Tori Gwin's Profile Photo

Tori Gwin

Licensed Real Estate Broker
tori.gwin@compass.com
M: 617-680-9515
O: 773-466-7150

Social Media



Client Testimonials

Scroll down for more

⭐⭐⭐⭐⭐
"Tori embodies what an integral Real Estate Broker is all about. She is trustworthy, diligent and pragmatic. All of her Clients have a positive experience which is why her business is growing by leaps and bounds. I cannot say enough about how great Tori is to work with. "-Larry

⭐⭐⭐⭐⭐
"Working with Tori was excellent! My wife and I were first-time home buyers and she was incredibly helpful at walking us through the process. She came prepared with comps, recommendations, and referrals for a great team. Tori was super communicative throughout our negotiations and closing which made for a super smooth home-buying experience - we cannot recommend her more!"-Miller

⭐⭐⭐⭐⭐
"My husband and I just moved to Chicago and did not know the area at all. Tori helped us fine an amazing apartment and rent it before the even happened! Knowing the area better now, I can't get over what an amazing find it was. I absolutely love it. She was so easy and fun to work with! I recommend her to anyone looking for a home!"-Anna

⭐⭐⭐⭐⭐
"Tori's positive energy made this process easy, and rubbed off on me to ease the anxiety of finding a new home. We are beyond grateful and I couldn’t be more excited for this journey we are going to embark on, and she was a part of it."-Mary

About Tori

Tori combines sharp market insight with a design-driven approach to help her clients buy, sell, and style homes that truly fit the way they live. Her thoughtful strategy, upbeat energy, and clear communication make the process feel seamless and even fun.

With a background in Psychology, Studio Art, and a Master’s in Education, Tori brings a mix of creativity, empathy, and organization to her work. She has an eye for design and a genuine love for helping people see not just what a home is, but what it could be.

Originally from Boston, Tori now calls Chicago home. As part of the top-producing Olive Well team at Compass, she pairs data and design to guide clients with confidence and care, from first-time buyers to seasoned sellers.

Her work has been featured in Real Producers, Chicago Agent Magazine, and the Emmy-nominated show The American Dream TV.

Tori lives in Logan Square with her husband, Chris, and their two kids, Will and Juniper. When she’s not working, she’s usually exploring new Chicago spots, gardening in her backyard, or spending as many weekends as possible on the East Coast soaking up Cape Cod.



olivewell.com

Tori Gwin’s Listings

a front view of a house
a living room with furniture and a flat screen tv
a living room with furniture and a flat screen tv
a view of a dining room with furniture and wooden floor
a kitchen with white cabinets and stainless steel appliances
a living room with stainless steel appliances kitchen island granite countertop a dining table chairs and view kitchen
a kitchen with stainless steel appliances granite countertop a table chairs sink refrigerator and cabinets
a kitchen with stainless steel appliances granite countertop a sink a stove a white cabinets and a window
a bathroom with a sink mirror and toilet
a view of an entryway with wooden floor
a bedroom with a bed and a window
a bathroom with a sink a toilet and shower
a bathroom with a sink and a mirror
a bathroom with a granite countertop sink mirror and toilet
a bedroom with a bed and a couch
a bathroom with a sink a toilet and shower
a living room with furniture
a living room with furniture and a couch
a view of workspace with gym equipment
a bedroom with a bed and a window
a bathroom with a sink a toilet and shower
a view of a bench in the balcony
a view of backyard with seating space and wooden fence
a picture of a bench in front of a wall
a picture of a floor plan
$835,000 | 3331 West Crystal Street, Chicago, IL 60651
$835,000 | 3331 West Crystal Street, Chicago, IL 60651
1/27
Listed By CompassContingent

$835,000

4
Bedrooms
3,100
Square Feet
0.73
Acres

3331 West Crystal Street, Chicago, IL 60651

$650,000 | 1012 South Loomis Street, Unit D, Chicago, IL 60607
$650,000 | 1012 South Loomis Street, Unit D, Chicago, IL 60607
$650,000 | 1012 South Loomis Street, Unit D, Chicago, IL 60607
$650,000 | 1012 South Loomis Street, Unit D, Chicago, IL 60607
$650,000 | 1012 South Loomis Street, Unit D, Chicago, IL 60607
$650,000 | 1012 South Loomis Street, Unit D, Chicago, IL 60607
$650,000 | 1012 South Loomis Street, Unit D, Chicago, IL 60607
$650,000 | 1012 South Loomis Street, Unit D, Chicago, IL 60607
$650,000 | 1012 South Loomis Street, Unit D, Chicago, IL 60607
$650,000 | 1012 South Loomis Street, Unit D, Chicago, IL 60607
$650,000 | 1012 South Loomis Street, Unit D, Chicago, IL 60607
$650,000 | 1012 South Loomis Street, Unit D, Chicago, IL 60607
$650,000 | 1012 South Loomis Street, Unit D, Chicago, IL 60607
$650,000 | 1012 South Loomis Street, Unit D, Chicago, IL 60607
$650,000 | 1012 South Loomis Street, Unit D, Chicago, IL 60607
$650,000 | 1012 South Loomis Street, Unit D, Chicago, IL 60607
$650,000 | 1012 South Loomis Street, Unit D, Chicago, IL 60607
1/17
Compass Coming Soon

$650,000

2
Bedrooms
1,800
Square Feet
0.04
Acres

1012 South Loomis Street, Unit D, Chicago, IL 60607

$485,000 | 2310 West Nelson Street, Unit 302, Chicago, IL 60618
$485,000 | 2310 West Nelson Street, Unit 302, Chicago, IL 60618
$485,000 | 2310 West Nelson Street, Unit 302, Chicago, IL 60618
$485,000 | 2310 West Nelson Street, Unit 302, Chicago, IL 60618
$485,000 | 2310 West Nelson Street, Unit 302, Chicago, IL 60618
$485,000 | 2310 West Nelson Street, Unit 302, Chicago, IL 60618
$485,000 | 2310 West Nelson Street, Unit 302, Chicago, IL 60618
$485,000 | 2310 West Nelson Street, Unit 302, Chicago, IL 60618
$485,000 | 2310 West Nelson Street, Unit 302, Chicago, IL 60618
$485,000 | 2310 West Nelson Street, Unit 302, Chicago, IL 60618
$485,000 | 2310 West Nelson Street, Unit 302, Chicago, IL 60618
$485,000 | 2310 West Nelson Street, Unit 302, Chicago, IL 60618
$485,000 | 2310 West Nelson Street, Unit 302, Chicago, IL 60618
$485,000 | 2310 West Nelson Street, Unit 302, Chicago, IL 60618
$485,000 | 2310 West Nelson Street, Unit 302, Chicago, IL 60618
$485,000 | 2310 West Nelson Street, Unit 302, Chicago, IL 60618
$485,000 | 2310 West Nelson Street, Unit 302, Chicago, IL 60618
$485,000 | 2310 West Nelson Street, Unit 302, Chicago, IL 60618
$485,000 | 2310 West Nelson Street, Unit 302, Chicago, IL 60618
$485,000 | 2310 West Nelson Street, Unit 302, Chicago, IL 60618
$485,000 | 2310 West Nelson Street, Unit 302, Chicago, IL 60618
1/21
Listed By CompassContingent ( Private )

$485,000

2
Bedrooms
Unavailable
Square Feet

2310 West Nelson Street, Unit 302, Chicago, IL 60618

$289,000 | 5 North Wabash Avenue, Unit 1103, Chicago, IL 60602
$289,000 | 5 North Wabash Avenue, Unit 1103, Chicago, IL 60602
$289,000 | 5 North Wabash Avenue, Unit 1103, Chicago, IL 60602
$289,000 | 5 North Wabash Avenue, Unit 1103, Chicago, IL 60602
$289,000 | 5 North Wabash Avenue, Unit 1103, Chicago, IL 60602
$289,000 | 5 North Wabash Avenue, Unit 1103, Chicago, IL 60602
$289,000 | 5 North Wabash Avenue, Unit 1103, Chicago, IL 60602
$289,000 | 5 North Wabash Avenue, Unit 1103, Chicago, IL 60602
$289,000 | 5 North Wabash Avenue, Unit 1103, Chicago, IL 60602
$289,000 | 5 North Wabash Avenue, Unit 1103, Chicago, IL 60602
$289,000 | 5 North Wabash Avenue, Unit 1103, Chicago, IL 60602
$289,000 | 5 North Wabash Avenue, Unit 1103, Chicago, IL 60602
$289,000 | 5 North Wabash Avenue, Unit 1103, Chicago, IL 60602
$289,000 | 5 North Wabash Avenue, Unit 1103, Chicago, IL 60602
$289,000 | 5 North Wabash Avenue, Unit 1103, Chicago, IL 60602
1/15
Listed By CompassContingent

$289,000

2
Bedrooms
1,195
Square Feet

5 North Wabash Avenue, Unit 1103, Chicago, IL 60602

Tori Gwin’s Transactions

Past Sales
a front view of a house

$2,350,000

6
Bedrooms
0.07
Acres

2240 West Belden Avenue, Chicago, IL 60647

a front view of a house with a yard and garage

$1,621,500

5
Bedrooms
5,760
Square Feet
72
Acres

1031 Prairie Lawn Road, Glenview, IL 60025

$1,575,000 | 2213 West Homer Street, Chicago, IL 60647

$1,575,000

5
Bedrooms
4,300
Square Feet
0.07
Acres

2213 West Homer Street, Chicago, IL 60647

a front view of a building with lot of cars and trees

$1,570,000

3
Bedrooms
2,321
Square Feet

40 North Carpenter Street, Unit PHN, Chicago, IL 60607

$1,525,000 | 2218 West Melrose Street, Chicago, IL 60618

$1,525,000

6
Bedrooms
5,000
Square Feet
0.07
Acres

2218 West Melrose Street, Chicago, IL 60618

$1,425,000 | 322 West Willow Street, Chicago, IL 60614

$1,425,000

4
Bedrooms
3,420
Square Feet
0.05
Acres

322 West Willow Street, Chicago, IL 60614

$1,415,000 | 555 Cherry Street, Winnetka, IL 60093

$1,415,000

5
Bedrooms
5,625
Square Feet

555 Cherry Street, Winnetka, IL 60093

a view of a brick building with many windows

$1,355,000

6
Bedrooms
0.07
Acres

2917 North Burling Street, Chicago, IL 60657

a front view of a house with a yard

$1,330,000

5
Bedrooms
0.07
Acres

2738 North Francisco Avenue, Chicago, IL 60647

a brick house with a small yard and large trees

$1,325,000

5
Bedrooms
0.07
Acres

1355 North Oakley Boulevard, Chicago, IL 60622

a front view of a building with street view

$1,300,000

3
Bedrooms
2,800
Square Feet

836 West Barry Avenue, Unit 3, Chicago, IL 60657

a view of a white house next to a yard

$1,285,000

4
Bedrooms
0.07
Acres

1720 North Campbell Avenue, Chicago, IL 60647

a front view of a house with a garden

$1,245,000

4
Bedrooms
3,175
Square Feet
0.11
Acres

2062 North Bingham Street, Chicago, IL 60647

front view of a brick house with a large windows

$1,185,000

4
Bedrooms
3,600
Square Feet
0.07
Acres

1632 North Bell Avenue, Chicago, IL 60647

a front view of a building

$1,137,500

3
Bedrooms
3,000
Square Feet

512 North McClurg Court, Unit 550607, Chicago, IL 60611

front view of a house with a yard

$1,100,000

5
Bedrooms
3,526
Square Feet
0.11
Acres

120 16th Street, Wilmette, IL 60091

$1,080,000 | 1529 West Roscoe Street, Unit 2, Chicago, IL 60657

$1,080,000

3
Bedrooms
2,400
Square Feet

1529 West Roscoe Street, Unit 2, Chicago, IL 60657

a front view of a house with a garden

$1,050,000

4
Bedrooms
3,876
Square Feet
0.07
Acres

1740 North Talman Avenue, Chicago, IL 60647

Past Rentals
a front view of a building

$6,500

3
Bedrooms
2,670
Square Feet

1755 North Winnebago Avenue, Chicago, IL 60647

a view of building with outdoor space

$5,750

3
Bedrooms
3,200
Square Feet

1 North Bishop Street, Unit 15, Chicago, IL 60607

$5,180

23 W Chicago Ave, Unit 4207

Chicago

$4,750 | 2815 North Maplewood Avenue, Chicago, IL 60618

$4,750

4
Bedrooms
3,300
Square Feet
0.07
Acres

2815 North Maplewood Avenue, Chicago, IL 60618

a front view of a building with a street

$4,600

3
Bedrooms
2,200
Square Feet

761 West Melrose Street, Chicago, IL 60657

a front view of a building

$4,500

3
Bedrooms
1,850
Square Feet

1550 North Lake Shore Drive, Unit 3G, Chicago, IL 60610

$4,300 | 451 West Huron Street, Unit 1108, Chicago, IL 60654

$4,300

2
Bedrooms
1,259
Square Feet

451 West Huron Street, Unit 1108, Chicago, IL 60654

front view of a building

$4,000

2
Bedrooms
1,412
Square Feet

1033 West Newport Avenue, Unit 3, Chicago, IL 60657

a view of entry way with wooden floor

$4,000

2
Bedrooms

2719 North Halsted Street, Unit 4, Chicago, IL 60614

$3,990 | 2247 West Armitage Avenue, Unit 1, Chicago, IL 60647

$3,990

3
Bedrooms
2,288
Square Feet

2247 West Armitage Avenue, Unit 1, Chicago, IL 60647

a front view of a house with garage

$3,850

3
Bedrooms
1,500
Square Feet

3119 North Racine Avenue, Unit CH, Chicago, IL 60657

$3,600 | 3425 North Seminary Avenue, Unit 2F, Chicago, IL 60657

$3,600

4
Bedrooms
2,200
Square Feet
0.07
Acres

3425 North Seminary Avenue, Unit 2F, Chicago, IL 60657

$3,525 | 313 W Wolf Point Plz, Unit 3309 | Chicago

$3,525

313 W Wolf Point Plz, Unit 3309

Chicago

a front view of a building with glass windows

$3,500

3
Bedrooms
2,000
Square Feet

958 North Wolcott Avenue, Unit 1, Chicago, IL 60622

$3,467 | 365 N Jefferson St, Unit 0507

$3,467

365 N Jefferson St, Unit 0507

$3,300 | 3307 North Southport Avenue, Unit 1F, Chicago, IL 60657

$3,300

3
Bedrooms
2,000
Square Feet

3307 North Southport Avenue, Unit 1F, Chicago, IL 60657