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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

85 High Street, Winchester
$1,899,000
4 Beds ⋅ 3 Baths ⋅ 73596915 MLS ⋅ NEW Status
Discover the possibilities to make your home, Yours. Classic Colonial nestled within one of Winchester’s most desirable neighborhoods, offering timeless architecture, exceptional flexibility, within a rare 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 Street, Winchester

Listing courtesy of Listing Agent: Catherine Albiani from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
3 Sunset Road, Winchester
$1,699,000
4 Beds ⋅ 3 Baths ⋅ 73596720 MLS ⋅ NEW Status
Welcome to 3 Sunset Road, a beautifully updated 4 BR 2.5 bath colonial with rear addition featuring a 1st floor primary option, a fabulous great room w/vaulted ceilings, and a versatile floor plan! This beautiful home is situated on a generous 1/2 acre lot in one of Winchester’s most loved neighborhoods! The large renovated kitchen with custom cabinetry & high end appliances offers plenty of room for storage, cooking and gathering and opens to a lovely dining room w/ easy access to an expansive deck overlooking the gorgeous back yard, perfect for indoor and outdoor entertaining. A warm and inviting living room features a wood-burning fireplace, while the impressive family room with soaring vaulted ceilings provides an incredible space to gather. The luxurious primary suite offers a spacious bath with double vanities, a walk-in closet, and a private sunroom, ideal for a home office, gym, or quiet retreat. Three additional bedrooms and a full updated bath complete the second level. The finished lower-level playroom offers even more flexible living space. Outside, the expansive, private backyard is truly special, offering endless possibilities for kids play, gardening, entertaining, relaxing. A wonderful opportunity to move right in and enjoy spacious living in a fantastic Winchester location, convenient to schools, shops, restaurants, and all that Winchester has to offer!

3 Sunset Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
28 Olive St, Winchester
$1,049,900
3 Beds ⋅ 2 Baths ⋅ 73595417 MLS ⋅ ACTIVE Status
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. 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.
5 Forest Cir, Winchester
$2,999,000
5 Beds ⋅ 5 Baths ⋅ 73594545 MLS ⋅ ACTIVE Status
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.
18 Middlesex St, Winchester
$2,650,000
4 Beds ⋅ 5 Baths ⋅ 73593868 MLS ⋅ ACTIVE Status
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.
15 Foxcroft Rd, Winchester
$3,799,000
8 Beds ⋅ 6 Baths ⋅ 73593484 MLS ⋅ ACTIVE Status
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.
18 Surrey Road, Winchester
$2,950,000
6 Beds ⋅ 4 Baths ⋅ 73592433 MLS ⋅ ACTIVE Status
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..
80 Nelson St, Winchester
$890,000
2 Beds ⋅ 1 Baths ⋅ 73591108 MLS ⋅ ACTIVE Status
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.
6 Aricia Ln, Winchester
$1,399,000
3 Beds ⋅ 3 Baths ⋅ 73590311 MLS ⋅ ACTIVE Status
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.
21 Amberwood Dr, Winchester
$1,999,000
5 Beds ⋅ 4 Baths ⋅ 73588059 MLS ⋅ ACTIVE Status
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.
20 Arthur St Unit 20, Winchester
$329,900
2 Beds ⋅ 1 Baths ⋅ 73587970 MLS ⋅ ACTIVE Status
Property to be sold in as is condition. This unit is subject to the Winchester Housing Corp resale procedures. See document section for additional details. Buyer is responsible for any and all inspections needed for the sale of this unit. This unit is vacant and easy to show. See attachment for qualification calculations.

20 Arthur St Unit 20, Winchester

Listing courtesy of Listing Agent: Dan O'Connell Sr from Listing Office: LAER Realty Partners.
39 Henry Street, Winchester
$850,000
3 Beds ⋅ 1 Baths ⋅ 73585414 MLS ⋅ ACTIVE Status
Exceptional Winchester living awaits at this charming 3-bedroom ranch in the coveted Vinson-Owen district! Offering 1,313 sq. ft. of bright, comfortable space plus basement expansion potential, this home features a classic fireplace living room, formal dining, and a wonderful kitchen. Step outside to a sprawling deck and a lush, private backyard that feels like your own private retreat. Complete with a 2020 roof and 2023 electrical panel, this gem is ready to welcome its next chapter!

39 Henry Street, Winchester

Listing courtesy of Listing Agent: Kelly Batti from Listing Office: Coldwell Banker Realty - Belmont.
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