3,146 properties for sale in Winchester Highlands, Winchester town Middlesex County Massachusetts

Timeless Victorian grandeur meets modern living in this iconic Winchester home situated on the corner of Wilson Street w/ easy access to Fells trails! This recently renovated sun-filled 6 BR 4 BA home offers nearly 5000 ft.2 of beautifully scaled living spaces filled w/ extraordinary architectural charm and elegant details featuring a brand new state of the art gorgeous kitchen w/ Wolf and Sub Zero appliances. A stunning staircase showcases a wall of colorful leaded glass complimented by high ceilings, intricate millwork and dramatic details throughout. The expansive rebuilt wrap-around porch offers wonderful space to enjoy summer evenings and host gatherings. The great layout provides flexibility for entertaining, working from home or extended living needs. The striking facade and stately presence creates an unforgettable first impression ideally located near Winchester Center, commuter rail, shops, restaurants and top rated schools. located in one of Winchester's most sought after ne

Pleased to present this meticulously maintained and nicely updated two family home in the heart of Winchester! Each spacious unit is one level and features seven rooms including 3 large bedrooms, living room w fplc, dining room w/wainscoting, sunroom, kitchen and updated baths. The generously sized flowing rooms are highlighted by high ceilings, oversized windows, beautiful original woodwork and timeless architectural details; seamlessly blended with thoughtful updates throughout. This home presents an exceptional opportunity for investors, owner occupants w/ an income unit or for multi generational living. Enjoy the private landscaped back yard shaded by mature trees, perfect for relaxing or outdoor gatherings. Ideally located close to town, schools, shops, restaurants, commuter rail, and all Winchester has to offer. The special property combines character space and convenience all in one of the areas most desirable locations, a rare opportunity not to be missed!

Welcome home to this sun-filled, south-facing 4-bed Colonial in a beloved Winchester neighborhood. Hardwood floors guide you from the gracious foyer into a spacious, fireplaced living room ideal for gatherings. The airy formal dining room flows seamlessly onto a private back deck overlooking a professionally landscaped, fully fenced yard-perfect for al fresco dining and entertaining. The updated chef's kitchen features stainless appliances and a generous island for everyday living. Upstairs, find 4 spacious bedrooms and a redone full bath boasting marble counters and custom tiled shower. The finished lower level provides exceptional flexibility w/ mudroom, full bath and ample flex space for a family room, gym and play area. Outside features a detached 1-car garage and 4-car driveway. Freshly painted inside and out. Fabulous location, blocks from Muraco Elementary, parks, playgrounds, the Fells and commuter routes. Move right in!

This completely remodeled home is nestled on a dead end street off Brookside Road, offering a serene/ natural setting with unmatched privacy. This home offers 4 bedrooms, and 2.5 baths with three spacious finished levels. The completely reimagined open concept main floor features a stunning kitchen open to dining area and large family room, plus a separate living room, mudroom, half bath and enclosed sun porch. The second floor includes a generous primary suite with views of nothing but nature, a walk-in closet and all new private bath; three additional bedrooms, a full hall bath and second floor laundry complete this floor. The finished walkout lower level offers a fitness room and large recreation room/media/ playroom with walls of windows showcasing the beautiful setting. Conveniently located near the Fells, Tri-Community bike path, Leonard Field and Muraco School but set back in a uniquely private location. Rare opportunity to move into a fully renovated, modern home at great price

Exceptional opportunity for investors, owner-occupants, or multigenerational living in this two-family home conveniently located near Winchester Center, restaurants, shopping, commuter rail, and major routes. The first floor has 2 bedrooms plus an office, while the second floor includes a third bedroom. Both units are filled with natural light and share nearly identical layouts with enclosed front porches, spacious front-to-back living and dining rooms, original built-in china cabinets, high ceilings, and timeless character throughout. The kitchens offer granite countertops, stainless steel appliances, dedicated pantries, and access to rear porches, while renovated bathrooms and freshly painted interiors add modern appeal. Additional highlights include a 2-car garage, 4 off-street parking spaces, hardwood floors throughout, basement storage, laundry, and an expansive private backyard

Thoughtfully reimagined and expanded in 2019, this sophisticated colonial offers 5-6 bedrooms and 5 baths with a beautiful open floor plan - perfect for a growing family or multi-generational living. A striking granite kitchen with crisp white cabinetry, premium stainless appliances and oversized island flows seamlessly into the dining area - ideal for everyday living and refined entertaining. A fireplaced living room, office, bedroom and full bath complete this main level. Upstairs, two spacious bedrooms and a family bath complement a serene primary suite with spa-like bath amenities. The 3rd level offers an additional primary suite with luxurious soaking tub and flexible bonus space to use how you choose. A finished walk-out lower level with wet bar, bath, family room, exercise and play space adds further appeal. Acoustic windows enhance comfort throughout. Enjoy the one car garage, fully fenced yard, patio and deck - just moments to parks, town center, major routes, and Winchester's

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

Presenting an exceptional opportunity at 17 Cherry Street, Medford, MA, a distinguished multi-family residence constructed in 1925, Completely renovated from Stubs and finished in 2024. offering a generous 4680 square feet 15R/10BD/6BR of meticulously designed living space. This property represents a unique offering for discerning buyers seeking a blend of classic architecture and versatile living arrangements. The residence is configured across three expansive stories, accommodating a total of 10 well-proportioned bedrooms, providing ample private accommodations. Complementing these living spaces are 6 full bathrooms, strategically located to serve the needs of multiple occupants with comfort and convenience. Situated on a substantial 5556 square foot lot, this property offers considerable outdoor potential, complementing its expansive interior footprint. To truly appreciate the scale and potential of this remarkable multi-family property, a private viewing is highly recommended

Seller covers first 12 months HOA !Built in 1899 as a schoolhouse and thoughtfully converted into 20 distinctive residences, The Residences at Franklin School is an award-winning landmark recognized with the PRISM Award for Best Condominium Conversion in New England and a Housing Design Award. 304 is a bright, sun-filled corner unit. Soaring high ceilings and oversized windows bring in abundant natural light throughout the day, while the spacious open-concept living area offers excellent flexibility for everyday living. Beautifully preserved original hardwood floors add warmth, character, and lasting quality. Substantial brick construction enhances year-round comfort and creates an exceptionally peaceful living environment with minimal noise. The desirable split-bedroom layout places the two bedrooms on opposite sides of the home. Conveniently located near I-93, Assembly Row, Wegmans, Middlesex Fells Reservation, Wellington Station, and Routes 16 and 28, with easy access to Boston

Must see this completely renovated and expanded stately brick home located just outside the town center offering the perfect blend of timeless charm and modern living. Thoughtfully re-designed with an open concept layout, the home features a custom high end kitchen that flows into a gorgeous oversized family room addition* w/ walls of windows overlooking a stunning private backyard. Formal LR and DR, mudroom, stylish 1/2 bath and home office/sunroom complete this floor. The second floor offers, three spacious bedrooms and two full baths including the most perfect primary suite w/gorgeous bath plus a sitting room; while the third-floor provides two additional rooms, ideal for guest or office space. Many updates include new hardwood floors, new high end Pella windows, updated electrical, heating and cooling systems finished lower level offers excellent recreation Enjoy the great landscaped yard with patio, lawn and sports court! For sure a favorite gathering spot for family and friends