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!

56 Salisbury St Winchester, MA 01890

$2,890,000
4 Beds
3.5 Baths
4,212 SqFt
Status Active Under Contract
MLS # 73290646
Property Type Single Family Residence
Price Type --
Beautifully renovated 4 bedroom home in sought after Winchester Flats! Featuring a picturesque combination of stylish comfort and modern design. The 1st floor welcomes with an oversized custom mudroom leading to a spacious chef's kitchen featuring upgraded Wolf appliances including gas range, steam oven, and 2 built-in beverage fridges. The family room invites with custom built-in window seats, vaulted ceiling, and a scenic view of the manicured yard. The dining room impresses with show-stopping wallpaper and wainscoting, while the chic living room and home office with built-in desks create a space for all occasions.The 2nd floor features a beautiful primary suite with walk-in closet and ensuite bath with dual vanity, while 3 more spacious bedrooms, 2 full bathrooms, and laundry room provide the ideal set up for family living. The finished lower level boasts additional living space and ample storage, and outside enjoy the ease of a 2 car garage, large yard, and long driveway. Must see!

6 Lakeview Road Winchester, MA 01890

$3,895,000 - 5Br/5Ba -  for Sale in Lakeview/ Ravenscroft, Winchester
Open House
$3,895,000
5 Beds
4.5 Baths
5,768 SqFt
Status Active
MLS # 73290640
Property Type Single Family Residence
Price Type --
Experience the epitome of luxury living in this exceptional, high-end renovation of a breathtaking Winchester gem, located in one of the town’s most coveted neighborhoods. Enjoy stunning lake views from numerous rooms & the expansive 1000SF deck! Reconstructed and designed by RENEW, a company committed to blending historical integrity with modern amenities, paying meticulous attention to every detail. This home boasts a new floor plan w/ fabulous kitchen featuring a LaCornue 5 burner stove, 9' Calacatta marble island & fplc w/ adj family rm. 5 spacious bedrooms & 4.5 baths, including a magnificent primary suite w/ marble turret shower. The finished lower level offers a custom wine cellar, perfect for entertaining w/direct entry access to yard. Showcasing hand-picked and crafted specialty items that cannot be found in new builds. 3-car attached garage, & close proximity to Winchester's town center, the commuter train to Boston, Mystic Lakes beach, playgrounds & scenic walking trails.

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

27 Everett Ave Winchester, MA 01890

$3,899,999
6 Beds
5.5 Baths
7,431 SqFt
Status Active
MLS # 73287578
Property Type Single Family Residence
Price Type --
This is one of the most notable and distinguished homes on Everett Avenue, with preeminent siting on more than half an acre. Designed by famous architect Robert Coit, this residence combines the magnificence of early 1900s architecture with today's modern amenities. Completely renovated in 2023/2024, this residence features hallmark architectural details including Tudor-style balusters, high ceilings, and a beautiful floor plan centered with a large entrance hall. Large-scale rooms, coffered ceilings, original crown moldings, mantels, and decorative trim are enhanced by the beauty of restored hardwood floors. The brand-new kitchen is a chef's dream with a walk-in pantry w/laundry and refrigerator drawers plus a butler's pantry with a wine fridge. Floor-to-ceiling windows flank the huge family room, overlooking park-like flat grounds. The huge lawn is one of the biggest you can find. Magnificent old oak trees, beautiful birches, and an ample driveway grace this legacy residence.

27 Cabot St Winchester, MA 01890

$3,200,000
4 Beds
5 Baths
4,215 SqFt
Status Active
MLS # 73287473
Property Type Single Family Residence
Price Type --
Meticulously renovated home in desirable Winchester Flats! Set on a tranquil corner lot surrounded by mature trees, less than a mile from schools, Winchester Center, and commuter rail, this exquisite four-level Tudor offers the perfect blend of modern elegance and classic charm. The main level showcases 2 inviting family rooms adorned with fireplace and integrated sound system, gourmet kitchen with Wolf and Subzero appliances, peaceful 3-season porch, and thoughtfully designed mudroom. Ascend to the 2nd floor to discover the primary suite, a peaceful sanctuary featuring a fireplace, cozy sitting area, custom walk-in closet, and ensuite bathroom with dual sinks and zero-entry shower. 2 additional bedrooms with shared bathroom provide ample accommodations for guests or family members, while the 3rd floor offers a private retreat with spacious bedroom and luxurious bathroom with soaking tub. The finished lower level is ideally set up to be used as media room/family room/gym. A must see!

18 Goodwin Drive Unit 39 Woburn, MA 01801

$1,282,460 - 3Br/3Ba -  for Sale in Woburn
Open House
$1,282,460
3 Beds
2.5 Baths
2,300 SqFt
Status Active
MLS # 73286601
Property Type Condominium
Price Type --
New construction in Woburn at Highland at Vale! The Southbrook is a beautiful townhome with open-flowing rooms and an abundance of natural light. The large kitchen, gathering room and private deck are perfect for entertaining guests. This plan features a convenient first-floor Owner's Suite with an attached spa-like bath for a relaxing escape. On the second floor you'll find a spacious loft with 2 guest bedrooms, walk-in closets, and a full bath. Just 12 miles to Boston as well as various options for local dining and entertainment. The innovative floor plan along with the unbeatable location makes this the perfect home! New hillside community and neighborhood with amazing views.

25 Ledgewood Rd Winchester, MA 01890

$3,599,000
5 Beds
4.5 Baths
5,500 SqFt
Status Active
MLS # 73283741
Property Type Single Family Residence
Price Type --
Nestled on 1.1 acres in Winchester, this fully custom renovated home is truly a hidden gem. The property is well secluded from the main road, offering a tranquil retreat. Transformed in 2024, this home features 5 spacious beds, 4.5 baths and custom spaces throughout. The grand kitchen, with white oak accents, is a culinary centerpiece. The light-filled family room has expansive windows and a custom marble gas fireplace. A dual sided wood-burning fireplace connects the study and living room. The upstairs study, perfect for office or homework area, has custom built ins. The rec room includes quartz counters and a beverage fridge, ideal for a media room. The primary suite offers a generous walk in closet space and a luxurious bath with dual opposing vanities and a stunning dolomite marble shower. Landscaping features an expansive bluestone patio and thoughtful organic plantings. This rare home is truly an exceptional work of art!

16 Goodwin Drive Unit 40 Woburn, MA 01801

$1,282,460
3 Beds
2.5 Baths
2,300 SqFt
Status Active
MLS # 73281769
Property Type Condominium
Price Type --
New construction in Woburn at Highland at Vale! The Southbrook is a beautiful townhome with open-flowing rooms and an abundance of natural light. The large kitchen, gathering room and private deck are perfect for entertaining guests. This plan features a convenient first-floor Owner's Suite with an attached spa-like bath for a relaxing escape. On the second floor you'll find a spacious loft with 2 guest bedrooms, walk-in closets, and a full bath. Just 12 miles to Boston as well as various options for local dining and entertainment. The innovative floor plan along with the unbeatable location makes this the perfect home! New hillside community and neighborhood with amazing views. This home built just for you is slated for completion summer 2025.

20 Hancock St Unit 20 Winchester, MA 01890

$679,900
3 Beds
1.5 Baths
1,752 SqFt
Status Active
MLS # 73279548
Property Type Condominium
Price Type --
Welcome to Winchester ! This townhouse with large shared backyard is located on lovely tree lined street . The front porch welcomes you as you can sit and watch the world go by. First floor has living room, dining room and kitchen with laundry. Half bath completes the first floor. Three bedrooms and full bath upstairs. One bedroom is a pass through. Back stairway to half of full size attic is off the kitchen. Basement stairs are located off the back entry to full sized unfinished basement. Property being offered as is. Shared driveway, parking off street in back and large fenced lawn also shared with neighbor. Great location close to schools, commuter line and downtown.

92 Hillcrest Pkwy Winchester, MA 01890

$2,499,999 - 5Br/5Ba -  for Sale in Winchester
Open House
$2,499,999
5 Beds
4.5 Baths
4,048 SqFt
Status Active
MLS # 73279517
Property Type Single Family Residence
Price Type --
This exquisite, custom-built home from local master builder boasts a grand two-story foyer, a spacious chef's kitchen seamlessly flows into a vaulted ceiling family room, & an open concept living room & dining room perfect for entertaining. Upstairs, discover a luxurious primary bedroom suite w/expansive walk-in closet & a primary bath featuring double vanities, jacuzzi tub, & a large tiled shower. Two additional well-appointed bedrooms and bathroom complete the 2nd floor, while the 3rd floor offers expansive living w/two ensuite bedrooms, each with a full bath and walk-in closet. Enjoy the high ceilings, detailed custom woodwork, and elegant trim throughout. Additional amenities include central air, central vacuum, deck, & a spacious three-car garage. This stunning home epitomizes elegance and functionality in a prime Winchester location. Nestled near the scenic Fells reservation for outdoor enjoyment & vibrant Winchester center with it's restaurants, shops, farmer's market and more!

6 Stratton Drive Unit 3308 Woburn, MA 01801

$898,905 - 2Br/2Ba -  for Sale in Woburn
Open House
$898,905
2 Beds
2 Baths
1,425 SqFt
Status Active
MLS # 73278163
Property Type Condominium
Price Type --
Brand new condos at Highland at Vale in Woburn! The Hayden is built to impress. Make a delicious meal in the stunning kitchen featuring a large island, stainless steel appliances, and an abundance of cabinet space. Spend time with friends and family in the private dining room or spacious gathering room flooded with natural light from the private balcony. Turn the flex space into a quiet office or den. Owner's can escape to their private suite with large walk-in closet and spa-like bath attached. The second bed and bath make the perfect space for guests. Conveniently located near local dining, shopping, and entertainment.

28 Thornberry Road Winchester, MA 01890

$1,449,000 - 4Br/2Ba -  for Sale in Winchester
Open House
$1,449,000
4 Beds
2 Baths
2,245 SqFt
Status Active
MLS # 73274439
Property Type Single Family Residence
Price Type --
Best priced single family home in Winchester! Located in the highly sought-after West Side. Situated on .34 acres, this home has been fully remodeled and is ready for its new owner. The home features four bedrooms plus a bonus room that works perfectly as an office or exercise room, and two full bathrooms. Since the home sits high above the road, you can enjoy complete privacy in your open-concept living, dining, kitchen, and family room spaces. The kitchen features all brand-new appliances as well as quartz countertops. Directly off of the living room, you have a generous-sized, peaceful balcony overlooking your front yard - perfect for coffee in the mornings, or unwinding after a long day at work. Off of the family room to the back of the house, you have a tranquil outdoor patio area. New roof, upgraded electrical and all new windows - this home needs nothing. Get into one of Winchester's top neighborhoods before the school year starts!

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