About Hot on the Market in Winchester!

Below you will find listings hot on the market in Winchester, Massachusetts! All of these listing have been on the market for 7 days or less. For other listings “hot on the market” in other communities, visit our “Communities” page. Don’t see your town listed? Contact us directly to get the latest info!

8 Chestnut St Winchester, MA 01890

$3,299,000 - 5Br/6Ba -  for Sale in Winchester
Open House
$3,299,000
5 Beds
6 Baths
5,366 SqFt
Status Active
MLS # 73305360
Property Type Single Family Residence
Price Type --
This iconic vintage farmhouse seamlessly blends historic charm with modern luxury. Spanning over 5,366 sq. ft., this home has been completely renovated and thoughtfully expanded for today’s lifestyle. Featuring 5 bedrooms, 4 full and 2 half baths, every inch exudes elegance and comfort. The designer kitchen is a chef’s dream, with high-end appliances, a beverage bar, and a large center island that flows into the open-concept living and dining areas—perfect for entertaining. The spacious primary suite boasts a walk-in closet and a magazine-worthy en-suite bath. Stunning light fixtures throughout add a sophisticated touch. Outside, professional landscaping creates a serene oasis, complete with a cozy fire pit for year-round enjoyment. Nestled in a prime location, this home offers unmatched convenience to Winchester Center, top-rated schools, dining, shopping, The Fells, and more. Don’t miss this rare chance to own a piece of Winchester’s history with all the modern amenities!

15 Churchill Road Winchester, MA 01890

$2,699,000
4 Beds
4.5 Baths
5,501 SqFt
Status Active
MLS # 73298854
Property Type Single Family Residence
Price Type --
Indulge in modern luxury with this 2024 masterpiece, set on a double 1/2 acre lot. This 4 bedroom, 4.5-bathroom home seamlessly blends chic style with an abundance of functional space. The architectural design is dramatic, showcasing soaring ceilings, a stunning contemporary fireplace, state of the art kitchen & sun filled living room which opens to a fabulous deck, creating a perfect indoor-outdoor space. The gourmet kitchen features a sleek design w/ a large island, high end appliances, & stylish open shelving. Upstairs, the lavish primary suite features a spa like bath & large custom closet. The 3 additional bedrooms offer ensuite baths. The walk out LL family room w/ wet bar is the perfect space to unwind. This property also features a 2 gar attached garage, mud room, office & laundry room. The double lot offers many possibilities ~ level w/ patio. This home is located near conservation trails, top-rated schools & Boston offering a lifestyle of convenience, luxury & tranquility!

50 Winford Way Winchester, MA 01890

$2,599,000
5 Beds
4.5 Baths
4,270 SqFt
Status Active
MLS # 73288818
Property Type Single Family Residence
Price Type --
Stunning new construction! Energy star rated, high efficiency 5 bed 4.5 bath home perfectly situated in a prime East Side location! The first floor welcomes you w/ an open, airy layout, featuring a stylish mudroom, pantry, bath & home office. The gourmet, high-end kitchen flows seamlessly into the living room, complete w/ a cozy fireplace; the dining area extends out to a deck, overlooking a beautifully landscaped yard & patio. The second floor boasts four spacious bedrooms & three full baths, including a lavish primary suite w/ a spa like bathroom. A well-appointed laundry room is also conveniently located on this floor. The third-floor suite is a true retreat, offering two versatile rooms ideal for extended family, office, or lounge, complete w/ a wet bar, an oversized bath & a 5th bedroom with abundant closet space. The expansive lower level adds even more living space, featuring a large family room and an additional full bath, perfect for entertaining. This home truly has it all

7 Wainwright Rd Unit 22 Winchester, MA 01890

$1,495,000 - 2Br/3Ba -  for Sale in Winchester
Open House
$1,495,000
2 Beds
2.5 Baths
3,350 SqFt
Status Active
MLS # 73274235
Property Type Condominium
Price Type --
Now is the time to make a move! Step into a sophisticated lifestyle as you enter through a charming courtyard into this elegant condo. The beautifully updated kitchen is a standout, featuring granite countertops, cherry cabinetry, and premium new stainless steel appliances—a chef’s dream come true. The open-concept layout is perfect for modern living, with a dining area flowing into the inviting living room. Custom built-ins, a soaring ceiling with skylights, and a spacious deck overlooking a serene creek and vibrant wildlife complete this picture of luxury and tranquility. The first-floor primary suite offers the convenience you’ve been looking for, with a walk-in closet and a spa-like en-suite bath. Upstairs, enjoy a flexible floor plan with a versatile den/bedroom, another bedroom, a full bath, and a loft boasting custom cabinetry. The expansive lower level adds even more space with a family room, walkout access, a private office/flex space, and a generous walk-in closet.

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