Winchester Homes for Sale

Welcome to Winchester, a charming town located in Middlesex County, Massachusetts. Known for its picturesque surroundings, Winchester offers a perfect blend of small-town charm and modern amenities.

For those looking to make Winchester their home, there are plenty of beautiful properties available. From historic colonial-style homes to modern condos, Winchester has a diverse range of real estate options to suit every taste and budget. Whether you're looking for a cozy starter home or a spacious family estate, you're sure to find the perfect property in this lovely town.

With top-rated schools, a strong sense of community, and easy access to Boston and other major cities, Winchester is a highly desirable place to live. Residents enjoy a high quality of life, with plenty of parks, shops, and restaurants to explore. Whether you're a nature lover, a history buff, or a foodie, Winchester has something for everyone.

If you're considering making Winchester your home, now is a great time to explore the available homes for sale. Don't miss out on the opportunity to live in this wonderful town and experience all that Winchester has to offer. Get in touch with a local real estate agent to start your home search today!

Newest Winchester Homes for Sale

$1,049,900

3 Beds ⋅ 2 Baths ⋅ 73595417 MLS

Welcome to 28 Olive Street, a renovated 3-bedroom, 2-bath ranch in Winchester with 1,783 square feet of finished living space and a top-to-bottom update that lets you move right in. The main level centers on an all-new, slightly expanded eat-in kitchen that opens to an adjacent living room. A wood-burning fireplace and shiplap accent wall anchor the living room. The main living level features refinished hardwood floors, all-new doors, trim, ceilings, and lighting, plus new central AC. Three bedrooms share a completely updated full bath. Downstairs, the finished lower level adds valuable flexible space. The spacious recreation room offers plenty of space for a media area, gym, or home office, plus a second full bathroom, recessed lighting, vinyl flooring, and its own mini-split for heating and cooling. A separate utility room keeps storage, laundry, and mechanicals out of sight. The big-ticket items are done: new roof, windows, siding, electrical service, and exterior doors. The 6,527-square-foot corner lot has a private driveway, new entry stairs, and a crisp new white vinyl fence surrounding the entire property. With the heavy lifting already complete, 28 Olive Street is a rare chance to own in Winchester without the projects. Staging and photos are being done Thursday. First showings are Thursday at the open house. Offers, if any, will be reviewed Monday at Noon.

28 Olive St, Winchester

Listing courtesy of Listing Agent: Ethan Forrest from Listing Office: The Aland Realty Group LLC.

$2,999,000

5 Beds ⋅ 5 Baths ⋅ 73594545 MLS

New construction currently underway. Estimated completion in approximately Spring/Summer 2027. Set on an impressive 22,629 sq. ft. lot, this beautifully crafted new construction offers exceptional space, thoughtful design, and a peaceful setting with easy access to the Middlesex Fells Reservation and I-93. Designed for today's lifestyle, the main level features a welcoming foyer, elegant living and dining rooms, a spacious family room with fireplace, and a stunning chef's kitchen with a walk-in pantry and adjoining mudroom and half bath. Upstairs, the luxurious primary suite is complemented by four additional bedrooms, 4 beautifully appointed baths, and a convenient second-floor laundry room. An attached two-car garage, generous backyard, and exceptional craftsmanship throughout complete this rare opportunity to own a stunning new home on a charming side street.

5 Forest Cir, Winchester

Listing courtesy of Listing Agent: Pirani & Wile Group from Listing Office: Gibson Sotheby's International Realty.

$2,650,000

4 Beds ⋅ 5 Baths ⋅ 73593868 MLS

Inspired by the timeless villas of Europe, this exceptional residence blends classic elegance with modern design. A dramatic curved staircase and soaring architectural details introduce inviting living spaces featuring handcrafted finishes, antique beams, stone fireplaces, and expansive French doors that connect seamlessly to the outdoors. At the heart of the home, a chef’s kitchen showcases custom cabinetry, luxury appliances, and an adjoining mudroom. The outdoor setting offers a private retreat with a granite-columned loggia, heated saltwater pool, landscaped grounds with irrigation, and multiple areas for entertaining.The spa-inspired primary suite, ensuite guest bedrooms, and finished lower level with flexible bonus spaces provide comfort and versatility. Heated driveways and walkways add year-round convenience. Ideally located within walking distance of downtown, the new Lynch School, the new commuter rail station, and an array of shops and restaurants, this home offers a thoughtful balance of timeless style, modern amenities, and everyday comfort.

18 Middlesex St, Winchester

Listing courtesy of Listing Agent: Jennifer Taves from Listing Office: Coldwell Banker Realty - Boston.

$3,799,000

8 Beds ⋅ 6 Baths ⋅ 73593484 MLS

Welcome to 15 Foxcroft Road, an 8-bedroom home with 4 full and 2 half baths in Winchester's sought-after Flats neighborhood, offering over 7,000 sq ft on a beautiful corner lot. Two private suites make it ideal for multigenerational living, in-laws, caregivers, au pairs, or long-term guests, with ADU-style flexibility already built in. A full 2012 renovation created a large kitchen with oversized butler's pantry, a spacious family room with built-in cabinetry, a dining room, a playroom, and a mudroom with half bath on the first floor. The second floor has four more bedrooms, including a primary suite with full bath and large walk in closet. The third floor adds an additional bedroom and an office as well as cedar closet. The finished lower level features a full bar, a half bath, and ample space for a game room or media room. This property offers the unique ability to offer two suites perfect for extended family or caretakers. The first-floor suite offers single-level living with two bedrooms, a living room, and a full bath with a zero-entry shower. The second-floor suite has its own private staircase, bedroom, living room, and full bath for real independence from the main household. Outside, enjoy a fully fenced yard, wraparound porch, patio with fire pit, and an attached two-car garage. A unique and special property in one of Winchester's best neighborhoods!

15 Foxcroft Rd, Winchester

Listing courtesy of Listing Agent: Karen S. Garrett from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.

$2,950,000

6 Beds ⋅ 4 Baths ⋅ 73592433 MLS

Spacious seven-bedroom, four-bath home in one of the area's most sought-after neighborhoods, thoughtfully designed with the flexible living space today's lifestyles demand. Whether accommodating a multigenerational household, extended family, long-term guests, or creating dedicated work and hobby spaces, this home offers exceptional versatility. The main level features an oversized living room with an open-concept layout flowing seamlessly into the dining area and kitchen, creating the perfect gathering space for everyday living and entertaining. French doors open to a large deck, extending the living space outdoors. Two first-floor bedrooms and a full bath provide convenient options for guests, family members, or a home office. Upstairs, you'll find four additional bedrooms, including a spacious primary suite with its own private balcony, a peaceful retreat to begin and end the day. The finished lower level adds even more flexibility with a generous family room, an additional bedroom or office, and direct access to the heated three-car garage. With abundant space to grow, gather, and adapt to changing needs, this exceptional home is ready to welcome its next chapter.

18 Surrey Road, Winchester

Listing courtesy of Listing Agent: Mary Kelly from Listing Office: Century 21 Property Central Inc..

$1,125,000

3 Beds ⋅ 2 Baths ⋅ 73591400 MLS

Welcome to this charming center-entrance Colonial, ideally situated on a lovely side street just moments from Winchester Center! Offering 3 bedrooms and 1.5 baths, this sun-filled home is ready for its next owners to make it their own. Timeless features include hardwood floors, a cozy fireplace, a sunroom, a full basement, a detached garage, and a wonderful yard with patio—perfect for relaxing or entertaining. The spacious eat-in kitchen offers plenty of room for gathering with family and friends. The primary bedroom has a generously sized walk-in closet and views of breathtaking sunsets. Lovingly maintained and cherished for many years, this special home is ready to welcome its next chapter and create lasting memories for years to come.

8 Stone Ave, Winchester

Listing courtesy of Listing Agent: Lesley Smith from Listing Office: Barrett Sotheby's International Realty.

$890,000

2 Beds ⋅ 1 Baths ⋅ 73591108 MLS

Endless possibilities in this well-loved home less than 1/3rd mile from Winchester High School. Owned by the same family since 1950, this home has been lovingly cared for and is now ready for your updates. The main floor features high ceilings, an eat-in kitchen, and a large rear family sunroom drenched in light. Upstairs you'll find a front-to-back main bedroom, full bath, and nursery, as well as a finished staircase to the third floor, which was used as additional bedroom space. Large level back yard on a quiet street means ample opportunity to entertain or expand.

80 Nelson St, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.

$1,399,000

3 Beds ⋅ 3 Baths ⋅ 73590311 MLS

Situated on a quiet cul-de-sac in a desirable Winchester neighborhood surrounded by substantial homes, this well-maintained 3-bedroom, 2.5-bath Split-Level offers comfortable living and plenty of potential on a generous 19,998 sq. ft. lot. Built in 1976, the home features hardwood floors throughout and central air conditioning. The main level includes a spacious living room, formal dining room, and eat-in kitchen with access to a screened porch overlooking the backyard. Three bedrooms, including a primary suite with private bath and a renovated family bathroom, complete this floor. The lower level provides additional living space with a family room featuring a fireplace, laundry area, half bath, and direct access to the attached two-car garage. Lovingly cared for over the years, this home is ready to enjoy as is, with room to make it your own over time. Conveniently located near Vinson-Owen School, Wright-Locke Farm, and the Winchester Swim & Tennis Club, it's a great opportunity to settle into one of Winchester's sought-after neighborhoods.

6 Aricia Ln, Winchester

Listing courtesy of Listing Agent: Pirani & Wile Group from Listing Office: Gibson Sotheby's International Realty.

$1,985,000

4 Beds ⋅ 4 Baths ⋅ 73589478 MLS

Set on over an acre of beautifully landscaped grounds abutting acres of woodland, this extensively renovated Contemporary Cape offers exceptional privacy and a peaceful connection to nature. A thoughtfully designed open floor plan features hardwood floors, a fireplaced living room, elegant dining room, and a beamed-ceiling family room adjoining the remodeled kitchen with stone counters, stainless appliances, and island. A private great room off the foyer, with windows on three walls and a slider to the spacious deck, offers a wonderful retreat. French doors open to the expansive deck overlooking the fenced backyard and wooded surroundings. Upstairs, four bedrooms include a primary suite with custom closets and private bath. The finished walkout lower level offers flexible space for a home office, gym, or guests, with separate entrance and full bath. Stone walls, mature landscaping, a long private driveway, and two-car garage complete this exceptional home.

30 Surrey Rd, Winchester

Listing courtesy of Listing Agent: Anne Spry from Listing Office: Barrett Sotheby's International Realty.

$1,399,000

5 Beds ⋅ 2 Baths ⋅ 73588977 MLS

Welcome to 15 Lloyd Street, ideally situated in one of Winchester’s most desirable downtown neighborhoods! This charming, recently updated colonial welcomes you with a newly constructed farmers porch & features 4- 5 bedrooms, 1.5 baths, and a flexible layout with plenty of space for everyday living, working from home, and entertaining. The inviting sun-drenched living room features high ceilings and opens to the dining room which has slider access to a large deck, along with an eat in kitchen, 1/2 bath and spacious entry foyer blending together to create a warm and welcoming home to enjoy. The second floor features 4 bedrooms including a spacious primary along with a full hall bath. An additional bedroom or recreation space and office add great bonus space on the third floor. Some recent 2024 updates include new roof, heating system/HVAC, new front porch, updated electrical, all new hardwood floors, new window and baseboard trim in LR/FR & more! Walk out lower level offers laundry area & provides potential for future expansion/ family, game room. Additional highlights include a detached garage, off-street parking, and lovely yard to enjoy. Conveniently located in the heart of downtown Winchester close to parks, public transportation, and all that Winchester has to offer. This is a wonderful opportunity to enjoy the charm and convenience of this great home located in one of the town’s most sought-after neighborhoods! **Open houses Saturday & Sunday please stop by!**

15 Lloyd Street, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.

$1,299,000

3 Beds ⋅ 2 Baths ⋅ 73588863 MLS

Welcome to this beautifully updated and meticulously maintained 3-4 bedroom, 2 full bath home, perfectly blending timeless charm with modern amenities. An inviting farmer’s porch sets the tone for this wonderful property, situated on an expansive, level lot offering exceptional space for outdoor enjoyment. The main level features a spacious family room with a gas fireplace, custom built-ins, and a convenient desk area. French doors lead to an elegant dining room with classic chair rail detailing. The stunning, newly renovated modern kitchen features stylish finishes, stainless steel appliances, and thoughtfully designed space for everyday living. A beautifully updated full bath and versatile room office/bedroom with a new walk-in closet complete the first floor. Upstairs offers three bedrooms with hardwood floors, an updated full bath, and a charming office nook. Additional improvements new mini-split systems throughout, and an EV charger. Enjoy the oversized screened-in porch overlooking the expansive, level backyard, perfect for relaxing or entertaining. A detached oversized garage provides additional storage, while the lower level offers excellent potential for future use and duplex potential.Ideally located in Winchester's desirable Muraco Elementary School district, this move-in-ready home offers an exceptional combination of charm, comfort, and modern convenience!

39 Forest St, Winchester

Listing courtesy of Listing Agent: Danielle Storella from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.

$1,999,000

5 Beds ⋅ 4 Baths ⋅ 73588059 MLS

Welcome to this beautifully appointed and exceptionally spacious home, ideally situated in a quiet, desirable West Side Winchester neighborhood within the sought-after Vinson-Owen School district. Offering an impressive combination of elegant living spaces, flexible accommodations, and thoughtful upgrades, this home provides room for everyone while easily adapting to a variety of lifestyles. At the heart of the home is the expansive granite kitchen, designed for both everyday living and entertaining. Custom cabinetry, Thermador double ovens, a Dacor warming drawer, Sub-Zero refrigerator, wine refrigerator, recessed lighting, and an impressive 50-square-foot center island create a wonderful gathering space with plenty of room for cooking, dining, and entertaining. The kitchen flows into a comfortable family room featuring a custom-built entertainment center and electric fireplace. A gracious formal dining room showcases handcrafted molding and classic wainscoting, while additional first-floor living spaces provide tremendous flexibility for a formal living room, playroom, home office, den, or whatever best suits your needs.One of the home's most appealing features is the first-floor bedroom suite with a full bath, offering exceptional versatility for extended family, guests, an au pair, or anyone seeking the convenience of first-floor living. A dedicated laundry room on this level adds even more functionality. With multiple living areas and flexible rooms throughout the first floor, there are countless ways to create private spaces for additional family members while still enjoying plenty of room to gather together.Upstairs, the generously sized primary suite provides a relaxing retreat with vaulted ceilings, recessed lighting, double closets, and a beautifully tiled private bath with double sinks. Three additional spacious bedrooms, another full bath, and additional office space provide abundant room for family, guests, work-from-home needs, hobbies, or study areas.With its generous proportions, flexible floor plan, multiple bedroom and living configurations, and outstanding West Side location, this is a home designed to grow and change with its owners. Enjoy the peace and privacy of a quiet neighborhood while being part of the wonderful Winchester community. This is more than simply a beautiful house—it is a home offering the space, versatility, and comfort today's buyers are looking for.

21 Amberwood Dr, Winchester

Listing courtesy of Listing Agent: Gayle Winters & Co. Team from Listing Office: Compass.

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Winchester Homes for Sale

Newest Winchester Homes for Sale

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