Specialties

Buyer's Agent
Listing Agent
Relocation Specialist
Tenant/Landlord Specialist
About Ashley

Ashley Leavitt is a successful REALTOR® with deep expertise in the Chicagoland real estate market. She takes great pride in living and working in a region full of opportunity and charm. After spending over a decade in Roscoe Village and recently relocating to Glenview, Ashley brings valuable insight into the unique character of both the city and its surrounding suburbs—making her especially skilled at helping clients transition seamlessly from urban to suburban living.

With over 10 years of experience, Ashley is a wealth of knowledge for both first-time homebuyers and seasoned sellers. She understands that every client’s journey is unique and is committed to providing thoughtful guidance, clear communication, and expert negotiation every step of the way. Whether it’s navigating the competitive city market or finding the perfect fit in the suburbs, Ashley works tirelessly to ensure your next real estate adventure is as easy, enjoyable, and stress-free as possible.

Ashley is an active member of the Chicago Association of REALTORS® (CAR), Friends of Downtown Glenview, and the District 34 PTA. She’s passionate about strengthening the local community and enjoys volunteering with Friends of Downtown Glenview—a nonprofit, resident-led group focused on creating a vibrant, thriving downtown district. She also volunteers with Ronald McDonald House Charities, preparing meals for families of children receiving care at Lurie Children's Hospital.

Ashley earned her Bachelor of Science degree from Minnesota State University, Mankato, graduating at the top of her class. In her free time, she enjoys cooking, staying active, traveling, and spending time with her husband Scotty, their three children—Maverick, Savannah, and Ryder—and their beloved pup, Gunner.

Ashley Leavitt’s Listings

$789,000 | 4043 North Damen Avenue, Unit 4, Chicago, IL 60618
$789,000 | 4043 North Damen Avenue, Unit 4, Chicago, IL 60618
$789,000 | 4043 North Damen Avenue, Unit 4, Chicago, IL 60618
$789,000 | 4043 North Damen Avenue, Unit 4, Chicago, IL 60618
$789,000 | 4043 North Damen Avenue, Unit 4, Chicago, IL 60618
$789,000 | 4043 North Damen Avenue, Unit 4, Chicago, IL 60618
$789,000 | 4043 North Damen Avenue, Unit 4, Chicago, IL 60618
$789,000 | 4043 North Damen Avenue, Unit 4, Chicago, IL 60618
$789,000 | 4043 North Damen Avenue, Unit 4, Chicago, IL 60618
$789,000 | 4043 North Damen Avenue, Unit 4, Chicago, IL 60618
$789,000 | 4043 North Damen Avenue, Unit 4, Chicago, IL 60618
$789,000 | 4043 North Damen Avenue, Unit 4, Chicago, IL 60618
$789,000 | 4043 North Damen Avenue, Unit 4, Chicago, IL 60618
$789,000 | 4043 North Damen Avenue, Unit 4, Chicago, IL 60618
$789,000 | 4043 North Damen Avenue, Unit 4, Chicago, IL 60618
$789,000 | 4043 North Damen Avenue, Unit 4, Chicago, IL 60618
$789,000 | 4043 North Damen Avenue, Unit 4, Chicago, IL 60618
$789,000 | 4043 North Damen Avenue, Unit 4, Chicago, IL 60618
$789,000 | 4043 North Damen Avenue, Unit 4, Chicago, IL 60618
$789,000 | 4043 North Damen Avenue, Unit 4, Chicago, IL 60618
$789,000 | 4043 North Damen Avenue, Unit 4, Chicago, IL 60618
$789,000 | 4043 North Damen Avenue, Unit 4, Chicago, IL 60618
$789,000 | 4043 North Damen Avenue, Unit 4, Chicago, IL 60618
$789,000 | 4043 North Damen Avenue, Unit 4, Chicago, IL 60618
$789,000 | 4043 North Damen Avenue, Unit 4, Chicago, IL 60618
$789,000 | 4043 North Damen Avenue, Unit 4, Chicago, IL 60618
$789,000 | 4043 North Damen Avenue, Unit 4, Chicago, IL 60618
$789,000 | 4043 North Damen Avenue, Unit 4, Chicago, IL 60618
$789,000 | 4043 North Damen Avenue, Unit 4, Chicago, IL 60618
$789,000 | 4043 North Damen Avenue, Unit 4, Chicago, IL 60618
$789,000 | 4043 North Damen Avenue, Unit 4, Chicago, IL 60618
1/31
Listed By CompassContingent

$789,000

3
Bedrooms
1,939
Square Feet
a view of a building from a balcony
a view of a brick building with many windows
a living room with furniture a flat screen tv and a fireplace
a living room with furniture and a rug
a living room with furniture and a wooden floor
a living room with furniture fireplace and a flat screen tv
a kitchen with stainless steel appliances kitchen island granite countertop a stove top oven a sink with white cabinets and wooden floor
a large kitchen with stainless steel appliances granite countertop a stove and a sink
a kitchen with stainless steel appliances granite countertop a refrigerator and a stove
a kitchen with stainless steel appliances granite countertop a stove and a refrigerator
a view of a dining room with furniture
a view of a a dining room with furniture window and wooden floor
a bathroom with a sink a toilet and mirror
a view of balcony with outdoor seating
a spacious bedroom with a large bed and a chandelier
a bedroom with a bed and a flat screen tv
a spacious bathroom with a double vanity sink mirror and toilet
a bathroom with a shower
a bedroom with a bed and a flat screen tv
a bedroom with a bed and wooden floor
a bathroom with a bathtub sink and mirror
a bedroom with a bed and wooden floor
a view of a hallway with wooden floor and windows
a bathroom with a sink a toilet and shower
a utility room with dryer and washer
a roof deck with a dining table and chairs with potted plants
a patio with glass top table and chairs and potted plants
a picture of a floor plan
a view of a room with a small window
$750,000 | 2851 North Damen Avenue, Unit 1, Chicago, IL 60618
$750,000 | 2851 North Damen Avenue, Unit 1, Chicago, IL 60618
1/31
Listed By CompassContingent

$750,000

3
Bedrooms
2,183
Square Feet
a front view of a house with garden
a front view of a house with a outdoor space
a view of the door of the house
a view of an empty room
a living room with furniture and window
a living room with furniture and a couch
a view of a dining room with furniture window and outside view
a view of a dining room with furniture and chandelier
a kitchen with stainless steel appliances a white cabinets and wooden floor
a kitchen with stainless steel appliances kitchen island granite countertop a refrigerator and a stove
a kitchen with cabinets appliances and a ceiling fan
a dining room with furniture and window
a room with toys and books on the wall
a bathroom with a sink a toilet and a mirror
a spacious bedroom with a bed and glass window
a bedroom with a bed mirror and window
a bathroom with a granite countertop sink a toilet and shower
a view of a balcony with ocean view
a view of a lake from a balcony
a bedroom with a bed and a table
a bedroom with a bed and a chandelier
a living room with furniture and a flat screen tv
a bathroom with a mirror and sink
a living room with furniture and a large window
a living room with furniture and a large window
a bed room with furniture and a table
a living room with furniture gym equipment and a view of living room
a living room with furniture and a table
a utility room with cabinets and window
a living room with furniture and a large window
a living room with furniture toys and a large window
a utility room with dryer and washer
a view of balcony with outdoor seating and city view
a view of swimming pool with a balcony
a view of a lake with houses in the background
a front view of a house with a yard
a view of a terrace
a swimming pool with outdoor seating and yard
a view of a lake with houses
a view of a lake with houses in the background
a view of a lake with houses in the background
a view of a lake with houses in the back
a view of a lake with a terrace
a picture of a bathroom with a sink and mirror
a picture of floor plan
$650,000 | 1309 Montgomery Drive, Deerfield, IL 60015
1/46
Listed By CompassContingent

$650,000

5
Bedrooms
4,856
Square Feet
0.26
Acres

Ashley Leavitt’s Transactions

Past Sales
a front view of a house with garden

$3,740,000

8
Bedrooms
9,557
Square Feet
0.85
Acres
$1,829,000 | 160 Linden Avenue, Glencoe, IL 60022

$1,829,000

5
Bedrooms
3,803
Square Feet
0.29
Acres
front view of a house with a yard

$1,435,000

6
Bedrooms
4,000
Square Feet
0.09
Acres
front view of brick house with a yard

$1,225,000

3
Bedrooms
3,061
Square Feet
0.26
Acres
$1,030,000 | 2634 North Ashland Avenue, Unit 2, Chicago, IL 60614

$1,030,000

4
Bedrooms
3,174
Square Feet
a front view of a house with a garden

$970,000

3
Bedrooms
2,397
Square Feet
0.06
Acres
a view of a house with garden and plants

$895,000

4
Bedrooms
2,344
Square Feet
0.17
Acres
a front view of a house with garden

$885,000

5
Bedrooms
3,695
Square Feet
0.34
Acres
a front view of a house with a garden

$880,000

5
Bedrooms
4,297
Square Feet
0.3
Acres
front view of a house with a yard

$860,000

4
Bedrooms
4,118
Square Feet
0.51
Acres
$859,000 | 4007 North Paulina Street, Unit 1S, Chicago, IL 60613

$859,000

4
Bedrooms
3,100
Square Feet
$850,000 | 2839 North Wolcott Avenue, Unit E, Chicago, IL 60657

$850,000

4
Bedrooms
2,405
Square Feet
0.05
Acres
a front view of a building with a lot of windows

$825,000

3
Bedrooms
a front view of house with yard

$817,000

5
Bedrooms
5,362
Square Feet
0.35
Acres
a view of a white house with a large tree and wooden fence

$790,000

3
Bedrooms
3,258
Square Feet
0.08
Acres
a front view of a house with a yard

$725,000

4
Bedrooms
3,459
Square Feet
0.46
Acres
front view of a building with a street

$717,500

2
Bedrooms
1,319
Square Feet
$710,000 | 3546 West Shakespeare Avenue, Chicago, IL 60647

$710,000

5
Bedrooms
0.07
Acres
Past Rentals
a front view of a house with a yard

$4,850

4
Bedrooms
2,336
Square Feet
front view of a building

$3,850

2
Bedrooms
1,100
Square Feet
$2,500 | 1445 North California Avenue, Unit 1, Chicago, IL 60622

$2,500

3
Bedrooms
1,100
Square Feet
a front view of a house

$2,250

3
Bedrooms
1,300
Square Feet
a front view of a brick building

$2,200

3
Bedrooms
1,100
Square Feet
a front view of a building with retail shops

$2,200

1
Bedrooms
1,000
Square Feet
a front view of a multi story building with a yard

$2,100

3
Bedrooms
1,100
Square Feet
a view of a building from a balcony

$1,995

1
Bedrooms
$1,800 | 1445 North California Avenue, Unit GARDEN, Chicago, IL 60622

$1,800

2
Bedrooms
1,100
Square Feet
$1,500 | 59 East Cedar Street, Unit 3B, Chicago, IL 60611

$1,500

1
Bedrooms
$1,375 | 1433 North California Avenue, Unit GARDEN, Chicago, IL 60622

$1,375

2
Bedrooms
0.07
Acres