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!

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37 Dix St Winchester, MA 01890

$1,699,000 - 7Br/3Ba -  for Sale in Winchester
Open House
New
$1,699,000
7 Beds
2.5 Baths
3,835 SqFt
Status New
MLS # 72734035
Property Type Single Family
Price Type --
Location, Location, Location! This timeless 7 bedroom, 2 & 1/2 bath home is situated just steps from Winchester center! A stately colonial revival home, 37 Dix features gorgeous period detailing and abundant natural light. The inviting front porch welcomes you into a wide foyer. You'll enjoy both a sitting room & formal living room w/fireplace, at the front of the home. The dining room leads you into a renovated, eat-in kitchen with stainless appliances & granite counters. A sun-filled office & half bath complete the first floor. Upstairs you'll find four bedrooms, including a master suite w/ private bath. There's even more space! A fully finished 3rd floor offers three more bedrooms, inviting you to create your perfect bonus spaces. Updates include new electrical, high efficiency gas furnace and appliances. Outdoor space boasts a new patio. Don't miss this chance to own a spacious, elegant home in walking distance to shops, restaurants & easy commuter travel to Boston!

16 Pepper Hill Dr Winchester, MA 01890

$1,299,000 - 5Br/4Ba -  for Sale in Winchester
Open House
New
$1,299,000
5 Beds
3.5 Baths
3,069 SqFt
Status New
MLS # 72734103
Property Type Single Family
Price Type --
Looking for an updated, spacious home in a desirable neighborhood close to Wright-Locke farm and Mullen field? Look no further than 16 Pepper Hill Drive! This 5 bedroom, 3 & ½ bath home has all the amenities today’s buyers desire. The renovated kitchen boasts stainless steel appliances, custom cabinetry & granite counters. The living room features a gas fireplace and large built-in shelves. Upstairs, you’ll enjoy a private master suite w/ dual-sink bathroom & walk-in closet. Three more bedrooms and another full bath complete the upper level. The home’s two car, attached garage opens into the spacious mudroom, leading into a finished lower level. You’ll love the home theatre, including built in projector and screen, in the bonus room! This level also features another full bath and leads out into a private patio with pergola. Upstairs, you’ll enjoy views from two decks as well. You simply must see all the thoughtful touches and unexpected details of this beautiful home!

49 Yale St Winchester, MA 01890

$1,999,000 - 5Br/4Ba -  for Sale in Winchester
New
$1,999,000
5 Beds
3.5 Baths
4,165 SqFt
Status New
MLS # 72733734
Property Type Single Family
Price Type --
Gracious 1920 center entrance colonial located in the desirable Wedgemere neighborhood. This home is lovingly maintained and updated and is move in condition with newer kitchen and baths.Lovely front to back fireplace living room and family room with patio views. Large dining room with built ins. Master suite has fireplace and expansive walk in closet.Master bath has jacuzzi and a walk in shower. Two additional bedrooms on second floor.Two good size bedrooms and an office area are on the third floor. Finished recreation room in the basement. Rear yard is lovely, well landscaped and private. You will be amazed at the three car garage with additional room for yoga, gym or office to mention just a few options. In addition there is a large fully floored loft area above. Bathroom is also on site and just needs to be hooked up. Live close to town and train and enjoy this beautiful house in the Flats

36 Hollywood Road Winchester, MA 01890

$1,399,000 - 4Br/4Ba -  for Sale in Winchester
Open House
New
$1,399,000
4 Beds
3.5 Baths
2,967 SqFt
Status New
MLS # 72733943
Property Type Single Family
Price Type --
Welcome Home! This traditional center entrance colonial is nestled on a cul-de-sac in the desirable East Hill neighborhood & Lincoln school district. You’re sure to love this location so close to Winchester Center, Commuter Rail, Middlesex Fells trails, schools, & easy access to Rt. 93. With the perfect blend of inviting charm & fantastic location, this sun-filled home features a spacious eat-in kitchen which opens into a large family room w/ access to a private deck, perfect for outdoor entertaining. First floor also features an entertaining sized dining room & front to back fireplaced living room which leads to a private screened in porch overlooking mature plantings. Second floor offers 4 corner bedrooms, family bath & a master suite w/ plenty of closet space. Beautifully renovated lower level includes a recreation room w/ a walk-in closet, a bonus room, perfect for a home office, & a bathroom. Spacious yard complete with new shed & secret side garden. Don't miss out!

41 Amberwood Dr Winchester, MA 01890

$1,699,000 - 5Br/5Ba -  for Sale in Winchester
Open House
$1,699,000
5 Beds
4.5 Baths
3,876 SqFt
Status Active
MLS # 72732761
Property Type Single Family
Price Type --
If you are looking for one-level living with a sprawling open floor plan, look no further! Perched almost above the tree line, you’ll enjoy ultimate privacy and magnificent seasonal views from nearly every window. The kitchen features cherry cabinets, Sub-Zero refrigerator, two Miele dishwashers, double ovens and granite countertops & center island. You’ll love the completely open feel of the living area surrounding the kitchen, including an eat-in dinette, sun-filled dining room with vaulted ceiling & inlaid floors, and adjoining family room with wood burning fireplace—all perfect for entertaining. Four bedrooms on the main level offer three full & one half bathrooms in addition to a master suite with another fireplace with plenty of closet space. The spacious lower level features a large media room with stone fireplace, additional bedroom & another full bath. Step outside and enjoy sunset views from your spacious private, newly constructed patio. Walking distance to VO schools!

122 Cambridge Street Winchester, MA 01890

$1,599,000
5 Beds
3.5 Baths
3,239 SqFt
Status Active
MLS # 72732371
Property Type Single Family
Price Type --
This timeless, mansard style home with unsurpassed curb appeal features a spacious 3,239 sqft of living space, 10ft ceilings, elegant rooms and warm casual spaces. The easy flow of the first floor is perfect for everyday living and entertaining. Cozy up by the fireplace in the living room. Enjoy the newly renovated kitchen with striking quartz countertops, stainless steel appliances and center island that opens up into the large dining room. A family room, mudroom, ½ bath, private study, expansive yard and 2 car garage complete the first floor. Upstairs, you’ll love the master suite with renovated bath & walk-in closet, along with four add'l bedrooms, laundry room and two updated full baths. Large, unfinished basement with ample storage space. Impeccably landscaped corner lot with fenced-in backyard and bluestone patio. Desirable eastside neighborhood, steps to Ambrose Elementary, Winchester Boat Club and Country Club. Easy stroll to all that Winchester Center has to offer. A must see!

2 Pine Street Winchester, MA 01890

$1,649,000
6 Beds
3.5 Baths
4,034 SqFt
Status Active
MLS # 72732071
Property Type Single Family
Price Type --
Welcome to 2 Pine Street, originally known as the Conant house. Don't miss this once in a lifetime opportunity to own one of Winchester's most iconic properties situated just outside the town center! Zoned as a two family, this majestic Colonial & Italianate revival-style home can also be reconfigured as a gorgeously ornate family home by itself or with an already existing apartment, perfect for an in-law or au pair suite. Inside the home, you'll immediately notice the incredible craftsmanship throughout, including soaring ceilings, leaded glass windows, fireplace & period detailing. Perhaps the most special bonus to this property is its large barn, an incredible piece of living history! Formerly a working barn for horses, this generous space could accommodate multiple vehicles & includes a vast upstairs area, ready for imaginative renovation ideas. Located in walking distance to everything Winchester has to offer! This one-of-a-kind home is truly one of Winchester's finest gems!

71 Wildwood St Winchester, MA 01890

$2,089,000
5 Beds
3.5 Baths
4,653 SqFt
Status Contingent
MLS # 72732493
Property Type Single Family
Price Type --
Timeless center entrance brick colonial in the heart of Winchester’s Flats neighborhood! Upon entering this expansive home, you’re immediately immersed in period architectural detail. From the sweeping staircase of the two-story foyer your eye is drawn to the exquisite dentil molding & custom woodwork. Sprawling 1st floor features traditional, comfortable & functional spaces for today’s lifestyles- newly updated quartz & stainless kitchen, mudroom, formal dining room, large living room w/ fireplace, wood-paneled home office & cozy fireplaced den. Sun-drenched family room opens to a lovely bluestone patio. 2nd floor features master suite w/ full bath & walk-in-closet, 3 addl bedrooms & full bath. Private 5th bedroom suite w/ full bath & separate staircase. Lower level has play room, exercise room, wet bar. Vacation in your own backyard oasis featuring a spectacular pool, outdoor shower, fenced yard, and bluestone patios overlooking beautiful gardens. View this one-of-a-kind home today!