Homes Recently Sold in Winchester, MA

price
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1-40 of 65 Homes
Sold, last 90 days
a front view of a house with a yard and trees
a front view of a house with a yard
a living room with a flat screen tv and a couch
a view of front door with a chair
a view of a balcony with wooden floor and iron gate
a living room with furniture and a window
a living room with furniture and a flat screen tv
a kitchen with stainless steel appliances granite countertop a refrigerator a sink dishwasher a stove and white countertops with wooden floor
a kitchen with stainless steel appliances granite countertop a stove and a wooden floors
a kitchen with stainless steel appliances granite countertop a sink stove and refrigerator
a kitchen with stainless steel appliances granite countertop a stove top oven a sink dishwasher a dining table and chairs with wooden floor
a view of a dining room with furniture window and wooden floor
a view of a dining room with furniture and wooden floor
a view of a dining room with furniture window and wooden floor
a dining room with furniture and window
a dining room with furniture and window
a living room with furniture and windows
a view of a chair and table in a room with a window
a work room with furniture and window
a bedroom with a bed window and a flat screen tv
a spacious bedroom with a bed and a chandelier
a view of entryway and hall with wooden floor
a bedroom with a bed and gym equipment
a view of a dresser with wooden floor
a bedroom with a bed and glass door
a large bed sitting in a bedroom next to a window
a bedroom with a bed and wooden floor
a bedroom with a bed a table and a window
a bedroom with bed and a window
a bathroom with a granite countertop sink toilet a mirror and a shower
a balcony with wooden floor and fence
a front view of a house with a yard
a view of a backyard with a tree
a balcony with chairs and a table
a view of balcony with wooden floor
a view of a backyard with a deck
a view of road and trees
an aerial view of a house with a yard
a front view of a house with a yard
an aerial view of a house
an aerial view of residential houses with outdoor space and trees
an aerial view of a house with a garden
1/42
Sold 1/7/26Virtual Tour

$1,255,000

4
Bedrooms
2,696
Square Feet
0.12
Acres

104 Church Street, Winchester, MA 01890

a house view with a garden space
a backyard of a house
a backyard of a house
a backyard of a house with table and chairs under an umbrella
a view of backyard with table and chairs under an umbrella
an aerial view of a house with a yard and trees all around
a living room with furniture and a large window
a living room with furniture a fireplace and a table
a living room with furniture a rug a lamp and a window
a view of a workspace with furniture and a window
a living room with furniture and a flat screen tv
a living room with furniture and a flat screen tv
a living room with furniture and a large window
a living room with furniture and a fireplace
a view of a workspace with furniture and window
a kitchen with stainless steel appliances granite countertop a sink and a stove
a view of a sink and a large window
a kitchen with stainless steel appliances granite countertop a stove and a sink
a view of a living room and kitchen with a large window
a view of a livingroom with furniture and front door
a living room filled with furniture
a very nice looking room with large windows
a view of a living room and a wooden floor
a bathroom with a granite countertop sink and a large mirror
a spacious bedroom with a bed and a large window
a spacious bedroom with a bed and lamp
a bedroom with a bed and a cabinets
a bathroom with a sink shower and a mirror
a bedroom with a bed and dresser
a bedroom with a bed and a television
a spacious bedroom with a bed and a chandelier
a spacious bedroom with a bed next to a window with a flat screen tv
a bathroom with a sink and a bathtub
a view of a chair and table in the backyard
a view of a yard with wooden fence
a view of a field with grass and trees
a view of a back yard of the house
a view of outdoor space and yard
a view of lake and mountain
$2,000,000 | 5 Wood Lane, Winchester, MA 01890
$2,000,000 | 5 Wood Lane, Winchester, MA 01890
$2,000,000 | 5 Wood Lane, Winchester, MA 01890
1/42
Sold 1/20/26

$2,000,000

3
Bedrooms
2,443
Square Feet
1.05
Acres

5 Wood Lane, Winchester, MA 01890

a front view of a house with a yard and trees
a front view of a house with a yard
a dining room with furniture and window
a front view of a house with a yard
an aerial view of a house with outdoor space
a living room with furniture and wooden floor
a view of entryway and hall
a living room with furniture fireplace and a large window
a living room with furniture and a large window
a dining room with furniture a fireplace and wooden floor
a dining room with furniture and window
a kitchen with a sink stove and cabinets
a kitchen with stainless steel appliances a stove a sink and a refrigerator
a view of a dining room and livingroom with furniture wooden floor a chandelier
a large white kitchen with a stove and a wooden floors
a view of a kitchen island wooden floor and windows
a kitchen with stainless steel appliances granite countertop a stove a sink dishwasher a refrigerator and a dining table with wooden floor
a kitchen with stainless steel appliances granite countertop a stove and a window
a living room with furniture a chandelier and a fireplace
a living room with furniture and a large window
a view of staircase with lots of frames on wall and a window
a spacious bathroom with a double vanity sink a mirror a shower and a window
a living room with furniture and a fireplace
a bathroom with a sink a toilet a mirror and a shower
a bed room with a bed and a chair
a spacious bedroom with a large bed and a window
a bathroom with a toilet a sink and a bathtub
a bathroom with a granite countertop sink and a mirror
a bedroom with a bed a dresser and wooden floor
a bed room with a bed and a chair
a view of room with window and wooden floor
a living room with furniture and a large window
a view of a park with plants and large tree
a view of a house with a yard and a garden
a view of a house with backyard and sitting area
a backyard of a house with table and chairs
a front view of a house with garden
a view of lake with mountain
an aerial view of a house with a yard and potted plants
1/39
Sold 11/20/25

$3,599,000

6
Bedrooms
5,876
Square Feet
0.35
Acres

5 Stratford Road, Winchester, MA 01890

$2,900,000 | 26 Swan Road, Winchester, MA 01890
$2,900,000 | 26 Swan Road, Winchester, MA 01890
$2,900,000 | 26 Swan Road, Winchester, MA 01890
$2,900,000 | 26 Swan Road, Winchester, MA 01890
$2,900,000 | 26 Swan Road, Winchester, MA 01890
$2,900,000 | 26 Swan Road, Winchester, MA 01890
$2,900,000 | 26 Swan Road, Winchester, MA 01890
$2,900,000 | 26 Swan Road, Winchester, MA 01890
$2,900,000 | 26 Swan Road, Winchester, MA 01890
$2,900,000 | 26 Swan Road, Winchester, MA 01890
$2,900,000 | 26 Swan Road, Winchester, MA 01890
$2,900,000 | 26 Swan Road, Winchester, MA 01890
$2,900,000 | 26 Swan Road, Winchester, MA 01890
$2,900,000 | 26 Swan Road, Winchester, MA 01890
$2,900,000 | 26 Swan Road, Winchester, MA 01890
$2,900,000 | 26 Swan Road, Winchester, MA 01890
$2,900,000 | 26 Swan Road, Winchester, MA 01890
$2,900,000 | 26 Swan Road, Winchester, MA 01890
$2,900,000 | 26 Swan Road, Winchester, MA 01890
$2,900,000 | 26 Swan Road, Winchester, MA 01890
$2,900,000 | 26 Swan Road, Winchester, MA 01890
$2,900,000 | 26 Swan Road, Winchester, MA 01890
$2,900,000 | 26 Swan Road, Winchester, MA 01890
$2,900,000 | 26 Swan Road, Winchester, MA 01890
$2,900,000 | 26 Swan Road, Winchester, MA 01890
$2,900,000 | 26 Swan Road, Winchester, MA 01890
$2,900,000 | 26 Swan Road, Winchester, MA 01890
$2,900,000 | 26 Swan Road, Winchester, MA 01890
$2,900,000 | 26 Swan Road, Winchester, MA 01890
$2,900,000 | 26 Swan Road, Winchester, MA 01890
$2,900,000 | 26 Swan Road, Winchester, MA 01890
$2,900,000 | 26 Swan Road, Winchester, MA 01890
$2,900,000 | 26 Swan Road, Winchester, MA 01890
$2,900,000 | 26 Swan Road, Winchester, MA 01890
$2,900,000 | 26 Swan Road, Winchester, MA 01890
$2,900,000 | 26 Swan Road, Winchester, MA 01890
$2,900,000 | 26 Swan Road, Winchester, MA 01890
$2,900,000 | 26 Swan Road, Winchester, MA 01890
$2,900,000 | 26 Swan Road, Winchester, MA 01890
$2,900,000 | 26 Swan Road, Winchester, MA 01890
$2,900,000 | 26 Swan Road, Winchester, MA 01890
$2,900,000 | 26 Swan Road, Winchester, MA 01890
1/42
Sold 12/1/25Virtual Tour

$2,900,000

6
Bedrooms
8,463
Square Feet
0.52
Acres

26 Swan Road, Winchester, MA 01890

a house view with a garden space
a view of a porch with furniture
a front view of a house with a yard and outdoor seating
a living room with furniture and a flat screen tv
a view of an empty room with wooden floor and a ceiling fan
a view of empty room with wooden floor and ceiling fan
a view of a dining room and hall with wooden floor
a view of a room with wooden floor and staircase
a kitchen with granite countertop a sink stainless steel appliances and cabinets
a kitchen with stainless steel appliances granite countertop a refrigerator sink and cabinets
a bathroom with a sink and a mirror
a kitchen with stainless steel appliances granite countertop a refrigerator a stove and a sink
a bathroom with a sink and a toilet
a bedroom with a large bed and a chandelier
a view of an empty room with wooden floor and a window
an empty room with wooden floor and windows
a bathroom with a sink a toilet and shower
a bedroom with a large bed and a potted plant
a view of an empty room with wooden floor and a window
a bedroom with a large bed and a flat screen tv
a view of empty room with wooden floor and fan
a view of a workspace with furniture and a potted plant
a view of an empty room and window
a living room with furniture and a flat screen tv
a living room with furniture and a large window
a bedroom with a bed and a chandelier
a bedroom with a bed and a chandelier
a view of living room with washer and dryer
a kitchen with stainless steel appliances granite countertop a refrigerator and a sink
a kitchen with counter top space and dining table
a kitchen with a sink appliances and cabinets
a view of dining room with wooden floor
a bathroom with a sink a toilet and shower
a bed room with a bed and a chandelier
a room with cabinets and bed
a view of a backyard with a tv
a view of a large building next to a road
a view of open space with green space
a backyard of a building with glass top table and chairs
a view of a kitchen with stainless steel appliances
$1,290,000 | 46-48 Swanton Street, Winchester, MA 01890
1/41
Sold 1/29/26

$1,290,000

6
Bedrooms
3,233
Square Feet
0.20
Acres

46-48 Swanton Street, Winchester, MA 01890

a view of a house with a yard
a car parked in front of a house with a small yard
a front view of a house with parking
a front view of a house with a yard
a aerial view of a house with swimming pool
a front view of a house with a yard
a view of swimming pool with trees in the background
a view of a city with an ocean
a view of a city
a view of a yard with a tree
a view of a pathway both side of yard
a street view with large trees
a street view
a view of a yard with plants and trees
a kitchen with granite countertop a sink a window and stainless steel appliances
a kitchen with stainless steel appliances granite countertop a stove and a refrigerator
a table and chairs sitting in a kitchen next to a window
a view of a dining room with furniture and wooden floor
a kitchen with stainless steel appliances a refrigerator and cabinets
a kitchen with stainless steel appliances granite countertop a refrigerator a sink dishwasher a stove and a dining table with wooden floor
a living room with furniture a fireplace and a window
a living room with fireplace furniture and a rug
a living room with furniture and a table with wooden floor
a living room with furniture and a floor to ceiling window
a living room with furniture and floor to ceiling windows
a living room with furniture and a window
a living room with furniture a flat screen tv and floor to ceiling windows
a view of a livingroom with wooden floor and furniture
a bedroom with a bed and a table
a bathroom with a sink toilet vanity and shower
a bathroom with a shower
a bedroom with a bed and a table
a bedroom with a bed and a chandelier
a bedroom with a bed and a window
a bedroom with a bed and wooden floor
a bedroom with a bed and wooden floor
a bathroom with a granite countertop sink a mirror and a shower
a bathroom with a toilet and a bathtub
a view of a city
an aerial view of residential building and ocean
a view of an ocean
$2,450,000 | 30 Prospect Street, Winchester, MA 01890
1/42
Sold 12/16/25

$2,450,000

4
Bedrooms
2,519
Square Feet
0.50
Acres

30 Prospect Street, Winchester, MA 01890

an aerial view of residential houses with outdoor space and trees
front view of a house with a yard
a view of a swimming pool with an outdoor seating and a garden
a view of lake
a view of a lake with houses in the back
a view of a swimming pool with a garden
a view of balcony with wooden floor and fence
a view of balcony with wooden floor and fence
a kitchen with a stove oven and sink
a kitchen with a refrigerator and a sink
a kitchen with a refrigerator stove and wooden floor
a kitchen with white cabinets and appliances
a living room with furniture and a large window
a living room with furniture and a large window
a living room with furniture and a fireplace
a living room with furniture and a fireplace
a view of a dining room with furniture window and outside view
a view of a dining room with furniture and a chandelier
a living room with furniture a fireplace and a window
a living room with furniture and a fireplace
a living room with furniture and a table
a view of a room with a table and chairs
a view of an entryway with wooden floor leading to a furnished livingroom and windows
a bedroom with a large bed and a window
a bedroom with a large bed and a window
a view of front door
a bathroom with a toilet a sink and a mirror
a bedroom with a bed and a window
a bedroom with a bed and a window
a view of an empty room with wooden floor and a window
a bathroom with a sink a mirror and a shower
an empty room with wooden floor and closet area
a view of an empty room
a big room with wooden floor and windows
an aerial view of a residential houses with swimming pool and outdoor space
an aerial view of a house with a yard basket ball court and outdoor seating
a front view of a house with a yard
a view of a house with a wooden fence
an aerial view of residential houses with outdoor space
a view of a lake with houses in the back
an aerial view of lake residential house with swimming pool and green space
$1,549,000 | 32 Woodside Road, Winchester, MA 01890
1/42
Sold 12/15/25

$1,549,000

3
Bedrooms
2,587
Square Feet
0.42
Acres

32 Woodside Road, Winchester, MA 01890

$1,015,000 | 9 Sylvester Court, Winchester, MA 01890
$1,015,000 | 9 Sylvester Court, Winchester, MA 01890
$1,015,000 | 9 Sylvester Court, Winchester, MA 01890
$1,015,000 | 9 Sylvester Court, Winchester, MA 01890
$1,015,000 | 9 Sylvester Court, Winchester, MA 01890
$1,015,000 | 9 Sylvester Court, Winchester, MA 01890
$1,015,000 | 9 Sylvester Court, Winchester, MA 01890
$1,015,000 | 9 Sylvester Court, Winchester, MA 01890
$1,015,000 | 9 Sylvester Court, Winchester, MA 01890
$1,015,000 | 9 Sylvester Court, Winchester, MA 01890
$1,015,000 | 9 Sylvester Court, Winchester, MA 01890
$1,015,000 | 9 Sylvester Court, Winchester, MA 01890
$1,015,000 | 9 Sylvester Court, Winchester, MA 01890
$1,015,000 | 9 Sylvester Court, Winchester, MA 01890
$1,015,000 | 9 Sylvester Court, Winchester, MA 01890
$1,015,000 | 9 Sylvester Court, Winchester, MA 01890
$1,015,000 | 9 Sylvester Court, Winchester, MA 01890
$1,015,000 | 9 Sylvester Court, Winchester, MA 01890
$1,015,000 | 9 Sylvester Court, Winchester, MA 01890
$1,015,000 | 9 Sylvester Court, Winchester, MA 01890
$1,015,000 | 9 Sylvester Court, Winchester, MA 01890
$1,015,000 | 9 Sylvester Court, Winchester, MA 01890
$1,015,000 | 9 Sylvester Court, Winchester, MA 01890
$1,015,000 | 9 Sylvester Court, Winchester, MA 01890
$1,015,000 | 9 Sylvester Court, Winchester, MA 01890
$1,015,000 | 9 Sylvester Court, Winchester, MA 01890
$1,015,000 | 9 Sylvester Court, Winchester, MA 01890
$1,015,000 | 9 Sylvester Court, Winchester, MA 01890
$1,015,000 | 9 Sylvester Court, Winchester, MA 01890
$1,015,000 | 9 Sylvester Court, Winchester, MA 01890
$1,015,000 | 9 Sylvester Court, Winchester, MA 01890
$1,015,000 | 9 Sylvester Court, Winchester, MA 01890
$1,015,000 | 9 Sylvester Court, Winchester, MA 01890
$1,015,000 | 9 Sylvester Court, Winchester, MA 01890
1/34
Sold 12/1/25

$1,015,000

4
Bedrooms
2,001
Square Feet
0.18
Acres

9 Sylvester Court, Winchester, MA 01890

$1,290,000 | 40 Sargent Road, Winchester, MA 01890
$1,290,000 | 40 Sargent Road, Winchester, MA 01890
$1,290,000 | 40 Sargent Road, Winchester, MA 01890
$1,290,000 | 40 Sargent Road, Winchester, MA 01890
$1,290,000 | 40 Sargent Road, Winchester, MA 01890
$1,290,000 | 40 Sargent Road, Winchester, MA 01890
$1,290,000 | 40 Sargent Road, Winchester, MA 01890
$1,290,000 | 40 Sargent Road, Winchester, MA 01890
$1,290,000 | 40 Sargent Road, Winchester, MA 01890
$1,290,000 | 40 Sargent Road, Winchester, MA 01890
$1,290,000 | 40 Sargent Road, Winchester, MA 01890
$1,290,000 | 40 Sargent Road, Winchester, MA 01890
$1,290,000 | 40 Sargent Road, Winchester, MA 01890
$1,290,000 | 40 Sargent Road, Winchester, MA 01890
$1,290,000 | 40 Sargent Road, Winchester, MA 01890
$1,290,000 | 40 Sargent Road, Winchester, MA 01890
$1,290,000 | 40 Sargent Road, Winchester, MA 01890
$1,290,000 | 40 Sargent Road, Winchester, MA 01890
$1,290,000 | 40 Sargent Road, Winchester, MA 01890
$1,290,000 | 40 Sargent Road, Winchester, MA 01890
$1,290,000 | 40 Sargent Road, Winchester, MA 01890
$1,290,000 | 40 Sargent Road, Winchester, MA 01890
$1,290,000 | 40 Sargent Road, Winchester, MA 01890
$1,290,000 | 40 Sargent Road, Winchester, MA 01890
$1,290,000 | 40 Sargent Road, Winchester, MA 01890
$1,290,000 | 40 Sargent Road, Winchester, MA 01890
$1,290,000 | 40 Sargent Road, Winchester, MA 01890
$1,290,000 | 40 Sargent Road, Winchester, MA 01890
$1,290,000 | 40 Sargent Road, Winchester, MA 01890
$1,290,000 | 40 Sargent Road, Winchester, MA 01890
$1,290,000 | 40 Sargent Road, Winchester, MA 01890
$1,290,000 | 40 Sargent Road, Winchester, MA 01890
$1,290,000 | 40 Sargent Road, Winchester, MA 01890
$1,290,000 | 40 Sargent Road, Winchester, MA 01890
$1,290,000 | 40 Sargent Road, Winchester, MA 01890
$1,290,000 | 40 Sargent Road, Winchester, MA 01890
$1,290,000 | 40 Sargent Road, Winchester, MA 01890
1/37
Sold 12/5/25Virtual Tour

$1,290,000

3
Bedrooms
1,492
Square Feet
0.20
Acres

40 Sargent Road, Winchester, MA 01890

a picture of city view with outdoor seating
an aerial view of a swimming pool
a front view of a house with a yard and garage
a front view of a house with garden
a front view of a house with garden
a view of entryway with wooden floor and windows
a work room with furniture and potted plants
a living room with furniture a fireplace and a flat screen tv
a living room with furniture a fireplace and a flat screen tv
a living room with furniture a fireplace and a flat screen tv
a living room with furniture and a fireplace
a kitchen with stainless steel appliances granite countertop a stove a sink a dining table and chairs with wooden floor
a kitchen with granite countertop a sink a center island and stainless steel appliances
a kitchen with a sink and a stove top oven
a living room with fireplace furniture flat screen tv and wooden floor
a kitchen with stainless steel appliances granite countertop a sink stove and cabinets
a living room with furniture and a large window
a very nice looking dining room with a large window
a living room with furniture and a floor to ceiling window
a bedroom with a bed and a flat screen tv
a bedroom with a bed and flat screen tv
a en suite bathroom with a granite countertop sink and a mirror
a view of a bathroom with a shower and a sink
a view of walk in closet with clothes and shoes
a utility room with dryer and washer
a close view of utility room with washer and dryer
a living room with furniture and wooden floor
a living room with furniture and wooden floor
a living room with furniture and a flat screen tv
a living room with furniture and a flat screen tv
a view of a hallway with windows
a bathroom with a double vanity sink and a mirror
a bathroom with a shower and toilet
an empty room with wooden floor and windows
a bedroom with a bed and a couch
a bedroom with a bed and a window
a living room with furniture
a view of a dining room with furniture
a living room with furniture and a flat screen tv
a view of a patio with couches chairs and a potted plant
a view of a house with backyard and porch
a view of a house with backyard and sitting area
1/42
Sold 1/16/26Virtual Tour

$2,175,000

3
Bedrooms
3,953
Square Feet

19 Gershon Way, Unit 1, Winchester, MA 01890

a front view of residential houses
a front view of a house with a yard
a view of a chairs and table in the balcony
a kitchen with stainless steel appliances granite countertop a stove a sink and a wooden floors
a kitchen with stainless steel appliances granite countertop a kitchen island a table and chairs in it
a view of a dining room with furniture window and wooden floor
a living room with furniture and a flat screen tv
a living room with furniture a large window and a chandelier
a bathroom with a toilet a sink and a mirror
a bedroom with a bed and a window
a bedroom with furniture and a large window
a bedroom with furniture and a large window
a bedroom with a bed and a chandelier
a bathroom with a granite countertop toilet a sink and a mirror
a bathroom with a bathtub and a shower
a bedroom with a bed a couch and a window
a bedroom with a large bed and a chandelier
a bathroom with a granite countertop sink mirror and
a bedroom with furniture and wooden floor
a workspace with furniture and wooden floor
a workspace with furniture and window
a bed room with a bed and a television
a bedroom with a large bed and two windows
a bathroom with a granite countertop sink and a mirror
a bathroom with a granite countertop sink a toilet and a shower
a living room with furniture and a couch
a living room with furniture and a wooden floor
a living room with lots of white furniture and kitchen view
a view of a patio with table and chairs potted plants and a large tree
a view of backyard of the house
a view of backyard with tree
a front view of a house with a yard
an aerial view of a house with outdoor space
an aerial view of residential building with outdoor space
a view of a city
1/35
Sold 12/24/25

$1,499,000

5
Bedrooms
3,141
Square Feet

209 Washington Street, Unit 209, Winchester, MA 01890

$1,090,000 | 16 Ridge Street, Winchester, MA 01890
$1,090,000 | 16 Ridge Street, Winchester, MA 01890
$1,090,000 | 16 Ridge Street, Winchester, MA 01890
$1,090,000 | 16 Ridge Street, Winchester, MA 01890
$1,090,000 | 16 Ridge Street, Winchester, MA 01890
$1,090,000 | 16 Ridge Street, Winchester, MA 01890
$1,090,000 | 16 Ridge Street, Winchester, MA 01890
$1,090,000 | 16 Ridge Street, Winchester, MA 01890
$1,090,000 | 16 Ridge Street, Winchester, MA 01890
$1,090,000 | 16 Ridge Street, Winchester, MA 01890
$1,090,000 | 16 Ridge Street, Winchester, MA 01890
$1,090,000 | 16 Ridge Street, Winchester, MA 01890
$1,090,000 | 16 Ridge Street, Winchester, MA 01890
$1,090,000 | 16 Ridge Street, Winchester, MA 01890
$1,090,000 | 16 Ridge Street, Winchester, MA 01890
$1,090,000 | 16 Ridge Street, Winchester, MA 01890
$1,090,000 | 16 Ridge Street, Winchester, MA 01890
$1,090,000 | 16 Ridge Street, Winchester, MA 01890
$1,090,000 | 16 Ridge Street, Winchester, MA 01890
$1,090,000 | 16 Ridge Street, Winchester, MA 01890
$1,090,000 | 16 Ridge Street, Winchester, MA 01890
$1,090,000 | 16 Ridge Street, Winchester, MA 01890
$1,090,000 | 16 Ridge Street, Winchester, MA 01890
$1,090,000 | 16 Ridge Street, Winchester, MA 01890
$1,090,000 | 16 Ridge Street, Winchester, MA 01890
$1,090,000 | 16 Ridge Street, Winchester, MA 01890
$1,090,000 | 16 Ridge Street, Winchester, MA 01890
$1,090,000 | 16 Ridge Street, Winchester, MA 01890
$1,090,000 | 16 Ridge Street, Winchester, MA 01890
$1,090,000 | 16 Ridge Street, Winchester, MA 01890
$1,090,000 | 16 Ridge Street, Winchester, MA 01890
$1,090,000 | 16 Ridge Street, Winchester, MA 01890
$1,090,000 | 16 Ridge Street, Winchester, MA 01890
$1,090,000 | 16 Ridge Street, Winchester, MA 01890
$1,090,000 | 16 Ridge Street, Winchester, MA 01890
$1,090,000 | 16 Ridge Street, Winchester, MA 01890
$1,090,000 | 16 Ridge Street, Winchester, MA 01890
$1,090,000 | 16 Ridge Street, Winchester, MA 01890
$1,090,000 | 16 Ridge Street, Winchester, MA 01890
$1,090,000 | 16 Ridge Street, Winchester, MA 01890
$1,090,000 | 16 Ridge Street, Winchester, MA 01890
$1,090,000 | 16 Ridge Street, Winchester, MA 01890
1/42
Sold 2/6/26

$1,090,000

3
Bedrooms
1,844
Square Feet
0.62
Acres

16 Ridge Street, Winchester, MA 01890

a front view of a house with a yard
a front view of a house with a yard
a view of a house with a small yard and wooden floor and fence
a living room with furniture kitchen view and a wooden floor
a living room with furniture and a dining table
a living room with furniture and a wooden floor
a living room with furniture and a large window
a living room with furniture and a wooden floor
a bathroom with a sink and a mirror
a dining room with wooden floor a glass table and chairs
a dining room with furniture and window
a view of a dining room with furniture and wooden floor
a kitchen with stainless steel appliances granite countertop a sink a stove a refrigerator and island with wooden floor
a kitchen with stainless steel appliances granite countertop a stove a sink a dining table and chairs with wooden floor
a kitchen with kitchen island white cabinets and white appliances
a kitchen with a table and chairs in it
a kitchen with a counter space cabinets and wooden floor
a view of hallway with bathroom and mirror
a bathroom with a sink and a toilet
a view of entryway and hall with wooden floor
a bedroom with a large bed and a couch
a bedroom with a bed and wooden floor
a bathroom with a double vanity sink a toilet a mirror and window
a view of a bathtub in a bathroom
a view of an empty room with wooden floor and a window
wooden floor in an empty room
a view of an empty room with wooden floor and a window
a bathroom with a granite countertop sink toilet a mirror and shower
a view of entryway with wooden floor
a living room with furniture and a flat screen tv
a living room with furniture and a flat screen tv
a living room with furniture and a flat screen tv
a living room with furniture and a flat screen tv
a view of a room with wooden floor and a window
a bathroom with a sink a toilet and with mirror
a front view of a house with a yard
a front view of a house with a yard
a view of a deck with furniture
a white house that has tree in front of it
a view of a backyard of the house
a view of a house with a yard and pathway
a car parked in front of house with a yard
1/42
Sold 11/21/25Virtual Tour

$1,199,000

3
Bedrooms
2,459
Square Feet
Unavailable
Acres

162 Swanton Street, Unit 162, Winchester, MA 01890

a kitchen with a sink a window stainless steel appliances and cabinets
a kitchen with stainless steel appliances a table chairs and a refrigerator
a front view of a house with a yard
an aerial view of a house with garden space and street view
a view of outdoor space with playground and green space
a front view of house with yard and green space
a front view of a house with a yard
a bedroom with a bed and furniture with wooden floor
a view of a dining room with furniture window and wooden floor
a view of a dining room with furniture
a living room with furniture a rug and wooden floor
a view of a dining room with furniture window and wooden floor
a kitchen with a stove a sink and a microwave
a kitchen with stainless steel appliances granite countertop a stove a sink and a microwave
a living room with furniture and a window
a living room with furniture a clock and a rug
a living room with furniture and a large window
a bathroom with a sink and a toilet
a view of a bathroom from a hallway
a bedroom with a bed and a large window
a large bed sitting in a bedroom next to a window
a bedroom with a bed and a painting on the wall
a bedroom with a bed and a window
a bathroom with a sink a toilet and a window
a bedroom with a bed and a table
an empty room with wooden floor and windows
a living room with furniture and a fireplace
a living room with fireplace furniture and a large window
a workspace with a window
a front view of a house with yard and green space
a front view of a house with a garden
a view of a park with large trees
a house view with a backyard space
a front view of a house with garden
a view of a field with a trees in the background
1/35
Sold 12/24/25Virtual Tour

$1,310,000

5
Bedrooms
3,033
Square Feet
0.35
Acres

7 Thornberry Road, Winchester, MA 01890

$1,825,000 | 19 Glengarry Road, Winchester, MA 01890
$1,825,000 | 19 Glengarry Road, Winchester, MA 01890
$1,825,000 | 19 Glengarry Road, Winchester, MA 01890
$1,825,000 | 19 Glengarry Road, Winchester, MA 01890
$1,825,000 | 19 Glengarry Road, Winchester, MA 01890
$1,825,000 | 19 Glengarry Road, Winchester, MA 01890
$1,825,000 | 19 Glengarry Road, Winchester, MA 01890
$1,825,000 | 19 Glengarry Road, Winchester, MA 01890
$1,825,000 | 19 Glengarry Road, Winchester, MA 01890
$1,825,000 | 19 Glengarry Road, Winchester, MA 01890
$1,825,000 | 19 Glengarry Road, Winchester, MA 01890
$1,825,000 | 19 Glengarry Road, Winchester, MA 01890
$1,825,000 | 19 Glengarry Road, Winchester, MA 01890
$1,825,000 | 19 Glengarry Road, Winchester, MA 01890
$1,825,000 | 19 Glengarry Road, Winchester, MA 01890
$1,825,000 | 19 Glengarry Road, Winchester, MA 01890
$1,825,000 | 19 Glengarry Road, Winchester, MA 01890
$1,825,000 | 19 Glengarry Road, Winchester, MA 01890
$1,825,000 | 19 Glengarry Road, Winchester, MA 01890
$1,825,000 | 19 Glengarry Road, Winchester, MA 01890
$1,825,000 | 19 Glengarry Road, Winchester, MA 01890
$1,825,000 | 19 Glengarry Road, Winchester, MA 01890
$1,825,000 | 19 Glengarry Road, Winchester, MA 01890
$1,825,000 | 19 Glengarry Road, Winchester, MA 01890
$1,825,000 | 19 Glengarry Road, Winchester, MA 01890
$1,825,000 | 19 Glengarry Road, Winchester, MA 01890
$1,825,000 | 19 Glengarry Road, Winchester, MA 01890
$1,825,000 | 19 Glengarry Road, Winchester, MA 01890
$1,825,000 | 19 Glengarry Road, Winchester, MA 01890
$1,825,000 | 19 Glengarry Road, Winchester, MA 01890
$1,825,000 | 19 Glengarry Road, Winchester, MA 01890
$1,825,000 | 19 Glengarry Road, Winchester, MA 01890
$1,825,000 | 19 Glengarry Road, Winchester, MA 01890
$1,825,000 | 19 Glengarry Road, Winchester, MA 01890
$1,825,000 | 19 Glengarry Road, Winchester, MA 01890
$1,825,000 | 19 Glengarry Road, Winchester, MA 01890
$1,825,000 | 19 Glengarry Road, Winchester, MA 01890
$1,825,000 | 19 Glengarry Road, Winchester, MA 01890
$1,825,000 | 19 Glengarry Road, Winchester, MA 01890
$1,825,000 | 19 Glengarry Road, Winchester, MA 01890
$1,825,000 | 19 Glengarry Road, Winchester, MA 01890
$1,825,000 | 19 Glengarry Road, Winchester, MA 01890
1/42
Sold 12/8/25Virtual Tour

$1,825,000

6
Bedrooms
3,521
Square Feet
0.25
Acres

19 Glengarry Road, Winchester, MA 01890

a front view of a residential apartment building with a yard
a front view of a house with a yard and garage
a view of entryway
a room with a fireplace
a view of an empty room with a window and a kitchen
a bathroom with a granite countertop sink and a mirror
a kitchen with white cabinets and stainless steel appliances
a kitchen with white cabinets and chandelier
a view of a kitchen and windows
a view of an empty room with wooden floor and a window
a view of a room with wooden floor
a view of an empty room
a spacious bathroom with a double vanity sink a mirror and a bathtub
a bathroom with a double vanity sink a mirror and a shower
a view of empty room with wooden floor and fan
a view of utility room
a bathroom with a toilet a sink and a mirror
a view of an empty room with wooden floor and a window
a spacious bathroom with a double vanity sink and mirror
a bathroom with a shower
a front view of a house with a yard
$2,400,000 | 19 Laurel Hill Lane, Winchester, MA 01890
1/22
Sold 12/18/25

$2,400,000

5
Bedrooms
3,700
Square Feet
0.31
Acres

19 Laurel Hill Lane, Winchester, MA 01890

a front view of a house with garden
a front view of a house with a yard
a view of a small yard from a balcony
a view of an outdoor sitting area with furniture
a view of outdoor space and entertaining space
a view of a yard with a tree
an aerial view of ocean residential house with outdoor space and river
a living room with furniture and a window
a living room with furniture and a fireplace
a living room with furniture and a fireplace
a living room with furniture and a window
a living room with furniture a potted plant and a large window
a view of a dining room with furniture window and wooden floor
a dining room with wooden floor and large windows
a large kitchen with stainless steel appliances lots of counter space and a sink
a kitchen with stainless steel appliances granite countertop a refrigerator and a sink
a kitchen with sink a window and cabinets
a kitchen with stainless steel appliances granite countertop a sink and cabinets
a very nice looking living room with a large window
a living room with furniture and a large window
a living room with furniture and a large window
a view of entryway and hall with wooden floor
a living room with furniture chess table and a window
a bedroom with a bed couch and windows
a very nice looking room with a large window
a bathroom with a sink and a mirror
a bedroom with a bed and a large window
a bathroom with a sink toilet and shower
a living room with furniture and a rug
a bedroom with a bed and a dresser
a bedroom with a bed and a window
a living room with a couch and potted plant with wooden floor
a living room with furniture and a book shelf
a bathroom with a toilet a sink a mirror and a window
a bathroom with a shower and a sink
a view of a room with gym equipment
a living room with lots of furniture and kitchen view
a living room with furniture and a rug
a picture of a black and white wall
unknown
a picture of a floor plan
$2,150,000 | 7 Appalachian Road, Winchester, MA 01890
1/42
Sold 2/2/26Virtual Tour

$2,150,000

4
Bedrooms
3,263
Square Feet
0.43
Acres

7 Appalachian Road, Winchester, MA 01890

a dining room with furniture and wooden floor
a living room with furniture fireplace and flat screen tv
a view of entryway with wooden floor
a view of a dining room with furniture window and wooden floor
a view of entryway with wooden floor and stairs
a view of a bedroom with window
a living room with furniture and a wooden floor
a bathroom with a granite countertop sink a mirror and a bathtub
a bedroom with a bed and window
a bedroom with a bed and wooden floor
a view of an empty room
a view of a backyard with potted plants and a large tree
a front view of a house with garden
$1,150,000 | 50 Lincoln Street, Winchester, MA 01890
$1,150,000 | 50 Lincoln Street, Winchester, MA 01890
$1,150,000 | 50 Lincoln Street, Winchester, MA 01890
$1,150,000 | 50 Lincoln Street, Winchester, MA 01890
$1,150,000 | 50 Lincoln Street, Winchester, MA 01890
$1,150,000 | 50 Lincoln Street, Winchester, MA 01890
$1,150,000 | 50 Lincoln Street, Winchester, MA 01890
$1,150,000 | 50 Lincoln Street, Winchester, MA 01890
$1,150,000 | 50 Lincoln Street, Winchester, MA 01890
$1,150,000 | 50 Lincoln Street, Winchester, MA 01890
$1,150,000 | 50 Lincoln Street, Winchester, MA 01890
$1,150,000 | 50 Lincoln Street, Winchester, MA 01890
$1,150,000 | 50 Lincoln Street, Winchester, MA 01890
$1,150,000 | 50 Lincoln Street, Winchester, MA 01890
$1,150,000 | 50 Lincoln Street, Winchester, MA 01890
$1,150,000 | 50 Lincoln Street, Winchester, MA 01890
1/29
Sold 12/12/25Virtual Tour

$1,150,000

4
Bedrooms
2,004
Square Feet
0.08
Acres

50 Lincoln Street, Winchester, MA 01890

front view of house with a yard
a view of a backyard with sitting area and furniture
a view of a porch with furniture and a gate
a living room with furniture and a fireplace
a living room with furniture and a large window
a living room with furniture and a fireplace
a living room with furniture and a fireplace
a view of a dining room with furniture window and wooden floor
a dining room with furniture potted plants and wooden floor
a kitchen with a sink stove and cabinets
a kitchen with a refrigerator sink and cabinets
a kitchen with stainless steel appliances granite countertop a sink stove and refrigerator
a kitchen with stainless steel appliances a stove a sink a refrigerator and a microwave
a kitchen with granite countertop a sink stainless steel appliances and cabinets
a view of an entryway with wooden floor leading to a furnished livingroom and windows
a view of a livingroom with furniture and staircase
a bedroom with a bed and lamp
a dining room with furniture and window
a bedroom with a bed and a lamp with wooden floor
a view of a hallway with wooden floor and staircase
a bedroom with a bed and a couch
a bedroom with a bed and a window
a view of a hallway with wooden floor and a potted plant
a bedroom with a bed and a flat screen tv
a bathroom with a sink a toilet and shower
an entryway with wooden floor and cabinet
a utility room with lot of cabinets
a view of gym
a view of a back yard on the house
a backyard of a house with plants and large trees
front view of house with a yard
a view of a small house with a yard
a black and white photo of a living room
a view of a house with a yard
a bathroom with a sink a toilet and shower
1/35
Sold 1/5/26

$900,000

3
Bedrooms
1,425
Square Feet
0.17
Acres

571 Washington Street, Winchester, MA 01890

a front view of a house with a garden
a view of empty room with wooden floor and fan
a bathroom with a sink mirror and a bathtub
a view of entrance door with wooden floor
a view of a hallway with wooden floor and a living room
a front view of a house with a yard
a view of yard with patio
a backyard of a house with table and chairs
a view of a backyard of the house
a view of a yard with an outdoor space
a front view of a house with a yard
a view of a wooden door of the house
a view of a yard with an trees
a view of yard
a view of a indoor swimming pool
a view of an empty room with wooden floor and a window
a view of a room with a large window and wooden floor
a view of empty room with wooden floor and fan
a view of a room with window and wooden floor
a view of a hallway with wooden floor and staircase
a kitchen with stainless steel appliances granite countertop a sink and cabinets
a kitchen with stainless steel appliances granite countertop a sink stove and cabinets
a kitchen with stainless steel appliances granite countertop a sink stove and refrigerator
a view of walk in closet and bedroom
a bathroom with a sink and a mirror
a view of a hallway with windows and chandelier
a view of a hallway view with staircase
a view of front door with wooden floor and door
wooden floor in an empty room with a window
wooden floor in an empty room with a window
an empty room with wooden floor and windows
a view of walk in closet with clothes and shoes
a view of a small yard with plants and wooden fence
an aerial view of a house with a yard and garden
view of a city
an aerial view of a house with a yard and garden view
$940,000 | 446 Highland Avenue, Winchester, MA 01890
1/37
Sold 12/23/25

$940,000

2
Bedrooms
2,033
Square Feet
0.28
Acres

446 Highland Avenue, Winchester, MA 01890

$1,250,000 | 35 Harvard Street, Winchester, MA 01890
$1,250,000 | 35 Harvard Street, Winchester, MA 01890
$1,250,000 | 35 Harvard Street, Winchester, MA 01890
$1,250,000 | 35 Harvard Street, Winchester, MA 01890
$1,250,000 | 35 Harvard Street, Winchester, MA 01890
$1,250,000 | 35 Harvard Street, Winchester, MA 01890
$1,250,000 | 35 Harvard Street, Winchester, MA 01890
$1,250,000 | 35 Harvard Street, Winchester, MA 01890
$1,250,000 | 35 Harvard Street, Winchester, MA 01890
$1,250,000 | 35 Harvard Street, Winchester, MA 01890
$1,250,000 | 35 Harvard Street, Winchester, MA 01890
$1,250,000 | 35 Harvard Street, Winchester, MA 01890
$1,250,000 | 35 Harvard Street, Winchester, MA 01890
$1,250,000 | 35 Harvard Street, Winchester, MA 01890
$1,250,000 | 35 Harvard Street, Winchester, MA 01890
$1,250,000 | 35 Harvard Street, Winchester, MA 01890
$1,250,000 | 35 Harvard Street, Winchester, MA 01890
$1,250,000 | 35 Harvard Street, Winchester, MA 01890
$1,250,000 | 35 Harvard Street, Winchester, MA 01890
$1,250,000 | 35 Harvard Street, Winchester, MA 01890
$1,250,000 | 35 Harvard Street, Winchester, MA 01890
$1,250,000 | 35 Harvard Street, Winchester, MA 01890
$1,250,000 | 35 Harvard Street, Winchester, MA 01890
$1,250,000 | 35 Harvard Street, Winchester, MA 01890
$1,250,000 | 35 Harvard Street, Winchester, MA 01890
$1,250,000 | 35 Harvard Street, Winchester, MA 01890
$1,250,000 | 35 Harvard Street, Winchester, MA 01890
$1,250,000 | 35 Harvard Street, Winchester, MA 01890
$1,250,000 | 35 Harvard Street, Winchester, MA 01890
$1,250,000 | 35 Harvard Street, Winchester, MA 01890
$1,250,000 | 35 Harvard Street, Winchester, MA 01890
$1,250,000 | 35 Harvard Street, Winchester, MA 01890
$1,250,000 | 35 Harvard Street, Winchester, MA 01890
$1,250,000 | 35 Harvard Street, Winchester, MA 01890
$1,250,000 | 35 Harvard Street, Winchester, MA 01890
$1,250,000 | 35 Harvard Street, Winchester, MA 01890
1/36
Sold 11/14/25

$1,250,000

5
Bedrooms
1,706
Square Feet
0.13
Acres

35 Harvard Street, Winchester, MA 01890

a view of a house with backyard and sitting area
a front view of a house with a yard
a front view of a house with a garden
a view of a house with backyard and sitting area
a view of swimming pool with a yard and large tree
a front view of a house with a yard
a view of a road with a house in the background
a view of an empty room with window and wooden floor
a view of an empty room with wooden floor and a window
a view of empty room with a fireplace and wooden floor
a kitchen with granite countertop white cabinets and sink
a bathroom with a sink a mirror and a shower
a view of a kitchen with white cabinets and white appliances
a spacious bathroom with a double vanity sink a mirror and a bathtub next to a window
a view of empty room with wooden floor and fan
a view of empty room with wooden floor
a view of an empty room with wooden floor
an empty room with wooden floor and windows
an empty room with wooden floor cabinet and windows
an empty room with wooden floor and windows
a bathroom with a toilet a sink and bathtub
an empty room with wooden floor and windows
a view of an empty room with window and wooden floor
a view of an empty room with wooden floor and a window
a bathroom with a sink a toilet a vanity a bathtub and a shower
a view of a room with gym equipment
a view of a pathway of a park with large trees
a view of a small house with a patio and a fire pit
front view of a house with a yard
a view of a house with a yard
a view of a garden
a backyard of a house
a picture of a wall with a white wall and a white wall
a picture of a floor plan
a picture of floor plan
$1,425,000 | 102 Hillcrest Parkway, Winchester, MA 01890
$1,425,000 | 102 Hillcrest Parkway, Winchester, MA 01890
$1,425,000 | 102 Hillcrest Parkway, Winchester, MA 01890
1/38
Sold 12/1/25

$1,425,000

4
Bedrooms
1,755
Square Feet
0.29
Acres

102 Hillcrest Parkway, Winchester, MA 01890

front view of a house with a yard
an aerial view of a house with a yard
an aerial view of a house with a yard
an aerial view of residential houses with outdoor space and trees
an aerial view of a house
a front view of a house with a yard and trees
a front view of a house
a view of an empty room with wooden floor fireplace and a window
a view of an empty room with wooden floor fireplace and a window
a view of an empty room with a window and fireplace
an empty room with wooden floor and windows
an empty room with wooden floor and windows
a view of a room that has a window in it
a bathroom with a bathtub and a window
a view of closet area
a living room with a flat screen tv and refrigerator
a kitchen with stainless steel appliances granite countertop a sink and a refrigerator
a kitchen with stainless steel appliances granite countertop a stove and a sink
a room with window
a living room with stainless steel appliances kitchen island furniture and a large window
a bathroom with a toilet a sink and a window
a view of room with window and chandelier
wooden floor in an empty room with a window
a view of empty room with wooden floor
a bathroom with a sink toilet and shower
a view of a room with wooden floor and windows
a bathroom with a sink a toilet and a mirror
a bathroom with a shower and a bath tub
a view of an empty room
an empty room with fireplace and fan
a living room with furniture and a fireplace
a front view of a house with a yard and trees
a front view of a house with garden
a view of a house with a yard
a view of a house with a big yard and large trees
an aerial view of a house
$1,558,200 | 82 Hillcrest Parkway, Winchester, MA 01890
$1,558,200 | 82 Hillcrest Parkway, Winchester, MA 01890
1/38
Sold 1/5/26

$1,558,200

3
Bedrooms
1,882
Square Feet
0.56
Acres

82 Hillcrest Parkway, Winchester, MA 01890

a front view of a house with garden
a front view of a house with a yard
a front view of a house with a yard
a front view of a house with a yard
a view of a livingroom with a fireplace
a living room with a fireplace
a view of empty room with a fireplace and window
a view of an empty room with a fireplace and a window
wooden floor in an empty room with a window
wooden floor in an empty room with a window
a kitchen with white cabinets and white appliances
a kitchen with granite countertop a sink cabinets stainless steel appliances and a window
a kitchen with a sink dishwasher a stove and a refrigerator
a kitchen with granite countertop white cabinets and stainless steel appliances
a view of an empty room with a window
an empty room with windows
wooden floor in an empty room with a window
a bathroom with a sink toilet and mirror
a view of an empty room
a view of an empty room with a window
an empty room with windows and fan
a view of an empty room with a window
a bathroom with a toilet a sink and bathtub
a bathroom with a toilet sink and shower
an empty room with a fireplace and window
a view of livingroom with furniture and window
a bathroom with a toilet a sink and shower
a bathroom with a shower
a view of utility room
a living room with a fireplace and a ceiling fan
a view of an empty room with a fireplace
a view of a storage & utility room
a view of a house with backyard and garden
1/33
Sold 12/22/25Virtual Tour

$1,325,000

3
Bedrooms
1,942
Square Feet
0.23
Acres

12 Canterbury Road, Winchester, MA 01890

$1,627,000 | 73 Grove Street, Winchester, MA 01890
$1,627,000 | 73 Grove Street, Winchester, MA 01890
$1,627,000 | 73 Grove Street, Winchester, MA 01890
$1,627,000 | 73 Grove Street, Winchester, MA 01890
$1,627,000 | 73 Grove Street, Winchester, MA 01890
$1,627,000 | 73 Grove Street, Winchester, MA 01890
$1,627,000 | 73 Grove Street, Winchester, MA 01890
$1,627,000 | 73 Grove Street, Winchester, MA 01890
$1,627,000 | 73 Grove Street, Winchester, MA 01890
$1,627,000 | 73 Grove Street, Winchester, MA 01890
$1,627,000 | 73 Grove Street, Winchester, MA 01890
$1,627,000 | 73 Grove Street, Winchester, MA 01890
$1,627,000 | 73 Grove Street, Winchester, MA 01890
$1,627,000 | 73 Grove Street, Winchester, MA 01890
$1,627,000 | 73 Grove Street, Winchester, MA 01890
$1,627,000 | 73 Grove Street, Winchester, MA 01890
$1,627,000 | 73 Grove Street, Winchester, MA 01890
$1,627,000 | 73 Grove Street, Winchester, MA 01890
$1,627,000 | 73 Grove Street, Winchester, MA 01890
$1,627,000 | 73 Grove Street, Winchester, MA 01890
$1,627,000 | 73 Grove Street, Winchester, MA 01890
$1,627,000 | 73 Grove Street, Winchester, MA 01890
$1,627,000 | 73 Grove Street, Winchester, MA 01890
$1,627,000 | 73 Grove Street, Winchester, MA 01890
$1,627,000 | 73 Grove Street, Winchester, MA 01890
$1,627,000 | 73 Grove Street, Winchester, MA 01890
$1,627,000 | 73 Grove Street, Winchester, MA 01890
$1,627,000 | 73 Grove Street, Winchester, MA 01890
$1,627,000 | 73 Grove Street, Winchester, MA 01890
$1,627,000 | 73 Grove Street, Winchester, MA 01890
$1,627,000 | 73 Grove Street, Winchester, MA 01890
$1,627,000 | 73 Grove Street, Winchester, MA 01890
$1,627,000 | 73 Grove Street, Winchester, MA 01890
$1,627,000 | 73 Grove Street, Winchester, MA 01890
$1,627,000 | 73 Grove Street, Winchester, MA 01890
$1,627,000 | 73 Grove Street, Winchester, MA 01890
1/36
Sold 12/1/25

$1,627,000

4
Bedrooms
3,279
Square Feet
0.27
Acres

73 Grove Street, Winchester, MA 01890

$1,038,500 | 41 Englewood Road, Winchester, MA 01890
$1,038,500 | 41 Englewood Road, Winchester, MA 01890
$1,038,500 | 41 Englewood Road, Winchester, MA 01890
$1,038,500 | 41 Englewood Road, Winchester, MA 01890
$1,038,500 | 41 Englewood Road, Winchester, MA 01890
$1,038,500 | 41 Englewood Road, Winchester, MA 01890
$1,038,500 | 41 Englewood Road, Winchester, MA 01890
$1,038,500 | 41 Englewood Road, Winchester, MA 01890
$1,038,500 | 41 Englewood Road, Winchester, MA 01890
$1,038,500 | 41 Englewood Road, Winchester, MA 01890
$1,038,500 | 41 Englewood Road, Winchester, MA 01890
$1,038,500 | 41 Englewood Road, Winchester, MA 01890
$1,038,500 | 41 Englewood Road, Winchester, MA 01890
$1,038,500 | 41 Englewood Road, Winchester, MA 01890
$1,038,500 | 41 Englewood Road, Winchester, MA 01890
$1,038,500 | 41 Englewood Road, Winchester, MA 01890
$1,038,500 | 41 Englewood Road, Winchester, MA 01890
1/17
Sold 12/1/25

$1,038,500

3
Bedrooms
1,683
Square Feet
0.30
Acres

41 Englewood Road, Winchester, MA 01890

Sold 12/12/25

$1,050,000

2
Bedrooms
1
Bathrooms
1,177
Square Feet
0.35
Acres

7 Polk Road, Winchester, MA 01890

a front view of a house with a yard
Sold 12/22/25

$1,070,000

2
Bedrooms
1,666
Square Feet
0.23
Acres

26 N Gateway, Winchester, MA 01890

$1,392,500 | 53 Bacon Street, Winchester, MA 01890
$1,392,500 | 53 Bacon Street, Winchester, MA 01890
$1,392,500 | 53 Bacon Street, Winchester, MA 01890
$1,392,500 | 53 Bacon Street, Winchester, MA 01890
$1,392,500 | 53 Bacon Street, Winchester, MA 01890
$1,392,500 | 53 Bacon Street, Winchester, MA 01890
$1,392,500 | 53 Bacon Street, Winchester, MA 01890
$1,392,500 | 53 Bacon Street, Winchester, MA 01890
$1,392,500 | 53 Bacon Street, Winchester, MA 01890
$1,392,500 | 53 Bacon Street, Winchester, MA 01890
$1,392,500 | 53 Bacon Street, Winchester, MA 01890
$1,392,500 | 53 Bacon Street, Winchester, MA 01890
$1,392,500 | 53 Bacon Street, Winchester, MA 01890
$1,392,500 | 53 Bacon Street, Winchester, MA 01890
$1,392,500 | 53 Bacon Street, Winchester, MA 01890
$1,392,500 | 53 Bacon Street, Winchester, MA 01890
$1,392,500 | 53 Bacon Street, Winchester, MA 01890
$1,392,500 | 53 Bacon Street, Winchester, MA 01890
$1,392,500 | 53 Bacon Street, Winchester, MA 01890
$1,392,500 | 53 Bacon Street, Winchester, MA 01890
$1,392,500 | 53 Bacon Street, Winchester, MA 01890
$1,392,500 | 53 Bacon Street, Winchester, MA 01890
$1,392,500 | 53 Bacon Street, Winchester, MA 01890
$1,392,500 | 53 Bacon Street, Winchester, MA 01890
$1,392,500 | 53 Bacon Street, Winchester, MA 01890
$1,392,500 | 53 Bacon Street, Winchester, MA 01890
$1,392,500 | 53 Bacon Street, Winchester, MA 01890
$1,392,500 | 53 Bacon Street, Winchester, MA 01890
$1,392,500 | 53 Bacon Street, Winchester, MA 01890
$1,392,500 | 53 Bacon Street, Winchester, MA 01890
$1,392,500 | 53 Bacon Street, Winchester, MA 01890
$1,392,500 | 53 Bacon Street, Winchester, MA 01890
$1,392,500 | 53 Bacon Street, Winchester, MA 01890
1/33
Sold 1/9/26

$1,392,500

3
Bedrooms
2,865
Square Feet
0.28
Acres

53 Bacon Street, Winchester, MA 01890

a front view of a house with a yard
front view of a house with a yard
a kitchen with a sink and a refrigerator
a kitchen with stainless steel appliances granite countertop a sink and a stove
a kitchen with stainless steel appliances granite countertop a refrigerator a sink and a stove
a kitchen with stainless steel appliances granite countertop a sink a stove and a refrigerator
a view of a dining room with furniture window and wooden floor
a view of a dining room with furniture window and wooden floor
a view of a dining room with furniture window and wooden floor
a living room with furniture and a potted plant
a living room with furniture and a flat screen tv
a view of an entryway with wooden floor
a living room with furniture and a flat screen tv
a view of a livingroom with chair and table
a bedroom with a bed and large window
a work room with wooden floor and windows
a bathroom with a sink mirror and toilet
a bathroom with a sink toilet and shower
a bedroom with a bed and wooden floor
a bedroom with a bed and a lamp
a bedroom with a bed and a dresser
a bedroom with a bed and closet
an entryway with a door
a kitchen with a dining table chairs and white appliances
a kitchen with granite countertop a sink and a stove top oven with wooden cabinets
a kitchen with stainless steel appliances granite countertop a dining table chairs a sink and dishwasher a refrigerator with wooden floor
a kitchen with a sink a oven a refrigerator a stove and a window
a view of a dining room with furniture window and wooden floor
a view of a dining room with furniture and a chandelier
a living room with furniture and a flat screen tv
a living room with furniture and a flat screen tv
a bedroom with a bed and a window
a bedroom with a bed and wooden floor
a bedroom with a bed and a television
a bed sitting in a bedroom next to a window
a bathroom with a sink and mirror
a bathroom with a shower and a sink
a view of workspace with furniture and windows
a front view of a house with a yard
a front view of a house with a yard
$1,200,000 | 415-417 Washington Street, Winchester, MA 01890
1/41
Sold 11/21/25Virtual Tour

$1,200,000

5
Bedrooms
2,610
Square Feet
0.11
Acres

415-417 Washington Street, Winchester, MA 01890

a front view of a house with swimming pool
a front view of a house with a garden
a living room with furniture a fireplace a flat screen tv and windows
a living room with furniture and a wooden floor
a living room with furniture a flat screen tv and a fireplace
a living room with furniture a fireplace and a flat screen tv
a living room with furniture and a large window
a kitchen with stainless steel appliances granite countertop a dining table chairs and granite counter tops
a open kitchen with stainless steel appliances granite countertop a sink dishwasher stove and oven
a kitchen with stainless steel appliances granite countertop a sink refrigerator and cabinets
a kitchen with stainless steel appliances granite countertop a sink stove and refrigerator
a view of a dining room with furniture and wooden floor
a living room with furniture and a window
a view of a living room with a baby crib
a living room filled with furniture and a large window
a bedroom with a bed and wooden floor
a bedroom with a bed and a lamp next to a window
a view of walk in closet with empty racks
a bathroom with a sink vanity and a mirror
a bathroom with a toilet sink and mirror
a bathroom with a glass shower door
a view of bathroom with bathtub and shower
a bedroom with a bed and a painting on the wall
a bedroom with a bed and a night stand
a bedroom with a bed and wooden floor
a bathroom with a sink a mirror and a shower
a bathroom with a sink a mirror and a shower
a utility room with dryer and washer
a view of backyard with table and chairs and wooden fence
a view of an empty room with window
a view of staircase with a rug
a front view of a house with a yard
1/32
Sold 11/21/25Virtual Tour

$999,999

3
Bedrooms
1,756
Square Feet

16 Park Avenue, Unit 2, Winchester, MA 01890

a front view of a house with a garden
a front view of a house
a view of a hallway with wooden floor and entryway
a living room with furniture and a table with wooden floor
a living room with furniture large window and a fireplace
a living room with furniture and a fireplace
a view of a living room and hardwood floor
a view of a dining room with furniture and window
a view of a dining room with furniture window and wooden floor
a dining room with furniture and window
a large kitchen with kitchen island a large counter top space a sink stainless steel appliances and cabinets
a kitchen with a table and chairs in it
a kitchen with sink stove and cabinets
a kitchen with stainless steel appliances granite countertop a stove a kitchen island a table and chairs
a living room with furniture and a flat screen tv
a living room with furniture and a large window
a view of a patio with couches chairs and wooden floor
a utility room with dryer washer and a window
a bathroom with a sink and a mirror
a bedroom with a bed lamp closet and window
a large bedroom with a bed wooden floor and table
a bathroom with a sink mirror toilet and bathtub
wooden floor in an empty room with a window
a living room with furniture and a window
a bathroom with a sink a toilet and shower
a living room with furniture a table and wooden floor
a spacious bedroom with a large bed and a chandelier
a bedroom with a large bed and a chandelier
a spacious bathroom with a double vanity sink a mirror a bathtub and
an empty room with wooden floor and windows
a view of an empty room with a window
a view of livingroom with window and wooden floor
a room with furniture and pool table
a view of walk in closet
a view of a street with buildings
a view of a house with a yard
a view of an house with backyard porch and furniture
view of outdoor space and yard
a view of a city
front view of a house with a yard
1/40
Sold 12/1/25

$2,030,000

6
Bedrooms
5,791
Square Feet
0.29
Acres

58 Bacon Street, Winchester, MA 01890

a living room with furniture and a lamp
a front view of a house with garden
a view of outdoor space with deck and furniture
a kitchen with stainless steel appliances kitchen island granite countertop a sink and a refrigerator
a kitchen with stainless steel appliances white cabinets and a refrigerator
a kitchen with a refrigerator and a cabinets
a living room with furniture and a fireplace
a living room with furniture and a large window
a living room with furniture and a fireplace
a dining room with furniture and window
a living room with fireplace furniture and a wooden floor
a bedroom with a bed and a lamp
a spacious bedroom with a bed and a large window
a spacious bathroom with a double vanity sink a mirror and a bathtub
a very nice looking room with a mirror
a bedroom with a bed rug and wooden floor
a bedroom with a bed and furniture
a bathroom with a sink a double vanity and a mirror
a bathroom with a toilet and a mirror
a view of a backyard with sitting area
a view of a house with a backyard
an aerial view of a houses with a yard
unknown
1/23
Sold 12/4/25

$950,000

3
Bedrooms
1,535
Square Feet

16 Park Avenue, Unit 1, Winchester, MA 01890

$2,630,000 | 10 Sheffield Road, Winchester, MA 01890
$2,630,000 | 10 Sheffield Road, Winchester, MA 01890
$2,630,000 | 10 Sheffield Road, Winchester, MA 01890
$2,630,000 | 10 Sheffield Road, Winchester, MA 01890
$2,630,000 | 10 Sheffield Road, Winchester, MA 01890
$2,630,000 | 10 Sheffield Road, Winchester, MA 01890
$2,630,000 | 10 Sheffield Road, Winchester, MA 01890
$2,630,000 | 10 Sheffield Road, Winchester, MA 01890
$2,630,000 | 10 Sheffield Road, Winchester, MA 01890
$2,630,000 | 10 Sheffield Road, Winchester, MA 01890
$2,630,000 | 10 Sheffield Road, Winchester, MA 01890
$2,630,000 | 10 Sheffield Road, Winchester, MA 01890
$2,630,000 | 10 Sheffield Road, Winchester, MA 01890
$2,630,000 | 10 Sheffield Road, Winchester, MA 01890
$2,630,000 | 10 Sheffield Road, Winchester, MA 01890
$2,630,000 | 10 Sheffield Road, Winchester, MA 01890
$2,630,000 | 10 Sheffield Road, Winchester, MA 01890
$2,630,000 | 10 Sheffield Road, Winchester, MA 01890
$2,630,000 | 10 Sheffield Road, Winchester, MA 01890
$2,630,000 | 10 Sheffield Road, Winchester, MA 01890
$2,630,000 | 10 Sheffield Road, Winchester, MA 01890
$2,630,000 | 10 Sheffield Road, Winchester, MA 01890
$2,630,000 | 10 Sheffield Road, Winchester, MA 01890
$2,630,000 | 10 Sheffield Road, Winchester, MA 01890
$2,630,000 | 10 Sheffield Road, Winchester, MA 01890
$2,630,000 | 10 Sheffield Road, Winchester, MA 01890
$2,630,000 | 10 Sheffield Road, Winchester, MA 01890
$2,630,000 | 10 Sheffield Road, Winchester, MA 01890
$2,630,000 | 10 Sheffield Road, Winchester, MA 01890
$2,630,000 | 10 Sheffield Road, Winchester, MA 01890
$2,630,000 | 10 Sheffield Road, Winchester, MA 01890
$2,630,000 | 10 Sheffield Road, Winchester, MA 01890
$2,630,000 | 10 Sheffield Road, Winchester, MA 01890
$2,630,000 | 10 Sheffield Road, Winchester, MA 01890
$2,630,000 | 10 Sheffield Road, Winchester, MA 01890
$2,630,000 | 10 Sheffield Road, Winchester, MA 01890
$2,630,000 | 10 Sheffield Road, Winchester, MA 01890
$2,630,000 | 10 Sheffield Road, Winchester, MA 01890
$2,630,000 | 10 Sheffield Road, Winchester, MA 01890
$2,630,000 | 10 Sheffield Road, Winchester, MA 01890
$2,630,000 | 10 Sheffield Road, Winchester, MA 01890
1/41
Sold 12/8/25Virtual Tour

$2,630,000

7
Bedrooms
5,864
Square Feet
0.28
Acres

10 Sheffield Road, Winchester, MA 01890

$899,000 | 60 Harvard Street, Winchester, MA 01890
$899,000 | 60 Harvard Street, Winchester, MA 01890
$899,000 | 60 Harvard Street, Winchester, MA 01890
$899,000 | 60 Harvard Street, Winchester, MA 01890
$899,000 | 60 Harvard Street, Winchester, MA 01890
$899,000 | 60 Harvard Street, Winchester, MA 01890
$899,000 | 60 Harvard Street, Winchester, MA 01890
$899,000 | 60 Harvard Street, Winchester, MA 01890
$899,000 | 60 Harvard Street, Winchester, MA 01890
$899,000 | 60 Harvard Street, Winchester, MA 01890
$899,000 | 60 Harvard Street, Winchester, MA 01890
$899,000 | 60 Harvard Street, Winchester, MA 01890
$899,000 | 60 Harvard Street, Winchester, MA 01890
$899,000 | 60 Harvard Street, Winchester, MA 01890
$899,000 | 60 Harvard Street, Winchester, MA 01890
$899,000 | 60 Harvard Street, Winchester, MA 01890
1/16
Sold 11/25/25

$899,000

4
Bedrooms
1,860
Square Feet
0.12
Acres

60 Harvard Street, Winchester, MA 01890

a view of yard with an outdoor seating
a front view of a house with a yard
front view of a house
a front view of a house with a yard and potted plants
a view of a porch with wooden floor and stairs
a view of lake and mountain view
a view of a hallway with wooden floor and staircase
a large kitchen with stainless steel appliances granite countertop a stove and a refrigerator
a kitchen with stainless steel appliances granite countertop a stove and a sink
a kitchen with a stove a refrigerator and a fireplace
a kitchen with stainless steel appliances granite countertop a stove a sink and a microwave
a view of closet with wooden floor
a living room with furniture and a fireplace
a living room with furniture and a fireplace
a view of a dining room with furniture window and wooden floor
a dining room with furniture a chandelier and wooden floor
a view of workspace with wooden floor and windows
a spacious bedroom with a bed and a window
a view of staircase with black and white walls
a view of a hallway view with staircase
a living room with furniture and a flat screen tv
a bathroom with a sink and shower
a bathroom with a granite countertop sink a mirror and shower
a spacious bedroom with a bed and a window
a bedroom with a bed and a chandelier
a bathroom with a granite countertop sink toilet a mirror and shower
a view of an empty room with window and closet area
an empty room with wooden floor and window
a kitchen with a sink and cabinets
a view of a livingroom with furniture and a window
a bathroom with a sink toilet and shower
a view of a balcony with wooden floor and fence
a view of a house with a porch
unknown
a black and white photo of a bench
a front view of a house with a garden
a view of a yard with trees
a view of a pathway with a yard
a backyard of a house with large trees
a front view of a house with a yard
a view of a backyard with garden
$1,850,000 | 77A Brooks Street, Winchester, MA 01890
1/42
Sold 1/15/26Virtual Tour

$1,850,000

6
Bedrooms
4,122
Square Feet
0.63
Acres

77A Brooks Street, Winchester, MA 01890

a front view of a house with a yard
a front view of a house with a garden
a living room with furniture a table and a window
a living room with furniture and a window
a dining room with wooden floor a chandelier a glass table and chairs
a dining room with furniture a chandelier and wooden floor
a dining room with furniture and window
a large kitchen with granite countertop a stove a sink and a microwave
a large white kitchen with lots of counter space a sink and appliances
a workspace with wooden floor and a window
a living room with furniture a fireplace and a flat screen tv
a living room with furniture a fireplace and a flat screen tv
a living room with furniture and a large window
a living room with furniture and a flat screen tv
a bathroom with a sink and a mirror
a spacious bedroom with a bed a couch and potted plant on the dresser
a bedroom with a bed and wooden floor
a bathroom with a granite countertop sink toilet and shower
a view of an empty room with a window and wooden floor
wooden floor in an empty room with a window
a bathroom with a granite countertop sink toilet and a mirror
a view of an empty room with wooden floor and a window
an empty room with wooden floor and windows
a view of an empty room
a view of an empty room with wooden floor and a window
a bathroom with a granite countertop toilet a sink a mirror and a window
a view of empty room with wooden floor and fan
a view of an empty room with wooden floor
a view of an empty room
a view of an empty room with windows
a bathroom with a toilet a sink and mirror
a view of balcony with wooden floor
a front view of a house with garden
a picture of a bench in a white building
a picture of a floor plan
a picture of a wall with a white wall and a painting
unknown
1/37
Sold 11/10/25

$1,610,000

5
Bedrooms
3,508
Square Feet
0.30
Acres

166 Forest Street, Winchester, MA 01890

$2,250,000 | 14 Grant Road, Winchester, MA 01890
$2,250,000 | 14 Grant Road, Winchester, MA 01890
$2,250,000 | 14 Grant Road, Winchester, MA 01890
$2,250,000 | 14 Grant Road, Winchester, MA 01890
$2,250,000 | 14 Grant Road, Winchester, MA 01890
$2,250,000 | 14 Grant Road, Winchester, MA 01890
$2,250,000 | 14 Grant Road, Winchester, MA 01890
$2,250,000 | 14 Grant Road, Winchester, MA 01890
$2,250,000 | 14 Grant Road, Winchester, MA 01890
$2,250,000 | 14 Grant Road, Winchester, MA 01890
$2,250,000 | 14 Grant Road, Winchester, MA 01890
$2,250,000 | 14 Grant Road, Winchester, MA 01890
$2,250,000 | 14 Grant Road, Winchester, MA 01890
$2,250,000 | 14 Grant Road, Winchester, MA 01890
$2,250,000 | 14 Grant Road, Winchester, MA 01890
$2,250,000 | 14 Grant Road, Winchester, MA 01890
$2,250,000 | 14 Grant Road, Winchester, MA 01890
$2,250,000 | 14 Grant Road, Winchester, MA 01890
$2,250,000 | 14 Grant Road, Winchester, MA 01890
$2,250,000 | 14 Grant Road, Winchester, MA 01890
$2,250,000 | 14 Grant Road, Winchester, MA 01890
$2,250,000 | 14 Grant Road, Winchester, MA 01890
$2,250,000 | 14 Grant Road, Winchester, MA 01890
$2,250,000 | 14 Grant Road, Winchester, MA 01890
$2,250,000 | 14 Grant Road, Winchester, MA 01890
$2,250,000 | 14 Grant Road, Winchester, MA 01890
$2,250,000 | 14 Grant Road, Winchester, MA 01890
$2,250,000 | 14 Grant Road, Winchester, MA 01890
$2,250,000 | 14 Grant Road, Winchester, MA 01890
$2,250,000 | 14 Grant Road, Winchester, MA 01890
$2,250,000 | 14 Grant Road, Winchester, MA 01890
$2,250,000 | 14 Grant Road, Winchester, MA 01890
$2,250,000 | 14 Grant Road, Winchester, MA 01890
$2,250,000 | 14 Grant Road, Winchester, MA 01890
$2,250,000 | 14 Grant Road, Winchester, MA 01890
$2,250,000 | 14 Grant Road, Winchester, MA 01890
$2,250,000 | 14 Grant Road, Winchester, MA 01890
$2,250,000 | 14 Grant Road, Winchester, MA 01890
$2,250,000 | 14 Grant Road, Winchester, MA 01890
$2,250,000 | 14 Grant Road, Winchester, MA 01890
1/40
Sold 12/11/25Virtual Tour

$2,250,000

6
Bedrooms
4,200
Square Feet
0.23
Acres

14 Grant Road, Winchester, MA 01890

a front view of a house with a yard
a living room with furniture and wooden floor
a living room with furniture and a potted plant
a living room with furniture and painting on the wall
a living room with furniture and a potted plant
a kitchen with stainless steel appliances a stove a sink cabinets and a wooden floor
a kitchen with stainless steel appliances granite countertop white cabinets granite counter tops and a window
a kitchen with stainless steel appliances a sink a stove a refrigerator cabinets and dining table
a kitchen with stainless steel appliances granite countertop a stove top oven a sink dishwasher and a refrigerator
a kitchen with sink and cabinets
a view of a dining room with furniture and wooden floor
a view of a dining room with furniture and wooden floor
a view of a bathroom with a bath tub
a spacious bedroom with a large bed and wooden floor
a bedroom with a bed and a painting on the wall
a bed room with a bed and a window
a bathroom with a tub sink and mirror
a bathroom with a double vanity sink and a mirror
a bedroom with a bed and wooden floor
a bedroom with a bed and a window
a view of an empty room with wooden floor and a window
an empty room with wooden floor and windows
a bedroom with furniture and wooden floor
a bedroom with furniture and a window
a bathroom with a granite countertop sink mirror vanity and toilet
a bathroom with a window and a shower
a view of an empty room with wooden floor
an empty room with wooden floor and windows
a view of an empty room and wooden floor
a bathroom with a toilet sink and mirror
a storage room with washer and dryer
a view of a balcony with chairs and wooden fence
a view of a house with wooden deck
a view of a house with a large window
a front view of a house with a yard
a view of a house with a patio
a wooden bench covered with snow in front of house
a backyard of a house with a large tree
a view of a white house with a street
a front view of a house
a view of a house with snow on the road
1/41
Sold 2/4/26

$1,335,000

4
Bedrooms
2,854
Square Feet
0.21
Acres

112 Wendell Street, Winchester, MA 01890

a kitchen with a sink cabinets and wooden floor
a living room with a couch and a refrigerator
a living room with furniture and a large window
a living room with furniture a lamp and a kitchen view
a bathroom with a toilet and a sink
a bedroom with a bed and a desk
a bedroom with a bed and a chair in it
a view of a livingroom with washer and dryer
a living room with furniture and a chandelier
a sign that is on a street
a view of a sign under a large tree
a view of outdoor space with signage and flags
a view of swimming pool with a garden and plants
a view of a garden with a building in the background
a backyard of a house with a garden and plants
a view of a chair and table in the garden
a picture of street view
an aerial view of a house
an aerial view of residential houses with outdoor space and lake view
a view of a park with a large tree
a garden view with a fountain
a view of a park and trees
a view of a swimming pool with a yard
a view of a swimming pool with an outdoor space and seating area
a view of a pathway of a building
$340,000 | 200 Swanton Street, Unit 630, Winchester, MA 01890
1/26
Sold 2/2/26

$340,000

1
Bedrooms
613
Square Feet

200 Swanton Street, Unit 630, Winchester, MA 01890

 
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