Naples Home Collective, Real Estate Agents - Compass

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About Naples Home Collective

The Naples Home Collective is a top-producing real estate team based in Naples, Florida, delivering a high-touch, strategic, and design-forward approach to real estate across Southwest Florida and Chicago. Led by Madeline Tracy and Jordan Pyle - The team was proudly ranked in the Top 1.5% of all small teams Nationwide by Real Trends Verified for their sales volume in 2024. A reflection of their results-driven mindset and unwavering client focus.

Madeline Tracy, a Naples native, leads the team with a refined eye for detail and a background in new construction, interior design, and luxury client experience. Her longstanding relationships with local builders and investors, paired with her ability to create customized, strategic plans for each client, have made her a standout voice in Naples’ evolving high-end market.

Jordan Pyle, licensed in both Illinois and Florida, brings a dual-market advantage to the team. This unique qualification not only allows him to assist clients in both Chicago and Southwest Florida but also makes him an invaluable resource for buyers and investors seeking second homes or vacation properties. Jordan developed a reputation for delivering top-tier results, earning recognition as one of the National Association of Realtors’ “30 Under 30." With expertise in digital marketing, negotiations, and client service, he ensures that every transaction is both smooth and successful.

Together, the Naples Home Collective offers a modern, collaborative real estate experience designed for today’s luxury buyer and seller. Whether you're relocating, investing, or simply looking for a trusted advisor in Southwest Florida, the team delivers expertise, integrity, and a tailored approach that turns real estate goals into reality.

Team Agents

Naples Home Collective’s Transactions

Past Sales

a view of a swimming pool with a table and chairs under an umbrella

$4,550,000

5
Bedrooms: 8
Bathrooms: 4,879
Square Feet: 0.5
Acres

872 Inlet Drive, Marco Island, FL 34145

a front view of a house with garden

$3,700,000

5
Bedrooms: 5
Bathrooms: 5,251
Square Feet: 2.73
Acres

6610 Sable Ridge Lane, Naples, FL 34109

an aerial view of residential houses with outdoor space and city view

$3,050,000

5
Bedrooms: 5
Bathrooms: 6,475
Square Feet: 0.31
Acres

1436 Viking Court, Cape Coral, FL 33904

front view of a house

$2,350,000

5
Bedrooms: 5
Bathrooms: 0.07
Acres

3338 North Lakewood Avenue, Chicago, IL 60657

an outdoor space with pool and furniture

$2,225,000

3
Bedrooms: 4
Bathrooms: 3,795
Square Feet: 0.36
Acres

27501 Country Club Drive, Bonita Springs, FL 34134

a kitchen with a table chairs and a refrigerator

$1,950,000

4
Bedrooms: 4
Bathrooms: 2,990
Square Feet: 0.38
Acres

26384 Augusta Creek Court, Bonita Springs, FL 34134

$1,900,000 | 245 2nd Street, Bonita Springs, FL 34134

$1,900,000

5
Bedrooms: 5
Bathrooms: 3,000
Square Feet: 0.21
Acres

245 2nd Street, Bonita Springs, FL 34134

$1,900,000 | 16417 Carrara Way, Unit 202, Naples, FL 34110

$1,900,000

3
Bedrooms: 4
Bathrooms: 2,950
Square Feet

16417 Carrara Way, Unit 202, Naples, FL 34110

a living room with fireplace furniture and a large window

$1,850,000

3
Bedrooms: 4
Bathrooms: 2,930
Square Feet

16371 Viansa Way, Unit 201, Naples, FL 34110

a front view of a house with a yard

$1,825,000

3
Bedrooms: 3
Bathrooms: 3,424
Square Feet: 0.52
Acres

12495 Collier's Reserve Drive, Naples, FL 34110

$1,795,000

5
Bedrooms: 4
Bathrooms: 0.06
Acres

1249 West Lill Avenue, Chicago, IL 60614

a living room with furniture and a large window

$1,650,000

3
Bedrooms: 3
Bathrooms: 2,833
Square Feet

4801 Bonita Bay Boulevard, Unit 1103, Bonita Springs, FL 34134

$1,650,000 | 2030 North Lincoln Avenue, Unit AB, Chicago, IL 60614

$1,650,000

5
Bedrooms: 5
Bathrooms: 4,000
Square Feet

2030 North Lincoln Avenue, Unit AB, Chicago, IL 60614

a bathroom with a sink a vanity and a mirror

$1,575,000

3
Bedrooms: 2
Bathrooms: 1,600
Square Feet

990 Cape Marco Drive, Unit 504, Marco Island, FL 34145

$1,525,000 | 2331 McClellan Parkway, Sarasota, FL 34239

$1,525,000

3
Bedrooms: 3
Bathrooms: 2,025
Square Feet: 0.26
Acres

2331 McClellan Parkway, Sarasota, FL 34239

a view of a yard with a tree

$1,500,000

4
Bedrooms: 4
Bathrooms: 3,383
Square Feet: 0.44
Acres

26384 Mahogany Pointe Court, Bonita Springs, FL 34134

$1,455,000 | 1830 West Newport Avenue, Chicago, IL 60657

$1,455,000

4
Bedrooms: 4
Bathrooms: 4,200
Square Feet: 0.07
Acres

1830 West Newport Avenue, Chicago, IL 60657

a front view of a house with a yard and garage

$1,400,000

3
Bedrooms: 3
Bathrooms: 2,366
Square Feet: 2.81
Acres

202 Golden Gate Boulevard West, Naples, FL 34117

Past Rentals

a view of a city with tall buildings

$25,000

4
Bedrooms: 5
Bathrooms: 3,922
Square Feet

13910 Old Coast Road, Unit 404, Naples, FL 34110

a view of hallway with wooden floor

$4,500

4
Bedrooms: 3
Bathrooms: 1,938
Square Feet

3012 Pine Tree Drive, Naples, FL 34112

a front view of a building with street view

$4,450

3
Bedrooms: 2
Bathrooms: 1,200
Square Feet

637 West Armitage Avenue, Unit 1, Chicago, IL 60614

$4,000 | 185 4th Street South, Unit 2, Naples, FL 34102

$4,000

2
Bedrooms: 3
Bathrooms: 1,302
Square Feet

185 4th Street South, Unit 2, Naples, FL 34102

a building view

$3,250

2
Bedrooms: 2
Bathrooms

821 West Superior Street, Unit 3, Chicago, IL 60642

a building view

$3,000

2
Bedrooms: 2
Bathrooms

821 West Superior Street, Unit 3, Chicago, IL 60642

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

$2,900

2
Bedrooms: 2
Bathrooms: 1,800
Square Feet

6135 North Broadway, Unit 602, Chicago, IL 60660

$2,600

2
Bedrooms: 2
Bathrooms: 1,326
Square Feet

13141 Hamilton Harbour Drive, Unit P8, Naples, FL 34110

$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: 2
Bathrooms: 990
Square Feet

155 North Harbor Drive, Unit 4007, Chicago, IL 60601

front view of a brick house with a small yard

$2,150

2
Bedrooms: 3
Bathrooms: 1,415
Square Feet

9080 Gervais Circle, Unit 507, Naples, FL 34120

a view of a multi story building

$1,900

1
Bedrooms: 1
Bathrooms: 660
Square Feet

222 North Columbus Drive, Unit 3904, Chicago, IL 60601

front view of a building

$1,900

1
Bedrooms: 1
Bathrooms: 1,000
Square Feet

2623 North Kimball Avenue, Unit 2R, Chicago, IL 60647

a front view of a building

$1,700

1
Bedrooms: 1
Bathrooms: 650
Square Feet

222 East Pearson Street, Unit 1105, Chicago, IL 60611

$1,675 | 222 North Columbus Drive, Unit 2907, Chicago, IL 60601

$1,675

1
Bedrooms: 1
Bathrooms: 660
Square Feet

222 North Columbus Drive, Unit 2907, Chicago, IL 60601

$1,550 | 222 North Columbus Drive, Unit 2606, Chicago, IL 60601

$1,550

1
Bedrooms: 1
Bathrooms: 685
Square Feet

222 North Columbus Drive, Unit 2606, Chicago, IL 60601

$1,550 | 222 North Columbus Drive, Unit 3904, Chicago, IL 60601

$1,550

1
Bedrooms: 1
Bathrooms: 660
Square Feet

222 North Columbus Drive, Unit 3904, Chicago, IL 60601