood floors, a cozy fireplace, and a chef-inspired kitchen with stainless steel appliances, a large island, and adjacent mudroom with half bath. The second floor offers two spacious bedrooms and a full bath, while the third floor is a private primary suite with a spa-like en-suite. The finished lower level provides flexible space for a great room, office, or gym with its own full bath. Includes two off-street parking spaces with EV char

Winchester Highlands, MA Homes for Sale

Situated in this highly desirable quiet residential neighborhood sits this 4+ bedroom, 2 bathroom Colonial. This house is loaded with curb appeal from its white picket fence, wraparound porch, and mature plantings and trees. Upon entering this home, you are greeted by its gracious foyer. Off the foyer is a large living room that flows seamlessly into the family-size dining room. The kitchen is accessed from both the dining room and the foyer. The eat-in kitchen is updated and well-equipped. The first floor is completed with a nicely remodeled full bath. The second floor consists of 2 bedrooms, full bath, and oversized laundry room with large deck off of it with stairs leading to the backyar

Winchester Highlands, MA Homes for Sale

Step into timeless elegance with this Colonial Revival, a true celebration of classic architecture, refined style, and exceptional craftsmanship. From the moment you arrive, the home's rich character makes a striking first impression, setting the stage for everything that follows. Inside, you’ll discover a harmonious blend of historic charm and modern comfort. Gleaming hardwood floors, intricate leaded glass cabinetry, and exquisite moldings whisper stories of a bygone era. High ceilings and sunlit rooms create a sense of airy sophistication, while cozy window seats invite you to unwind. The gracious, flowing layout features 6 spacious bedrooms and 3.5 baths, w/ space for family, gues

Winchester Highlands, MA Homes for Sale

Stunning Seven-Year-Old Stoneham Home with Exceptional Parking. This meticulously rebuild seamlessly blends modern luxury with practical living. This residence offers 4 bedrooms and 4 full bathrooms, with the flexibility to create up to 6 bedrooms to accommodate your evolving needs. The heart of the home features a well-appointed kitchen that flows effortlessly into comfortable entertainment areas, perfect for both intimate gatherings and larger celebrations. The crown jewel is the impressive master suite, offering a private retreat with premium finishes and thoughtful design. Ideally situated near the highly-regarded South School, this property provides unparalleled convenience for commute

Winchester Highlands, MA Homes for Sale

Fantastic opportunity to own a freshly updated 2 bed 2 bath condo in Winchester—one of Massachusetts’ top-rated school districts. Located in the desirable Lynch Elementary district, which will open a brand-new school building this fall. This move-in ready home has just been freshly painted, with brand-new kitchen appliances and new carpeting throughout. The open-concept living and dining area connects to a private balcony facing the interior courtyard. The spacious primary suite features a walk-in closet and en-suite bath. A second bedroom and full bath provide flexibility for guests, family, or home office use. Additional highlights include in-unit laundry and two outdoor parki