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!

4 Ridgefield Rd Winchester, MA 01890

$1,599,000 - 6Br/4Ba -  for Sale in Winchester
Open House
New
$1,599,000
6 Beds
3.5 Baths
3,073 SqFt
Status New
MLS # 72816242
Property Type Single Family
Price Type --
Welcome home to this stately 1908 Colonial Revival in Winchester’s desirable Symme’s Corner. Where location is everything, this elegant home is convenient to town center, shopping, restaurants, and Wedgemere station. Raised oversized front porch overlooks a canopy of trees. A classically designed home boasting period details combined with modern touches makes this a perfect home for entertaining. Formal living and family room each have fireplaces with beautiful architectural woodwork.Three season screened porch extends as additional indoor/outdoor living space. Updated kitchen with stainless steel appliances & plenty of storage with access to an outdoor patio. Second floor features a spacious master bedroom with en-suite bathroom and a dressing room. Three additional bedrooms with a full bathroom complete the 2nd level. Third level includes two additional bedrooms, a full bathroom and an extra bonus room! 2 car garage with ample storage in the lower level. Ambrose school district!

3 Wilson St Winchester, MA 01890

$1,199,000 - 4Br/3Ba -  for Sale in Winchester
Open House
New
$1,199,000
4 Beds
2.5 Baths
2,308 SqFt
Status New
MLS # 72814940
Property Type Single Family
Price Type --
Nestled on this quiet dead end street, is an impressive Colonial that boasts four bedrooms and two and a half baths. Enjoy the serenity of the Winchester Highlands area with close proximity to the Fells Reservation and popular school districts, Winchester Center with quaint shops, restaurants and commuter rail. This formal home is spacious with lots of entertaining space. Combination family and living room featuring a fireplace, built-ins and just adjacent to the dining room. Gleaming hardwood floors throughout! Airy open concept kitchen with lots of natural sunlight. A cozy sitting room featuring a stained glass window, half bath, and access to an oversized backyard and patio. Second level has a large master suite with en-suite bathroom and walk-in closet. Three additional bedrooms, a full bathroom with laundry complete the second level. 2 Car detached garage with lots of off-street parking! This is a rare opportunity to own a home off of Highland Ave!

5 Squanto Rd Winchester, MA 01890

$1,499,000 - 4Br/3Ba -  for Sale in Winchester
Open House
New
$1,499,000
4 Beds
3 Baths
2,918 SqFt
Status New
MLS # 72815003
Property Type Single Family
Price Type --
Rare opportunity to own a charming center entrance Colonial located in desirable Ambrose School district! This pristine & spacious home features 4 bedrooms with 3 full bathrooms. Many cosmetic updates and a recently renovated chef’s kitchen! Formal dining room w/ fireplace, custom built-ins & hardwood floors throughout. French doors open to a cozy family room perfect for movie watching! The renovated kitchen is every cook and entertainer’s dream! Open to the living room and with plenty of natural sunlight. Custom cabinetry, granite countertops, gas cooking and stainless steel appliances. Exterior door opens to deck great for barbequing & leads to a fully fenced backyard. Full bathroom & laundry complete first level living. Master bedroom w/ renovated en-suite bathroom. Three additional bedrooms with a full bathroom complete the second level. Fully finished lower level with bonus room perfect for a home office/gym/zoom room & additional media room with fireplace. Welcome to Winchester!

31 Myopia Rd Winchester, MA 01890

$1,575,000 - 4Br/3Ba -  for Sale in Myopia Hill, Winchester
Open House
New
$1,575,000
4 Beds
2.5 Baths
3,037 SqFt
Status New
MLS # 72814069
Property Type Single Family
Price Type --
Welcome to 31 Myopia Road, nestled beautifully on a private acre on lovely Myopia Hill. This home exudes simple elegance and comfortable, contemporary living with a spacious floor plan and an abundance of natural light. The first level features a gracious living room with a brick fireplace, custom built cabinetry and a large picture window overlooking the expansive lawn. The updated kitchen is perfect for cooking and entertaining while enjoying spectacular views of the garden. The 2nd level features a well appointed primary bedroom with en-suite bath, garden vista and generous walk-in storage as well as 2 other bedrooms, home office and a full bath. Enjoy long summer evenings on the beautiful deck overlooking the perennial gardens. Easy distance to Winchester CC and Boat Club. A 2 bay garage completes this beautiful property.

1 Wildwood Terrace Unit 2 Winchester, MA 01890

$960,000 - 4Br/3Ba -  for Sale in Winchester
Open House
New
$960,000
4 Beds
2.5 Baths
2,020 SqFt
Status New
MLS # 72814380
Property Type Single Family
Price Type --
Conveniently located just outside Winchester Center and steps to the town tennis courts and beach this turn of the century Victorian 4-bedroom, 2.5 bath townhouse is updated with the modern comforts of today while maintaining its historic charm. The first floor features a fire-placed living room that opens to a dining room with built-ins and hardwood flooring, a large eat-in kitchen completes the first floor. Upstairs find three bedrooms with custom closets and a full bath as well as the must see renovated oversized Master on the top-level an en suite bath with radiant heat and custom closet. Additional features include a sunny front porch, private deeded fenced yard, 2 car detached garage, plenty of additional off-street parking with private driveway, your own basement with washer/dryer and ample storage space. Enjoy all that Winchester has to offer on a private tree lined street in this ideal location close to commuter rail, restaurants, farmers market and more.

1 Wildwood Terrace Unit 2 Winchester, MA 01890

$960,000 - 4Br/3Ba -  for Sale in Winchester
Open House
New
$960,000
4 Beds
2.5 Baths
2,020 SqFt
Status New
MLS # 72814382
Property Type Condominium/co-op
Price Type --
Conveniently located just outside Winchester Center and steps to the town tennis courts and beach this turn of the century Victorian 4-bedroom, 2.5 bath townhouse is updated with the modern comforts of today while maintaining its historic charm. The first floor features a fire-placed living room that opens to a dining room with built-ins and hardwood flooring, a large eat-in kitchen completes the first floor. Upstairs find three bedrooms with custom closets and a full bath as well as the must see renovated oversized Master on the top-level an en suite bath with radiant heat and custom closet. Additional features include a sunny front porch, private deeded fenced yard, 2 car detached garage, plenty of additional off-street parking with private driveway, your own basement with washer/dryer and ample storage space. Enjoy all that Winchester has to offer on a private tree lined street in this ideal location close to commuter rail, restaurants, farmers market and more.

9 Governors Ave Unit 2 Winchester, MA 01890

$649,000 - 3Br/2Ba -  for Sale in Winchester
Open House
New
$649,000
3 Beds
1.5 Baths
1,667 SqFt
Status New
MLS # 72814429
Property Type Condominium/co-op
Price Type --
Highly sought after bi-level condo on a beautiful, tree-lined street! This pristine unit was completely renovated in '08 & has everything you've been searching for. Upon entering, you're instantly greeted by the warm & inviting living room which easily flows into the dining room w/built in cabinets. The updated, eat-in kitchen and ½ bath complete the main level and make this home ideal for entertaining! Upstairs you'll find the three spacious bedrooms, full bath + loads of built-in storage. The newly installed plantation shutters, in-unit laundry, and central a/c make this home both comfortable & practical. An added bonus is the 3-season porch, perfect for outdoor dining and relaxing! Need to be close to the City? The commuter train gets you to N. Station in 18 mins! Love the outdoors? Enjoy the hiking & biking trails in the Fells nearly at your doorstep! Best of all, you're only ½ mile to the shops & restaurants in the Center + all three top-rated schools...this rare gem won't last!

7 Samoset Rd Winchester, MA 01890

$1,999,000 - 6Br/4Ba -  for Sale in Winchester
Open House
New
$1,999,000
6 Beds
3.5 Baths
3,028 SqFt
Status New
MLS # 72813408
Property Type Single Family
Price Type --
Pristine Colonial in desirable Ambrose School district! This impressively spacious home boasts six bedrooms with three full and one half bath. Welcome into a grand entrance leading to the formal dining room with tray ceiling and hardwood floors. The recently updated kitchen includes stainless steel appliances, Wolf range, designer backsplash with a eat-in kitchen. Newly built exterior deck is perfect for entertaining. Formal living and family rooms both have fireplaces! Bedroom/office is located on the main level. Half bath and spacious laundry room with plenty of storage complete the first level. Second floor includes a master bedroom with en-suite bathroom and walk-in closet. Three additional bedrooms and a full bathroom complete the second level. Finished lower level includes library/media/office and another full bathroom complete with a steam shower! This wonderful home with mature landscaping is waiting for you!

14 Mount Pleasant Street Unit 14 Winchester, MA 01890

$1,699,000
6 Beds
2.5 Baths
2,487 SqFt
Status Contingent
MLS # 72812204
Property Type Single Family
Price Type --
Stunning and recently renovated 6 bedroom 2.5 bath home offering top of the line finishes and a highly desirable location right outside the town center! This gorgeous home has been renovated inside and out with only the finest materials, by skilled craftsmen offering grand rooms with original detail, oversized windows, hardwood floors, gas fireplaces & high ceilings. The spacious gourmet eat in kitchen w/ dining area & walls of windows leads to private deck overlooking exclusive yard. The yard has been meticulously maintained with beautiful perennial gardens & stone patio offering a tranquil setting so hard to find this close to town! Second floor offers three generously sized bedrooms with one full bath, third offers three additional bedrooms, laundry and full bath. Full basement, walk out lower level, private driveway. All updated systems, windows, electric, plumbing, siding, roof, central A/C & more. Yard is exclusive to #14. Don't miss this opportunity!

12 Mount Pleasant Street Unit 12 Winchester, MA 01890

$1,999,000 - 6Br/4Ba -  for Sale in Winchester
Open House
$1,999,000
6 Beds
3.5 Baths
4,782 SqFt
Status Active
MLS # 72812251
Property Type Single Family
Price Type --
RARE FIND! Must see this spectacular turn of the century home completely renovated & restored inside and out! This spacious home offers a prime downtown location with 4 floors of space featuring 5+bedrooms, 3.5 baths complete with private ELEVATOR! This recently renovated custom designed town home lives like a single family and offers all the luxuries todays buyers desire, close to town, shops, schools, train to Boston. Stunning kitchen with cherry cabinets, stainless appliances, dining area flooded with sunlight, and family room with walls of windows overlooking beautifully manicured grounds. Formal LR with gas fireplace and detailed moldings. Spacious Master suite with w/fplc, walk in closet & marble bath w/ soaking tub. Third floor w/ 4 addl. beds and full bath. EXCLUSIVE to this unit is also a 3 CAR GARAGE/ CARRIAGE HOUSE w/ full in-law apartment above. The carriage house is handicapped accessible equipped with chair lift, full bath, laundry, kitchenette, living and bedroom areas.

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