Discover Exceptional Homes for Sale in Winchester, MA with Marc Fiore

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Explore the vibrant real estate market of Winchester, MA, a highly sought-after community renowned for its picturesque landscapes, top-tier schools, and welcoming atmosphere. For those seeking premium homes for sale, Winchester offers an impressive array of properties, from stately Victorians in Winchester Center to elegant Colonials in Myopia Hill. Marc Fiore provides unparalleled insight into finding your perfect residence, whether you desire a family-friendly abode near Horn Pond or a luxurious estate with easy access to Boston. Discover diverse architectural styles and desirable neighborhoods where lifestyle meets convenience.

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Exploring Winchester, MA Real Estate Opportunities

A Glimpse into Winchester's Diverse Neighborhoods

Winchester, MA, presents a rich tapestry of distinct neighborhoods, each offering unique charm for prospective buyers searching for homes for sale. In Winchester Center, you will find beautifully preserved historic properties and vibrant community life. Moving toward Myopia Hill, the residences often feature grander estates with expansive lots, providing a sense of privacy and luxury. The Flats area is popular for its proximity to schools and town amenities, making it a prime location for family homes. Further afield, areas bordering the Middlesex Fells Reservation offer homes with serene natural surroundings, perfect for those who cherish outdoor access and tranquility.

Architectural Styles Among Winchester Homes for Sale

The selection of homes for sale in Winchester encompasses a broad spectrum of architectural periods and designs. Classic New England Colonial homes are abundant, often featuring spacious layouts and timeless appeal. Elegant Victorian houses, showcasing intricate details and historical grandeur, are also a prominent feature of the local market. Furthermore, buyers can discover charming Tudors, sophisticated Cape Cods, and modern constructions that blend contemporary living with Winchester's traditional aesthetic. Each home type contributes to the unique character of the Winchester real estate landscape, catering to diverse preferences.

Winchester Lifestyle: Education, Recreation, and Commuting

Award-Winning Schools and Family Amenities

A primary draw for families considering homes for sale in Winchester, MA, is its nationally recognized public school system. The district consistently receives high accolades, ensuring an excellent educational foundation for children from elementary through high school. Beyond academics, Winchester boasts numerous family-friendly amenities, including well-maintained parks, community sports programs, and cultural events that foster a strong sense of community and provide enriching experiences for residents of all ages.

Outdoor Recreation and Community Spirit

Winchester residents enjoy unparalleled access to nature and recreational activities. The expansive Middlesex Fells Reservation offers miles of hiking trails, biking paths, and scenic vistas, providing a natural escape just minutes from many Winchester homes. Horn Pond, with its picturesque walking loop and opportunities for kayaking, is another cherished local gem. Throughout the year, the town hosts various events, from farmers' markets to seasonal festivals, highlighting the robust community spirit that makes living in Winchester so desirable.

Seamless Commuting and Area Conveniences

For those seeking homes for sale with convenient access to urban centers, Winchester's location is ideal. The town provides direct access to Boston via the MBTA Commuter Rail, making it an attractive option for professionals. Major roadways like Route 93 are also easily accessible, facilitating travel throughout the Greater Boston area. Furthermore, Winchester offers a charming downtown with boutique shops, diverse dining options, and essential services, ensuring that daily conveniences are always within reach for its residents.

Navigating the Winchester, MA Housing Market

Understanding Value and Investment in Winchester Properties

The real estate market in Winchester, MA, is known for its stability and strong property values, reflecting the town's enduring appeal. Investing in homes for sale here often represents a sound financial decision, with properties maintaining their worth due to the highly desirable location, excellent schools, and premium lifestyle offerings. Understanding current market trends and property valuations is crucial for making informed decisions, and Marc Fiore provides expert guidance throughout this process.

Finding Your Ideal Home with Marc Fiore

When searching for homes for sale in Winchester, MA, navigating the competitive market requires local expertise and dedicated support. Marc Fiore possesses an in-depth understanding of Winchester's distinct neighborhoods and property types, assisting buyers in identifying homes that perfectly align with their specific criteria and lifestyle aspirations. The process of finding a home that meets both immediate needs and long-term goals is made seamless through personalized attention and comprehensive market knowledge.

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Newest Homes for Sale in Winchester, MA

$2,249,000

5 Beds ⋅ 4 Baths ⋅ 73574117 MLS ⋅ NEW Status

Built in 2021, this stunning home is ready for its next owners to enjoy. Its elevated setting provides a peaceful retreat with multiple areas for outdoor living, including a charming front porch. Inside, thoughtful design and exceptional attention to detail are evident throughout. The expansive open-concept kitchen, living and dining areas offer an ideal setting for entertaining, complemented by two gas fireplaces and central air. The luxurious primary suite features soaring ceilings, a walk-in closet, spa-like bath and private balcony. Three additional bedrooms offer generous proportions and ample closet space, while a conveniently located laundry room completes the second level. The ground floor provides a flexible living space ideal for guests, an au pair suite, or a recreation room. A whole-house generator offers added peace of mind. Ideally located approximately an equal distance to both Winchester and Arlington centers.

11 Locke St, Winchester

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

$2,199,000

4 Beds ⋅ 4 Baths ⋅ 73572955 MLS ⋅ ACTIVE Status

Welcome to 19 Hancock Street, a stunning transformation where timeless New England character meets sophisticated modern living. Completely reimagined through an extensive renovation, this exceptional Winchester residence preserves the charm and presence of a classic home while delivering the design, finishes and functionality expected for today’s lifestyle. The beautifully designed first floor features a bright, open layout with an effortless flow from room to room, creating an ideal setting for both elegant entertaining and comfortable everyday living. Thoughtful details throughout include a spacious pantry and dedicated mudroom, blending style with exceptional functionality. Upstairs, four bedrooms include a luxurious primary suite designed as a private retreat, complete with a beautifully appointed bath and oversized walk-in shower. Convenient second-floor laundry and well-designed secondary bedrooms make this level as practical as it is polished. The finished lower level offers another impressive dimension of living space, perfect for a media room, home gym, playroom, office or guest retreat. With 3.5 beautifully finished baths, a two-car garage, and a rear deck ideal for outdoor dining and entertaining, every level of the home has been thoughtfully considered. All of this is set in one of Winchester’s most convenient locations—just minutes from Winchester Center, the commuter rail, shops, dining and schools. Classic character, completely renewed. Modern luxury without sacrificing warmth. 19 Hancock Street is a rare opportunity to enjoy the best of Winchester living in a home that feels both established and entirely new.

19 Hancock Street, Winchester

Listing courtesy of Listing Agent: Vita Realty Group from Listing Office: Compass.

$1,749,000

5 Beds ⋅ 4 Baths ⋅ 73572890 MLS ⋅ ACTIVE Status

A rare offering in one of Winchester's most desirable neighborhoods, this spacious mid-century contemporary spans approximately 3,500 square feet with 5 bedrooms and 3.5 baths on a private 0.24-acre lot. The open main level flows from a light-filled living room with a cathedral ceiling, stained-glass accents, and a fireplace into the dining room, family room, and a renovated kitchen with Silestone quartz countertops, upgraded cabinetry, and direct deck access. Upstairs, two ensuite bedrooms anchor the floor plan, including a generous primary suite with a large jetted soaking tub, vanity, and walk-in closet. Three additional bedrooms and a family bath complete the level. Hardwood floors run throughout, a second fireplace warms the lower-level bonus room, and ductless mini-splits deliver year-round comfort throughout the house. The walk-out lower level offers a versatile bonus room with its own exterior entrance, ideal for a home office, gym, media room, playroom, or guest suite. Three decks extend the living space outdoors for entertaining and dining above the private backyard, and an attached two-car garage adds everyday ease. Set on a quiet street with easy access to commuter rail, downtown Winchester, parks, and bike or jog trails, this is a rare chance to live in your dream home in a community that has it all.

17 Churchill Rd, Winchester

Listing courtesy of Listing Agent: Domingo Medina from Listing Office: Coldwell Banker Realty - Lexington.

$675,000

2 Beds ⋅ 2 Baths ⋅ 73572854 MLS ⋅ ACTIVE Status

Enjoy Winchester living in this spacious 2-bed, 1.5-bath townhouse at the desirable Wedge Pond Condominium. The main level features hardwood floors, a sunny living room, dining room, half bath, and kitchen. On the second level, you have two bedrooms and a full bath. The finished lower level offers more space for a family room, home office, or guest bedroom, plus laundry and storage. To top it all off, you have a private outdoor patio with water views! One deeded parking space included with an additional second space available for $40 per month. Prime location - walk to downtown restaurants, commuter rail, schools, supermarket, beach, and much more. Updates include kitchen (2020) downstairs bathroom (2023) new windows (2026) heating (2020)

60 Lake St Unit E, Winchester

Listing courtesy of Listing Agent: Shaundize Moosavizadeh from Listing Office: Coldwell Banker Realty - Boston.

$1,679,900

3 Beds ⋅ 2 Baths ⋅ 73572791 MLS ⋅ ACTIVE Status

Distinctive in both design and craftsmanship, this custom expanded Ranch combines balanced architectural proportions, generous living space, and everyday comfort in Winchester’s highly sought-after East Hill neighborhood. A welcoming foyer with built-in bench opens to warm, light-filled interiors curated to feel both connected and intimate. At the heart of the home, the expansive mahogany kitchen features a substantial wood center island, handmade pocket plantation shutters that disappear seamlessly behind custom cabinetry, updated countertops and backsplash, a concealed illuminated bar cabinet, beverage fridge, and dual-zone wine fridge. Paned-glass pocket doors can separate the kitchen or open it to the adjoining dining and family rooms, where radiant-heated floors create a warm, inviting setting and a wall of windows connects the interior space beautifully to the surrounding landscape. The family room’s custom cherry entertainment center, finished with copper paneling and ebony inlays, reflects the extraordinary attention to detail found throughout. A formal living room with fireplace and custom millwork provides a separate space to gather or unwind. Tucked into a private wing are three well-proportioned bedrooms with hardwood floors and generous closets, along with a renovated full bath featuring a double vanity, deep soaking tub, and radiant-heated floor. The finished lower level offers remarkable flexibility with a media room wired for surround sound, exercise room, second full bath, laundry, mudroom area, abundant temperature-controlled storage, and direct access to an oversized two-car garage with workspace. Outside, the backyard and stone patio provide an equally peaceful and private extension of the interior living space. Mature plantings, stone walls, a potting shed, and an irrigation system complete this wide, one-third-acre lot. Central air, central vacuum, extensive built-ins and storage, plus new interior doors and crown molding throughout the bedroom wing add comfort and convenience. Polished, distinctive, and genuinely inviting, 5 Willowdale Road is a home of enduring quality that feels every bit as special as it looks. NO OPEN HOUSES, shown By Private Appointment only.

5 Willowdale Rd, Winchester

Listing courtesy of Listing Agent: Erica Carson from Listing Office: Coldwell Banker Realty - Lexington.

$2,049,000

4 Beds ⋅ 4 Baths ⋅ 73572687 MLS ⋅ ACTIVE Status

Thoughtfully reimagined with a designer’s eye, this beautifully renovated 4 bed, 3.5 bath home delivers refined living across 3 finished levels. Elevated finishes, including custom tile work, white oak flooring, & curated lighting set this home apart from the typical renovation. The heart of the home is a beautifully designed kitchen with an oversized island & seamless connection to the surrounding living spaces. A formal living room with fireplace, spacious den, sun-filled dining area, & inviting sunroom create an ideal layout for both everyday living & entertaining, while a first-floor bedroom & full bath offer flexibility for guests, or home office. Upstairs includes three spacious bedrooms, including a serene primary suite with spa-like bath & dual walk-in closets, plus second-floor laundry. The finished lower level expands your living space with room for a gym, playroom, or media retreat, complete with a half bath & mudroom. A turnkey home designed to fit the way you live today

26 N Gateway, Winchester

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

$1,699,000

3 Beds ⋅ 2 Baths ⋅ 73572661 MLS ⋅ ACTIVE Status

Extensively rebuilt and expanded, this impeccably maintained 3/4 Bed 2 BA home offers a spacious and versatile floor plan. The impressive 28’ x 20’ great room features vaulted ceilings, bay window, and a gas fireplace which flows nicely from the updated kitchen. Step outside to a new oversized Azek deck with plenty of room for grilling, dining, and relaxing. The main level also includes formal living and dining rooms, plus a bedroom & full bath. The formal dining room offers flexibility to serve as a fourth bedroom, if desired. Upstairs are two generously sized bedrooms with hardwood floors and ample closet space, along with a spacious hall bath featuring a skylight. Additional highlights include a finished lower level, laundry and storage areas, and direct access to a two-car garage. Beautifully landscaped grounds feature perennial gardens, flowering trees, natural stone walls, and exceptional privacy—nestled into one of Winchester’s most desired neighborhoods, all just 7 miles from Boston with convenient access to the town center, Fells trails, major routes and highways. Please see feature/ update list attached.

4 Churchill Road, Winchester

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

$1,099,000

4 Beds ⋅ 3 Baths ⋅ 73571480 MLS ⋅ ACTIVE Status

Tucked on a quiet side street just north of Main Street, this circa-1853 antique pairs the character of a classic Winchester home with the space of a beautiful, sun-filled addition (completed in 2003): A lovely farmer's porch welcomes you and, once inside, hardwood and tile floors run through the main living spaces. Front rooms include a quaint sitting room and private office. A gas fireplace adds warmth in the family room off the kitchen, which has a slider out to a generous sized deck overlooking the serene back yard. Fresh paint throughout means there is nothing to do but move in. The same addition brought two bedrooms (primary with en suite bath), a walk-in closet, and updated kitchen cabinetry. Out back, a wood deck steps down to a spacious fenced yard with a built-in tree house, a garden area, storage shed, and in-ground sprinkler system. Central air conditioning, gas heat, town water and sewer, a one-year-old hot water tank, a partially finished, heated basement, a walk-up attic, and a four-car driveway. The location is the real headline: walk to the commuter rail, the bus, and Winchester Center's shops and restaurants, with the park, bikeway, and conservation trails minutes away. Newly renovated Lynch Elementary, McCall Middle and Winchester High School.

24 Richardson St, Winchester

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

$1,050,000

5 Beds ⋅ 3 Baths ⋅ 73571418 MLS ⋅ ACTIVE Status

Situated on a large,10k+ level corner lot with frontage on both Cross Street and Verplast Avenue! The upper level features a fireplaced living room w picture window, updated kitchen, three bedrooms, 1.5 baths, and a large sunroom overlooking the expansive backyard. The first level offers additional flexible living space with a kitchenette, living area, two bedrooms, laundry, and a full bath, providing great potential for an in-law setup, guest space, home offices, or extended living. The generous lot and existing footprint create an ideal opportunity to modernize the home, expand the living space, or explore future possibilities. Put your personal touch on this home and build some great equity! This property is full of potential and ready for its next chapter!

257 Cross Street, Winchester

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

$1,098,000

3 Beds ⋅ 2 Baths ⋅ 73566405 MLS ⋅ ACTIVE Status

Welcome to 17 Russell Rd, a meticulously maintained and updated 3-bedroom, 1.5-bath home in a highly desirable Winchester neighborhood! A charming mudroom with beadboard accents and radiant heated floors welcomes you into a bright open-concept layout with gleaming hardwood floors throughout. Enjoy a sun-filled living room with cozy bow window seating, a spacious kitchen with rich cabinetry, and a dining area with sliders to a private deck and fully-fenced, tree-lined yard. Upstairs features three bedrooms, including a impressive primary suite with a stunning walk-in closet, and a full bath. Major upgrades include deleading (2018), basement asbestos removal (2019), a newer furnace, and a brand-new water heater (2024). Ideally located just 1 mile from Winchester Center, top schools, dining, and the MBTA commuter rail to Boston! Conveniently located near local schools, with easy access for families.

17 Russell Rd, Winchester

Listing courtesy of Listing Agent: Tsz Mui Kwan from Listing Office: Kwan Realty Inc..

$425,000

2 Baths ⋅ 73565929 MLS ⋅ ACTIVE Status

Exceptional location downtown at Judkin Green, directly outside the heart of Winchester Center. This bright, modern, and impeccably clean professional office offers the convenience of being right at the center of town while providing the accessibility and ease of a professional office building. Unit #32 features a welcoming reception area and waiting room, plus four individual private office spaces, creating a functional and polished environment for a variety of professional uses. Two covered parking spaces are welcomed amenity, providing convenient on-site parking for owners, employees, or clients. In addition, there is ample additional parking nearby for clients and visitors. The building also features an elevator for easy access. New heat pump in 2024. With Winchester Center's shops, restaurants, services, and commuter rail right nearby, this is a rare opportunity to own a well-appointed professional office in one of Winchester's most convenient and desirable locations.

63 Shore Rd Unit 32, Winchester

Listing courtesy of Listing Agent: Melanie Lentini from Listing Office: Leading Edge Real Estate.

$1,999,000

4 Beds ⋅ 3 Baths ⋅ 73565817 MLS ⋅ ACTIVE Status

Classic Colonial nestled within one of Winchester’s most desirable neighborhoods, offering timeless architecture, exceptional flexibility, and an enviable setting. The first floor features an updated kitchen with slider to the scenic rear yard and oversized brick patio, casual den, half bath, formal dining room, and gracious living room with fireplace and classic built-ins. Double doors lead to a spectacular all-season porch, perfectly positioned for effortless entertaining indoors or out. The second floor offers four corner bedrooms, including a spacious primary suite with double closets, ensuite bath, and convenient laundry. The walk-up third floor invites endless possibilities with an additional bedroom and abundant closet space. Approximately 500 square feet of finished lower-level flex space provides room for a home gym, teen retreat, playroom, or office. Outside, a private, level yard offers ample space for gardens, play, and entertaining, with a generous brick patio for relaxing and gathering. The two-car heated garage features a full walk-up second floor, ideal for storage or future finishing as a studio, office, or home-away-from-home retreat. Simply a beautiful home in an exceptional location—ready to be loved from day one.

85 High St, Winchester

Listing courtesy of Listing Agent: Catherine Albiani from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.

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