Winchester MA Homes for Sale & Real Estate

Home for Sale in Winchester

This extraordinary, fully renovated home blends rich architectural detail w/ modern luxury in one of Winchester?s most sought-after neighborhoods. Designed by a shipbuilder, this home offers 5,876 sq ft of elegant living space filled w/ natural light, coffered ceilings, crown moldings, restored hardwood floors & more. The breathtaking chef?s kitchen includes a quartzite island, 8-burner Wolf range, paneled appliances, & wine bar. The first floor features generously sized rooms that flow beautifully, offering grand entertaining spaces, 4 fireplaces, & a statement staircase. Upstairs offers 4 bedrooms & 3 updated baths, including a serene primary suite w/ fireplace, marble bath & double closets. The third floor includes 2 add'l. beds, full bath, & room for expansion. Enjoy a private fenced yard w/ lush gardens, patio, & a 2+ car garage. With timeless character and thoughtful updates throughout, this is a rare opportunity just moments from town, train, and top schools!

Home for Sale in Winchester

Luscious landscaping and a beautiful farmers porch create amazing curb appeal for this classic colonial in the coveted Muraco School district. Offering a lovely floorplan which offers a welcoming foyer which allows access into the front living room, formal dining room and directly into a large kitchen with plenty of cabinets and granite countertops. The second level features a full bath as well as 3 sunlit bedrooms which include a primary bedroom with private ensuite bath. The walk up third floor is appointed with 2 additional bedrooms and ample storage space. Additional highlights include central air, storage shed, sprinkler system and fully fenced in yard. The home sits with convenient access to major highways, Winchester center and the commuter rail.

Home for Sale in Winchester

Located in a beautiful neighborhood, this thoughtfully renovated 3-bed, 2-bath home with a custom built free standing office/cottage/gym/ movie house, blends timeless charm w/ modern comfort. Sunlight pours into the open living spaces, highlighting original details & gleaming refinished hardwood floors. The inviting living room features a cozy fireplace w/ built ins, the dining room is perfect for gatherings. A bright family room boasts vaulted ceilings & skylights, creating an airy, welcoming atmosphere. Central AC ensures year-round comfort. Outside, the custom-built cottage offers a space for everybody with tall ceilings, custom cabinetry & window seat, AC/ heat, a spacious king-size loft & ethernet connection--ideal as a home office, gym, or studio. Many thoughtful upgrades have been made to this picturesque home. Enjoy the level, fenced-in yard, perfect for entertaining, gardening, or play. Close to downtown Winchester, schools, The Fells, Leonard field & new playground!

Home for Sale in Winchester

An extremely rare new construction in the Flats, this stunning 6BD/4.5BA home is a ground-up rebuild blending modern luxury with timeless warmth in one of Winchester?s most coveted neighborhoods. Designed for elevated living, it features a chef?s kitchen with quartz counters, custom cabinetry, a large island, and built-in bar, opening to a sunlit dining area ideal for both casual meals and elegant entertaining. The soaring family room stuns with cathedral ceilings, exposed beams, and a floor-to-ceiling stone fireplace?perfect for cozy evenings or lively gatherings. The serene primary suite offers a wood-accented ceiling, sitting area, and spa bath with dual vanities and a walk-in shower. Wide-plank oak floors, curated finishes, and thoughtful design details enrich every corner of the home. Located just moments from Winchester Center, commuter rail, top-rated schools, and scenic parks, this is a once-in-a-generation opportunity to own a truly exceptional home in the heart of the Flats.

Home for Sale in Winchester

Enjoy the best of Winchester living in this spacious 2-bed, 1.5-bath townhouse at Wedge Pond Condominium, set along scenic Wedge Pond. The main level features hardwood floors, a sunny living room, dining room with charming bow window, half bath, and renovated kitchen with updated appliances. Upstairs offers two bedrooms and a full bath. The finished lower level provides flexible space for a family room, home office, or guest bedroom, plus laundry and storage. Large closets throughout offer ample storage. Extend your living outdoors with garden views and a serene pondside setting. One deeded parking space included. Unbeatable location?walk to downtown shops, Packer Tennis Courts, new Lynch School, McCall, WHS, commuter rail, and Tri-Community Bike Path. Easy access to 95 and 93. A great fit for a variety of lifestyles, low-maintenance home, offering comfort, flexibility, and a prime location.

Home for Sale in Winchester

This sun-filled 2012 townhouse, with its spacious layout, backyard oasis & attached garage, lives like a single-family home. Spend weekends lounging on the private deck, unwinding under the pergola, or playing on the lush, fenced lawn. Inside, the inviting open layout is made for gathering?whether around the gas fireplace on cozy evenings or at the kitchen island while entertaining friends. High ceilings & hardwood floors create an airy, elegant feel, while the porch & backyard invite connection to the outdoors. Retreat upstairs to a tranquil primary suite w/spa-like bath or escape to the skylit top-floor office or family room. The roomy basement offers space to dream-whether a home gym, playroom, or creative studio. Tucked in a welcoming neighborhood just ? mile to the new Lynch School (opening Fall 2025), and located close to Winchester HS, shopping & eateries, Winchester Center & commuter rail (20 mins to Boston), this home offers the perfect blend of comfort, privacy, & convenience

Home for Sale in Winchester

This sun-filled 2012 townhouse, with its spacious layout, backyard oasis & attached garage, lives like a single-family home. Spend weekends lounging on the private deck, unwinding under the pergola, or playing on the lush, fenced lawn. Inside, the inviting open layout is made for gathering?whether around the gas fireplace on cozy evenings or at the kitchen island while entertaining friends. High ceilings & hardwood floors create an airy, elegant feel, while the porch & backyard invite connection to the outdoors. Retreat upstairs to a tranquil primary suite w/spa-like bath or escape to the skylit top-floor office or family room. The roomy basement offers space to dream-whether a home gym, playroom, or creative studio. Tucked in a welcoming neighborhood just ? mile to the new Lynch School (opening Fall 2025), and located close to Winchester HS, shopping & eateries, Winchester Center & commuter rail (20 mins to Boston), this home offers the perfect blend of comfort, privacy, & convenience

Home for Sale in Winchester

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 charger. Designed with input from Louis Ashman for today?s lifestyle and located near Winchester?s shops, dining, parks, and commuter rail. Don?t miss your chance to own this last available unit!

Home for Sale in Winchester

Welcome to The Ledges?an exceptional custom-designed ?E? style end-unit townhouse offering over 10 rooms of refined living space and a distinctive layout found in no other unit. Thoughtfully maintained and tastefully updated, this residence features an expansive open floor plan with cathedral ceilings, elegant crown molding, and a gourmet chef?s kitchen equipped with premium appliances. The first floor includes formal living and dining rooms, a built-in office, and a luxurious primary suite with dual walk-in closets, a spa-like bath, and direct access to a private deck overlooking a tranquil wooded setting. The second level offers a spacious bedroom, full bath, and additional office or flex space. The fully finished walk-out lower level, complete with custom built-ins and access to a serene, tree-lined common outdoor area, provides the ideal space for guests/extended family. Located near the clubhouse, pool, and tennis courts, with convenient access to Winchester Center & major routes!

Home for Sale in Winchester

Exceptional colonial on Myopia Hill showcasing an expansive rear family room addition, perfectly situated on an idyllic lot surrounded by lush gardens & mature landscape. This stately residence offers a true private oasis just minutes from all conveniences. Rich in finish, elegant in design w/ stunning living areas, large scale rooms & 4 fireplaces creating warm inviting spaces for every day living & entertaining. The custom kitchen leads to dramatic family room w/vaulted ceiling & walls of windows w/ fireplace & access to expansive patio w/ breathtaking views; seamlessly blending indoor & outdoor living. A formal dining room just off the kitchen provides an ideal space for hosting. This thoughtfully designed home includes 5 large beds & 4.5 baths, including the primary suite w/ beautiful bath & large walk in closet. A separate in-law apartment / guest suite offers flexibility & privacy for extended stays. Finished basement w/ family room, game room & gym plus 2 car direct entry garage

Home for Sale in Winchester

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 spacious front porch or dinner al fresco on the secluded patio, surrounded by gorgeous gardens. The detached garage has room for a car and storage. A short stroll to Winchester's award-winning schools, the quintessential downtown, boutiques, eateries, commuter rail, the Fells, and more.