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Newest Homes for Sale in Winchester, MA

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Welcome to your dedicated resource for newest homes for sale in Winchester, MA. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As a local Winchester, MA agent, Marc Fiore specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the newest properties currently available below, or contact a local agent to discuss the details that matters most to your search.

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All Newest Homes for Sale in Winchester, MA

465 Washington Street Unit 465, Winchester
$1,250,000
4 Beds ⋅ 3 Baths ⋅ 73574929 MLS ⋅ ACTIVE Status
Refined, low-maintenance living with the scale, finishes, and lifestyle advantages rarely found at this price point. This 4-bedroom, 3-bath townhouse (built in 2017) features open-concept design and high-end finishes. The main living area is anchored by a designer chef’s kitchen with premium appliances and a large island that flows to a large living room with a gas fireplace. The primary suite is a true oasis with a walk-in closet, spa bath, and a private balcony for evening relaxation. 3 other bedrooms, a refined bath plus second floor laundry provide flexibility for family, guests, or home office needs. The lower level is versatile, perfect for a media room and home gym. Convenience & Amenities: Enjoy a private, fenced backyard, dining patio, EV charger, and premium parking. Quick access to the Fells, major routes, plus close to top schools, parks, and the town center for an easy downtown commute. A rare turn-key value, bigger and better than most single families at this price.

465 Washington Street Unit 465, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Gibson Sotheby's International Realty.
37 Mayflower Road, Winchester
$3,149,000
7 Beds ⋅ 8 Baths ⋅ 73573670 MLS ⋅ ACTIVE Status
Magnificent newer sun-filled Colonial ideally situated in a premier West Side cul-de-sac, offering over 8,000 sq ft of beautifully finished living space across four levels-A great price at only $368psf! !Designed for grand-scale entertaining and multi-generational living, this exceptional home features 7 bedrooms, 7.5 baths, four fireplaces and a 3-car direct-entry garage, all complemented by custom built-ins, fine cabinetry and beautiful millwork throughout. The newly renovated chef’s kitchen showcases quartz countertops, an oversized center island, two dishwashers and a butler’s pantry with wine fridge and ice maker, flowing seamlessly into the elegant dining room, living room and fireplaced family room overlooking the meticulously maintained grounds. A dedicated first-floor wing offers incredible flexibility for extended family, au pair or guests, while a private office with custom wet bar and additional spaces can easily accommodate two executive home offices. Upstairs, the grand primary suite is joined by four additional bedroom suites, each offering a private bath, sitting area and generous closet space. The third floor provides a completely private guest or teen suite with a full bath and two closets.The finished lower-level offers media, game and gym areas with a full bath and direct access to the inviting heated pool and lush landscaped grounds. Unmatched in scale and versatility with resort-like amenities, exceptional craftsmanship and a coveted West Side location, this remarkable home offers luxury living at its finest.

37 Mayflower Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
117 Highland, Winchester
$1,650,000
5 Beds ⋅ 4 Baths ⋅ 73573887 MLS ⋅ ACTIVE Status
Expansive living and unparalleled curb appeal define this exceptional five-bedroom garrison colonial, ideally positioned near the natural beauty and extensive trails of the Fells Reservation. Set in the highly regarded Muraco Elementary School district, this spacious home offers an inviting blend of timeless architecture, thoughtful updates, and remarkable flexibility for today’s lifestyle. The sun-filled first floor features an open, seamless flow designed for both everyday living and effortless entertaining. A thoughtfully appointed eat-in kitchen with premium Sub-Zero and Fisher & Paykel appliances opens to the dining space, creating an ideal setting for gathering. A wood-burning fireplace anchors the living room where you can watch the world go by from the gorgeous picture window. A home office, mudroom, and powder room add functionality to this level. Upstairs, the generous primary suite includes a full bath and convenient laundry, with tree-top views from the Juliet balcony, complemented by four additional bedrooms and a family bath. A finished walk-up attic provides valuable storage and flexible bonus space, while the finished lower level adds a generous family room and several bonus spaces ideal for a second home office, playroom, media space, or additional recreation area, with kitchenette and full bath allowing for ADU possibilities. Outside, enjoy a truly private retreat with a fully fenced yard and pristine in-ground pool, offering exceptional space for outdoor living, entertaining, and relaxation. A two-car attached garage adds everyday convenience. With generous proportions throughout, multiple flexible spaces, an inviting open floor plan, and close proximity to the Fells Reservation, this Winchester Highlands property offers a rare opportunity to enjoy space, privacy, and sophisticated everyday living in one of Winchester’s desirable neighborhoods.

117 Highland, Winchester

Listing courtesy of Listing Agent: Dara Singleton from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
19 Hancock Street, Winchester
$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.
17 Churchill Rd, Winchester
$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.
60 Lake St Unit E, Winchester
$660,000
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.
4 Churchill Road, Winchester
$1,599,000
4 Beds ⋅ 2 Baths ⋅ 73572661 MLS ⋅ ACTIVE Status
Price Change!! **Open House this weekend or call for private showings** Great offering~ Extensively rebuilt and expanded, this impeccably maintained 4 Bed 2 BA home offers a spacious and versatile floor plan. The impressive 28’ x 20’ great room w/living area and dining area 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 room w/ fplc, plus 2 spacious bedrooms & full bath. offering flexibility for various uses. Upstairs are two additional generously sized bedrooms with hardwood floors and ample closet space, along with a full 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.
24 Richardson St, Winchester
$1,049,000
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.
257 Cross Street, Winchester
$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.
17 Russell Rd, Winchester
$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.AI-generated virtual staging. Furniture and decor are digitally added for illustration purposes only.

17 Russell Rd, Winchester

Listing courtesy of Listing Agent: Tsz Mui Kwan from Listing Office: Kwan Realty Inc..
85 High St, Winchester
$1,899,000
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.
54 Squire Road, Winchester
$2,399,000
4 Beds ⋅ 5 Baths ⋅ 73555666 MLS ⋅ ACTIVE Status
Introducing 54 Squire Road,an exceptional newer Colonial privately sited within one of Winchester’s most desirable enclaves.Set on a beautifully landscaped, wooded lot, this sun-filled residence blends timeless architecture with numerous substantial owner upgrades.Highlights include 9’ ceilings, elegant millwork,a designer chef’s kitchen with premium appliances,an impressive family room with custom built-ins and entertaining bar,formal dining with butler’s pantry, private office,and luxurious primary suite with vaulted ceilings, walk-in closets,and spa bath.Expanded outdoor living features a custom outdoor kitchen,fire pit,and multiple patios designed for exceptional entertaining.The finished lower level offers a bonus room, home gym, mudroom, and oversized 2-car garage.Professionally landscaped with exceptional privacy, yet just moments to the Vinson-Owen School,steps to the Swim & Tennis Club,and major commuter routes.A rare opportunity to own one of Winchester’s finest newer homes. See Video: https://player.vimeo.com/progressive_redirect/playback/1217669935/rendition/1080p/file.mp4%20%281080p%29.mp4?loc=external&log_user=0&signature=65fb6c1e2692e9ac8d5b781ceed13c02239d5128d88af87ce725ce6cd7907704

54 Squire Road, Winchester

Listing courtesy of Listing Agent: Anthony Marino from Listing Office: The Marino Group Collection.
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