Jordan Pyle's Profile Photo

Jordan Pyle

Licensed Real Estate Agent

Awards

- National Association of Realtors - 30 Under 30 (2020)
- Agent Member of The Gulf Coast Collective:
Real Trends Verified 2025 - Top 1.5% Small Team in the Nation by Sales Volume
Real Trends Verified 2025 - The Thousand - #561 of the top 1000 small teams by sales volume 

Specialties

Second Homes | Investment Properties
Waterfront & Lifestyle Communities

Involvement:
Compass Young Professionals - Founder & Co-National Director
About Jordan

Jordan Pyle is a seasoned real estate expert with over 12 years of experience, proudly licensed in both Florida and Illinois. This dual-market advantage allows him to serve clients across Southwest Florida and the city of Chicago, with a particular focus on those seeking second homes, investment properties or relocation needs in either market. 

Jordan began his real estate journey in Chicago in 2014, where he built a successful business as the founder of PYLE Residential, representing buyers, sellers, and investors throughout the city. His mission from day one has been clear: ā€œBuild Community & Foster Infinite Possibility through Real Estate.ā€

Today, Jordan resides in Naples, Florida, and is a key member of The Gulf Coast Collective under team lead Madeline Tracy. His ability to seamlessly bridge two distinct markets makes him an invaluable asset for clients transitioning between city life and coastal living.  Being born and raised for 34 years in the midwest allowed Jordan to cultivate a robust network that makes his reach and exposure for clients undeniable and a true value-add to their buying or selling journey here in Naples.

A recipient of the National Association of Realtors’ 30 Under 30 award, Jordan is a consistent top producer recognized for his leadership, innovation, and drive. He’s also the Founder & National Director of Compass Young Professionals, where he helps shape the next generation of real estate leaders.

Jordan is known for his exceptional customer service, strategic marketing, and calm, collaborative approach. He combines deep market knowledge with digital expertise to help sellers achieve top-dollar results and guide buyers through fast-moving, competitive markets.

Whether you're buying, selling, relocating, or investing—Jordan is here to help. Feel free to reach out with any real estate questions. He looks forward to connecting with you!


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312-805-7074
Jordan.Pyle@Compass.com

Jordan Pyle’s Listings

$2,100,000 | 26384 Augusta Creek Court, Bonita Springs, FL 34134
$2,100,000 | 26384 Augusta Creek Court, Bonita Springs, FL 34134
$2,100,000 | 26384 Augusta Creek Court, Bonita Springs, FL 34134
$2,100,000 | 26384 Augusta Creek Court, Bonita Springs, FL 34134
$2,100,000 | 26384 Augusta Creek Court, Bonita Springs, FL 34134
$2,100,000 | 26384 Augusta Creek Court, Bonita Springs, FL 34134
$2,100,000 | 26384 Augusta Creek Court, Bonita Springs, FL 34134
$2,100,000 | 26384 Augusta Creek Court, Bonita Springs, FL 34134
$2,100,000 | 26384 Augusta Creek Court, Bonita Springs, FL 34134
$2,100,000 | 26384 Augusta Creek Court, Bonita Springs, FL 34134
$2,100,000 | 26384 Augusta Creek Court, Bonita Springs, FL 34134
$2,100,000 | 26384 Augusta Creek Court, Bonita Springs, FL 34134
$2,100,000 | 26384 Augusta Creek Court, Bonita Springs, FL 34134
$2,100,000 | 26384 Augusta Creek Court, Bonita Springs, FL 34134
$2,100,000 | 26384 Augusta Creek Court, Bonita Springs, FL 34134
$2,100,000 | 26384 Augusta Creek Court, Bonita Springs, FL 34134
$2,100,000 | 26384 Augusta Creek Court, Bonita Springs, FL 34134
$2,100,000 | 26384 Augusta Creek Court, Bonita Springs, FL 34134
$2,100,000 | 26384 Augusta Creek Court, Bonita Springs, FL 34134
$2,100,000 | 26384 Augusta Creek Court, Bonita Springs, FL 34134
$2,100,000 | 26384 Augusta Creek Court, Bonita Springs, FL 34134
$2,100,000 | 26384 Augusta Creek Court, Bonita Springs, FL 34134
$2,100,000 | 26384 Augusta Creek Court, Bonita Springs, FL 34134
$2,100,000 | 26384 Augusta Creek Court, Bonita Springs, FL 34134
$2,100,000 | 26384 Augusta Creek Court, Bonita Springs, FL 34134
$2,100,000 | 26384 Augusta Creek Court, Bonita Springs, FL 34134
$2,100,000 | 26384 Augusta Creek Court, Bonita Springs, FL 34134
$2,100,000 | 26384 Augusta Creek Court, Bonita Springs, FL 34134
$2,100,000 | 26384 Augusta Creek Court, Bonita Springs, FL 34134
$2,100,000 | 26384 Augusta Creek Court, Bonita Springs, FL 34134
$2,100,000 | 26384 Augusta Creek Court, Bonita Springs, FL 34134
$2,100,000 | 26384 Augusta Creek Court, Bonita Springs, FL 34134
$2,100,000 | 26384 Augusta Creek Court, Bonita Springs, FL 34134
$2,100,000 | 26384 Augusta Creek Court, Bonita Springs, FL 34134
$2,100,000 | 26384 Augusta Creek Court, Bonita Springs, FL 34134
$2,100,000 | 26384 Augusta Creek Court, Bonita Springs, FL 34134
$2,100,000 | 26384 Augusta Creek Court, Bonita Springs, FL 34134
$2,100,000 | 26384 Augusta Creek Court, Bonita Springs, FL 34134
$2,100,000 | 26384 Augusta Creek Court, Bonita Springs, FL 34134
$2,100,000 | 26384 Augusta Creek Court, Bonita Springs, FL 34134
$2,100,000 | 26384 Augusta Creek Court, Bonita Springs, FL 34134
$2,100,000 | 26384 Augusta Creek Court, Bonita Springs, FL 34134
$2,100,000 | 26384 Augusta Creek Court, Bonita Springs, FL 34134
$2,100,000 | 26384 Augusta Creek Court, Bonita Springs, FL 34134
$2,100,000 | 26384 Augusta Creek Court, Bonita Springs, FL 34134
$2,100,000 | 26384 Augusta Creek Court, Bonita Springs, FL 34134
1/46
Listed By CompassPending With Contingencies

$2,100,000

4
Bedrooms
2,990
Square Feet
0.38
Acres
$800,000 | 1882 North Poe Street, Chicago, IL 60614
$800,000 | 1882 North Poe Street, Chicago, IL 60614
$800,000 | 1882 North Poe Street, Chicago, IL 60614
$800,000 | 1882 North Poe Street, Chicago, IL 60614
$800,000 | 1882 North Poe Street, Chicago, IL 60614
$800,000 | 1882 North Poe Street, Chicago, IL 60614
$800,000 | 1882 North Poe Street, Chicago, IL 60614
$800,000 | 1882 North Poe Street, Chicago, IL 60614
$800,000 | 1882 North Poe Street, Chicago, IL 60614
$800,000 | 1882 North Poe Street, Chicago, IL 60614
$800,000 | 1882 North Poe Street, Chicago, IL 60614
$800,000 | 1882 North Poe Street, Chicago, IL 60614
$800,000 | 1882 North Poe Street, Chicago, IL 60614
$800,000 | 1882 North Poe Street, Chicago, IL 60614
$800,000 | 1882 North Poe Street, Chicago, IL 60614
$800,000 | 1882 North Poe Street, Chicago, IL 60614
$800,000 | 1882 North Poe Street, Chicago, IL 60614
$800,000 | 1882 North Poe Street, Chicago, IL 60614
$800,000 | 1882 North Poe Street, Chicago, IL 60614
$800,000 | 1882 North Poe Street, Chicago, IL 60614
$800,000 | 1882 North Poe Street, Chicago, IL 60614
$800,000 | 1882 North Poe Street, Chicago, IL 60614
$800,000 | 1882 North Poe Street, Chicago, IL 60614
$800,000 | 1882 North Poe Street, Chicago, IL 60614
$800,000 | 1882 North Poe Street, Chicago, IL 60614
$800,000 | 1882 North Poe Street, Chicago, IL 60614
$800,000 | 1882 North Poe Street, Chicago, IL 60614
$800,000 | 1882 North Poe Street, Chicago, IL 60614
$800,000 | 1882 North Poe Street, Chicago, IL 60614
$800,000 | 1882 North Poe Street, Chicago, IL 60614
$800,000 | 1882 North Poe Street, Chicago, IL 60614
$800,000 | 1882 North Poe Street, Chicago, IL 60614
$800,000 | 1882 North Poe Street, Chicago, IL 60614
$800,000 | 1882 North Poe Street, Chicago, IL 60614
1/34
Listed By CompassContingent

$800,000

3
Bedrooms
Unavailable
Square Feet
0.03
Acres
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
$749,999 | 1196 Westlake Boulevard, Naples, FL 34103
1/49
Listed By CompassOpen: 4/26 01:00PM - 03:00PM

$749,999

4
Bedrooms
1,486
Square Feet
0.17
Acres
a living room with furniture kitchen view and a chandelier
a view of a house with a small yard and plants
an aerial view of residential houses with outdoor space and ocean view
a view of a house with a small yard and a palm tree
a view of a hallway with wooden floor and a bathroom view
a large living room with stainless steel appliances kitchen island granite countertop lots of white furniture a chandelier a large window and a chandelier
a living room with furniture and a flat screen tv
a living room with furniture kitchen and a chandelier
a living room with furniture and a flat screen tv
a living room with furniture a dining table and a chandelier
a living room with furniture and a flat screen tv
a living room with furniture a flat screen tv and kitchen view
a kitchen with stainless steel appliances granite countertop a sink a stove a refrigerator a microwave oven with white cabinets
a kitchen with stainless steel appliances granite countertop a sink and a white cabinets
a view of living room kitchen with stainless steel appliances granite countertop living room and living room
a large kitchen with stainless steel appliances lots of counter space and windows
a kitchen with stainless steel appliances granite countertop a sink a stove and a wooden floors
a kitchen with stainless steel appliances granite countertop a refrigerator a stove a microwave and a refrigerator
a kitchen with stainless steel appliances a refrigerator a stove a sink dishwasher and a fireplace with wooden floor
a dining room with furniture a potted plant and a chandelier
a dining room with furniture and window
a view of a dining room with furniture window and outside view
a outdoor view with a sitting space
a outdoor space with furniture
a view of a garden
a utility room with dryer and washer
a bedroom with a large bed and a window
a bedroom with a bed and a large window
a bedroom with a bed and a chandelier
a bedroom with a large bed and a window
a bathroom with a double vanity sink and mirror
a bathroom with a double vanity sink and a mirror
a spacious bathroom with double vanity a mirror and a shower
a bathroom with a shower
a bedroom with a bed and a potted plant
a bedroom with a bed and a mirror
a bathroom with a granite countertop sink and a mirror
a dining room with furniture and window
a view of a dining room with furniture
a workspace with furniture and window
a view of a house with a yard
a front view of a house with a garden
a view of a house with a backyard
a view of a house with a yard
a view of a golf course with a lake
a aerial view of a house with a garden and plants
a view of a big house with a big yard plants and large tree
a view of swimming pool with outdoor seating and city view
a view of a outdoor space with porch and patio
1/49
Listed By Compass

$599,000

3
Bedrooms
1,812
Square Feet
0.16
Acres
a kitchen with stainless steel appliances granite countertop a stove a sink a dining table and chairs with wooden floor
a front view of a house with a yard and garage
a view of a living room with a window
a view of kitchen with stainless steel appliances refrigerator stove microwave and cabinets
a kitchen with stainless steel appliances kitchen island granite countertop a dining table chairs stove refrigerator and cabinets
a kitchen with stainless steel appliances granite countertop a stove a refrigerator a microwave oven a sink with a dining table and chairs
a kitchen with stainless steel appliances a stove a sink a microwave a refrigerator and white cabinets with wooden floor
a living room with lots of furniture and a large window
a view of front door
a balcony with couch and city view
a bedroom with a large bed and a window
a bedroom with a bed and a television in it
a bathroom with double vanity sinks a vanity a lamp and a mirror
a bathroom with a shower
a view of a workspace with furniture and a window
a bathroom with a sink a toilet a mirror and shower curtain
a living room with furniture and a rug
a living room with furniture a flat screen tv and a fireplace
a view of entryway and workspace
front view of a house
an aerial view of residential houses with outdoor space and ocean view
a decorative lighting & window in a room
a kitchen with a window a sink and dining table view
a utility room with dryer and washer
a room with storage and a white refrigerator
an aerial view of residential houses with outdoor space and ocean view
a view of a city with a building in the background
$567,500 | 4620 Arboretum Circle, Unit 201, Naples, FL 34112
$567,500 | 4620 Arboretum Circle, Unit 201, Naples, FL 34112
$567,500 | 4620 Arboretum Circle, Unit 201, Naples, FL 34112
1/30
Listed By Compass

$567,500

2
Bedrooms
1,721
Square Feet
a front view of a house with a yard
a view of a house with backyard porch and sitting area
a kitchen with stainless steel appliances a refrigerator a stove a sink a dining table and chairs
a kitchen with stainless steel appliances granite countertop a refrigerator and a sink
a kitchen with stainless steel appliances a stove a sink dishwasher a refrigerator with a dining table and chairs
a kitchen with stainless steel appliances a stove a sink a microwave and cabinets
a bathroom with a sink and a mirror
a dining room with furniture and window
a very nice looking dining room with a large dining table and chairs
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 window
a living room with furniture and a flat screen tv
a living room with furniture a rug and a chandelier
a dining room with a table chairs and a dining table
a view of a dining room with furniture window and wooden floor
a bedroom with a bed and a large window
a bedroom with a bed and a chandelier
a bedroom with a bed couch and a walk in closet
a spacious bathroom with a double vanity sink mirror and toilet
a bedroom with bed and a window
a bedroom with a bed and a chandelier
a bathroom with a bathtub shower sink vanity mirror and toilet
a view of a chair and table in the balcony
a view of a two chairs in the balcony
a view of a porch with furniture and garden
a view of storage and utility room with washer and dryer
a kitchen with a refrigerator and a sink
a kitchen with a stove and a microwave
an aerial view of residential houses with outdoor space and trees
an aerial view of multiple house
an aerial view of multiple house
aerial view of a house with a patio
an aerial view of a city with lots of residential buildings ocean and mountain view in back
an aerial view of a house with a yard
an aerial view of a house with a yard
an aerial view of a houses with outdoor space
1/37
Listed By Compass

$319,900

2
Bedrooms
1,349
Square Feet
$104,900 | 43 Enchanting Boulevard, Unit E43, Naples, FL 34112
$104,900 | 43 Enchanting Boulevard, Unit E43, Naples, FL 34112
$104,900 | 43 Enchanting Boulevard, Unit E43, Naples, FL 34112
$104,900 | 43 Enchanting Boulevard, Unit E43, Naples, FL 34112
$104,900 | 43 Enchanting Boulevard, Unit E43, Naples, FL 34112
$104,900 | 43 Enchanting Boulevard, Unit E43, Naples, FL 34112
$104,900 | 43 Enchanting Boulevard, Unit E43, Naples, FL 34112
$104,900 | 43 Enchanting Boulevard, Unit E43, Naples, FL 34112
$104,900 | 43 Enchanting Boulevard, Unit E43, Naples, FL 34112
$104,900 | 43 Enchanting Boulevard, Unit E43, Naples, FL 34112
$104,900 | 43 Enchanting Boulevard, Unit E43, Naples, FL 34112
$104,900 | 43 Enchanting Boulevard, Unit E43, Naples, FL 34112
$104,900 | 43 Enchanting Boulevard, Unit E43, Naples, FL 34112
$104,900 | 43 Enchanting Boulevard, Unit E43, Naples, FL 34112
$104,900 | 43 Enchanting Boulevard, Unit E43, Naples, FL 34112
$104,900 | 43 Enchanting Boulevard, Unit E43, Naples, FL 34112
$104,900 | 43 Enchanting Boulevard, Unit E43, Naples, FL 34112
$104,900 | 43 Enchanting Boulevard, Unit E43, Naples, FL 34112
$104,900 | 43 Enchanting Boulevard, Unit E43, Naples, FL 34112
$104,900 | 43 Enchanting Boulevard, Unit E43, Naples, FL 34112
$104,900 | 43 Enchanting Boulevard, Unit E43, Naples, FL 34112
$104,900 | 43 Enchanting Boulevard, Unit E43, Naples, FL 34112
$104,900 | 43 Enchanting Boulevard, Unit E43, Naples, FL 34112
$104,900 | 43 Enchanting Boulevard, Unit E43, Naples, FL 34112
$104,900 | 43 Enchanting Boulevard, Unit E43, Naples, FL 34112
$104,900 | 43 Enchanting Boulevard, Unit E43, Naples, FL 34112
$104,900 | 43 Enchanting Boulevard, Unit E43, Naples, FL 34112
$104,900 | 43 Enchanting Boulevard, Unit E43, Naples, FL 34112
$104,900 | 43 Enchanting Boulevard, Unit E43, Naples, FL 34112
$104,900 | 43 Enchanting Boulevard, Unit E43, Naples, FL 34112
$104,900 | 43 Enchanting Boulevard, Unit E43, Naples, FL 34112
$104,900 | 43 Enchanting Boulevard, Unit E43, Naples, FL 34112
$104,900 | 43 Enchanting Boulevard, Unit E43, Naples, FL 34112
$104,900 | 43 Enchanting Boulevard, Unit E43, Naples, FL 34112
$104,900 | 43 Enchanting Boulevard, Unit E43, Naples, FL 34112
$104,900 | 43 Enchanting Boulevard, Unit E43, Naples, FL 34112
1/36
Listed By CompassPending With Contingencies

$104,900

2
Bedrooms
891
Square Feet

Jordan Pyle’s Transactions

Past Sales
front view of a house

$2,350,000

5
Bedrooms
0.07
Acres

$1,795,000

5
Bedrooms
0.06
Acres
$1,650,000 | 2030 North Lincoln Avenue, Unit AB, Chicago, IL 60614

$1,650,000

5
Bedrooms
4,000
Square Feet
$1,455,000 | 1830 West Newport Avenue, Chicago, IL 60657

$1,455,000

4
Bedrooms
4,200
Square Feet
0.07
Acres
a front view of a house with a yard

$1,375,000

12
Bedrooms
0.07
Acres
a building view

$1,325,000

3
Bedrooms
a front view of a house with a yard

$1,295,000

5
Bedrooms
3,800
Square Feet
0.08
Acres
a front view of a residential apartment building with a yard

$1,150,000

12
Bedrooms
4,984
Square Feet
0.07
Acres
a view of the door of the house

$989,989

2
Bedrooms
2,100
Square Feet
a view of a house with a door and a yard

$975,000

3
Bedrooms
front view of a house with a yard

$880,000

4
Bedrooms
2,487
Square Feet
a front view of multiple houses

$855,000

4
Bedrooms
3,933
Square Feet
0.18
Acres
a front view of house with a garden

$850,000

3
Bedrooms
2,650
Square Feet
a front view of house with yard and green space

$850,000

4
Bedrooms
3,600
Square Feet
1.09
Acres
front view of a building

$839,000

3
Bedrooms
2,200
Square Feet
a view of a tall building next to a road

$814,000

2
Bedrooms
1,709
Square Feet
$790,000 | 2422 North Racine Avenue, Unit 2, Chicago, IL 60614

$790,000

2
Bedrooms
1,400
Square Feet
a front view of a house with a garden

$775,000

4
Bedrooms
5,159
Square Feet
0.89
Acres
Past Rentals
a view of a city with tall buildings

$25,000

4
Bedrooms
3,922
Square Feet
a front view of a building with street view

$4,450

3
Bedrooms
1,200
Square Feet
a building view

$3,250

2
Bedrooms
a building view

$3,000

2
Bedrooms
a front view of a building with lot of cars and trees

$2,900

2
Bedrooms
1,800
Square Feet
$2,586 | 1454 W Randolph St, Unit 818 | Chicago

$2,586

1454 W Randolph St, Unit 818

Chicago

$2,200 | 155 North Harbor Drive, Unit 4007, Chicago, IL 60601

$2,200

1
Bedrooms
990
Square Feet
a view of a multi story building

$1,900

1
Bedrooms
660
Square Feet
front view of a building

$1,900

1
Bedrooms
1,000
Square Feet
a front view of a building

$1,700

1
Bedrooms
650
Square Feet
$1,675 | 222 North Columbus Drive, Unit 2907, Chicago, IL 60601

$1,675

1
Bedrooms
660
Square Feet
$1,550 | 222 North Columbus Drive, Unit 2606, Chicago, IL 60601

$1,550

1
Bedrooms
685
Square Feet
$1,550 | 222 North Columbus Drive, Unit 3904, Chicago, IL 60601

$1,550

1
Bedrooms
660
Square Feet