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

OPEN HOUSES ONLY Discover this meticulously maintained 3 bed colonial just steps from Muraco Elementary and the Middlesex Fells. Rich hardwood floors flow through the formal dining room into the oversized, fireplaced living room ideal for entertaining. The beautifully appointed kitchen features a sunny breakfast area with access to a private deck. Upstairs, you'll find 2 spacious bedrooms and a primary suite that boasts a walk-in closet and a stunning en-suite bath with clawfoot tub. From the driveway, enter a newly renovated basement space including mudroom and ample flex space for exercise room or media/play space. Recent updates include a new furnace, water heater and expanded driveway to accommodate additional parking spaces. 1 car garage. Central air, insulated windows and doors, and a programmable thermostat to reduce annual energy costs. Fabulous location, steps from the Tri-Community bike path, hiking trails, Leonard Field, playgrounds and tennis courts

This affordable Colonial in the highly sought-after Muraco School district is brimming with potential and ready for your personal vision. An ideal starter home, it features a spacious backyard overlooking Davidson Park, creating a private and peaceful setting. Conveniently located near parks, bike trails, and public transportation, this home offers an exceptional combination of value, location, and opportunity. Whether you're a contractor, investor, or homeowner looking to build equity, this diamond in the rough is full of possibilities

OPEN HOUSES ONLY Discover this meticulously maintained 3 bed colonial just steps from Muraco Elementary and the Middlesex Fells. Rich hardwood floors flow through the formal dining room into the oversized, fireplaced living room ideal for entertaining. The beautifully appointed kitchen features a sunny breakfast area with access to a private deck. Upstairs, you'll find 2 spacious bedrooms and a primary suite that boasts a walk-in closet and a stunning en-suite bath with clawfoot tub. From the driveway, enter a newly renovated basement space including mudroom and ample flex space for exercise room or media/play space. Recent updates include a new furnace, water heater and expanded driveway to accommodate additional parking spaces. 1 car garage. Central air, insulated windows and doors, and a programmable thermostat to reduce annual energy costs. Fabulous location, steps from the Tri-Community bike path, hiking trails, Leonard Field, playgrounds and tennis courts

Step into the welcoming foyer and take in the period detail: stained-glass windows, large bow windows, detailed moldings, and hardwood floors. The sun-drenched formal dining room is made for gatherings, and the updated kitchen with butler's pantry makes entertaining a pleasure. On the 2nd floor, the primary suite includes a private office and sleeping porch, along with two additional bedrooms, a full bath, and laundry. The 3rd floor offers two more bedrooms and a full bath, providing flexibility for any household. The large screened porch extends living space through the warmer months, providing a quiet spot to read, dine, or relax. The flat backyard is peaceful and private, with perennial gardens and a bluestone patio perfect for al fresco dining. A mudroom and two-car garage add everyday practicality. Set on a quiet, dead-end street, minutes from the trails of the Middlesex Fells, and close to Muraco Elementary, downtown Winchester, the commuter rail, shops, cafes, and restaurants

OPEN HOUSES ONLY Discover this meticulously maintained 3 bed colonial just steps from Muraco Elementary and the Middlesex Fells. Rich hardwood floors flow through the formal dining room into the oversized, fireplaced living room ideal for entertaining. The beautifully appointed kitchen features a sunny breakfast area with access to a private deck. Upstairs, you'll find 2 spacious bedrooms and a primary suite that boasts a walk-in closet and a stunning en-suite bath with clawfoot tub. From the driveway, enter a newly renovated basement space including mudroom and ample flex space for exercise room or media/play space. Recent updates include a new furnace, water heater and expanded driveway to accommodate additional parking spaces. 1 car garage. Central air, insulated windows and doors, and a programmable thermostat to reduce annual energy costs. Fabulous location, steps from the Tri-Community bike path, hiking trails, Leonard Field, playgrounds and tennis courts

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

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!

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 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

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!

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

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!

Step into the welcoming foyer and take in the period detail: stained-glass windows, large bow windows, detailed moldings, and hardwood floors. The sun-drenched formal dining room is made for gatherings, and the updated kitchen with butler's pantry makes entertaining a pleasure. On the 2nd floor, the primary suite includes a private office and sleeping porch, along with two additional bedrooms, a full bath, and laundry. The 3rd floor offers two more bedrooms and a full bath, providing flexibility for any household. The large screened porch extends living space through the warmer months, providing a quiet spot to read, dine, or relax. The flat backyard is peaceful and private, with perennial gardens and a bluestone patio perfect for al fresco dining. A mudroom and two-car garage add everyday practicality. Set on a quiet, dead-end street, minutes from the trails of the Middlesex Fells, and close to Muraco Elementary, downtown Winchester, the commuter rail, shops, cafes, and restaurants

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

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

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

Two-family homes in Winchester are limited, which is exactly why opportunities like this get attention quickly. Whether you are looking for an owner-occupied property with rental income or a solid long-term investment, this one checks the boxes. The larger unit spans the second and third floors, offering three bedrooms, two full baths, and living space that feels more like a single-family home. The first-floor unit includes two bedrooms and one full bath, making it ideal for rental income, extended family, or multi-generational living. Each unit has its own garage space, something tenants and owners always appreciate, plus a long driveway with plenty of additional parking. The layout offers separation, functionality, and strong future potential. Location matters, and this property comes with access to the highly desirable Winchester Public Schools, adding even more long-term value. Investment properties in Winchester do not come along often, especially ones with this much upside

This affordable Colonial in the highly sought-after Muraco School district is brimming with potential and ready for your personal vision. An ideal starter home, it features a spacious backyard overlooking Davidson Park, creating a private and peaceful setting. Conveniently located near parks, bike trails, and public transportation, this home offers an exceptional combination of value, location, and opportunity. Whether you're a contractor, investor, or homeowner looking to build equity, this diamond in the rough is full of possibilities

Two-family homes in Winchester are limited, which is exactly why opportunities like this get attention quickly. Whether you are looking for an owner-occupied property with rental income or a solid long-term investment, this one checks the boxes. The larger unit spans the second and third floors, offering three bedrooms, two full baths, and living space that feels more like a single-family home. The first-floor unit includes two bedrooms and one full bath, making it ideal for rental income, extended family, or multi-generational living. Each unit has its own garage space, something tenants and owners always appreciate, plus a long driveway with plenty of additional parking. The layout offers separation, functionality, and strong future potential. Location matters, and this property comes with access to the highly desirable Winchester Public Schools, adding even more long-term value. Investment properties in Winchester do not come along often, especially ones with this much upside

OPEN HOUSES ONLY Discover this meticulously maintained 3 bed colonial just steps from Muraco Elementary and the Middlesex Fells. Rich hardwood floors flow through the formal dining room into the oversized, fireplaced living room ideal for entertaining. The beautifully appointed kitchen features a sunny breakfast area with access to a private deck. Upstairs, you'll find 2 spacious bedrooms and a primary suite that boasts a walk-in closet and a stunning en-suite bath with clawfoot tub. From the driveway, enter a newly renovated basement space including mudroom and ample flex space for exercise room or media/play space. Recent updates include a new furnace, water heater and expanded driveway to accommodate additional parking spaces. 1 car garage. Central air, insulated windows and doors, and a programmable thermostat to reduce annual energy costs. Fabulous location, steps from the Tri-Community bike path, hiking trails, Leonard Field, playgrounds and tennis courts

Step into the welcoming foyer and take in the period detail: stained-glass windows, large bow windows, detailed moldings, and hardwood floors. The sun-drenched formal dining room is made for gatherings, and the updated kitchen with butler's pantry makes entertaining a pleasure. On the 2nd floor, the primary suite includes a private office and sleeping porch, along with two additional bedrooms, a full bath, and laundry. The 3rd floor offers two more bedrooms and a full bath, providing flexibility for any household. The large screened porch extends living space through the warmer months, providing a quiet spot to read, dine, or relax. The flat backyard is peaceful and private, with perennial gardens and a bluestone patio perfect for al fresco dining. A mudroom and two-car garage add everyday practicality. Set on a quiet, dead-end street, minutes from the trails of the Middlesex Fells, and close to Muraco Elementary, downtown Winchester, the commuter rail, shops, cafes, and restaurants

Two-family homes in Winchester are limited, which is exactly why opportunities like this get attention quickly. Whether you are looking for an owner-occupied property with rental income or a solid long-term investment, this one checks the boxes. The larger unit spans the second and third floors, offering three bedrooms, two full baths, and living space that feels more like a single-family home. The first-floor unit includes two bedrooms and one full bath, making it ideal for rental income, extended family, or multi-generational living. Each unit has its own garage space, something tenants and owners always appreciate, plus a long driveway with plenty of additional parking. The layout offers separation, functionality, and strong future potential. Location matters, and this property comes with access to the highly desirable Winchester Public Schools, adding even more long-term value. Investment properties in Winchester do not come along often, especially ones with this much upside

This affordable Colonial in the highly sought-after Muraco School district is brimming with potential and ready for your personal vision. An ideal starter home, it features a spacious backyard overlooking Davidson Park, creating a private and peaceful setting. Conveniently located near parks, bike trails, and public transportation, this home offers an exceptional combination of value, location, and opportunity. Whether you're a contractor, investor, or homeowner looking to build equity, this diamond in the rough is full of possibilities