Winchester Real Estate

Winchester: A Charming Town in Middlesex County, Massachusetts

Nestled in Middlesex County, Massachusetts, Winchester is a picturesque town that offers a perfect blend of small-town charm and urban convenience. Known for its beautiful neighborhoods, excellent schools, and close-knit community, Winchester is a highly sought-after place to call home.

With its prime location just eight miles north of downtown Boston, Winchester provides residents with easy access to the city's vibrant cultural scene, renowned universities, and job opportunities. Commuting is a breeze, thanks to the town's well-connected transportation system, including nearby highways and commuter rail stations.

Winchester boasts a rich history and is dotted with historic landmarks and architectural gems. The town center features a delightful mix of locally-owned shops, restaurants, and cafes, perfect for leisurely strolls and exploring. Residents can also enjoy the outdoors at the Middlesex Fells Reservation, a nearby nature reserve offering hiking trails, scenic views, and recreational activities.

Families are drawn to Winchester for its exceptional school system, which consistently ranks among the top in the state. The town's commitment to education is evident in its state-of-the-art facilities and dedicated faculty, providing students with a solid foundation for their future.

Real estate options in Winchester are diverse, with a range of architectural styles and property types to suit different preferences and budgets. From charming historic homes to modern condominiums, there is something for everyone in this vibrant community.

Whether you are looking for a peaceful suburban retreat or a place to raise a family, Winchester offers a welcoming and thriving community with all the amenities one could desire. Discover the charm of this Middlesex County gem and make Winchester your next home.

Newest Listings in Winchester

$1,450,000

8 Beds ⋅ 6 Baths ⋅ 73594547 MLS

Excellent development opportunity in Winchester! This 22,403 sq. ft. lot at 67-69 Hemingway Street is approved for the construction of two townhomes, with architectural plans included in the sale. The proposed design features two spacious residences, each offering 4 bedrooms, 2.5 baths, open-concept living and dining areas, mudroom, walk in pantry, a private primary suite, outdoor living space, an attached garage, and the option to finish the basement for additional living space. Zoned RG, the property will be delivered as a vacant lot, with public water, public sewer, and natural gas available, providing an excellent opportunity for builders and developers to bring this project to life. The location offers an appealing combination of neighborhood living, outdoor recreation, and commuter convenience. Just minutes from the newly constructed Lynch Elementary School, Horn Pond's scenic walking trails, and the Tri-Community Bike Path, the property provides easy access to some of Winchester's favorite outdoor destinations. Downtown Winchester offers a vibrant mix of local shops, restaurants, cafés, and community amenities, along with commuter rail service to Boston. Convenient access to Routes 93 and 95 adds to the property's appeal. Winchester continues to be a highly desirable community with a strong buyer pool seeking quality new construction. With approvals in place, architectural plans included, and a location that appeals to today's homebuyers, this is an attractive opportunity to develop two new residences in one of the area's most sought-after markets.

67-69 Hemingway St, Winchester

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

$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.

$1,049,000

4 Beds ⋅ 2 Baths ⋅ 73594513 MLS

Welcome to 16-18 Russell Road, a classic two-family home tucked along a tranquil one-way street just a short walk from downtown Winchester. The bright upper level features 3 bedrooms and 1 bath, while the flexible lower level offers a 1-bedroom, 1-bath layout with the potential to expand to two bedrooms, providing added versatility for investors, multigenerational living, or owner-occupants looking to offset their mortgage with rental income. Hardwood floors run throughout much of the home, while ductless mini-split systems provide efficient heating and cooling, complemented by a gas forced-air system in the basement*. Vinyl siding and an asphalt roof help keep exterior maintenance manageable, while ample off-street parking and a yard add everyday convenience. Located within the district for the newly built Lynch Elementary School, the home is also just a short walk to the commuter rail, a new neighborhood coffee shop, restaurants, and amenities of Winchester's vibrant town center.

16-18 Russell Rd, Winchester

Listing courtesy of Listing Agent: Andersen Group Realty from Listing Office: Keller Williams Realty Boston Northwest.

$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.

$1,299,000

6 Beds ⋅ 2 Baths ⋅ 73592723 MLS

An exceptional turnkey opportunity in Winchester, 419–421 Washington Street presents a beautifully refreshed two-family residence featuring significant mechanical upgrades and refined finishes throughout. Major improvements include a brand-new roof, newly paved driveway with parking for 4–5 vehicles, separate central heating and air conditioning systems, separate utilities, fresh interior and exterior paint, and beautifully refinished hardwood floors. Ideally situated near vibrant Winchester Center, enjoy convenient access to local dining, boutique shopping and commuter rail service to Boston. Proximity to Winchester Hospital, I-93, Route 128/I-95, Middlesex Fells Reservation and Winchester's highly regarded schools further enhances the appeal. Move-in ready with extensive recent improvements, this exceptional property offers an ideal opportunity for owner-occupants and investors seeking lasting value in one of Greater Boston's most desirable communities.

419-421 Washington St, Winchester

Listing courtesy of Listing Agent: The Marrocco Group from Listing Office: Coldwell Banker Realty - Lexington.

$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.

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Winchester Real Estate

Newest Listings in Winchester

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